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67-56-1 Usage

Introduction

Methanol is the simplest fatty alcohol. It is a colorless, flammable, irritating liquid with a boiling point of 64.7°C, a melting point of -93.90°C, and a relative density of 0.7913. Soluble in water and most organic solvents. Its severe toxicity can damage the optic nerve. Once swallowed, it can make the eyes blind and even cause death. Methanol has the general properties of a primary aliphatic alcohol. The three hydrogen atoms on a carbon atom with a hydroxyl group can be oxidized, orderly generating formaldehyde, formic acid, and carbon dioxide. Therefore, it is largely used in the synthesis of formaldehyde. Methanol is easily converted into important organic synthesis intermediates such as methyl carboxylate, methyl chloride and methylamine, and it is also applied as important organic solvents, extraction agents and alcohol denaturants.

Chemical Properties

Different sources of media describe the Chemical Properties of 67-56-1 differently. You can refer to the following data:
1. Methanol is a clear, colorless liquid with a characteristic pungent odor (NTP NIEHS web accessed 2/16/2013). The air odor threshold has been reported as 1500 ppm (approximately 2000mg/m3), much higher than the occupational guidelines. Methanol (methyl alcohol; wood alcohol) is used extensively as a solvent for lacquers, paints, varnishes, cements, inks, dyes, plastics, and various industrial coatings. Large quantities are used in the production of formaldehyde and other chemical derivatives such as acetic acid, methyl halides and terephthalate, methyl methacrylate, and methylamines. Methanol is also used as a gasoline additive, as a component of lacquer thinners, in antifreeze preparations of the “nonpermanent” type, and in canned heating preparations of jellied alcohol. It is also used in duplicating fluid, in paint removers, and as a cleaning agent. The potential for methanol as a future alternative for gasoline indicates that the use of this chemical will most likely increase rather than decrease. At room temperature, methanol is a colorless liquid with a pungent odor. It is relatively volatile, with a vapor pressure of 96 mmHg and a vapor density of 1.11. It is miscible with water and soluble with other organic solvents. It is found in nature as a fermentation product of wood and as a constituent of some fruits and vegetables.
2. Methanol is a clear, water-white liquid with a mild odor at ambient temperatures.The air odor threshold for methanol has been reported as 100 ppm . Others have reported that 2000 or 5900 ppm methanol is barely detectable .

Uses

Different sources of media describe the Uses of 67-56-1 differently. You can refer to the following data:
1. Methanol is an important chemical raw material for fine chemicals. Its carbonylation at 3.5 MPa and 180-200° C in the presence of catalyst can produce acetic acid and further produce acetic anhydride. It reacts with syngas to prepare vinyl acetate in the presence of catalyst; reacts with isobutylene to produce tert-butyl methyl ether; prepare dimethyl oxalate through oxidization and carbonylation, and a further hydrogenation to produce ethylene glycol; reacts with toluene under catalyst and simultaneous oxidization to produce phenylethyl alcohol. It can be used as a good solvent, as a pesticide raw material, as an antifreeze agent, as a fuel and fuel additive (this is receiving increasing attention in environmental protection field). It is the main raw material in the preparation of formaldehyde, the raw material in medicine and spices production, a solvent in dyes and paint industries, the raw material in preparation of methanol single cell protein and synthesis of methyl ester. ▼▲ Industry Applications Role/Benefit Laboratory HPLC, UV/VIS spectroscopy, and LCMS Low UV cutoff Chemical manufacture Production of formaldehyde and its derivates Main feedstock Production of hydrocarbon chains and even aromatic systems Main feedstock Production of methyl tert-butyl ether Methylation reagent Production of dimethyl terephthalic acid, methyl methacrylate and acrylic acid methyl ester Main feedstock Plastics Production of polymers Main feedstock Farm chemical Production of insecticide and acaricide Main feedstock Pharmaceuticals Production of sulfonamides, amycin, etc Main feedstock Fuel for vehicles Pure methanol fuel Pure methanol does not produce an opaque cloud of smoke in the event of an accident Methanol gasoline Blended directly into gasoline to produce a high-octane, efficient fuel with lower emissions than conventional gasoline Chemical analysis Determination of boron Analysis agent Determination of trace moisture in alcohols, saturated hydrocarbons, benzene, chloroform, pyridine Analysis agent Others Separation of calcium sulfate and magnesium sulfate Separation reagent Separation of strontium bromide and barium bromide Separation reagent Anti-freezing agent Effective component
2. Methanol has numerous uses. Its main use is in the production of formaldehyde, whichconsumes approximately 40% of methanol supplies. Methanolis a common organic solvent found in many products including deicers (windshield wiperfl uid), antifreezes, correction fl uid, fuel additives, paints, and other coatings. A number ofindustrial chemicals use methanol in their production. Among these are methyl methacrylateand dimethyl terephthalate. Methanol is used to convert methylacrylamide sulfate to methylmethacrylate and ammonium hydrogen sulfate (NH4HSO4):Methanol is used in making the ester dimethyl terephthalate from mixtures ofxylene of toluene. Dimethyl terephthalate is used in the manufacture of polyesters and plastics.Methanol is used as a fuel additive. The common gasoline additive HEET is pure methanoland is used as a gas-line antifreeze and water remover. Methanol is used as a fuel in camp stoves and small heating devices. It is used to fuel the small engines used in models (airplanes,boats). In the early history of automobiles,methanol was a common fuel. The availability of cheap gasoline replaced methanol in the1920s, but it is receiving renewed interest as an alternative fuel as the demand and cost of oilincrease and oil supplies become uncertain. Methanol can be produced from coal and biomass.Methanol has a higher octane rating and generally lower pollutant emissions compared togasoline. The relatively low flame temperature means that fewer nitrogen oxides are producedby methanol than by ethanol. One large disadvantage of methanol is that it has a lower energydensity than gasoline. Using equivalent volumes of gasoline and methanol, methanol givesabout half the mileage of gasoline. Another problem with methanol is its low vapor pressure,resulting in starting problems on cold days. This problem can be mitigated by using a blendof 85% methanol and 15% gasoline. This mixture is called M85 and is similar to E85 ethanol(see Ethyl Alcohol).
3. Methanol is used in the production offormaldehyde, acetic acid, methyl tert-butylether, and many chemical intermediates; asan octane improver (in oxinol); and as apossible alternative to diesel fuel; being anexcellent polar solvent, it is widely used as acommon laboratory chemical and as a methylating reagent.
4. high purity grade for ICP-MS detection
5. Methylalcohol, CH30H, also known as methanol or wood alcohol, is a colorless, toxic, flammable liquid with a boiling point of 64.6 °C(147 °F). The principal toxic effect is on the nervous system,particularly the retinae. Methyl alcoholis miscible in all proportions with water,ethyl alcohol, and ether. It burns with a light blue flame producing water and carbon dioxide. This vapor forms an explosive mixture(6.0 to 36.5% by volume) with air. Methyl alcohol is an important inexpensive raw material that is synthetically produced for the organic chemical industry. Nearly half of the methyl alcohol manufactured is used in the production of formaldehyde. Other uses of methyl alcohol are as an antifreeze and fuel for automobiles and as an intermediate in the production of synthetic protein.
6. Industrial solvent. Raw material for making formaldehyde and methyl esters of organic and inorganic acids. Antifreeze for automotive radiators and air brakes; ingredient of gasoline and diesel oil antifreezes. Octane booster in gasoline. As fuel for picnic stoves and soldering torches. Extractant for animal and vegetable oils. To denature ethanol. Softening agent for pyroxylin plastics. Solvent and solvent adjuvant for polymers. Solvent in the manufacture of cholesterol, streptomycin, vitamins, hormones, and other pharmaceuticals.

Methanol poisoning and First Aid Measures

Pathogenesis First, methanol has a cumulative effect and is oxidized in the body into more toxic formaldehyde and formic acid. Methanol and its oxides directly damage the tissues, causing cerebral edema, meningeal hemorrhage, optic nerve and retinal atrophy, pulmonary congestion and edema, and hepatic and renal turbid swelling. Second, methanol and its oxides cause blood circulation disorder, coenzyme system obstacles in vivo, resulting in lack of oxygen supply to the brain cortical cells, metabolic disorders, and related neurological and psychiatric symptoms. Third, methanol oxidation products combine with the iron in the cytochrome oxidase, which inhibits the intracellular oxidation process thus causing metabolic disorders, acidosis along with organic acid accumulation in the body, and nerve cells impair. Treatment Keep away from the methanol dispersion area, excrete methanol from the body. Antidote: Ethanol is an antidote to methanol poisoning. Ethanol can prevent methanol’s oxidation and promote its emission. Prepare 5% ethanol solution using 10% glucose solution, and drip slowly intravenously. Maintain electrolyte balance: maintain respiratory and circulatory function, provide with a large number of Vitamin B. Treatment of acidosis: Administrate timely sodium bicarbonate solution or sodium lactate solution based on blood gas analysis, carbon dioxide binding force measurement and clinical performance. Prevent cerebral edemas actively, reduce intracranial pressure, improve fundus blood circulation, and prevent optic neuropathy if needed. Inject intravenously cytochrome C, polar fluid to restore cytochrome oxidase function. Control mental state by applying diazepam, perphenazine and the like. Symptoms and treatments: ▼▲ Acute pain morphine, pethidine Convulsions phenobarbital, amimystrine, diazepam Coma caffeine sodium benzoate Respiratory failure nikethamide, theophylline

Reactivities of Methanol

Methanol is the simplest aliphatic alcohol. It contains only one carbon atom. Unlike higher alcohols, it cannot form an olefin through dehydration. However, it can undergo other typical reactions of aliphatic alcohols involving cleavage of a C-H bond or O-H bond and displacement of the -OH group. Table 1 summarizes the reactions of methanol, which are classified in terms of their mechanisms. Examples of the reactions and products are given. Homolytic dissociation energies of the C-O and O-H bonds in methanol are relatively high. Catalysts are often used to activate the bonds and to increase the selectivity to desired products.

Production

Methanol is prepared by pressure heating with carbon monoxide and hydrogen in the presence of a catalyst: ? ? If the conditions are strictly controlled, the yield can reach 100% and the purity can reach 99%. Methane is mixed with oxygen (9:1, V/V) and methanol is obtained through a copper tube under heating and pressure:

Toxicity evaluation

Different sources of media describe the Toxicity evaluation of 67-56-1 differently. You can refer to the following data:
1. ADI is limited to GMP (FAO/WHO, 2001). Toxic, can cause blindness. LD50: 5628 mg/kg (rat, oral). ? Measurement Date System Route/Organism Dose Effect Skin and Eye Irritation December 2016 ? eye /rabbit 40 mg moderate Skin and Eye Irritation December 2016 ? eye /rabbit 100 mg/24H moderate Skin and Eye Irritation December 2016 ? skin /rabbit 20 mg/24H moderate Mutation Data December 2016 Cytogenetic Analysis parenteral/grasshopper 3000 ppm ? Mutation Data December 2016 Cytogenetic Analysis oral/mouse 1 gm/kg ? Mutation Data December 2016 Cytogenetic Analysis intraperitoneal/mouse 75 mg/kg ? Mutation Data December 2016 DNA Damage oral/rat 10 μmol/kg ? Mutation Data December 2016 DNA inhibition lymphocyte/human 300 mmol/L ? Mutation Data December 2016 DNA repair /Escherichia coli 20 mg/well ? Mutation Data December 2016 morphological transform fibroblast/mouse 0.01 mg/L/21D (-enzymatic activation step) ? from The National Institute for Occupational Safety and Health - NIOSH
2. The toxic properties of methanol are the result of accumulation of the formate intermediate in the blood and tissues of exposed individuals. Formate accumulation produces metabolic acidosis leading to the characteristic ocular toxicity (blindness) observed in human methanol poisonings. Humans and primates appear particularly sensitive to methanol toxicity when compared to rats. This is attributed to the slower rate of conversion in humans of the formate metabolite via tetrahydrofolate. This step in methanol metabolism occurs in rats at a rate ~2.5 times that observed in humans. Formate appears to directly affect the retina and optic nerve by acting as a mitochondrial toxin. It is believed that formate acts as a metabolic poison by inhibiting cytochrome oxidase activity. The cells of the optic nerve have low reserves of cytochrome oxidase and thus may be particularly sensitive to formate-induced metabolic inhibition.

Methanol gasoline

Methanol gasoline refers to the M series mixture fuel made of addition of methanol to the gasoline and formulated using methanol fuel solvent. Among them, M15 (add 15% methanol in gasoline) clean methanol gasoline is used as vehicle fuel, respectively, used in a variety of gasoline engines. It can be applied to substitute the finished gasoline without changing the existing engine structure, and can also be mixed with refined oil. The methanol mixed fuel has excellent thermal efficiency, power, start-up and being economical. It is also characterized by lowering the emissions, saving oil and being safe and convenient. Methanol gasoline types of M35, M15, M20, M50, N85 and M100 with different blend ratios have been developed around the world according to the conditions of different countries. At present, the commercial methanol is mainly M85 (85% methanol + 15% gasoline) and M100 with M100 performance being better than M85 and having greater environmental advantages.

Description

Methyl alcohol, also known as methanol or wood alcohol, is a clear, colorless, flammable liquid that is the simplest alcohol.World production of methanol is approximately 8.5 billion gallons annually. Methanol is produced industrially, starting with the production of synthesis gas or syngas. Syngas used in the production of methyl alcohol is a mixture of carbon monoxide and hydrogen formed when natural gas reacts with steam or oxygen. Methyl alcohol is then synthesized from carbon monoxide and hydrogen.Methyl alcohol is poisonous and is commonly used to denature ethyl alcohol. Methanol poisoning results from ingestion, inhalation of methanol vapors, or absorption through the skin. Methanol is transformed in the body to formaldehyde (H2CO) by the enzyme alcohol dehydrogenase.The formaldehyde is then metabolized to formic acid (HCOOH)by aldehyde dehydrogenase.

Physical properties

Clear, colorless liquid with a characteristic alcoholic odor. Odor threshold concentrations ranged from 8.5 ppbv (Nagata and Takeuchi, 1990) to 100.0 ppmv (Leonardos et al., 1969). Experimentally determined detection and recognition odor threshold concentrations were 5.5 mg/m3 (4.2 ppmv) and 69 mg/m3 (53 ppmv), respectively (Hellman and Small, 1974).

History

It was first isolated in 1661 by the Irish chemist Robert Boyle (1627–1691) who prepared it by the destructive distillation of boxwood, giving it the name spirit of box, and the name wood alcohol is still used for methyl alcohol. Methyl alcohol is also called pyroxylic spirit; pyroxylic is a general term meaning distilled from wood and indicates that methyl alcohol is formed during pyrolysis of wood. The common name was derived in the mid-1800s. The name methyl denotes the single carbon alkane methane in which a hydrogen atom has been removed to give the methyl radical. The word alcohol is derived from Arabic al kuhul.

Definition

ChEBI: Methanol is the primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group. It has a role as an amphiprotic solvent, a fuel, a human metabolite, an Escherichia coli metabolite, a mouse metabolite and a Mycoplasma genitalium metabolite. It is an alkyl alcohol, a one-carbon compound, a volatile organic compound and a primary alcohol. It is a conjugate acid of a methoxide.

Production Methods

Modern industrial-scale methanol production is exclusively based on synthesis from pressurized mixtures of hydrogen, carbon monoxide, and carbon dioxide gases in the presence of catalysts. Based on production volume, methanol has become one of the largest commodity chemicals produced in the world.

Reactions

Methyl alcohol is a versatile material, reacting (1) with sodium metal, forming sodium methylate, sodium methoxide CH3ONa plus hydrogen gas, (2) with phosphorus chloride, bromide, iodide, forming methyl chloride, bromide, iodide, respectively, (3) with H2SO4 concentrated, forming dimethyl ether (CH3)2O, (4) with organic acids, warmed in the presence of H2SO4, forming esters, e.g., methyl acetate CH3COOCH3, [CAS: 79-20-9], methyl salicylate C6H4(OH)·COOCH3, possessing characteristic odors, (5) with magnesium methyl iodide in anhydrous ether (Grignard’s solution), forming methane as in the case of primary alcohols, (6) with calcium chloride, forming a solid addition compound 4CH3OH·CaCl2, which is decomposed by H2O, (7) with oxygen, in the presence of heated smooth copper or silver forming formaldehyde. The density of pure methyl alcohol is 0.792 at 20 °C compared with H2O at 4 °C (the corresponding figure for ethyl alcohol is 0.789), and the percentage of methyl alcohol present in a methyl alcohol-water solution may be determined from the density of the sample.

World Health Organization (WHO)

Methanol has been subjected to abuse by consumption as a substitute for ethanol. Its toxic metabolites cause irreversible blindness and severe metabolic acidosis, and are ultimately fatal. Methanol continues to be used as an industrial solvent.

General Description

A colorless fairly volatile liquid with a faintly sweet pungent odor like that of ethyl alcohol. Completely mixes with water. The vapors are slightly heavier than air and may travel some distance to a source of ignition and flash back. Any accumulation of vapors in confined spaces, such as buildings or sewers, may explode if ignited. Used to make chemicals, to remove water from automotive and aviation fuels, as a solvent for paints and plastics, and as an ingredient in a wide variety of products.

Reactivity Profile

Methanol reacts violently with acetyl bromide [Merck 11th ed. 1989]. Mixtures with concentrated sulfuric acid and concentrated hydrogen peroxide can cause explosions. Reacts with hypochlorous acid either in water solution or mixed water/carbon tetrachloride solution to give methyl hypochlorite, which decomposes in the cold and may explode on exposure to sunlight or heat. Gives the same product with chlorine. Can react explosively with isocyanates under basic conditions. The presence of an inert solvent mitigates this reaction [Wischmeyer 1969]. A violent exothermic reaction occurred between methyl alcohol and bromine in a mixing cylinder [MCA Case History 1863. 1972]. A flask of anhydrous lead perchlorate dissolved in Methanol exploded when Methanol was disturbed [J. Am. Chem. Soc. 52:2391. 1930]. P4O6 reacts violently with Methanol. (Thorpe, T. E. et al., J. Chem. Soc., 1890, 57, 569-573). Ethanol or Methanol can ignite on contact with a platinum-black catalyst. (Urben 1794).

Hazard

Flammable, dangerous fire risk. Explosive limits in air 6–36.5% by volume. Toxic by ingestion (causes blindness). Headache, eye damage, dizziness, and nausea.

Health Hazard

Different sources of media describe the Health Hazard of 67-56-1 differently. You can refer to the following data:
1. Ingestion of adulterated alcoholic beveragescontaining methanol has resulted in innumerable loss of human lives throughout theworld. It is highly toxic, causing acidosis andblindness. The symptoms of poisoning arenausea, abdominal pain, headache, blurredvision, shortness of breath, and dizziness.In the body, methanol oxidizes to formaldehyde and formic acid — the latter could bedetected in the urine, the pH of which is lowered (when poisoning is severe).The toxicity of methanol is attributed tothe metabolic products above. Ingestion inlarge amounts affects the brain, lungs, gastrointestinal tract, eyes, and respiratory system and can cause coma, blindness, anddeath. The lethal dose is reported to be60–250 mL. The poisoning effect is prolonged and the recovery is slow, often causing permanent loss of sight.Other exposure routes are inhalation andskin absorption. Exposure to methanol vaporto at 2000 ppm at regular intervals over aperiod of 4 weeks caused upper respiratorytract irritation and mucoid nasal discharge inrats. Such discharge was found to be a doserelated effect.Inhalation in humans may produce headache, drowsiness, and eye irritation. Prolonged skin contact may cause dermatitis andscaling. Eye contact can cause burns anddamage vision..
2. The acute toxicity of methanol by ingestion, inhalation, and skin contact is low. Ingestion of methanol or inhalation of high concentrations can produce headache, drowsiness, blurred vision, nausea, vomiting, blindness, and death. In humans, 60 to 250 mL is reported to be a lethal dose. Prolonged or repeated skin contact can cause irritation and inflammation; methanol can be absorbed through the skin in toxic amounts. Contact of methanol with the eyes can cause irritation and burns. Methanol is not considered to have adequate warning properties. Methanol has not been found to be carcinogenic in humans. Information available is insufficient to characterize the reproductive hazard presented by methanol. In animal tests, the compound produced developmental effects only at levels that were maternally toxic; hence, it is not considered to be a highly significant hazard to the fetus. Tests in bacterial or mammalian cell cultures demonstrate no mutagenic activity

Flammability and Explosibility

Methanol is a flammable liquid (NFPA rating = 3) that burns with an invisible flame in daylight; its vapor can travel a considerable distance to an ignition source and "flash back." Methanol-water mixtures will burn unless very dilute. Carbon dioxide or dry chemical extinguishers should be used for methanol fires.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization:Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

A human poison by ingestion. Poison experimentally by skin contact. Moderately toxic experimentally by intravenous and intraperitoneal routes. Mildly toxic by inhalation. Human systemic effects: changes in circulation, cough, dyspnea, headache, lachrymation, nausea or vomiting, optic nerve neuropathy, respiratory effects, visual field changes. An experimental teratogen. Experimental reproductive effects. An eye and skin irritant. Human mutation data reported. A narcotic. Its main toxic effect is exerted upon the nervous system, particularly the optic nerves and possibly the retinae. The condtion can progress to permanent blindness. Once absorbed, methanol is only very slowly eliminated. Coma resulting from massive exposures may last as long as 2-4 days. In the body, the products formed by its oxidation are formaldehyde and formic acid, both of which are toxic. Because of the slow elimination, methanol should be regarded as a cumulative poison. Though single exposures to fumes may cause no harmful effect, daily exposure may result in the accumulation of sufficient methanol in the body to cause illness. Death from ingestion of less than 30 mL has been reported. A common air contaminant. Flammable liquid. Dangerous fire hazard when exposed to heat, flame, or oxidlzers. Explosive in the form of vapor when exposed to heat or flame. Explosive reaction with chloroform + sodium methoxide, diethyl zinc. Violent reaction with alkyl aluminum salts, acetyl bromide, chloroform + sodlum hydroxide, CrO3, cyanuric chloride, (I + ethanol + HgO), Pb(ClO4)2, HClO4, P2O3, (KOH + CHCb), nitric acid. Incompatible with berylhum dihydride, metals (e.g., potassium, magnesium), oxidants (e.g., barium perchlorate, bromine, sodium hypochlorite, chlorine, hydrogen peroxide), potassium tert-butoxide, carbon tetrachloride + metals (e.g., aluminum, magnesium, zinc), dlchloromethane. Dangerous; can react vigorously with oxidizing materials. To fight fire, use alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes.

Source

Methanol occurs naturally in small-flowered oregano (5 to 45 ppm) (Baser et al., 1991), Guveyoto shoots (700 ppb) (Baser et al., 1992), orange juice (0.8 to 80 ppm), onion bulbs, pineapples, black currant, spearmint, apples, jimsonweed leaves, soybean plants, wild parsnip, blackwood, soursop, cauliflower, caraway, petitgrain, bay leaves, tomatoes, parsley leaves, and geraniums (Duke, 1992). Methanol may enter the environment from methanol spills because it is used in formaldehyde solutions to prevent polymerization (Worthing and Hance, 1991).

Environmental fate

Biological. In a 5-d experiment, [14C]methanol applied to soil water suspensions under aerobic and anaerobic conditions gave 14CO2 yields of 53.4 and 46.3%, respectively (Scheunert et al., 1987). Heukelekian and Rand (1955) reported a 5-d BOD value of 0.85 g/g which is 56.7% of the ThOD value of 1.50 g/g. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM methanol) and ThOD were 0.93 and 62.0%, respectively (Vaishnav et al., 1987). Photolytic. Photooxidation of methanol in an oxygen-rich atmosphere (20%) in the presence of chlorine atoms yielded formaldehyde and hydroxyperoxyl radicals. The reaction is initiated via hydrogen abstraction by OH radicals or chlorine atoms yielding a hydroxymethyl radical. Chlorine, formaldehyde, carbon monoxide, hydrogen peroxide, and formic acid were detected (Whitbeck, 1983). Reported rate constants for the reaction of methanol and OH radicals in the atmosphere: 5.7 x 10-11 cm3/mol·sec at 300 K (Hendry and Kenley, 1979), 5.7 x 10-8 L/mol·sec (second-order) at 292 K (Campbell et al., 1976), 1.00 x 10-12 cm3/molecule·sec at 292 K (Meier et al., 1985), 7.6 x 10-13 cm3/molecule·sec at 298 K (Ravishankara and Davis, 1978), 6.61 x 10-13 cm3/molecule·sec at room temperature (Wallington et al., 1988a). Based on an atmospheric OH concentration of 1.0 x 106 molecule/cm3, the reported half-life of methanol is 8.6 d (Grosjean, 1997). Chemical/Physical. In a smog chamber, methanol reacted with nitrogen dioxide to give methyl nitrite and nitric acid (Takagi et al., 1986). The formation of these products was facilitated when this experiment was accompanied by UV light (Akimoto and Takagi, 1986). Methanol will not hydrolyze because it does not have a hydrolyzable functional group (Kollig, 1993). At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 964 mg/L. The adsorbability of the carbon used was 7 mg/g carbon (Guisti et al., 1974). Hydroxyl radicals react with methanol in aqueous solution at a reaction rate of 1.60 x 10-12 cm3/molecule?sec (Wallington et al., 1988). Complete combustion in air produces carbon dioxide and water. The stoichiometric equation for this oxidation reaction is: 2CH4O + 3O2 → 2CO2 + 4H2O

storage

Methanol should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

Shipping

UN1230 Methanol, Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous material. (International)

Purification Methods

Almost all methanol is now obtained synthetically. Likely impurities are water, acetone, formaldehyde, ethanol, methyl formate and traces of dimethyl ether, methylal, methyl acetate, acetaldehyde, carbon dioxide and ammonia. Most of the water (down to about 0.01%) can be removed by fractional distillation. Drying with CaO is unnecessary and wasteful. Anhydrous methanol can be obtained from "absolute" material by passage through Linde type 4A molecular sieves, or by drying with CaH2, CaSO4, or with just a little more sodium than required to react with the water present, in all cases the methanol is then distilled. Two treatments with sodium reduces the water content to about 5 x 10-5%. [Friedman et al. J Am Chem Soc 83 4050 1961.] Lund and Bjerrum [Chem Ber 64 210 1931] warmed clean dry magnesium turnings (5g) and iodine (0.5g) with 50-75mL of "absolute" methanol in a flask until the iodine disappeared and all the magnesium was converted to the methoxide. Up to 1L of methanol was added and, after refluxing for 2-3hours, it was distilled off, excluding moisture from the system. Redistillation from tribromobenzoic acid removes basic impurities and traces of magnesium oxides, and leaves conductivity-quality material. The method of Hartley and Raikes [J Chem Soc 127 524 1925] gives a slightly better product. This consists of an initial fractional distillation, followed by distillation from aluminium methoxide, and then ammonia and other volatile impurities are removed by refluxing for 6hours with freshly dehydrated CuSO4 (2g/L) while dry air is passed through: the methanol is finally distilled. (The aluminium methoxide is prepared by warming with aluminium amalgam (3g/L) until all the aluminium has reacted. The amalgam is obtained by warming pieces of sheet aluminium with a solution of HgCl2 in dry methanol.) This treatment also removes aldehydes. If acetone is present in the methanol, it is usually removed prior to drying. Bates, Mullaly and Hartley [J Chem Soc 401 1923] dissolved 25g of iodine in 1L of methanol and then poured the solution, with constant stirring, into 500mL of M NaOH. Addition of 150mL of water precipitated iodoform. The solution was allowed to stand overnight, filtered, then boiled under reflux until the odour of iodoform disappeared, and fractionally distilled. (This treatment also removes formaldehyde.) Morton and Mark [Ind Eng Chem (Anal Edn) 6 151 1934] refluxed methanol (1L) with furfural (50mL) and 10% NaOH solution (120mL) for 6-12hours, the refluxing resin carries down with it the acetone and other carbonyl-containing impurities. The alcohol was then fractionally distilled. Evers and Knox [J Am Chem Soc 73 1739 1951], after refluxing 4.5L of methanol for 24hours with 50g of magnesium, distilled off 4L of it, which they then refluxed with AgNO3 for 24hours in the absence of moisture or CO2. The methanol was again distilled, shaken for 24hours with activated alumina before being filtered through a glass sinter and distilled under nitrogen in an all-glass still. Material suitable for conductivity work was obtained. Variations of the above methods have also been used. For example, a sodium hydroxide solution containing iodine has been added to methanol and, after standing for 1day, the solution has been poured slowly into about a quarter of its volume of 10% AgNO3, shaken for several hours, then distilled. Sulfanilic acid has been used instead of tribromobenzoic acid in Lund and Bjerrum's method. A solution of 15g of magnesium in 500mL of methanol has been heated under reflux, under nitrogen, with hydroquinone (30g), before degassing and distilling the methanol, which was subsequently stored with magnesium (2g) and hydroquinone (4g per 100mL). Refluxing for about 12hours removes the bulk of the formaldehyde from methanol: further purification has been obtained by subsequent distillation, refluxing for 12hours with dinitrophenylhydrazine (5g) and H2SO4 (2g/L), and again fractionally distilling. [Beilstein 1 IV 1227.]

Incompatibilities

Methanol reacts violently with strong oxidizers, causing a fire and explosion hazard.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration

Check Digit Verification of cas no

The CAS Registry Mumber 67-56-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 7 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 67-56:
(4*6)+(3*7)+(2*5)+(1*6)=61
61 % 10 = 1
So 67-56-1 is a valid CAS Registry Number.
InChI:InChI=1/CH4O.H2O/c1-2;/h2H,1H3;1H2

67-56-1 Well-known Company Product Price

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  • TCI America

  • (M0097)  Methanol [for Spectrophotometry]  >99.8%(GC)

  • 67-56-1

  • 500mL

  • 265.00CNY

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  • Alfa Aesar

  • (31721)  Methanol, ACS, absolute, low acetone, 99.8+%   

  • 67-56-1

  • 500ml

  • 190.0CNY

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  • Alfa Aesar

  • (31721)  Methanol, ACS, absolute, low acetone, 99.8+%   

  • 67-56-1

  • 1L

  • 276.0CNY

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  • Alfa Aesar

  • (31721)  Methanol, ACS, absolute, low acetone, 99.8+%   

  • 67-56-1

  • 4L

  • 794.0CNY

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  • Alfa Aesar

  • (31721)  Methanol, ACS, absolute, low acetone, 99.8+%   

  • 67-56-1

  • *4x1L

  • 912.0CNY

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  • Alfa Aesar

  • (41467)  Methanol, anhydrous, 99.9%   

  • 67-56-1

  • 250ml

  • 239.0CNY

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  • Alfa Aesar

  • (41467)  Methanol, anhydrous, 99.9%   

  • 67-56-1

  • 1L

  • 403.0CNY

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  • Alfa Aesar

  • (41467)  Methanol, anhydrous, 99.9%   

  • 67-56-1

  • 4L

  • 824.0CNY

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  • Alfa Aesar

  • (41838)  Methanol, anhydrous, 99.9%, packaged under Argon in resealable ChemSeal? bottles   

  • 67-56-1

  • 250ml

  • 288.0CNY

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  • Alfa Aesar

  • (41838)  Methanol, anhydrous, 99.9%, packaged under Argon in resealable ChemSeal? bottles   

  • 67-56-1

  • 1L

  • 485.0CNY

  • Detail
  • Alfa Aesar

  • (40980)  Methanol, Environmental Grade, 99.8+%   

  • 67-56-1

  • 1L

  • 123.0CNY

  • Detail
  • Alfa Aesar

  • (40980)  Methanol, Environmental Grade, 99.8+%   

  • 67-56-1

  • 4L

  • 421.0CNY

  • Detail

67-56-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name methanol

1.2 Other means of identification

Product number -
Other names methyl alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Methanol is primarily used as an industrial solvent for inks, resins, adhesives, and dyes. It is also used as a solvent in the manufacture of cholesterol, streptomycin, vitamins, hormones, and other pharmaceuticals. (-) Methanol is also used as an antifreeze for automotive radiators, an ingredient of gasoline (as an antifreezing agent and octane booster), and as fuel for picnic stoves. Methanol is also an ingredient in paint and varnish removers. (-) Methanol is also used as an alternative motor fuel.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:67-56-1 SDS

67-56-1Synthetic route

formic acid
64-18-6

formic acid

methanol
67-56-1

methanol

Conditions
ConditionsYield
With water In aq. phosphate buffer at 20℃; for 1h; pH=7.4; Catalytic behavior; Reagent/catalyst; Electrolysis; Inert atmosphere; Enzymatic reaction;100%
With cobalt(III) acetylacetonate; hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran; ethanol at 100℃; under 52505.3 Torr; for 24h; Autoclave; Inert atmosphere;59%
With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride In ethanol; toluene at 180℃; under 7500.75 - 45004.5 Torr; for 18h; Autoclave;31%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

A

methanol
67-56-1

methanol

B

Velate 368
5444-75-7

Velate 368

Conditions
ConditionsYield
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 8h; Product distribution; Ambient temperature;A n/a
B 100%
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 8h; Ambient temperature;A n/a
B 100%
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

A

methanol
67-56-1

methanol

B

2-ethylhexyl methyl terephthalate
63468-13-3

2-ethylhexyl methyl terephthalate

Conditions
ConditionsYield
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 24h; Product distribution; Ambient temperature;A n/a
B 100%
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 24h; Ambient temperature;A n/a
B 100%
carbon dioxide
124-38-9

carbon dioxide

methanol
67-56-1

methanol

Conditions
ConditionsYield
With D-glucose; NADH In aq. buffer for 2h; pH=6.85; Catalytic behavior; Solvent; Concentration; pH-value; Ionic liquid; Enzymatic reaction;100%
With carbon monoxide; water; hydrogen at 35 - 250℃; under 825.083 - 75007.5 Torr; Temperature; Pressure; Large scale;99.99%
With dimethylsulfide borane complex; C24H18BO2P In benzene-d6 at 70℃; under 1520.1 Torr; for 1h; Reagent/catalyst; Inert atmosphere;95%
dimethyl(p-nitrophenyl)sulfonium perchlorate
29843-53-6

dimethyl(p-nitrophenyl)sulfonium perchlorate

A

methanol
67-56-1

methanol

B

1-methylthio-4-nitro-benzene
701-57-5

1-methylthio-4-nitro-benzene

Conditions
ConditionsYield
With water at 80℃; Rate constant; other temp.;A n/a
B 100%
2-methoxy-2-methyl nonane
78371-05-8

2-methoxy-2-methyl nonane

A

methanol
67-56-1

methanol

B

2-Iodo-2-methyl-nonane
78371-08-1

2-Iodo-2-methyl-nonane

Conditions
ConditionsYield
With Methyltrichlorosilane; sodium iodide In acetonitrile at 25℃; for 6h;A n/a
B 100%
1-(2-Adamantylidene)-1-methoxy-1-phenylmethane
113849-79-9

1-(2-Adamantylidene)-1-methoxy-1-phenylmethane

A

methanol
67-56-1

methanol

B

adamantan-2-yl(phenyl)methanone
68157-27-7

adamantan-2-yl(phenyl)methanone

Conditions
ConditionsYield
With tris-p-bromophenyl ammoniumyl hexachloroantimonate In dichloromethane for 3h;A n/a
B 100%
acetic acid 4-[2-(4-acetoxy-phenyl)-1,2-dimethoxy-acenaphthen-1-yl]-phenyl ester

acetic acid 4-[2-(4-acetoxy-phenyl)-1,2-dimethoxy-acenaphthen-1-yl]-phenyl ester

A

methanol
67-56-1

methanol

B

2,2-bis-(4-acetoxy-phenyl)-acenaphthen-1-one

2,2-bis-(4-acetoxy-phenyl)-acenaphthen-1-one

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 0.5h; pinacol rearrangement;A n/a
B 100%
polyester

polyester

A

methanol
67-56-1

methanol

B

polyester

polyester

Conditions
ConditionsYield
With trifluoroacetic acid In benzene at 25℃; for 0.5h; pinacol rearrangement;A n/a
B 100%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

3-Phenylpropenol
104-54-1

3-Phenylpropenol

A

methanol
67-56-1

methanol

B

cinnamyl benzoate
5320-75-2

cinnamyl benzoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
ethanol
64-17-5

ethanol

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

A

methanol
67-56-1

methanol

B

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

A

methanol
67-56-1

methanol

B

3-phenyl-2-propenyl benzenepropanoate
140671-25-6, 28048-98-8

3-phenyl-2-propenyl benzenepropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

8-(tert-butyldimethylsiloxy)octan-1-ol
91898-32-7

8-(tert-butyldimethylsiloxy)octan-1-ol

A

methanol
67-56-1

methanol

B

8-(tert-butyldimethylsilyloxy)octyl 3-phenylpropanoate

8-(tert-butyldimethylsilyloxy)octyl 3-phenylpropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
methanesulfonic acid
75-75-2

methanesulfonic acid

methanol
67-56-1

methanol

Conditions
ConditionsYield
With zeolite beads at 120 - 385℃; Product distribution / selectivity;100%
Rosin dimer (Dymerex)

Rosin dimer (Dymerex)

Silres SY231

Silres SY231

A

methanol
67-56-1

methanol

B

rosin modified silicone silyl ester

rosin modified silicone silyl ester

Conditions
ConditionsYield
tetrabutyl ammonium fluoride In n-heptane at 100 - 114℃; Conversion of starting material;A 100%
B 100%
tetrabutoxytitanium In n-heptane at 100 - 120℃; Conversion of starting material;A 100%
B 100%
lithium hydroxide In n-heptane at 100 - 120℃; Conversion of starting material;A 100%
B 100%
lithium stearate In n-heptane at 100 - 120℃; Conversion of starting material;A 100%
B 100%
2-benzoyloxyacetaldehyde dimethyl acetal
59708-43-9

2-benzoyloxyacetaldehyde dimethyl acetal

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

A

methanol
67-56-1

methanol

B

2-[(phenylcarbonyloxy)methyl]-1,3-oxathiolane
143338-44-7

2-[(phenylcarbonyloxy)methyl]-1,3-oxathiolane

Conditions
ConditionsYield
toluene-4-sulfonic acid In toluene Heating;A n/a
B 100%
tris(methyloxycarbonylmethyl)methane
57056-38-9

tris(methyloxycarbonylmethyl)methane

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

A

methanol
67-56-1

methanol

B

tris(methyloxycarbonylmethyl)methane
488706-18-9

tris(methyloxycarbonylmethyl)methane

Conditions
ConditionsYield
at 120℃; for 24h;A n/a
B 100%
2,6-di-tert-butyl-4-methylpyridine
38222-83-2

2,6-di-tert-butyl-4-methylpyridine

methyltriphenylbismuthonium tetrafluoroborate
278172-59-1

methyltriphenylbismuthonium tetrafluoroborate

A

methanol
67-56-1

methanol

B

Dimethyl ether
115-10-6

Dimethyl ether

C

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate
160142-36-9

2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate

D

triphenylbismuthane
603-33-8

triphenylbismuthane

Conditions
ConditionsYield
With H2O In chloroform-d1 water was added to mixt. (Ph3BiMe)(BF4) and 2,6-di-tert-butyl-4-methylpyridine in CDCl3 and mixt. was allowed to stand at room temp. for 33 h; detn. by NMR;A 30%
B 16%
C 100%
D 100%
sodium tetramethoxyborate
18024-69-6

sodium tetramethoxyborate

methanol
67-56-1

methanol

Conditions
ConditionsYield
With Glauber's salt for 0.166667h; Ball milling; neat (no solvent);100%
glycerol
56-81-5

glycerol

methanol
67-56-1

methanol

Conditions
ConditionsYield
With hydrogen; 10%Ru/C In water at 100℃; under 15001.5 Torr; for 2h; Product distribution / selectivity; Autoclave;100%
With magnesium oxide In water at 250℃; for 3h; Inert atmosphere;
With magnesium oxide In water for 3h; Reagent/catalyst; Inert atmosphere;
With Ag/CaO-SiO2 Reagent/catalyst; Inert atmosphere;
1,3-bis(4-hydroxybutyl)tetramethyldisiloxane
5931-17-9

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane

dimethoxy(methyl)phenylsilane
3027-21-2

dimethoxy(methyl)phenylsilane

A

methanol
67-56-1

methanol

B

hydroxybutyl-terminated polymethylsiloxane with fifty percent phenyl content

hydroxybutyl-terminated polymethylsiloxane with fifty percent phenyl content

Conditions
ConditionsYield
With hydrogenchloride In water for 4.5h; Heating / reflux;A n/a
B 100%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

A

methanol
67-56-1

methanol

B

ethylene glycol
107-21-1

ethylene glycol

Conditions
ConditionsYield
With 1,1′-(pyridine-2,6-diylbis(methylene))bis(3-butylimidazolium) dibromide; carbonylchlorohydridobis(tricyclohexylphosphine)ruthenium(II); potassium tert-butylate; hydrogen In 1,4-dioxane at 130℃; under 37503.8 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Autoclave;A 39%
B 100%
With hydrogen In 1,4-dioxane at 250℃; under 30003 Torr; for 4h; Temperature; Solvent; Reagent/catalyst; Flow reactor;A 93%
B 99%
With C24H38Cl2N3PRu; hydrogen; sodium methylate In tetrahydrofuran at 25℃; under 38002.6 Torr; for 16h; Autoclave;A 99 %Chromat.
B 95%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

methanol
67-56-1

methanol

Conditions
ConditionsYield
With potassium phosphate; carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); hydrogen In tetrahydrofuran at 155℃; under 37503.8 Torr; for 18h; Catalytic behavior; Inert atmosphere; Sealed tube;100%
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 130℃; under 37503.8 Torr; for 3h; Catalytic behavior; Temperature; Pressure;> 99 %Spectr.
With C24H38Cl2N3PRu; potassium tert-butylate; hydrogen In isopropyl alcohol at 110℃; under 30402 Torr; for 30h; Temperature; Autoclave; Glovebox;
9-methoxy-9-BBN
38050-71-4

9-methoxy-9-BBN

methanol
67-56-1

methanol

Conditions
ConditionsYield
With water at 20℃; for 0.5h;100%
With water In tetrahydrofuran at 20℃; for 1h;96%
Methyl formate
107-31-3

Methyl formate

dimethyl amine
124-40-3

dimethyl amine

A

methanol
67-56-1

methanol

B

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
under 2327.23 Torr; Industry scale;A n/a
B 99.97%
methane
34557-54-5

methane

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

A

methanol
67-56-1

methanol

B

formaldehyd
50-00-0

formaldehyd

C

carbon dioxide
124-38-9

carbon dioxide

D

carbon monoxide
201230-82-2

carbon monoxide

E

nitrogen
7727-37-9

nitrogen

Conditions
ConditionsYield
In neat (no solvent) Kinetics; Oxidation of CH4 by N2O in presence of catalyst (773 K): deposited Cu(2+) on carbon;;A 0.2%
B 0.3%
C 99.5%
D 0%
E n/a
In neat (no solvent) Kinetics; byproducts: C2H5OH (small quantity); oxidation of CH4 by N2O in presence of catalyst (773 K): deposited Ti(4+) on carbon;;A 13.8%
B 0%
C 86.2%
D 0%
E n/a
In neat (no solvent) Kinetics; Oxidation of CH4 by N2O in presence of catalyst (773 K): deposited Co(2+) on carbon;;A 0%
B 0%
C 75%
D 25%
E n/a
Methyl formate
107-31-3

Methyl formate

methanol
67-56-1

methanol

Conditions
ConditionsYield
With C21H37N2OPRu; hydrogen In 1,4-dioxane at 145℃; under 6840.46 Torr; for 36h;99%
dodecacarbonyl-triangulo-triruthenium; P(C4H9)3 In pyridine at 180℃; for 8h;40%
dodecacarbonyl-triangulo-triruthenium; P(C4H9)3 In pyridine at 180℃; for 8h; Product distribution; catalytic decarbonylation of some alkyl formates.;40%
5-methoxy-thianthrenium perchlorate

5-methoxy-thianthrenium perchlorate

A

methanol
67-56-1

methanol

B

thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

C

Thianthrene
92-85-3

Thianthrene

Conditions
ConditionsYield
With sodium thiophenolate; thiophenol In acetonitrile for 2h; Product distribution; Further Variations:; Solvents; Substitution; elimination;A 98%
B 1.7%
C 99%
morpholine
110-91-8

morpholine

methanol
67-56-1

methanol

4-methyl-morpholine
109-02-4

4-methyl-morpholine

Conditions
ConditionsYield
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 100℃;100%
With [RhCl2(p-cymene)]2; bis[2-(diphenylphosphino)phenyl] ether In toluene at 250℃; under 37503.8 Torr; Flow reactor;93%
With Cu1-Mo1/TiO2 In neat liquid at 20℃; for 21h; Catalytic behavior; Inert atmosphere; UV-irradiation;82%
epoxybutene
930-22-3

epoxybutene

methanol
67-56-1

methanol

2-(R)-2-Methoxybut-3-en-1-ol
18231-00-0

2-(R)-2-Methoxybut-3-en-1-ol

Conditions
ConditionsYield
With aluminium(III) triflate at 100℃; for 1h; regioselective reaction;100%
Stage #1: epoxybutene; methanol at 0℃; for 0.5h;
Stage #2: With sulfuric acid at 0 - 20℃; for 3h;
25%
With boron trifluoride diethyl etherate
2,2'-oxybis-acetic acid
110-99-6

2,2'-oxybis-acetic acid

methanol
67-56-1

methanol

dimethyl diglycolate
7040-23-5

dimethyl diglycolate

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃;100%
Stage #1: 2,2'-oxybis-acetic acid With thionyl chloride at 20℃; for 8h;
Stage #2: methanol
98%
With sulfuric acid for 24h; Heating;90%
4-chlorophenylacetic Acid
1878-66-6

4-chlorophenylacetic Acid

methanol
67-56-1

methanol

(4-chloro-phenyl)-acetic acid methyl ester
52449-43-1

(4-chloro-phenyl)-acetic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;100%
With monoammonium 12-tungstophosphate for 12h; Heating;98%
With sulfuric acid at 0 - 5℃; for 4.16667h; Reflux;98%
succinic acid anhydride
108-30-5

succinic acid anhydride

methanol
67-56-1

methanol

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

Conditions
ConditionsYield
at 20℃;100%
at 64 - 68℃; for 3.8h;98.5%
at 70℃; for 2h;98%
1H-pyrrole-3-carboxylic acid
931-03-3

1H-pyrrole-3-carboxylic acid

methanol
67-56-1

methanol

methyl 1H-pyrrole-3-carboxylate
2703-17-5

methyl 1H-pyrrole-3-carboxylate

Conditions
ConditionsYield
With hydrogenchloride at 80℃; for 20h; Inert atmosphere;100%
With hydrogenchloride In water at 0℃; Reflux;83%
With hydrogenchloride at 0 - 20℃; Reflux;83%
methanol
67-56-1

methanol

lauric acid
143-07-7

lauric acid

methyl n-dodecanoate
111-82-0

methyl n-dodecanoate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With ethenetetracarbonitrile for 48h; Ambient temperature;99%
polyaniline hydrocloride at 70℃; for 24h;99%
methanol
67-56-1

methanol

phenylacetic acid
103-82-2

phenylacetic acid

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;100%
With sulfuric acid for 4h; Reflux;100%
With sulfuric acid Heating;99%
methanol
67-56-1

methanol

o-Coumaric acid
614-60-8

o-Coumaric acid

methyl 2-hydroxycinnamate
6236-69-7

methyl 2-hydroxycinnamate

Conditions
ConditionsYield
With chloro-trimethyl-silane at 20℃;100%
With chloro-trimethyl-silane at 0 - 20℃;100%
With chloro-trimethyl-silane for 16h; Reflux;97%
methanol
67-56-1

methanol

azelaic acid
123-99-9

azelaic acid

Dimethyl azelate
1732-10-1

Dimethyl azelate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid In dichloromethane Dean-Stark; Heating;95%
With sulfuric acid80%
methanol
67-56-1

methanol

2'-chloro-benzeneacetic acid
2444-36-2

2'-chloro-benzeneacetic acid

methyl (2-chlorophenyl)acetate
57486-68-7

methyl (2-chlorophenyl)acetate

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;100%
With ammonium cerium(IV) nitrate at 20℃; for 12h;99%
sulfuric acid for 16h; Heating / reflux;97.5%
methanol
67-56-1

methanol

(3,4-Dimethoxyphenyl)acetic acid
93-40-3

(3,4-Dimethoxyphenyl)acetic acid

methyl (3,4-dimethoxyphenyl)acetate
15964-79-1

methyl (3,4-dimethoxyphenyl)acetate

Conditions
ConditionsYield
With sulfuric acid Heating;100%
With thionyl chloride for 18h;99%
With sulfuric acid for 0.5h; Reflux;99%
methanol
67-56-1

methanol

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Dimethyl glutarate
1119-40-0

Dimethyl glutarate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With phosphorus trichloride Cooling;92%
With hydrogenchloride
methanol
67-56-1

methanol

Adipic acid
124-04-9

Adipic acid

hexanedioic acid dimethyl ester
627-93-0

hexanedioic acid dimethyl ester

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
at 130℃; for 4h; Temperature;99.81%
With aluminum(III) sulphate octadecahydrate at 110℃; for 0.166667h; Sealed tube; Microwave irradiation;97.7%
methanol
67-56-1

methanol

heptanedioic acid
111-16-0

heptanedioic acid

dimethyl 1,7-heptanedioate
1732-08-7

dimethyl 1,7-heptanedioate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid Heating;98%
With toluene-4-sulfonic acid for 7h; Reflux; Large scale;98.08%
methanol
67-56-1

methanol

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

dimethyl sebacate
106-79-6

dimethyl sebacate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With modification of hypercrosslinked supermicroporous polymer (HMP-1) via sulfonation (HMP-1-SO3H) at 24.84℃; for 12h; Green chemistry;97%
With Fe3O4 immobilized thiol functionalized mesoporous silica at 24.84℃; for 20h;96%
methanol
67-56-1

methanol

Tiglic acid
80-59-1

Tiglic acid

methyl (E)-2-methyl-2-butenoate
6622-76-0

methyl (E)-2-methyl-2-butenoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 3h; Heating;100%
With sulfuric acid rt. then reflux;73.8%
With sulfuric acid for 24h; Heating;70%
methanol
67-56-1

methanol

isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

methyl chlorosulfonylcarbamate
36914-92-8

methyl chlorosulfonylcarbamate

Conditions
ConditionsYield
In dichloromethane for 1h;100%
In dichloromethane at 0℃; for 0.25h;100%
In benzene99%
methanol
67-56-1

methanol

11-hydroxyundecanoic acid
3669-80-5

11-hydroxyundecanoic acid

methyl 11-hydroxyundecanoate
24724-07-0

methyl 11-hydroxyundecanoate

Conditions
ConditionsYield
With hydrogenchloride Heating;100%
With sulfuric acid for 24h; Heating;90%
With acetyl chloride at 40℃; for 3.5h;53%
methanol
67-56-1

methanol

6-oxoheptanoic acid
3128-07-2

6-oxoheptanoic acid

methyl 6-oxoheptanoate
2046-21-1

methyl 6-oxoheptanoate

Conditions
ConditionsYield
iron(III) chloride100%
With sulfuric acid In 1,2-dichloro-ethane Fisher esterification;100%
With sulfuric acid In 1,2-dichloro-ethane for 12h; Heating;100%
methanol
67-56-1

methanol

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

benzhydryl methyl ether
1016-09-7

benzhydryl methyl ether

Conditions
ConditionsYield
With hydrogenchloride In water for 5h; Temperature; Time; Reflux; chemoselective reaction;100%
With sulfuric acid for 16h; Kinetics; Reflux;97%
With sulfuric acid for 2h; Reflux;97%
methanol
67-56-1

methanol

4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

Methyl 4-hydroxyphenylacetate
14199-15-6

Methyl 4-hydroxyphenylacetate

Conditions
ConditionsYield
With sulfuric acid Heating;100%
With sulfuric acid for 8h; Heating;100%
With sulfuric acid100%
methanol
67-56-1

methanol

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

3,4-dihydroxybenzoic acid methyl ester
2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride Heating;100%
With sulfuric acid for 8h; Reflux;100%
With sulfuric acid under 760.051 Torr; Reflux;100%
methanol
67-56-1

methanol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With Dowex 50 W x 8200-400 Heating;100%
With thionyl chloride Ambient temperature;100%
With sulfuric acid at 0℃; for 12h; Darkness; Reflux;99%
methanol
67-56-1

methanol

L-alanin
56-41-7

L-alanin

L-Alanine methyl ester
10065-72-2

L-Alanine methyl ester

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 48h; Reflux;100%
Stage #1: methanol With thionyl chloride at 0℃; for 0.166667h;
Stage #2: L-alanin at 20℃; for 12h;
97%
With thionyl chloride at 8 - 10℃; Reflux;96.68%
methanol
67-56-1

methanol

rac-Ala-OH
302-72-7

rac-Ala-OH

methyl 2-aminopropanoate monohydrochloride
13515-97-4

methyl 2-aminopropanoate monohydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 17h; Inert atmosphere;100%
With thionyl chloride at -20 - 20℃; for 17h; Inert atmosphere;100%
With chloro-trimethyl-silane at 20℃; for 12h;97%
methanol
67-56-1

methanol

L-valine
72-18-4

L-valine

L-valine methylester hydrochloride
6306-52-1

L-valine methylester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃;100%
With thionyl chloride at 20℃; Cooling with ice; Inert atmosphere;100%
Stage #1: L-valine With thionyl chloride at 0℃; for 4.16667h; Reflux;
Stage #2: methanol
100%
methanol
67-56-1

methanol

L-leucine
61-90-5

L-leucine

(S)-Leu-OMe
2666-93-5

(S)-Leu-OMe

Conditions
ConditionsYield
With thionyl chloride100%
With thionyl chloride100%
With thionyl chloride at 0 - 20℃;94%
methanol
67-56-1

methanol

LEUCINE
328-39-2

LEUCINE

DL-leucine methyl ester
18869-43-7

DL-leucine methyl ester

Conditions
ConditionsYield
With thionyl chloride for 3h; Heating;100%
Stage #1: methanol; LEUCINE With hydrogenchloride at 20℃; Reflux;
Stage #2: With sodium hydrogencarbonate In water pH=7;
96%
With hydrogenchloride leucine DL-methyl ester;
methanol
67-56-1

methanol

L-isoleucine
73-32-5

L-isoleucine

L-isoleucine methyl ester
2577-46-0

L-isoleucine methyl ester

Conditions
ConditionsYield
Stage #1: methanol With thionyl chloride at -15 - 0℃; for 1h;
Stage #2: L-isoleucine for 3h; Reflux;
100%
With hydrogenchloride96%
With thionyl chloride at 0℃; for 12h; Reflux;95%

67-56-1Relevant articles and documents

C-C Bond Cleavage of Acetonitrile by a Dinuclear Copper(II) Cryptate

Lu, Tongbu,Zhuang, Xiaomei,Li, Yanwu,Chen, Shi

, p. 4760 - 4761 (2004)

The dinuclear copper(II) cryptate [Cu2L](ClO4)4 (1) cleaves the C?C bond of acetonitrile at room temperature to produce a cyanide bridged complex of [Cu2L(CN)](ClO4)3·2CH3CN·4H2O (2). The cleavage mechanism is presented on the basis of the results of the crystal structure of 2, electronic absorption spectra, ESI-MS spectroscopy, and GC spectra of 1, respectively. Copyright

Kassel

, p. 493 (1936)

Photochemical and enzymatic synthesis of methanol from HCO3 - with dehydrogenases and zinc porphyrin

Amao, Yutaka,Watanabe, Tomoe

, p. 1544 - 1545 (2004)

Photochemical and enzymatic methanol synthesis from HCO3 - with formate dehydrogenase (FDH), aldehyde dehydrogenase (AldDH), and alcohol dehydrogenase (ADH) via the photoreduction of MV2+ using ZnTPPS photosensitization wa

Catalytic Activity of Nanosized CuO-ZnO Supported on Titanium Chips in Hydrogenation of Carbon Dioxide to Methyl Alcohol

Ahn, Ho-Geun,Lee, Hwan-Gyu,Chung, Min-Chul,Park, Kwon-Pil,Kim, Ki-Joong,Kang, Byeong-Mo,Jeong, Woon-Jo,Jung, Sang-Chul,Lee, Do-Jin

, p. 2024 - 2027 (2016)

In this study, titanium chips (TC) generated from industrial facilities was utilized as TiO2 support for hydrogenation of carbon dioxide (CO2) to methyl alcohol (CH3OH) over Cu-based catalysts. Nanosized CuO and ZnO catalysts were deposited on TiO2 support using a co-precipitation (CP) method (CuO-ZnO/TiO2), where the thermal treatment of TC and the particle size of TiO2 are optimized on CO2 conversion under different reaction temperature and contact time. Direct hydrogenation of CO2 to CH3OH over CuO-ZnO/TiO2 catalysts was achieved and the maximum selectivity (22%) and yield (18.2%) of CH3OH were obtained in the range of reaction temperature 210~240 °C under the 30 bar. The selectivity was readily increased by increasing the flow rate, which does not affect much to the CO2 conversion and CH3OH yield.

Comparative Study of Diverse Copper Zeolites for the Conversion of Methane into Methanol

Park, Min Bum,Ahn, Sang Hyun,Mansouri, Ali,Ranocchiari, Marco,van Bokhoven, Jeroen A.

, p. 3705 - 3713 (2017)

The characterization and reactive properties of copper zeolites with twelve framework topologies (MOR, EON, MAZ, MEI, BPH, FAU, LTL, MFI, HEU, FER, SZR, and CHA) are compared in the stepwise partial oxidation of methane into methanol. Cu2+ ion-exchanged zeolite omega, a MAZ-type material, reveals the highest yield (86 μmol g(cat.)?1) among these materials after high-temperature activation and liquid methanol extraction. The high yield is ascribed to the relatively high density of copper–oxo active species, which form in its three-dimensional 8-membered (MB) ring channels. In situ UV/Vis studies show that diverse copper species form in different zeolites after high-temperature activation, suggesting that there are no universally active species. Nonetheless, there are some dominant factors required for achieving high methanol yields: 1) highly dispersed copper–oxo species; 2) large amount of exchanged copper in small-pore zeolites; 3) moderately high temperature of activation; and 4) use of proton form zeolite precursors. Cu-omega and Cu-mordenite, with the proton form of mordenite as the precursor, yield methanol after activation in oxygen and reaction with methane at only 200 °C, that is, under isothermal conditions.

Spontaneous hydrolysis of ionized phosphate monoesters and diesters and the proficiencies of phosphatases and phosphodiesterases as catalysts

Wolfenden, Richard,Ridgway, Caroline,Young, Gregory

, p. 833 - 834 (1998)

-

Facile synthesis of ZnO particles: Via benzene-assisted co-solvothermal method with different alcohols and its application

Maneechakr, Panya,Karnjanakom, Surachai,Samerjit, Jittima

, p. 73947 - 73952 (2016)

In this study, ZnO particles with different morphologies were synthesized by a novel co-solvothermal method using benzene. The prepared samples were characterized by Brunauer-Emmett-Teller (BET) measurements, X-ray diffractometry (XRD), scanning electron microscopy coupled with an energy dispersive X-ray detector (SEM-EDX), high-resolution transmission electron microscopy (HRTEM), X-ray photoelectron spectrometry (XPS), and H2-temperature programmed reduction (H2-TPR). The results showed that the molecular sizes and carbon numbers of the alcohols used in the reaction and the addition of benzene had a great effect on the morphologies, textural properties, and crystalline structures of the material products in our reaction system. Different ZnO morphologies, such as spherical coral-like, carnation-like, rose-like, and plate-like structures, were obtained using methanol, ethanol, propanol, and butanol, respectively. Moreover, Cu particles loaded on ZnO with different morphologies were also investigated for the hydrogenation of CO2 to CH3OH. High catalytic activity and selectivity (82.8%) for CH3OH formation were obtained using ZnO prepared from methanol with Cu doping (Cu/ZnO-Me).

Efficient ionic liquid-based platform for multi-enzymatic conversion of carbon dioxide to methanol

Zhang, Zhibo,Muschiol, Jan,Huang, Yuhong,Sigurdardóttir, Sigyn Bj?rk,Von Solms, Nicolas,Daugaard, Anders E.,Wei, Jiang,Luo, Jianquan,Xu, Bao-Hua,Zhang, Suojiang,Pinelo, Manuel

, p. 4339 - 4348 (2018)

Low yields commonly obtained during enzymatic conversion of CO2 to methanol are attributed to low CO2 solubility in water. In this study, four selected ionic liquids with high CO2 solubility were separately added to the multi-enzyme reaction mixture and the yields were compared to the pure aqueous system (control). In an aqueous 20% [CH][Glu] system, yield increased ca. 3.5-fold compared to the control (ca. 5-fold if NADH regeneration was incorporated). Molecular dynamics simulation revealed that CO2 remains for longer in a productive conformation in the enzyme in the presence of [CH][Glu], which explains the marked increase of yield that was also confirmed by isothermal titration calorimetry-lower energy (ΔG) binding of CO2 to FDH. The results suggest that the accessibility of CO2 to the enzyme active site depends on the absence/presence and nature of the ionic liquid, and that the enzyme conformation determines CO2 retention and hence final conversion.

Comparative study of hydrotalcite-derived supported Pd2Ga and PdZn intermetallic nanoparticles as methanol synthesis and methanol steam reforming catalysts

Ota, Antje,Kunkes, Edward L.,Kasatkin, Igor,Groppo, Elena,Ferri, Davide,Poceiro, Beatriz,Navarro Yerga, Rufino M.,Behrens, Malte

, p. 27 - 38 (2012)

An effective and versatile synthetic approach to produce well-dispersed supported intermetallic nanoparticles is presented that allows a comparative study of the catalytic properties of different intermetallic phases while minimizing the influence of differences in preparation history. Supported PdZn, Pd2Ga, and Pd catalysts were synthesized by reductive decomposition of ternary Hydrotalcite-like compounds obtained by co-precipitation from aqueous solutions. The precursors and resulting catalysts were characterized by HRTEM, XRD, XAS, and CO-IR spectroscopy. The Pd2+ cations were found to be at least partially incorporated into the cationic slabs of the precursor. Full incorporation was confirmed for the PdZnAl-Hydrotalcite-like precursor. After reduction of Ga- and Zn-containing precursors, the intermetallic compounds Pd2Ga and PdZn were present in the form of nanoparticles with an average diameter of 6 nm or less. Tests of catalytic performance in methanol steam reforming and methanol synthesis from CO2 have shown that the presence of Zn and Ga improves the selectivity to CO2 and methanol, respectively. The catalysts containing intermetallic compounds were 100 and 200 times, respectively, more active for methanol synthesis than the monometallic Pd catalyst. The beneficial effect of Ga in the active phase was found to be more pronounced in methanol synthesis compared with steam reforming of methanol, which is likely related to insufficient stability of the reduced Ga species in the more oxidizing feed of the latter reaction. Although the intermetallic catalysts were in general less active than a Cu-/ZnO-based material prepared by a similar procedure, the marked changes in Pd reactivity upon formation of intermetallic compounds and to study the tunability of Pd-based catalysts for different reactions.

Self-sufficient and exclusive oxygenation of methane and its source materials with oxygen to methanol via metgas using oxidative bi-reforming

Olah, George A.,Prakash, G. K. Surya,Goeppert, Alain,Czaun, Miklos,Mathew, Thomas

, p. 10030 - 10031 (2013)

A combination of complete methane combustion with oxygen of the air coupled with bi-reforming leads to the production of metgas (H2/CO in 2:1 mole ratio) for exclusive methanol synthesis. The newly developed oxidative bi-reforming allows direct oxygenation of methane to methanol in an overall economic and energetically efficient process, leaving very little, if any, carbon footprint or byproducts.

Spinel-Structured ZnCr2O4 with Excess Zn Is the Active ZnO/Cr2O3 Catalyst for High-Temperature Methanol Synthesis

Song, Huiqing,Laudenschleger, Daniel,Carey, John J.,Ruland, Holger,Nolan, Michael,Muhler, Martin

, p. 7610 - 7622 (2017)

A series of ZnO/Cr2O3 catalysts with different Zn:Cr ratios was prepared by coprecipitation at a constant pH of 7 and applied in methanol synthesis at 260-300 °C and 60 bar. The X-ray diffraction (XRD) results showed that the calcined catalysts with ratios from 65:35 to 55:45 consist of ZnCr2O4 spinel with a low degree of crystallinity. For catalysts with Zn:Cr ratios smaller than 1, the formation of chromates was observed in agreement with temperature-programmed reduction results. Raman and XRD results did not provide evidence for the presence of segregated ZnO, indicating the existence of Zn-rich nonstoichiometric Zn-Cr spinel in the calcined catalyst. The catalyst with Zn:Cr = 65:35 exhibits the best performance in methanol synthesis. The Zn:Cr ratio of this catalyst corresponds to that of the Zn4Cr2(OH)12CO3 precursor with hydrotalcite-like structure obtained by coprecipitation, which is converted during calcination into a nonstoichiometric Zn-Cr spinel with an optimum amount of oxygen vacancies resulting in high activity in methanol synthesis. Density functional theory calculations are used to examine the formation of oxygen vacancies and to measure the reducibility of the methanol synthesis catalysts. Doping Cr into bulk and the (10-10) surface of ZnO does not enhance the reducibility of ZnO, confirming that Cr:ZnO cannot be the active phase. The (100) surface of the ZnCr2O4 spinel has a favorable oxygen vacancy formation energy of 1.58 eV. Doping this surface with excess Zn charge-balanced by oxygen vacancies to give a 60% Zn content yields a catalyst composed of an amorphous ZnO layer supported on the spinel with high reducibility, confirming this as the active phase for the methanol synthesis catalyst.

Dodge

, p. 89 (1930)

A novel low-temperature methanol synthesis method from CO/H2/CO2 based on the synergistic effect between solid catalyst and homogeneous catalyst

Zhao, Tian-Sheng,Zhang, Kun,Chen, Xuri,Ma, Qingxiang,Tsubaki, Noritatsu

, p. 98 - 104 (2010)

The activity of a binary catalyst in alcoholic solvents for methanol synthesis from CO/H2/CO2 at low temperature was investigated in a concurrent synthesis course. Experiment results showed that the combination of homogeneous potassium formate catalyst and solid copper-magnesia catalyst enhanced the conversion of CO2-containing syngas to methanol at temperature of 423-443 K and pressure of 3-5 MPa. Under a contact time of 100 g h/mol, the maximum conversion of total carbon approached the reaction equilibrium and the selectivity of methanol was 99%. A reaction pathway involving esterification and hydrogenolysis of esters was postulated based on the integrative and separate activity tests, along with the structural characterization of the catalysts. Both potassium formate for the esterification as well as Cu/MgO for the hydrogenolysis were found to be crucial to this homogeneous and heterogeneous synergistically catalytic system. CO and H2 were involved in the recycling of potassium formate.

Continuous supercritical low-temperature methanol synthesis with n-butane as a supercritical fluid

Reubroycharoen, Prasert,Bao, Jun,Zhang, Yi,Tsubaki, Noritatsu

, p. 790 - 791 (2008)

A process of supercritical low-temperature methanol synthesis from syngas containing CO2 was carried out at 443 K and 60 bar. The 2-butanol and n-butane was used as catalytic solvent and supercritical medium, respectively. The results showed that the total carbon conversion, especially the CO 2 conversion of the methanol synthesis was increased significantly under the supercritical condition. Copyright

Molybdenum-Bismuth Bimetallic Chalcogenide Nanosheets for Highly Efficient Electrocatalytic Reduction of Carbon Dioxide to Methanol

Sun, Xiaofu,Zhu, Qinggong,Kang, Xinchen,Liu, Huizhen,Qian, Qingli,Zhang, Zhaofu,Han, Buxing

, p. 6771 - 6775 (2016)

Methanol is a very useful platform molecule and liquid fuel. Electrocatalytic reduction of CO2 to methanol is a promising route, which currently suffers from low efficiency and poor selectivity. Herein we report the first work to use a Mo-Bi bimetallic chalcogenide (BMC) as an electrocatalyst for CO2 reduction. By using the Mo-Bi BMC on carbon paper as the electrode and 1-butyl-3-methylimidazolium tetrafluoroborate in MeCN as the electrolyte, the Faradaic efficiency of methanol could reach 71.2 % with a current density of 12.1 mA cm-2, which is much higher than the best result reported to date. The superior performance of the electrode resulted from the excellent synergistic effect of Mo and Bi for producing methanol. The reaction mechanism was proposed and the reason for the synergistic effect of Mo and Bi was discussed on the basis of some control experiments. This work opens a way to produce methanol efficiently by electrochemical reduction of CO2.

Characterization of modified Fischer-Tropsch catalysts promoted with alkaline metals for higher alcohol synthesis

Cosultchi, Ana,Perez-Luna, Miguel,Morales-Serna, Jose Antonio,Salmon, Manuel

, p. 368 - 377 (2012)

Two series of Cu/Co/Cr modified Fischer-Tropsch catalyst promoted with Zn or Mn and an alkaline metal (Me: Li, Na, K, Rb, Cs) were prepared by co-precipitation method and tested for high alcohol synthesis (HAS) at one hour on-stream and at two temperatures, 300 and 350 °C. The results indicate that the best selectivity toward high alcohols depends on temperature and catalysts composition and is obtained as follows: a) at 300 °C over catalysts without Zn and containing K, Na and Rb; b) at 350 °C over catalysts without Zn and containing K; c) at 350 °C over catalysts containing Zn as well as Li and Cs.

ACID-CATALYZED HYDROLYSIS OF 2-METHOXYPROPENAL

Fedoronko, Michal,Petrusova, Maria,Tvaroska, Igor

, p. 85 - 94 (1983)

2-Methoxypropenal in acid media undergoes general acid-catalyzed hydrolysis with formation of 2-oxopropanal.The kinetics of this reaction were studied, the rate constants established, and a reaction mechanism is suggested.Hydrolysis of 2-methoxypropenal is governed by a mechanism of the vinyl ether type, and the presence of the aldehyde group causes a decrease in the reaction rate.The analogy of the acid-catalyzed hydrolysis of 2-methoxypropenal to that of a vinyl ether was shown by the solvent isotope-effect, kD/kH=0.41, and the value of the Broensted exponent, α=0.60.The activation parameters found and quantum-chemical calculations of charge distribution in 2-methoxypropenal and other model compounds were also utilized to explain the mechanism of the acid-catalyzed hydrolysis of the title compound.

Carbon Dioxide Conversion to Methanol over Size-Selected Cu4 Clusters at Low Pressures

Liu, Cong,Yang, Bing,Tyo, Eric,Seifert, Soenke,Debartolo, Janae,Von Issendorff, Bernd,Zapol, Peter,Vajda, Stefan,Curtiss, Larry A.

, p. 8676 - 8679 (2015)

The activation of CO2 and its hydrogenation to methanol are of much interest as a way to utilize captured CO2. Here, we investigate the use of size-selected Cu4 clusters supported on Al2O3 thin films for CO2 reduction in the presence of hydrogen. The catalytic activity was measured under near-atmospheric reaction conditions with a low CO2 partial pressure, and the oxidation state of the clusters was investigated by in situ grazing incidence X-ray absorption spectroscopy. The results indicate that size-selected Cu4 clusters are the most active low-pressure catalyst for catalytic CO2 conversion to CH3OH. Density functional theory calculations reveal that Cu4 clusters have a low activation barrier for conversion of CO2 to CH3OH. This study suggests that small Cu clusters may be excellent and efficient catalysts for the recycling of released CO2.

Selective Photoreduction of Carbon Dioxide to Methanol on Titanium Dioxide Photocatalysts in Propylene Carbonate Solution

Kuwabata, Susumu,Uchida, Hiroyuki,Ogawa, Akihiro,Hirao, Shigeki,Yoneyama, Hiroshi

, p. 829 - 830 (1995)

Methanol is selectively photosynthesised from carbon dioxide using TiO2 photocatalysts in propylene carbonate containing propan-2-ol as a hole scavenger.

Effect of Γ-alumina nanorods on CO hydrogenation to higher alcohols over lithium-promoted CuZn-based catalysts

Choi, SuMin,Kang, YoungJong,Kim, SangWoo

, p. 188 - 196 (2018)

To achieve high catalytic activities and long-term stability to produce higher alcohols via CO hydrogenation, the catalytic activities were tuned by controlling the loading amounts of γ-alumina nanorods and Al3+ ions added to modify Cu-Zn catalysts promoted with Li. The selectivity of higher alcohols and the CO conversion to higher alcohols over a Li-modified Cu0.45Zn0.45Al0.1 catalyst supported on 10% nanorods were 1.8 and 2.7 times higher than those with a Cu-Zn catalyst without nanorods and Al3+ ions, respectively. The introduction of the thermally and chemically stable γ-Al2O3 nanorod support and of Al3+ to the modified catalysts improves the catalytic activities by decreasing the crystalline size of CuO and increasing the total basicity. Along with the nanorods, a refractory CuAl2O4 formed by the thermal reaction of CuO and Al3+ enhances the long-term stability by increasing the resistance to sintering of the catalyst.

CO2 Conversion into Methanol Using Granular Silicon Carbide (α6H-SiC): A Comparative Evaluation of 355 nm Laser and Xenon Mercury Broad Band Radiation Sources

Gondal, Mohammed Ashraf,Ali, Mohammed Ashraf,Dastageer, Mohamed Abdulkader,Chang, Xiaofeng

, p. 108 - 117 (2013)

Granular silicon carbide (α6H-SiC) was investigated as a photo-reduction catalyst for CO2 conversion into methanol using a 355 nm laser from the third harmonic of pulsed Nd:YAG laser and 500 W collimated xenon mercury (XeHg) broad band lamp. The reaction cell was filled with distilled water, α6H-SiC granules and pressurized with CO2 gas at 50 psi. Maximum molar concentration of methanol achieved was 1.25 and 0.375 mmol/l and the photonic efficiencies of CO2 conversion into methanol achieved were 1.95 and 1.16 % using the laser and the XeHg lamp respectively. The selectivity of methanol produced using the laser irradiation was 100 % as compared to about 50 % with the XeHg lamp irradiation. The band gap energy of silicon carbide was estimated to be 3.17 eV and XRD demonstrated that it is a highly crystalline material. This study demonstrated that commercially available granular silicon carbide is a promising photo-reduction catalyst for CO 2 into methanol. Graphical Abstract: Gas Chromatograms of reaction products collected at 30-120 min irradiation in the presence of 355 nm laser having 40 mJ/pulse energy. The inset shows the comparison of retention time of GC peaks with the methanol standard and it is at 2.46 min.[Figure not available: see fulltext.]

Continuous precipitation of Cu/ZnO/Al2O3 catalysts for methanol synthesis in microstructured reactors with alternative precipitating agents

Simson, Georg,Prasetyo, Eko,Reiner, Stefanie,Hinrichsen, Olaf

, p. 1 - 12 (2013)

Ternary Cu/ZnO/Al2O3 catalyst systems were systematically prepared by innovative synthesis routes in microstructured synthesis setups, allowing to study different types of micromixers. The coprecipitation in the slit plate and valve-assisted mixers was operated continuously under exact control of pH, temperature, concentration and ageing time. Due to the enhanced surface to volume ratio in microstructured reactors, a precise temperature control and efficient mixing of the reactants are enabled. The precipitation was performed with sodium, ammonium and potassium carbonate as well as sodium hydroxide. To evaluate the potential of the novel synthesis routes, reference samples in a conventional batch process were prepared. The catalysts were synthesized according to the constant pH method with a molar ratio of 60:30:10 for copper, zinc and aluminum. The synthesis routes applied have a significant influence on the structures of hydroxycarbonate precursors and on the catalytic activity in methanol synthesis. XRD patterns of hydroxycarbonate precursors from the synthesis in micromixers, especially using ammonium carbonate as precipitating agent, display high crystallinity and sharp reflections of malachite and rosasite. Cu/ZnO/Al2O3 catalysts prepared in continuously operated micromixers in general show higher specific copper surface areas than catalysts prepared in conventional batch processes. The highest methanol productivity of all prepared catalyst systems was observed with the catalyst precipitated in the slit plate mixer with ammonium carbonate.

Stable amorphous georgeite as a precursor to a high-activity catalyst

Kondrat, Simon A.,Smith, Paul J.,Wells, Peter P.,Chater, Philip A.,Carter, James H.,Morgan, David J.,Fiordaliso, Elisabetta M.,Wagner, Jakob B.,Davies, Thomas E.,Lu, Li,Bartley, Jonathan K.,Taylor, Stuart H.,Spencer, Michael S.,Kiely, Christopher J.,Kelly, Gordon J.,Park, Colin W.,Rosseinsky, Matthew J.,Hutchings, Graham J.

, p. 83 - 87 (2016)

Copper and zinc form an important group of hydroxycarbonate minerals that include zincian malachite, aurichalcite, rosasite and the exceptionally rare and unstable - and hence little known and largely ignored - georgeite. The first three of these minerals are widely used as catalyst precursors for the industrially important methanol-synthesis and low-temperature water-gas shift (LTS) reactions, with the choice of precursor phase strongly influencing the activity of the final catalyst. The preferred phase is usually zincian malachite. This is prepared by a co-precipitation method that involves the transient formation of georgeite; with few exceptions it uses sodium carbonate as the carbonate source, but this also introduces sodium ions - a potential catalyst poison. Here we show that supercritical antisolvent (SAS) precipitation using carbon dioxide (refs 13, 14), a process that exploits the high diffusion rates and solvation power of supercritical carbon dioxide to rapidly expand and supersaturate solutions, can be used to prepare copper/zinc hydroxycarbonate precursors with low sodium content. These include stable georgeite, which we find to be a precursor to highly active methanol-synthesis and superior LTS catalysts. Our findings highlight the value of advanced synthesis methods in accessing unusual mineral phases, and show that there is room for exploring improvements to established industrial catalysts.

The partial oxidation of methane to methanol with nitrite and nitrate melts

Lee, Bor-Jih,Kitsukawa, Shigeo,Nakagawa, Hidemoto,Asakura, Shukuji,Fukuda, Kenzo

, p. 679 - 682 (1998)

The effect of reduced oxygen species on the partial oxidation of methane to methanol was examined with nitrite melts. The experimental results support the suggestion that the formation of methanol or C2 compounds depends on different reduced oxygen species, as observed in our previous work using nitrate melts. It has been suggested that the partial oxidation of methane proceeds to CH3OH or C2 compounds via parallel pathways. This suggestion was verified by increasing the oxygen concentration to carry out the partial oxidation of methane in 25 mol% NaNO3 - 75 mol% KNO3 melts. A methanol selectivity of 8.2% and a methanol yield of 0.43% were observed with CH4/O2 = 15/1 at 575 °C, whereas with CH4/O2 = 7/1 methanol selectivity and yield increased to 23.7% and 1.1%, respectively. The results further confirm the contribution of the superoxide ion O2- on methanol formation.

Carbon dioxide hydrogenation to methanol over Cu/ZrO2/CNTs: Effect of carbon surface chemistry

Wang, Guannan,Chen, Limin,Sun, Yuhai,Wu, Junliang,Fu, Mingli,Ye, Daiqi

, p. 45320 - 45330 (2015)

Methanol synthesis from CO2 hydrogenation in a fixed-bed plug flow reactor was investigated over Cu-ZrO2 catalysts supported on CNTs bearing various functional groups. The highest methanol activity (turnover frequency 1.61 × 10-2 s-1, space time yield 84.0 mg gcat-1 h-1) was obtained over the Cu/ZrO2/CNTs catalyst (CZ/CNT-3) with CNTs functionalized by nitrogen-containing groups and Cu loading only about 10.3 wt% under the reaction conditions of 260 °C, 3.0 MPa, V(H2):V(CO2):V(N2) = 69:23:8 and GHSV of 3600 h-1. The catalysts were fully characterized by N2 physisorption, X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD), H2-temperature-programmed reduction (H2-TPR) and temperature-programmed desorption of H2 (H2-TPD) techniques. The excellent performance of CZ/CNT-3 is attributed to the presence of nitrogen-containing groups on the CNTs surface, which increase the dispersion of copper oxides, promote their reduction, decreases the crystal size of Cu, and enhances H2 and CO2 adsorption capability, thus leading to good catalytic performance towards methanol synthesis. This journal is

Hydrogenation of Esters by Manganese Catalysts

Li, Fu,Li, Xiao-Gen,Xiao, Li-Jun,Xie, Jian-Hua,Xu, Yue,Zhou, Qi-Lin

, (2022/01/13)

The hydrogenation of esters catalyzed by a manganese complex of phosphine-aminopyridine ligand was developed. Using this protocol, a variety of (hetero)aromatic and aliphatic carboxylates including biomass-derived esters and lactones were hydrogenated to primary alcohols with 63–98% yields. The manganese catalyst was found to be active for the hydrogenation of methyl benzoate, providing benzyl alcohol with turnover numbers (TON) as high as 45,000. Investigation of catalyst intermediates indicated that the amido manganese complex was the active catalyst species for the reaction. (Figure presented.).

Binary Au–Cu Reaction Sites Decorated ZnO for Selective Methane Oxidation to C1 Oxygenates with Nearly 100% Selectivity at Room Temperature

Gong, Zhuyu,Liu, Huifen,Luo, Lei,Ma, Jiani,Tang, Junwang,Xing, Jialiang,Xu, Youxun

supporting information, p. 740 - 750 (2022/01/03)

Direct and efficient oxidation of methane to methanol and the related liquid oxygenates provides a promising pathway for sustainable chemical industry, while still remaining an ongoing challenge owing to the dilemma between methane activation and overoxidation. Here, ZnO with highly dispersed dual Au and Cu species as cocatalysts enables efficient and selective photocatalytic conversion of methane to methanol and one-carbon (C1) oxygenates using O2 as the oxidant operated at ambient temperature. The optimized AuCu–ZnO photocatalyst achieves up to 11225 μmol·g–1·h–1 of primary products (CH3OH and CH3OOH) and HCHO with a nearly 100% selectivity, resulting in a 14.1% apparent quantum yield at 365 nm, much higher than the previous best photocatalysts reported for methane conversion to oxygenates. In situ EPR and XPS disclose that Cu species serve as photoinduced electron mediators to promote O2 activation to ?OOH, and simultaneously that Au is an efficient hole acceptor to enhance H2O oxidation to ?OH, thus synergistically promoting charge separation and methane transformation. This work highlights the significances of co-modification with suitable dual cocatalysts on simultaneous regulation of activity and selectivity.

High catalytic methane oxidation activity of monocationic μ-nitrido-bridged iron phthalocyanine dimer with sixteen methyl groups

Kura, Jyunichi,Tanaka, Kentaro,Toyoda, Yuka,Yamada, Yasuyuki

supporting information, p. 6718 - 6724 (2021/05/26)

Herein, we report the highly potent catalytic methane oxidation activity of a monocationic μ-nitrido-bridged iron phthalocyanine dimer with 16 peripheral methyl groups. It was confirmed that this complex oxidized methane stably into MeOH, HCHO, and HCOOH in a catalytic manner in an acidic aqueous solution containing excess H2O2 at 60 °C. The total turnover number of the reaction reached 135 after 12 h, which is almost seven times higher than that of a monocatinoic μ-nitrido-bridged iron phthalocyanine dimer with no peripheral substituents. This suggests that the increased number of peripheral electron-donating substituents could have facilitated the generation of a reactive high-valent iron-oxo species as well as hydrogen abstraction from methane by the reactive iron-oxo species.

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