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67-56-1 Usage

Uses

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.

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.

Shipping

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

Health Hazard

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

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.

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.

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).

Uses

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).

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).

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.

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.

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.

Toxicity evaluation

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

Uses

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.

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.

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.

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.

Health Hazard

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..

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

Uses

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

Uses

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.

Chemical Properties

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.

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:

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).

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.

Chemical Properties

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 .

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

Definition

ChEBI: The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.

Uses

high purity grade for ICP-MS detection

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

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.

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.

Fire Hazard

Behavior in Fire: Containers may explode.

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.

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.

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.
InChI:InChI=1/CH4O.H2O/c1-2;/h2H,1H3;1H2

67-56-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (M0097)  Methanol [for Spectrophotometry]  >99.8%(GC) 67-56-1 500mL 265.00CNY Detail
Alfa Aesar (31721)  Methanol, ACS, absolute, low acetone, 99.8+%    67-56-1 500ml 190.0CNY Detail
Alfa Aesar (31721)  Methanol, ACS, absolute, low acetone, 99.8+%    67-56-1 1L 276.0CNY Detail
Alfa Aesar (31721)  Methanol, ACS, absolute, low acetone, 99.8+%    67-56-1 4L 794.0CNY Detail
Alfa Aesar (31721)  Methanol, ACS, absolute, low acetone, 99.8+%    67-56-1 *4x1L 912.0CNY Detail
Alfa Aesar (41467)  Methanol, anhydrous, 99.9%    67-56-1 250ml 239.0CNY Detail
Alfa Aesar (41467)  Methanol, anhydrous, 99.9%    67-56-1 1L 403.0CNY Detail
Alfa Aesar (41467)  Methanol, anhydrous, 99.9%    67-56-1 4L 824.0CNY Detail
Alfa Aesar (41838)  Methanol, anhydrous, 99.9%, packaged under Argon in resealable ChemSeal? bottles    67-56-1 250ml 288.0CNY Detail
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%

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