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References

[1] http://www.bio-medicine.org/biology-definition/Ethyl_alcohol/ [2] http://www.nutrientsreview.com/alcohol/definition-physical-chemical-properties.html [3] http://large.stanford.edu/courses/2010/ph240/luk1/ [4] http://www.highwaterethanol.com/index.cfm?show=10&mid=24 [5] M. Galbe, G. Zacchi, A review of the production of ethanol from softwood, Applied microbiology and biotechnology, 59(2002) 618-28. [6] J. Zaldivar, J. Nielsen, L. Olsson, Fuel ethanol production from lignocellulose: a challenge for metabolic engineering and process integration, Applied microbiology and biotechnology, 56(2001) 17-34. [7] Y. Sun, J. Cheng, Hydrolysis of lignocellulosic materials for ethanol production: a review, Bioresource technology, 83(2002) 1-11. [8] P.V. Harris, F. Xu, N.E. Kreel, C. Kang, S. Fukuyama, New enzyme insights drive advances in commercial ethanol production, Current opinion in chemical biology, 19(2014) 162-70. [9] http://www.bio-medicine.org/biology-definition/Ethyl_alcohol/ [10] https://lifeinthefastlane.com/tox-library/antidote/ethanol/ [11] https://www.worldofmolecules.com/fuels/ethanol.htm [12] J. Goldemberg, Ethanol for a sustainable energy future, science, 315(2007) 808-10. [13] https://www.worldofmolecules.com/fuels/ethanol.htm [14] https://www.exxon.com/en/ethanol [15] http://renewkansas.com/ethanol-advantages-benefits/ [16] http://energybc.ca/biofuels.html [17] C. Ibeto, A. Ofoefule, K. Agbo, A global overview of biomass potentials for bioethanol production: a renewable alternative fuel, Trends Appl Sci Res, 6(2011) 410e25. [18] https://www.epure.org/about-ethanol/beverage-industrial-use/ [19] https://www.msdsonline.com/2014/04/21/ethanol-versatile-common-and-potentially-dangerous/ [20] https://www.rxlist.com/consumer_ethanol_alcohol/drugs-condition.htm

Mechanism of action

A great deal of attention has been focused on a class of proteins termed the ligand-gated ion channels as being important to the mechanism of action of alcohol.These integral membrane proteins function as gates or pores that allow the passage of certain ions into and out of neurons upon binding of the appropriate neurotransmitter. This flux of ions largely determines the degree of neuronal activity. Two distinct types of ligand-gated ion channels are particularly sensitive to concentrations of alcohol that produce intoxication and sedation. These are the α-aminobutyric acid (GABA) chloride ionophore and the N-methyl-D-aspartate (NMDA) subtype of glutamate receptor. The GABA–chloride ion channel reduces neuronal activity by hyperpolarizing the neurons, while activation of the NMDA receptor causes neuronal depolarization or excitation. Alcohol has been shown to increase chloride flux through the GABAA receptor and reduce calcium flux through the NMDA receptor. These actions result in powerful suppression of nerve cell activity, which is consistent with the depressant actions of alcohol in the brain.

World Health Organization (WHO)

Ethanol has been used throughout recorded history both in a medicinal and a social context. It is currently included in pharmaceutical preparations either as an active or inactive ingredient. At pharmacologically active doses ethanol is both a powerful cerebral depressant and a drug of addiction. Its use in pharmaceutical preparations has been severely restricted in several countries and in 1986 the 39th World Health Assembly adopted a resolution to prohibit such use except when ethanol is an essential ingredient which cannot be replaced by an appropriate alternative.

Potential Exposure

Ethyl alcohol is used, topical antiinfective agent; solvent to make beverages; in the chemical synthesis of a wide variety of compounds, such as acetaldehyde, ethyl ether, ethyl chloride, and butadiene. It is a solvent or processing agent in the manufacture of pharmaceuticals; plastics, lacquers, polishes, plasticizers, perfumes, cosmetics, rubber accelerators; explosives, synthetic resins; nitrocellulose, adhesives, inks, and preservatives. It is also used as an antifreeze and as a fuel. It is an intermediate in the manufacture of many drugs and pesticides.

Production Methods

Ethanol is manufactured by the controlled enzymatic fermentation of starch, sugar, or other carbohydrates. A fermented liquid is produced containing about 15% ethanol; ethanol 95% v/v is then obtained by fractional distillation. Ethanol may also be prepared by a number of synthetic methods.

Uses

Medical A solution of 70-85% of ethanol is commonly used as a disinfectant and it kills organisms by denaturing their proteins and dissolving their lipids. It is effective against most bacteria and fungi, and many viruses, but is ineffective against bacterial spores. This disinfectant property of ethanol is the reason that alcoholic beverages can be stored for a long time[9]. Ethanol also has many medical uses, and can be found in products such as medicines, medical wipes and as an antiseptic in most antibacterial hand sanitizer gels. Ethanal can also be used as antidote. It competitively blocks the formation of toxic metabolites in toxic alcohol ingestions by having a higher affinity for the enzyme Alcohol Dehydrogenase (ADH). Its chief application is in methanol and ethylene glycol ingestions. Ethanol can be administered by the oral, nasogastric or intravenous route to maintain a blood ethanol concentration of 100-150 mg/dl (22-33 mol/L)[10]. Fuel Ethanol is flammable and burns more cleanly than many other fuels. Ethanol has been used in cars since Henry Ford designed his 1908 Model T to operate on alcohol. In Brazil and the United States, the use of ethanol from sugar cane and grain as car fuel has been promoted by government programs[11].?The Brazilian ethanol program started as a way to reduce the reliance on oil imports, but it was soon realized that it had important environmental and social benefits[12]. The fully combusted products of ethanol are only carbon dioxide and water. For this reason, it is environmental friendly and has been used to fuel public buses in the US. However, pure ethanol attacks certain rubber and plastic materials and cannot be used in unmodified car engines[13]. The alcohol-based alternative fuel that is blended with gasoline to produce a fuel with a higher octane rating and fewer harmful emissions than unblended gasoline. A mixture containing gasoline with at least 10% ethanol is known as gasohol. Specifically, gasoline with 10% ethanol content is known as E10. Another common gasohol variant is E15, which contains 15% ethanol and 85% gasoline. E15 is only appropriate for use in Flex Fuel vehicles or a very small percentage of the newest vehicles[14]. In addition, E85 is a term used for a mixture of 15% gasoline and 85% ethanol. E85 keeps the fuel system clean because it burns cleaner than regular gas or diesel and doesn't leave behind gummy deposits. Beginning with the model year 1999, a number of vehicles in the U.S. were manufactured so as to be able to run on E85 fuel without modification. These vehicles are often labeled dual fuel or flexible fuel vehicles, since they can automatically detect the type of fuel and change the engine's behavior to compensate for the different ways that they burn in the engine cylinders[15].? The use of ethanol-diesel fuel blends is growing around the world, and are designed to provide renewable, cleaner burning fuel alternatives for off-road equipment, buses, semi-trucks and other vehicles that run on diesel fuel. With the addition of ethanol and other fuel additives to diesel, the characteristic black diesel smoke is eliminated and there are significant reductions in particulate matter, carbon monoxide, and nitrogen oxide emissions. It is also possible to use ethanol for cooking as a replacement for wood, charcoal, propane, or as a substitute for lighting fuels, such as kerosene[16]. Brazil and the United States lead the industrial production of ethanol fuel, accounting together for 89% of the world's production in 2008. In comparison with the USA and Brazil, Europe ethanol for fuel production is still very modest. Brazil is the world's second largest producer of ethanol fuel and the world's largest exporter[17]. Beverage Significant volumes of ethanol are produced for the beverage and industrial markets from agricultural feedstock. Ethanol produced for these industries differs from ethanol for fuel only in its strength, which can vary between 96% and 99.9% and in its purity, depending on the end use. Beverage and drinks industry may be the best-known end-user of ethanol. It is used to make many kinds of spirits, such vodka, gin and anisette. High standards and processes are required for ethanal used in the production of spirit drinks. Others The ethanol used as an intermediary product by the chemical, pharmaceutical or cosmetics industry is in many cases of the highest and purest possible quality. These are premium markets due to the additional steps in the alcohol production process that are necessary to achieve the required purity. Same high standards and purity requirements apply in food industry, such as flavors and aromas extraction and concentrations, as well as paints and thermometers. Ethanol can be used in de-icer or anti-freeze to clear the car windscreen. It also is contained in perfumes, deodorants, and other cosmetics[18].

Preparation

There are several approaches to the production of ethanol; mainly ethanol is produced by fermentation.

Occurrence

Reported found in apple, apple aroma, apple essence, apple juice, bacon fat, banana, bean, beef fat, beef extract, blackberry, black currant, bread, brussels sprout, cabbage, carrot root, cauliflower, blue cheese, cheddar cheese, Swiss cheese, cocoa bean, cherry, coffee, cream, cucumber, alcoholic beverages and many other sources

History

Ethanol has been known to humans since prehistory as the active ingredient of alcoholic beverages. Its isolation as a relatively pure compound was probably achieved first by Islamic alchemists who developed the art of distillation[1].

Uses

One of the most prominent uses of ethyl alcohol is as a fuel additive and increasingly as a fuel itself. Ethyl alcohol is added to gasoline to increase its oxygen content and octane number. In the United States, the Environmental Protection Agency has mandated that oxygenated fuels be used in certain geographic areas to help meet air quality standards for carbon monoxide, especially in winter. A gasoline blended for this purpose may contain a few percent ethyl alcohol. Gasoline blended with ethyl alcohol is called gasohol. A typical gasohol may contain 90% gasoline and 10% ethanol. Gasohol reduces several common air pollutants including carbon monoxide, carbon dioxide, hydrocarbons, and benzene. Conversely, nitrogen oxides increase with gasohol.

Definition

ChEBI: A primary alcohol that is ethane in which one of the hydrogens is substituted by a hydroxy group.

Incompatibilities

In acidic conditions, ethanol solutions may react vigorously with oxidizing materials. Mixtures with alkali may darken in color owing to a reaction with residual amounts of aldehyde. Organic salts or acacia may be precipitated from aqueous solutions or dispersions. Ethanol solutions are also incompatible with aluminum containers and may interact with some drugs.

Health Hazard

The toxicity of ethanol is much lower thanthat of methanol or propanol. However, theliterature on the subject is vastly greater thanthat of any other alcohol. This is attributableessentially to its use in alcoholic beverages.There are exhaustive reviews on alcohol toxicity and free-radical mechanisms (Nordmannet al. 1987). The health hazard arises primarily from ingestion rather than inhalation. Ingestion of a large dose, 250–500 mL,can be fatal. It affects the central nervoussystem. Symptoms are excitation, intoxication, stupor, hypoglycemia, and coma — thelatter occurring at a blood alcohol contentof 300–400 0 mg/L. It is reported to have atoxic effect on the thyroid gland (Hegeduset al. 1988) and to have an acute hypotensiveaction, reducing the systolic blood pressurein humans (Eisenhofer et al. 1987). Chronicconsumption can cause cirrhosis of the liver.Inhalation of alcohol vapors can result inirritation of the eyes and mucous membranes.This may happen at a high concentrationof 5000–10,000 ppm. Exposure may resultin stupor, fatigue, and sleepiness. There isno report of cirrhosis occurring from inhalation. Chronic exposure to ethanol vapors hasproduced brain damage in mice. The neurotoxicity increases with thiamine deficiency(Phillips 1987). Both acute and chronic dosesof ethanol elevated the lipid peroxidation inrat brain. This was found to be elevated further by vitamin E deficiency, as well as itssupplementation (Nadiger et al. 1988).pplementation (Nadiger et al. 1988).The toxicity of ethanol is enhanced in thepresence of compounds such as barbiturates,carbon monoxide, and methyl mercury. Withthe latter compound, ethanol enhanced theretention of mercury in the kidney of ratsand thus increased nephrotoxicity (McNeilet al. 1988). When combined with cocaineand fed to rats, increased maternal and fetaltoxicity was observed (Church et al. 1988).Ethanol is reported to be synergisticallytoxic with caffeine (Pollard 1988) andwith n-butanol and isoamyl alcohol. Priorethanol consumption increased the toxicity of acetaminophen in mice (Carter1987).

Flammability and Explosibility

Ethanol is a flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." Ethanol vapor forms explosive mixtures with air at concentrations of 4.3 to 19% (by volume). Hazardous gases produced in ethanol fires include carbon monoxide and carbon dioxide. Carbon dioxide or dry chemical extinguishers should be used for ethanol fires.

Production

Ethanol is produced by fermenting and distilling grains. Actually, ethanol can be made from any plant that contains a large amount of sugar or components that can be converted into sugar, such as starch or cellulose. As their names imply, sugar beets and sugar cane contain natural sugar. Crops such as corn, wheat and barley contain starch that can be easily converted to sugar[3]. Today, ethanol is made primarily from corn. Another form of ethanol, called bioethanol, can be made from lignocellulosics which are from many types of trees and grasses, although the process is more difficult[4]. Lignocellulose consists of three main components: cellulose, hemicellulose and lignin, the first two being composed of chains of sugar molecules. Those chains can be hydrolyzed to produce monomeric sugars, some of which can be fermented using yeasts to produce ethanol. Ethanol can be produced from lignocellulosic materials in various ways, but all processes comprise the same main components: hydrolysis of the hemicellulose and the cellulose to monomer sugars, fermentation and product recovery and concentration by distillation[5]. Currently, ethanol production processes using crops are well-established. However, utilization of a cheaper substrate, such as lignocellulose, could make bioethanol more competitive with fossil fuel. Therefore, bacterial and yeast strains have been constructed which are advantageous for ethanol production[6]. The cost of ethanol production from lignocellulosic materials is relatively high based on current technologies, and the main challenges are the low yield and high cost of the hydrolysis process. Considerable research efforts have been made to improve the hydrolysis of lignocellulosic materials[7]. Besides, new enzymes have revolutionized the liquefaction process in starch ethanol and improved ethanol yield and product quality[8].

Safety and hazards

Even though ethanol is very commonly used, it is a dangerous chemical. As ethanal is highly flammable, it has exact flash points which needs to be noticed. While ethanol is consumed when drinking alcoholic beverages, consuming ethanol alone can cause coma and death. Ethanol may also be a carcinogenic[19]. Exposure to ethanol can be in vapor form (breathing it in), skin/body contact or ingestion. All are serious and need to be managed appropriately to ensure more damage is not incurred while trying to attend to the exposure. Common side effects of ethanol include: intoxication, low blood pressure (hypotension) with flushing, agitation, low blood sugar (hypoglycemia), nausea, vomiting and excessive urination[20].

Chemical Properties

Ethyl alcohol is a colorless, volatile, flammable liquid with a sweet, fruity odor. The Odor Threshold is 0.1355 ppm.

Purification Methods

Usual impurities of fermentation alcohol are fusel oils (mainly higher alcohols, especially pentanols), aldehydes, esters, ketones and water. With synthetic alcohol, likely impurities are water, aldehydes, aliphatic esters, acetone and diethyl ether. Traces of *benzene are present in ethanol that has been dehydrated by azeotropic distillation with *benzene. Anhydrous ethanol is very hygroscopic. Water (down to 0.05%) can be detected by formation of a voluminous precipitate when aluminium ethoxide in *benzene is added to a test portion, Rectified spirit (95% ethanol) is converted to absolute (99.5%) ethanol by refluxing with freshly ignited CaO (250g/L) for 6hours, standing overnight and distilling with precautions to exclude moisture. Numerous methods are available for further drying of absolute ethanol for making “Super dry ethanol”. Lund and Bjerrum [Chem Ber 64 210 1931] used reaction with magnesium ethoxide, prepared by placing 5g of clean dry magnesium turnings and 0.5g of iodine (or a few drops of CCl4), to activate the Mg, in a 2L flask, followed by 50-75 mL of absolute ethanol, and warming the mixture until a vigorous reaction occurs. When this subsides, heating is continued until all the magnesium is converted to magnesium ethoxide. Up to 1L of ethanol is then added and, after an hour's reflux, it is distilled off. The water content should be below 0.05%. Walden, Ulich and Laun [Z Phys Chem 114 275 1925] used amalgamated aluminium chips, prepared by degreasing aluminium chips (by washing with Et2O and drying in a vacuum to remove grease from machining the Al), treating with alkali until hydrogen evolved vigorously, washing with H2O until the washings were weakly alkaline and then stirring with 1% HgCl2 solution. After 2minutes, the chips were washed quickly with H2O, then alcohol, then ether, and dried with filter paper. (The amalgam became warm.) These chips were added to the ethanol, which was then gently warmed for several hours until evolution of hydrogen ceased. The alcohol was distilled and aspirated for some time with pure dry air. Smith [J Chem Soc 1288 1927] reacted 1L of absolute ethanol in a 2L flask with 7g of clean dry sodium, and added 25g of pure ethyl succinate (27g of pure ethyl phthalate was an alternative), and refluxed the mixture for 2hours in a system protected from moisture, and then distilled the ethanol. A modification used 40g of ethyl formate instead, so that sodium formate separated out and, during reflux, the excess of ethyl formate decomposed to CO and ethanol. Drying agents suitable for use with ethanol include Linde type 4A molecular sieves, calcium metal, and CaH2. The calcium hydride (2g) is crushed to a powder and dissolved in 100mL absolute ethanol by gently boiling. About 70mL of the ethanol are distilled off to remove any dissolved gases before the remainder is poured into 1L of ca 99.9% ethanol in a still, where it is boiled under reflux for 20hours, while a slow stream of pure, dry hydrogen (better use nitrogen or Ar) is passed through. It is then distilled [Rüber Z Elektrochem 29 334 1923]. If calcium is used for drying, about ten times the theoretical amount should be used, and traces of ammonia (from some calcium nitride in the Ca metal) would be removed by passing dry air into the vapour during reflux. Ethanol can be freed from traces of basic materials by distillation from a little 2,4,6-trinitrobenzoic acid or sulfanilic acid. *Benzene can be removed by fractional distillation after adding a little water (the *benzene/water/ethanol azeotrope distils at 64.9o), the alcohol is then re-dried using one of the methods described above. Alternatively, careful fractional distillation can separate *benzene as the *benzene/ethanol azeotrope (b 68.2o). Aldehydes can be removed from ethanol by digesting with 8-10g of dissolved KOH and 5-10g of aluminium or zinc per L, followed by distillation. Another method is to heat under reflux with KOH (20g/L) and AgNO3 (10g/L) or to add 2.5-3g of lead acetate in 5mL of water to 1L of ethanol, followed (slowly and without stirring) by 5g of KOH in 25mL of ethanol: after 1hour the flask is shaken thoroughly, then set aside overnight before filtering and distilling. The residual water can be removed by standing the distillate over activated aluminium amalgam for 1 week, then filtering and distilling. Distillation of ethanol from Raney nickel eliminates catalyst poisons. Other purification procedures include pre-treatment with conc H2SO4 (3mL/L) to eliminate amines, and with KMnO4 to oxidise aldehydes, followed by refluxing with KOH to resinify aldehydes, and distilling to remove traces of H3PO4 and other acidic impurities after passage through silica gel, and drying over CaSO4. Water can be removed by azeotropic distillation with dichloromethane (azeotrope boils at 38.1o and contains 1.8% water) or 2,2,4-trimethylpentane. [Beilstein 1 IV 1289.] Rapid purification: Place degreased Mg turnings (grease from machining the turnings is removed by washing with dry EtOH then Et2O, and drying in a vacuum) (5g) in a dry 2L round bottomed flask fitted with a reflux condenser (protect from air with a drying tube filled with CaCl2 or KOH pellets) and flush with dry N2. Then add iodine crystals (0.5g) and gently warm the flask until iodine vapour is formed and coats the turnings. Cool, then add EtOH (50mL) and carefully heat to reflux until the iodine disappears. Cool again then add more EtOH (to 1L) and reflux under N2 for several hours. Distil and store over 3A molecular sieves (pre-heated at

Hazard

Classified as a depressant drug. Though it is rapidly oxidized in the body and is therefore noncumulative, ingestion of even moderate amounts causes lowering of inhibitions, often succeeded by dizziness, headache, or nausea. Larger intake causes loss of m

Reactivity Profile

It liberates hydrogen when it reacts withmetal; forms acetaldehyde (toxic, flammable)on catalytic vapor phase dehydrogenation;ethyl ether (flammable) on dehydration withH2SO4 or a heterogeneous catalyst such asalumina, silica, SnCl2, MnCl2, or CuSO4;.

storage

Ethyl alcohol should be protected from physical damage. It should be kept stored in a cool, dry, well-ventilated location, away from any area where the fi re hazard may be acute. Outside or detached storage is preferred. Separate from incompatibles. Containers should be bonded and grounded for transfer to avoid static sparks. The storage and use areas should be free from smoking areas.

Indications

Intravenous use of ethanol, while once widely employed to inhibit premature labor, is now of historical interest only. Ethanol inhibits oxytocin release from the pituitary and thus indirectly decreases myometrial contractility. Today, 2-adrenomimetics and magnesium sulfate have replaced ethanol for parenteral tocolysis.

Brand name

Absolute alcohol;Alcohol aethylicus;Alcool;Avitoin;Banatol;B-tonin;Colfin;Desqyam-x;Duonale-e;Efatin;Equithesin;Hizeneck-d;Honkon-n;Kapsitrin;Keralyt;Levovinizol;Mikrozid;Neotizol;Panoxy;Papette;Piadarn;Polislerol;Protectaderm;Sicol;Sodaphilline;Softa man;Sotracarix;Verucid;Weingeist;Xeracin.

History

Alcohol is produced naturally from the fermentation of sugars, and it is assumed that prehistoric humans consumed alcohol when eating fermented fruits. The earliest direct evidence of alcohol consumption dates from the Neolithic period 10,000 years ago and consists of stone jugs used for holding alcoholic beverages. Ancient records and art from Egypt, Babylon, Mesopotamia, and other early civilizations indicate the use of alcohol as a beverage, medicine, and ceremonial drink. Records also show that the intoxicating effects of alcohol were known for thousands of years b.c.e. Alcoholic drinks were stored in Egyptian burial tombs, and deities devoted to alcoholic beverages were worshiped by different civilizations. As the human population expanded, alcoholic drinks assumed a prominent role in different cultures; for example, numerous references are made to wine in the Bible. Ancient Islamic alchemists advanced the practice of alcohol production by using distillation techniques. Distilled alcohols began to appear in the Middle Ages and was used in many remedies and medicines. A common practice by alchemists in different regions was the preparation of special liquors and brews with healing power. Aqua vitae (water of life) could refer to brandy, gin, whiskey, wine, or another form of alcoholic depending on the geographic area.

Contact allergens

Ethanol is widely used for its solvent and antiseptic properties. It is rather an irritant and sensitization has rarely been reported.

Regulatory Status

Included in the FDA Inactive Ingredients Database (dental preparations; inhalations; IM, IV, and SC injections; nasal and ophthalmic preparations; oral capsules, solutions, suspensions, syrups, and tablets; rectal, topical, and transdermal preparations). Included in the Canadian List of Acceptable Non-medicinal Ingredients. Included in nonparenteral and parenteral medicines licensed in the UK.

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.

Side effects

Acute Ethanol Intoxication and Hangover Ethanol intoxication is probably the best-known form of drug toxicity. Intoxicated individuals are a threat to themselves and others, particularly if they attempt to drive or operate machinery. Although death can result from ethanol overdose, usually the patient lapses into a coma before ingesting lethal quantities. Ethanol intoxication is sometimes mistakenly diagnosed as diabetic coma, schizophrenia, overdosage of other CNS depressant drugs, or skull fracture. An additional feature commonly associated with excessive ethanol consumption is difficulty in regulating body temperature. Hypothermia frequently results, with body temperature falling toward that of the ambient environment. This problem can be particularly severe in the elderly, who normally have difficulty regulating their body temperature. One of the consequences of ethanol intoxication is the hangover, a condition characterized by headache, nausea, sweating, and tremor. Although unpleasant, a hangover is not dangerous, even though the person having one may feel otherwise.

Chemical Properties

Ethyl alcohol is a colorless flammable liquid with a typical lower alcohol odor and is miscible in water in all proportions. It is stable and hygroscopic. It is incompatible with strong oxidizing agents, peroxides, acids, acid chlorides, acid anhydrides, alkali metals, ammonia, and moisture. Ethyl alcohol forms explosive mixtures with air. Ethyl alcohol is the most common solvent used in aerosols, cosmetics, pharmaceuticals, alcoholic beverages, vinegar production, and in the chemical synthesis of a large variety of products in different industries. For instance, in the manufacture of plastics, lacquers, polishes, plasticizers, perfumes, adhesives, rubber accelerators, explosives, synthetic resins, nitrocellulose, inks, preservatives, and as a fuel.

Chemical Properties

In the BP 2009, the term ‘alcohol’; used without other qualification refers to ethanol containing ≥99.5% v/v of C2H6O. The term‘alcohol’, without other qualification, refers to ethanol 95.1–96.9% v/v. Where other strengths are intended, the term ‘alcohol’ or ‘ethanol’is used, followed by the statement of the strength. In the PhEur 6.0, anhydrous ethanol contains not less than 99.5% v/v of C2H6O at 208℃. The term ethanol (96%) is used to describe the material containing water and 95.1–96.9% v/v of C2H6O at 208℃.

Uses

Ethanol is used primarily as a solvent — animportant industrial solvent for resins, lacquers, pharmaceuticals, toilet preparations,and cleaning agents; in the production of rawmaterials for cosmetics, perfumes, drugs, andplasticizers; as an antifreeze; as an automotive fuel additive; and from ancient times, inmaking beverages. Its pathway to the bodysystem is mainly through the consumption ofbeverages. It is formed by the natural fermentation of corn, sugarcane, and other crops.

Shipping

UN1170 Ethyl alcohol or Ethanol or Ethanol solutions or Ethyl alcohol solutions, Hazard Class: 3; Labels: 3-Flammable liquid.

Uses

Most ethyl alcohol is used in alcoholic beverages in suitable dilutions. Other uses are as solvent in laboratory and industry, in the manufacture of denatured alcohol, pharmaceuticals (rubbing Compounds, lotions, tonics, colognes), in perfumery, in organic synthesis. Octane booster in gasoline. Pharmaceutic aid (solvent).

Clinical Use

Generally, no treatment is required for acute ethanol intoxication. Allowing the individual to sleep off the effects of ethanol ingestion is the usual procedure. Hangovers are treated similarly; that is, no effective remedy exists for a hangover, except for controlling the amount of ethanol consumed. Sometimes ethanol overdose is a medical emergency. For example, prompt treatment is required if the patient is in danger of dying of respiratory arrest, is comatose, has dilated pupils, is hypothermic, or displays tachycardia. Treatment for severe ethanol overdose is generally supportive. Increased intracranial pressure can be relieved by intravenous administration of hypertonic mannitol. Hemodialysis can accelerate the removal of ethanol from the body. Stimulants of ethanol metabolism, such as fructose, are not sufficiently effective, and use of analeptics is not recommended because of the possibility of precipitating convulsions.The immediate concern in the treatment of alcoholics is detoxification and management of the ethanol withdrawal syndrome. Another pharmacological approach is the use of anticraving drugs, for example serotonin uptake inhibitors,dopaminergic agonists, and opioid antagonists.The only treatment that has shown considerable promise is one that uses the opioid antagonist naltrexone.

Uses

Suitable for use in the precipitation of nucleic acids.

Precautions

During handling of ethyl alcohol, workers should use chemical-resistant shields, monogoggles, proper gloves, laboratory coat/apron, and protective equipment as required. Workers and the workplace should have adequate ventilation vent hoods, class b extinguisher. Workers should avoid sources of heat, sparks, or flames. Waste disposal and spill should be collected in suitable containers or absorbed on a suitable absorbent material for subsequent disposal. Waste material should be disposed of in an approved incinerator or in a designated landfi ll site, in compliance with all federal, provincial, and local government regulations.

Uses

alcohol (alcohol SD-40; alcohol SDA-40; ethanol; ethyl alcohol) is widely used in the cosmetic industry as an antiseptic as well as a solvent given its strong grease-dissolving abilities. It is often used in a variety of concentrations in skin toners for acne skin, aftershave lotions, perfumes, suntan lotions, and toilet waters. Alcohol dries the skin when used in high concentrations. It is manufactured through the fermentation of starch, sugar, and other carbohydrates.

Safety Profile

Confirmed human carcinogen for ingestion of beverage alcohol. Experimental tumorigenic and teratogenic data. Moderately toxic to humans by ingestion. Moderately toxic experimentally by intravenous and intraperitoneal routes. Mildly toxic by inhalation and skin contact. Human systemic effects by ingestion and subcutaneous routes: sleep disorders, hallucinations, dtstorted perceptions, convulsions, motor activity changes, ataxia, coma, antipsychotic,headache, pulmonary changes, alteration in gastric secretion, nausea or vomiting, other gastrointestinal changes, menstrual cycle changes, and body temperature decrease. Can also cause glandular effects in humans. Human reproductive effects by ingestion, intravenous, and intrauterine routes: changes in female fertility index. Effects on newborn include: changes in Apgar score, neonatal measures or effects, and drug dependence. Experimental reproductive effects. Human mutation data reported. An eye and skin irritant. The systemic effect of ethanol differs from that of methanol. Ethanol is rapidly oxidtzed in the body to carbon dtoxide and water, and, in contrast to methanol, no cumulative effect occurs. Though ethanol possesses narcotic properties, concentrations sufficient to produce this effect are not reached in industry. Concentrations below 1000 pprn usually produce no signs of intoxication. Exposure to concentrations over 1000 pprn may cause headache, irritation of the eyes, nose, and throat, and, if continued for an hour, drowsiness and lassitude, loss of appetite, and inability to concentrate. There is no concrete evidence that repeated exposure to ethanol vapor results in cirrhosis of the liver. Ingestion of large doses can cause alcohol poisoning. Repeated ingestions can lead to alcoholism. It is a central nervous system depressant.Flammable liquid when exposed to heat or flame; can react vigorously with oxidizers. To fight fire, use alcohol foam, CO2, dry chemical. Explosive reaction with the oxidized coating around potassium metal. Ignites and then explodes on contact with acetic anhydride + sodum hydrogen sulfate. Reacts violently with acetyl bromide (evolves hydrogen bromide), dichloromethane + sulfuric acid + nitrate or nitrite, disulfuryl difluoride, tetrachlorosilane + water, and strong oxidants. Ignites on contact with disulfuric acid + nitric acid, phosphorus(IⅡ) oxide, platinum, potassium tert-butoxide + acids. Forms explosive products in reaction with ammonia + silver nitrate (forms silver nitride and silver fulminate), magnesium perchlorate (forms ethyl perchlorate), nitric acid + silver (forms silver fulminate), silver nitrate (forms ethyl nitrate), silverp) oxide + ammonia or hydrazine (forms silver nitride and silver fulminate), sodum (evolves hydrogen gas). Incompatible with acetyl chloride, BrF5, Ca(OCl)2, ClO3, Cr03, Cr(OCl)2, (cyanuric acid + H20), H202, HNO3, (H202 + H2SO4), (I + CH3OH + HgO), wn(ClO4)2 + 2,2-dimethoxy propane], Hg(NO3)2, HClO4, perchlorates, (H2SO4 + permanganates), HMn04, KO2, KOC(CH3)3, AgClO4, NaH3N2, uo2(clO4)2

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Definition

A colorless volatile liquid alcohol. Ethanol occurs in intoxicating drinks, in which it is produced by fermentation of a sugar: C6H12O6 → 2C2H5OH + 2CO2 Yeast is used to cause the reaction. At about 15% alcohol concentration (by volume) the reaction stops because the yeast is killed. Higher concentrations of alcohol are produced by distillation. Apart from its use in drinks, alcohol is used as a solvent and to form ethanal. Formerly, the main source was by fermentation of molasses, but now catalytic hydration of ethene is used to manufacture industrial ethanol. See also methylated spirits.

Pharmaceutical Applications

Ethanol and aqueous ethanol solutions of various concentrations are widely used in pharmaceutical formulations and cosmetics. Although ethanol is primarily used as a solvent, it is also employed as a disinfectant, and in solutions as an antimicrobial preservative. Topical ethanol solutions are used in the development of transdermal drug delivery systems as penetration enhancers. Ethanol has also been used in the development of transdermal preparations as a co-surfactant.

Carcinogenicity

In 1987, the International Agency for Research on Cancer (IARC) evaluated the cancer data on ethanol and alcoholic beverages in humans and animals . The IARC concluded that there was inadequate evidence for the carcinogenicity of ethanol and of alcoholic beverages in experimental animals, but there was sufficient evidence for the carcinogenicity of alcoholic beverages in humans. The IARC classified alcoholic beverages as a Group 1 carcinogen based on the occurrence of malignant tumors of the oral cavity, pharynx, larynx, esophagus, and liver that have been causally related to the consumption of alcoholic beverages.

Uses

ethyl alcohol (Etanol) is commonly known as rubbing alcohol. ethyl alcohol is ordinary alcohol and is used medicinally as a topical antiseptic, astringent, and anti-bacterial. At concentrations above 15 percent, it is also a broad-spectrum preservative against bacteria and fungi, and can boost the efficacy of other preservatives in a formulation. Cosmetic companies tend to use alcohol SD-40 in high-grade cosmetic manufacturing as they consider ethanol too strong and too drying for application on the skin. obtained from grain distillation, it can also be synthetically manufactured.

Chemical properties

Ethanol is highly soluble in water and organic solvents, but poorly soluble in fats and oils. Ethanol itself is a good solvent, which is used in cosmetics, paints and tinctures[2]. Density of ethanol at 68 °F (20 °C) is 789 g/l. Pure ethanol is neutral (pH ~7). Most alcoholic beverages are more or less acidic. Ethanol/ethyl alcohol is highly flammable liquid, hygroscopic, and fully miscible in water. Ethanol is incompatible with a large number of chemicals such as strong oxidising agents, acids, alkali metals, ammonia, hydrazine, peroxides, sodium, acid anhydrides, calcium hypochlorite, chromyl chloride, nitrosyl perchlorate, bromine pentafluoride, perchloric acid, silver nitrate, mercuric nitrate, potassium tert-butoxide, magnesium perchlorate, acid chlorides, platinum, uranium hexafluoride, silver oxide, iodine heptafluoride, acetyl bromide, disulphuryl difluoride, acetyl chloride, permanganic acid, ruthenium (VIII) oxide, uranyl perchlorate, and potassium dioxide.

Aroma threshold values

Detection: 8 to 900 ppb

Safety

Ethanol and aqueous ethanol solutions are widely used in a variety of pharmaceutical formulations and cosmetics. It is also consumed in alcoholic beverages. Ethanol is rapidly absorbed from the gastrointestinal tract and the vapor may be absorbed through the lungs; it is metabolized, mainly in the liver, to acetaldehyde, which is further oxidized to acetate. Ethanol is a central nervous system depressant and ingestion of low to moderate quantities can lead to symptoms of intoxication including muscle incoordination, visual impairment, slurred speech, etc. Ingestion of higher concentrations may cause depression of medullary action, lethargy, amnesia, hypothermia, hypoglycemia, stupor, coma, respiratory depression, and cardiovascular collapse. The lethal human blood-alcohol concentration is generally estimated to be 400–500 mg/100 mL. Although symptoms of ethanol intoxication are usually encountered following deliberate consumption of ethanol-containing beverages, many pharmaceutical products contain ethanol as a solvent, which, if ingested in sufficiently large quantities, may cause adverse symptoms of intoxication. In the USA, the maximum quantity of alcohol included in OTC medicines is 10% v/v for products labeled for use by people of 12 years of age and older, 5% v/v for products intended for use by children aged 6–12 years of age, and 0.5% v/v for products for use by children under 6 years of age. Parenteral products containing up to 50% of alcohol (ethanol 95 or 96% v/v) have been formulated. However, such concentrations can produce pain on intramuscular injection and lower concentrations such as 5–10% v/v are preferred. Subcutaneous injection of alcohol (ethanol 95% v/v) similarly causes considerable pain followed by anesthesia. If injections are made close to nerves, neuritis and nerve degeneration may occur. This effect is used therapeutically to cause anesthesia in cases of severe pain, although the practice of using alcohol in nerve blocks is controversial. Doses of 1mL of absolute alcohol have been used for this purpose. Preparations containing more than 50% v/v alcohol may cause skin irritation when applied topically. LD50 (mouse, IP): 0.93 g/kg LD50 (mouse, IV): 1.97 g/kg LD50 (mouse, oral): 3.45 g/kg LD50 (mouse, SC): 8.29 g/kg LD50 (rat, IP): 3.75 g/kg LD50 (rat, IV): 1.44 g/kg LD50 (rat, oral): 7.06 g/kg

Indications

Ethanol is the most widely abused drug in the world. There are more than 10 million alcoholics in the United States alone. Excessive consumption of alcoholic beverages has been linked to as many as half of all traffic accidents, two-thirds of homicides, and three-fourths of suicides, and it is a significant factor in other crimes, in family problems, and in personal and industrial accidents. The annual cost to the American economy has been estimated to exceed $100 billion in lost productivity, medical care, and property damage. Alcoholism has been difficult to define because of its complex nature.A person is generally considered an alcoholic, however, when his or her lifestyle is dominated by the procurement and consumption of alcoholic beverages and when this behavior interferes with personal, professional, social, or family relations. A light drinker generally is defined as one who consumes an average of one drink or less per day, usually with the evening meal; a moderate drinker is one who has approximately three drinks per day; and a heavy drinker is one who has five or more drinks per day (or in the case of binge drinkers, at least once per week with five or more drinks on each occasion).

Introduction

Ethanol, also known as ethyl alcohol (or grain spirits, or alcohol), is a clear colorless, volatile, flammable solvent with a characteristic odor. The boiling point of ethanal is 78.5°C. The bio-alcohol is found in alcoholic beverages. Concentrated alcohol has a strong burning taste, but it is somewhat sweet when diluted. It is also increasingly being used as a fuel (usually replacing or complementing gasoline). Its low melting point of -114.5° C allows it to be used in antifreeze products.

Description

Ethyl alcohol, also called ethanol, absolute alcohol, or grain alcohol, is a clear, colorless, flammable liquid with a pleasant odor. It is associated primarily with alcoholic beverages, but it has numerous uses in the chemical industry. The word alcohol is derived from the Arabic word al kuhul, which was a fine powder of the element antimony used as a cosmetic. In Medieval times, the word al kuhul came to be associated with the distilled products known as alcohols. The hydroxyl group, -OH, bonded to a carbon, characterizes alcohols. Ethyl is derived from the root of the two-carbon hydrocarbon ethane.
InChI:InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3

64-17-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (33361)  Ethanol, Alcohol Reagent, anhydrous, denatured, ACS, 94-96%    64-17-5 500ml 338.0CNY Detail
Alfa Aesar (33361)  Ethanol, Alcohol Reagent, anhydrous, denatured, ACS, 94-96%    64-17-5 1L 421.0CNY Detail
Alfa Aesar (33361)  Ethanol, Alcohol Reagent, anhydrous, denatured, ACS, 94-96%    64-17-5 4L 944.0CNY Detail
Alfa Aesar (33361)  Ethanol, Alcohol Reagent, anhydrous, denatured, ACS, 94-96%    64-17-5 *4x1L 982.0CNY Detail
Alfa Aesar (36642)  Ethanol, anhydrous, denatured, 85.8%, 13.3% methanol, 0.9% MIBK    64-17-5 500ml 197.0CNY Detail
Alfa Aesar (36642)  Ethanol, anhydrous, denatured, 85.8%, 13.3% methanol, 0.9% MIBK    64-17-5 1L 246.0CNY Detail
Alfa Aesar (36642)  Ethanol, anhydrous, denatured, 85.8%, 13.3% methanol, 0.9% MIBK    64-17-5 4L 467.0CNY Detail
Alfa Aesar (36642)  Ethanol, anhydrous, denatured, 85.8%, 13.3% methanol, 0.9% MIBK    64-17-5 20L 1861.0CNY Detail
Alfa Aesar (22930)  Ethanol, anhydrous, denatured, HPLC Grade, 90%, 5% methanol, 5% isopropanol    64-17-5 1L 335.0CNY Detail
Alfa Aesar (22930)  Ethanol, anhydrous, denatured, HPLC Grade, 90%, 5% methanol, 5% isopropanol    64-17-5 4L 1013.0CNY Detail
Alfa Aesar (22930)  Ethanol, anhydrous, denatured, HPLC Grade, 90%, 5% methanol, 5% isopropanol    64-17-5 *4x4L 2804.0CNY Detail
Alfa Aesar (44134)  Ethanol, anhydrous, denatured, HPLC Grade, 90%, packaged under Argon in resealable ChemSeal? bottles    64-17-5 100ml 368.0CNY Detail

64-17-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name ethanol

1.2 Other means of identification

Product number -
Other names Ethanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Solvent
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:64-17-5 SDS

64-17-5Synthetic route

acetic anhydride
108-24-7

acetic anhydride

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran for 6h; Ambient temperature;100%
With sodium amalgam; water
acetaldehyde
75-07-0

acetaldehyde

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With perchloric acid; 9,10-dihydro-10-methylacridine In acetonitrile at 59.9℃; for 1h; Product distribution; other aldehydes and ketones; primary kinetic isotope effects (kH/kD);100%
With tris(triphenylphosphine)ruthenium(II) chloride; formic acid; tributyl-amine In various solvent(s) for 0.5h; Ambient temperature;89%
With ammonium chloride; zinc In tetrahydrofuran; water at 20℃; for 0.333333h;84%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 1h;100%
ethyl acetate
141-78-6

ethyl acetate

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With trans-RuCl2(PPh3)[PyCH2NH(CH2)2PPh2]; hydrogen; sodium ethanolate at 40℃; under 37503.8 Torr; for 16h; Catalytic behavior;100%
With C18H28Br2N4Ru; potassium tert-butylate; hydrogen In 1,4-dioxane at 105℃; under 22502.3 Torr; for 8h;99%
With (Ppyz)Zr(BH4)2Cl2 In diethyl ether for 4h; Heating;94%
Phenyl acetate
122-79-2

Phenyl acetate

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;100%
With C17H16BrMnNO3P; potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 16h; Autoclave;89%
methanol
67-56-1

methanol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
octanol
111-87-5

octanol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

1-octyl 3-phenylpropanoate
37826-57-6

1-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%
rac-octan-2-ol
4128-31-8

rac-octan-2-ol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

oct-2-yl 3-phenylpropionate
133577-58-9

oct-2-yl 3-phenylpropionate

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

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

A

ethanol
64-17-5

ethanol

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%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

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%
ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

3-Phenyl-2-propyn-1-ol
1504-58-1

3-Phenyl-2-propyn-1-ol

A

ethanol
64-17-5

ethanol

B

1-phenylpropynyl 3-phenylpropanoate
28049-00-5

1-phenylpropynyl 3-phenylpropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

sec-butyl 3-phenylpropanoate
51869-23-9

sec-butyl 3-phenylpropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
propylene glycol
57-55-6

propylene glycol

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With Raney Ni In water at 179.84℃; for 1h; Inert atmosphere; Autoclave;100%
ethylene glycol
107-21-1

ethylene glycol

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With Raney Ni In water at 179.84℃; for 1h; Inert atmosphere; Autoclave;100%
With hydrogen In water at 119.84℃; under 25502.6 Torr; for 4h;
With magnesium oxide In water at 290℃; for 3h; Time; Concentration; Inert atmosphere;
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C17H16BrMnNO3P; potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 16h; Autoclave;99%
With DEANB/5 mol% SpiroCAT formulation In tetrahydrofuran at 20 - 22℃; for 72h;95 %Spectr.
D-glucose
50-99-7

D-glucose

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With manganese(II) sulfate; rubidium sulfate; sulfuric acid; magnesium sulfate In water at 40℃; for 0.166667h; Temperature; Reagent/catalyst;100%
With cesium sulfate; sulfuric acid; water; magnesium sulfate; 2Co(2+)*2O4S(2-) at 145℃;
With sulfuric acid In water at 33℃; for 72h; pH=3.9; Kinetics; Reagent/catalyst; Temperature; Microbiological reaction;
3-ethoxyprop-1-ene
557-31-3

3-ethoxyprop-1-ene

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With hexaaquaruthenium(II) tosylate In water-d2 at 50℃; for 18h; Inert atmosphere;100%
glycerol
56-81-5

glycerol

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With 20% CsNO3 loaded onto HZSM-5(1500) zeolite at 350℃; under 760.051 Torr; for 2h; Catalytic behavior; Time; Flow reactor; Green chemistry;99.6%
With water; hydrogen at 300℃; under 31029.7 Torr; Flow reactor;
Stage #1: glycerol With 3% Pd/C In water at 220℃; for 3h; Autoclave;
Stage #2: With ammonium hydroxide at 0 - 50℃; for 1h;
acetic acid
64-19-7

acetic acid

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With water In aq. phosphate buffer at 20℃; pH=7.4; Electrolysis; Inert atmosphere; Enzymatic reaction;99.2%
With ruthenium-carbon composite; hydrogen In water at 119.84℃; under 7500.75 - 60006 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Autoclave; Sealed tube;94%
With hydrogen In water at 79.84℃; under 45004.5 Torr; Flow reactor;83%
5-ethoxythianthrenium perchloratexi850

5-ethoxythianthrenium perchloratexi850

A

thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

B

ethanol
64-17-5

ethanol

C

Thianthrene
92-85-3

Thianthrene

Conditions
ConditionsYield
With sodium thiophenolate; thiophenol In dimethyl sulfoxide for 2h; Product distribution; Further Variations:; Solvents; Substitution; elimination;A 1%
B 96%
C 99%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

A

ethanol
64-17-5

ethanol

B

3-phenyl-2-propen-1-yl 3-phenylacrylate
40918-97-6, 61019-10-1, 122-69-0

3-phenyl-2-propen-1-yl 3-phenylacrylate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 99%
8-(tetrahydro-2H-pyran-2-yloxy)octan-1-ol
51326-52-4

8-(tetrahydro-2H-pyran-2-yloxy)octan-1-ol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

8-(2-tetrahydropyranyloxy)octyl 3-phenylpropanoate

8-(2-tetrahydropyranyloxy)octyl 3-phenylpropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 99%
ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

benzyl alcohol
100-51-6

benzyl alcohol

A

ethanol
64-17-5

ethanol

B

Benzyl 3-phenylpropionate
22767-96-0

Benzyl 3-phenylpropionate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 99%
ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

cyclohexanol
108-93-0

cyclohexanol

A

ethanol
64-17-5

ethanol

B

cyclohexyl 3-phenylpropionate
22847-18-3

cyclohexyl 3-phenylpropionate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 99%
benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

A

ethanol
64-17-5

ethanol

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Reagent/catalyst; Inert atmosphere; Glovebox;A n/a
B 99%
With C18H28Br2N4Ru; potassium tert-butylate; hydrogen In 1,4-dioxane at 105℃; under 22502.3 Torr; for 8h;A n/a
B 94%
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Reagent/catalyst; Glovebox; Sealed tube; Overall yield = 98 %;A n/a
B 92%
With C42H38N4OPRu(1+)*Cl(1-); potassium tert-butylate; hydrogen In toluene at 100℃; under 4104.28 Torr; for 2h;
2-methylpropyl acetate
110-19-0

2-methylpropyl acetate

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With C17H16BrMnNO3P; potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 16h; Autoclave;99%
ethyl cyclohexanecarboxylate
3289-28-9

ethyl cyclohexanecarboxylate

A

ethanol
64-17-5

ethanol

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;A n/a
B 99%
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube; Overall yield = 99 %;
(-)-menthol
2216-51-5

(-)-menthol

ethyl acetoacetate
141-97-9

ethyl acetoacetate

A

ethanol
64-17-5

ethanol

B

(L)-menthyl 3-oxobutyrate
59557-05-0

(L)-menthyl 3-oxobutyrate

Conditions
ConditionsYield
at 140℃; for 5h;A n/a
B 98%
at 100℃; Equilibrium constant;
Geraniol
106-24-1

Geraniol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

(E)-3,7-dimethylocta-2,6-dien-1-yl 3-phenylpropanoate

(E)-3,7-dimethylocta-2,6-dien-1-yl 3-phenylpropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 98%
piperidine
110-89-4

piperidine

ethanol
64-17-5

ethanol

1-ethyl-piperidine
766-09-6

1-ethyl-piperidine

Conditions
ConditionsYield
With Zr6O4(OH)4(BDC-NH2)5.7([LIr]BF4)0.3 at 80℃; for 2h; Catalytic behavior; Autoclave; Green chemistry;100%
ruthenium trichloride at 220℃; for 2h; Product distribution; Mechanism; also with other catalyst;92%
ruthenium trichloride at 220℃; for 2h;92%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

ethanol
64-17-5

ethanol

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

Conditions
ConditionsYield
With tellurium; sodium tetrahydroborate; acetic acid for 4h; Heating; other alkyl and aryl esters of aryl carboxylic acids;100%
With tellurium; sodium tetrahydroborate; acetic acid for 4h; Heating;100%
With dilithium tetra(tert-butyl)zincate at 0℃; for 1h; Inert atmosphere;100%
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

ethanol
64-17-5

ethanol

ethyl 2-methylbenzoate
87-24-1

ethyl 2-methylbenzoate

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 12h;100%
With thionyl chloride at 0 - 80℃; Inert atmosphere;99.5%
With thionyl chloride at 0 - 80℃; Inert atmosphere;99.5%
4-chlorophenylacetic Acid
1878-66-6

4-chlorophenylacetic Acid

ethanol
64-17-5

ethanol

4-chloro-benzeneacetic acid, ethyl ester
14062-24-9

4-chloro-benzeneacetic acid, ethyl ester

Conditions
ConditionsYield
With sulfuric acid In benzene for 6h; Reflux;100%
sulfuric acid at 20℃;99%
With monoammonium 12-tungstophosphate for 12h; Heating;98%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethanol
64-17-5

ethanol

ethyl 2-ethoxyethanoate
817-95-8

ethyl 2-ethoxyethanoate

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 20℃; for 0.0833333h;100%
With polystyrene-linked tris(triazolyl)methane copper(I)(NCMe)][PF6] In neat (no solvent) for 3h; Inert atmosphere;98%
copper(II) bis(trifluoromethanesulfonate) at 22℃;97%
styrene oxide
96-09-3

styrene oxide

ethanol
64-17-5

ethanol

2-ethoxy-2-phenylethanol
36747-96-3

2-ethoxy-2-phenylethanol

Conditions
ConditionsYield
With erbium(III) triflate at 25℃; for 0.75h;100%
With cucurbit[7]uril at 35℃; for 1h; Temperature; Time;100%
With (Htrz)2[Mo3O6(O2)4(trz)2]*H2O at 35℃; for 6h;100%
5-bromomethyl-furan-2-carbaldehyde
39131-44-7

5-bromomethyl-furan-2-carbaldehyde

ethanol
64-17-5

ethanol

5-(ethoxymethyl)furfural
1917-65-3

5-(ethoxymethyl)furfural

Conditions
ConditionsYield
at 80℃; for 3h;100%
With oil shale ashes taken from pulverized-fired boiler (Ash A) In water at 20℃; for 17h; Reagent/catalyst;88%
With silver cyanide
With silver nitrate
With calcium carbonate
2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

ethanol
64-17-5

ethanol

2-aminopyridine-3-carboxylic acid ethyl ester
13362-26-0

2-aminopyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2-aminopyridin-3-carboxylic acid; ethanol With sulfuric acid for 16h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=8;
100%
With sulfuric acid at 90℃; for 12h;98.08%
With sulfuric acid Reflux;84%
Indole-2-carboxylic acid
1477-50-5

Indole-2-carboxylic acid

ethanol
64-17-5

ethanol

2-carbethoxyindole
3770-50-1

2-carbethoxyindole

Conditions
ConditionsYield
With hydrogenchloride for 24h; Heating / reflux;100%
With thionyl chloride In methanol at 0℃; Reflux;99%
With thionyl chloride for 2.25h; Cooling with ice; Reflux;99%
pyridine-2,4-dicarboxylic acid
499-80-9

pyridine-2,4-dicarboxylic acid

ethanol
64-17-5

ethanol

diethyl pyridine-2,4-dicarboxylate
41438-38-4

diethyl pyridine-2,4-dicarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 24h; Heating;100%
With toluene-4-sulfonic acid In toluene at 110℃;88%
Stage #1: ethanol With thionyl chloride at 0℃; for 0.5h; Inert atmosphere;
Stage #2: pyridine-2,4-dicarboxylic acid In ethanol for 3h; Inert atmosphere; Reflux;
82%
Pyridine-2,5-dicarboxylic acid
100-26-5

Pyridine-2,5-dicarboxylic acid

ethanol
64-17-5

ethanol

ethyl 2,5-pyridinedicarboxylate
5552-44-3

ethyl 2,5-pyridinedicarboxylate

Conditions
ConditionsYield
With sulfuric acid100%
With thionyl chloride for 14h; Reflux;98.9%
With thionyl chloride at 80℃;93.6%
4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

ethanol
64-17-5

ethanol

(4-hydroxy-phenyl)-acetic acid ethyl ester
17138-28-2

(4-hydroxy-phenyl)-acetic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid for 1h; Heating / reflux;100%
With sulfuric acid for 2h; Reflux;98%
With sulfuric acid In water for 8h; Reflux;98%
4-aminocyclohexanecarboxylic acid
1776-53-0

4-aminocyclohexanecarboxylic acid

ethanol
64-17-5

ethanol

ethyl 4-amino-1-cyclohexanecarboxylate
51498-33-0

ethyl 4-amino-1-cyclohexanecarboxylate

Conditions
ConditionsYield
With thionyl chloride at 80℃; Cooling with ice;100%
With thionyl chloride at 20℃; for 16h;
With thionyl chloride at 20℃; for 16h;
With thionyl chloride In ethanol at 80℃; for 3h; Cooling with ice;7.23 g
With hydrogenchloride
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

ethanol
64-17-5

ethanol

ethyl 4-hydroxy-3-methoxycinnamate
4046-02-0

ethyl 4-hydroxy-3-methoxycinnamate

Conditions
ConditionsYield
With acetyl chloride at 20℃;100%
With sulfuric acid at 88℃; under 1034.32 Torr; for 0.05h; Microwave irradiation;94%
With sulfuric acid for 4h; Reflux;94%
sarcosine
107-97-1

sarcosine

ethanol
64-17-5

ethanol

sarcosine ethyl ester hydrochloride
52605-49-9

sarcosine ethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 78℃;100%
With hydrogenchloride99%
With hydrogenchloride at 20℃; for 72h;95%
With hydrogenchloride
With acetyl chloride for 3h; Reflux;
ethanol
64-17-5

ethanol

2-Methylpentanoic acid
97-61-0, 22160-39-0

2-Methylpentanoic acid

manzanate
39255-32-8

manzanate

Conditions
ConditionsYield
zirconium(IV) oxide at 200℃; in vapor-phase or in liquid-phase or in autoclave;100%
With sulfuric acid
ethanol
64-17-5

ethanol

L-serin
56-45-1

L-serin

L-serine ethyl ester hydrochloride
26348-61-8

L-serine ethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0℃; Inert atmosphere;100%
With hydrogenchloride for 0.5h;98%
With thionyl chloride at 0 - 20℃; for 17h;98%
ethanol
64-17-5

ethanol

L-leucine
61-90-5

L-leucine

L-Leucine ethyl ester
2743-60-4

L-Leucine ethyl ester

Conditions
ConditionsYield
With thionyl chloride100%
With amberlyst-15 Ambient temperature;77%
With thionyl chloride for 10h; Heating;70%
ethanol
64-17-5

ethanol

L-isoleucine
73-32-5

L-isoleucine

L-isoleucine ethyl ester
921-74-4

L-isoleucine ethyl ester

Conditions
ConditionsYield
With thionyl chloride for 38h; Heating;100%
With thionyl chloride100%
With thionyl chloride for 10h; Heating;65%
ethanol
64-17-5

ethanol

L-Tartaric acid
87-69-4

L-Tartaric acid

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
With thionyl chloride100%
With methanesulfonic acid at 30 - 35℃; for 12h;99%
With thionyl chloride at 0 - 50℃; for 3.5h; Temperature;96.2%
ethanol
64-17-5

ethanol

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

oleic acid ethyl ester
111-62-6

oleic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid at 110℃; for 2h;100%
With C6H15N*C3H6O3S*3Cl(1-)*H(1+)*Zn(2+) for 4h; Reagent/catalyst; Reflux;99.17%
With sulfuric acid for 16h; Reflux;97%
ethanol
64-17-5

ethanol

Isovaleronitrile
625-28-5

Isovaleronitrile

ethyl 3-methylbutanimidate hydrochloride

ethyl 3-methylbutanimidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 0 - 20℃; for 12h; Inert atmosphere;100%
With hydrogenchloride at 0 - 20℃;99%
With hydrogenchloride at -10 - 0℃; for 2h;71%
ethanol
64-17-5

ethanol

3,3-Dimethylglutaric acid
4839-46-7

3,3-Dimethylglutaric acid

diethyl 3,3-dimethylglutarate
17804-59-0

diethyl 3,3-dimethylglutarate

Conditions
ConditionsYield
With thionyl chloride at 0 - 80℃; for 12h; Large scale;100%
With sulfuric acid In toluene92%
With sulfuric acid
ethanol
64-17-5

ethanol

L-phenylalanine
63-91-2

L-phenylalanine

H-Phe-OEt
3081-24-1

H-Phe-OEt

Conditions
ConditionsYield
With hydrogenchloride at 60℃; for 1h; prototype reaction (other amino acids and peptides);100%
With thionyl chloride100%
With thionyl chloride at 0℃; for 4h; Reflux;97%
ethanol
64-17-5

ethanol

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

ethyl fluorene-9-carboxylate
26878-12-6

ethyl fluorene-9-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere; Sealed tube;100%
With sulfuric acid for 8.5h; Heating;93%
With sulfuric acid
With hydrogenchloride
With hydrogenchloride
ethanol
64-17-5

ethanol

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

ethyl 4-nitrobenzoate
99-77-4

ethyl 4-nitrobenzoate

Conditions
ConditionsYield
With tert-butylamine for 10h; Heating;100%
Stage #1: ethanol With platinum(IV) oxide; hydrogen at 60℃; under 750.075 - 1500.15 Torr; for 2h; Autoclave; Green chemistry;
Stage #2: 4-nitrobenzoic acid methyl ester at 60℃; Autoclave; Inert atmosphere; Green chemistry; chemoselective reaction;
93%
With dichlorobis(1-butylimidazolium) zinc at 70 - 80℃;93%
ethanol
64-17-5

ethanol

2,4,5-Trichloronitrobenzene
89-69-0

2,4,5-Trichloronitrobenzene

1,5-diethoxy-2-chloro-4-nitro-benzene
130474-89-4

1,5-diethoxy-2-chloro-4-nitro-benzene

Conditions
ConditionsYield
Stage #1: ethanol With sodium
Stage #2: 2,4,5-Trichloronitrobenzene In ethanol at 0 - 25℃; Heating / reflux;
100%
With potassium hydroxide
ethanol
64-17-5

ethanol

2-(2-nitrophenyl)acetic acid
3740-52-1

2-(2-nitrophenyl)acetic acid

ethyl 2-nitrophenylacetate
31912-02-4

ethyl 2-nitrophenylacetate

Conditions
ConditionsYield
With sulfuric acid at 60℃; for 24h; Inert atmosphere;100%
With sulfuric acid Reflux; Inert atmosphere;97%
With sulfuric acid at 60℃; for 24h;96%
ethanol
64-17-5

ethanol

benzene-1,3,5-tricarboxylic acid
554-95-0

benzene-1,3,5-tricarboxylic acid

triethyl benzene-1,3,5-tricarboxylate
4105-92-4

triethyl benzene-1,3,5-tricarboxylate

Conditions
ConditionsYield
With hydrogenchloride Heating;100%
With hydrogenchloride for 1h; Heating;96.5%
With thionyl chloride at 0℃; for 12h; Reflux;93%
ethanol
64-17-5

ethanol

N-benzoyl-L-phenylalanine
2566-22-5

N-benzoyl-L-phenylalanine

(S)-ethyl N-benzoyl-phenylalaninate
19817-70-0, 64896-35-1, 7200-18-2

(S)-ethyl N-benzoyl-phenylalaninate

Conditions
ConditionsYield
With α-chymotrypsin In chloroform; water100%
With α-chymotrypsin In chloroform; water Equilibrium constant; also in water only; correlation with pH;
With hydrogenchloride
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