Ethanol - Wikipedia, the free encyclopedia

From Wikipedia, the free encyclopedia

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol , or drinking alcohol, is a volatile, flammable, colorless liquid. A psychoactive drug and one of the oldest recreational drugs known, ethanol produces a state known as alcohol intoxication when consumed. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a solvent, and as a fuel. In common usage, it is often referred to simply as alcohol or spirits.


1 Chemical formula 2 Name 3 History 4 Physical properties 4.1 Solvent properties 4.2 Flammability 5 Production 5.1 Ethylene hydration 5.2 Fermentation 5.2.1 Cellulosic ethanol 5.2.2 Hydrocarbon-based ethanol production 5.3 Prospective technologies 5.4 Testing 5.5 Purification 5.6 Grades of ethanol 5.6.1 Denatured alcohol 5.6.2 Absolute alcohol 5.6.3 Rectified spirits 6 Reactions 6.1 Ester formation 6.2 Dehydration 6.3 Combustion 6.4 Acid-base chemistry 6.5 Halogenation 6.6 Oxidation 7 Uses 7.1 As a fuel 7.2 Alcoholic beverages 7.3 Feedstock 7.4 Antiseptic 7.5 Treatment for poisoning by other alcohols 7.6 Solvent 7.7 Historical uses 8 Pharmacology 9 Drug effects 9.1 Short-term 9.1.1 Effects on the central nervous system 9.1.2 Effects on metabolism 9.1.3 Drug interactions 9.1.4 Magnitude of effects 9.2 Long-term 9.2.1 Birth defects 9.2.2 Other effects 10 Natural occurrence 11 See also
Systematic name Ethanol[1] Other names Absolute alcohol Alcohol Drinking alcohol Ethyl alcohol Ethyl hydrate Ethyl hydroxide Ethylic alcohol Ethylol Grain alcohol Hydroxyethane Methylcarbinol

Identifiers CAS number PubChem ChemSpider UNII EC number UN number DrugBank KEGG MeSH ChEBI ChEMBL RTECS number ATC code 64-17-5 702 682 3K9958V90M 200-578-6 1170 DB00898 D00068 Ethanol CHEBI:16236 CHEMBL545 KQ6300000 D01AE06 ( /atc_ddd_index /?code=D01AE06) ,D08AX08, V03AB16, V03AZ01 Beilstein Reference Gmelin Reference 1718733 787

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95 kPa (at 20 °C) 15. 159 K. in 1825 Faraday had unwittingly discovered that ethanol could be produced from ethylene (a component of coal gas) by acid-catalyzed hydration. Its empirical formula is C2H6O. Johann Tobias Lowitz obtained pure ethanol by mixing partially purified ethanol (the alcohol-water azeotrope) with an excess of anhydrous alkali and then distilling the mixture over low heat.[8] Antoine Lavoisier described ethanol as a compound of carbon.[5] Vapor pressure Acidity (pKa) Basicity (pKb) History For more details on this topic.000-year-old pottery found in China imply that Neolithic people consumed alcoholic beverages. Hennell and the French chemist Georges-Simon Sérullas independently discovered that sulphovinic acid could be decomposed into 12 References 13 Further reading 14 Appendix 15 External links 3DMet Jmol-3D images B01253 Image 1 (http://chemapps. which is attached to the oxygen of a hydroxyl group (–OH).69 D[4] Pharmacology Ethanol is the systematic name defined by the IUPAC nomenclature of organic chemistry for a molecule with two carbon atoms (prefix "eth-").wikipedia. a process similar to current industrial ethanol synthesis. S7. who found in 1826 that it contained "sulphovinic acid" (ethyl hydrogen sulfate). The intoxicating effects of ethanol consumption have been known since ancient times.9 1. was Raymond Lull. Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages.9[2] -1. having a single bond between them (suffix "-ane"). in contrast with alcohol-water mixtures.php?model=CCO) SMILES Chemical formula Ethanol is a 2-carbon alcohol with the molecular formula CH3CH2OH. 173 °F -0.001074 Pa s (at 25 °C)[3] 1. a British chemist. using the common organic chemistry notation of representing the ethyl group (C2H5) with Et.[16] Refractive index (n D) Viscosity Dipole moment Routes of administration Intramuscular Intravenous Oral Topical Hepatic Hazards Metabolism MSDS EU Index EU classification R-phrases S-phrases NFPA 704 External MSDS 603-002-00-5 F R11 (S2).stolaf.37 °C. which indicates that the carbon of a methyl group (CH3–) is attached to the carbon of a methylene group (–CH2–). S16 Flash point Autoignition temperature LD50 13–14 °C 362 °C 5628 mg kg−1 (oral. Dried residue on 9. 2 of 19 11/1/2012 6:22 AM .[14][15] Thus.[9][10] Fifty years later. and in 1807 Nicolas-Théodore de Saussure determined ethanol's chemical formula. -173 °F Boiling point Name log P 78.[12] He gave the resulting solution to Henry Hennell.[13] In 1828.[6] Although distillation was well known by the early Greeks and Arabs.Ethanol .0012 Pa s (at 20 °C).18 5.07 g mol−1 Colorless liquid 0. the first recorded production of alcohol from distilled wine was by the School of Salerno alchemists in the 12th century. An alternative notation is CH3–CH2–OH. and oxygen. It is a constitutional isomer of dimethyl ether. the free encyclopedia http://en. 352 K. He found that sulfuric acid could absorb large volumes of coal gas. εr. Molecular formula Molar mass Appearance Density Melting point InChI Properties C2H6O 46. hydrogen.[7] The first to mention absolute alcohol. Ethanol is often abbreviated as EtOH . etc.[11] Ethanol was first prepared synthetically in 1825 by Michael Faraday.36 0.[7] In 1796. 0. Archibald Scott Couper published the structural formula of ethanol. and an attached -OH group (suffix "-ol"). rat) Supplementary data page Structure and properties n. see Distilled /jmol/jmol. The fermentation of sugar into ethanol is one of the earliest biotechnologies employed by humanity. It is one of the first structural formulas determined.789 g/cm3 −114 °C.Wikipedia.

35 °C). NMR. colorless liquid that has a slight odor. Ethanol's hydroxyl group is able to participate in hydrogen bonding. When wine is swirled in a glass. This property partially explains the "tears of wine" phenomenon.Wikipedia.36242 (at λ=589.[18] With the advent of Prohibition in 1920. In chemistry.[23] Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms). mixtures with dodecane and higher alkanes show a miscibility gap below a certain temperature (about 13 °C for dodecane [25] ).[17] Original Ford Model T automobiles ran on ethanol until 1908.[21][26] Mixing ethanol and water is exothermic. ammonium chloride. As the wine's ethanol content decreases. chloroform. such as pentane and hexane.[23] Sodium and potassium chlorides are slightly soluble in Ethanol was used as lamp fuel in the United States as early as 1840. ethylene glycol. Ethanol-water mixtures have less volume than the sum of their individual components at the given fractions.[29] Hydrogen bonding causes pure ethanol to be hygroscopic to the extent that it readily absorbs water from the air. miscible with water and with many organic solvents.[23] Because the ethanol molecule also has a nonpolar end. glycerol. its surface tension increases and the thin film "beads up" and runs down the Ethanol burning with its spectrum depicted 3 of 19 11/1/2012 6:22 AM .[21][23] It is also miscible with light aliphatic hydrocarbons. and medicinal agents. such as propane. having a refractive index of 1. whose water miscibility decreases sharply as the number of carbons increases. including acetic acid. The physical properties of ethanol stem primarily from the presence of its hydroxyl group and the shortness of its carbon chain. it will also dissolve nonpolar substances. liquid. nitromethane. The tax was repealed in 1906. IR. and with aliphatic chlorides such as trichloroethane and tetrachloroethylene.[21] The triple point for ethanol is 150 K at a pressure of 4.[17] and ethanol fuel fell into disuse until late in the 20th century. notably sodium and potassium hydroxides.3 * 10-4 Pa. MS (verify) (what is: / ?) Except where noted otherwise. including scents. rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight. and toluene. colorings. Ethanol is slightly more refractive than water. magnesium chloride.[20] It burns with a smokeless blue flame that is not always visible in normal light. coloring. the free encyclopedia http://en. carbon tetrachloride. Mixtures of ethanol and water form an azeotrope at about 89 mole-% ethanol and 11 mole-% water[28] or a mixture of about 96 volume percent ethanol and 4% water at normal pressure and T = 351 K. 100 kPa) Infobox references In modern times. and more recently as a fuel for internal combustion engines. Mixing equal volumes of ethanol and water results in only 1. pyridine. Thermodynamic data Spectral data Phase behaviour Solid. diethyl ether. flavorings.92 volumes of mixture. Physical properties Ethanol is a volatile.and pressure-dependent and vanishes at temperatures below 303 K. but a tax levied on industrial alcohol during the Civil War made this use uneconomical. ethanol evaporates quickly from the thin film of wine on the wall of the glass. The polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds. ethanol intended for industrial use is also produced from [19] ethylene.[24] The miscibility of ethanol with alkanes is limited to alkanes up to undecane. Ethanol has widespread use as a solvent of substances intended for human contact or consumption.[22] Solvent properties Ethanol is a versatile solvent.wikipedia. gas UV. ammonium bromide. and medicines. The addition of even a few percent of ethanol to water sharply reduces the surface tension of water. and sodium bromide.3 nm and 18. acetone. benzene.Ethanol . This azeotropic composition is strongly temperature. with up to 777 J/mol[27] being released at 298 K. it is both an essential solvent and a feedstock for the synthesis of other products. The miscibility gap tends to get wider with higher alkanes and the temperature for complete miscibility increases. calcium chloride. including most essential oils[30] and numerous flavoring. It has a long history as a fuel for heat and light. data are given for materials in their standard state (at 25 °C. ethanol fuel sellers were accused of being allied with moonshiners.

Flammability An ethanol-water solution that contains 40% ABV will catch fire if heated to about 26 °C (79 °F) and if an ignition source is applied to it. primarily by the acid-catalyzed hydration of ethylene.88 °F). the flash point of ordinary wine containing 12. this process was used on an industrial scale by Union Carbide Corporation and others. Ethylene hydration Ethanol for use as an industrial feedstock or solvent (sometimes referred to as synthetic ethanol) is made from petrochemical feed stocks. via biological processes.Wikipedia.[32] The flash points of ethanol concentrations from 10% ABV to 96% ABV are shown below:[33] 10% — 49 °C (120 °F) 12.[37] The reaction is carried out with an excess of high pressure steam at 300 °C.60 °C (61.5% — about 52 °C (126 °F) 20% — 36 °C (97 °F) 30% — 29 °C (84 °F) 40% — 26 °C (79 °F) 50% — 24 °C (75 °F) 60% — 22 °C (72 °F) 70% — 21 °C (70 °F) 80% — 20 °C (68 °F) 90% — 17 °C (63 °F) 96% — 17 °C (63 °F) Hydrogen bonding in solid ethanol at −186 °C Alcoholic beverages that have a low concentration of ethanol will burn if sufficiently heated and an ignition source (such as an electric spark or a match) is applied to them. first practiced on the industrial scale in 1930 by Union Carbide. 94% denatured ethanol sold in a bottle for household use In an older process. but now only LyondellBasell uses it commercially. by fermenting sugars with yeast.[36] adsorbed onto a porous support such as silica gel or diatomaceous earth.[38] but now almost entirely glass in channels rather than as a smooth sheet. This catalyst was first used for large-scale ethanol production by the Shell Oil Company in 1947. represented by the chemical equation C2H4 + H2O → CH3CH2OH The catalyst is most commonly phosphoric acid.Ethanol .[35] Which process is more economical depends on prevailing prices of petroleum and grain feed stocks.wikipedia.5% ethanol is about 52 °C (126 °F). For example.. through the hydration of ethylene and.[31] The flash point of pure ethanol is 16.[34] Production Ethanol is produced both as a petrochemical. ethylene was hydrated indirectly by reacting it with concentrated sulfuric acid to produce ethyl sulfate.S. In the U. This is called its flash point. the free encyclopedia http://en. less than average room temperature. which was hydrolysed to yield ethanol and regenerate the sulfuric acid:[39] C2H4 + H2SO4 → CH3CH2SO4H CH3CH2SO4H + H2O → CH3CH2OH + H2SO4 Fermentation Main article: Ethanol fermentation 4 of 19 11/1/2012 6:22 AM .

S. This process is carried out at around 35–40 °C. cannot metabolize xylose.000 m3) to 100 million US gallons (380. General Motors announced a partnership with Coskata. 2008. Arkansas. the cost of the cellulase enzymes capable of hydrolyzing cellulose has been prohibitive. and sugar cane bagasse and energy crops such as switchgrass into fermentable sugars. or malt. the free encyclopedia http://en.[49] Prospective technologies The anaerobic bacterium Clostridium ljungdahlii.[47] In October 2011. The bacterium E. therefore.[citation needed] is produced by fermentation.wikipedia. In brewing beer.coli when genetically engineered with cow rumen genes and enzymes can produce ethanol from corn stover. Deployment of this technology could turn a number of cellulose-containing agricultural by-products. hemicellulose decomposes into mostly five-carbon sugars such as xylose.. this has traditionally been accomplished by allowing the grain to germinate.Wikipedia. The most ethanol-tolerant strains of yeast can survive up to approximately 15% ethanol by volume. The goal was to produce cellulosic ethanol cheaply. which.[45] Cellulose-bearing materials typically also contain other polysaccharides.[48] Hydrocarbon-based ethanol production A process developed and marketed by Celanese Corporation under the name TCX Technology uses hydrocarbons such as natural gas or coal for ethanol production rather than using fermented crops such as corn or sugarcane. higher concentrations. and by 2011 to have a full-scale plant on line. fungally produced amylase. When undergoing hydrolysis. such as corncobs. or some combination of the two. Other yeasts and bacteria are under investigation to ferment xylose and other pentoses into ethanol. Pennsylvania. are usually obtained by fortification or distillation.[44] Its primary consumer so far has been the Canadian government.[41] Cellulosic ethanol Main article: Cellulosic ethanol Sugars for ethanol fermentation can be obtained from cellulose. which produces the enzyme amylase. a mixture of carbon monoxide and hydrogen that can be generated from the partial combustion of either fossil fuels or biomass. xylanase. along with the United States Department of Energy.[40] To produce ethanol from starchy materials such as cereal grains.[50] The BRI technology has been purchased by INEOS. into renewable energy resources. discovered in commercial chicken wastes. with an eventual goal of US$1 per US gallon ($0.30/L) for the fuel. and sawdust. had been running successfully for 2 years and that a full scale facility was planned for Alabama.Ethanol . including hemicellulose. cerevisiae . For fuel ethanol. the yeast most commonly used for ethanol production.g. Other enzyme companies are developing genetically engineered fungi that produce large volumes of cellulase. has invested heavily in the commercialization of cellulosic ethanol. the starch must first be converted into sugars. These would convert agricultural residues such as corn stover. wheat straw. When the malted grain is mashed. When certain species of yeast (e. Use of these bacteria to produce ethanol from synthesis gas has progressed to the pilot plant stage at the BRI Energy facility in Fayetteville. capable of producing 50 million US gallons (190. and the vast majority of ethanol for use as fuel. The Canadian firm Iogen brought the first cellulose-based ethanol plant on-stream in 2004. Toxicity of ethanol to yeast limits the ethanol concentration obtainable by brewing.[51] 5 of 19 11/1/2012 6:22 AM . and hemicellulase enzymes. The partnership planned to begin producing the fuel in large quantity by the end of 2008. Inc. however. the hydrolysis of starch into glucose can be accomplished more rapidly by treatment with dilute sulfuric acid.[42][43] Until See also: Yeast in winemaking Ethanol for use in alcoholic beverages. The chemical equations below summarize the conversion: C6H12O6 → 2 CH3CH2OH + 2 CO2 C12H22O11 + H2O → 4 CH3CH2OH + 4 CO2 Fermentation is the process of culturing yeast under favorable thermal conditions to produce alcohol. straw. the amylase converts the remaining starches into sugars. Saccharomyces cerevisiae ) metabolize sugar in reduced-oxygen conditions they produce ethanol and carbon dioxide.[46] On January 14. can produce ethanol from single-carbon sources including synthesis gas.000 m3) of ethanol a year (200–400 ML/a). an article on the Coskata website stated that a "semi-commercial" pilot plant in Madison.

This inexpensive and indirect method has a long history in the beer brewing industry. This method uses a relatively inexpensive solid state sensor that compares the CH band with a reference band to calculate the ethanol content.[56] There is also an absolute alcohol production process by desiccation using glycerol. or zeolites. sugarcane bagasse. South Dakota An alternative technology allows for the production of biodiesel from distillers grain as an additional value product. Infrared ethanol sensors measure the vibrational frequency of dissolved ethanol using the CH band at 2900 cm−1.6% by volume (89.wikipedia. Infrared reflection spectra of liquid ethanol. There is also the issue of competition with use of corn for food production. which adsorb water preferentially. Fractional distillation can concentrate ethanol to 95. In a closed-loop plant. Most ethanol fuel refineries use an adsorbent or zeolite to desiccate the ethanol stream. the closed-loop ethanol plant attempts to address this criticism. In another method to obtain absolute alcohol. This mixture is an azeotrope with a boiling point of 78. Grades of ethanol Denatured alcohol Main article: Denatured alcohol 6 of 19 11/1/2012 6:22 AM . the change in specific gravity during fermentation indicates the alcohol content. corn grits.3 °C (351. obtained in the third fraction. For most industrial and fuel uses. there is some development of alternative production methods that use feed stocks such as municipal waste or recycled products. a small quantity of benzene is added to rectified spirit and the mixture is then distilled.[24] Because a small amount of the benzene used remains in the solution. The calculation makes use of the Beer-Lambert law. wood chips.[54] Though in an early stage of research. small diameter trees. Alcohol produced by this method is known as spectroscopic alcohol—so called because the absence of benzene makes it suitable as a solvent in spectroscopy. renewable energy for distillation comes from fermented manure. Such a process is expected to lower the fossil fuel consumption used during conversion to ethanol by 75%. and cannot be further purified by distillation.[52] Ethanol produced from corn has a number of critics who suggest that it is primarily just recycled fossil fuels because of the energy required to grow the grain and convert it into ethanol. by measuring the density of the starting material and the density of the product. rice hulls.Ethanol . Alternatively. absolute alcohol produced by this method is not suitable for consumption. the ethanol must be purified.4 K). Absolute alcohol is Near infrared spectrum of liquid ethanol. produced from cattle that have been fed the DDSG by-products from grain ethanol production.1 °C. using a hydrometer.5 mole%).org/wiki/Ethanol Another prospective technology is the closed-loop ethanol plant. as benzene is carcinogenic. the free encyclopedia http://en. Common methods for obtaining absolute ethanol include desiccation using adsorbents such as starch. which distills over at 78.Wikipedia. and switchgrass.[55] Testing Breweries and biofuel plants employ two methods for measuring ethanol concentration.[53] Ethanol plant in Turner County. The concentrated compost nutrients from manure are then used to fertilize the soil and grow the next crop of grain to start the cycle again. showing the -OH band centered at ~3300 cm−1 and C-H bands at ~2950 cm−1. However. Purification Main article: Ethanol purification Ethylene hydration or brewing produces an ethanol–water mixture. as well as azeotropic distillation and extractive distillation.

The impurities are different from those in 190 proof laboratory Pure ethanol and alcoholic beverages are heavily taxed as a psychoactive drug. meaning that the carbon its hydroxyl group attaches to has at least two hydrogen atoms attached to it as well. Esters react in the presence of an acid or base to give back the alcohol and a salt. This reaction is known as saponification because it is used in the preparation of soap.Wikipedia. ethylene will be the main product. most jurisdictions waive the tax when an agent has been added to the ethanol to render it unfit to drink. requires the removal of the water from the reaction mixture as it is formed.[57][58] Absolute alcohol Absolute or anhydrous alcohol refers to ethanol with a low water content. Ethanol can be quantitatively converted to 7 of 19 11/1/2012 6:22 AM . where water will react with other chemicals. Diethyl sulfate is a useful ethylating agent in organic synthesis.[59] Absolute ethanol is used as a solvent for laboratory and industrial applications. ethanol reacts with carboxylic acids to produce ethyl esters and water: RCOOH + HOCH2CH3 → RCOOCH2CH3 + H2O This reaction. To relieve the tax burden on these uses. Ethyl nitrite.[61] Rectified spirits Rectified spirit. see Alcohol. benzene). it will contain trace amounts of the material separation agent (e. naphtha. Dehydration Strong acid desiccants cause the dehydration of ethanol to form diethyl ether and other byproducts.g. These include bittering agents such as denatonium benzoate and toxins such as methanol. There are various grades with maximum water contents ranging from 1% to ppm levels. fit for use as a solvent in ultraviolet-visible spectroscopy. Ethanol is classified as a primary alcohol. but ethanol has many uses that do not involve consumption by humans. (ΔHc = −1371 kJ/mol[63]) specific heat = 2. Ethanol can also form esters with inorganic acids. and pyridine.[60] Pure ethanol is classed as 200 proof in the USA. was formerly a widely used diuretic. Absolute alcohol is not intended for human consumption. which is conducted on large scale industrially. Ester formation In the presence of acid catalysts. Millions of kilograms of diethyl ether are produced annually using sulfuric acid catalyst: 2 CH3CH2OH → CH3CH2OCH2CH3 + H2O (on 120 °C) Combustion Complete combustion of ethanol forms carbon dioxide and water vapor: C2H5OH (l) + 3 O2 (g) → 2 CO2 (g) + 3 H2O (g). Diethyl sulfate and triethyl phosphate are prepared by treating ethanol with sulfur trioxide and phosphorus pentoxide respectively. is used instead of anhydrous ethanol for various purposes. an azeotropic composition containing 4% water. and as fuel alcohol. Products of this kind are called denatured alcohol. Many ethanol reactions occur at its hydroxyl group. the free encyclopedia http://en. Wine spirits are about 188 proof. equivalent to 175 degrees proof in the UK system.00. If azeotropic distillation is used to remove water.Ethanol .[62] Reactions For more details on this topic. If the dehydration temperature exceeds around 160 °C. Spectroscopic ethanol is an absolute ethanol with a low absorbance in ultraviolet and visible light.44 kJ/(kg·K) Acid-base chemistry Ethanol is a neutral molecule and the pH of a solution of ethanol in water is nearly 7. prepared from the reaction of ethanol with sodium nitrite and sulfuric acid.wikipedia.

Thus. 105 Research octane number 8 of 19 11/1/2012 6:22 AM .6[66] 25. but the reactions are illustrative. depending on the reagents and conditions.7[66] 21. Br.[39] This oxidation is of no importance industrially. where the acetyl group can be spent as energy or used for biosynthesis.[39] HBr requires refluxing with a sulfuric acid catalyst. as indicated by their pKa of 15. but in the human body. such as thionyl chloride or phosphorus tribromide.Ethanol . Ethanol may also be utilized as a rocket fuel.8[67] 108. 15% gasoline) Liquefied natural gas Autogas (LPG) (60% propane + 40% butane) 17.[24][39] CH3CH2OH + SOCl2 → CH3CH2Cl + SO2 + HCl Upon treatment with halogens in the presence of base.3 26.wikipedia. the ethoxide ion (CH3CH2O−).9 MJ/L MJ/kg ~19. Brazil relies on ethanol as a motor its conjugate base.8 33. I).Wikipedia. being a precursor to acetyl CoA.7 and 16 respectively. Hydrous ethanol (about 95% ethanol and 5% water) can be used as fuel in more than 90% of new cars sold in the country. by reaction with an alkali metal such as sodium:[24] 2 CH3CH2OH + 2 Na → 2 CH3CH2ONa + H2 or a very strong base such as sodium hydride: CH3CH2OH + NaH → CH3CH2ONa + H2 The acidity of water and ethanol are nearly the same.[69] The US uses Gasohol (max 10% ethanol) and E85 (85% ethanol) ethanol/gasoline mixtures.[39] Ethyl halides can. This conversion is called the haloform reaction. the free encyclopedia http://en. Ethanol reacts with hydrogen halides to produce ethyl halides such as ethyl chloride and ethyl bromide via an SN2 reaction: CH3CH2OH + HCl → CH3CH2Cl + H2O These reactions require a catalyst such as zinc chloride.2[67] 26. The oxidation product of ethanol. in principle. where X = Cl.[64] " An intermediate in the reaction with chlorine is the aldehyde called chloral: 4 Cl2 + CH3CH2OH → CCl3CHO + 5 HCl Oxidation Ethanol can be oxidized to acetaldehyde and further oxidized to acetic acid.5 19. and is currently in lightweight rocket-powered racing aircraft.[70] Energy content of some fuels compared with ethanol:[65] Fuel type Dry wood (20% moisture) Methanol Ethanol E85 (85% ethanol. Gasoline sold in Brazil contains at least 25% anhydrous ethanol.2 25. Uses As a fuel Main article: Ethanol fuel The largest single use of ethanol is as a motor fuel and fuel additive. is a nutrient for humans. also be produced by treating ethanol with more specialized halogenating agents. More than any other major country.9 108. these oxidation reactions are catalyzed by the enzyme liver alcohol dehydrogenase. acetic acid.2 ~55 50. ethanol gives the corresponding haloform (CHX3. sodium ethoxide and sodium hydroxide exist in an equilbrium that is closely balanced: CH3CH2OH + NaOH CH3CH2ONa + H2O Halogenation Ethanol is not used industrially as a precursor to ethyl halides. Brazilian ethanol is produced from sugar cane and noted for high carbon sequestration.

S. 104 45. they showed reductions of 8% with the biodiesel/petrodiesel blend known as B20.000.Ethanol . Diesel 38. 131 grain ethanol bio-refineries in the United States have the capacity to produce 7. Brazil where the fuel is available commercially. over long distances.3 × 10 US gal). like liquid hydrocarbons. the Open Fuel Standard Coalition introduced a bill into Congress that would mandate 9 of 19 11/1/2012 6:22 AM . oxides of nitrogen. Charcoal. with 69% of the world supply coming from Brazil and the United States.4 billion US gallons ( Australian law limits of the use of pure ethanol sourced from sugarcane waste to up to 10% in automobiles.[citation needed] The United States fuel ethanol industry is based largely on corn.[75] These data have been assembled into The Clean Fuels Report comparison of fuel emissions[76] and show that ethanol exhaust generates 2.[72] Argonne National Laboratory analyzed the greenhouse gas emissions of many different engine and fuel combinations. it is believed that a material portion of the ≈150-billion-US-gallon (570.4 23 25 According to an industry advocacy group for promoting Premium gasoline/petrol ethanol called the American Coalition for Ethanol. extruded 50 and other ozone-forming pollutants. but is used in power plants to produce electricity.4[68] min. 17% with the conventional E85 ethanol blend.[80] One problem with ethanol is its high miscibility with water. in particular. particulate matter.8 47.Wikipedia. but is also much easier to extract.000 m3) per year market for gasoline will begin to be replaced with fuel ethanol.[81] Mechanics also have seen increased cases of damage to small engines. attributable to the increased water retention by ethanol in fuel.000.000 m3) of ethanol per year.7 on a scale where gasoline is 1. Brazil supports this population of ethanol-burning automobiles with large national infrastructure that produces ethanol from domestically grown sugar cane. 2007.5 (high-octane gasoline. It has been recommended that older cars (and vintage cars designed to use a slower burning fuel) have their valves upgraded or replaced. World production of ethanol in 2006 was 51 gigalitres laboratory use. much like the conventional NOx and Reactive Organic Gases (ROGs). Comparing ethanol blends with gasoline alone.1 100/130 (lean/rich) 93/94 44.0 billion US gallons (26. the free encyclopedia http://en. The bagasse generated by the process is not wasted. In the US flex-fuel vehicles can run on 0% to 85% ethanol (15% gasoline) since higher ethanol blends are not yet allowed or efficient. the carburetor. 91 max.000.) can add 6. and that using cellulosic ethanol lowers emissions 64%. not jet fuel) Gasohol (90% gasoline + 10% ethanol) Regular gasoline/petrol 33.6 ethanol as a fuel reduces harmful tailpipe emissions of carbon monoxide. According to the Renewable Fuels Association. Over time. which means that it cannot be efficiently shipped through modern pipelines.000 m3) of new capacity in the next 18 months.[78] More than 20% of Brazilian cars are able to use 100% ethanol as fuel. 10 (1.[73] Ethanol combustion in an internal combustion engine yields many of the products of incomplete combustion produced by gasoline and significantly larger amounts of formaldehyde and related species such as acetaldehyde.[74] This leads to a significantly larger photochemical reactivity that generates much more ground level ozone.[citation needed] When this is added into the custom Localised Pollution Index (LPI) of The Clean Fuels Report the local pollution (pollution that contributes to smog) is 1. all gasoline or any mixture of both.7 34.[82] A Ford Taurus "fueled by clean burning ethanol" owned by New York City. which includes ethanol-only engines and flex-fuel engines.wikipedia.0 and higher numbers signify greater pollution.8 46. as of October 30.14 times as much ozone as does gasoline exhaust.[77] USP grade ethanol for Ethanol pump station in São Paulo. An additional 72 construction projects underway (in the U.[79] Flex-fuel engines in Brazil are able to work with all ethanol. [citation needed] The California Air Resources Board formalized this issue in 2008 by recognizing control standards for formaldehydes as an emissions control group. Sugar cane not only has a greater concentration of sucrose than corn (by about 30%).[71] Aviation gasoline 33. In 2011.

brandies. most cars sold in the United States to be warranted to run on ethanol. distilled from fermented cereal grains. gamma-hydroxybutyric acid (GHB).Wikipedia. It has a complex mode of action and affects multiple systems in the brain. these spirits are so thoroughly distilled that no tastes from the particular starting material remain. ethyl amines. Vodka and similar neutral grain spirits can be distilled from any fermented material (grain and potatoes are most common). and to a lesser extent butadiene. Just as industrial ethanol is used as feedstock for the production of industrial acetic acid. Ethanol kills organisms by denaturing their proteins and dissolving their lipids and is effective against most bacteria and fungi. diethyl ether. a "flex-fuel" blend in Saint Paul. and spices into distilled spirits. Alcoholic beverages Main article: Alcoholic beverage Ethanol is the principal psychoactive constituent in alcoholic beverages. Broad categories of distilled beverages include whiskeys. Antiseptic Ethanol is used in medical wipes and in most common antibacterial hand sanitizer gels at a concentration of about 62% v/v as an antiseptic. alcoholic beverages are made into vinegar. acetic acid.Ethanol . the most notable one being its agonistic action on the GABA receptors. distilled from fermented molasses or sugarcane juice.[citation needed] United States Postal Service vehicle running on E85. such beverages not only are more ethanol-rich but are often sweeter than other wines. or distilled beverages. as it metabolizes into acetyl CoA. Alcoholic beverages are used in cooking for their flavors and because alcohol dissolves hydrophobic flavor compounds. The ethanol content of a beverage is usually measured in terms of the volume fraction of ethanol in the beverage. in particular methanol[86] and ethylene glycol. Wine and cider vinegar are both named for their respective source alcohols.[85] Treatment for poisoning by other alcohols Ethanol is sometimes used to treat poisoning by other. Alcoholic beverages vary considerably in ethanol content and in foodstuffs they are produced from. beverages whose preparation involves concentrating the ethanol in fermented beverages by distillation. and rum. with beer as the base beverage. Ethanol 10 of 19 11/1/2012 6:22 AM . Cultures around the world have made fermented beverages from numerous other foodstuffs. Fortified wines are prepared by adding brandy or some other distilled spirit to partially fermented wine. Minnesota. Numerous other spirits and liqueurs are prepared by infusing flavors from fruits. whereas malt vinegar is derived from beer. These include ethyl halides. distilled from fermented fruit juices. such as benzodiazepines. This kills the yeast and conserves some of the sugar in grape juice. with depressant effects on the central nervous system. more toxic alcohols. Applejack is traditionally made by freeze distillation. by which water is frozen out of fermented apple cider. as well as methanol and gasoline. The ethanol content in alcoholic beverages can be increased by means other than distillation. wines and ciders from fruit juices. Beers are made from cereal grains or other starchy materials. Ice beer (also known by the German term Eisbier or Eisbock) is also freeze-distilled. but is ineffective against bacterial spores. and meads from honey. Fermented beverages can be broadly classified by the foodstuff they are fermented from. A traditional example is gin. expressed either as a percentage or in alcoholic proof units. which is created by infusing juniper berries into a neutral grain alcohol. Feedstock Main article: Chemical derivatives of ethanol Ethanol is an important industrial ingredient and has widespread use as a base chemical for other organic compounds. beverages made by the action of yeast on sugary foodstuffs. an intermediate common with glucose and fatty acid metabolism that can be used for energy in the citric acid cycle or for biosynthesis. ethyl esters. Distilled beverages are made by distilling fermented beverages. barbiturates. leaving a more ethanol-rich liquid behind.[84] Ethanol is metabolized by the body as an energy-providing nutrient. and many viruses. Most alcoholic beverages can be broadly classified as fermented beverages.[83] Similar psychoactives include those that also interact with GABA receptors.wikipedia. The bill aims to provide enough financial incentive to find better ways to make ethanol fuel so it could compete economically against gasoline. and local and national names for various fermented beverages abound. the free encyclopedia http://en.

1% can cause intoxication. lessening metabolism into toxic aldehyde and carboxylic acid derivatives.[96] The amount of ethanol in the body is typically quantified by blood BAC BAC (g/L) (% v/v) 0.1 % Symptoms[94] Euphoria. see "Effects of alcohol on the body by dose".3–0. the removal of a large concentration of alcohol from blood may follow zero-order kinetics. Hence.Ethanol .14% Decreased blood flow to brain 0. and NMDA receptors. ethanol can be ingested to reduce the rate of methanol metabolism due to shared rate-limiting steps.5% or more is commonly fatal.4% >0. A blood level of 0. credited with beginning the space age.5 1 >1. the free encyclopedia http://en. impaired cognition Stupefaction. ethanol was used for a variety of medical purposes.[92] Nausea. nausea. which launched the first U. markers.55% Death 11 of 19 11/1/2012 6:22 AM . possible unconsciousness Possible death >0. Drug effects Pure ethanol will irritate the skin and eyes.S.[90] Alcohols fell into general disuse as more efficient rocket fuels were developed.4 3 4 >5.Wikipedia.4%. in conjunction with an oxidizer such as liquid oxygen. mixed with 25% of water to reduce the combustion chamber temperature. possible vomiting. as medicine for depression and as an anesthetic. Also.[88][89] The V-2's design team helped develop U. used ethanol. the rate-limiting steps for one substance may be in common with other substances. It is found in competes with other alcohols for the alcohol dehydrogenase enzyme.[91] The removal of ethanol through oxidation by alcohol dehydrogenase in the liver from the human body is limited. talkativeness. Methanol itself is not highly toxic. serotonin. rockets following World War II. tinctures.[citation needed] Ethanol was commonly used as fuel in early bipropellant rocket (liquid propelled) vehicles.[93] Atmospheric concentrations above one in a thousand are above the European Union Occupational exposure limits. but its metabolites formaldehyde and formic acid are. Solvent Ethanol is miscible with water and is a good general purpose solvent. Long-term use by ingestion can result in serious liver damage. such as in vodka sauce.5 0.[93] Short-term Main article: Short-term effects of alcohol Effects on the central nervous system Ethanol is a central nervous system depressant and has significant psychoactive effects in sublethal doses. including the ethanol-fueled Redstone rocket.wikipedia. relaxation Central nervous system depression. For instance.05% 0.[95] Death from ethanol consumption is possible when blood alcohol level reaches 0. and personal care products such as perfumes and deodorants. It has been known to be used as a truth drug (as hinted at by the maxim "in vino veritas"). to reduce the concentration of these harmful metabolites. the blood alcohol concentration can be used to modify the biochemistry of methanol and ethylene glycol. for specifics. Historical uses Before the development of modern medicines. impaired motor and sensory function.4%. It also appears to cause an increase in dopamine through a poorly understood process that may involve inhibiting the enzyme that breaks dopamine down. Based on its abilities to change the human consciousness. GABA. rather than having an elimination half-life. Levels of even less than 0. satellite. This means that alcohol leaves the body at a constant rate. vomiting and intoxication are symptoms of ingestion.[87] and reducing one of the more serious toxic effect of the glycols to crystallize in the kidneys. ethanol is considered a psychoactive drug. therefore. The German V-2 rocket of World War II.[89] Pharmacology Ethanol binds to acetylcholine. with unconsciousness often occurring at 0.S. Ethylene glycol poisoning can be treated in the same way.3% 0. It may also be used as a solvent or solute in cooking.

Ethanol . which is here taken as weight of ethanol per unit volume of blood. Acetaldehyde is linked to most of the clinical effects of alcohol. stupefaction. people experiencing these symptoms tend to become talkative and less inhibited.[96] Magnitude of effects Some individuals have less effective forms of one or both of the metabolizing enzymes. and may exhibit poor judgment. and metabolize ethanol more rapidly.[103] Long-term Main article: Long-term effects of alcohol Birth defects Ethanol is classified as a teratogen.[99] Most drunk driving laws governing the acceptable levels in the blood while driving or operating heavy machinery set typical upper limits of blood alcohol content (BAC) between 0. slowed cognition.[97] Prolonged heavy consumption of alcohol can cause significant permanent damage to the brain and other organs. where the acetyl can be further used to produce energy or for biosynthesis. increasing the effects of the inhibitory neurotransmitter GABA (i. According to the US National Highway Traffic Safety Administration. in 2002 about "41% of people fatally injured in traffic crashes were in alcohol related crashes". opioids. impaired sensory and motor function. and hallucinations. However. and possible death.05% and 0. Drug interactions Ethanol can intensify the sedation caused by other central nervous system depressant drugs such as barbiturates.. seizures. the product of the first step of this breakdown. See fetal alcohol syndrome. At higher dosages (BAC > 1 g/L). it is a positive allosteric modulator). Alcohol withdrawal can cause anxiety. unconsciousness.[98] The risk of a fatal car accident increases exponentially with the level of alcohol in the driver's blood. ethanol is a nutrient. The reinforcing effects of alcohol consumption are also mediated by acetaldehyde generated by catalase and other oxidizing enzymes such as cytochrome P-4502E1 in the brain.[102] is more toxic than ethanol. As such.[citation needed] Discontinuing consumption of alcohol after several years of heavy drinking can also be fatal. in general. See Alcohol consumption and health. and can experience more severe symptoms from ethanol consumption than others. The table at right summarizes the symptoms of ethanol consumption.[101] Effects on metabolism Main articles: Ethanol metabolism and Alcohol dehydrogenase Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into the acetyl in acetyl CoA by acetaldehyde dehydrogenase. it appears to play a central role in the activation of the mesolimbic dopamine system. those having acquired alcohol tolerance have a greater quantity of these enzymes. It has been shown to increase the risk of developing cirrhosis of the liver[84] and multiple forms of cancer. the free encyclopedia http://en. acetaldehyde. benzodiazepines. Acetyl CoA is the final product of both carbohydrate and fat metabolism.[100] Although acetaldehyde has been associated with some of the adverse and toxic effects of ethanol. ethanol acts as a central nervous system alcohol content (BAC).wikipedia.e. producing at progressively higher dosages. phenothiazines. Delirium tremens is a condition that requires people with a long history of heavy drinking to undertake an alcohol detoxification regimen. Small doses of ethanol. and anti-depressants. autonomic dysfunction. Ethanol acts in the central nervous system by binding to the GABA-A receptor.08%. Other effects Frequent drinking of alcoholic beverages has been shown to be a major contributing factor in cases of elevated blood levels of 12 of 19 11/1/2012 6:22 AM . However.Wikipedia. produce euphoria and relaxation.

. A. Retrieved 2007-09-03.ncbi. vol. zur volkommen Entwasserung des Weingeistes nothwendig zu beobachtenden.wikipedia. (1826) "On the mutual action of sulphuric acid and alcohol. a more accurate analysis of ethanol appears on page 300 of his 1814 paper: Théodore de Saussure (1814) "Nouvelles observations sur la composition de l'alcool et de l'éther sulfurique.Wikipedia. http://pubchem. forming an icy coating around dust grains in interstellar clouds." (http://gallica. Hennell mentions that Faraday gave him some sulfuric acid in 13 of 19 11/1/2012 6:22 AM . CRC Handbook of Chemistry and Physics (89 ed.89 8.cgi? Journal de physique. P.html) .PubChem" (http://pubchem. Robert James(1948) A short history of the art of distillation. "Ethanol . doi:10. and I find when [the resulting compound is] united with bases [it] forms a peculiar class of salts. In a footnote on page 9–55. 10. 12. ^ USA (2012-03-06). "On a new chemical theory" (http://web. On page 248. The PubChem somewhat resembling the sulphovinates [ is toxic. d'histoire naturelle et des arts. 3. 7. Long. ^ Théodore de Saussure (1807) "Mémoire sur la composition de l'alcohol et de l'éther sulfurique. ^ Couper AS (1858)." (http://books. http://news. triglycerides. (Crell's) Chemische Annalen …. Retrieved 2007-09-03. Philosophical magazine 16 (104–16). http://www. ethanol will be present in any yeast habitat.nih. Boca Raton: CRC Press. /07/0718_050718_ancientbeer.198) Lowitz dehydrated the azeotrope by mixing it with a 2:1 excess of anhydrous alkali and then distilling the mixture over low heat.1021%2Fja01489a008) . ^ Roach. de chimie. (2008). M. 1911 Encyclopædia Britannica.nlm. most show no interest or avoidance of food sources containing . 4. "9. ^ Faraday." (http://books. acetaldehyde. http://pubchem. 197 .ncbi. the free encyclopedia http://en. USA: National Center for Biotechnology Information. 6–232. ^ "Alcohol" (http://www. ^ Ballinger. /07/0718_050718_ancientbeer. Journal of the American Chemical Society 82 (4): 795. Ethanol is also widely Philsophical Transactions of the Royal Society. pages 316 .doi. David R.html.nlm.[108] Ethanol produced by symbiotic yeast can be found in Bertam Palm blossoms. 64. Although some species such as the Pentailed Treeshrew exhibit ethanol seeking behaviors.lemoyne. mutagenic.249. and carcinogenic. ^ Lide.ncbi. http://web.cgi?cid=702) .nih.image) Philosophical Transactions of the Royal Society of London 115: 440-466. 5.cgi?cid=702) . Pubchem. and on certain other products obtained during the decomposition of oil by heat. As /10. clinically and over the counter. (Report of a task that must be done for the complete dehydration of wine spirits [i.bnf.e. David R.html) (online reprint).1021/ja01489a008 ( Annales de Chimie.nlm. 89: 273-305. Ethanol can commonly be found in overripe fruit. p. J. (1825) "On new compounds of carbon and LoveToKnow. (2012).[109] Ethanol is also produced during the germination of many plants as a result of natural anerobiosis.. ^ Lide. 116. specifically. pages 240 . In his 1807 paper.[107] Natural occurrence Ethanol is a byproduct of the metabolic process of yeast.ncbi. the first metabolic product of ethanol. ^ a b as an antitussive agent." (http://books.nih. Saussure determined ethanol's composition only Beer Re-Created From Chinese Recipe" (http://news.).[110] Ethanol has been detected in outer space. 9. 1.nationalgeographic. ^ Hennell. ^ T. National Geographic News. Lowitz (1796) "Anzeige eines.nih.2. (1960).204. alcohol-water azeotrope]). Handgriffs" (http://books. with observations on the composition and properties of the resulting compound. F.354.1911encyclopedia.. 2005).nationalgeographic.Ethanol .[111] See also 1-Propanol 2. 2. ^ "Ethanol – Compound Summary" (http://pubchem.[104] Ethanol is not a carcinogen.. pages 195 .org /Alcohol.ncbi.: CRC Press/Taylor and Francis. Boca Raton.).[105][106] However. CRC Handbook of Chemistry and Physics (92(Internet) ed. but still different from them. ethyl sulfates]. Retrieved 2012-04-23. "The [sulfuric] acid combines directly with carbon and hydrogen. 6.cgi?cid=702.2-Trichloroethanol Alcoholic beverages Breathalyzer Butanol fuel Cellulosic ethanol commercialization Distilled beverages Ethenol Ethynol Isopropyl alcohol Outline of energy Rubbing alcohol Timeline of alcohol fuel References 1. Here (pp. (July 18. pp." 13. Faraday notes the action of sulfuric acid on coal gas and coal-gas distillate.

Allyn and /story.15 K determined by an accurate static method".htm) .washingtonpost. ISBN 0-911910-26-3. 30.webanswers. G. the free encyclopedia Retrieved 27 January 2011. Retrieved 2007-09-22. http://www.doi.. Joseph. Hennell produces ethanol from "sulfovinic acid" (ethyl hydrogen sulfate). et des produits qui en résultent" (http://books. N. "The Isothermal Displacement Calorimeter: Design Modifications for Measuring Exothermic Enthalpies of Mixing".2. doi:10.110187. answered 2010-12-31 23. 40. 1991. "Thermodynamic properties of aqueous non-electrolyte mixtures II. "Ethanol".org/10. 38.000403 (http://dx.J. The 100 most important chemical compounds: a reference guide (http://books.unsw. E. Centre for Water & Waste Technology. Andrew Jr. P..npr.E. Annales de chimie et de physique. 82.0021 (http://dx. Linardi VR. 817. ^ a b c d e Streitweiser. "Ethanol.12. ISBN 0-205-08452-4. J.html) .html. ^ a b c d Windholz. pages 152-186.. ^ Roberts. ^ DiPardo. etc. On page 368. Ecklund EE (1987). 2011. 27. 24. 20. Retrieved March 7. "Alcohols as Components of Transportation Fuels". "On the mutual action of sulfuric acid and 1991. (2000). Caserio.doi. Annual Review of Energy 12: 47. inc. D. 41. ^ "Encyclopedia of chemical technology". W.doi. ISBN 0-8053-8329-8. Othmer.). Robert Thornton.doe. http://www. ^ Costigan . Introduction to Organic Chemistry. Aust. ^ Pemberton RC.8-heptamethylnonane) from 0. Jacqueline /books?id=X-9FAAAAMAAJ&pg=PA365#v=onepage&q&f=false.Ethanol . Mash CJ (1978). "(Liquid + liquid) phase equilibria and critical curves of (ethanol + dodecane or tetradecane or hexadecane or 2. 34.npr. "Mills GA. 33 (10): 2103. Organic Chemistry (2nd ed. doi:10. Benjamin.htm. John D. Schneider GM (1989). ^ "Odorous Compounds – Odour Descriptions of Chemicals with Odours" ( Encyclopedia of chemical technology. 25.engineeringtoolbox. Nonato EA (1996). 35. Marjorie C. 9. "Production of fuel alcohol by Saccharomyces strains from tropical habitats".1016%2F0021-9614%2878%2990160-X) . School of Civil & Environmental Engineering. J Chem Thermodyn. Retrieved 16 January 2011. Atmospheric Emissions & Odour Laboratory. 15. 18. p. ^ Merck Index of Chemicals and Drugs. 33.) 17. Heathcock.000403) . which coal gas had dissolved and that he (Hennell) found that it contained "sulphovinic acid" (ethyl hydrogen sulfate).. New York: Wiley. Chem Eng J.C. and on the nature of the process by which ether is formed" (http://books. Georges-Simon (1828) "De l'action de l'acide sulfurique sur l'alcool.1828. J Chem Thermodyn. Annales de Chimie et de Physique. (Note: The chemical formulas in Berthelot's paper are wrong because chemists at that time used the wrong atomic masses for the Stokes RH.: Greenwood Press. 37. ^ In /books?id=1ClCAAAAcAAJ&pg=PA385#v=onepage&q&f=false) (On the formation of alcohol by means of ethylene). 29. to Carazza F.Wikipedia. Boyd. Raymond E. Biotechnology Letters 18 (11): 1351.110187." United States Department of Energy.1016/0021-9614(89)90160-2 (http://dx. MacMillan.purdue. 28.. 21 (9): 997. http://www. Zhou R. "Outlook for Biomass Ethanol Production and Demand" (http://tonto. ISBN 0-471-52669-X. doi:10. doi:10. Myers.0021) . 87 (2): 149. Vapour pressures and excess Gibbs energies for water + ethanol at 303. ISBN Kirk. Wolke (5 July 2006).com/wp-dyn/content/article/2006/07 /04/AR2006070400283.. http://tonto. (2007). A. Tuxford CW (1980). ^ Robert L. 24 April 2008. Donald /?id=0AnJU-hralEC&pg=PA122) . Mary. vol 39. Marcellin Berthelot (1855) "Sur la formation de l'alcool au moyen du bicarbure d'hydrogène" ( monographs 6575 through 6669 31. Rahway.A: Merck.php?storyId=7426827) . p.doi. Kroschwitz. and products that result from it) ISBN 0-02-418010-6. vol. "Influence of salt added to solvent on extractive distillation". ^ a b Siegel.. 813. ^ "Material Safety Data Sheet. H.1016%2FS1385-8947%2801%2900211-X) . ^ Myers. 2011. doi:10. (1976).unsw. Robert Neilson (1972). Hodges LJ. In Howe-Grant. ed. University of New South Wales.E (1991).html) . ^ Lei /10.1007%2FBF00129969) .google.6.doe. Rusty L. 21.1828. 122. 17–21. 14. 16.php?storyId=7426827. Duan Z (2002). ^ Sérullas. On page 158.. Now Surging Ahead" (http://www. ^ Hennell. Robert (2007-02-15).org/10.A.1016/0021-9614(78)90160-X (http://dx. Martha (1976). Rosa CA.doi.pdf.What is the triple point of alcohol? (http://www. Chem. "Ethanol From Cellulose: A General Review (http://www. Ecklund.1 MPa to 120. ^ Mills. ^ Lodgsdon. ^ "Flash points of ethanol-based water solutions" (http://www. http://www. The Merck index: an encyclopedia of chemicals and drugs (9th ed.washingtonpost.html. Retrieved June 23. ^ "Flash Point and Fire Point" (http://www. doi:10.1016/S1385-8947(01)00211-X (http://dx. e.1007/BF00129969 (http://dx. Section 5" ( oxygen (8 instead of 16). 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de/VogelCalculation / A look into the history of ethanol ChemSub Online: Ethyl alcohol (http://chemsub.php?title=Ethanol&oldid=520299664" Categories: Alcohol Alcohols Alcohol solvents Anatomical preservation Anxiolytics Disinfectants Drugs Ethanol Household chemicals NMDA receptor antagonists Oxygenates Rocket fuels Teratogens This page was last modified on 28 October 2012 at Thermophysical properties of mixtures of ethanol with water and dodecane Excess volume of the mixture of ethanol and water (volume contraction) Heat of mixing of the mixture of ethanol and water Vapor-liquid equilibrium of the mixture of ethanol and water (including azeotrope) Solid-liquid equilibrium of the mixture of ethanol and water (including eutecticum) Miscibility gap in the mixture of dodecane and ethanol External links International Labour Organization (http://www.htm) ethanol safety information National Pollutant Inventory – Ethanol Fact Sheet ( .exe?component=Ethanol) .de/AntoineCalculation /AntoineCalculationCGI.nlm.ddbst. dynamic liquid viscosity ( liquid density (http://ddbonline.html) Retrieved from "http://en.nih.exe?component=Ethanol) .do?chebiId=CHEBI:16236) Chicago Board of Trade ( National Institute of Standards and Technology (http://webbook.ddbst.cgi?Name=ethanol&Units=SI) chemical data on ethanol ChEBI – biology related (http://www.Wikipedia.ethanolhistory. 18 of 19 11/1/2012 6:22 AM /DIPPR106SFTCalculationCGI. surface tension (http://ddbonline.Ethanol .com/) news and market data on ethanol futures Calculation of vapor pressure ( /DIPPR105CalculationCGI.npi. the free encyclopedia /dpdirect. National Library of Medicine: Drug Information Portal – Ethanol (http://druginfo.jsp?name=Ethanol) Ethanol History ( of ethanol

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