Wikipedia

Ethanol

For ethanol as a drug or medicine, seeAlcohol (drug)andAlcohols (medicine).
Not to be confused withEthenolorEthynol.

Ethanol(also calledethyl alcohol,grain alcohol,drinking alcohol,or simplyalcohol) is anorganic compoundwith thechemical formulaCH3CH2OH.It is analcohol,with its formula also written asC2H5OH,C2H6Oor EtOH, where Et stands forethyl.Ethanol is avolatile,flammable,colorless liquid with a characteristicwine-like odor andpungenttaste.[13][14]As apsychoactivedepressant,it is the active ingredient inalcoholic drinks,and the second most consumed drug globally behindcaffeine.[15]

Ethanol
Full structural formula of ethanol
Full structural formula of ethanol
Skeletal formula of ethanol
Skeletal formula of ethanol
Ball-and-stick model of ethanol
Ball-and-stick model of ethanol
Space-filling model of ethanol
Space-filling model of ethanol
Names
Pronunciation /ˈɛθənɒl/
Preferred IUPAC name
Ethanol[1]
Other names
  • Absolute alcohol
  • Alcohol
  • Cologne spirit
  • Drinking alcohol
  • Ethylic alcohol
  • EtOH
  • Ethyl alcohol
  • Ethyl hydroxide
  • Ethylene hydrate
  • Ethylol
  • Grain alcohol
  • Hydroxyethane
  • Methylcarbinol
Identifiers
3D model (JSmol)
3DMet
1718733
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.526Edit this at Wikidata
787
KEGG
UNII
UN number UN 1170
  • InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3checkY
    Key: LFQSCWFLJHTTHZ-UHFFFAOYSA-NcheckY
  • InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3
    Key: LFQSCWFLJHTTHZ-UHFFFAOYAB
  • OCC
Properties
C2H6O
Molar mass 46.069g·mol−1
Appearance Colourless liquid
Odor wine-like, pungent[2]
Density 0.78945 g/cm3(at 20 °C)[3]
Melting point −114.14 ± 0.03[3]°C (−173.45 ± 0.05 °F; 159.01 ± 0.03 K)
Boiling point 78.23 ± 0.09[3]°C (172.81 ± 0.16 °F; 351.38 ± 0.09 K)
Miscible
logP −0.18
Vapor pressure 5.95 kPa (at 20 °C)
Acidity(pKa) 15.9 (H2O), 29.8 (DMSO)[4][5]
−33.60·10−6cm3/mol
1.3611[3]
Viscosity 1.2 mPa·s (at 20 °C), 1.074 mPa·s (at 25 °C)[6]
1.69 D[7]
Hazards
GHSlabelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H225,H319,H360D
P210,P233,P240,P241,P242,P305+P351+P338
NFPA 704(fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 14 °C (Absolute)[9]
Lethal doseor concentration (LD, LC):
  • 7060mg/kg (oral, rat)
  • 3450mg/kg (mouse)
[12]
NIOSH(US health exposure limits):
PEL(Permissible)
 TWA 1000 ppm (1900mg/m3)[10]
REL(Recommended)
 TWA 1000 ppm (1900mg/m3)[10]
IDLH(Immediate danger)
 3300 ppm[11]
Safety data sheet(SDS) [8]
Related compounds
Related compounds
Supplementary data page
Ethanol (data page)
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Ethanol is naturally produced by thefermentationprocess ofsugarsbyyeastsor viapetrochemicalprocesses such asethylenehydration. Historically it was used as ageneral anesthetic,and has modern medical applications as anantiseptic,disinfectant,solvent for some medications, andantidoteformethanol poisoningandethylene glycol poisoning.[16][17]It is used as a chemicalsolventand in thesynthesisoforganic compounds,and as afuel source.Ethanol also can be dehydrated to makeethylene,an important chemical feedstock. As of 2023, world production of ethanol was 29,590,000,000 US gallons (112.0 gigalitres), coming mostly from the U.S. (51%) and Brazil (26%).[18]

Etymology

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Ethanolis thesystematic namedefinedby theInternational Union of Pure and Applied Chemistryfor a compound consisting of analkyl groupwith two carbonatoms(prefix "eth-" ), having a single bond between them (infix "-an-" ) and an attached −OHfunctional group(suffix "-ol" ).[19]

The "eth-" prefix and the qualifier "ethyl" in "ethyl alcohol" originally came from the name "ethyl" assigned in 1834 to the groupC
2H
5− byJustus Liebig.He coined the word from theGermannameAetherof the compoundC
2H
5−O−C
2H
5(commonly called "ether" inEnglish,more specifically called "diethyl ether").[20]According to theOxford English Dictionary,Ethylis a contraction of the Ancient Greekαἰθήρ(aithḗr,"upper air" ) and the Greek wordὕλη(hýlē,"wood, raw material", hence "matter, substance" ).[21]

The nameethanolwas coined as a result of a resolution on naming alcohols and phenols that was adopted at the International Conference onChemical Nomenclaturethat was held in April 1892 inGeneva,Switzerland.[22]

The termalcoholnow refers to a wider class of substances in chemistry nomenclature, but in common parlance it remains the name of ethanol. It is a medieval loan fromArabical-kuḥl,a powdered ore ofantimonyused since antiquity as a cosmetic, and retained that meaning inMiddle Latin.[23]The use of 'alcohol' for ethanol (in full, "alcohol of wine" ) is modern and was first recorded in 1753. Before the late 18th century the term "alcohol" generally referred to any sublimated substance.[24]

Uses

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Medical

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Main article:Alcohol (medicine)

Anesthetic

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Ethanol is the oldest knownsedative,used as an oralgeneral anestheticduring surgery in ancientMesopotamiaand inmedieval times.[16][17]Mild intoxication starts at ablood alcohol concentrationof 0.03-0.05 % and inducesanesthetic comaat 0.4%.[25]However, this use carried the high risk of deadlyalcohol intoxicationandpulmonary aspirationon vomit, which led to use of alternatives in antiquity, such asopiumandcannabis,and laterdiethyl etherstarting in the 1840s.[26]

Antiseptic

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Ethanol is used in medical wipes and most commonly in antibacterialhand sanitizergels as anantisepticfor its bactericidal and anti-fungal effects.[27]Ethanol killsmicroorganismsby dissolving their membranelipid bilayeranddenaturingtheirproteins,and is effective against mostbacteria,fungiandviruses.However, it is ineffective against bacterialspores,but that can be alleviated by usinghydrogen peroxide.[28]

A solution of 70% ethanol is more effective than pure ethanol because ethanol relies on water molecules for optimal antimicrobial activity. Absolute ethanol may inactivate microbes without destroying them because the alcohol is unable to fully permeate the microbe's membrane.[29][30]Ethanol can also be used as a disinfectant and antiseptic because it causes cell dehydration by disrupting the osmotic balance across the cell membrane, so water leaves the cell leading to cell death.[31]

Antidote

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Ethanol may be administered as anantidotetoethylene glycol poisoning[32]andmethanol poisoning.[33]Ethanol serves this process by acting as acompetitive inhibitoragainstmethanolandethylene glycolforalcohol dehydrogenase.[34]Though it has more side effects, ethanol is less expensive and more readily available thanfomepizole,which is also used as an antidote for methanol and ethylene glycol poisoning.[35]

Medicinal solvent

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Ethanol, often in high concentrations, is used to dissolve many water-insoluble medications and related compounds. Liquid preparations ofpain medications,cough and cold medicines,and mouth washes, for example, may contain up to 25% ethanol[36]and may need to be avoided in individuals with adverse reactions to ethanol such asalcohol-induced respiratory reactions.[37]Ethanol is present mainly as an antimicrobial preservative in over 700 liquid preparations of medicine includingacetaminophen,iron supplements,ranitidine,furosemide,mannitol,phenobarbital,trimethoprim/sulfamethoxazoleandover-the-countercough medicine.[38]

Some medicinal solutions of ethanol are also known astinctures.

Pharmacology

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In mammals, ethanol is primarilymetabolizedin theliverandstomachbyalcohol dehydrogenase(ADH) enzymes.[39]These enzymes catalyze theoxidationof ethanol intoacetaldehyde(ethanal):[40]

CH3CH2OH + NAD+→ CH3CHO +NADH+ H+

When present in significant concentrations, this metabolism of ethanol is additionally aided by thecytochrome P450enzymeCYP2E1in humans, while trace amounts are also metabolized bycatalase.[41]

The resulting intermediate, acetaldehyde, is a known carcinogen, and poses significantly greater toxicity in humans than ethanol itself. Many of the symptoms typically associated with alcohol intoxication—as well as many of the health hazards typically associated with the long-term consumption of ethanol—can be attributed to acetaldehyde toxicity in humans.[42]

The subsequent oxidation of acetaldehyde into acetate is performed byaldehyde dehydrogenase(ALDH) enzymes. A mutation in the ALDH2 gene that encodes for an inactive or dysfunctional form of this enzyme affects roughly 50 % of east Asian populations, contributing to the characteristicalcohol flush reactionthat can cause temporary reddening of the skin as well as a number of related, and often unpleasant, symptoms of acetaldehyde toxicity.[43]This mutation is typically accompanied by another mutation in thealcohol dehydrogenaseenzymeADH1Bin roughly 80 % of east Asians, which improves the catalytic efficiency of converting ethanol into acetaldehyde.[43]

Recreational

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Main articles:Alcohol (drug)andAlcoholic drink

As acentral nervous systemdepressant,ethanol is one of the most commonly consumedpsychoactive drugs.[44]

Despite alcohol's psychoactive, addictive, andcarcinogenicproperties, it is readily available and legal for sale in most countries. There are laws regulating the sale, exportation/importation, taxation, manufacturing, consumption, and possession of alcoholic beverages. The most common regulation is prohibition for minors.

Fuel

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See also:Food vs. fuel
Corn vs ethanol production in the United States
Total corn production (bushels) (left)
Corn used forEthanol fuel(bushels) (left)
Percent of corn used for Ethanol (right)

Engine fuel

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Main article:Ethanol fuel
Energy content(lower heating value) of some fuels compared with ethanol.
Fuel type MJ/L MJ/kg Research
octane
number
Dry wood (20% moisture) ~19.5
Methanol 17.9 19.9 108.7[45]
Ethanol 21.2[46] 26.8[46] 108.6[45]
E85
(85% ethanol, 15% gasoline)		 25.2 33.2 105
Liquefied natural gas 25.3 ~55
Autogas(LPG)
(60%propane+ 40%butane)		 26.8 50
Aviation gasoline
(high-octane gasoline, not jet fuel)		 33.5 46.8 100/130 (lean/rich)
Gasohol
(90% gasoline + 10% ethanol)		 33.7 47.1 93/94
Regular gasoline/petrol 34.8 44.4[47] min. 91
Premium gasoline/petrol max. 104
Diesel 38.6 45.4 25
Charcoal,extruded 50 23

The largest single use of ethanol is as an enginefuelandfuel additive.Brazilin particular relies heavily upon the use of ethanol as an engine fuel, due in part to its role as one of the world's leading producers of ethanol.[48][49]Gasolinesold in Brazil contains at least 25%anhydrousethanol. Hydrous ethanol (about 95% ethanol and 5% water) can be used as fuel in more than 90% of new gasoline-fueled cars sold in the country.

The US and many other countries primarily use E10 (10% ethanol, sometimes known as gasohol) and E85 (85% ethanol) ethanol/gasoline mixtures. Over time, it is believed that a material portion of the ≈150-billion-US-gallon (570,000,000 m3) per year market for gasoline will begin to be replaced with fuel ethanol.[50]

USP gradeethanol for laboratory use

Australian law limits the use of pure ethanol fromsugarcanewaste to 10 % in automobiles. Older cars (and vintage cars designed to use a slower burning fuel) should have the engine valves upgraded or replaced.[51]

According to an industryadvocacy group,ethanol as a fuel reduces harmfultailpipe emissionsof carbon monoxide, particulate matter,oxides of nitrogen,and other ozone-forming pollutants.[52]Argonne National Laboratoryanalyzed greenhouse gas emissions of many different engine and fuel combinations, and found thatbiodiesel/petrodiesel blend (B20) showed a reduction of 8%, conventionalE85ethanol blend a reduction of 17% andcellulosic ethanol64%, compared with pure gasoline.[53]Ethanol has a much greater research octane number (RON) than gasoline, meaning it is less prone to pre-ignition, allowing for better ignition advance which means more torque, and efficiency in addition to the lower carbon emissions.[54]

Ethanolcombustionin aninternal combustion engineyields many of the products of incomplete combustion produced by gasoline and significantly larger amounts offormaldehydeand related species such as acetaldehyde.[55]This leads to a significantly larger photochemical reactivity and moreground level ozone.[56]This data has been assembled into The Clean Fuels Report comparison of fuel emissions[57]and show that ethanol exhaust generates 2.14 times as much ozone as gasoline exhaust.[58]When this is added into the customLocalized Pollution Indexof The Clean Fuels Report, the local pollution of ethanol (pollution that contributes to smog) is rated 1.7, where gasoline is 1.0 and higher numbers signify greater pollution.[59]TheCalifornia Air Resources Boardformalized this issue in 2008 by recognizing control standards for formaldehydes as an emissions control group, much like the conventionalNOxand reactive organic gases (ROGs).[60]

More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanol-only engines andflex-fuelengines.[61]Flex-fuel engines in Brazil are able to work with all ethanol, all gasoline or any mixture of both. In the United States, flex-fuel vehicles can run on 0% to 85% ethanol (15% gasoline) since higher ethanol blends are not yet allowed or efficient. Brazil supports this fleet of ethanol-burning automobiles with large national infrastructure that produces ethanol from domestically grown sugarcane.

Ethanol's highmiscibilitywith water makes it unsuitable for shipping through modernpipelineslike liquid hydrocarbons.[62]Mechanics have seen increased cases of damage to small engines (in particular, thecarburetor) and attribute the damage to the increased water retention by ethanol in fuel.[63]

Ethanol pump station inSão Paulo,Brazil
AFord Taurusfueled by ethanol inNew York City
U.S. Postal Servicetruck running onE85inMinnesota

Rocket fuel

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Ethanol was commonly used as fuel in earlybipropellantrocket(liquid-propelled) vehicles, in conjunction with anoxidizersuch as liquid oxygen. The German A-4 ballistic rocket ofWorld War II(better known by its propaganda nameV-2),[64]which is credited as having begun the space age, used ethanol as the main constituent ofB-Stoff.Under such nomenclature, the ethanol was mixed with 25% water to reduce the combustion chamber temperature.[65][66]TheV-2'sdesign team helped develop U.S. rockets following World War II, including the ethanol-fueledRedstone rocket,which launched the first U.S. satellite.[67]Alcohols fell into general disuse as more energy-dense rocket fuels were developed,[66]although ethanol is currently used inlightweightrocket-powered racing aircraft.[68]

Fuel cells

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Commercial fuel cells operate on reformed natural gas,hydrogenor methanol. Ethanol is an attractive alternative due to its wide availability, low cost, high purity and low toxicity. There is a wide range of fuel cell concepts that have entered trials includingdirect-ethanol fuel cells,auto-thermal reforming systems and thermally integrated systems. The majority of work is being conducted at a research level although there are a number of organizations at the beginning of the commercialization of ethanol fuel cells.[69]

Household heating and cooking

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Ethanol fireplaces can be used for home heating or for decoration. Ethanol can also be used as stove fuel for cooking.[70][71]

Feedstock

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Further information:§ Reactions

Ethanol is an important industrial ingredient. It has widespread use as a precursor for other organic compounds such as ethylhalides,ethylesters,diethyl ether, acetic acid, and ethylamines.

Solvent

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Ethanol is considered a universalsolvent,as itsmolecularstructure allows for the dissolving of bothpolar,hydrophilicandnonpolar,hydrophobiccompounds. As ethanol also has a lowboiling point,it is easy to remove from a solution that has been used to dissolve other compounds, making it a popular extracting agent for botanical oils.Cannabis oilextraction methods often use ethanol as an extraction solvent,[72]and also as a post-processing solvent to remove oils, waxes, andchlorophyllfrom solution in a process known aswinterization.

Ethanol is found inpaints,tinctures,markers, and personal care products such as mouthwashes, perfumes and deodorants.Polysaccharidesprecipitatefrom aqueous solution in the presence of alcohol, and ethanol precipitation is used for this reason in the purification ofDNAandRNA.

Low-temperature liquid

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Because of its lowfreezing pointof −114 °C (−173 °F) and low toxicity, ethanol is sometimes used in laboratories (withdry iceor other coolants) as acooling bathto keep vessels at temperatures below the freezing point of water. For the same reason, it is also used as the active fluid inalcohol thermometers.

Chemistry

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Further information:Ethanol (data page)

Chemical formula

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Ethanol is a 2-carbonalcohol.Itsmolecular formulais CH3CH2OH. The structure of the molecule of ethanol isCH3−CH2−OH(anethyl grouplinked to ahydroxyl group), which indicates that the carbon of amethyl group(CH3−) is attached to the carbon of amethylene group(−CH2–), which is attached to the oxygen of a hydroxyl group (−OH). It is a constitutionalisomerofdimethyl ether.Ethanol is sometimes abbreviated asEtOH,using the common organic chemistry notation of representing the ethyl group (C2H5−) withEt.

Physical properties

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Ethanol burning with its spectrum depicted

Ethanol is a volatile, colorless liquid that has a slight odor. It burns with a smokeless blue flame that is not always visible in normal light. The physical properties of ethanol stem primarily from the presence of its hydroxyl group and the shortness of its carbon chain. Ethanol's hydroxyl group is able to participate in hydrogen bonding, rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight, such aspropane.

Ethanol'sadiabatic flame temperaturefor combustion in air is 2082 °C or 3779 °F.[73]

Ethanol is slightly more refractive than water, having arefractive indexof 1.36242 (at λ=589.3 nm and 18.35 °C or 65.03 °F).[74]Thetriple pointfor ethanol is150 ± 20K.[75]

Solvent properties

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Ethanol is a versatile solvent,misciblewith water and with many organic solvents, includingacetic acid,acetone,benzene,carbon tetrachloride,chloroform,diethyl ether,ethylene glycol,glycerol,nitromethane,pyridine,andtoluene.Its main use as a solvent is in making tincture of iodine, cough syrups, etc.[74][76]It is also miscible with light aliphatic hydrocarbons, such aspentaneandhexane,and with aliphatic chlorides such astrichloroethaneandtetrachloroethylene.[76]

Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as the number of carbons increases.[77]The miscibility of ethanol withalkanesis limited to alkanes up toundecane:mixtures withdodecaneand higher alkanes show amiscibility gapbelow a certain temperature (about 13 °C for dodecane[78]). The miscibility gap tends to get wider with higher alkanes, and the temperature for complete miscibility increases.

Ethanol-water mixtures have less volume than the sum of their individual components at the given fractions. Mixing equal volumes of ethanol and water results in only 1.92 volumes of mixture.[74][79]Mixing ethanol and water isexothermic,with up to 777 J/mol[80]being released at 298 K.

Mixtures of ethanol and water form anazeotropeat about 89 mole-% ethanol and 11 mole-% water[81]or a mixture of 95.6% ethanol by mass (or about 97%alcohol by volume) at normal pressure, which boils at 351 K (78 °C). This azeotropic composition is strongly temperature- and pressure-dependent and vanishes at temperatures below 303 K.[82]

Hydrogen bonding in solid ethanol at −186 °C

Hydrogen bonding causes pure ethanol to behygroscopicto the extent that it readily absorbs water from the air. The polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds, notablysodiumandpotassium hydroxides,magnesium chloride,calcium chloride,ammonium chloride,ammonium bromide,andsodium bromide.[76]Sodiumandpotassium chloridesare slightly soluble in ethanol.[76]Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including mostessential oils[83]and numerous flavoring, coloring, and medicinal agents.

The addition of even a few percent of ethanol to water sharply reduces thesurface tensionof water. This property partially explains the "tears of wine"phenomenon. When wine is swirled in a glass, ethanol evaporates quickly from the thin film of wine on the wall of the glass. As the wine's ethanol content decreases, its surface tension increases and the thin film" beads up "and runs down the glass in channels rather than as a smooth sheet.

Flammability

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An ethanol–water solution will catch fire if heated above a temperature called itsflash pointand an ignition source is then applied to it.[84]For 20% alcohol by mass (about 25% by volume), this will occur at about 25 °C (77 °F). The flash point of pure ethanol is 13 °C (55 °F),[85]but may be influenced very slightly by atmospheric composition such as pressure and humidity. Ethanol mixtures can ignite below average room temperature. Ethanol is considered a flammable liquid (Class 3 Hazardous Material) in concentrations above 2.35% by mass (3.0% by volume; 6proof).[86][87][88]

Flash points of ethanol–water mixtures[89][87][90]
Ethanol
mole fraction,% 		Temperature
°C °F
1 84.5 184.1[87]
2 64 147[87]
2.35 60 140[87][86]
3 51.5 124.7[87]
5 43 109[89]
6 39.5 103.1[87]
10 31 88[89]
20 25 77[87]
30 24 75[89]
50 20 68[89][87]
70 16 61[89]
80 15.8 60.4[87]
90 14 57[89]
100 12.5 54.5[89][87][85]

Dishes using burning alcohol for culinary effects are calledflambé.

Natural occurrence

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Ethanol is a byproduct of the metabolic process of yeast. As such, ethanol will be present in any yeast habitat. Ethanol can commonly be found in overripe fruit.[91]Ethanol produced by symbiotic yeast can be found inbertam palmblossoms. Although some animal species, such as thepentailed treeshrew,exhibit ethanol-seeking behaviors, most show no interest or avoidance of food sources containing ethanol.[92]Ethanol is also produced during the germination of many plants as a result of naturalanaerobiosis.[93]

Ethanol has been detected inouter space,forming an icy coating around dust grains ininterstellar clouds.[94] Minute quantity amounts (average 196ppb) of endogenous ethanol and acetaldehyde were found in the exhaled breath of healthy volunteers.[95]Auto-brewery syndrome,also known as gut fermentation syndrome, is a rare medical condition in whichintoxicatingquantities of ethanol are produced throughendogenousfermentationwithin thedigestive system.[96]

Production

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94% denatured ethanol sold in a bottle for household use

Ethanol is produced both as apetrochemical,through the hydration ofethyleneand, via biological processes, by fermentingsugarswithyeast.[97]Which process is more economical depends on prevailing prices ofpetroleumand grain feed stocks.

Sources

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World production of ethanol in 2006 was 51 gigalitres (1.3×1010US gal), with 69% of the world supply coming from Brazil and the U.S.[18]Brazilian ethanol is produced from sugarcane, which has relatively high yields (830% more fuel than the fossil fuels used to produce it) compared to some otherenergy crops.[98]Sugarcane not only has a greater concentration of sucrose than corn (by about 30%), but is also much easier to extract. Thebagassegenerated by the process is not discarded, but burned by power plants to produce electricity. Bagasse burning accounts for around 9% of the electricity produced in Brazil.[99]

In the 1970s most industrial ethanol in the U.S. was made as a petrochemical, but in the 1980s the U.S. introduced subsidies forcorn-based ethanol.[100]According to the Renewable Fuels Association, as of 30 October 2007, 131 grain ethanol bio-refineries in the U.S. have the capacity to produce 7×10^9US gal (26,000,000 m3) of ethanol per year. An additional 72 construction projects underway (in the U.S.) can add 6.4 billion US gallons (24,000,000 m3) of new capacity in the next 18 months.[50]

In India ethanol is made from sugarcane.[101]Sweet sorghumis another potential source of ethanol, and is suitable for growing in dryland conditions. TheInternational Crops Research Institute for the Semi-Arid Tropicsis investigating the possibility of growing sorghum as a source of fuel, food, and animal feed in arid parts ofAsiaandAfrica.[102]Sweet sorghum has one-third the water requirement of sugarcane over the same time period. It also requires about 22% less water than corn. The world's first sweet sorghum ethanol distillery began commercial production in 2007 inAndhra Pradesh,India.[103]

Hydration

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Ethanol can be produced frompetrochemicalfeed stocks, primarily by theacid-catalyzedhydrationofethylene.It is often referred to as synthetic ethanol.

C2H4+ H2O → C2H5OH

The catalyst is most commonlyphosphoric acid,[104][105]adsorbedonto a porous support such assilica gelordiatomaceous earth.This catalyst was first used for large-scale ethanol production by theShell Oil Companyin 1947.[106]The reaction is carried out in the presence of high pressure steam at 300 °C (572 °F) where a 5:3 ethylene to steam ratio is maintained.[107][108]This process was used on an industrial scale byUnion CarbideCorporation and others. It is no longer practiced in the US as fermentation ethanol produced from corn is more economical.[109]

In an older process, first practiced on the industrial scale in 1930 by Union Carbide[110]but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentratedsulfuric acidto produceethyl sulfate,which washydrolyzedto yield ethanol and regenerate the sulfuric acid:[111]

C2H4+ H2SO4→ C2H5HSO4
C2H5HSO4+ H2O → H2SO4+ C2H5OH

From carbon dioxide

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Ethanol has been produced in the laboratory by convertingcarbon dioxidevia biological andelectrochemicalreactions.[112][113]

CO2+H
2O→CH
3CH
2OH + side products

Fermentation

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Main article:Ethanol fermentation
See also:Yeast in winemaking

Ethanol inalcoholic beveragesand fuel is produced by fermentation. Certain species of yeast (e.g.,Saccharomyces cerevisiae) metabolize sugar (namelypolysaccharides), producing ethanol and carbon dioxide. The chemical equations below summarize the conversion:

C
6H
12O
6→ 2CH
3CH
2OH + 2 CO2
C
12H
22O
11+H
2O→ 4CH
3CH
2OH + 4 CO2

Fermentation is the process of culturing yeast under favorable thermal conditions to produce alcohol. This process is carried out at around 35–40 °C (95–104 °F). Toxicity of ethanol to yeast limits the ethanol concentration obtainable by brewing; higher concentrations, therefore, are obtained byfortificationordistillation.The most ethanol-tolerant yeast strains can survive up to approximately 18% ethanol by volume.

To produce ethanol from starchy materials such ascereals,thestarchmust first be converted into sugars. In brewingbeer,this has traditionally been accomplished by allowing the grain to germinate, ormalt,which produces theenzymeamylase.When the malted grain ismashed,the amylase converts the remaining starches into sugars.

Cellulose

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Main article:Cellulosic ethanol

Sugars forethanol fermentationcan be obtained fromcellulose.Deployment of this technology could turn a number of cellulose-containing agricultural by-products, such ascorncobs,straw,andsawdust,into renewable energy resources. Other agricultural residues such as sugarcane bagasse andenergy cropssuch asswitchgrassmay also be fermentable sugar sources.[114]

Testing

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Infrared reflection spectra of liquid ethanol, showing the −OH band centered near 3300 cm−1and C−H bands near 2950 cm−1
Near-infrared spectrumof liquid ethanol

Breweries andbiofuelplants employ two methods for measuring ethanol concentration. Infrared ethanol sensors measure the vibrational frequency of dissolved ethanol using the C−H band at 2900 cm−1.This method uses a relatively inexpensive solid-state sensor that compares the C−H band with a reference band to calculate the ethanol content. The calculation makes use of theBeer–Lambert law.Alternatively, by measuring the density of the starting material and the density of the product, using ahydrometer,the change in specific gravity during fermentation indicates the alcohol content. This inexpensive and indirect method has a long history in the beer brewing industry.

Purification

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Distillation

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Ethylene hydration or brewing produces an ethanol–water mixture. For most industrial and fuel uses, the ethanol must be purified.Fractional distillationat atmospheric pressure can concentrate ethanol to 95.6% by weight (89.5 mole%). This mixture is anazeotropewith a boiling point of 78.1 °C (172.6 °F), andcannotbe further purified by distillation. Addition of an entraining agent, such asbenzene,cyclohexane,orheptane,allows a new ternary azeotrope comprising the ethanol, water, and the entraining agent to be formed. This lower-boiling ternary azeotrope is removed preferentially, leading to water-free ethanol.[105]

Molecular sieves and desiccants

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Apart from distillation, ethanol may be dried by addition of adesiccant,such asmolecular sieves,cellulose,orcornmeal.The desiccants can be dried and reused.[105]Molecular sievescan be used to selectively absorb the water from the 95.6% ethanol solution.[115]Molecular sieves of pore-size 3Ångstrom,a type ofzeolite,effectively sequester water molecules while excluding ethanol molecules. Heating the wet sieves drives out the water, allowing regeneration of their desiccant capability.[116]

Membranes and reverse osmosis

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Membranes can also be used to separate ethanol and water. Membrane-based separations are not subject to the limitations of the water-ethanol azeotrope because the separations are not based on vapor-liquid equilibria. Membranes are often used in the so-called hybrid membrane distillation process. This process uses a pre-concentration distillation column as the first separating step. The further separation is then accomplished with a membrane operated either in vapor permeation or pervaporation mode. Vapor permeation uses a vapor membrane feed and pervaporation uses a liquid membrane feed.

Other techniques

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A variety of other techniques have been discussed, including the following:[105]

Grades of ethanol

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Denatured alcohol

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Main article:Denatured alcohol

Pure ethanol and alcoholic beverages are heavilytaxedas psychoactive drugs, but ethanol has many uses that do not involve its consumption. To relieve the tax burden on these uses, most jurisdictions waive the tax when an agent has been added to the ethanol to render it unfit to drink. These includebittering agentssuch asdenatonium benzoateand toxins such as methanol,naphtha,andpyridine.Products of this kind are calleddenatured alcohol.[119][120]

Absolute alcohol

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Absolute or anhydrous alcohol refers to ethanol with a low water content. There are various grades with maximum water contents ranging from 1% to a few parts per million (ppm). Ifazeotropic distillationis used to remove water, it will contain trace amounts of the material separation agent (e.g. benzene).[121]Absolute alcohol is not intended for human consumption. Absolute ethanol is used as a solvent for laboratory and industrial applications, where water will react with other chemicals, and as fuel alcohol. Spectroscopic ethanol is an absolute ethanol with a low absorbance inultravioletand visible light, fit for use as a solvent inultraviolet-visible spectroscopy.[122]

Pure ethanol is classed as 200proofin the US, equivalent to 175 degrees proof in the UK system.[123]

Rectified spirits

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Rectified spirit, an azeotropic composition of 96% ethanol containing 4% water, is used instead of anhydrous ethanol for various purposes. Spirits of wine are about 94% ethanol (188 proof). The impurities are different from those in 95% (190 proof) laboratory ethanol.[124]

Reactions

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Further information:Alcohol (chemistry)

Ethanol is classified as a primary alcohol, meaning that the carbon that its hydroxyl group attaches to has at least two hydrogen atoms attached to it as well. Many ethanol reactions occur at its hydroxyl group.

Ester formation

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In the presence of acid catalysts, ethanol reacts withcarboxylic acidsto produce ethylestersand water:

RCOOH+ HOCH2CH3→RCOOCH2CH3+ H2O

This reaction, which is conducted on large scale industrially, requires the removal of the water from the reaction mixture as it is formed. Esters react in the presence of an acid or base to give back the alcohol and a salt. This reaction is known assaponificationbecause it is used in the preparation of soap. Ethanol can also form esters with inorganic acids.Diethyl sulfateandtriethyl phosphateare prepared by treating ethanol with sulfur trioxide andphosphorus pentoxiderespectively. Diethyl sulfate is a useful ethylating agent inorganic synthesis.Ethyl nitrite,prepared from the reaction of ethanol withsodium nitriteand sulfuric acid, was formerly used as adiuretic.

Dehydration

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In the presence of acid catalysts, alcohols can be converted to alkenes such as ethanol to ethylene. Typicallysolid acidssuch asaluminaare used.[125]

CH3CH2OH → H2C=CH2+ H2O

Since water is removed from the same molecule, the reaction is known asintramolecular dehydration.Intramolecular dehydration of an alcohol requires a high temperature and the presence of an acid catalyst such assulfuric acid.[126]

Ethylene produced from sugar-derived ethanol (primarily in Brazil) competes with ethylene produced from petrochemical feedstocks such as naphtha and ethane.

At a lower temperature than that of intramolecular dehydration,intermolecular alcohol dehydrationmay occur producing a symmetrical ether. This is acondensation reaction.In the following example,diethyl etheris produced from ethanol:

2 CH3CH2OH → CH3CH2OCH2CH3+ H2O[127]

Combustion

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Complete combustion of ethanol forms carbon dioxide and water:

C2H5OH (l) + 3 O2(g) → 2 CO2(g) + 3 H2O (l); −ΔcH= 1371 kJ/mol[128]= 29.8 kJ/g = 327 kcal/mol = 7.1 kcal/g
C2H5OH (l) + 3 O2(g) → 2 CO2(g) + 3 H2O (g); −ΔcH= 1236 kJ/mol = 26.8 kJ/g = 295.4 kcal/mol = 6.41 kcal/g[129]

Specific heat = 2.44 kJ/(kg·K)

Acid-base chemistry

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Ethanol is a neutral molecule and thepHof a solution of ethanol in water is nearly 7.00. Ethanol can be quantitatively converted to itsconjugate base,theethoxideion (CH3CH2O−), by reaction with analkali metalsuch assodium:[77]

2 CH3CH2OH + 2 Na → 2 CH3CH2ONa + H2

or a very strong base such assodium hydride:

CH3CH2OH + NaH → CH3CH2ONa + H2

The acidities of water and ethanol are nearly the same, as indicated by theirpKaof 15.7 and 16 respectively. Thus, sodium ethoxide andsodium hydroxideexist in an equilibrium that is closely balanced:

CH3CH2OH + NaOH ⇌ CH3CH2ONa + H2O

Halogenation

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Ethanol is not used industrially as a precursor to ethyl halides, but the reactions are illustrative. Ethanol reacts withhydrogen halidesto produceethyl halidessuch asethyl chlorideandethyl bromidevia anSN2 reaction:

CH3CH2OH +HCl→ CH3CH2Cl + H2O

HCl requires a catalyst such aszinc chloride.[111] HBr requiresrefluxingwith asulfuric acidcatalyst.[111]Ethyl halides can, in principle, also be produced by treating ethanol with more specializedhalogenating agents,such asthionyl chlorideorphosphorus tribromide.[77][111]

CH3CH2OH + SOCl2→ CH3CH2Cl + SO2+ HCl

Upon treatment with halogens in the presence of base, ethanol gives the correspondinghaloform(CHX3,where X = Cl, Br, I). This conversion is called thehaloform reaction.[130] An intermediate in the reaction with chlorine is thealdehydecalledchloral,which formschloral hydrateupon reaction with water:[131]

4 Cl2+ CH3CH2OH → CCl3CHO + 5 HCl
CCl3CHO + H2O → CCl3C(OH)2H

Oxidation

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Ethanol can be oxidized toacetaldehydeand further oxidized toacetic acid,depending on the reagents and conditions.[111]This oxidation is of no importance industrially, but in the human body, these oxidation reactions are catalyzed by theenzymeliver alcohol dehydrogenase.The oxidation product of ethanol, acetic acid, is a nutrient for humans, being a precursor toacetyl CoA,where the acetyl group can be spent as energy or used for biosynthesis.

Metabolism

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Ethanol is similar tomacronutrientssuch as proteins, fats, and carbohydrates in that it provides calories. When consumed and metabolized, it contributes 7 kilocalories per gram viaethanol metabolism.[132]

Safety

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See also:Alcohol (chemistry) § Toxicity

Ethanol is very flammable and should not be used around an open flame.

Pure ethanol will irritate the skin and eyes.[133]Nausea,vomiting,and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage.[134]Atmospheric concentrations above one part per thousand are above the European Unionoccupational exposure limits.[134]

History

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Further information:Liquor

The fermentation of sugar into ethanol is one of the earliestbiotechnologiesemployed by humans. Ethanol has historically been identified variously as spirit of wine or ardent spirits,[135]and asaqua vitaeor aqua vita. The intoxicating effects of its consumption have been known since ancient times. Ethanol has been used by humans since prehistory as the intoxicating ingredient ofalcoholic beverages.Dried residue on 9,000-year-old pottery found in China suggests thatNeolithicpeople consumed alcoholic beverages.[136]

The inflammable nature of the exhalations of wine was already known to ancient natural philosophers such asAristotle(384–322 BCE),Theophrastus(c. 371–287 BCE), andPliny the Elder(23/24–79 CE).[137]However, this did not immediately lead to the isolation of ethanol, even despite the development of more advanced distillation techniques in second- and third-centuryRoman Egypt.[138]An important recognition, first found in one of the writings attributed toJābir ibn Ḥayyān(ninth century CE), was that byadding saltto boiling wine, which increases the wine'srelative volatility,the flammability of the resulting vapors may be enhanced.[139]The distillation of wine is attested in Arabic works attributed toal-Kindī(c. 801–873 CE) and toal-Fārābī(c. 872–950), and in the 28th book ofal-Zahrāwī's (Latin: Abulcasis, 936–1013)Kitāb al-Taṣrīf(later translated into Latin asLiber servatoris).[140]In the twelfth century, recipes for the production ofaqua ardens( "burning water", i.e., ethanol) by distilling wine with salt started to appear in a number of Latin works, and by the end of the thirteenth century it had become a widely known substance among Western European chemists.[141]

The works ofTaddeo Alderotti(1223–1296) describe a method for concentrating ethanol involving repeatedfractional distillationthrough a water-cooledstill,by which an ethanol purity of 90% could be obtained.[142]The medicinal properties of ethanol were studied byArnald of Villanova(1240–1311 CE) andJohn of Rupescissa(c. 1310–1366), the latter of whom regarded it as a life-preserving substance able to prevent all diseases (theaqua vitaeor "water of life", also called by John thequintessenceof wine).[143]

InChina,archaeological evidence indicates that the true distillation of alcohol began during theJin(1115–1234) orSouthern Song(1127–1279) dynasties.[144]A still has been found at an archaeological site in Qinglong,Hebei,dating to the 12th century.[144]In India, the true distillation of alcohol was introduced from the Middle East, and was in wide use in theDelhi Sultanateby the 14th century.[145]

In 1796, German-Russian chemistJohann Tobias Lowitzobtained 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.[146]French chemistAntoine Lavoisierdescribed ethanol as a compound of carbon, hydrogen, and oxygen, and in 1807Nicolas-Théodore de Saussuredetermined ethanol's chemical formula.[147][148]Fifty years later,Archibald Scott Couperpublished the structural formula of ethanol. It was one of the first structural formulas determined.[149]

Ethanol was first prepared synthetically in 1825 byMichael Faraday.He found that sulfuric acid could absorb large volumes ofcoal gas.[150]He gave the resulting solution toHenry Hennell,a British chemist, who found in 1826 that it contained "sulphovinic acid" (ethyl hydrogen sulfate).[151]In 1828, Hennell and the French chemistGeorges-Simon Serullasindependently discovered that sulphovinic acid could be decomposed into ethanol.[152][153]Thus, in 1825 Faraday had unwittingly discovered that ethanol could be produced from ethylene (a component of coal gas) byacid-catalyzedhydration, a process similar to current industrial ethanol synthesis.[154]

Ethanol was used as lamp fuel in the U.S. as early as 1840, but a tax levied on industrial alcohol during theCivil Warmade this use uneconomical. The tax was repealed in 1906.[155]Use as an automotive fuel dates back to 1908, with theFord Model Table to run onpetrol(gasoline) or ethanol.[156]It fuels somespirit lamps.

Ethanol intended for industrial use is often produced from ethylene.[157]Ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. In chemistry, it is both a solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light, and more recently as a fuel for internal combustion engines.

See also

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References

edit
  1. ^Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book).Cambridge, UK: TheRoyal Society of Chemistry.2014. p. 30.doi:10.1039/9781849733069-00001.ISBN978-0-85404-182-4.
  2. ^"Ethanol".PubChem.Retrieved29 December2022.
  3. ^abcdHaynes, William M., ed. (2011).CRC Handbook of Chemistry and Physics(92nd ed.). Boca Raton, FL:CRC Press.p. 3.246.ISBN1-4398-5511-0.
  4. ^Ballinger P, Long FA (1960). "Acid Ionization Constants of Alcohols. II. Acidities of Some Substituted Methanols and Related Compounds1,2".Journal of the American Chemical Society.82(4): 795–798.doi:10.1021/ja01489a008.
  5. ^Arnett EM, Venkatasubramaniam KG (1983). "Thermochemical acidities in three superbase systems".J. Org. Chem.48(10): 1569–1578.doi:10.1021/jo00158a001.
  6. ^Lide DR, ed. (2012).CRC Handbook of Chemistry and Physics(92 ed.). Boca Raton, FL: CRC Press/Taylor and Francis. pp. 6–232.
  7. ^Lide DR, ed. (2008).CRC Handbook of Chemistry and Physics(89 ed.). Boca Raton, FL: CRC Press. pp. 9–55.
  8. ^"MSDS Ethanol".Retrieved12 January2023.
  9. ^"Ethanol".webwiser.nlm.nih.gov.Retrieved25 June2021.
  10. ^abNIOSH Pocket Guide to Chemical Hazards."#0262".National Institute for Occupational Safety and Health(NIOSH).
  11. ^"Ethyl Alcohol".Retrieved23 December2023.
  12. ^"Ethyl Alcohol".2 November 2018.Retrieved23 December2023.
  13. ^"Ethanol".PubChem. National Library of Medicine.Retrieved28 September2021.
  14. ^"Ethyl Alcohol"(PDF).Hazardous Substance Fact Sheet. New Jersey Department of Health.Retrieved28 September2021.
  15. ^Song, Frank; Walker, Matthew P. (8 November 2023)."Sleep, alcohol, and caffeine in financial traders".PLOS ONE.18(11): e0291675.Bibcode:2023PLoSO..1891675S.doi:10.1371/journal.pone.0291675.ISSN1932-6203.PMC10631622.PMID37939019.
  16. ^abPowell MA (2004)."9: Wine and the vine in ancient Mesopotamia: the cuneiform evidence".In McGovern PE, Fleming SJ, Katz SH (eds.).The Origins and Ancient History of Wine.Food and Nutrition in History and Anthropology. Vol. 11 (1 ed.). Amsterdam: Taylor & Francis. pp. 96–124.ISBN978-0-203-39283-6.ISSN0275-5769.Retrieved15 September2010.
  17. ^abSchnelle, Norbert (August 1965)."Alcohol Given Intravenously for General Anesthesia".Surgical Clinics of North America.45(4): 1041–1049.doi:10.1016/S0039-6109(16)37650-2.PMID14312998.Retrieved30 December2022.
  18. ^ab"2008 World Fuel Ethanol Production".Ellisville, Missouri: Renewable Fuels Association.Retrieved21 June2024.
  19. ^"Ethanol – Compound Summary".The PubChem Project.Bethesda, MD: National Center for Biotechnology Information.
  20. ^Liebig J (1834)."Ueber die Constitution des Aethers und seiner Verbindungen"[On the constitution of ether and its compounds].Annalen der Pharmacie(in German).9(22): 1–39.Bibcode:1834AnP...107..337L.doi:10.1002/andp.18341072202.From page 18: "Bezeichnen wir die Kohlenwasserstoffverbindung 4C + 10H als das Radikal des Aethers mit E2und nennen es Ethyl,... "(Let us designate the hydrocarbon compound 4C + 10H as the radical of ether with E2and name it ethyl...).
  21. ^Harper, Douglas."ethyl".Online Etymology Dictionary.
  22. ^For a report on the 1892 International Conference on Chemical Nomenclature, see:
  23. ^Multhauf, Robert P.(1966).The Origins of Chemistry.London: Oldbourne.ISBN9782881245947.p. 205;OED;etymonline.com
  24. ^Berthelot, Marcellin;Houdas, Octave V. (1893).La Chimie au Moyen Âge.Vol. I. Paris: Imprimerie nationale. p. 136.
  25. ^Kaveh, Anthony."3 Natural, Ancient Anesthetics No One Talks About: Opium, Alcohol, Marijuana".Dr. Anthony Kaveh, MD.Retrieved30 December2022.
  26. ^Grattan, N. "Treatment of Uterine Haemorrhage".Provincial Medicine and Surgical Journal.Vol. 1, No. 6 (Nov. 7, 1840), p. 107.
  27. ^Pohorecky, Larissa A.; Brick, John (January 1988). "Pharmacology of ethanol".Pharmacology & Therapeutics.36(2–3): 335–427.doi:10.1016/0163-7258(88)90109-X.PMID3279433.
  28. ^McDonnell G, Russell AD (January 1999)."Antiseptics and disinfectants: activity, action, and resistance".Clinical Microbiology Reviews.12(1): 147–179.doi:10.1128/CMR.12.1.147.PMC88911.PMID9880479.
  29. ^"Chemical Disinfectants | Disinfection & Sterilization Guidelines | Guidelines Library | Infection Control | CDC".www.cdc.gov.Retrieved29 January2018.
  30. ^"Why is 70% ethanol used for wiping microbiological working areas?".ResearchGate.Retrieved29 January2018.
  31. ^"Ethanol".www.drugbank.ca.Retrieved28 January2019.
  32. ^Scalley R (September 2002)."Treatment of Ethylene Glycol Poisoning".American Family Physician.66(5): 807–813.PMID12322772.Retrieved15 January2018.
  33. ^Beauchamp, GA; Valento, M (September 2016). "Toxic Alcohol Ingestion: Prompt Recognition And Management In The Emergency Department".Emergency Medicine Practice.18(9): 1–20.PMID27538060.
  34. ^Sasanami, Misa; Yamada, Taihei; Obara, Takafumi; Nakao, Atsunori; Naito, Hiromichi (2020)."Oral Ethanol Treatment for Ethylene Glycol Intoxication".Cureus.12(12): e12268.doi:10.7759/cureus.12268.ISSN2168-8184.PMC7827791.PMID33510981.
  35. ^Anseeuw, Kurt; Sabbe, Marc B.; Legrand, Annemie (April 2008)."Methanol poisoning: the duality between 'fast and cheap' and 'slow and expensive'".European Journal of Emergency Medicine.15(2): 107–109.doi:10.1097/MEJ.0b013e3282f3c13b.ISSN0969-9546.PMID18446077.S2CID23861841.
  36. ^"Alcohol Content in Common Preparations"(PDF).Medical Society of the State of New York. Archived fromthe original(PDF)on 29 April 2021.Retrieved8 October2019.
  37. ^Adams KE, Rans TS (December 2013). "Adverse reactions to alcohol and alcoholic beverages".Annals of Allergy, Asthma & Immunology.111(6): 439–445.doi:10.1016/j.anai.2013.09.016.PMID24267355.
  38. ^Zuccotti GV, Fabiano V (July 2011). "Safety issues with ethanol as an excipient in drugs intended for pediatric use".Expert Opinion on Drug Safety.10(4): 499–502.doi:10.1517/14740338.2011.565328.PMID21417862.S2CID41876817.
  39. ^Farrés J, Moreno A, Crosas B, Peralba JM, Allali-Hassani A, Hjelmqvist L, et al. (September 1994)."Alcohol dehydrogenase of class IV (sigma sigma-ADH) from human stomach. cDNA sequence and structure/function relationships".European Journal of Biochemistry.224(2): 549–557.doi:10.1111/j.1432-1033.1994.00549.x.PMID7925371.
  40. ^Edenberg HJ, McClintick JN (December 2018)."Alcohol Dehydrogenases, Aldehyde Dehydrogenases, and Alcohol Use Disorders: A Critical Review".Alcoholism: Clinical and Experimental Research.42(12): 2281–2297.doi:10.1111/acer.13904.PMC6286250.PMID30320893.
  41. ^Heit, C.; Dong, H.; Chen, Y.; Thompson, D.C.; Dietrich, R.A.; Vasiliou, V.K. (2013). "The Role of CYP2E1 in Alcohol Metabolism and Sensitivity in the Central Nervous System".Cytochrome P450 2E1: Its Role in Disease and Drug Metabolism.Subcellular Biochemistry. Vol. 67. pp. 235–237.doi:10.1007/978-94-007-5881-0_8.ISBN978-94-007-5880-3.PMC4314297.PMID23400924.
  42. ^"Alcohol Metabolism: An Update".NIAA Publications.National Institute of Health. Archived fromthe originalon 28 February 2021.Retrieved10 March2021.
  43. ^abEng MY, Luczak SE, Wall TL (2007)."ALDH2, ADH1B, and ADH1C genotypes in Asians: a literature review".Alcohol Research & Health.30(1): 22–27.PMC3860439.PMID17718397.
  44. ^"Alcohol use and safe drinking: MedlinePlus Medical Encyclopedia".medlineplus.gov.Retrieved11 March2023.
  45. ^abEyidogan M, Ozsezen AN, Canakci M, Turkcan A (2010). "Impact of alcohol–gasoline fuel blends on the performance and combustion characteristics of an SI engine".Fuel.89(10): 2713–2720.Bibcode:2010Fuel...89.2713E.doi:10.1016/j.fuel.2010.01.032.
  46. ^abThomas, George (2000)."Overview of Storage Development DOE Hydrogen Program"(PDF).Livermore, California: Sandia National Laboratories. Archived fromthe original(PDF)on 21 February 2007.
  47. ^Thomas G (2000)."Overview of Storage Development DOE Hydrogen Program"(PDF).Sandia National Laboratories.Retrieved1 August2009.
  48. ^"Availability of Sources of E85".Clean Air Trust.Retrieved27 July2015.
  49. ^"Fuel ethanol production worldwide".Statista.Retrieved2 June2021.
  50. ^ab"First Commercial U.S. Cellulosic Ethanol Biorefinery Announced".Renewable Fuels Association. 20 November 2006.Retrieved31 May2011.
  51. ^Green R."Model T Ford Club Australia (Inc.)".Archived fromthe originalon 14 January 2014.Retrieved24 June2011.
  52. ^"Ethanol 101".American Coalition for Ethanol. Archived fromthe originalon 14 November 2020.Retrieved26 March2011.
  53. ^Energy Future Coalition."The Biofuels FAQs".The Biofuels Source Book.United Nations Foundation.Archived fromthe originalon 19 February 2011.
  54. ^Malaquias, Augusto César Teixeira; Netto, Nilton Antonio Diniz; Filho, Fernando Antonio Rodrigues; da Costa, Roberto Berlini Rodrigues; Langeani, Marcos; Baêta, José Guilherme Coelho (18 November 2019)."The misleading total replacement of internal combustion engines by electric motors and a study of the Brazilian ethanol importance for the sustainable future of mobility: a review".Journal of the Brazilian Society of Mechanical Sciences and Engineering.41(12): 567.doi:10.1007/s40430-019-2076-1.ISSN1806-3691.
  55. ^California Air Resources Board (October 1989)."Definition of a Low Emission Motor Vehicle in Compliance with the Mandates of Health and Safety Code Section 39037.05, second release".Archived fromthe originalon 18 February 2018.Retrieved18 February2018.
  56. ^Lowi A, Carter WP (March 1990).A Method for Evaluating the Atmospheric Ozone Impact of Actual Vehicle emissions.Warrendale, Pennsylvania.{{cite book}}:|work=ignored (help)CS1 maint: location missing publisher (link)
  57. ^Jones TT (2008)."The Clean Fuels Report: A Quantitative Comparison Of Motor (engine) Fuels, Related Pollution and Technologies".researchandmarkets.com.Archived fromthe originalon 9 September 2012.
  58. ^Tao R (16–20 August 2010).Electro-rheological Fluids and Magneto-rheological Suspensions.Philadelphia: World Scientific.ISBN9789814340229.{{cite book}}:|work=ignored (help)
  59. ^Biello D."Want to Reduce Air Pollution? Don't Rely on Ethanol Necessarily".Scientific American.Retrieved11 July2017.
  60. ^"Adoption of the Airborne Toxic Control Measure to Reduce Formaldehyde Emissions from Composite Wood Products".Chicago & Washington, DC: Window and Door Manufacturers Association. 30 July 2008. Archived fromthe originalon 9 March 2010.
  61. ^"Tecnologia flex atrai estrangeiros"(in Brazilian Portuguese). Agência Estado.
  62. ^Horn M, Krupp F (16 March 2009).Earth: The Sequel: The Race to Reinvent Energy and Stop Global Warming.Vol. 62. pp. 63–65.Bibcode:2009PhT....62d..63K.doi:10.1063/1.3120901.ISBN978-0-393-06810-8.S2CID153892198.{{cite book}}:|journal=ignored (help)
  63. ^"Mechanics see ethanol damaging small engines"Archived23 September 2020 at theWayback Machine,NBC News,8 January 2008
  64. ^Clark, John D. (2017).Ingnition! An Informal History of Liquid Rocket Propellants.New Brunswick, New Jersey: Rutgers University Press. p. 9.ISBN978-0-8135-9583-2.
  65. ^Darling D."The Internet Encyclopedia of Science: V-2".
  66. ^ab"Basics of Space Flight: Rocket Propellants".braeunig.us.Retrieved11 March2023.
  67. ^"A Brief History of Rocketry".Archived5 August 2006 at theWayback MachineNASA Historical Archive.
  68. ^Chow D (26 April 2010)."Rocket Racing League Unveils New Flying Hot Rod".Space.com.Retrieved27 April2010.
  69. ^Badwal SP, Giddey S, Kulkarni A, Goel J, Basu S (May 2015)."Direct ethanol fuel cells for transport and stationary applications – A comprehensive review".Applied Energy.145:80–103.Bibcode:2015ApEn..145...80B.doi:10.1016/j.apenergy.2015.02.002.
  70. ^Immergut, Debra Jo (3 December 2015)."Can Ethanol Fireplaces Be Cozy?".The Wall Street Journal.Retrieved2 March2016.
  71. ^Rajvanshi AK, Patil SM, Mendonca B (March 2007)."Low-concentration ethanol stove for rural areas in India".Energy for Sustainable Development.11(1): 94–99.Bibcode:2007ESusD..11...94R.CiteSeerX10.1.1.142.5846.doi:10.1016/S0973-0826(08)60568-2.
  72. ^"Your Guide to Ethanol Extraction".Cannabis Business Times.Retrieved9 April2019.
  73. ^"Flame Temperature Analysis and NOx Emissions for Different Fuels".Mississippi State Department of Chemical Engineering.
  74. ^abcLide DR, ed. (2000).CRC Handbook of Chemistry and Physics 81st edition.CRC press.ISBN978-0-8493-0481-1.
  75. ^"Ethanol".NIST Chemistry WebBook, SRD 69.2023.Retrieved23 December2023.
  76. ^abcdWindholz M (1976).The Merck index: an encyclopedia of chemicals and drugs(9th ed.). Rahway, NJ: Merck.ISBN978-0-911910-26-1.[page needed]
  77. ^abcMorrison RT, Boyd RN (1972).Organic Chemistry(2nd ed.). Allyn and Bacon, inc.ISBN978-0-205-08452-4.[page needed]
  78. ^Dahlmann U, Schneider GM (1989). "(Liquid + liquid) phase equilibria and critical curves of (ethanol + dodecane or tetradecane or hexadecane or 2,2,4,4,6,8,8-heptamethylnonane) from 0.1 MPa to 120.0 MPa".J Chem Thermodyn.21(9): 997–1004.Bibcode:1989JChTh..21..997D.doi:10.1016/0021-9614(89)90160-2.
  79. ^"Ethanol".Encyclopedia of chemical technology.Vol. 9. 1991. p. 813.
  80. ^Costigan MJ, Hodges LJ, Marsh KN, Stokes RH, Tuxford CW (1980). "The Isothermal Displacement Calorimeter: Design Modifications for Measuring Exothermic Enthalpies of Mixing".Aust. J. Chem.33(10): 2103.Bibcode:1982AuJCh..35.1971I.doi:10.1071/CH9802103.
  81. ^Lei Z, Wang H, Zhou R, Duan Z (2002). "Influence of salt added to solvent on extractive distillation".Chem. Eng. J.87(2): 149–156.Bibcode:2002ChEnJ..87..149L.doi:10.1016/S1385-8947(01)00211-X.
  82. ^Pemberton RC, Mash CJ (1978). "Thermodynamic properties of aqueous non-electrolyte mixtures II. Vapour pressures and excess Gibbs energies for water + ethanol at 303.15 to 363.15 K determined by an accurate static method".J Chem Thermodyn.10(9): 867–888.Bibcode:1978JChTh..10..867P.doi:10.1016/0021-9614(78)90160-X.
  83. ^Merck Index of Chemicals and Drugs,9th ed.; monographs 6575 through 6669
  84. ^"Flash Point and Fire Point".Nttworldwide.com.Archived fromthe originalon 14 December 2010.
  85. ^abNFPA 325: Guide to Fire Hazard Properties of Flammable Liquids, Gases, and Volatile Solids.Quincy, Massachusetts: National Fire Protection Association (NFPA). 1 January 1994.
  86. ^ab"49 CFR § 173.120 – Class 3 – Definitions".Legal Information Institute.a flammable liquid (Class 3) means a liquid having a flash point of not more than 60 °C (140 °F)
  87. ^abcdefghijkMartínez, P. J.; Rus, E.; Compaña, J. M."Flash Point Determination of Binary Mixtures of Alcohols, Ketones and Water".Departamento de Ingeniería Química, Facultad de Ciencias.p. 3, Table 4.
  88. ^"49 CFR § 172.101 – Purpose and use of hazardous materials table".Legal Information Institute, Cornell University.Hazardous materials descriptions and proper shipping names: Ethanol or Ethyl alcohol or Ethanol solutions or Ethyl alcohol solutions; Hazard class or Division: 3; Identification Numbers: UN1170; PG: II; Label Codes: 3;
  89. ^abcdefghHa, Dong-Myeong; Park, Sang Hun; Lee, Sungjin (April 2015)."The Measurement of Flash Point of Water-Methanol and Water-Ethanol Systems Using Seta Flash Closed Cup Tester".Fire Science and Engineering.29(2): 39–43.doi:10.7731/KIFSE.2015.29.2.039.Page 4, Table 3
  90. ^"Flash points of ethanol-based water solutions".Engineeringtoolbox.com.Retrieved23 June2011.
  91. ^Dudley R (August 2004)."Ethanol, fruit ripening, and the historical origins of human alcoholism in primate frugivory".Integrative and Comparative Biology.44(4): 315–323.doi:10.1093/icb/44.4.315.PMID21676715.
  92. ^Graber C (2008)."Fact or Fiction?: Animals Like to Get Drunk".Scientific American.Retrieved23 July2010.
  93. ^Leblová S, Sinecká E, Vaníčková V (1974). "Pyruvate metabolism in germinating seeds during natural anaerobiosis".Biologia Plantarum.16(6): 406–411.doi:10.1007/BF02922229.S2CID34605254.
  94. ^Schriver A, Schriver-Mazzuoli L, Ehrenfreund P, d'Hendecourt L (2007). "One possible origin of ethanol in interstellar medium: Photochemistry of mixed CO2–C2H6films at 11 K. A FTIR study ".Chemical Physics.334(1–3): 128–137.Bibcode:2007CP....334..128S.doi:10.1016/j.chemphys.2007.02.018.
  95. ^Turner C, Spanel P, Smith D (2006). "A longitudinal study of ethanol and acetaldehyde in the exhaled breath of healthy volunteers using selected-ion flow-tube mass spectrometry".Rapid Communications in Mass Spectrometry.20(1): 61–68.Bibcode:2006RCMS...20...61T.doi:10.1002/rcm.2275.PMID16312013.
  96. ^Doucleff M (17 September 2013)."Auto-Brewery Syndrome: Apparently, You Can Make Beer In Your Gut".NPR.
  97. ^Mills GA, Ecklund EE (1987)."Alcohols as Components of Transportation Fuels".Annual Review of Energy.12:47–80.doi:10.1146/annurev.eg.12.110187.000403.
  98. ^Reel M (19 August 2006)."Brazil's Road to Energy Independence".The Washington Post.
  99. ^Rossi, Liane M.; Gallo, Jean Marcel R.; Mattoso, Luiz H. C.; Buckeridge, Marcos S.; Licence, Peter; Allen, David T. (29 March 2021)."Ethanol from Sugarcane and the Brazilian Biomass-Based Energy and Chemicals Sector".ACS Sustainable Chemistry & Engineering.9(12): 4293–4295.doi:10.1021/acssuschemeng.1c01678.ISSN2168-0485.S2CID233676614.
  100. ^Wittcoff HA, Reuben BG, Plotkin JS (2004).Industrial Organic Chemicals.John Wiley & Sons. pp. 136–.ISBN978-0-471-44385-8.
  101. ^Swami, V. N. (2020).विद्याभराती जिल्हा मध्यवर्ती सहकारी बँक भारती परीक्षा मार्गदर्शक[Vidyabharti District Co-operative Bank recruitment examination guide (Bank clerk grade examination)] (in Marathi).Latur,Maharashtra, India: Vidyabharti Publication. p. 119.
  102. ^"Sweet sorghum for food, feed and fuel"(PDF).New Agriculturalist.January 2008. Archived fromthe original(PDF)on 4 September 2015.Retrieved11 March2023.
  103. ^"Developing a sweet sorghum ethanol value chain"Archived23 February 2014 at theWayback Machine.ICRISAT,2013
  104. ^Roberts JD,Caserio MC(1977).Basic Principles of Organic Chemistry.W. A. Benjamin.ISBN978-0-8053-8329-4.[page needed]
  105. ^abcdKosaric N, Duvnjak Z, Farkas A, Sahm H, Bringer-Meyer S, Goebel O, Mayer D (2011). "Ethanol".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH. pp. 1–72.doi:10.1002/14356007.a09_587.pub2.ISBN978-3-527-30673-2.(subscription required)
  106. ^"Ethanol".Encyclopedia of chemical technology.Vol. 9. 1991. p. 82.
  107. ^"Ethanol"Archived13 January 2015 at theWayback Machine.Essential Chemical Industry.
  108. ^Harrison, Tim (May 2014)."Catalysis Web Pages for Pre-University Students V1_0"(PDF).Bristol ChemLabs, School of Chemistry.University of Bristol. Archived fromthe original(PDF)on 5 March 2021.
  109. ^Tullo, Alexander (26 August 2021)."Last synthetic ethanol plant in US to close".cen.acs.org.Retrieved22 November2022.
  110. ^Lodgsdon JE (1991). "Ethanol". In Howe-Grant M, Kirk RE, Othmer DF, Kroschwitz JI (eds.).Encyclopedia of chemical technology.Vol. 9 (4th ed.). New York: Wiley. p. 817.ISBN978-0-471-52669-8.
  111. ^abcdeStreitwieser A,Heathcock CH(1976).Introduction to Organic Chemistry.MacMillan.ISBN978-0-02-418010-0.
  112. ^Liew F, Henstra AM, Köpke M, Winzer K, Simpson SD, Minton NP (March 2017)."Metabolic engineering of Clostridium autoethanogenum for selective alcohol production".Metabolic Engineering.40:104–114.doi:10.1016/j.ymben.2017.01.007.PMC5367853.PMID28111249.
  113. ^"Solar-to-Fuel System Recycles CO2 for Ethanol and Ethylene".News Center.18 September 2017.Retrieved19 September2017.
  114. ^Clines T (July 2006)."Brew Better Ethanol".Popular Science Online. Archived fromthe originalon 3 November 2007.
  115. ^Chemists, American Association of Cereal (1986).Advances in Cereal Science and Technology.American Association of Cereal Chemists, Incorporated.ISBN978-0-913250-45-7.
  116. ^Dale Callaham,Molecular Sieve Information
  117. ^Song Y, Peng R, Hensley DK, Bonnesen PV, Liang L, Wu Z, Meyer HM, Chi M, Ma C, Sumpter BG, Rondinone AJ (2016)."High-Selectivity Electrochemical Conversion of CO2 to Ethanol using a Copper Nanoparticle/N-Doped Graphene Electrode".ChemistrySelect.1(Preprint): 6055–6061.doi:10.1002/slct.201601169.
  118. ^Jeong JS, Jeon H, Ko Km, Chung B, Choi GW (2012). "Production of anhydrous ethanol using various PSA (Pressure Swing Adsorption) processes in pilot plant".Renewable Energy.42:41–45.Bibcode:2012REne...42...41J.doi:10.1016/j.renene.2011.09.027.
  119. ^"U-M Program to Reduce the Consumption of Tax-free Alcohol; Denatured Alcohol a Safer, Less Expensive Alternative"(PDF).University of Michigan. Archived fromthe original(PDF)on 27 November 2007.Retrieved29 September2007.
  120. ^Great Britain (2005).The Denatured Alcohol Regulations 2005Archived9 December 2009 at theWayback Machine.Statutory Instrument 2005 No. 1524.
  121. ^Bansal RK, Bernthsen A (2003).A Textbook of Organic Chemistry.New Age International Limited. pp. 402–.ISBN978-81-224-1459-2.
  122. ^Christian GD (2004)."Solvents for Spectrometry".Analytical chemistry.Vol. 1 (6th ed.). Hoboken, NJ: John Wiley & Sons. p.473.ISBN978-0-471-21472-4.
  123. ^Andrews S (1 August 2007).Textbook Of Food & Bevrge Mgmt.Tata McGraw-Hill Education. pp. 268–.ISBN978-0-07-065573-7.
  124. ^Kunkee RE, Amerine MA (July 1968)."Sugar and alcohol stabilization of yeast in sweet wine".Applied Microbiology.16(7): 1067–1075.doi:10.1128/AEM.16.7.1067-1075.1968.PMC547590.PMID5664123.
  125. ^Zimmermann, Heinz; Walz, Roland (2008). "Ethylene".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a10_045.pub3.ISBN978-3-527-30673-2.
  126. ^"14.4: Dehydration Reactions of Alcohols".Chemistry LibreTexts.9 February 2016.Retrieved9 May2022.
  127. ^"Alkenes from Dehydration of Alcohols".Chemistry LibreTexts.2 October 2013.Retrieved9 May2022.
  128. ^Rossini FD (1937). "Heats of Formation of Simple Organic Molecules".Ind. Eng. Chem.29(12): 1424–1430.doi:10.1021/ie50336a024.
  129. ^Calculated from heats of formation from CRC Handbook of Chemistry and Physics, 49th Edition, 1968–1969.
  130. ^Chakrabartty SK (1978). Trahanovsky WS (ed.).Oxidation in Organic Chemistry.New York: Academic Press. pp. 343–370.
  131. ^Reinhard J, Kopp E, McKusick BC, Röderer G, Bosch A, Fleischmann G (2007). "Chloroacetaldehydes".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a06_527.pub2.ISBN978-3-527-30673-2.
  132. ^Cederbaum, Arthur I (16 November 2012)."Alcohol Metabolism".Clinics in Liver Disease.16(4): 667–685.doi:10.1016/j.cld.2012.08.002.ISSN1089-3261.PMC3484320.PMID23101976.
  133. ^Minutes of MeetingArchived16 April 2021 at theWayback Machine.Technical Committee on Classification and Properties of Hazardous Chemical Data (12–13 January 2010).
  134. ^ab"Safety data for ethyl alcohol".University of Oxford. 9 May 2008. Archived fromthe originalon 14 July 2011.Retrieved3 January2011.
  135. ^Ottley, William Campbell (1826).A dictionary of chemistry and of mineralogy as connected with it.Murray.
  136. ^Roach J (18 July 2005)."9,000-Year-Old Beer Re-Created From Chinese Recipe".National Geographic News.Archived fromthe originalon 22 July 2005.Retrieved3 September2007.
  137. ^Berthelot & Houdas 1893,vol. I, p. 137.
  138. ^Berthelot & Houdas 1893,vol. I, pp. 138-139.
  139. ^al-Hassan, Ahmad Y.(2009). "Alcohol and the Distillation of Wine in Arabic Sources from the 8th Century".Studies in al-Kimya': Critical Issues in Latin and Arabic Alchemy and Chemistry.Hildesheim: Georg Olms Verlag. pp. 283–298.(same content also available onthe author's websiteArchived29 December 2015 at theWayback Machine).
  140. ^al-Hassan 2009(same content also available onthe author's websiteArchived29 December 2015 at theWayback Machine); cf.Berthelot & Houdas 1893,vol. I, pp. 141, 143. Sometimes, sulfur was also added to the wine (seeBerthelot & Houdas 1893,vol. I, p. 143).
  141. ^Multhauf 1966,pp. 204–206.
  142. ^Holmyard, Eric John(1957).Alchemy.Harmondsworth: Penguin Books.ISBN978-0-486-26298-7.pp. 51–52.
  143. ^Principe, Lawrence M.(2013).The Secrets of Alchemy.Chicago: The University of Chicago Press.ISBN978-0-226-10379-2.pp. 69-71.
  144. ^abHaw SG(2006)."Wine, women and poison".Marco Polo in China.Routledge. pp. 147–148.ISBN978-1-134-27542-7.Retrieved10 July2016.The earliest possible period seems to be the Eastern Han dynasty... the most likely period for the beginning of true distillation of spirits for drinking in China is during the Jin and Southern Song dynasties
  145. ^Habib, Irfan(2011).Economic History of Medieval India, 1200–1500.Pearson Education India. pp. 55–.ISBN978-81-317-2791-1.
  146. ^Lowitz T (1796)."Anzeige eines, zur volkommen Entwasserung des Weingeistes nothwendig zu beobachtenden, Handgriffs"[Report of a task that must be done for the complete dehydration of wine spirits [i.e., alcohol-water azeotrope])].Chemische Annalen für die Freunde der Naturlehre, Aerznengelartheit, Haushaltungskunde und Manufakturen(in German).1:195–204.See pp. 197–198: Lowitz dehydrated the azeotrope by mixing it with a 2:1 excess of anhydrous alkali and then distilling the mixture over low heat.
  147. ^Chisholm, Hugh,ed. (1911)."Alcohol".Encyclopædia Britannica.Vol. 1 (11th ed.). Cambridge University Press. pp. 525–527.
  148. ^de Saussure T (1807)."Mémoire sur la composition de l'alcohol et de l'éther sulfurique".Journal de Physique, de Chimie, d'Histoire Naturelle et des Arts.64:316–354.In his 1807 paper, Saussure determined ethanol's composition only roughly; a more accurate analysis of ethanol appears on page 300 of his 1814 paper:de Saussure, Théodore (1814)."Nouvelles observations sur la composition de l'alcool et de l'éther sulfurique".Annales de Chimie et de Physique.89:273–305.
  149. ^Couper AS (1858)."On a new chemical theory"(online reprint).Philosophical Magazine.16(104–116).Retrieved3 September2007.
  150. ^Faraday M (1825)."On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat".Philosophical Transactions of the Royal Society of London.115:440–466.doi:10.1098/rstl.1825.0022.In a footnote on page 448, Faraday notes the action of sulfuric acid on coal gas and coal-gas distillate; specifically, "The [sulfuric] acid combines directly with carbon and hydrogen; and I find when [the resulting compound is] united with bases [it] forms a peculiar class of salts, somewhat resembling the sulphovinates [i.e., ethyl sulfates], but still different from them."
  151. ^Hennell H (1826)."On the mutual action of sulphuric acid and alcohol, with observations on the composition and properties of the resulting compound".Philosophical Transactions of the Royal Society of London.116:240–249.doi:10.1098/rstl.1826.0021.S2CID98278290.On page 248, Hennell mentions that Faraday gave him some sulfuric acid in which coal gas had dissolved and that he (Hennell) found that it contained "sulphovinic acid" (ethyl hydrogen sulfate).
  152. ^Hennell H (1828)."On the mutual action of sulfuric acid and alcohol, and on the nature of the process by which ether is formed".Philosophical Transactions of the Royal Society of London.118:365–371.doi:10.1098/rstl.1828.0021.S2CID98483646.On page 368, Hennell produces ethanol from "sulfovinic acid" (ethyl hydrogen sulfate).
  153. ^Sérullas GS (1828). Guyton de Morveau LB, Gay-Lussac JL, Arago F, Michel Eugène Chevreul, Marcellin Berthelot, Éleuthère Élie Nicolas Mascart, Albin Haller (eds.)."De l'action de l'acide sulfurique sur l'alcool, et des produits qui en résultent".Annales de Chimie et de Physique.39:152–186.On page 158, Sérullas mentions the production of alcohol from "sulfate acid d'hydrogène carboné" (hydrocarbon acid sulfate).
  154. ^In 1855, the French chemistMarcellin Berthelotconfirmed Faraday's discovery by preparing ethanol from pure ethylene.Berthelot M (1855). Arago F, Gay-Lussac JL (eds.)."Sur la formation de l'alcool au moyen du bicarbure d'hydrogène (On the formation of alcohol by means of ethylene)".Annales de Chimie et de Physique.43:385–405.(Note: The chemical formulas in Berthelot's paper are wrong because chemists at that time used the wrong atomic masses for the elements; e.g., carbon (6 instead of 12), oxygen (8 instead of 16), etc.)
  155. ^Siegel R (15 February 2007)."Ethanol, Once Bypassed, Now Surging Ahead".NPR.Retrieved22 September2007.
  156. ^DiPardo J."Outlook for Biomass Ethanol Production and Demand"(PDF).United States Department of Energy. Archived fromthe original(PDF)on 24 September 2015.Retrieved22 September2007.
  157. ^Myers RL, Myers RL (2007).The 100 most important chemical compounds: a reference guide.Westport, CN: Greenwood Press. p. 122.ISBN978-0-313-33758-1.

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