Ethanol
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Names | |||
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Pronunciation | /ˈɛθənɒl/ | ||
Preferred IUPAC name
Ethanol[1] | |||
Other names
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Identifiers | |||
3D model (
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3DMet | |||
1718733 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard
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100.000.526 | ||
787 | |||
IUPHAR/BPS |
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KEGG | |||
PubChem CID
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UNII | |||
UN number | UN 1170 | ||
CompTox Dashboard (EPA)
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Properties | |||
C2H6O | |||
Molar mass | 46.069 g·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 | |||
log P | −0.18 | ||
Vapor pressure | 5.95 kPa (at 20 °C) | ||
Acidity (pKa) | 15.9 (H2O), 29.8 (DMSO)[4][5] | ||
−33.60·10−6 cm3/mol | |||
Refractive index (nD)
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1.3611[3] | ||
Viscosity | 1.2 mPa·s (at 20 °C), 1.074 mPa·s (at 25 °C)[6] | ||
1.69 D[7] | |||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H319, H360D | |||
P210, P233, P240, P241, P242, P305+P351+P338 | |||
NFPA 704 (fire diamond) | |||
Flash point | 14 °C (Absolute)[9] | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 1000 ppm (1900 mg/m3)[10] | ||
REL (Recommended)
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TWA 1000 ppm (1900 mg/m3)[10] | ||
IDLH (Immediate danger) |
3300 ppm [11] | ||
Safety data sheet (SDS) | [8] | ||
Related compounds | |||
Related compounds
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Supplementary data page | |||
Ethanol (data page) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an
Ethanol is naturally produced by the
Etymology
Ethanol is the systematic name defined by the International Union of Pure and Applied Chemistry for a compound consisting of an alkyl group with two carbon atoms (prefix "eth-"), having a single bond between them (infix "-an-") and an attached −OH functional group (suffix "-ol").[18]
The "eth-" prefix and the qualifier "ethyl" in "ethyl alcohol" originally came from the name "ethyl" assigned in 1834 to the group C
2H
5− by Justus Liebig. He coined the word from the German name Aether of the compound C
2H
5−O−C
2H
5 (commonly called "ether" in English, more specifically called "diethyl ether").[19] According to the Oxford English Dictionary, Ethyl is a contraction of the Ancient Greek αἰθήρ (aithḗr, "upper air") and the Greek word ὕλη (hýlē, "wood, raw material", hence "matter, substance").[20]
The name ethanol was coined as a result of a resolution on naming alcohols and phenols that was adopted at the International Conference on Chemical Nomenclature that was held in April 1892 in Geneva, Switzerland.[21]
The term alcohol now 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 from
Uses
Medical
Anesthetic
Ethanol is the oldest known
Antiseptic
Ethanol is used in medical wipes and most commonly in antibacterial
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.[28][29] 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.[30]
Antidote
Ethanol may be administered as an
Medicinal solvent
Ethanol, often in high concentrations, is used to dissolve many water-insoluble medications and related compounds. Liquid preparations of
Pharmacology
In mammals, ethanol is primarily
- CH3CH2OH + NAD+ → CH3CHO + NADH+ H+
When present in significant concentrations, this metabolism of ethanol is additionally aided by the cytochrome P450 enzyme CYP2E1 in humans, while trace amounts are also metabolized by catalase.[40]
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.[41]
The subsequent oxidation of acetaldehyde into acetate is performed by aldehyde 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 characteristic alcohol flush reaction that can cause temporary reddening of the skin as well as a number of related, and often unpleasant, symptoms of acetaldehyde toxicity.[42] This mutation is typically accompanied by another mutation in the alcohol dehydrogenase enzyme ADH1B in roughly 80 % of east Asians, which improves the catalytic efficiency of converting ethanol into acetaldehyde.[42]
Recreational
As a central nervous system depressant, ethanol is one of the most commonly consumed psychoactive drugs.[43]
Despite alcohol's psychoactive, addictive, and carcinogenic properties, 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
Engine fuel
Fuel type | MJ/L | MJ/kg | Research octane number |
---|---|---|---|
Dry wood (20% moisture) | ~19.5 | ||
Methanol | 17.9 | 19.9 | 108.7[44] |
Ethanol | 21.2[45] | 26.8[45] | 108.6[44] |
E85 (85% ethanol, 15% gasoline) |
25.2 | 33.2 | 105 |
Liquefied natural gas | 25.3 | ~55 | |
) | 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[46] | 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 engine
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.[49]
Australian law limits the use of pure ethanol from sugarcane waste to 10 % in automobiles. Older cars (and vintage cars designed to use a slower burning fuel) should have the engine valves upgraded or replaced.[50]
According to an industry
Ethanol
More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanol-only engines and
Ethanol's high
Rocket fuel
Ethanol was commonly used as fuel in early
Fuel cells
Commercial fuel cells operate on reformed natural gas, hydrogen or 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 including direct-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.[68]
Household heating and cooking
Ethanol fireplaces can be used for home heating or for decoration. Ethanol can also be used as stove fuel for cooking.[69][70]
Feedstock
Ethanol is an important industrial ingredient. It has widespread use as a precursor for other organic compounds such as ethyl halides, ethyl esters, diethyl ether, acetic acid, and ethyl amines.
Solvent
Ethanol is considered a universal
Ethanol is found in
Low-temperature liquid
Because of its low
Chemistry
Chemical formula
Ethanol is a 2-carbon
Physical properties
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 as propane.
Ethanol's adiabatic flame temperature for combustion in air is 2082 °C or 3779 °F.[72]
Ethanol is slightly more refractive than water, having a refractive index of 1.36242 (at λ=589.3 nm and 18.35 °C or 65.03 °F).[73] The triple point for ethanol is 150 ± 20 K.[74]
Solvent properties
Ethanol is a versatile solvent,
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.[76] The miscibility of ethanol with alkanes is limited to alkanes up to undecane: mixtures with dodecane and higher alkanes show a miscibility gap below a certain temperature (about 13 °C for dodecane[77]). 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.
Mixtures of ethanol and water form an azeotrope at about 89 mole-% ethanol and 11 mole-% water[80] 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.[81]
Hydrogen bonding causes pure ethanol to be
The addition of even a few percent of ethanol to water sharply reduces the surface tension of 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
An ethanol–water solution will catch fire if heated above a temperature called its flash point and an ignition source is then applied to it.[83] 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),[84] 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; 6 proof).[85][86][87]
Ethanol mole fraction, % |
Temperature | |
---|---|---|
°C | °F | |
1 | 84.5 | 184.1[86] |
2 | 64 | 147[86] |
2.35 | 60 | 140[86][85] |
3 | 51.5 | 124.7[86] |
5 | 43 | 109[88] |
6 | 39.5 | 103.1[86] |
10 | 31 | 88[88] |
20 | 25 | 77[86] |
30 | 24 | 75[88] |
40 | 21.9 | 71.4[citation needed][88] |
50 | 20 | 68[88][86] |
60 | 17.9 | 64.2[citation needed][88] |
70 | 16 | 61[88] |
80 | 15.8 | 60.4[86] |
90 | 14 | 57[88] |
100 | 12.5 | 54.5[88][86][84] |
Dishes using burning alcohol for culinary effects are called flambé.
Natural occurrence
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.
Production
Ethanol is produced both as a petrochemical, through the hydration of ethylene and, via biological processes, by fermenting sugars with yeast.[96] Which process is more economical depends on prevailing prices of petroleum and grain feed stocks.
Sources
World production of ethanol in 2006 was 51 gigalitres (1.3×1010 US gal), with 69% of the world supply coming from Brazil and the U.S.[17] 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 other energy crops.[97] Sugarcane not only has a greater concentration of sucrose than corn (by about 30%), but is also much easier to extract. The bagasse generated 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.[98]
In the 1970s most industrial ethanol in the U.S. was made as a petrochemical, but in the 1980s the U.S. introduced subsidies for
In India ethanol is made from sugarcane.[100] Sweet sorghum is another potential source of ethanol, and is suitable for growing in dryland conditions. The International Crops Research Institute for the Semi-Arid Tropics is investigating the possibility of growing sorghum as a source of fuel, food, and animal feed in arid parts of Asia and Africa.[101] 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 in Andhra Pradesh, India.[102]
Hydration
Ethanol can be produced from petrochemical feed stocks, primarily by the acid-catalyzed hydration of ethylene. It is often referred to as synthetic ethanol.
- C2H4 + H2O → C2H5OH
The catalyst is most commonly
In an older process, first practiced on the industrial scale in 1930 by Union Carbide
- C2H4 + H2SO4 → C2H5HSO4
- C2H5HSO4 + H2O → H2SO4 + C2H5OH
From carbon dioxide
Ethanol has been produced in the laboratory by converting
2O → CH
3CH
2OH + side products
Fermentation
Ethanol in alcoholic beverages and fuel is produced by fermentation. Certain species of yeast (e.g., Saccharomyces cerevisiae) metabolize sugar (namely polysaccharides), producing ethanol and carbon dioxide. The chemical equations below summarize the conversion:
6H
12O
6 → 2 CH
3CH
2OH + 2 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 by fortification or distillation. The most ethanol-tolerant yeast strains can survive up to approximately 18% ethanol by volume.
To produce ethanol from starchy materials such as cereals, the starch must first be converted into sugars. In brewing beer, this has traditionally been accomplished by allowing the grain to germinate, or malt, which produces the enzyme amylase. When the malted grain is mashed, the amylase converts the remaining starches into sugars.
Cellulose
Sugars for
Testing
Breweries and biofuel plants 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 the Beer–Lambert law. Alternatively, by measuring the density of the starting material and the density of the product, using a hydrometer, 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
Distillation
Ethylene hydration or brewing produces an ethanol–water mixture. For most industrial and fuel uses, the ethanol must be purified. Fractional distillation at atmospheric pressure can concentrate ethanol to 95.6% by weight (89.5 mole%). This mixture is an azeotrope with a boiling point of 78.1 °C (172.6 °F), and cannot be further purified by distillation. Addition of an entraining agent, such as benzene, cyclohexane, or heptane, 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.[104]
Molecular sieves and desiccants
Apart from distillation, ethanol may be dried by addition of a
Membranes and reverse osmosis
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
A variety of other techniques have been discussed, including the following:[104]
- Salting using potassium carbonate to exploit its insolubility will cause a phase separation with ethanol and water. This offers a very small potassium carbonate impurity to the alcohol that can be removed by distillation. This method is very useful in purification of ethanol by distillation, as ethanol forms an azeotrope with water.
- Direct electrochemical reduction of carbon dioxide to ethanol under ambient conditions using copper nanoparticles on a carbon nanospike film as the catalyst;[116]
- Extraction of ethanol from grain mash by supercritical carbon dioxide;
- Pervaporation;
- Applejack (beverage);
- Pressure swing adsorption.[117]
Grades of ethanol
Denatured alcohol
Pure ethanol and alcoholic beverages are heavily
Absolute alcohol
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). If
Pure ethanol is classed as 200
Rectified spirits
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.[123]
Reactions
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
In the presence of acid catalysts, ethanol reacts with carboxylic acids to produce ethyl esters and 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 as saponification because it is used in the preparation of soap. Ethanol can also form esters with inorganic acids. Diethyl sulfate and triethyl phosphate are prepared by treating ethanol with sulfur trioxide and phosphorus pentoxide respectively. Diethyl sulfate is a useful ethylating agent in organic synthesis. Ethyl nitrite, prepared from the reaction of ethanol with sodium nitrite and sulfuric acid, was formerly used as a diuretic.
Dehydration
In the presence of acid catalysts, alcohols can be converted to alkenes such as ethanol to ethylene. Typically
- CH3CH2OH → H2C=CH2 + H2O
Since water is removed from the same molecule, the reaction is known as
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 dehydration may occur producing a symmetrical ether. This is a condensation reaction. In the following example, diethyl ether is produced from ethanol:
- 2 CH3CH2OH → CH3CH2OCH2CH3 + H2O[126]
Combustion
Complete combustion of ethanol forms carbon dioxide and water:
- C2H5OH (l) + 3 O2 (g) → 2 CO2 (g) + 3 H2O (l); −ΔcH = 1371 kJ/mol[127] = 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[128]
Specific heat = 2.44 kJ/(kg·K)
Acid-base chemistry
Ethanol is a neutral molecule and the
- 2 CH3CH2OH + 2 Na → 2 CH3CH2ONa + H2
or a very strong base such as sodium hydride:
- CH3CH2OH + NaH → CH3CH2ONa + H2
The acidities of water and ethanol are nearly the same, as indicated by their pKa of 15.7 and 16 respectively. Thus, sodium ethoxide and sodium hydroxide exist in an equilibrium that is closely balanced:
- CH3CH2OH + NaOH ⇌ CH3CH2ONa + H2O
Halogenation
Ethanol is not used industrially as a precursor to ethyl halides, but the reactions are illustrative. Ethanol reacts with
- CH3CH2OH + HCl → CH3CH2Cl + H2O
HCl requires a catalyst such as zinc chloride.[110] HBr requires
- CH3CH2OH + SOCl2 → CH3CH2Cl + SO2 + HCl
Upon treatment with halogens in the presence of base, ethanol gives the corresponding
- 4 Cl2 + CH3CH2OH → CCl3CHO + 5 HCl
- CCl3CHO + H2O → CCl3C(OH)2H
Oxidation
Ethanol can be oxidized to
Metabolism
Ethanol is similar to
Safety
Ethanol is very flammable and should not be used around an open flame.
Pure ethanol will irritate the skin and eyes.[132] Nausea, vomiting, and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage.[133] Atmospheric concentrations above one part per thousand are above the European Union occupational exposure limits.[133]
History
The fermentation of sugar into ethanol is one of the earliest biotechnologies employed by humans. Ethanol has historically been identified variously as spirit of wine or ardent spirits,[134] and as aqua vitae or 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 of alcoholic beverages. Dried residue on 9,000-year-old pottery found in China suggests that Neolithic people consumed alcoholic beverages.[135]
The inflammable nature of the exhalations of wine was already known to ancient natural philosophers such as Aristotle (384–322 BCE), Theophrastus (c. 371–287 BCE), and Pliny the Elder (23/24–79 CE).[136] However, this did not immediately lead to the isolation of ethanol, even despite the development of more advanced distillation techniques in second- and third-century Roman Egypt.[137] An important recognition, first found in one of the writings attributed to Jābir ibn Ḥayyān (ninth century CE), was that by adding salt to boiling wine, which increases the wine's relative volatility, the flammability of the resulting vapors may be enhanced.[138] The distillation of wine is attested in Arabic works attributed to al-Kindī (c. 801–873 CE) and to al-Fārābī (c. 872–950), and in the 28th book of al-Zahrāwī's (Latin: Abulcasis, 936–1013) Kitāb al-Taṣrīf (later translated into Latin as Liber servatoris).[139] In the twelfth century, recipes for the production of aqua 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.[140]
The works of
In
In 1796, German-Russian chemist
Ethanol was first prepared synthetically in 1825 by Michael Faraday. He found that sulfuric acid could absorb large volumes of coal gas.[149] He gave the resulting solution to Henry Hennell, a British chemist, who found in 1826 that it contained "sulphovinic acid" (ethyl hydrogen sulfate).[150] In 1828, Hennell and the French chemist Georges-Simon Serullas independently discovered that sulphovinic acid could be decomposed into ethanol.[151][152] Thus, in 1825 Faraday had unwittingly discovered that ethanol could be produced from ethylene (a component of coal gas) by acid-catalyzed hydration, a process similar to current industrial ethanol synthesis.[153]
Ethanol was used as lamp fuel in the U.S. as early as 1840, but a tax levied on industrial alcohol during the
Ethanol intended for industrial use is often produced from ethylene.[156] 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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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;
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Further reading
- Boyce JM, Pittet D (2003). "Hand Hygiene in Healthcare Settings". Atlanta, GA: Centers for Disease Control..
- Onuki S, Koziel JA, van Leeuwen J, Jenks WS, Grewell D, Cai L (June 2008). Ethanol production, purification, and analysis techniques: a review. 2008 ASABE Annual International Meeting. Providence, RI. Retrieved 16 February 2013.
- "Explanation of US denatured alcohol designations". Sci-toys.
- Lange, Norbert Adolph (1967). John Aurie Dean (ed.). Lange's Handbook of Chemistry (10th ed.). McGraw-Hill.
External links
- Alcohol (Ethanol) at The Periodic Table of Videos(University of Nottingham)
- International Labour Organization ethanol safety information
- National Pollutant Inventory – Ethanol Fact Sheet
- CDC – NIOSH Pocket Guide to Chemical Hazards – Ethyl Alcohol
- National Institute of Standards and Technology chemical data on ethanol
- Chicago Board of Trade news and market data on ethanol futures
- Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of ethanol
- Ethanol History A look into the history of ethanol
- ChemSub Online: Ethyl alcohol
- Industrial ethanol production process flow diagram using ethylene and sulphuric acid