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Ethanol
IUPAC name	Ethanol
Other names	Ethyl alcohol; grain alcohol; hydroxyethane; drinking alcohol; ethyl hydrate
Identifiers
CAS number	[64-17-5]
RTECS number	KQ6300000
SMILES	CCO
Properties
Molecular formula	CH3CH2OH MolarMass = 46.06844(232) g/mol Neutral grain spirits refers to a clear liquid distilled at a high ethyl alcohol content. ... Image File history File links Gnome-globe. ... Image File history File links Ethanol-2D-skeletal. ... Image File history File links Download high resolution version (1100x900, 169 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Ethanol ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ...
Appearance	colorless clear liquid
Density	0.789 g/cm³, liquid
Melting point	−114.3 °C (158.8 K) For other uses, see Density (disambiguation). ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	78.4 °C (351.6 K) Italic text This article is about the boiling point of liquids. ...
Solubility in water	Fully miscible
Acidity (pKa)	15.9
Viscosity	1.200 mPa·s (cP) at 20.0 °C
Dipole moment	5.64 fC·fm (1.69 D) (gas)
Hazards
MSDS	External MSDS
EU classification	Flammable (F)
NFPA 704	4 0 0
R-phrases	R11
S-phrases	(S2), S7, S16
Flash point	286.15 K (13 °C or 55.4 °F)
Related compounds
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Ethanol, also called ethyl alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is best known as the type of alcohol found in alcoholic beverages and in thermometers. In common usage, it is often referred to simply as alcohol. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. ... For other uses, see Viscosity (disambiguation). ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... This page provides supplementary chemical data on ethanol. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... This page provides supplementary chemical data on ethanol. ... This page provides supplementary chemical data on ethanol. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... This page provides supplementary chemical data on ethanol. ... This page provides supplementary chemical data on ethanol. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. ... 900MHz, 21. ... Mass spectrometry (previously called mass spectroscopy (deprecated) or informally, mass-spec and MS) is an analytical technique that measures the mass-to-charge ratio of ions. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Flammable or Flammability refers to the ease at which a substance will ignite, causing fire or combustion. ... This article does not cite any references or sources. ... Alcoholic beverages are drinks containing ethanol, popularly called alcohol. ...

Ethanol is also known as EtOH, using the common organic chemistry notation of representing the ethyl group (C₂H₅) with Et. The National Institute on Alcohol Abuse and Alcoholism maintains an EtOH database.^[1] The National Institute on Alcohol Abuse and Alcoholism (NIAAA), as part of the U.S. National Institutes of Health, supports and conducts biomedical and behavioral research on the causes, consequences, treatment, and prevention of alcoholism and alcohol-related problems. ...

Ethanol is a straight-chain alcohol, and its molecular formula is C₂H₅OH. An alternative notation is CH₃-CH₂-OH, which indicates that the carbon of a methyl group (CH₃-) is attached to the carbon of a methylene group (-CH₂-), which is attached to the oxygen of a hydroxyl group (-OH). A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ...

Its empirical formula is C₂H₆O, a formula that it shares with dimethyl ether. In chemistry, the empirical formula of a chemical compound is a simple expression of the relative number of each type of atom in it. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... This article is about the chemical element and its most stable form, or dioxygen. ... Dimethyl ether, also known as methoxymethane, oxybismethane, methyl ether, wood ether, and DME, is a colorless gaseous ether with an ethereal odor. ...

Except for the use of fire, the fermentation of sugar into ethanol is very likely the earliest organic reaction known to humanity,^{[citation needed]} and the intoxicating effects of ethanol consumption have been known since ancient times. In modern times, ethanol intended for industrial use is also produced from byproducts of petroleum refining. Organic reactions are chemical reactions involving organic compounds. ...

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 an essential solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light and also as a fuel for internal combustion engines. A colored automobile engine The internal combustion engine is an engine in which the combustion of fuel and an oxidizer (typically air) occurs in a confined space called a combustion chamber. ...

History

Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages. Dried residues on 9000-year-old pottery found in China imply that alcoholic beverages were used even among Neolithic people.^[2] Its isolation as a relatively pure compound was first achieved by Muslim chemists who developed the art of distillation during the Abbasid caliphate, the most notable of whom were Jabir ibn Hayyan (Geber), Al-Kindi (Alkindus), and al-Razi (Rhazes, 865–925). Booze redirects here. ... An array of Neolithic artifacts, including bracelets, axe heads, chisels, and polishing tools. ... Alchemy in Islam differs from the general alchemy in certain ways, one of which is that Muslim alchemists didnt believe in the creation of life in the laboratory. ... Laboratory distillation set-up: 1: Heat source 2: Still pot 3: Still head 4: Thermometer/Boiling point temperature 5: Condenser 6: Cooling water in 7: Cooling water out 8: Distillate/receiving flask 9: Vacuum/gas inlet 10: Still receiver 11: Heat control 12: Stirrer speed control 13: Stirrer/heat plate... Mashriq Dynasties  Maghrib Dynasties  The Abbasid Caliphate Abbasid (Arabic: , ) is the dynastic name generally given to the caliph of Baghdad, the second of the two great Sunni dynasties of the Arab Empire, that overthrew the Umayyad caliphs from all but Spain. ... A caliphate (from the Arabic خلافة or khilāfah), is the Islamic form of government representing the political unity and leadership of the Muslim world. ... Jabir ibn Hayyan and Geber were also pen names of an anonymous 14th century Spanish alchemist: see Pseudo-Geber. ... For the Christian theologian, see Abd al-Masih ibn Ishaq al-Kindi. ... For other uses, see Razi. ...

Writings attributed to Jabir ibn Hayyan (721–815) mention the flammable vapors of boiled wine. Al-Kindi (801–873) unambiguously described the distillation of wine.^[3]

In 1796, Johann Tobias Lowitz obtained pure ethanol by filtering distilled ethanol through activated charcoal. Activated carbon Activated carbon, also called activated charcoal or activated coal, is a general term which covers carbon material mostly derived from charcoal. ...

Antoine Lavoisier described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1808 Nicolas-Théodore de Saussure determined ethanol's chemical formula.^[4] Fifty years later, Archibald Scott Couper published the structural formula of ethanol, which placed ethanol among the first chemical compounds to have their chemical structure determined.^[5] Lavoisier redirects here. ... Nicolas-Théodore de Saussure (14 October 1767 - 18 April 1845) was a Switzerland chemist and student of plant physiology who made seminal advances in phytochemistry. ... Archibald Scott Couper (1831-1892) was the author of On a New Chemical Theory, Philosophical Magazine 16, 104-116 (1858) [as excerpted in Alembic Club Reprint #21, On a New Chemical Theory and Researches on Salicylic Acid[1]] Friedrich August Kekulé von Stradonitz claimed to solve the structure of Benzene...

Ethanol was first prepared synthetically in 1826 through the independent efforts of Henry Hennel in Great Britain and S.G. Sérullas in France. In 1828, Michael Faraday prepared ethanol by acid-catalyzed hydration of ethylene, a process similar to that which is used today for industrial ethanol synthesis.^[6] Michael Faraday, FRS (September 22, 1791 – August 25, 1867) was an English chemist and physicist (or natural philosopher, in the terminology of that time) who contributed to the fields of electromagnetism and electrochemistry. ... In acid catalysis and base catalysis a chemical reaction is catalized by an acid or a base. ... Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ...

Ethanol was used as lamp fuel in the United States as early as 1840, but a tax levied on industrial alcohol during the Civil War made this use uneconomical. This tax was repealed in 1906,^[7] and from 1908 onward Ford Model T automobiles could be adapted to run on ethanol.^[8] With the advent of Prohibition in 1920 though, sellers of ethanol fuel were accused of being allied with moonshiners,^[7] and ethanol fuel again fell into disuse until late in the 20th century. Combatants United States of America (Union) Confederate States of America (Confederacy) Commanders Abraham Lincoln, Ulysses S. Grant Jefferson Davis, Robert E. Lee Strength 2,200,000 1,064,000 Casualties 110,000 killed in action, 360,000 total dead, 275,200 wounded 93,000 killed in action, 258,000 total... The Ford Model T (colloquially known as the Tin Lizzie and the Flivver) was an automobile produced by Henry Fords Ford Motor Company from 1908 through 1927. ... The term Prohibition, also known as A Dry Law, refers to a law in a certain country by which the manufacture, transportation, import, export, and sale of alcoholic beverages is restricted or illegal. ... Revenue men at the site of moonshine stills, Kentucky, 1911 or earlier For other uses, see Moonshine (disambiguation). ...

Physical properties

Ethanol burning in a shallow dish.

Ethanol is a volatile, flammable, colorless liquid that has a strong characteristic odor. It burns with a smokeless blue flame that is not always visible in normal light. Image File history File linksMetadata Download high-resolution version (1600x1200, 192 KB) Combustion of ethanol in evaporating dish Kyanite 01:24, 15 November 2006 (UTC) I, the creator of this work, hereby release it into the public domain. ... Image File history File linksMetadata Download high-resolution version (1600x1200, 192 KB) Combustion of ethanol in evaporating dish Kyanite 01:24, 15 November 2006 (UTC) I, the creator of this work, hereby release it into the public domain. ... Flammable or Flammability refers to the ease at which a substance will ignite, causing fire or combustion. ...

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. // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ...

Ethanol is a versatile solvent, miscible with water and with many organic solvents, including acetic acid, acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol, nitromethane, pyridine, and toluene.^[9][10] It is also miscible with light aliphatic hydrocarbons, such as pentane and hexane, and with aliphatic chlorides such as trichloroethane and tetrachloroethylene.^[10] The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... R-phrases , S-phrases , , , Flash point 43 °C Related Compounds Related carboxylic; acids Formic acid; Propionic acid; Butyric acid Related compounds acetamide; ethyl acetate; acetyl chloride; acetic anhydride; acetonitrile; acetaldehyde; ethanol; thioacetic acid; acetylcholine; acetylcholinesterase Supplementary data page Structure and properties n, εr, etc. ... For other uses, see Acetone (disambiguation). ... Benzene, or Benzol (see also Benzine), is an organic chemical compound and a known carcinogen with the molecular formula C6H6. ... R-phrases , , , , S-phrases , , , , , Flash point Non flammable Supplementary data page Structure and properties n, εr, etc. ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... This article is about the chemical compound. ... Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. ... Glycerine, Glycerin redirects here. ... Flash point 35 °C R/S statement R: S: RTECS number PA9800000 Related compounds Related nitro compounds nitroethane Related compounds methyl nitrite methyl nitrate Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references Nitromethane is an organic... Pyridine is a chemical compound with the formula C5H5N. It is a liquid with a distinctively putrid odour. ... Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. ... Pentane (also known as amyl hydride or skellysolve) is an alkane hydrocarbon with the chemical formula CH3(CH2)3CH3. ... the 3rd ingredient in big mac ... The chemical compound 1,1,1-trichloroethane is a chlorinated hydrocarbon that was until recently widely used as an industrial solvent. ... Tetrachloroethylene Cl2C=CCl2 is a manufactured chemical compound that is widely used for the dry cleaning of fabrics and for metal-degreasing. ...

Ethanol’s miscibility with water contrasts with that of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as the number of carbons increases.^[11]

Hydrogen bonding causes pure ethanol to be hygroscopic to the extent that it readily absorbs water from the air. The polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds, notably sodium and potassium hydroxides, magnesium chloride, calcium chloride, ammonium chloride, ammonium bromide, and sodium bromide.^[10] Sodium and potassium chlorides are slightly soluble in ethanol.^[10] Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including most essential oils^[12] and numerous flavoring, coloring, and medicinal agents. A hygroscopic substance is a substance that absorbs water readily from its surroundings. ... Sodium hydroxide (NaOH), also known as lye, caustic soda and (incorrectly, according to IUPAC nomenclature)[1] sodium hydrate, is a caustic metallic base. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... Magnesium chloride is composed of magnesium and chlorine and is a typical ionic halide, being highly polar and soluble in water. ... R-phrases S-phrases , , Related Compounds Other anions calcium fluoride calcium bromide calcium iodide Other cations magnesium chloride strontium chloride Supplementary data page Structure and properties n, εr, etc. ... Ammonium chloride (NH4Cl) (also Sal Ammoniac, salmiac, nushadir salt, zalmiak, sal armagnac, sal armoniac, salmiakki, salmiak and salt armoniack) is, in its pure form, a clear white water-soluble crystalline salt of ammonia with a biting, slightly sour taste. ... Ammonium bromide, NH4Br, can be prepared by the direct action of hydrogen bromide on ammonia. ... Sodium bromide is the chemical compound with the formula NaBr. ... Sodium chloride, also known as common salt, table salt, or halite, is a chemical compound with the formula NaCl. ... The chemical compound potassium chloride (KCl) is a metal halide salt composed of potassium and chlorine. ... An essential oil is any concentrated, hydrophobic liquid containing volatile aroma compounds from plants, which are called aromatic herbs or aromatic plants. ...

Two unusual phenomena are associated with mixtures of ethanol and water. Ethanol-water mixtures have less volume than the sum of their individual components. Mixing equal volumes of ethanol and water results in only 1.92 volumes of mixture.^[13][9] 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. This box:      Surface tension is a property of the surface of a liquid that causes it to behave as an elastic sheet. ... The phenomenon called tears of wine is manifested as a ring of clear liquid, near the top of a glass of wine, from which droplets form and flow back into the wine. ...

Mixtures of ethanol and water that contain more than about 50% ethanol are flammable and easily ignited. Alcoholic proof is a widely used measure of how much ethanol (i.e., alcohol) such a mixture contains. In the 18th century, proof was determined by adding a liquor (such as rum) to gunpowder. If the gunpowder burned, that was considered to be “100% proof” that it was “good” liquor — hence it was called “100 proof.” Flammable or Flammability refers to the ease at which a substance will ignite, causing fire or combustion. ... Alcoholic proof is a measure of how much ethanol is in an alcoholic beverage, and is approximately twice the percentage of alcohol by volume (ABV, the unit that is commonly used presently). ... Caribbean rum, circa 1941 Rum is a distilled beverage made from sugarcane by-products such as molasses and sugarcane juice by a process of fermentation and distillation. ...

Ethanol-water solutions that contain less than 50% ethanol may also be flammable if the solution is first heated. Some cooking methods call for wine to be added to a hot pan, causing it to flash boil into a vapor, which is then ignited to burn off excess alcohol. For other uses, see Wine (disambiguation). ...

Ethanol is slightly more refractive than water, having a refractive index of 1.36242 (at λ=589.3 nm and 18.35 °C).^[9] The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ...

Chemical properties

Chemical structure of ethanol

For more details on this topic, see Alcohol.

Ethanol is classified as a primary alcohol, meaning that the carbon to which its hydroxyl group is attached has at least two hydrogen atoms attached to it as well. Image File history File links This is a lossless scalable vector image. ... Image File history File links This is a lossless scalable vector image. ... This article does not cite any references or sources. ...

The chemistry of ethanol is largely that of its hydroxyl group. // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ...

Acid-base chemistry

Ethanol's hydroxyl casues the molecule to be slightly basic. It is however,so very slightly basic it is almost neutral, like pure water. The pH of 100% ethanol is 7.33, compared to 7.00 for pure water. Ethanol can be quantitatively converted to its conjugate base, the ethoxide ion (CH₃CH₂O⁻), by reaction with an alkali metal such as sodium:^[11] For other uses, see PH (disambiguation). ... In the field of chemistry, in the Brønsted-Lowry (protonic) theory of acids and bases, a conjugate base is the basic member, X-, of a pair of compounds that differ only by the presence or absence of a proton at a certain position. ... An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. ... The alkali metals are a series of elements comprising Group 1 (IUPAC style) of the periodic table: lithium (Li), sodium (Na), potassium (K), rubidium (Rb), caesium (Cs), and francium (Fr). ... For sodium in the diet, see Salt. ...

2CH₃CH₂OH + 2Na → 2CH₃CH₂ONa + H₂

or a very strong base such as sodium hydride: For sodium in the diet, see Salt. ... This article is about the chemistry of hydrogen. ...

CH₃CH₂OH + NaH → CH₃CH₂ONa + H₂

This article is about the chemistry of hydrogen. ...

Halogenation

Ethanol reacts with hydrogen halides to produce ethyl halides such as ethyl chloride and ethyl bromide: It has been suggested that this article or section be merged with Hydrohalic acid. ... Tetrafluoroethane (a haloalkane) is a clear liquid which boils well below room temperature (as seen here) and can be extracted from common canned air canisters by simply inverting them during use. ... Ethyl chloride is a chemical compound once widely used in producing tetraethyl lead, a gasoline additive. ... R-phrases , , S-phrases , Flash point −20 °C Autoignition temperature 511 °C Explosive limits 6. ...

CH₃CH₂OH + HCl → CH₃CH₂Cl + H₂O

HCl reaction requires a catalyst such as zinc chloride.^[14] Hydrogen chloride in the presence of their respective zinc chloride is known as Lucas reagent.^[11][14] Hydrochloric acid is the aqueous solution of hydrogen chloride gas (HCl). ... Ethyl chloride is a chemical compound once widely used in producing tetraethyl lead, a gasoline additive. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Zinc chloride (ZnCl2) is a colorless or white compound of zinc and chlorine that is extremely hygroscopic. ...

CH₃CH₂OH + HBr → CH₃CH₂Br + H₂O

HBr requires refluxing with a sulfuric acid catalyst.^[14] It has been suggested that this article or section be merged into hydrogen bromide. ... R-phrases , , S-phrases , Flash point −20 °C Autoignition temperature 511 °C Explosive limits 6. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Reflux is a technique used in industrial and laboratory distillations. ... Sulfuric acid, (also known as sulphuric acid) H2SO4, is a strong mineral acid. ...

Ethyl halides can also be produced by reacting ethanol with more specialized halogenating agents, such as thionyl chloride for preparing ethyl chloride, or phosphorus tribromide for preparing ethyl bromide.^[11][14] Halogenation is a chemical reaction that replaces a hydrogen atom with a halogen atom. ... R-phrases , , , S-phrases , , , Flash point non flammable Supplementary data page Structure and properties n, εr, etc. ... Phosphorus tribromide is a colourless liquid with the formula PBr3. ...

CH₃CH₂OH + SOCl₂ → CH₃CH₂Cl + SO₂ + HCl

Ester formation

Under acid-catalyzed conditions, ethanol reacts with carboxylic acids to produce ethyl esters and water: Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... For other uses, see Ester (disambiguation). ...

RCOOH + HOCH₂CH₃ → RCOOCH₂CH₃ + H₂O

For this reaction to produce useful yields it is necessary to remove water from the reaction mixture as it is formed. Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... For other uses, see Ester (disambiguation). ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ...

Ethanol can also form esters with inorganic acids. Diethyl sulfate and triethyl phosphate, prepared by reacting ethanol with sulfuric and phosphoric acid respectively, are both useful ethylating agents in organic synthesis. Ethyl nitrite, prepared from the reaction of ethanol with sodium nitrite and sulfuric acid, was formerly a widely-used diuretic. R-phrases , , , S-phrases , Flash point 104 °C RTECS number WS7875000 Supplementary data page Structure and properties n, εr, etc. ... The compound triethyl phosphate has formula (C2H5)3PO4. ... Sulfuric acid, (also known as sulphuric acid) H2SO4, is a strong mineral acid. ... This article is about orthophosphoric acid. ... Organic synthesis is the construction of organic molecules via chemical processes. ... The chemical compound ethyl nitrite is an Alkyl nitrite. ... Sodium nitrite, with chemical formula NaNO2, is used as a color fixative and preservative in meats and fish. ... Sulfuric acid, (also known as sulphuric acid) H2SO4, is a strong mineral acid. ... This illustration shows where some types of diuretics act, and what they do. ...

Dehydration

Strong acid desiccants, such as sulfuric acid, cause ethanol's dehydration to form either diethyl ether or ethylene: This article is about the chemical compound. ... Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ...

2 CH₃CH₂OH → CH₃CH₂OCH₂CH₃ + H₂O

CH₃CH₂OH → H₂C=CH₂ + H₂O

Which product, diethyl ether or ethylene, predominates depends on the precise reaction conditions. This article is about the chemical compound. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ...

Oxidation

Ethanol can be oxidized to acetaldehyde, and further oxidized to acetic acid. In the human body, these oxidation reactions are catalyzed by enzymes. In the laboratory, aqueous solutions of strong oxidizing agents, such as chromic acid or potassium permanganate, oxidize ethanol to acetic acid, and it is difficult to stop the reaction at acetaldehyde at high yield. Ethanol can be oxidized to acetaldehyde, without over oxidation to acetic acid, by reacting it with pyridinium chromic chloride.^[14] R-phrases , , S-phrases , , , Flash point −39 °C Autoignition temperature 185 °C RTECS number AB1925000 Supplementary data page Structure and properties n, εr, etc. ... R-phrases , S-phrases , , , Flash point 43 °C Related Compounds Related carboxylic; acids Formic acid; Propionic acid; Butyric acid Related compounds acetamide; ethyl acetate; acetyl chloride; acetic anhydride; acetonitrile; acetaldehyde; ethanol; thioacetic acid; acetylcholine; acetylcholinesterase Supplementary data page Structure and properties n, εr, etc. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... In chemistry, chromic acid is a chromium (Cr) compound, yet to be isolated, with the formula H2CrO4. ... Potassium permanganate is the chemical compound KMnO4. ... Pyridinium chlorochromate, a reddish orange solid reagent, is used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. ...

The direct oxidation of ethanol to acetic acid using chromic acid is given below.

C₂H₅OH + 2[O] → CH₃COOH + H₂O

The oxidation product of ethanol, acetic acid, is spent as nutrient by the human body as acetyl CoA, where the acetyl group can be spent as energy or used for biosynthesis. Acetyl-CoA is an important molecule in metabolism, used in many biochemical reactions. ...

Chlorination

When exposed to chlorine, ethanol is both oxidized and its alpha carbon chlorinated to form the compound, chloral. General Name, symbol, number chlorine, Cl, 17 Chemical series nonmetals Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... The Alpha carbon refers to the first carbon after the carbon that attaches to the functional group. ... Chloral is a colourless narcotic liquid, obtained at first by the action of chlorine on alcohol; treated with water it produces chloral hydrate. ...

4Cl₂ + C₂H₅OH → CCl₃CHO + 5HCl

Combustion

Combustion of ethanol forms carbon dioxide and water: This article is about the chemical reaction combustion. ... Carbon dioxide (chemical formula: ) is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ...

C₂H₅OH(g) + 3 O₂(g) → 2 CO₂(g) + 3 H₂O(l) (ΔH_r = −1409 kJ/mol^[15])

Production

94% denatured ethanol sold in a bottle for household use.

Ethanol is produced both as a petrochemical, through the hydration of ethylene, and biologically, by fermenting sugars with yeast.^[16] Which process is more economical is dependent upon the prevailing prices of petroleum and of grain feed stocks. Download high resolution version (480x640, 38 KB) Wikipedia does not have an article with this exact name. ... Download high resolution version (480x640, 38 KB) Wikipedia does not have an article with this exact name. ... Petrochemicals are chemical products made from raw materials of petroleum (hydrocarbon) origin. ... Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ... For other uses, see Fermentation. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic micro organisms classified in the kingdom Fungi, with about 1,500 species described;[1] they dominate fungal diversity in the oceans. ...

Ethylene hydration

Ethanol for use as industrial feedstock is most often made from petrochemical feed stocks, typically by the acid-catalyzed hydration of ethylene, represented by the chemical equation Petrochemicals are chemical products made from raw materials of petroleum (hydrocarbon) origin. ... For other uses, see acid (disambiguation). ... Catalyst redirects here. ... Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ... A chemical equation is a symbolic representation of a chemical reaction. ...

C₂H_4(g) + H₂O_(g) → CH₃CH₂OH_(l)

The catalyst is most commonly phosphoric acid,^[17] adsorbed onto a porous support such as diatomaceous earth or charcoal. This catalyst was first used for large-scale ethanol production by the Shell Oil Company in 1947.^[18] The reaction is carried out at with an excess of high pressure steam at 300 °C. Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... This article is about orthophosphoric acid. ... Not to be confused with absorption. ... A sample of diatomaceous earth Diatomaceous earth (IPA: , also known as DE, diatomite, diahydro, kieselguhr, kieselgur and Celite) is a naturally occurring, soft, chalk-like sedimentary rock that is easily crumbled into a fine white to off-white powder. ... Charcoal is the blackish residue consisting of impure carbon obtained by removing water and other volatile constituents from animal and vegetation substances. ... The Shell emblem known as the Pecten Shell Oil Company (SOC) is the Houston, Texas based wholly-owned subsidiary of Royal Dutch Shell. ...

In an older process, first practiced on the industrial scale in 1930 by Union Carbide,^[19] but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentrated sulfuric acid to produce ethyl sulfate, which was then hydrolyzed to yield ethanol and regenerate the sulfuric acid:^[14] Union Carbide Corporation (Union Carbide) is one of the oldest chemical and polymers companies in the United States, and currently has more than 3,800 employees. ... Sulfuric acid, (also known as sulphuric acid) H2SO4, is a strong mineral acid. ... Sulfovinic acid or ethyl sulfate is an organic chemical compound used as intermediate in the production of ethanol from ethylene. ... Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ...

C₂H₄ + H₂SO₄ → CH₃CH₂SO₄H

CH₃CH₂SO₄H + H₂O → CH₃CH₂OH + H₂SO₄

Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ... Sulfuric acid, (also known as sulphuric acid) H2SO4, is a strong mineral acid. ... Sulfovinic acid or ethyl sulfate is an organic chemical compound used as intermediate in the production of ethanol from ethylene. ... Sulfovinic acid or ethyl sulfate is an organic chemical compound used as intermediate in the production of ethanol from ethylene. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Sulfuric acid, (also known as sulphuric acid) H2SO4, is a strong mineral acid. ...

Fermentation

For more details on this topic, see Ethanol fermentation.

Ethanol for use in alcoholic beverages, and the vast majority of ethanol for use as fuel, is produced by fermentation. When certain species of yeast, most importantly, Saccharomyces cerevisiae, metabolize sugar in the absence of oxygen, they produce ethanol and carbon dioxide. The chemical equation below summarizes the conversion: Beer - A Product of Ethanol Fermentation Ethanol fermentation is the biological process by which sugars such as glucose, fructose, and sucrose, are converted into ethanol and carbon dioxide. ... Booze redirects here. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic micro organisms classified in the kingdom Fungi, with about 1,500 species described;[1] they dominate fungal diversity in the oceans. ... Binomial name Meyen ex E.C. Hansen Saccharomyces cerevisiae is a species of budding yeast. ... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ... Polysaccharides (sometimes called glycans) are relatively complex carbohydrates. ... This article is about the chemical element and its most stable form, or dioxygen. ... Carbon dioxide (chemical formula: ) is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ...

C₆H₁₂O₆ → 2 CH₃CH₂OH + 2 CO₂

The process of culturing yeast under conditions to produce alcohol is called fermentation. Ethanol's toxicity to yeast limits the ethanol concentration obtainable by brewing. The most ethanol-tolerant strains of yeast can survive up to approximately 15% ethanol by volume.^[20] Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. ... Carbon dioxide (chemical formula: ) is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ... Fermentation in progress Fermentation typically refers to the conversion of sugar to alcohol using yeast. ...

The fermentation process must exclude oxygen. If oxygen is present, yeast undergo aerobic respiration which produces carbon dioxide and water rather than ethanol. This article or section should be merged with aerobic metabolism. ... Carbon dioxide (chemical formula: ) is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ...

In order to produce ethanol from starchy materials such as cereal grains, 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. For fuel ethanol, the hydrolysis of starch into glucose can be accomplished more rapidly by treatment with dilute sulfuric acid, fungally produced amylase, or some combination of the two.^[21] Cereal crops are mostly grasses cultivated for their edible seeds (actually a fruit called a grain, technically a caryopsis). ... Starch (CAS# 9005-25-8, chemical formula (C6H10O5)n,[1]) is a mixture of amylose and amylopectin (usually in 20:80 or 30:70 ratios). ... For other uses, see Beer (disambiguation). ... Malted barley Malting is a process applied to cereal grains, in which the grains are made to germinate and then are quickly dried before the plant develops. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Amylase is the name given to glycoside hydrolase enzymes that break down starch into glucose molecules. ... Mashing is a stage in the brewing process where grains are steeped in water at specific temperatures, to facilitate enzyme activity and starch conversion. ... Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ...

Cellulosic ethanol

Main article: Cellulosic ethanol

Sugars for ethanol fermentation can be obtained from cellulose.^[22][23] Until recently, however, the cost of the cellulase enzymes capable of hydrolyzing cellulose has been prohibitive. The Canadian firm Iogen brought the first cellulose-based ethanol plant on-stream in 2004.^[24] Its primary consumer so far has been the Canadian government, which, along with the United States Department of Energy, has invested heavily in the commercialization of cellulosic ethanol. Deployment of this technology could turn a number of cellulose-containing agricultural byproducts, such as corncobs, straw, and sawdust, into renewable energy resources. Other enzyme companies are developing genetically engineered fungi that produce large volumes of cellulase, xylanase, and hemicellulase enzymes. These would convert agricultural residues such as corn stover, wheat straw, and sugar cane bagasse and energy crops such as switchgrass into fermentable sugars.^[25] Cellulosic ethanol (also called lignocellulosic ethanol/ ceetoh and ceetol) is a type of biofuel produced from lignocellulose, a structural material that comprises much of the mass of plants. ... Beer - A Product of Ethanol Fermentation Ethanol fermentation is the biological process by which sugars such as glucose, fructose, and sucrose, are converted into ethanol and carbon dioxide. ... Cellulose as polymer of β-D-glucose Cellulose in 3D Cellulose (C6H10O5)n is a polysaccharide of beta-glucose. ... Cellulase is an enzyme complex which breaks down cellulose to beta-glucose. ... Iogen Corporation is a Canadian company located in Ottawa, Ontario that was founded by Patrick Foody. ... The United States Department of Energy (DOE) is a Cabinet-level department of the United States government responsible for energy policy and nuclear safety. ... Freshly picked corn on US farm Corn sample from USDA A corncob is the central core of a maize (Zea mays ssp. ... Bales of straw bundles of rice straw Pile of straw bales, sheltered under a tarpaulin Straw is an agricultural byproduct, the dry stalk of a cereal plant, after the nutrient grain or seed has been removed. ... Sawdust is composed of fine particles of wood. ... Binomial name L. Switchgrass (Panicum virgatum) is a warm season grass and is one of the dominant species of the central North American tallgrass prairie. ...

Cellulose-bearing materials typically also contain other polysaccharides, including hemicellulose. When hydrolyzed, hemicellulose decomposes into mostly five-carbon sugars such as xylose. S. cerevisiae, the yeast most commonly used for ethanol production, cannot metabolize xylose. Other yeasts and bacteria are under investigation to ferment xylose and other pentoses into ethanol.^[26] Polysaccharides (sometimes called glycans) are relatively complex carbohydrates. ... A hemicellulose can be any of several heteropolymers (matrix polysaccharides) present in almost all cell walls along with cellulose. ... Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ... Xylose or wood sugar is an aldopentose — a monosaccharide containing five carbon atoms and including an aldehyde functional group. ... A pentose is a monosaccharide with five carbon atoms. ...

On January 14, 2008, General Motors announced a partnership with Coskata, Inc. The goal is to produce cellulosic ethanol cheaply, with an eventual goal of US$1 per U.S. gallon ($0.30/L) for the fuel. The partnership plans to begin producing the fuel in large quantity by the end of 2008. By 2011 a full-scale plant will come on line, capable of producing 50 to 100 million gallons of ethanol a year (200–400 ML/a).^[27] is the 14th day of the year in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance with the Gregorian calendar. ... General Motors Corporation, also known as GM, is a multinational corporation headquartered in the United States and has been the worlds largest and most dominant automaker since 1931 till the second half of 2007, surpassed by Toyota; as well as the global industry sales leader for 77 years. ... A megalitre (Ml or alternatively ML), also spelled megaliter, is one million (1,000,000) litres in the metric system. ... A year (from Old English gÄ“r) is the time between two recurrences of an event related to the orbit of the Earth around the Sun. ...

Hemp Easily Provides alcohol, Cellulose ethanol fuel can be made from stalks, and the fermentation of the plant as a whole, respectively. The energy from hemp may be high based on acreage or weight, but can be low based on the volume of the light weight harvested hemp.[citation needed] It does, however, produce more energy per acre per year than corn, sugar, flax, or any other crop currently grown for ethanol or biodiesel.[citation needed] http://en.wikipedia.org/wiki/Hemp

Prospective technologies

The anaerobic bacterium Clostridium ljungdahlii, recently discovered in commercial chicken wastes, can produce ethanol from single-carbon sources including synthesis gas, a mixture of carbon monoxide and hydrogen that can be generated from the partial combustion of either fossil fuels or biomass. Use of these bacteria to produce ethanol from synthesis gas has progressed to the pilot plant stage at the BRI Energy facility in Fayetteville, Arkansas.^[28] An anaerob