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Isobutanol
Isobutanol ( IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as ''i''-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and ''tert''-butanol, all of which are important industrially. Production Isobutanol is produced by the carbonylation of propylene. Two methods are practiced industrially, hydroformylation is more common and generates a mixture of isobutyraldehyde and butyraldehyde: :CH3CH=CH2 + CO + H2 → CH3CH2CH2CHO The reaction is catalyzed by cobalt or rhodium complexes. The resulting aldehydes are hydrogenated to the alcohols, which are then separated. In Reppe carbonylation, the same products are obtained, but the hydrogenation is effected by the water-gas shift reaction.. Laboratory synthesis Propanol and methanol can be reacted to produce isobutyl alcohol via Guerb ...
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Butanol Fuel
220px, Butanol, a C-4 hydrocarbon is a promising bio-derived fuel, which shares many properties with gasoline. Butanol may be used as a fuel in an internal combustion engine. It is more similar to gasoline than it is to ethanol. A C4-hydrocarbon, butanol is a drop-in fuel and thus works in vehicles designed for use with gasoline without modification. Both ''n''-butanol and isobutanol have been studied as possible fuels. Both can be produced from biomass (as "biobutanol" ) as well as from fossil fuels (as "petrobutanol"). The chemical properties depend on the isomer (''n''-butanol or isobutanol), not on the production method. Although intriguing in many ways, butanol fuel is rarely economically competitive. Genetically modified organisms Obtaining higher yields of butanol involves manipulation of the metabolic networks using metabolic engineering and genetic engineering. While significant progress has been made fermentation pathways for producing butanol remain inefficient. T ...
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Butanol
Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4 H9 O H, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, ''n''-BuOH, ''i''-BuOH, and ''t''-BuOH). These are ''n''-butanol, 2 stereoisomers of sec-butanol, isobutanol and ''tert''-butanol. Butanol is primarily used as a solvent and as an intermediate in chemical synthesis, and may be used as a fuel. Biologically produced butanol is called biobutanol, which may be ''n''-butanol or isobutanol. Isomers The unmodified term ''butanol'' usually refers to the straight chain isomer with the alcohol functional group at the terminal carbon, which is also known as ''n''-butanol or 1-butanol. The straight chain isomer with the alcohol at an internal carbon is ''sec''-butanol or 2-butanol. The branched isomer wit ...
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Isobutyraldehyde
Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). Isobutyraldehyde is made, often as a side-product, by the hydroformylation of propene. Its odour is described as that of wet cereal or straw. It undergoes the Cannizaro reaction even though it has alpha hydrogen atom. It is a colorless volatile liquid. Synthesis Isobutyraldehyde is produced industrially by the hydroformylation of propene. Several million tons are produced annually.Boy Cornils, Richard W. Fischer, Christian Kohlpaintner "Butanals" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. Biological routes In the context of butanol fuel, isobutyraldehyde is of interest as a precursor to isobutanol. ''E. coli'' as well as several other organisms has been genetically modified to produce isobutanol. α- Ketoisovalerate, derived from oxidative deamination of valine, is prone to decarboxylation to give isobut ...
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N-Butanol
1-Butanol, also known as butan-1-ol or ''n''-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and ''tert''-butanol. The unmodified term butanol usually refers to the straight chain isomer. 1-Butanol occurs naturally as a minor product of the ethanol fermentation of sugars and other saccharides and is present in many foods and drinks... It is also a permitted artificial flavorant in the United States, used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods, and cordials. It is also used in a wide range of consumer products. The largest use of 1-butanol is as an industrial intermediate, particularly for the manufacture of butyl acetate (itself an artificial flavorant and industrial solvent). It is a petrochemical derived from propylene. Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000 to ...
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1-butanol
1-Butanol, also known as butan-1-ol or ''n''-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and ''tert''-butanol. The unmodified term butanol usually refers to the straight chain isomer. 1-Butanol occurs naturally as a minor product of the ethanol fermentation of sugars and other saccharides and is present in many foods and drinks... It is also a permitted artificial flavorant in the United States, used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods, and cordials. It is also used in a wide range of consumer products. The largest use of 1-butanol is as an industrial intermediate, particularly for the manufacture of butyl acetate (itself an artificial flavorant and industrial solvent). It is a petrochemical derived from propylene. Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000  ...
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2-Butanol
2-Butanol, or ''sec''-butanol, is an organic compound with formula C H3CH( OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and ''tert''-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (''R'')-(−)-2-butanol and (''S'')-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture. This secondary alcohol is a flammable, colorless liquid that is soluble in three parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. Manufacture and applications 2-Butanol is manufactured industrially by the hydration of 1-butene or 2-butene: : Sulfuric acid is used as a catalyst for this conversion.. In the laboratory it can be prepared via Grignard reaction by reacting ethylmagnesium bromide with acetaldehyde in dried diethyl ether or tetrahydrofuran. Although some ...
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Ketoisovalerate
α-Ketoisovaleric acid is an organic compound with the formula (CH3)2CHC(O)CO2H. It is a ketoacid. With a melting point just above room temperature, it is usually an oil or semi-solid. The compound is colorless. It is a metabolite of valine and a precursor to pantothenic acid, a prosthetic group found in several cofactors. In the biological context, is usually encountered as its conjugate base ketoisovalerate, (CH3)2CHC(O)CO2−. Synthesis and reactions α-Ketoisovalerate undergoes hydroxymethylation to give ketopantoate: :(CH3)2CHC(O)CO2− + CH2O → HOCH2(CH3)2CC(O)CO2− This conversion is catalyzed by ketopantoate hydroxymethyltransferase. Like many α-ketoacids, α-ketoisovaleric acid is prone to decarboxylation to give isobutyraldehyde: :(CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2 Genetic engineering has been used to produce the biofuel isobutanol Isobutanol ( IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (someti ...
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Tert-Butanol
''tert''-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as ''t''-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. ''tert''-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether. Natural occurrence ''tert''-Butyl alcohol has been identified in beer and chickpeas. It is also found in cassava, which is used as a fermentation ingredient in certain alcoholic beverages. Preparation ''tert''-Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production. It can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride. Purification cannot be performed by simple distillation due to formation of an azeotrope with water, although initial drying of the solvent containing large amounts of water is performed by adding ...
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2-butanol
2-Butanol, or ''sec''-butanol, is an organic compound with formula C H3CH( OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and ''tert''-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (''R'')-(−)-2-butanol and (''S'')-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture. This secondary alcohol is a flammable, colorless liquid that is soluble in three parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. Manufacture and applications 2-Butanol is manufactured industrially by the hydration of 1-butene or 2-butene: : Sulfuric acid is used as a catalyst for this conversion.. In the laboratory it can be prepared via Grignard reaction by reacting ethylmagnesium bromide with acetaldehyde in dried diethyl ether or tetrahydrofuran. Although some ...
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Isobutyl Acetate
The chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate (IUPAC name) or β-methylpropyl acetate, is a common solvent. It is produced from the esterification of isobutanol with acetic acid. It is used as a solvent for lacquer and nitrocellulose. Like many esters it has a fruity or floral smell at low concentrations and occurs naturally in raspberries, pears and other plants. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache. A common method for preparing isobutyl acetate is Fischer esterification Fischer is a German occupational surname, meaning fisherman. The name Fischer is the fourth most common German surname. The English version is Fisher. People with the surname A * Abraham Fischer (1850–1913) South African public official * ..., where precursors isobutyl alcohol and acetic acid are heated in the presence of a strong acid. Isobutyl acetate ...
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Tert-Butanol
''tert''-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as ''t''-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. ''tert''-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether. Natural occurrence ''tert''-Butyl alcohol has been identified in beer and chickpeas. It is also found in cassava, which is used as a fermentation ingredient in certain alcoholic beverages. Preparation ''tert''-Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production. It can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride. Purification cannot be performed by simple distillation due to formation of an azeotrope with water, although initial drying of the solvent containing large amounts of water is performed by adding ...
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