Fusel oil, amyl alcohols

Fusel oil -amyl alcohols [AMYL ALCOHOLS] (Vol 2) -as congener m spirits [BEVERAGE SPIRITS DISTILLED] (Vol 4)... 

In the absence of any color, test io cc. of the sample in the same manner, using sufficient fusel oil, amyl alcohol or pentasol to nearly fill the tube, and shake several times. A deeply colored lower layer is an indication of a coal tar dye its identity should be confirmed by using the methods under 51. 

Absolute alcohol Industrial spirit Potable spirit Acetone Butanol Fusel oils (amyl alcohol) Spirit vinegar (10%)... 

ISOAMYL ALCOHOL Fermentation amyl alcohol, Fusel oil, Isopentyl alcohol, 3-MethyH-butanol Combustible Liquid 1 2 0... 

Many explanations of the presence of fusel oil in alcoholic fermentation have been given. Brefeld held that it was produced by decomposition of dead yeast bodies which begin to accumulate toward the end of alcoholic fermentation. Along this same line of thought is that of Ehrlich who made a study of yeast action on amino acids. He found that when leucine or iso leucine was present in the alcoholic fermentation of sugar both active and inactive amyl alcohol were produced as follows ... 

Iso-amyl alcohol (3 -methyl-1 -butanol) Fusel oil (higher alcohol), whiskey-like represents the main higher alcohol known as fusel oil. ... 

Three significant, commercial processes for the production of amyl alcohols include separation from fusel oils, chlorination of C-5 alkanes with subsequent hydrolysis to produce a mixture of seven of the eight isomers (Pennsalt) (91), and a low pressure 0x0 process, or hydroformylation, of C-4 olefins followed by hydrogenation of the resultant C-5 aldehydes. 

Fusel Oils. The original source of amyl alcohols was from fusel oil which is a by-product of the ethyl alcohol fermentation industry. Refined amyl alcohol from this source, after chemical treatment and distillation, contains about 85% 3-methyl-1-butanol and about 15% 2-methyl-1-butanol, both primary amyl alcohols. Only minor quantities of amyl alcohol are suppHed from this source today. A German patent discloses a distillative separation process for recovering 3-methyl-1-butanol from fusel oil (93). 

Chemical Designationis - Synonyms Fementation amyl alcohol Fusel oil Isobutylcarbinol Isopentyl alcohol 3-Methyl-l-butanol Potato-spirit oil Chemical Formula (CH3)2CHCH2CH20H. Observable Characteristics - Physical(asshipped) Liquid Color Colorless Odor. Mild odor alcoholic, non-residual. 

Commercial amyl alcohol is contained in fusel oil from fer mentation and consists mainly of isobutyl carbinol together with about 13 per cent, of secondary butyl carbinol, which renders the liquid optically active. It turns the plane of polarisation to the left (see p. 116). 

Synonyms AI3-15288 C-07328 EINECS 204-663-5 FEMA No. 2057 Fermentation amyl alcohol Fusel oil IP3 l-Hydroxy-3-methylbutane Isoamylol Isobutyl carbinol Isopentanol Isopentyl alcohol Methyl-3-butan-l-ol 2-Methyl-4-butanol 2-Methylbutan-4-ol 3-Methylbutanol 3-Methylbutan-l-ol 3-Methyl-l-butanol NSC 1029 Primary isoamyl alcohol Primary isobutyl alcohol UN 1105. 

Hydrolysis of Chlorinated Hydrocarbons. The production of oxygenated aliphatics by the hydrolysis of chlorinated hydrocarbons includes the synthetic glycerol process and the amyl alcohols process. Glycerol (7) is made from propylene via allyl chloride (CH2 CHCH2C1), and competes with glycerol made from fats and oils for use in dynamite and alkyd resins, as a tobacco humectant and cellophane plasticizer, in cosmetics and pharmaceuticals, and for other applications. Amyl alcohols have been made since 1926 by the alkali hydrolysis of a mixture of amyl chlorides, made by the chlorination of pentanes from natural gasoline. Production from this source far exceeds the supply from the fusel oil by-product of fermentation processes. Amyl alcohol and its derivatives are used mainly as solvents. 

Amyl Acetate or Amylacetic EsteKcommonly known as Banana Oil),C H. COOCH, mw 130.18- Several isomers are known of which n-amyl acetate and isoamyl acetate are the most important. They can be prepd by heating amyl alcohols with acetic acid in the presence of some sulfuric acid. Industrial methods of prepn are given in Ref 9,pp 102—3- Commercial products are usually mixts of n- and iso-amyl acetates. When amyl acetate is prepd from "fusel oil (a byproduct obtained in the manuf of ethyl ale by fermentation), the chief component is isoamyl acetate... 

Amyl alcohols can be prepd either from fusel oil or by a synthetic method which involves hydrolysis of amyl chloride, which in turn is prepd by the chlorination of a mixt of pentane and isopentane obtained from petroleum. The ale prepd by synthetic method has, according to Ref 5,p 147, the following props d 0.812 to 0.820 20°/20°, boiling range 120 to 130°, n20° 1.409 and fl p(open cup) 113°F(45°)... 

The oxo process is the principal one in practice today only minor quantities, mainly in Europe, are obtained from separation from fusel oil. ten-Amyl alcohol is produced on a commercial scale in lower volume by hydration of amylenes (Dow7. BASF). 

Tills is generally associated with the familiar alcoholic fermentation in which theoretically 100 parts of glucose are converted to 51.1 parts of ethyl alcohol (ethanol). 48.9 parts of carbon dioxide (CO/i. and heat. In addition, however, the anaerobic reaction also yields minor byproducts in small amounts—mainly glycerol, succinic acid, higher alcohols (fusel oil), 2,3-butanediol, and traces of acetaldehyde, acetic acid, and lactic acid. Fusel oil is a mixture of alcohols, including -propyl, -butyl, isobutyl, amyl, and isoamyl alcohols. 

Deamination 17 Examples of deamination and decarboxylation include conversion of amino acids to fusel oil (leucine to isoamyl alcohol, isoleucine to amyl alcohol, and phenylalanine to phenyl ethanol). Fusel oil formation is a normal function of all yeast fermentations (in alcoholic beverages, levels range from trace to 2200 parts per million). Deamination Glutamic acid to gamma-OH-butyric acid (S. cerevisiae). 

Acid Sulfates. Pasteur 6 and also Le Bel4 fractionated the cinchonine salts of the mixture of amyl hydrogen sulfates derived from fusel oil and effected a partial separation of the structurally isomeric alcohols. Krtiger 41 failed to resolve the alkaloid salts of the hydrogen sulfate of ethyl-n-propylcarbinol but Meth,42 after failures in other instances, finally effected a partial resolution of a-butyl hydrogen sulfate as the brucine salt. The method has proved to be impracticable for most alcohols 48 because the majority of alkyl hydrogen sulfates are unstable and inconvenient to handle. 

Amyl Alcohol (Pentanols, Pentyl Alcohols, Fusel Oil, and Potato Spirit) Molecular formula C5H11OH... 

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