Secondary isoamyl alcohol

METHYL-2-BUTANOL(SECONDARY ISOAMYL ALCOHOL) (582-75-4) Forms explosive mixture with air (flash point 95°F/35°C). Violent reaction with strong oxidizers. Reacts violently with aliphatic amines, alkalis, ammonium persulfate, boranes, bromine dioxide, isocyanates, nitric acid, perchlorates, permanganates, peroxides, sodium peroxide, sulfuric acid, uranium fluoride. Flow or agitation of substance may generate electrostatic charges due to low conductivity. 

SYNONYMS (Primary) fermentation amyl alcohol, isobutylcarbinol, isopentyl alcohol, 3-methyl-l-butanol, primary isoamyl alcohol (Secondary) 3-methyl-2-butanol, secondary isoamyl alcohol. 

Synonyms/Trade Names 3-Methyl-2-butanol, Secondary isoamyl alcohol ... 

Isoamyl alcohol (secondary) Formula (CH3)2CHCH(0H)CH3 CAS 6032-29-7 RTECS SA4900000 IDLH 500 ppm... 

Synonyms s-lsoamyl alcohol Isoamyl alcohol, secondary s-lsopentyl alcohol Isopropyl methyl carbinol 3-Methylbutan-2-ol... 

Erlenmeyer found that the butyl alcohol present in fusel oil yields iso-butyric acid (see below) on oxidation, and is therefore isobutyl alcohol, and he also showed that from isobutyl iodide the same valeric acid is obtained as from the amyl alcohol of fusel oil, which is therefore isoamyl alcohol, derived from dimethylethylmethane. Secondary butyl alcohol was first obtained as hydrate de butylene from erythritol by de Luynes. A. Lieben obtained it from zinc ethyl and dichloroethyl ether, and since he found that on oxidation it gives a ketone he recognised it as secondary butyl alcohol. Lieben and A. Rossi obtained normal butyl alcohol from butyric acid, which was converted into butyraldehyde by distilling calcium butyrate and calcium formate, and a solution of this reduced with a large amount of sodium amalgam. They give structural formulae for the four butyl alcohols, with the boiling-points. 

Yields of the primary alkyl acrylates vary somewhat, owing to occasional losses through formation of polymer, but are usually in the range of 85-99%. Some secondary alcohols react very slowly, others readily. The method has been applied to more than fifty alcohols, some of which (with percentage yields) are listed below ethyl, 99% isopropyl, 37% -amyl, 87% isoamyl, 95% -hexyl, 99% 4-methyl-2-pentyl, 95% 2-ethylhexyl, 95% capryl, 80% lauryl, 92% myristyl, 90% allyl, 70% fur-furyl, 86% citronellyl, 91% cyclohexyl, 93% benzyl, 81% (3-ethoxyethyl, 99% /S-(/3-phenoxyethoxy) ethyl (from diethylene glycol monophenyl ether), 88%. 

The alcohols above ethyl in the series are generally spoken of as higher alcohols. An extensive literature on their presence in brandy has developed because of their importance to the organoleptic character of brandy. Much less information is available for wines. The chief higher alcohols found are isoamyl (3-methyl-l-butanol), active amyl ((—)-2-methyl-l-butanol), -propyl (1-propanol), isobutyl (2-methyl-l-propa-nol), n-butyl (1-butanol), and (—) sec-butyl (2-butanol). Others doubtless occur and will be identified as better methods for their separation are developed. Buscarfins (1941) fractionated (under vacuum) a fusel oil from wine pomace and identified amyl, propyl, isobutyl, butyl, and isopropyl (2-propanol)alcohols as esters and higher alcohols up to decyl. No hi er secondary alcohols were found. The residue consisted of esters, fatty acids, furfural, cylic bases, and hydrocarbons. Only acids with an even number of carbon atoms were demonstrated. The unsaturated acids oleic and linoleic were present in small amounts, presumably from the seeds. Ethyl esters were more important in amount than amyl esters. There was 3% furfural, 5.5% fatty acids (free and esterified), 30.9% alcohols (free and esterified), and 1.6% hydrocarbons (terpene). Dupont and Dulou (1935) demonstrated sec-butyl alcohol in a technical propyl alcohol that had been produced from fusel oil. 

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