Amyl alcohol

Amyl alcohol is an organic compound with the formula C5H11OH. All eight isomers of amyl alcohol are known:

:

Three of these alcohols, active amyl alcohol, methyl (n) propyl carbinol, and methyl isopropyl carbinol, are optically active, as they contain an asymmetric carbon atom.

The most important is isobutyl carbinol, this being the chief constituent of fermentation amyl alcohol, and consequently a constituent of fusel oil. It can be separated from fusel oil by shaking with strong brine solution, separating the oily layer from the brine layer and distilling it, the portion boiling between 125 and 140 °C. being collected. For further purification it may be shaken with hot lime water, the oily layer separated, dried with calcium chloride and fractionated, the fraction boiling between 128 and 132 °C only being collected. It may be synthesized from isobutanol by conversion into isovaleraldehyde, which is subsequently reduced to isobutyl carbinol by means of sodium amalgam.

It is a colourless liquid of density 0.8247 g/cm³ (0 °C), boiling at 131.6 °C, slightly soluble in water, easily soluble in organic solvents. It possesses a characteristic strong smell and a sharp burning taste. When pure, it is nontoxic, while the impure product is toxic. On passing its vapour through a red-hot tube, it decomposes with production of acetylene, ethylene, propylene, and other compounds. It is oxidized by chromic acid to isovaleraldehyde, and it forms crystalline addition compounds with calcium chloride and tin(IV) chloride.

The other amyl alcohols may be obtained synthetically. Of these, tertiary butyl carbinol has been the most difficult to obtain, its synthesis having first been reported in 1891, by L. Tissier ("Comptes Rendus", 1891, 112, p. 1065) by the reduction of a mixture of trimethyl acetic acid and trimethylacetyl chloride with sodium amalgam. It is a solid that melts at 48 to 50 °C and boils at 112.3 °C.

References

*1911

External links


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Look at other dictionaries:

  • Amyl alcohol — Am yl al co*hol (Org. Chem.) Any of eight isomeric liquid alcohols ({C5H11.OH}), transparent, colorless liquids. It is the hydroxide of amyl. Also called {amylic alcohol}. The amyl alcohol obtained from {fusel oil} is mostly isoamyl alcohol (3… …   The Collaborative International Dictionary of English

  • amyl alcohol — Alcohol Al co*hol ([a^]l k[ o]*h[o^]l), n. [Cf. F. alcool, formerly written alcohol, Sp. alcohol alcohol, antimony, galena, OSp. alcofol; all fr. Ar. al kohl a powder of antimony or galena, to paint the eyebrows with. The name was afterwards… …   The Collaborative International Dictionary of English

  • amyl alcohol — n any of eight isomeric alcohols C5H12O used esp. as solvents and in making esters also either of two commercially produced mixtures of amyl alcohols used esp. as solvents …   Medical dictionary

  • amyl alcohol — n. a colorless, sharp smelling alcohol, C5H11OH, obtained by the fermentation of starchy substances and also present in fusel oil: it has several isomeric forms …   English World dictionary

  • amyl alcohol — noun a mixture of 2 or more isomeric alcohols; used as a solvent and in organic synthesis • Hypernyms: ↑alcohol * * * noun 1. : pentyl alcohol 2. : either of two commercially produced mixtures of pentyl alcohols used chiefly in making esters and… …   Useful english dictionary

  • amyl alcohol — Chem. a colorless liquid, C5H12O, consisting of a mixture of two or more isomeric alcohols, derived from the pentanes, and used as a solvent and intermediate for organic synthesis: the main component of fusel oil. [1860 65] * * * ▪ chemical… …   Universalium

  • amyl alcohol — pentilo alkoholis statusas T sritis chemija formulė H(CH₂)₅OH atitikmenys: angl. amyl alcohol; pentyl alcohol rus. амиловый спирт; пентиловый спирт ryšiai: sinonimas – 1 pentanolis …   Chemijos terminų aiškinamasis žodynas

  • amyl alcohol — (Chemistry) colorless isomeric alcohol produced by combining two alcohol from the pentanes (used as a solvent and in organic synthesis) …   English contemporary dictionary

  • amyl alcohol — noun Date: 1863 any of eight isomeric alcohols C5H12O used especially as solvents and in making esters; also a commercially produced mixture of amyl alcohols used especially as a solvent …   New Collegiate Dictionary

  • amyl alcohol — noun Any of the isomers of pentanol, CHOH; the principal constituent of fusel oil. Syn: pentanol …   Wiktionary

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