amyl alcohol

Amyl alcohol is an organic compound with the formula C₅H₁₂O. All eight isomers of amyl alcohol are known:

Isomers of amyl alcohol

Common Name	Structure	Type	IUPAC Name	Boiling Point (°C)[1]
normal amyl alcohol		primary	1-pentanol	138.5
isobutyl carbinol or isoamyl alcohol or isopentyl alcohol		primary	3-methyl-1-butanol	131.2
active amyl alcohol		primary	2-methyl-1-butanol	128.7
tertiary butyl carbinol or neopentyl alcohol		primary	2,2-dimethyl-1-propanol	113.1
diethyl carbinol		secondary	3-pentanol	115.3
methyl (n) propyl carbinol		secondary	2-pentanol	118.8
methyl isopropyl carbinol		secondary	3-methyl-2-butanol	113.6
dimethyl ethyl carbinol or tertiary amyl alcohol		tertiary	2-methyl-2-butanol	102

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.^[why?] 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

• This article incorporates text from the article "Amyl Alcohols" in the Encyclopædia Britannica, Eleventh Edition, a publication now in the public domain.