6831. Oleyl Alcohol

Nomenclature

CAS number: 143-28-2
(9Z)-9-Octadecen-1-ol; cis-9-octadecen-1-ol; Ocenol.
C18H36O; mol wt 268.48.
C 80.52%, H 13.52%, O 5.96%.

Description and references

Found in fish oils. Usually obtained as a mixture of C16 and C18 unsaturated alcohols with C18 predominating. Prepd from butyl oleate by a Bouveault-Blanc reduction with sodium and butyl alcohol; or from triolein by hydrogenation in the presence of zinc chromite: Noller, Bannerot, J. Am. Chem. Soc. 56, 1563 (1934); Reid et al., Org. Synth. 15, 72 (1935); Adkins, Gillespie, ibid. coll. vol. III, 671 (1955). Purification by fractional crystallization at -40° from acetone, followed by distillation: Swern et al., Oil Soap (Chicago) 21, 113 (1944); Loev, Dawson, J. Am. Chem. Soc. 78, 1182 (1956).

Chemical structure

Properties

Oily liquid. Usually pale yellow. Gives off acrid fumes when heated. d420 0.850. mp 13-19°. bp8 195°. bp1.5 182-184°. (Distilling range at 760 mm: 305-370°.) nD27.5 1.4582. Insol in water; sol in alcohol, ether.

Use

Chiefly in the manuf of its sulfuric esters which are detergents and wetting agents, as an antifoam agent; metal cutting lubricant; in carbon paper, stencil paper, printing ink; as a plasticizer; for softening and lubricating textile fabrics; carrier for medicaments.