Sperm Oil Replacements from Selectively Hydrogenated Soybean and Linseed Esters: Special Lubricants

Soybean and linseed oils were selectively hydrogenated with copper-on-silica gel catalyst. The linolenate content of the oils was reduced to diene and monoene with no appreciable increase in saturates. Hydrogenated soybean oils contained 68-76% monoene, 11-18% diene, 0% conjugated diene and triene, 1-6% conjugatable diene, 0-0.3% conjugatable triene, and 23-40% isolated trans double bonds. Hydrogenated linseed oils contained 44-54% monoene, 35-45% diene, 0% conjugated diene and triene, 0-7% conjugatable diene, 0-02% conjugatable triene, and 44-59% isoalted trans double bonds. Esters of fatty acids, derived from these selectively hydrogenated oils, were prepared with trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol, ethylene glycol, C18 saturated cyclic alcohols, primary C12-C18 saturated (nC l 2, nC14, nC16, nC18) alcohol, and primary C16-C18 saturated (nC16, nC18) alcohol blends. Measurements of viscosities and of smoke, flash, and fire points indicate that these esters are possible replacements for sperm oil. Certain of them, after sulfurization, also have potential as extreme pressure lubricant additives.