Provided herein are compounds of the formula: ##STR00001##
in which n is an integer equal to or greater than 1; R.sub.2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R.sub.1, R.sub.3, and R.sub.4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein compositions comprising the compounds are characterized by particular combinations of values for estolide number, kinematic viscosity, and pour point. Also provided are compositions containing the compounds and methods of making both the compounds and compositions thereof.

Disclosed is a method of producing an estolide, including a) converting biomass-derived oil into a fatty acid mixture, b) separating the fatty acid mixture into a C16 saturated fatty acid and a C18 unsaturated fatty acid, c) converting the C16 saturated fatty acid into a C15 or C16 linear internal olefin, d) subjecting the C15 or C16 linear internal olefin to an estolide reaction using a linking agent, thus obtaining an estolide A, e) subjecting the C18 unsaturated fatty acid to partial hydrogenating to increase the amount of oleic acid, and f) subjecting the oleic acid to an estolide reaction using a linking agent and then esterification, thus obtaining an estolide B.

Provided herein are estolide compositions having high oxidative stability, said compositions comprising at least one compound of formula:

##STR00001##

in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 1; R.sub.1, independently for each occurrence, is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R.sub.2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R.sub.3 and R.sub.4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Also provided herein are uses for the compositions and methods of preparing the same.

Provided herein are estolide base oils and oligomeric compounds prepared from processes that include cross metathesis. Exemplary processes include the preparation of terminally-unsaturated fatty acids by cross metathesis, and the subsequent oligomerization of terminally-unsaturated fatty acids to provide estolide compounds, such as the process set forth below:

##STR00001##

One aspect of the present invention is a refrigerating machine oil containing: a base oil; and a partial ester of a carboxylic acid and a polyhydric alcohol, wherein the carboxylic acid contains an unsaturated carboxylic acid.