Glyceryl ether compounds and their use
Glyceryl ether compounds prepared by the reaction of glycerol and olefin epoxides are disclosed. The compounds are renewable biomass-based surfactants useful as detergents and emulsifiers in formulations for cleaning, laundry, personal care, cosmetics, and industrial uses.
1. A compound having the formula:
wherein:
Y is selected from the group consisting of:
wherein:
one of A or B is hydrogen and the other is selected from the group consisting of carboxyl, carboxylate salt, and ester; and
m and n are independently integers from 0 to 20, wherein the sum of m+n is in the range from 8 to 21.
2. A method for preparing a compound of claim 1 , wherein the method comprises:
a) providing a glycerol or a compound of the formula:
wherein:
R 4 and R 5 are independently selected from the group consisting of hydrogen; linear, branched, or cyclic alkyl; linear, branched, or cyclic alkenyl; aryl; and arylalkyl;
b) providing a compound selected from the group consisting of: an epoxidized triglyceride, and an epoxidized unsaturated fatty acid ester, wherein the fatty acid fragment has from 8 to 24 carbon atoms, and the alcohol fragment is a fragment of a C 1 -C 12 linear or branched monohydric alcohol;
c) effecting a reaction between the compounds of a) and b) in the presence of an acid or base catalyst; and
d) deprotecting the ketal or acetal group.
3. The method of claim 2 , wherein the method further comprises:
e) converting the carboxyl ester group to a free carboxyl group, a carboxylic salt, or an amide.