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 composition comprising a first trihydroxy compound having the formula:
wherein:
R 1 is hydrogen and R 2 is a C 6 -C 30 linear alkyl; and a second trihydroxy compound having the formula:
wherein R 1 is a C 6 -C 30 linear alkyl and R 2 is hydrogen; and
X is:
2. The composition of claim 1 , wherein R 1 is hydrogen and R 2 is a C 6 -C 14 linear alkyl in the first trihydroxy compound, and R 1 is a C 6 -C 14 linear alkyl and R 2 is hydrogen in the second trihydroxy compound.
3. A method for preparing the composition of claim 1 , the method comprising:
(a) providing an epoxide compound of the formula
wherein R 3 is hydrogen or a C 6 -C 30 linear alkyl; and
(b) providing glycerol or a protected glycerol compound of the formula
wherein R 4 and R 5 are independently selected from the group consisting of hydrogen, linear alkyl, branched alkyl, cyclic alkyl, linear alkenyl, branched alkenyl, cyclic alkenyl, aryl, and alkaryl groups;
(c) reacting the compounds of a) and b) in the presence of an acid or base catalyst; and
(d) deprotecting the protected glycerol to provide the composition.
4. The method of claim 3 , wherein R 4 and R 5 are not both hydrogen.
5. The method of claim 3 , wherein R 1 is hydrogen and R 2 is a C 6 -C 14 linear alkyl in the first trihydroxy compound, and R 1 is a C 6 -C 14 linear alkyl and R 2 is hydrogen in the second trihydroxy compound.
6. The method of claim 3 , wherein 4 and R 5 are both methyl.