Surface active agents derived from biodiesel-based alkylated aromatic compounds
View Patent ↗A surface active agent comprising an arylated methyl ester of a fatty acid, or mixture of fatty acids, derived from biodiesel or a triglyceride source is disclosed. The fatty acid mixture is condensed to methyl esters and alkylated with aromatic substituents under Friedel-Crafts conditions. The alkylated methyl esters may be alkoxylated using a catalyst derived from fatty acids, alkaline earth salts, and strong acids. The resulting nonionic surfactant may also be sulfonated to produce one class of anionic surfactants. The alkylated methyl esters may also be directly sulfonated to produce another class of anionic surfactants.
1. A method of making a chemical composition, comprising:
forming an unsaturated fatty acid methyl ester composition by subjecting an unsaturated fatty acid to an esterification process;
forming an aromatic alkylate from the unsaturated fatty acid methyl ester composition by performing an aromatic alkylation process on the unsaturated fatty acid methyl ester composition; and
ethoxylating the aromatic alkylate.
2. The method of claim 1 , wherein forming the aromatic alkylate comprises reacting the unsaturated fatty acid methyl ester composition with benzene in the presence of an ionic liquid catalyst.
3. The method of claim 1 , wherein ethoxylating the aromatic alkylate comprises contacting the aromatic alkylate with an ethylene oxide in the presence of a catalyst derived from a fatty acid, an alkaline earth salt, and a strong acid.
4. The method of claim 3 , wherein the catalyst is further derived from a glycol.
5. The method of claim 1 , further comprising sulfonating the ethoxylated aromatic alkylate.
6. The method of claim 5 , wherein sulfonating the ethoxylated aromatic alkylate comprises contacting the ethoxylated aromatic alkylate with a sulfonic acid.
7. The method of claim 1 , wherein the unsaturated fatty acid is obtained from at least one of (a) a triglyceride source selected from the group consisting of yellow grease, tallow, lard, vegetable oil, fish oil, algae oil, and combinations thereof, and (b) a biodiesel source.
8. The method of claim 7 , wherein the unsaturated fatty acid is obtained from a vegetable oil.
9. The method of claim 7 , wherein the biodiesel source comprises biodiesel derived from palm oil or canola oil.
10. The method of claim 1 , wherein the unsaturated fatty acid is produced by dehydrogenating at least one of a saturated fatty acid, triglyceride, and fatty acid methyl ester using a conventional dehydrogenation catalyst.