Biofuels from oxidation products of oleic oil

Abstract

Methods for making biofuels, such as biokerosene, from various alcohols and nonanoic acid, a primary product of the ozonolysis of oleic acid. The products exhibit excellent low-temperature performance. Cloud points of the nonanoic esters range from −35 to −70° C. This super low-temperature performance shows the potential for replacing winter-season diesel, kerosene, and jet fuels. The products also show excellent oxidation stability and low greenhouse gas emissions. The energy densities of the products increase with the carbon atoms in the alcohols and are less than current biodiesel. The products generally have flash points higher than 90° C., indicating safer handling and storage. Compared to current biodiesel, the products have no issues with the cold soak filtration test.

What is claimed is: 
     
         1 . A method for making a biofuel, comprising:
 reacting nonanoic acid with one or more alcohols to esterify the nonanoic acid to form a fatty acid ester having a cloud point of −35° C. to −70° C.   
     
     
         2 . The method of  claim 1 , wherein the fatty acid ester has a flash point of 90° C. or more. 
     
     
         3 . The method of  claim 1 , wherein the nonanoic acid is an oxidation product of a high oleic oil. 
     
     
         4 . The method of  claim 1 , further comprising oxidizing a high oleic oil using ozonolysis to produce the nonanoic acid. 
     
     
         5 . The method of  claim 1 , wherein the alcohol is derived from a syngas. 
     
     
         6 . The method of  claim 1 , wherein the one or more alcohols comprise a n-alcohol having 1 to 12 carbon atoms. 
     
     
         7 . The method of  claim 1 , wherein the one or more alcohols comprise a n-alcohol having 1 to 6 carbon atoms. 
     
     
         8 . The method of  claim 1 , wherein the one or more alcohols comprise an iso-alcohol having 1 to 12 carbon atoms. 
     
     
         9 . The method of  claim 1 , wherein the one or more alcohols comprise an iso-alcohol having 1 to 6 carbon atoms. 
     
     
         10 . A method for making a biofuel, comprising:
 oxidizing oleic oil to produce nonanoic acid; and   esterifying the nonanoic acid with one or more alcohols having 1 to 12 carbon atoms to form a fatty acid ester having a cloud point of −35° C. to −70° C. and a flash point of at least 90° C.   
     
     
         11 . The method of  claim 10 , therein the one or more alcohols are linear alcohols. 
     
     
         12 . The method of  claim 10 , therein the one or more alcohols are iso-alcohols.