Methods of making organic compounds by metathesis and hydrocyanation

Abstract

The invention is directed to methods of making organic compounds by metathesis and hydrocyanation. Hydrocyanation functions to introduce a nitrile group into the organic compound. The nitrile group may be converted into an amine group, an aldehyde group, an alcohol group, or a carboxylic acid group. The method of the invention may be used, for example, to make industrial important organic compounds such as diacids, diesters, acid-amines, acid-alcohols, acid-nitriles, ester-amines, ester-alcohols, and ester-nitriles.

1 - 55 . (canceled) 
     
     
         56 . A method for making an organic compound, the method comprising:
 (a) providing an unsaturated glyceride, wherein the unsaturated glyceride comprises up to three fatty acid moieties selected from the group consisting of monounsaturated fatty acids, polyunsaturated fatty acids, and saturated fatty acids, provided that the unsaturated glyceride comprises at least one unsaturated fatty acid moiety;   (b) reacting the unsaturated glyceride with a monohydric alcohol to form a monoester of the at least one unsaturated fatty acid of step (a);   (c) reacting the monoester of step (b) with an alpha olefin, an internal olefin, or a mixture thereof, in the presence of a metathesis catalyst to form a cross-metathesized unsaturated monoester; and   (d) hydrocyanating at least one carbon-carbon double bond of the cross-metathesized unsaturated monoester of step (c) to form a hydrocyanated monoester.   
     
     
         57 . The method of  claim 56 , further comprising hydrogenating the hydrocyanated monoester to form an aminated monoester. 
     
     
         58 . The method of  claim 56 , further comprising hydrolyzing the hydrocyanated monoester to form a hydrocyanated carboxylic acid. 
     
     
         59 . The method of  claim 56 , further comprising reducing the hydrocyanated monoester to form a formylated monoester. 
     
     
         60 . The method of  claim 56 , further comprising reducing the hydrocyanated monoester to form a hydroxylated monoester. 
     
     
         61 . The method of  claim 56 , wherein the at least one unsaturated fatty acid moiety is a delta-9 fatty acid moiety. 
     
     
         62 . The method of  claim 61 , wherein the at least one unsaturated fatty acid moiety is an oleic acid moiety, a linoleic acid moiety, or a linolenic acid moiety. 
     
     
         63 . The method of  claim 56 , wherein the monohydric alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, and butanol. 
     
     
         64 . The method of  claim 63 , wherein the monohydric alcohol is methanol. 
     
     
         65 . The method of  claim 56 , wherein step (c) comprises reacting the monoester of step (b) with an alpha olefin. 
     
     
         66 . The method of  claim 65 , wherein the alpha olefin is selected from the group consisting of: ethylene, 1-propene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, and 1-nonene. 
     
     
         67 . The method of  claim 56 , wherein step (c) comprises reacting the monoester of step (b) with an internal olefin. 
     
     
         68 . The method of  claim 67 , wherein the internal olefin is selected from the group consisting of: 2-butene, 3-hexene, 4-octene, 2-pentene, 2-hexene, 2-heptene, 3-heptene, 2-octene, 3-octene, 2-nonene, 3-nonene, and 4-nonene. 
     
     
         69 . The method of  claim 56 , wherein the cross-metathesized unsaturated monoester is a monoester of 9-decenoid acid, 9-undecenoid acid, or 9-dodecenoic acid. 
     
     
         70 . The method of  claim 56 , wherein the cross-metathesized unsaturated monoester is a monoester is an internally unsaturated monoester. 
     
     
         71 . The method of  claim 70 , wherein the internally unsaturated monoester is a monoester of 9-undecenoid acid or 9-dodecenoic acid. 
     
     
         72 . The method of  claim 70 , comprising isomerizing the internally unsaturated monoester to form a terminally unsaturated monoester. 
     
     
         73 . The method of  claim 71 , comprising isomerizing the internally unsaturated monoester to form a monoester of 10-undecenoic acid or 11-dodecenoic acid. 
     
     
         74 . The method of  claim 56 , wherein the unsaturated glyceride is derived from a natural oil. 
     
     
         75 . The method of  claim 74 , wherein the natural oil comprises plant-based oils, animal fats, algae oils, or combinations thereof.