Method of carbon chain extension using novel aldol reaction

Abstract

Method of producing C 8 -C 15 hydrocarbons. comprising providing a ketone starting material; providing an aldol starting material comprising chloromethylfurfural; mixing the ketone starting material and the aldol starting material in a reaction in the presence of a proline-containing catalyst selected from the group consisting of Zn(Pro) 2 , Yb(Pro) 3 , and combinations thereof, or a catalyst having one of the structures (I), (II) or (III), and in the presence of a solvent, wherein the solvent comprises water and is substantially free of organic solvents, where (I), (II) and (III) respectively are where R 1 is a C 1 -C 6 alkyl moiety, X=(OH) and n=2. In (III), X may be CH 2 , sulfur or selenium, M may be Zn, Mg, or a lanthanide, and R 1 and R 2 each independently may be a methyl, ethyl, phenyl moiety.

1 . A method of producing C 8 -C 15  hydrocarbons comprising:
 a) providing a ketone starting material;   b) providing an aldol starting material comprising chloromethylfurfural; and   c) mixing the ketone starting material and the aldol starting material in a reaction in the presence of a proline-containing catalyst selected from the group consisting of Zn(Pro) 2 , Yb(Pro) 2 , and combinations thereof, to produce the C 8 -C 15  hydrocarbons.   
     
     
         2 . The method of  claim 1 , wherein the ketone starting material comprises acetone, dihydroxyacetone, or combinations thereof. 
     
     
         3 . The method of  claim 1 , wherein the reaction occurs at about 25° C. 
     
     
         4 . (canceled) 
     
     
         5 . A method of producing C 8 -C 15  hydrocarbons comprising:
 a) providing a ketone starting material;   b) providing an aldol starting material; and   c) mixing the ketone starting material and the aldol starting material in a reaction in the presence of a catalyst having the structure:   
       
         
           
           
               
               
           
         
       
       to produce the C 8 -C 15  hydrocarbons. 
     
     
         6 . The method of  claim 5 , wherein the aldol starting material comprises chloromethylfurfural. 
     
     
         7 . The method of  claim 5 , wherein the ketone starting material comprises acetone, dihydroxyacetone, or combinations thereof. 
     
     
         8 . The method of  claim 5 , wherein the reaction occurs at about 25° C. 
     
     
         9 . (canceled) 
     
     
         10 . A method of producing C 8 -C 15  hydrocarbons comprising:
 a) providing a ketone starting material;   b) providing an aldol starting material; and   c) mixing the ketone starting material and the aldol starting material in a reaction in the presence of a catalyst having the structure:   
       
         
           
           
               
               
           
         
       
       wherein R 1  is a C 1 -C 6  alkyl moiety, X=(OH) and n=2, to produce the C 8 -C 15  hydrocarbons. 
     
     
         11 . The method of  claim 10 , wherein the aldol starting material comprises chloromethylfurfural. 
     
     
         12 . The method of  claim 10 , wherein the ketone starting material comprises acetone, dihydroxyacetone, or combinations thereof. 
     
     
         13 . The method of  claim 10 , wherein the reaction occurs at about 25° C. 
     
     
         14 . (canceled) 
     
     
         15 . A method of producing C 8 -C 15  hydrocarbons comprising:
 a) providing a ketone starting material;   b) providing an aldol starting material; and   c) mixing the ketone starting material and the aldol starting material in a reaction in the presence of a catalyst having the structure:   
       
         
           
           
               
               
           
         
       
       where X is CH 2 , sulfur or selenium, M is Zn, Mg, or a lanthanide, and R 1  and R 2  each independently are a methyl, ethyl, or phenyl moiety, to produce the C 8 -C 15  hydrocarbons. 
     
     
         16 . The method of  claim 15 , wherein the aldol starting material comprises chloromethylfurfural. 
     
     
         17 . The method of  claim 15 , wherein the ketone starting material comprises acetone, dihydroxyacetone, or combinations thereof. 
     
     
         18 . The method of  claim 15 , wherein the reaction occurs at about 25° C. 
     
     
         19 . (canceled) 
     
     
         20 . The method of  claim 1 , further comprising adding a solvent to the reaction, said solvent comprising water. 
     
     
         21 . The method of  claim 20 , wherein the solvent is substantially free of organic solvents. 
     
     
         22 . The method of  claim 20 , wherein the solvent further comprises a salt. 
     
     
         23 . The method of  claim 5 , further comprising adding a solvent to the reaction, said solvent comprising water. 
     
     
         24 . The method of  claim 23 , wherein the solvent is substantially free of organic solvents. 
     
     
         25 . The method of  claim 23 , wherein the solvent further comprises a salt. 
     
     
         26 . The method of  claim 10 , further comprising adding a solvent to the reaction, said solvent comprising water. 
     
     
         27 . The method of  claim 26 , wherein the solvent is substantially free of organic solvents. 
     
     
         28 . The method of  claim 26 , wherein the solvent further comprises a salt. 
     
     
         29 . The method of  claim 15 , further comprising adding a solvent to the reaction, said solvent comprising water. 
     
     
         30 . The method of  claim 29 , wherein the solvent is substantially free of organic solvents. 
     
     
         31 . The method of  claim 29 , wherein the solvent further comprises a salt.