Method of producing coupled radical products

Abstract

A method that produces coupled radical products from biomass. The method involves obtaining a lipid or carboxylic acid material from the biomass. This material may be a carboxylic acid, an ester of a carboxylic acid, a triglyceride of a carboxylic acid, or a metal salt of a carboxylic acid, or any other fatty acid derivative. This lipid material or carboxylic acid material is converted into an alkali metal salt. The alkali metal salt is then used in an anolyte as part of an electrolytic cell. The electrolytic cell may include an alkali ion conducting membrane (such as a NaSICON membrane). When the cell is operated, the alkali metal salt of the carboxylic acid decarboxylates and forms radicals. Such radicals are then bonded to other radicals, thereby producing a coupled radical product such as a hydrocarbon. The produced hydrocarbon may be, for example, saturated, unsaturated, branched, or unbranched, depending upon the starting material.

1 . A method for producing a coupled radical product comprising:
 preparing an anolyte for use in an electrolytic cell, the electrolytic cell comprising an alkali ion conducting membrane, wherein the anolyte comprises a first solvent or mixture of solvents, a quantity of an alkali metal salt of a carboxylic acid, and a quantity of a supporting electrolyte comprising an alkali metal salt of a lower alkyl carboxylic acid; and   electrochemical decarboxylating the alkali metal salt of the carboxylic acid within the electrolytic cell, wherein the electrochemical decarboxylating converts the alkali metal salt of the carboxylic acid into alkyl radicals and converts the supporting electrolyte into a lower alkyl radical or to a hydrogen radical, wherein the alkyl radicals and the lower alkyl radical or hydrogen radical react to form a coupled radical product, wherein the alkali metal salt of the carboxylic acid is formed via a saponification reaction that occurs within the electrolytic cell.   
     
     
         2 . A method as in  claim 1 , wherein the coupled radical product comprises a mixture of different hydrocarbons. 
     
     
         3 . A method as in  claim 1 , wherein the electrochemical decarboxylating the alkali metal salt of the carboxylic acid occurs by electrolyzing the anolyte. 
     
     
         4 . A method as in  claim 1 , wherein the alkali metal comprises sodium such that the alkali metal salt of the carboxylic acid comprises a sodium salt of the carboxylic acid and wherein the alkali ion conducting membrane comprises a NaSICON membrane, wherein the membrane divides the cell into an anolyte compartment and a catholyte compartment, the anolyte being housed within the anolyte compartment and a catholyte being housed within the catholyte compartment. 
     
     
         5 . A method as in  claim 1 , wherein hydrogen radicals are formed by electrochemical decarboxylating an alkali metal formate during the electrochemical decarboxylating of the alkali salt of the carboxylic acid, and/or photolysis of hydrogen gas. 
     
     
         6 . A method as in  claim 1 , wherein the first solvent comprises a two-phase solvent system, wherein one phase is capable of dissolving ionic materials and the other phase is capable of dissolving non-ionic materials. 
     
     
         7 . A method as in  claim 1 , wherein the first solvent or first mixture of solvents comprises methanol. 
     
     
         8 . A method as in  claim 4 , wherein the catholyte comprises a second solvent or mixture of solvents, wherein the second solvent or mixture of solvents included in the catholyte and the first solvent or mixture of solvents included in the anolyte are different. 
     
     
         9 . A method as in  claim 4 , wherein an electrochemical reaction of the catholyte produces a base. 
     
     
         10 . A method as in  claim 1 , wherein the supporting electrolyte is an alkali metal salt of a lower alkyl carboxylic acid having from one to five carbon atoms.