Method of producing coupled radical products

Abstract

A method that produces coupled radical products. The method involves obtaining a sodium salt of a carboxylic acid. 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) that separates an anolyte compartment housing the anolyte from a catholyte compartment housing a catholyte. The anolyte includes a first solvent or mixture of solvents and a quantity of the sodium salt of the carboxylic acid. 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.

1 . A method for producing a coupled radical product comprising:
 obtaining a sodium salt of a carboxylic acid;   preparing an anolyte for use in an electrolytic cell, the electrolytic cell comprising an anolyte compartment, a catholyte compartment, and a NaSICON membrane that separates the anolyte compartment from the catholyte compartment, wherein the anolyte is housed within the anolyte compartment and a catholyte is housed within the catholyte compartment, wherein the anolyte comprises a first solvent or mixture of solvents and a quantity of the sodium salt of the carboxylic acid; and   electrolyzing the anolyte within the cell, wherein the electrolyzing decarboxylates the sodium salt of the carboxylic acid and converts the sodium salt of the carboxylic acid into one or more alkyl radicals that react to form a coupled radical product.   
     
     
         2 . A method as in  claim 1 , wherein the sodium salt of a carboxylic acid is derived from at least one of carbohydrates, lipids, lignins, and mixtures of thereof. 
     
     
         3 . A method as in  claim 2 , wherein the coupled radical product comprises a hydrocarbon. 
     
     
         4 . A method as in  claim 1 , further comprising decarboxylating an alkali metal formate to form a hydrogen radical. 
     
     
         5 . A method as in  claim 1 , further comprising photolysing hydrogen gas to form a hydrogen radical. 
     
     
         6 . A method as in  claim 1 , wherein the sodium salt of the carboxylic acid comprises a quantity of sodium acetate that produces methyl radicals when the sodium salt of the carboxylic acid is decarboxylated, and wherein the methyl radicals couple to the alkyl radicals. 
     
     
         7 . A method as in  claim 1 , wherein the first mixture of solvents comprises at least one G-type solvent and at least one H-type solvent. 
     
     
         8 . A method as in  claim 7 , wherein the G-type solvent comprises a solvent chosen from ehthylene glycol, glycerine, 1,2-dihydroxy-4-oxadodecane, 2-methyl-2-propyl-1,3-propanediol, 2-ethyl-1,3-hexanediol, 2-amino-2-methyl-1,3-propanediol, 2,3-butanediol, 3-amino-1,2-propanediol, 1,2-octanediol, cis-1,2-cyclohexanediol, rans-1,2-cyclohexanediol, cis-1,2-cyclopentanediol, 1,2-pentanediol, and 1,2-hexanediol. 
     
     
         9 . A method as in  claim 7 , wherein the H-type solvent comprises a solvent chosen from isopropanol, methanol, ethanol, butanol, amyl alcohol, octanol, hexane, trichloroethane, dichloroethane, methylene, dichloride, chloroform, carbon tetrachloride, tetralin, decalin, monoglyme, diglyme, tetraglyme, acetone, and acetaldehyde. 
     
     
         10 . A method as in  claim 7 , wherein the H-type solvent comprises a product of the decarboxylation. 
     
     
         11 . 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. 
     
     
         12 . A method as in  claim 1 , wherein a reaction of the catholyte produces a base that may be used to form the alkali metal salt of the carboxylic acid via a saponification reaction. 
     
     
         13 . A method as in  claim 1 , wherein the alkali metal salt of the carboxylic acid is formed via a saponification reaction that occurs within the electrolytic cell. 
     
     
         14 . A method for producing a coupled radical product comprising:
 obtaining a sodium salt of a fatty acid by saponifying the fatty acid;   preparing an anolyte for use in an electrolytic cell, the electrolytic cell comprising an anolyte compartment, a catholyte compartment, and a NaSICON membrane that separates the anolyte compartment from the catholyte compartment, wherein the anolyte is housed within the anolyte compartment and a catholyte is housed within the catholyte compartment, wherein the anolyte comprises at least one G-type solvent and at least one H-type solvent and a quantity of the sodium salt of the fatty acid; and   electrolyzing the anolyte within the cell, wherein the electrolyzing decarboxylates the sodium salt of the fatty acid and converts the sodium salt of the fatty acid into one or more alkyl radicals that react to form a coupled radical product comprising a hydrocarbon.   
     
     
         15 . A method as in  claim 14 , further comprising decarboxylating an alkali metal formate to form a hydrogen radical. 
     
     
         16 . A method as in  claim 14 , further comprising photolysing hydrogen gas to form a hydrogen radical. 
     
     
         17 . A method as in  claim 14 , wherein the first mixture of solvents comprises at least one G-type solvent and at least one H-type solvent. 
     
     
         18 . A method as in  claim 17 , wherein the G-type solvent comprises a solvent chosen from ehthylene glycol, glycerine, 1,2-dihydroxy-4-oxadodecane, 2-methyl-2-propyl-1,3-propanediol, 2-ethyl-1,3-hexanediol, 2-amino-2-methyl-1,3-propanediol, 2,3-butanediol, 3-amino-1,2-propanediol, 1,2-octanediol, cis-1,2-cyclohexanediol, rans-1,2-cyclohexanediol, cis-1,2-cyclopentanediol, 1,2-pentanediol, and 1,2-hexanediol. 
     
     
         19 . A method as in  claim 14 , wherein the H-type solvent comprises a solvent chosen from isopropanol, methanol, ethanol, butanol, amyl alcohol, octanol, hexane, trichloroethane, dichloroethane, methylene, dichloride, chloroform, carbon tetrachloride, tetralin, decalin, monoglyme, diglyme, tetraglyme, acetone, and acetaldehyde. 
     
     
         20 . A method for producing a coupled radical product comprising:
 obtaining a sodium salt of a carboxylic acid, wherein the sodium salt of a carboxylic acid is derived from at least one of carbohydrates, lipids, lignins, and mixtures of thereof;   preparing an anolyte for use in an electrolytic cell, the electrolytic cell comprising an anolyte compartment, a catholyte compartment, and a NaSICON membrane that separates the anolyte compartment from the catholyte compartment, wherein the anolyte is housed within the anolyte compartment and a catholyte is housed within the catholyte compartment, wherein the anolyte comprises at least one G-type solvent, at least one H-type solvent and a quantity of the sodium salt of the carboxylic acid;   electrolyzing the anolyte within the cell, wherein the electrolyzing decarboxylates the sodium salt of the carboxylic acid and converts the sodium salt of the carboxylic acid into one or more alkyl radicals that react to form a coupled radical product; and   wherein the sodium salt of the carboxylic acid comprises a quantity of sodium acetate that produces methyl radicals when the sodium salt of the carboxylic acid is decarboxylated, and wherein the methyl radicals couple to the alkyl radicals.   
     
     
         21 . A method as in  claim 20 , wherein the G-type solvent comprises a solvent chosen from ehthylene glycol, glycerine, 1,2-dihydroxy-4-oxadodecane, 2-methyl-2-propyl-1,3-propanediol, 2-ethyl-1,3-hexanediol, 2-amino-2-methyl-1,3-propanediol, 2,3-butanediol, 3-amino-1,2-propanediol, 1,2-octanediol, cis-1,2-cyclohexanediol, rans-1,2-cyclohexanediol, cis-1,2-cyclopentanediol, 1,2-pentanediol, and 1,2-hexanediol. 
     
     
         22 . A method as in  claim 20 , wherein the H-type solvent comprises a solvent chosen from isopropanol, methanol, ethanol, butanol, amyl alcohol, octanol, hexane, trichloroethane, dichloroethane, methylene, dichloride, chloroform, carbon tetrachloride, tetralin, decalin, monoglyme, diglyme, tetraglyme, acetone, and acetaldehyde.