Process for the production of furfural using a water immiscible organic solvent

Abstract

The disclosure relates to an efficient process for the production of a furan derivative from C5 and/or C6 sugars. The process utilizes a water immiscible organic solvent system comprising at least one alkyl phenol and at least one alkylated naphthalene.

What is claimed is: 
     
         1 . A process comprising:
 A) contacting an aqueous feedstock comprising one or more C 5  and/or C 6  sugars with an acid catalyst in the presence of a water-immiscible organic solvent at a temperature in the range of from 90° C. to 250° C. to form a furan derivative and a residual aqueous feedstock;   B) separating the residual aqueous feedstock from the water-immiscible organic solvent;   C) optionally, isolating the furan derivative from the water-immiscible organic solvent; and   D) optionally, removing residual water or impurities from the water-immiscible organic solvent;   wherein the water-immiscible organic solvent comprises a mixture of at least one alkyl phenol and at least one alkylated naphthalene.   
     
     
         2 . The process of  claim 1 , wherein the acid catalyst is a mineral acid, a heteropolyacid, an organic acid, a solid acid catalyst, carbon dioxide in water, or a combination thereof. 
     
     
         3 . The process of  claim 1 , wherein the at least one alkyl phenol is a compound represented by Structure (I): 
       
         
           
           
               
               
           
         
         wherein R is a C 1  to C 16  alkyl group; and 
         n is an integer from 1 to 5. 
       
     
     
         4 . The process of  claim 1 , wherein the at least one alkylated naphthalene is a compound represented by Structure (II): 
       
         
           
           
               
               
           
         
         wherein R 1  is a C 1  to C 6  alkyl group; 
         R 2  is a C 1  to C 6  alkyl group; 
         x is an integer from 1 to 4; and 
         y is an integer from 0 to 4. 
       
     
     
         5 . The process of  claim 1 , wherein the water-immiscible organic solvent consists essentially of at least one alkyl phenol and at least one alkylated naphthalene. 
     
     
         6 . The process of  claim 1 , wherein the furan derivative is furfural, 5-hydroxymethyl furfural, or a combination thereof. 
     
     
         7 . The process of  claim 1 , wherein the weight ratio of the at least one alkyl phenol to the at least one alkylated naphthalene is in the range of from 100:1 to 1:100. 
     
     
         8 . The process of  claim 1 , wherein the aqueous feedstock comprises C 5  sugars. 
     
     
         9 . The process of  claim 1 , wherein the aqueous feedstock comprises C 6  sugars. 
     
     
         10 . The process of  claim 1 , wherein the step of C) isolating the furan derivative from the water-immiscible organic solvent is a distillation step. 
     
     
         11 . The process of  claim 1 , wherein the step of C) isolating the furan derivative from the water-immiscible organic solvent is a flash evaporation step. 
     
     
         12 . A process comprising:
 A) contacting an aqueous feedstock comprising one or more C 5  and/or C 6  sugars with an acid catalyst in the presence of a water-immiscible organic solvent at a temperature in the range of from 90° C. to 250° C. to form a furan derivative and a residual aqueous feedstock;   B) separating the residual aqueous feedstock from the water-immiscible organic solvent;   C) optionally, isolating the furan derivative from the water-immiscible organic solvent; and   D) optionally, removing residual water or impurities from the water-immiscible organic solvent;   wherein the water-immiscible organic solvent comprises a mixture of at least one alkyl phenol and at least one hydrocarbon of carbon number 10 or higher.   
     
     
         13 . The process of  claim 12 , wherein the hydrocarbon is diesel. 
     
     
         14 . A composition comprising furfural or 5-hydroxymethyl furfural, at least one alkyl phenol, at least one alkylated naphthalene, and in the range of from 0 to 5% by weight of humins. 
     
     
         15 . The composition of  claim 14  consisting essentially of furfural or 5-hydroxymethyl furfural, at least one alkyl phenol, at least one alkylated naphthalene, and in the range of from 0 to 5% by weight of humins.