Extraction of natural ferulate and coumarate from biomass

Abstract

A process for a reactive separation of organic molecules from biomass includes a reaction step for the biomass, a simultaneous extraction step using a solvent, and a filtration step to recover products, wherein the products comprise ferulic acid and/or coumaric acid. The products are extracted from the biomass in a pressurized stirred batch reactor using a liquid extraction solvent and a base in which the ferulate and the coumarate remain.

What is claimed is: 
     
         1 . A process for a reactive separation of organic molecules from biomass comprising:
 contacting biomass with a base and a solvent;   extracting products from the biomass with the solvent based on a reaction of the base with the biomass to form a slurry;   filtering the slurry to recover a liquid product, wherein the liquid product comprises: a) a ferulate, a coumarate, ferulic acid, coumaric acid, or any combination thereof, and b) a fatty acid compound comprising a fatty acid, a fatty acid ester, or any combination thereof; and   removing at least a portion of the fatty acid compound from the liquid product to produce a purified liquid product comprising the coumarate, the ferulate, the ferulic acid, the coumaric acid, or any combination thereof.   
     
     
         2 . The process of  claim 1 , wherein removing at least the portion of the fatty acid compound from the liquid product comprises removing at least the portion of the fatty acid compound from the liquid product by a liquid-liquid extraction to produce the purified liquid product. 
     
     
         3 . The process of  claim 1 , wherein removing at least the portion of the fatty acid compound from the liquid product comprises removing the fatty acid compound from the liquid product by liquid chromatography to produce the purified liquid product comprising the coumarate, the ferulate, the ferulic acid, the coumaric acid, or any combination thereof. 
     
     
         4 . The process of  claim 1 , wherein removing at least the portion of the fatty acid compound from the liquid product comprises removing the fatty acid compound from the liquid product by ion exchange chromatography or size exclusion chromatography to produce the purified liquid product comprising the coumarate, the ferulate, the ferulic acid, the coumaric acid, or any combination thereof. 
     
     
         5 . The process of  claim 1 , wherein removing at least the portion of the fatty acid compound from the liquid product comprises removing the fatty acid compound from the liquid product as an insoluble impurity by dissolving the ferulic acid in an aqueous solution to form the insoluble impurity and removing the insoluble impurity by filtration or phase separation. 
     
     
         6 . The process of  claim 1 , wherein removing at least the portion of the fatty acid ester from the liquid product comprises hydrolyzing the liquid product under basic conditions to convert at least the portion of the fatty acid ester to a corresponding acid, wherein the liquid product comprises organic molecules, wherein the organic molecules comprise acidic esters, terpenoids, sterols, carbohydrates, and flavonoids. 
     
     
         7 . The process of  claim 6 , wherein hydrolyzing the liquid product under basic conditions comprises:
 combining the liquid product with an aqueous base solution to form a hydrolysis mixture;   heating the hydrolysis mixture; and   hydrolyzing any ferulates to ferulic acid in the hydrolysis mixture in response to the heating.   
     
     
         8 . The process of  claim 1 , further comprising:
 adding an acid to the liquid product after removing the fatty acid compound;   acidifying the liquid product in response to adding the acid to produce acidified products;   precipitating one or more byproducts from the acidified products; and   removing the one or more byproducts as solids from the acidified products, wherein a concentration of ferulic acid in the acidified products is greater after removing the one or more byproducts than prior to acidifying the products.   
     
     
         9 . The process of  claim 8 , further comprising:
 contacting the acidified products with an organic solvent after removing the one or more byproducts;   extracting the ferulic acid from the acidified products using the organic solvent to form a rich organic solvent;   removing the organic solvent from the rich organic solvent; and   producing a solid ferulic acid in response to removing the organic solvent from the rich organic solvent.   
     
     
         10 . The process of  claim 9 , further comprising:
 dissolving the solid ferulic acid in a heated aqueous solution to form dissolved ferulic acid;   filtering the dissolved ferulic acid;   removing one or more insoluble impurities from the dissolved ferulic acid using the filtering; and   cooling the dissolved ferulic acid after removing the one or more insoluble impurities to produce purified solid ferulic acid.   
     
     
         11 . The process of  claim 10 , further comprising:
 purifying the ferulic acid using liquid chromatography.   
     
     
         12 . The process of  claim 9 , further comprising:
 purifying the ferulic acid using liquid chromatography.   
     
     
         13 . The process of  claim 1 , wherein removing the fatty acid compound from the liquid product comprises:
 generating a rich organic phase and the purified liquid product, wherein the rich organic phase comprises the fatty acid compound and the solvent.   
     
     
         14 . The process of  claim 13 , further comprising:
 removing the solvent from the rich organic phase to produce an oil phase and the solvent, wherein the oil phase has a phosphorus content of less than 250 ppm by mass.   
     
     
         15 . The process of  claim 14 , wherein the oil phase has an oleic acid content of less than 3% by mass of the oil phase. 
     
     
         16 . The process of  claim 1 , wherein contacting the biomass with the base and the solvent occurs in the presence of water, wherein the water is present in a mass ratio of the water to the biomass of less than 15:1. 
     
     
         17 . The process of  claim 1 , wherein the liquid product is extracted from the biomass in a reactor comprising a pressurized stirred batch reactor or a stirred batch reactor, and wherein the reactor contains liquid and a gas consisting of nitrogen, argon, helium, or hydrogen, or their mixtures. 
     
     
         18 . The process of  claim 1 , wherein the solvent comprises 50-100% any aliphatic alcohols and 0-50% water, and wherein a mass ratio of the solvent to the biomass is in a range of 4:1 to 30:1. 
     
     
         19 . The process of  claim 1 , wherein the reaction step is carried out in a reactor, wherein the reactor is heated to a reaction temperature of between about 80-250° C., and wherein the reactor is held at the reaction temperature for 1-15 hours. 
     
     
         20 . The process of  claim 1 , wherein the solvent comprises 50-100% any aliphatic alcohols and 0-50% water.