# US 2022/0033341 A1 · Extraction of natural ferulate and coumarate from biomass > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2022/0033341 A1 - Document ID: US20220033341A1 - Status: Published application - Kind: A1 - Application number: 17/481,563 - Filed: 2021-09-22 - Published: 2022-02-03 - Earliest claimed: 2017-04-20 - Assignees: Spero Renewables, LLC - Applicants: Spero Renewables, LLC - Inventors: Mahdi M. ABU-OMAR; Daniel H. COLLER; Ian M. KLEIN - Web page: https://patentgrep.com/patent/US20220033341A1 ## CPC - C07C 67/56: by solid-liquid treatment; by chemisorption - C11B 3/00: Refining fats or fatty oils - B01D 11/028: {Flow sheets} - B01D 11/0284: {Multistage extraction} - B01D 11/0288: {Applications, solvents} - B01D 11/0292: {Treatment of the solvent} - C07C 51/09: from carboxylic acid esters or lactones - C07C 51/43: by change of the physical state, e.g. crystallisation - C07C 51/47: by solid-liquid treatment; by chemisorption - C07C 51/48: by liquid-liquid treatment - C07C 51/487: by treatment giving rise to chemical modification (by chemisorption C07C51/47) - C07C 67/00: Preparation of carboxylic acid esters - C07C 67/58: by liquid-liquid treatment - C11B 1/04: of vegetable raw material {(C11B1/025 takes precedence)} - C11B 1/10: by extracting - C11B 11/00: Recovery or refining of other fatty substances, e.g. lanolin or waxes - B01D 11/0219: {Fixed bed of solid material} - B01D 11/0257: {using mixing mechanisms, e.g. stirrers, jets (B01D11/0242 takes precedence)} - Y02W 30/74: Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F) - B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28) - Y02W: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT ## 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. ## Claims ### Claim 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. ### Claim 2 (depends on 1) 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. ### Claim 3 (depends on 1) 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. ### Claim 4 (depends on 1) 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. ### Claim 5 (depends on 1) 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. ### Claim 6 (depends on 1) 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. ### Claim 7 (depends on 6) 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. ### Claim 8 (depends on 1) 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. ### Claim 9 (depends on 8) 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. ### Claim 10 (depends on 9) 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. ### Claim 11 (depends on 10) The process of claim 10, further comprising: purifying the ferulic acid using liquid chromatography. ### Claim 12 (depends on 9) The process of claim 9, further comprising: purifying the ferulic acid using liquid chromatography. ### Claim 13 (depends on 1) 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. ### Claim 14 (depends on 13) 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. ### Claim 15 (depends on 14) The process of claim 14, wherein the oil phase has an oleic acid content of less than 3% by mass of the oil phase. ### Claim 16 (depends on 1) 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. ### Claim 17 (depends on 1) 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. ### Claim 18 (depends on 1) 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. ### Claim 19 (depends on 1) 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. ### Claim 20 (depends on 1) The process of claim 1, wherein the solvent comprises 50-100% any aliphatic alcohols and 0-50% water.