# US 10,308,991 B2 · Method of separating saccharides from aqueous product solution of cellulose hydrolysis process > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,308,991 B2 - Document ID: US10308991B2 - Status: Granted - Kind: B2 - Application number: 15/392,632 - Filed: 2016-12-28 - Published: 2017-12-14 - Granted: 2019-06-04 - Earliest claimed: 2016-06-13 - Assignees: Green Cellulosity Corporation - Applicants: Green Cellulosity Corporation - Inventors: Ruey-Fu Shih; Cheng-Hao Liu; Chiang-Hsiung Tong; Hom-Ti Lee - Web page: https://patentgrep.com/patent/US10308991B2 ## CPC - C13K 1/04: Purifying - C13K: SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES (chemically synthesised sugars or sugar derivatives C07H; polysaccharides, e.g. starch, derivatives thereof C08B; malt C12C; fermentation or enzyme-using processes for preparing compounds containing saccharide radicals C12P19/00; production of sucrose C13B) ## Abstract A method of separating a saccharide from an aqueous product solution of the cellulose hydrolysis process is provided. The aqueous product solution comprises a saccharide and a cellulose swelling agent. The cellulose swelling agent is zinc chloride, magnesium chloride or a combination thereof. The method comprises the following steps in the given order: (a) adding a first tertiary amine and an optional first organic solvent to the aqueous product solution to provide a mixture; (b) performing a solid-liquid separation to obtain a solution from the mixture; and (c) performing a liquid-liquid extraction by adding a second tertiary amine and a second organic solvent to the solution, and then removing the organic phase and collecting the aqueous phase, wherein the first tertiary amine and the second tertiary amine are the same or different, and the first organic solvent and the second organic solvent are the same or different. ## Claims ### Claim 1 A method of separating a saccharide from an aqueous product solution of cellulose hydrolysis process, wherein the aqueous product solution comprises a saccharide and a cellulose swelling agent, and the cellulose swelling agent is zinc chloride, magnesium chloride or a combination thereof, and the method comprises the following steps in the given order: (a) adding a first tertiary amine and an optional first organic solvent to the aqueous product solution to provide a mixture; (b) performing a solid-liquid separation to obtain a solution from the mixture; and (c) performing a liquid-liquid extraction by adding a second tertiary amine and a second organic solvent to the solution to obtain an organic phase and an aqueous phase, and then removing the organic phase and collecting the aqueous phase, wherein the first tertiary amine and the second tertiary amine are the same or different, and the first organic solvent and the second organic solvent are the same or different, wherein the first tertiary amine and the second tertiary amine are independently represented by a formula of NR1R2R3, wherein each of R1, R2, and R3 is independently C4-C10 alkyl. ### Claim 2 (depends on 1) The method according to claim 1, wherein the first tertiary amine and the second tertiary amine are independently selected from the group consisting of N-methyldicyclohexylamine, tributylamine, tripentylamine, tri-n-octylamine, tri-isooctylamine, and combinations thereof. ### Claim 3 (depends on 2) The method according to claim 2, wherein in the step (a), the amount of the first organic solvent is 0 to 3.5 parts by weight per part by weight of the first tertiary amine. ### Claim 4 (depends on 2) The method according to claim 2, wherein in the step (c), the amount of the second tertiary amine is 0.1 to 10 parts by weight per part by weight of the second organic solvent. ### Claim 5 (depends on 2) The method according to claim 2, which further comprises at least one of the following steps: (d) heating the organic phase removed in the step (c) to recycle the first tertiary amine and the second tertiary amine and obtain hydrochloride; and (e) washing a solid fraction separated in the step (b) with water, and mixing the washed solid fraction with an aqueous solution of hydrochloride to recycle the cellulose swelling agent. ### Claim 6 (depends on 2) The method according to claim 2, which further comprises a step of removing the organic phase from the mixture before the step (b), or a step of removing the organic phase from the solution before the step (c). ### Claim 7 (depends on 1) The method according to claim 1, wherein the first organic solvent and the second organic solvent are independently selected from the group consisting of primary alcohols, ketones, C6 or heavier alkanes, chloroalkanes, benzene and its derivatives, and combinations thereof. ### Claim 8 (depends on 1) The method according to claim 1, wherein the first organic solvent and the second organic solvent are independently a primary alcohol selected from the group consisting of n-butanol, n-pentanol, n-hexanol, cyclohexanol, n-heptanol, n-octanol, the isomers thereof, and combinations thereof. ### Claim 9 (depends on 1) The method according to Claim 1, wherein the first organic solvent and the second organic solvent are independently a ketone selected from the group consisting of butanone, pentanone, hexanone, cyclohexanone, the isomers thereof, and combinations thereof. ### Claim 10 (depends on 1) The method according to Claim 1, wherein the first organic solvent and the second organic solvent are independently selected from the group consisting of chloromethane, dichloromethane, trichloromethane, 1, 1-dichloroethane, 1 ,2-dichloroethane, and combinations thereof. ### Claim 11 (depends on 1) The method according to claim 1, wherein in the step (a), the amount of the first organic solvent is 0 to 3.5 parts by weight per part by weight of the first tertiary amine. ### Claim 12 (depends on 1) The method according to claim 1, wherein in the step (c), the amount of the second tertiary amine is 0.1 to 10 parts by weight per part by weight of the second organic solvent. ### Claim 13 (depends on 1) The method according to claim 1, which further comprises at least one of the following steps: (d) heating the organic phase removed in the step (c) to recycle the first tertiary amine and the second tertiary amine and obtain hydrochloride; and (e) washing a solid fraction separated in the step (b) with water, and mixing the washed solid fraction with an aqueous solution of hydrochloride to recycle the cellulose swelling agent. ### Claim 14 (depends on 13) The method according to claim 13, which further comprises a step of removing the organic phase from the mixture before the step (b), or a step of removing the organic phase from the solution before the step (c). ### Claim 15 (depends on 1) The method according to claim 1, which further comprises a step of removing the organic phase from the mixture before the step (b), or a step of removing the organic phase from the solution before the step (c).