# US 11,078,149 B2 · Preparation and separation of a di-carboxylic acid-containing mixture > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,078,149 B2 - Document ID: US11078149B2 - Status: Granted - Kind: B2 - Application number: 16/849,471 - Filed: 2020-04-15 - Published: 2020-10-01 - Granted: 2021-08-03 - Earliest claimed: 2014-09-29 - Assignees: Archer Daniels Midland Company - Applicants: Archer-Daniels-Midland Company - Inventors: Gary M. Diamond; Eric L. Dias; Raymond Archer; Vincent J. Murphy; Thomas R. Boussie - Web page: https://patentgrep.com/patent/US11078149B2 ## CPC - C07C 51/47: by solid-liquid treatment; by chemisorption - B01D 15/1821: {Simulated moving beds} - B01D 15/363: {Anion-exchange} - C07C 51/16: by oxidation (C07C51/145 takes precedence) - C07C 51/23: of oxygen-containing groups to carboxyl groups - C07C 51/27: with oxides of nitrogen or nitrogen-containing mineral acids - C07C 59/285: Polyhydroxy dicarboxylic acids having five or more carbon atoms, e.g. saccharic acids - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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) ## Abstract Processes for separating a di-carboxylic acid or salt thereof from a mixture containing the di-carboxylic acid or salt thereof and one or more other components are provided. Also separation media useful for these separation processes is provided. In particular, processes for preparing an aldaric acid are described, such as glucaric acid from glucose, which includes separating the aldaric acid from the reaction product. Also, various glucaric acid products are described. ## Claims ### Claim 1 A mixture comprising a glucaric acid product and a separation media comprising an anion exchange chromatography resin in contact with the glucaric acid product, wherein the glucaric acid product comprises: from about 20 wt. % to about 65 wt. % glucaric acid or a salt thereof, from about 25 wt. % to about 70 wt. % gluconic acid or a salt thereof, less than about 10 wt. % of one or more ketogluconic acids or salts thereof, less than about 5 wt. % of one or more C2-C5 di-acids or salts thereof, and less than about 5 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product; and wherein the anion exchange chromatography resin is in di-carboxylate form. ### Claim 2 A mixture comprising a glucaric acid product and a separation media comprising an anion exchange chromatography resin in contact with the glucaric acid product, wherein the glucaric acid product comprises: from about 20 wt. % to about 65 wt. % glucaric acid or a salt thereof, from about 25 wt. % to about 70 wt. % gluconic acid or a salt thereof, from about 1 wt. % to about 20 wt. % guluronic acid or a salt thereof, less than about 10 wt. % of one or more ketogluconic acids or salts thereof, less than about 5 wt. % of one or more C2-C5 di-acids or salts thereof, and less than about 5 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product; and wherein the anion exchange chromatography resin comprises a weakly basic anion exchange chromatography resin. ### Claim 3 (depends on 2) The mixture of claim 2 wherein the anion exchange chromatography resin comprises from about 60% to about 100% weak base functionality. ### Claim 4 (depends on 1) The mixture of claim 1 wherein the anion exchange chromatography resin is in glucarate form. ### Claim 5 (depends on 1) The mixture of claim 1 further comprising from about 1 wt. % to about 20 wt. % guluronic acid or a salt thereof based on the dissolved solids content. ### Claim 6 (depends on 1) The mixture of claim 1 wherein the concentration of glucaric acid or a salt thereof is from about 25 wt. % to about 65 wt. % of the dissolved solids contents. ### Claim 7 (depends on 1) The mixture of claim 1 wherein the concentration of gluconic acid or a salt thereof is from about 25 wt. % to about 65 wt. % of the dissolved solids contents. ### Claim 8 (depends on 1) The mixture of claim 1 wherein the concentration of the ketogluconic acids or salts thereof is from about of 1 wt. % to about 5 wt. % of the dissolved solids contents. ### Claim 9 (depends on 1) The mixture of claim 1 wherein the ketogluconic acids are 2-ketogluconic acid, 3-ketogluconic acid, 4-ketogluconic acid, and 5-ketogluconic acid. ### Claim 10 (depends on 1) The mixture of claim 1 wherein the concentration of the C2-C5 di-acids or salts thereof is from about 1 wt. % to less than about 5 wt. % of the dissolved solids contents. ### Claim 11 (depends on 1) The mixture of claim 1 wherein the glucose concentration is from about 0.001 wt. % to about 2.5 wt. % of the dissolved solids contents. ### Claim 12 (depends on 1) The mixture of claim 1 wherein the C2-C5 di-acids comprise xylaric acid, tartaric acid, tartronic acid, and oxalic acid. ### Claim 13 (depends on 1) The mixture of claim 1 further comprising from about 0.01 wt. % to about 1 wt. % glucuronic acid or a salt thereof based on the dissolved solids content. ### Claim 14 (depends on 1) The mixture of claim 1 wherein the glucaric acid product comprises: from about 30 wt. % to about 50 wt. % glucaric acid, from about 25 wt. % to about 45 wt. % gluconic acid, from about 5 wt. % to about 15 wt. % guluronic acid, less than about 2 wt. % of glucuronic acid, less than about 6 wt. % of one or more ketogluconic acids, less than about 5 wt. % of one or more C2-C5 di-acids, and less than about 2 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product. ### Claim 15 (depends on 1) The mixture of claim 1 wherein the glucaric acid product has a metal content of less than about 1 wt. % and contains less than about 0.1 wt. % of nitric acid and salts thereof based on the total weight of the glucaric acid product. ### Claim 16 (depends on 2) The mixture of claim 2 wherein the concentration of the ketogluconic acids or salts thereof is from about of 1 wt. % to about 5 wt. % of the dissolved solids contents. ### Claim 17 (depends on 2) The mixture of claim 2 wherein the ketogluconic acids are 2-ketogluconic acid, 3-ketogluconic acid, 4-ketogluconic acid, and 5-ketogluconic acid. ### Claim 18 (depends on 2) The mixture of claim 2 wherein the concentration of the C2-C5 di-acids or salts thereof is from about 1 wt. % to less than about 5 wt. % of the dissolved solids contents. ### Claim 19 (depends on 2) The mixture of claim 2 wherein the C2-C5 di-acids comprise xylaric acid, tartaric acid, tartronic acid, and oxalic acid. ### Claim 20 (depends on 2) The mixture of claim 2 further comprising from about 0.01 wt. % to about 1 wt. % glucuronic acid or a salt thereof based on the dissolved solids content. ### Claim 21 (depends on 2) The mixture of claim 2 wherein the glucaric acid product comprises: from about 30 wt. % to about 50 wt. % glucaric acid, from about 25 wt. % to about 45 wt. % gluconic acid, from about 5 wt. % to about 15 wt. % guluronic acid, less than about 2 wt. % of glucuronic acid, less than about 6 wt. % of one or more ketogluconic acids, less than about 5 wt. % of one or more C2-C5 di-acids, and less than about 2 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product.