# US 8,785,683 B2 · Production of glutaric acid and derivatives from carbohydrate-containing materials > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,785,683 B2 - Document ID: US8785683B2 - Status: Granted - Kind: B2 - Application number: 12/814,216 - Filed: 2010-06-11 - Published: 2010-12-16 - Granted: 2014-07-22 - Earliest claimed: 2009-06-13 - Assignees: Rennovia Inc. - Applicants: Thomas R. Boussie; Eric L. Dias; Zachary M. Fresco; Vincent J. Murphy - Inventors: Thomas R. Boussie; Eric L. Dias; Zachary M. Fresco; Vincent J. Murphy - Web page: https://patentgrep.com/patent/US8785683B2 ## CPC - C07C 51/313: {with molecular oxygen} - C07C 29/149: with hydrogen or hydrogen-containing gases - C07C 51/377: by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)} - C07C 209/00: Preparation of compounds containing amino groups bound to a carbon skeleton - C07C 253/00: Preparation of carboxylic acid nitriles (of cyanogen or compounds thereof C01C3/00) - C08G 63/16: Dicarboxylic acids and dihydroxy compounds - C08G 69/14: Lactams - C08G 69/26: derived from polyamines and polycarboxylic acids - C08G 69/36: derived from amino acids, polyamines and polycarboxylic acids - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract The present invention generally relates to processes for the chemocatalytic conversion of a pentose source to a glutaric acid product. The present invention includes processes for the conversion of pentose to a glutaric acid product via pentaric acid or derivatives thereof. The present invention also includes processes comprising the catalytic oxidation of pentose to pentaric acid and catalytic hydrodeoxygenation of pentaric acid or derivatives thereof to a glutaric acid product. ## Claims ### Claim 1 A process for preparing a glutaric acid product, the process comprising: reacting, in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support and a halogen source, a C5-backbone substrate and hydrogen to convert at least a portion of the C5-backbone substrate to a glutaric acid product, wherein the C5-backbone substrate comprises a compound of formula I wherein X is independently hydroxyl, oxo, halo, acyloxy or hydrogen provided that at least one X is not hydrogen and R1 is independently a salt-forming ion, hydrogen, hydrocarbyl, substituted hydrocarbyl, or lactone thereof and the glutaric acid product comprises a compound of formula II wherein R1 is as defined for formula I. ### Claim 2 (depends on 1) The process as set forth in claim 1 wherein the C5-backbone substrate comprises a compound of formula I, wherein X is hydroxyl and R1 is independently a salt-forming ion, hydrogen, hydrocarbyl, or substituted hydrocarbyl. ### Claim 3 (depends on 1) The process as set forth in claim 1 wherein the C5-backbone substrate comprises a pentaric acid. ### Claim 4 (depends on 1) The process as set forth in claim 1 wherein the C5-backbone substrate comprises a chemical selected from the group consisting of xylaric acid, arabinaric acid, derivatives of such acids, and mixtures thereof. ### Claim 5 (depends on 3) The process as set forth in claim 3 wherein the pentaric acid comprises an acid selected from the group consisting of xylaric and arabinaric acid. ### Claim 6 (depends on 4) The process as set forth in claim 4 wherein at least a portion of the C5-backbone substrate is solubilized with a weak carboxylic acid. ### Claim 7 (depends on 6) The process as set forth in claim 6 wherein the weak carboxylic acid is acetic acid. ### Claim 8 (depends on 1) The process as set forth in claim 1 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof. ### Claim 9 (depends on 1) The process as set forth in claim 1 wherein the hydrodeoxygenation catalyst comprises a first metal and a second metal, wherein the first metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof, and the second metal is selected from the group consisting of Mo, Ru, Rh, Pd, Ir, Pt, and Au, and wherein the second metal is not the same as the first metal. ### Claim 10 (depends on 1) The process as set forth in claim 1 wherein the hydrodeoxygenation catalyst support comprises a material selected from the group consisting of carbon, silica and zirconia. ### Claim 11 (depends on 6) The process as set forth in claim 6 wherein the halogen source comprises ionic, atomic, and/or molecular forms of bromine or iodine. ### Claim 12 (depends on 4) The process as set forth in claim 4 wherein the halogen source comprises hydrogen bromide. ### Claim 13 (depends on 1) The process as set forth in claim 1 wherein the molar ratio of the halogen source to C5-backbone substrate is equal to or less than about 1. ### Claim 14 (depends on 5) The process as set forth in claim 5 wherein the reaction is maintained at a temperature of at least about 80° C. ### Claim 15 (depends on 4) The process as set forth in claim 4 wherein the temperature of the reaction is from about 100° C. to about 200° C. ### Claim 16 (depends on 15) The process as set forth in claim 15 wherein the reaction is conducted under a partial pressure of hydrogen ranging from about 25 psia (172 kPa) to about 2500 psia (17237 kPa). ### Claim 17 (depends on 1) The process as set forth in claim 1 wherein at least a portion of the C5-backbone substrate is derived from a pentose. ### Claim 18 A process for preparing a glutaric acid product, the process comprising: a) converting at least a portion of a pentose source to a C5-backbone substrate comprising pentaric acid or derivative thereof, and b) converting, in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support, at least a portion of the pentaric acid or derivative thereof to a glutaric acid product of formula II wherein R1 is independently a salt-forming ion, hydrogen, hydrocarbyl, substituted hydrocarbyl, or lactone thereof. ### Claim 19 (depends on 18) The process as set forth in claim 18 wherein the glutaric acid product comprises glutaric acid. ### Claim 20 (depends on 18) The process as set forth in claim 18 wherein the process further comprises converting a source of carbohydrates to the pentose source. ### Claim 21 A process for preparing a glutaric acid product, the process comprising: a) reacting a pentose with oxygen, in the presence of a solvent, and an oxidation catalyst and in the absence of added base, to convert at least a portion of the pentose to at least one pentaric acid and/or derivative thereof, and b) reacting, in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support and a halogen source, at least a portion of the at least one pentaric acid and/or derivative thereof and hydrogen, to convert at least a portion of the at least one pentaric acid and/or derivative thereof to a glutaric acid product of formula II wherein R1 is independently a salt-forming ion, hydrogen, hydrocarbyl, substituted hydrocarbyl, or lactone thereof. ### Claim 22 (depends on 21) The process as set forth in claim 21 wherein a solvent is added to step b) to solubilize the at least one pentaric acid and/or derivative thereof. ### Claim 23 A process for producing a glutaric acid product from a pentose, the process comprising: converting by heterogeneous chemocatalysis at least a portion of the pentose to the glutaric acid product in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support, wherein the glutaric acid product is of formula II wherein R1 is independently a salt-forming ion, hydrogen, hydrocarbyl, substituted hydrocarbyl, or lactone thereof. ### Claim 24 (depends on 23) The process as set forth in claim 23 wherein the process comprises: a) converting by chemocatalysis at least a portion of the pentose to pentaric acid or derivative thereof, and b) converting by heterogeneous chemocatalysis at least a portion of the pentaric acid or derivative thereof to the glutaric acid product. ### Claim 25 (depends on 24) The process as set forth in claim 24 wherein the glutaric acid product comprises glutaric acid. ### Claim 26 (depends on 24) The process of claim 24 wherein the pentose comprises xylose and the pentaric acid or derivative thereof comprises xylaric acid or derivative thereof. ### Claim 27 (depends on 24) The process of claim 24 wherein the pentaric acid is xylaric acid. ### Claim 28 (depends on 21) A process of claim 21 wherein the oxygen is supplied to the reaction as air, oxygen-enriched air, oxygen alone, or oxygen with one or more other constituents substantially inert to the reaction. ### Claim 29 (depends on 21) The process as set forth in claim 21 wherein at least a portion of the at least one pentaric acid and/or derivative is solubilized with a weak carboxylic acid. ### Claim 30 (depends on 21) The process as set forth in claim 21 wherein the hydrodeoxygenation catalyst comprises a d-block metal selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof. ### Claim 31 (depends on 21) The process as set forth in claim 21 wherein the halogen source comprises ionic, atomic, and/or molecular forms of bromine or iodine. ### Claim 32 (depends on 29) The process as set forth in claim 29 wherein the halogen source comprises hydrogen bromide. ### Claim 33 (depends on 7) The process as set forth in claim 7 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof. ### Claim 34 (depends on 10) The process as set forth in claim 10 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof. ### Claim 35 (depends on 1) The process as set forth in claim 1 wherein the glutaric acid product comprises glutaric acid. ### Claim 36 (depends on 21) The process as set forth in claim 21 wherein the glutaric acid product comprises glutaric acid.