# US 5,710,323 A · Process for producing monocarboxylic and/or dicarboxylic acids > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,710,323 A - Document ID: US5710323A - Status: Granted - Kind: A - Application number: 08/809,701 - Filed: 1997-03-27 - Granted: 1998-01-20 - Earliest claimed: 1994-09-29 - Assignees: Idemitsu Petrochemical Co., Ltd. - Inventors: Ryoichi Okuda; Tadashi Kato; Yoshio Okada - Web page: https://patentgrep.com/patent/US5710323A ## CPC - B01J 31/0227: {being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds} - C07C 51/10: by reaction with carbon monoxide - C07C 51/12: on an oxygen-containing group in organic compounds, e.g. alcohols - C07C 51/14: on a carbon-to-carbon unsaturated bond in organic compounds - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A process for producing a monocarboxylic acid and/or a dicarboxylic acid by the reaction of a starting compound selected from among saturated hydrocarbons, .alpha.-olefins of 6 to 20 carbon atoms, saturated monocarboxylic acids and esters of the acids either with both of carbon monoxide and water at the same time or first with carbon monoxide and then with water, wherein the reaction of the starting compound either with both of carbon monoxide and water or with carbon monoxide alone is conducted in a strong acid solution containing a trifluoromethane-sulfonic acid catalyst and an alcohol and/or an olefin of 3 to 5 carbon atoms. ## Claims ### Claim 1 A process for producing a monocarboxylic acid and/or a dicarboxylic acid by a reaction of a starting compound selected from the group consisting of a saturated hydrocarbon, a saturated monocarboxylic acid and a saturated monocarboxylic ester either with both of carbon monoxide and water at the same time or first with carbon monoxide and then with water, wherein the reaction of the starting compound either with both of carbon monoxide and water or with carbon monoxide alone is conducted in a strong acid solution containing at least trifluoromethane-sulfonic acid catalyst and an alcohol and/or an olefin of 3 to 5 carbon atoms. ### Claim 2 (depends on 1) The process of claim 1, wherein the product monocarboxylic acid and/or the product dicarboxylic acid is a monocarboxylic acid containing one more carbon atom than the starting compound and/or a dicarboxylic acid containing two more carbon atoms than the starting compound. ### Claim 3 (depends on 2) The process of claim 2, wherein the saturated hydrocarbon is used as the starting compound, to produce a monocarboxylic acid containing one more carbon atom than the starting compound and/or a dicarboxylic acid containing two more carbon atoms than the starting compound. ### Claim 4 (depends on 2) The process of claim 2, wherein the saturated monocarboxylic acid is used as the starting compound, to produce a saturated dicarboxylic acid containing one more carbon atom than the starting compound. ### Claim 5 (depends on 2) The process of claim 2, wherein the saturated monocarboxylic ester is used as the starting compound, to prepare a saturated monocarboxylic acid containing one more carbon atom than the starting compound. ### Claim 6 (depends on 1) The process of claim 1, wherein the starting compound selected from the group consisting of the saturated hydrocarbon, the saturated monocarboxylic acid and the saturated monocarboxylic ester contains an alkyl chain containing no tertiary hydrogen atoms. ### Claim 7 (depends on 1) The process of claim 1, wherein the alcohol has 3 to 8 carbon atoms. ### Claim 8 (depends on 7) The process of claim 7, wherein the alcohol has 3 to 5 carbon atoms. ### Claim 9 (depends on 1) The process of claim 1, wherein the saturated hydrocarbon and the saturated monocarboxylic acid contain 4 to 20 carbon atoms. ### Claim 10 (depends on 1) The process of claim 1, wherein the saturated hydrocarbon and the saturated monocarboxylic acid contain 8 to 20 carbon atoms. ### Claim 11 (depends on 1) The process of claim 1, wherein the starting compound is selected from the group consisting of the saturated hydrocarbon, the saturated monocarboxylic acid and the saturated monocarboxylic ester, and the reaction of the starting compound with carbon monoxide is carried out in a strong acid solution which comprises the trifluoromethane-sulfonic acid catalyst and the alcohol and contains no water. ### Claim 12 (depends on 11) The process of claim 11, wherein the starting compound is the saturated hydrocarbon, the saturated hydrocarbon is used in an amount of 100 to 10,000 mol % based on the alcohol, the alcohol is used in an amount of 1 to 50% by weight based on the trifluoromethane-sulfonic acid catalyst, and the reaction in the strong acid solution is carried out at an atmospheric pressure with a partial pressure of carbon monoxide of 0.1 to 10 MPa. ### Claim 13 (depends on 11) The process of claim 11, wherein the starting compound is the saturated monocarboxylic acid or the saturated monocarboxylic ester, the saturated monocarboxylic acid or the saturated monocarboxylic ester is used in an amount of 50 to 150 mol % based on the alcohol, the alcohol is used in an amount of 1 to 50% by weight based on the trifluoromethane-sulfonic acid catalyst, and the reaction in the strong acid solution is carried out at atmospheric pressure with a partial pressure of carbon monoxide of 0.1 to 10 MPa. ### Claim 14 (depends on 11, 12, 13) The method of any one of claims 11 to 13, wherein 50 to 200% by weight of water based on the trifluoromethane-sulfonic acid is added to a reaction mixture resulting from the reaction in the strong acid solution, to form the product monocarboxylic acid and/or the product dicarboxylic acid, which is then extracted with a solvent.