# US 10,370,313 B2 · Manufacturing method of purified 1-chloro-2,3,3,3-Tetrafluoropropene and purified 1-chloro-2,3,3,3-tetrafluoropropene (Z) > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,370,313 B2 - Document ID: US10370313B2 - Status: Granted - Kind: B2 - Application number: 16/105,407 - Filed: 2018-08-20 - Published: 2019-01-03 - Granted: 2019-08-06 - Earliest claimed: 2016-02-26 - Assignees: AGC Inc. - Applicants: AGC Inc. - Inventors: Tomoaki Taniguchi; Jumpei Nomura; Takayuki Sakai; Takashi Hayase - Web page: https://patentgrep.com/patent/US10370313B2 ## CPC - C07C 17/383: by distillation - C07C 17/38: Separation; Purification; Stabilisation; Use of additives - C07C 17/386: with auxiliary compounds - C07C 21/18: containing fluorine - B01D 3/143: {by two or more of a fractionation, separation or rectification step} - B01D 11/04: of solutions which are liquid - B01D 2257/206: Organic halogen compounds - Y02P 20/10: Process efficiency - 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) - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract There is provided a method of efficiently manufacturing purified 1224yd containing 1224yd at a high concentration from a mixture containing 1224yd and a compound that forms an azeotropic composition or an azeotropic-like composition with 1224yd. A manufacturing method of purified 1224yd, includes making a first mixture of 1224yd and a compound (X1) forming an azeotropic composition or an azeotropic-like composition with 1224yd to be brought into contact with a first extraction solvent to obtain purified 1224yd not substantially containing the compound (X1). ## Claims ### Claim 1 A method of manufacturing purified 1-chloro-2,3,3,3-tetrafluoropropene, the method comprising: making a first mixture of 1-chloro-2,3,3,3-tetrafluoropropene and a compound (X1) that forms an azeotropic composition or an azeotropic-like composition with 1-chloro-2,3,3,3-tetrafluoropropene, and contacting the first mixture with a first extraction solvent to obtain purified 1-chloro-2,3,3,3-tetrafluoropropene not substantially comprising the compound (X1). ### Claim 2 A method of manufacturing purified 1-chloro-2,3,3,3-tetrafluoropropene (Z), the method comprising: making a second mixture of 1-chloro-2,3,3,3-tetrafluoropropene (Z) and a compound (X2) that forms an azeotropic composition or an azeotropic-like composition with 1-chloro-2,3,3,3-tetrafluoropropene (Z), and contacting the second mixture with a second extraction solvent to obtain purified 1-chloro-2,3,3,3-tetrafluoropropene (Z) not substantially comprising the compound (X2). ### Claim 3 (depends on 1) The method of claim 1, wherein the compound (X1) is a compound which exhibits a relative volatility between 1-chloro-2,3,3,3-tetrafluoropropene and the compound (X1) in the first mixture of 0.9 to 1.1. ### Claim 4 (depends on 2) The method of claim 2, wherein the compound (X2) is a compound which exhibits a relative volatility between 1-chloro-2,3,3,3-tetrafluoropropene (Z) and the compound (X2) in the second mixture of 0.9 to 1.1. ### Claim 5 (depends on 1) The method of claim 1, wherein the first extraction solvent is a solvent capable of making the relative volatility between 1-chloro-2,3,3,3-tetrafluoropropene and the compound (X1) smaller than 0.85 or larger than 1.15. ### Claim 6 (depends on 2) The method of claim 2, wherein the second extraction solvent is a solvent capable of making the relative volatility between 1-chloro-2,3,3,3-tetrafluoropropene (Z) and the compound (X2) smaller than 0.85 or larger than 1.15. ### Claim 7 (depends on 1) The method of claim 1, wherein the first extraction solvent is one selected from the group consisting of an alcohol having 1 to 3 carbon atoms and a carbonyl compound having 2 to 4 carbon atoms other than the carbon atom of a carbonyl group. ### Claim 8 (depends on 2) The method of claim 2, wherein the second extraction solvent is one selected from the group consisting of an alcohol having 1 to 3 carbon atoms and a carbonyl compound having 2 to 4 carbon atoms other than the carbon atom of a carbonyl group. ### Claim 9 (depends on 1) The method of claim 1, further comprising: obtaining a third mixture by mixing the first mixture and the first extraction solvent, and distilling the third mixture. ### Claim 10 (depends on 9) The method of claim 9, wherein the mixing is performed at a molar ratio of the first extraction solvent with respect to 1-chloro-2,3,3,3-tetrafluoropropene of 0.4 to 200. ### Claim 11 (depends on 2) The method of claim 2, further comprising: obtaining a fourth mixture by mixing the second mixture and the second extraction solvent, and distilling the fourth mixture. ### Claim 12 (depends on 11) The method of claim 11, wherein the mixing is performed at a molar ratio of the second extraction solvent with respect to 1-chloro-2,3,3,3-tetrafluoropropene (Z) of 0.4 to 200. ### Claim 13 (depends on 1) The method of claim 1, wherein the first mixture is an azeotropic composition or an azeotropic-like composition. ### Claim 14 (depends on 2) The method of claim 2, wherein the second mixture is an azeotropic composition or an azeotropic-like composition. ### Claim 15 (depends on 1) The method of claim 1, wherein the compound (X1) is 1-chloro-1,2,2,3,3,3-hexafluoropropane, 1-chloro-1,1,2,2,3,3-hexafluoropropane, 1-chloro-1,3,3,3-tetrafluoropropene, or 2-chloro-1,3,3,3-tetrafluoropropene. ### Claim 16 (depends on 2) The method of claim 2, wherein the compound (X2) is 1-chloro-1,2,2,3,3,3-hexafluoropropane, 1-chloro-1,1,2,2,3,3-hexafluoropropane, 1-chloro-1,3,3,3-tetrafluoropropene, 2-chloro-1,3,3,3-tetrafluoropropene, or 1-chloro-2,3,3,3-tetrafluoropropene (E). ### Claim 17 (depends on 1) The method of claim 1, wherein the first extraction solvent is a saturated hydrocarbon having 5 to 12 carbon atoms, a halogenated hydrocarbon having 1 to 10 carbon atoms which does not have an ether bond, an alcohol having 1 to 3 carbon atoms, or a carbonyl compound. ### Claim 18 (depends on 1) The method of claim 1, wherein the first extraction solvent is methanol, ethanol, or acetone. ### Claim 19 (depends on 2) The method of claim 2, wherein the second extraction solvent is a saturated hydrocarbon having 5 to 12 carbon atoms, a halogenated hydrocarbon having 1 to 10 carbon atoms which does not have an ether bond, an alcohol having 1 to 3 carbon atoms, or a carbonyl compound. ### Claim 20 (depends on 2) The method of claim 2, wherein the first extraction solvent is methanol, ethanol, or acetone.