# US 2014/0155659 A1 · PROCESS FOR THE MANUFACTURE OF 2-CHLORO-3,3,3-TRIFLUOROPROPENE (HCFO 1233xf) BY LIQUID PHASE FLUORINATION OF PENTACHLOROPROPANE > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0155659 A1 - Document ID: US20140155659A1 - Status: Published application - Kind: A1 - Application number: 13/885,470 - Filed: 2010-11-15 - Published: 2014-06-05 - Earliest claimed: 2010-11-15 - Assignees: Arkema France - Inventors: Laurent Wendlinger; Anne Pigamo; Phillipe Bonnet - Web page: https://patentgrep.com/patent/US20140155659A1 ## CPC - C07C 17/206: {the other compound being HX} - C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons - C07C 17/383: by distillation - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Process of catalytic fluorination in liquid phase of product 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane into product 2-chloro-3,3,3-trifluoropropene in presence of a catalyst. ## Claims ### Claim 1 Process comprising fluorination in the liquid phase of 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane into 2-chloro-3,3,3-trifluoropropene, with HF, in the presence of a catalyst. ### Claim 2 (depends on 1) Process according to claim 1, which is carried out in an organic medium. ### Claim 3 (depends on 1) Process according to claim 1, carried out in a solvent. ### Claim 4 (depends on 3) Process according to claim 3, in which the solvent is present in a dilution ratio of at least 20% with respect to said organic medium. ### Claim 5 (depends on 3) Process according to claim 3, in which the solvent is selected from the group consisting of 1,2-dichloroethane, 1,2,3-trichloropropane, 1-chloro-1-fluoroethane, 1,1-difluoroethane, 1,1-dichloroethane, 1,3-dichloro-1-fluorobutane, tetrachlorofluoropropane isomers, trichlorodifluoropropane isomers, dichlorotrifluoropropane isomers, 1,1,1,3,3-pentafluorobutane, 1,1,2-trichloro-2,2-difluoroethane, nitrated solvents, sulfones, 1,1,2-trichloro-2-fluoroethane, perchloroethylene, and mixtures thereof. ### Claim 6 (depends on 1) Process according to claim 1, in which the catalyst is an ionic liquid. ### Claim 7 (depends on 1) Process according to claim 1, in which the molar ratio catalyst 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane lies between 2 mol % and 90 mol %. ### Claim 8 (depends on 1) Process according to claim 1 further comprising adding chlorine. ### Claim 9 (depends on 1) Process according to claim 1 further comprising injecting gaseous anhydrous HCl. ### Claim 10 (depends on 9) Process according to the claim 9, in which the flow of gas, compared to the flow of 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane lies between 0.5:1 and 5:1. ### Claim 11 (depends on 1) Process according to claim 1, in which the product of the reaction is withdrawn in the gaseous state. ### Claim 12 (depends on 1) Process according to claim 1, in which the 1,1,1,2,2-pentachloropropane contains up to 20 mol % of isomer 1,1,2,2,3-pentachloropropane. ### Claim 13 (depends on 1) Process according to claim 1, in which the temperature of the reaction ranges between 30° C. and 200° C. ### Claim 14 (depends on 1) Process according to claim 1, in which the pressure of the reaction is higher than 2 bar. ### Claim 15 (depends on 1) Process according to claim 1, in which the molar ratio of HF:1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane lies between 0.5:1 and 50:1. ### Claim 16 (depends on 1) Process according to claim 1 further comprising adding a stabilizer, selected from the group consisting of p-methoxyphenol, t-amylphenol, thymol, limonene, d,l-limonene, quinones, hydroquinones, epoxides, amines and their mixtures. ### Claim 17 (depends on 16) Process according to claim 16, where the stabilizer is used in an amount of 5-1000 ppm. ### Claim 18 (depends on 1) Process according to claim 1, comprising: contacting 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane with hydrogen fluoride in a liquid phase in an organic medium under conditions sufficient to form a reaction mixture comprising 2-chloro-3,3,3-trifluoropropene; and separating the reaction mixture into a first stream comprising HCl, and a second stream comprising HF and 2-chloro-3,3,3-trifluoropropene. ### Claim 19 (depends on 18) Process according to claim 18, wherein the second stream comprises between 30 mol % and 70 mol % of 1233xf, between 30 mol % and 70 mol % of HF and less than 10 mol % of compounds of the series 242 and 243. ### Claim 20 (depends on 18) Process according to claim 18, wherein step (ii) is a distillation step. ### Claim 21 (depends on 18) Process according to claim 18 further comprising separating the second stream into a HF stream containing mainly HF, and an organic stream containing 2-chloro-3,3,3-trifluoropropene. ### Claim 22 (depends on 21) Process according to claim 21, wherein the organic stream is purified. ### Claim 23 (depends on 18) Process according to claim 18, further comprising a purging step for withdrawing heavies formed during said separating step. ### Claim 24 (depends on 18) Process according to claim 18 carried out continuously. ### Claim 25 (depends on 3) Process according to claim 3, in which the solvent is present in a dilution ratio between 20% and 80%. ### Claim 26 (depends on 3) Process according to claim 3, in which the solvent is present in a dilution ratio between 40% and 60%. ### Claim 27 (depends on 5) Process according to claim 5, in which the nitrated solvent is selected from the group consisting of nitromethane and nitrobenzene. ### Claim 28 (depends on 5) Process according to claim 5, in which the sulfone is selected from the group consisting of tetramethylene sulfone and dimethyl sulfone. ### Claim 29 (depends on 5) Process according to claim 5, in which the solvent is 1,1,2-trichloro-2,2-difluoroethane. ### Claim 30 (depends on 8) Process according to claim 8 wherein the molar ratio of chlorine to 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane is from 0.05 to 20 mole %. ### Claim 31 (depends on 8) Process according to claim 8 wherein the molar ratio of chlorine to 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane is from 0.5 to 15 mole %. ### Claim 32 (depends on 1) Process according to claim 1 in which the temperature of the reaction ranges between 40° C. and 170° C. ### Claim 33 (depends on 1) Process according to claim 1 in which the temperature of the reaction ranges between 50° C. and 150° C. ### Claim 34 (depends on 1) Process according to claim 1 in which the pressure of the reaction is between 4 and 50 bar. ### Claim 35 (depends on 1) Process according to claim 1, in which the pressure of the reaction is between 5 and 25 bar. ### Claim 36 (depends on 1) Process according to claim 1, in which the molar ratio of HF:1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane lies between 3:1 with 20:1. ### Claim 37 (depends on 1) Process according to claim 1, in which the molar ratio of HF:1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane is about 5:1. ### Claim 38 (depends on 16) Process according to claim 16, where the stabilizer is used in an amount of 10-500 ppm. ### Claim 39 (depends on 18) Process according to claim 18, wherein the second stream comprises between 30 mol % and 70 mol % of 1233xf, between 30 mol % and 70 mol % of HF and less than 5 mol %, of compounds of the series 242 and 243. ### Claim 40 (depends on 21) Process according to claim 21 wherein said separation is via decantation. ### Claim 41 (depends on 2) Process according to claim 2, wherein said organic medium further comprises a solvent. ### Claim 42 (depends on 40) Process according to claim 40, in which the solvent is present in a dilution ratio of at least 20% with respect to said organic medium. ### Claim 43 (depends on 41) Process according to claim 41, in which the solvent is selected from the group consisting of 1,2-dichloroethane, 1,2,3-trichloropropane, 1-chloro-1-fluoroethane, 1,1-difluoroethane, 1,1-dichloroethane, 1,3-dichloro-1-fluorobutane, tetrachlorofluoropropane isomers, trichlorodifluoropropane isomers, dichlorotrifluoropropane isomers, 1,1,1,3,3-pentafluorobutane, 1,1,2-trichloro-2,2-difluoroethane, nitrated solvents, sulfones, 1,1,2-trichloro-2-fluoroethane, perchloroethylene, and mixtures thereof.