# US 12,180,134 B2 · Process for the reduction of RfC=CX impurities in fluoroolefins > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,134 B2 - Document ID: US12180134B2 - Status: Granted - Kind: B2 - Application number: 18/528,224 - Filed: 2023-12-04 - Published: 2024-03-28 - Granted: 2024-12-31 - Earliest claimed: 2013-03-15 - Assignees: The Chemours Company Fc, LLC - Applicants: The Chemours Company Fc, LLC - Inventors: Mario Joseph Nappa; Xuehui Sun; David Richard Corbin - Web page: https://patentgrep.com/patent/US12180134B2 ## CPC - C07C 17/389: by adsorption on solids - C07C 17/087: to unsaturated halogenated hydrocarbons - C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons - Y02P 20/582: Recycling of unreacted starting or intermediate materials - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract This disclosure relates to processes which involve: contacting a mixture comprising at least one fluoroolefin and at least one impurity with at least one zeolite to reduce the concentration of the at least one impurity in the mixture; and the at least one zeolite is selected from the group consisting of zeolites having pore opening of at least 4 Angstroms and no more than about 5 Angstroms, zeolites having pore opening of at least about 5 Angstroms and Sanderson electronegativity of no more than about 2.6, and mixtures thereof; provided that the at least one zeolite is not zeolite 4A. This disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF3CF═CH2, CF3CH═CHF, and mixtures thereof; and relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF3CCl═CH2, CF3CH═CHCl, and mixtures thereof. ## Claims ### Claim 1 A process comprising: a) providing an activated zeolite; b) contacting a mixture having at least one R71C≡CX impurity at a first level, wherein Rf is a straight-chain perfluorinated alkyl group, and X is H, F, Cl, Br, or I, with said activated zeolite at a pressure of between 10 kPa and 3000 kPa; c)reducing said level of said impurity to a second level lower than said first level with said activated zeolite which consists essentially of at least one zeolite having at least one of a pore opening of at least 4 Angstroms and no more than about 5 Angstroms and a pore opening of at least about 5 Angstroms and Sanderson electronegativity of no more than about 2.6, excluding zeolite 4A; and d) optionally, recovering a purified mixture having an impurity level lower than said first level. ### Claim 2 (depends on 1) The process of claim 1, wherein the mixture comprises at least one of a hydrochlorofluoroolefin and a hydrofluoroolefin. ### Claim 3 (depends on 2) The process of claim 2, wherein said at least one of a hydrochlorofluoroolefin and a hydrofluoroolefin is selected from CF3CF═CH2, CF3CH═CHF, CF3CH═CH2, CF3CCl═CH2, CF3CH═CHCl, CF3CH═CFCl, CF3CH═CF2, CF3CCl═CHF, CF3CF═CHF, CF3CF═CHCl, CF3CH═CCl2, CF3CCl═CHCl, and mixtures thereof, and wherein said at least one RfC≡CX impurity is selected from CF3C≡CH, CF3C≡CCl, and CF3C≡CF. ### Claim 4 (depends on 1) The process of claim 1, wherein said mixture includes at least one of CF3CF═CH2, CF3CH═CHF, CF3CH═CH2, CF3CCl═CH2, CF3CH═CHCl, and CF3CF═CHCl, and said impurity is selected from CF3C≡CH, CF3C≡CCl, and CF3C═CF. ### Claim 5 (depends on 1) The process of claim 1, wherein said mixture comprises at least one hydrofluoroolefin selected from CF3CF═CH2, CF3CH═CHF, CF3CH═CH2, CF3CH═CF2, and CF3CF═CHF. ### Claim 6 (depends on 1) The process of claim 1, wherein said mixture comprises at least one chlorofluoroolefin selected from CF3CCl═CH2, CF3CH═CHCl, CF3CH═CFCl CF3CF═CHCl, CF3CH═CCl2, and CF3CCl═CHCl. ### Claim 7 (depends on 3) The process of claim 3, wherein said at least one RfC≡CX impurity is selected from CF3C≡CH and CF3C≡CCl. ### Claim 8 (depends on 5) The process of claim 5, wherein said at least one hydrofluoroolefin is CF3CF═CH2, and wherein said at least one RfC≡CX impurity is CF3C≡CH. ### Claim 9 (depends on 5) The process of claim 5, wherein said at least one hydrofluoroolefin is CF3CH═CHF, and wherein said at least one RfC≡CX impurity is CF3C≡CH. ### Claim 10 (depends on 5) The process of claim 5, wherein said at least one hydrofluoroolefin is a mixture of CF3CF═CH2 and CF3CH═CHF, and wherein said at least one RfC≡CX impurity is CF3C≡CH. ### Claim 11 (depends on 4) The process of claim 4, wherein said at least one chlorofluoroolefin is CF3CH═CHCl, and wherein said at least one RfC≡CX impurity is CF3C≡CH. ### Claim 12 (depends on 1) The process of claim 1, wherein said at least one zeolite has a said pore opening of at least about 5 Angstroms and said Sanderson electronegativity of no more than about 2.6, excluding zeolite 4A. ### Claim 13 (depends on 1) The process of claim 1, wherein said at least one zeolite is selected from zeolite 5A, zeolite 13X, zeolite LSX, zeolite AW-300, zeolite AW-500, and mixtures thereof. ### Claim 14 (depends on 1) The process of claim 1, wherein said at least one zeolite is zeolite 5A, zeolite 13X, or mixtures thereof. ### Claim 15 (depends on 1) The process of claim 1, wherein said second level of said at least one RfC≡CX impurity is 300 ppm or less. ### Claim 16 (depends on 1) The process of claim 1, wherein said first level of said at least one RfC≡CX impurity is reduced at least about 20%. ### Claim 17 (depends on 1) The process of claim 1 further comprising recovering said purified mixture. ### Claim 18 (depends on 1) The process of claim 1, wherein said activated zeolite is activated by contacting one of a (1) zeolite having a pore opening of at least 4 Angstroms and no more than about 5 Angstroms and (2) a pore opening of at least about 5 Angstroms and Sanderson electronegativity of no more than about 2.6, excluding zeolite 4A with heated air.