CA2940149C - Procede de fabrication d'hydrochlorofluoroolefines - Google Patents

Procede de fabrication d'hydrochlorofluoroolefines Download PDF

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Publication number
CA2940149C
CA2940149C CA2940149A CA2940149A CA2940149C CA 2940149 C CA2940149 C CA 2940149C CA 2940149 A CA2940149 A CA 2940149A CA 2940149 A CA2940149 A CA 2940149A CA 2940149 C CA2940149 C CA 2940149C
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Canada
Prior art keywords
catalyst
trans
isomerization
group
cis
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CA2940149A
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English (en)
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CA2940149A1 (fr
Inventor
Maher Y. Elsheikh
Anne Pigamo
Sri R. Seshadri
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Arkema Inc
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Arkema Inc
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Publication date
Priority claimed from US14/183,828 external-priority patent/US8987535B2/en
Application filed by Arkema Inc filed Critical Arkema Inc
Publication of CA2940149A1 publication Critical patent/CA2940149A1/fr
Application granted granted Critical
Publication of CA2940149C publication Critical patent/CA2940149C/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04—Alumina
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/063—Titanium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé de fabrication de 1-chloro-3,3,3-trifluoropropène trans (1233zd trans) par fluoration du 1230za et/ou du 240fa jusqu'à obtenir un mélange cis/trans du 1233zd, séparation de l'isomère trans suivie par une isomérisation de 1233zd cis en 1233zd trans dans l'étape de fluoration. L'étape de fluoration est effectuée dans la phase gazeuse ou la phase liquide. L'isomérisation est effectuée dans la phase gazeuse avec un catalyseur au Cr hétérogène à surface élevée, supporté ou non supporté.
CA2940149A 2014-02-19 2015-01-28 Procede de fabrication d'hydrochlorofluoroolefines Active CA2940149C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US14/183,828 US8987535B2 (en) 2008-11-19 2014-02-19 Process for the manufacture of hydrochlorofluoroolefins
US14/183,828 2014-02-19
PCT/US2015/013204 WO2015126584A1 (fr) 2014-02-19 2015-01-28 Procédé de fabrication d'hydrochlorofluorooléfines

Publications (2)

Publication Number Publication Date
CA2940149A1 CA2940149A1 (fr) 2015-08-27
CA2940149C true CA2940149C (fr) 2022-06-21

Family

ID=53878808

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2940149A Active CA2940149C (fr) 2014-02-19 2015-01-28 Procede de fabrication d'hydrochlorofluoroolefines

Country Status (8)

Country Link
EP (1) EP3107883A4 (fr)
JP (1) JP2017509606A (fr)
KR (1) KR102354556B1 (fr)
CN (1) CN106061929A (fr)
BR (1) BR112016019246A2 (fr)
CA (1) CA2940149C (fr)
MX (1) MX390802B (fr)
WO (1) WO2015126584A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6826280B2 (ja) * 2016-01-15 2021-02-03 セントラル硝子株式会社 トランス−１−クロロ−３，３，３−トリフルオロプロペンの製造方法
US20180194703A1 (en) * 2017-01-06 2018-07-12 Honeywell International Inc. Systems and methods for separating (e)-1-chloro-3,3,3-trifluoropropene, hf, and a heavy organic and reactor purge
CN108033872B (zh) * 2017-12-05 2021-07-09 安庆市华璞环保材料科技有限责任公司 一种清洁环保生产1,1’,2,3-四氯丙烯的方法及其设备
CN113527047B (zh) * 2020-04-22 2024-08-16 陕西中蓝化工科技新材料有限公司 一种联产制备反式-HFO-1234ze和顺式-HFO-1234ze的工艺
CN116139890A (zh) * 2023-04-24 2023-05-23 北京宇极科技发展有限公司 一种硼元素造孔的高比表面积铬基催化剂和高比例z-含氟烯烃/e-含氟烯烃的制备方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2740132B1 (fr) * 1995-10-23 1997-12-19 Solvay Procede pour la preparation de 1,1,1,3,3-pentafluoropropane
US5705779A (en) * 1996-08-08 1998-01-06 Alliedsignal Inc. Preparation of 1,1,1,3,3-pentachloropropane by photochlorination of 1,1,1,3-tetrachloropropane
US9738577B2 (en) * 2006-10-11 2017-08-22 Honeywell International Inc. Process for the manufacture of 1,1,1,3,3-pentachloropropane
EP2349962B1 (fr) * 2008-11-19 2020-02-26 Arkema Inc. Procédé de fabrication d'hydrochlorofluorooléfines
US8987534B2 (en) * 2008-11-19 2015-03-24 Arkema Inc. Process for the manufacture of hydrochlorofluoroolefins
CN101544535B (zh) * 2009-05-01 2012-07-18 浙江三美化工股份有限公司 一种合成1,1,1,3,3-五氯丙烷的制备方法
US8704017B2 (en) * 2010-09-03 2014-04-22 Honeywell International Inc. Continuous low-temperature process to produce trans-1-chloro-3,3,3-trifluoropropene
US8436217B2 (en) * 2011-04-25 2013-05-07 Honeywell International Inc. Integrated process to co-produce 1,1,1,3,3-pentafluoropropane, trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene
JP5821633B2 (ja) * 2011-12-29 2015-11-24 セントラル硝子株式会社 １−クロロ−３，３，３−トリフルオロプロペンの製造方法
US8829254B2 (en) * 2012-02-14 2014-09-09 Honeywell International Inc. Process for making 1,3,3,3-tetrafluoropropene
JP5858836B2 (ja) * 2012-03-19 2016-02-10 株式会社トクヤマ ポリクロロプロパンの製造方法
FR2989374A1 (fr) * 2012-04-11 2013-10-18 Arkema France Procede de preparation d'un compose olefinique sous forme d'un isomere specifique.
JP6156374B2 (ja) * 2012-06-13 2017-07-05 セントラル硝子株式会社 １−クロロ−３，３，３−トリフルオロ−１−プロペン及び１，３，３，３−テトラフルオロプロペンの製造方法
JP6107465B2 (ja) * 2012-06-29 2017-04-05 セントラル硝子株式会社 １−クロロ−３，３，３−トリフルオロプロペンの製造方法

Also Published As

Publication number Publication date
WO2015126584A1 (fr) 2015-08-27
CA2940149A1 (fr) 2015-08-27
KR20160122745A (ko) 2016-10-24
CN106061929A (zh) 2016-10-26
KR102354556B1 (ko) 2022-01-25
BR112016019246A2 (pt) 2017-10-10
EP3107883A4 (fr) 2017-07-05
MX2016010693A (es) 2016-11-23
EP3107883A1 (fr) 2016-12-28
JP2017509606A (ja) 2017-04-06
MX390802B (es) 2025-03-21

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