WO2015126584A1 - Process for the manufacture of hydrochlorofluoroolefins - Google Patents

Process for the manufacture of hydrochlorofluoroolefins Download PDF

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Publication number
WO2015126584A1
WO2015126584A1 PCT/US2015/013204 US2015013204W WO2015126584A1 WO 2015126584 A1 WO2015126584 A1 WO 2015126584A1 US 2015013204 W US2015013204 W US 2015013204W WO 2015126584 A1 WO2015126584 A1 WO 2015126584A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
trans
group
isomerization
chloroalkane
Prior art date
Application number
PCT/US2015/013204
Other languages
English (en)
French (fr)
Inventor
Maher Y. Elsheikh
Anne Pigamo
Sri R. Seshadri
Original Assignee
Arkema Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US14/183,828 external-priority patent/US8987535B2/en
Application filed by Arkema Inc. filed Critical Arkema Inc.
Priority to CN201580009258.0A priority Critical patent/CN106061929A/zh
Priority to BR112016019246A priority patent/BR112016019246A2/pt
Priority to EP15752266.5A priority patent/EP3107883A4/en
Priority to KR1020167022720A priority patent/KR102354556B1/ko
Priority to CA2940149A priority patent/CA2940149C/en
Priority to JP2016552956A priority patent/JP2017509606A/ja
Priority to MX2016010693A priority patent/MX2016010693A/es
Publication of WO2015126584A1 publication Critical patent/WO2015126584A1/en

Links

Classifications

    • 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)
PCT/US2015/013204 2014-02-19 2015-01-28 Process for the manufacture of hydrochlorofluoroolefins WO2015126584A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CN201580009258.0A CN106061929A (zh) 2014-02-19 2015-01-28 用于制造氢氯氟烯烃的方法
BR112016019246A BR112016019246A2 (pt) 2014-02-19 2015-01-28 processo paraa fabricação de hidroclorofluoro-olefinas
EP15752266.5A EP3107883A4 (en) 2014-02-19 2015-01-28 Process for the manufacture of hydrochlorofluoroolefins
KR1020167022720A KR102354556B1 (ko) 2014-02-19 2015-01-28 하이드로클로로플루오로올레핀의 제조 방법
CA2940149A CA2940149C (en) 2014-02-19 2015-01-28 Process for the manufacture of hydrochlorofluoroolefins
JP2016552956A JP2017509606A (ja) 2014-02-19 2015-01-28 ヒドロクロロフルオロオレフィンを製造するためのプロセス
MX2016010693A MX2016010693A (es) 2014-02-19 2015-01-28 Proceso para la fabricacion de hidroclorofluoroolefinas.

Applications Claiming Priority (2)

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

Publications (1)

Publication Number Publication Date
WO2015126584A1 true WO2015126584A1 (en) 2015-08-27

Family

ID=53878808

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/013204 WO2015126584A1 (en) 2014-02-19 2015-01-28 Process for the manufacture of hydrochlorofluoroolefins

Country Status (8)

Country Link
EP (1) EP3107883A4 (pt)
JP (1) JP2017509606A (pt)
KR (1) KR102354556B1 (pt)
CN (1) CN106061929A (pt)
BR (1) BR112016019246A2 (pt)
CA (1) CA2940149C (pt)
MX (1) MX2016010693A (pt)
WO (1) WO2015126584A1 (pt)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018135320A (ja) * 2017-01-06 2018-08-30 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． （ｅ）−１−クロロ−３，３，３−トリフルオロプロペン、ｈｆ、及び重質有機化合物、並びに反応器パージを分離するためのシステム及び方法
CN108473398A (zh) * 2016-01-15 2018-08-31 中央硝子株式会社 反式-1-氯-3,3,3-三氟丙烯的制造方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN113527047A (zh) * 2020-04-22 2021-10-22 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

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050256348A1 (en) * 1995-10-23 2005-11-17 Solvay S.A. Process for the preparation of 1,1,1,3,3-pentafluoropropane
US20110218370A1 (en) * 2008-11-19 2011-09-08 Arkema Inc. Process for the manufacture of hydrochlorofluoroolefins
US20120059199A1 (en) * 2010-09-03 2012-03-08 Pokrovski Konstantin A 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
FR2989374A1 (fr) * 2012-04-11 2013-10-18 Arkema France Procede de preparation d'un compose olefinique sous forme d'un isomere specifique.
US20140005447A1 (en) * 2012-06-29 2014-01-02 Central Glass Company, Limited Method for Production of 1-Chloro-3,3,3-Trifluoropropene
US20140228600A1 (en) * 2008-11-19 2014-08-14 Arkema Inc. Process for the manufacture of hydrochlorofluoroolefins

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
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
CN104603089B (zh) * 2012-06-13 2016-08-24 中央硝子株式会社 1-氯-3,3,3-三氟-1-丙烯及1,3,3,3-四氟丙烯的制造方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050256348A1 (en) * 1995-10-23 2005-11-17 Solvay S.A. Process for the preparation of 1,1,1,3,3-pentafluoropropane
US20110218370A1 (en) * 2008-11-19 2011-09-08 Arkema Inc. Process for the manufacture of hydrochlorofluoroolefins
US20140228600A1 (en) * 2008-11-19 2014-08-14 Arkema Inc. Process for the manufacture of hydrochlorofluoroolefins
US20120059199A1 (en) * 2010-09-03 2012-03-08 Pokrovski Konstantin A 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
FR2989374A1 (fr) * 2012-04-11 2013-10-18 Arkema France Procede de preparation d'un compose olefinique sous forme d'un isomere specifique.
US20140005447A1 (en) * 2012-06-29 2014-01-02 Central Glass Company, Limited Method for Production of 1-Chloro-3,3,3-Trifluoropropene

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP3107883A4 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108473398A (zh) * 2016-01-15 2018-08-31 中央硝子株式会社 反式-1-氯-3,3,3-三氟丙烯的制造方法
US20190031583A1 (en) * 2016-01-15 2019-01-31 Central Glass Company, Limited Method for Producing Trans-1-Chloro-3,3,3-Trifluoropropene
US10519083B2 (en) * 2016-01-15 2019-12-31 Central Glass Company, Limited Method for producing trans-1-chloro-3,3,3-trifluoropropene
CN114276211A (zh) * 2016-01-15 2022-04-05 中央硝子株式会社 反式-1-氯-3,3,3-三氟丙烯的制造方法
CN108473398B (zh) * 2016-01-15 2022-05-06 中央硝子株式会社 反式-1-氯-3,3,3-三氟丙烯的制造方法
JP2018135320A (ja) * 2017-01-06 2018-08-30 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． （ｅ）−１−クロロ−３，３，３−トリフルオロプロペン、ｈｆ、及び重質有機化合物、並びに反応器パージを分離するためのシステム及び方法

Also Published As

Publication number Publication date
KR20160122745A (ko) 2016-10-24
CA2940149C (en) 2022-06-21
EP3107883A4 (en) 2017-07-05
JP2017509606A (ja) 2017-04-06
CA2940149A1 (en) 2015-08-27
CN106061929A (zh) 2016-10-26
EP3107883A1 (en) 2016-12-28
KR102354556B1 (ko) 2022-01-25
BR112016019246A2 (pt) 2017-10-10
MX2016010693A (es) 2016-11-23

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