WO2009079525A3 - Processes for the synthesis of 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, and 1,1,1,4,4,5,5,5-octafluoro-2-pentene - Google Patents

Processes for the synthesis of 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, and 1,1,1,4,4,5,5,5-octafluoro-2-pentene Download PDF

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Publication number
WO2009079525A3
WO2009079525A3 PCT/US2008/087063 US2008087063W WO2009079525A3 WO 2009079525 A3 WO2009079525 A3 WO 2009079525A3 US 2008087063 W US2008087063 W US 2008087063W WO 2009079525 A3 WO2009079525 A3 WO 2009079525A3
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WO
WIPO (PCT)
Prior art keywords
octafluoro
pentene
pentyne
chloroperfluoro
synthesis
Prior art date
Application number
PCT/US2008/087063
Other languages
French (fr)
Other versions
WO2009079525A2 (en
Inventor
Mario Joseph Nappa
Original Assignee
E.I. Du Pont De Nemours And Company
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
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to JP2010539716A priority Critical patent/JP2011506611A/en
Priority to CN2008801209746A priority patent/CN101903313A/en
Priority to EP08861859A priority patent/EP2220014A2/en
Publication of WO2009079525A2 publication Critical patent/WO2009079525A2/en
Publication of WO2009079525A3 publication Critical patent/WO2009079525A3/en

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    • 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
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
    • C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
    • 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
    • C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine

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

Abstract

Disclosed is a process comprising reacting CF3CF2CCI2CF2CF3 (CFC-41 -10mca) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CF2CCI=CFCF3 (CFC-1419myx). Also disclosed herein is a process comprising reacting CF3CF2CCI=CFCF3 (CFC- 1419myx) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CF2C≡CCF3 (octafluoro-2-pentyne). Also disclosed herein is a process comprising reacting CF3CF2CCI2CF2CF3 (CFC-41 -10mca) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CF2C≡CCF3 (octafluoro-2-pentyne). In addition, a process for reacting CF3CF2C≡CCF3, in a pressure vessel, with a Lindlar catalyst and hydrogen to produce CF3CF2CH=CHCF3 (1,1,1,4,4,5,5,5-octafluoro-2- pentene) is disclosed.
PCT/US2008/087063 2007-12-17 2008-12-17 Processes for the synthesis of 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, and 1,1,1,4,4,5,5,5-octafluoro-2-pentene WO2009079525A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2010539716A JP2011506611A (en) 2007-12-17 2008-12-17 Method for synthesizing 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, and 1,1,1,4,4,5,5,5-octafluoro-2-pentene
CN2008801209746A CN101903313A (en) 2007-12-17 2008-12-17 Processes for the synthesis of 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, and 1,1,1,4,4,5,5,5-octafluoro-2-pentene
EP08861859A EP2220014A2 (en) 2007-12-17 2008-12-17 Processes for the synthesis of 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, and 1,1,1,4,4,5,5,5-octafluoro-2-pentene

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1424807P 2007-12-17 2007-12-17
US61/014,248 2007-12-17

Publications (2)

Publication Number Publication Date
WO2009079525A2 WO2009079525A2 (en) 2009-06-25
WO2009079525A3 true WO2009079525A3 (en) 2009-11-12

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/087063 WO2009079525A2 (en) 2007-12-17 2008-12-17 Processes for the synthesis of 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, and 1,1,1,4,4,5,5,5-octafluoro-2-pentene

Country Status (4)

Country Link
EP (1) EP2220014A2 (en)
JP (1) JP2011506611A (en)
CN (1) CN101903313A (en)
WO (1) WO2009079525A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101614967B1 (en) * 2008-05-23 2016-04-22 이 아이 듀폰 디 네모아 앤드 캄파니 High selectivity process to make dihydrofluoroalkenes
CN103998563A (en) 2011-12-21 2014-08-20 纳幕尔杜邦公司 Use of compositions comprising e-1,1,1,4,4,5,5,5-octafluoro-2-pentene and optionally, 1,1,1,2,3-pentafluoropropane in power cycles
EP2794804A1 (en) 2011-12-21 2014-10-29 E. I. Du Pont de Nemours and Company Use of e-1,1,1,4,4,5,5,5-octafluoro-2-pentene and optionally 1,1,1,2,3-pentafluoropropane in high temperature heat pumps
WO2013096426A1 (en) 2011-12-21 2013-06-27 E. I. Du Pont De Nemours And Company Use of e-1,1,1,4,4,5,5,5-octafluoro-2-pentene and optionally 1,1,1,2,3-pentafluoropropane in chillers
US20210079277A1 (en) * 2017-05-17 2021-03-18 Daikin Industries, Ltd. Composition containing compound useful as refrigerant, detergent, propellant, or the like, and refrigerating machine, large-sized air conditioner, or industrial process cooler each including said composition
KR102625643B1 (en) 2017-06-07 2024-01-15 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Fluids for immersion cooling
WO2019123342A1 (en) * 2017-12-21 2019-06-27 3M Innovative Properties Company Methods of making polyfunctional polyfluorinated compounds
WO2020136533A1 (en) * 2018-12-26 2020-07-02 3M Innovative Properties Company Hydrochlorofluoroolefins and methods of using same
CN116472635A (en) 2020-11-03 2023-07-21 3M创新有限公司 Fluid for immersing and cooling electronic component

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2900423A (en) * 1957-12-13 1959-08-18 Allied Chem Manufacture of perfluoropropene
EP0633237A1 (en) * 1992-02-28 1995-01-11 Daikin Industries, Limited Process for producing 1,1,1,2,2,4,4,5,5,5-decafluoropentane
EP1453082A1 (en) * 2001-11-08 2004-09-01 Zeon Corporation GAS FOR PLASMA REACTION, PROCESS FOR PRODUCING THE SAME, AND USE

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2900423A (en) * 1957-12-13 1959-08-18 Allied Chem Manufacture of perfluoropropene
EP0633237A1 (en) * 1992-02-28 1995-01-11 Daikin Industries, Limited Process for producing 1,1,1,2,2,4,4,5,5,5-decafluoropentane
EP1453082A1 (en) * 2001-11-08 2004-09-01 Zeon Corporation GAS FOR PLASMA REACTION, PROCESS FOR PRODUCING THE SAME, AND USE

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEPIC, PETROV, GALAKHOV, BELENKII, MYSOV, GERMAN: "Electrophilic isomerization of substituted perfluorocyclopropanes under the effect of SbF5", BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR, vol. 39, 1990, pages 1674 - 1680, XP002525967 *
HENNE, LATIF: "Perfluorinated alkene, alkyne and cycloalkene", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 76, 1954, pages 610 - 612, XP002525968 *

Also Published As

Publication number Publication date
WO2009079525A2 (en) 2009-06-25
JP2011506611A (en) 2011-03-03
EP2220014A2 (en) 2010-08-25
CN101903313A (en) 2010-12-01

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