EP2220014A2 - Procedes de synthese de 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, et 1,1,1,4,4,5,5,5-octafluoro-2-pentene - Google Patents

Procedes de synthese de 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, et 1,1,1,4,4,5,5,5-octafluoro-2-pentene

Info

Publication number
EP2220014A2
EP2220014A2 EP08861859A EP08861859A EP2220014A2 EP 2220014 A2 EP2220014 A2 EP 2220014A2 EP 08861859 A EP08861859 A EP 08861859A EP 08861859 A EP08861859 A EP 08861859A EP 2220014 A2 EP2220014 A2 EP 2220014A2
Authority
EP
European Patent Office
Prior art keywords
cfc
octafluoro
catalyst
pentyne
hydrogen
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP08861859A
Other languages
German (de)
English (en)
Inventor
Mario Joseph Nappa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP2220014A2 publication Critical patent/EP2220014A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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

Definitions

  • the addition reaction may be practiced with a solvent or diluent for the CFC-12 and TFE.
  • a solvent or diluent for the CFC-12 and TFE typically, the CFC-12 and TFE are diluted; however, the diluent may be primarily the CFC-41 -1 Omca produced in the addition reaction.
  • solvents which may be used include CH 2 CI 2 , CHCI 3 , CCI 4 , CHCI 2 CF 3 , CCIF 2 CCIF 2 , and cyc/o-C 4 CI 2 F6 and mixtures thereof.
  • the addition reaction zone temperature is typically in the range of from about 0 0 C to about 100 0 C. In another embodiment, the addition reaction zone temperature is in the range of from about 2O 0 C to about 8O 0 C.
  • the reaction pressure may vary widely. In another embodiment, the reaction is carried out at elevated pressures, particularly pressures generated autogenously in conformity with the reaction temperature employed. In certain embodiments, the pressure may be adjusted by controlling the amount of unreacted CFC-12 and TFE.
  • the CFC-41-I Omca produced by the addition reaction as described above can be used to produce CFC-1419myx by catalytic dehalogenation.
  • the catalyst is palladium on barium sulfate catalyst that may contain from about 0.05% to 10% by weight palladium.
  • copper and nickel on carbon may contain from about 1 % to about 25% by weight copper and nickel combined on the carbon support.
  • the carbon support may be any of the carbon supports as described previously herein for other catalysts.
  • the weight ratio of the copper to nickel in the copper and nickel on carbon catalyst may range from about 2:1 to about 1 :2.
  • the palladium/barium chloride on alumina catalyst may contain from about 1 % to about 25% by weight barium chloride and from about 0.05% to about 10% by weight palladium relative to the total weight of the catalyst composition. Preparation of a palladium/barium chloride on alumina catalyst is described in U.S. Patent No. 5,243,103, the disclosure of which is herein incorporated by reference.
  • the dehalogenation reaction zone temperature is typically in the range of from about 200 0 C to about 500 0 C.
  • the addition reaction zone temperature is in the range of from about 300 0 C to about 450 0 C.
  • the dehalogenation reaction pressure may vary widely. In another embodiment, the reaction is carried out at elevated pressures.
  • the CFC-1419myx may be further reacted with more hydrogen to produce hexafluoro-2-butyne (CF 3 C ⁇ CCF 3 ).
  • This second dehalogenation reaction may be conducted under the same conditions and with the same catalysts as described above for the dehalogenation reaction for converting CFC-41 -I Omca to CFC-1419myx.
  • conditions may vary from the previous dehalogenation reaction in order to optimize production of octafluoro-2- pentyne and minimize undesirable by-products.
  • the reactor effluent may comprise CFC- 1419myx, octafluoro-2-pentyne, and any unreacted CFC-41 -1 Omca.
  • the hydrogenation reaction is conducted in a solvent.
  • the solvent is an alcohol.
  • Typical alcohol solvents include ethanol, /-propanol and n-propanol.
  • the solvent is a fluorocarbon or hydrofluorocarbon.
  • Typical fluorocarbons or hydrofluorocarbons include 1 ,1 ,1 ,2,2,3,4,5,5,5- decafluoropentane and 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane.
  • the process is conducted in a continuous process in the gas phase.
  • reaction of the octafluoro-2-pentyne with hydrogen in the presence of the catalyst may be done with addition of hydrogen in portions, with increases in the pressure of the vessel of no more than about 100 psi with each addition.
  • the addition of hydrogen is controlled so that the pressure in the vessel increases no more than about 50 psi with each addition.
  • hydrogen can be added in larger increments for the remainder of the reaction.
  • a mixture of octafluoro- 2-pentyne and hydrogen are passed through a reaction zone containing the catalyst.
  • the molar ratio of hydrogen to octafluoro-2-pentyne is about 1 :1 .
  • the molar ratio of hydrogen to octafluoro-2-pentyne is less than 1 :1.
  • the molar ratio of hydrogen to octafluoro- 2-pentyne is about 0.67:1.0.
  • the reaction zone is maintained at ambient temperature.
  • the reaction zone is maintained at a temperature of 30 0 C.
  • the reaction zone is maintained at a temperature of about 40 0 C.
  • the flow rate of octafluoro-2-pentyne and hydrogen is maintained so as to provide a residence time in the reaction zone of about 30 seconds.
  • the flow rate of octafluoro-2-pentyne and hydrogen is maintained so as to provide a residence time in the reaction zone of about 15 seconds.
  • the flow rate of octafluoro-2-pentyne and hydrogen is maintained so as to provide a residence time in the reaction zone of about 7 seconds. It will be understood, that contact time in the reaction zone is reduced by increasing the flow rate of octafluoro-2-pentyne and hydrogen into the reaction zone.
  • the amount of palladium on the support in the Lindlar catalyst is 5% by weight. In another embodiment, the amount of palladium on the support in the
  • Lindlar catalyst is greater than 5% by weight.
  • the amount of palladium on the support can be from about 5% by weight to about 1 % by weight.
  • Example 3 demonstrates the hydrogenation of octafluoro-2-pentyne with 1 % catalyst by weight.

Landscapes

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

Abstract

L'invention concerne un procédé consistant à faire réagir CF3CF2CCI2CF2CF3 (CFC-41 -10mca) avec de l'hydrogène en présence d'un catalyseur de déshalogénation pour produire CF3CF2CCI=CFCF3 (CFC-1419myx). Cette invention concerne également un procédé consistant à faire réagir CF3CF2CCI=CFCF3 (CFC- 1419myx) avec de l'hydrogène en présence d'un catalyseur de déshalogénation pour produire CF3CF2C≡CCF3 (octafluoro-2-pentyne). L'invention a aussi trait à un procédé consistant à faire réagir CF3CF2CCI2CF2CF3 (CFC-41 -10mca) avec de l'hydrogène en présence d'un catalyseur de déshalogénation pour produire CF3CF2C≡CCF3 (octafluoro-2-pentyne). En outre, l'invention porte sur un procédé servant à faire réagir CF3CF2C≡CCF3, dans un récipient sous pression, avec un catalyseur Lindlar et de l'hydrogène pour produire CF3CF2CH=CHCF3 (1,1,1,4,4,5,5,5-octafluoro-2- pentène).
EP08861859A 2007-12-17 2008-12-17 Procedes de synthese de 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, et 1,1,1,4,4,5,5,5-octafluoro-2-pentene Withdrawn EP2220014A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1424807P 2007-12-17 2007-12-17
PCT/US2008/087063 WO2009079525A2 (fr) 2007-12-17 2008-12-17 Procédés de synthèse de 3-chloroperfluoro-2-pentène, octafluoro-2-pentyne, et 1,1,1,4,4,5,5,5-octafluoro-2-pentène

Publications (1)

Publication Number Publication Date
EP2220014A2 true EP2220014A2 (fr) 2010-08-25

Family

ID=40473812

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08861859A Withdrawn EP2220014A2 (fr) 2007-12-17 2008-12-17 Procedes de synthese de 3-chloroperfluoro-2-pentene, octafluoro-2-pentyne, et 1,1,1,4,4,5,5,5-octafluoro-2-pentene

Country Status (4)

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

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009142642A1 (fr) * 2008-05-23 2009-11-26 E. I. Du Pont De Nemours And Company Procédé à sélectivité élevée pour préparer des dihydrofluoralcènes
JP2015507666A (ja) 2011-12-21 2015-03-12 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 高温ヒートポンプでのｅ−１，１，１，４，４，５，５，５−オクタフルオロ−２−ペンテンおよび任意選択的に１，１，１，２，３−ペンタフルオロプロパンの使用
JP2015507716A (ja) 2011-12-21 2015-03-12 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 動力サイクルでのｅ−１，１，１，４，４，５，５，５−オクタフルオロ−２−ペンテンおよび任意選択的に、１，１，１，２，３−ペンタフルオロプロパンを含む組成物の使用
EP2794803A1 (fr) 2011-12-21 2014-10-29 E. I. Du Pont de Nemours and Company Utilisation du e-1,1,1,4,4,5,5,5-octafluoro-2-pentène et éventuellement de 1,1,1,2,3-pentafluoropropane dans des refroidisseurs
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
US11452238B2 (en) 2017-06-07 2022-09-20 3M Innovative Properties Company Fluids for immersion cooling
US20210070686A1 (en) * 2017-12-21 2021-03-11 3M Innovative Properties Company Methods of making polyfunctional polyfluorinated compounds
US11773352B2 (en) 2018-12-26 2023-10-03 3M Innovative Properties Company Hydrochlorofluoroolefins and methods of using same
US20230402680A1 (en) 2020-11-03 2023-12-14 3M Innovative Properties Company Fluids for immersion cooling of electronic components

Family Cites Families (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
WO1993016973A1 (fr) * 1992-02-28 1993-09-02 Daikin Industries, Ltd. Procede de production de 1,1,1,2,2,4,4,5,5,5-decafluoropentane
WO2003041148A1 (fr) * 2001-11-08 2003-05-15 Zeon Corporation Gaz pour reaction de plasma, son procede de production et d'utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009079525A3 *

Also Published As

Publication number Publication date
WO2009079525A2 (fr) 2009-06-25
CN101903313A (zh) 2010-12-01
WO2009079525A3 (fr) 2009-11-12
JP2011506611A (ja) 2011-03-03

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