EP1198441A4 - PRODUCTION OF ALIPHATIC FLUOROCARBONS - Google Patents

PRODUCTION OF ALIPHATIC FLUOROCARBONS

Info

Publication number
EP1198441A4
EP1198441A4 EP00950495A EP00950495A EP1198441A4 EP 1198441 A4 EP1198441 A4 EP 1198441A4 EP 00950495 A EP00950495 A EP 00950495A EP 00950495 A EP00950495 A EP 00950495A EP 1198441 A4 EP1198441 A4 EP 1198441A4
Authority
EP
European Patent Office
Prior art keywords
pyrolyzing
preparing
chloro
aliphatic fluorocarbon
products
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Withdrawn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
EP00950495A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP1198441A1 (en
Inventor
Lee Sprague
Daniel Graham
Louis Ferstandig
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.)
Halocarbon Products Corp
Original Assignee
Halocarbon Products Corp
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 Halocarbon Products Corp filed Critical Halocarbon Products Corp
Publication of EP1198441A1 publication Critical patent/EP1198441A1/en
Publication of EP1198441A4 publication Critical patent/EP1198441A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the present invention relates to processes for the production of aliphatic fluorocarbons.
  • Aliphatic fluorocarbons are a group of chemicals that range from inert, highly stable substances to reactive unsaturated fluorocarbons. As used throughout this disclosure
  • aliphatic fluorocarbon is defined as an aliphatic compound which has carbon to fluorine bonds, and which may also contain hydrogen and chlorine.
  • Aliphatic fluorocarbons may range from compounds having only single bonds to those having multiple bonds.
  • the single bond compounds are frequently inert and nonflammable.
  • Fluorocarbons having double bonds, fluoroolefins, are very reactive species useful in the production of a
  • Fluorocarbons having triple bonds are also very important.
  • the present invention relates to a new manufacturing process for preparing a
  • desired aliphatic fluorocarbon product comprising the following steps:
  • aliphatic fluorocarbon has previously been defined.
  • reactive aliphatic fluorocarbon intermediate compound is intended to mean any aliphatic
  • fluorocarbon which is capable of reacting with aliphatic fluorocarbons and other reactive
  • aliphatic fluorocarbons This term includes species such as radicals, ions or carbenes.
  • the new manufacturing process starts by creating reactive intermediates from a
  • reactive intermediate generation distinguishes it from hydrocarbon reactive intermediate
  • the undesired products can be recycled endlessly and the yields of the desired products will be enhanced.
  • initial yields can be converted to commercially viable processes. In some cases, where a
  • TFE is made from R 134a.
  • R 125 the undesired byproduct of TFE, can be converted to TFE at least in two ways; by reverting to the starting material, R 133a, and via another intermediate, R 134a which also serves as a starting material for TFE.
  • R 134 examples by the formation of R 134, presumably from TFE and hydrogen fluoride. Any hydrogen fluoride not reacting to reform carbon to fluorine bonds during the process may be
  • chloride may be generated. This does not represent an endpoint for those atoms because in the invention the addition of hydrogen chloride to the reactants results in the formation of
  • polymers can be subjected to the same separation and recycle steps as other volatile
  • This method of recycling to extinction has still another advantage. It provides a
  • Waste products normally have to be treated in special ways to keep them from
  • the present invention involves the discovery of new methods for preparing fluorocarbons, and some surprising products resulting from these methods.
  • the present invention involves the discovery of new methods for preparing fluorocarbons, and some surprising products resulting from these methods.
  • invention also involves the discovery that reactive fluorocarbon intermediates are quite different from reactive hydrocarbon intermediates and how these differences can be
  • the invention relates to the production of aliphatic
  • fluorocarbons comprising a process for generating reactive aliphatic fluorocarbon
  • the reactive intermediates are generated by
  • the invention relates to a process for preparing TFE in greater than 50% yield comprising pyrolyzing R 133a at a temperature below about
  • the invention relates to a process for preparing
  • PFP comprising pyrolyzing R 133a in the presence of R 22.
  • the invention relates to a process for preparing OFB comprising pyrolyzing R 124.
  • the invention relates to a process for preparing
  • CDFE comprising pyrolyzing R 133a.
  • the invention relates to a process for preparing DCDFE comprising pyrolyzing R 133a in the presence of R 22 and hydrogen chloride.
  • the invention relates to a process for preparing
  • OFB comprising pyrolyzing R 125.
  • the invention relates to a process for preparing R
  • the invention relates to a process for preparing R 114a comprising pyrolyzing R 124. In an eleventh preferred embodiment, the invention relates to a process for preparing PFB comprising pyrolyzing R 125.
  • the invention relates to a process for preparing
  • R 125 comprising pyrolyzing R 133a.
  • Pyrolyses of chemical compounds are usually performed under a variety of conditions at high temperatures with a variety of residence times, with or without diluents.
  • reaction tubes may be constructed of a variety of materials including
  • thermocouple in a thermowell centered in the tube.
  • Feed rates of the reactants are, of course, a function of the size of the reacting
  • Inert diluents were also used to change the residence time of the reactants in the reaction zone.
  • Inert diluents can be materials such as nitrogen, the noble gases,
  • Trifluoroethane Chem. Phys. Processes Combust.. 1996, pages 507-510. Salmon et al.
  • TFE trifluoroethylene
  • HFB l,l,l,4,4,4-hexafluoro-2-butene
  • CDFE 2-chloro-l,l-difluoroethylene
  • high temperature include l,l,l-trifluoro-2-propyne.
  • TFE can be made in yields exceeding 50%, contrary to any expectation from the work of Salmon et al.
  • R 133a When the same reactant, R 133a, is pyrolyzed at about 700°C and less than 10%
  • DCDFE can be prepared by performing the same pyrolysis
  • R 124 (Runs 11 and 12) or R 125 (Runs 13 and 14) good yields of OFB can be made.
  • R 125 also makes PFB and R 124 also makes R 114a.
  • R 133a The pyrolysis of R 133a almost always generates R 125 (Runs 2 and 5).
  • the pyrolysis of R 125 (Run 14) produces R 134a, which in turn, produces TFE (Run 15).
  • CDFE l-chloro-2,2-difluoroethylene
  • DCDFE l,l-dichloro-2,2-difluoroethylene
  • HFB l,l,l,4,4,4-hexafluoro-2-butene
  • OFB 1,1,1, 2,3, 4,4,4-octafluoro-2-butene
  • R 114a 1,1-dichloro- 1,2,2,2-tetrafluoroethane
  • R 12 dichlorodifluoromethane
  • R 123 l,l-dichloro-2,2,2-trifluoroethane
  • R 124 1-chloro- 1,2,2,2-tetrafluoroethane
  • R 13 chlorotrifluoromethane
  • R 133a l-chloro-2,2,2-trifluoroethane
  • R 134a 1,2,2,2-tetrafluoroethane
  • R 22 chlorodifluoromethane
  • TEFE tetrafluoroethylene
  • TFE trifluoroethylene
  • TeFE tetrafluroethytene
  • TFE t ⁇ fluoroeth lene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP00950495A 1999-07-21 2000-07-21 PRODUCTION OF ALIPHATIC FLUOROCARBONS Withdrawn EP1198441A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US14473999P 1999-07-21 1999-07-21
US144739P 1999-07-21
PCT/US2000/019863 WO2001007384A1 (en) 1999-07-21 2000-07-21 Production of aliphatic fluorocarbons

Publications (2)

Publication Number Publication Date
EP1198441A1 EP1198441A1 (en) 2002-04-24
EP1198441A4 true EP1198441A4 (en) 2003-01-22

Family

ID=22509912

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00950495A Withdrawn EP1198441A4 (en) 1999-07-21 2000-07-21 PRODUCTION OF ALIPHATIC FLUOROCARBONS

Country Status (10)

Country Link
EP (1) EP1198441A4 (cs)
JP (1) JP2003505439A (cs)
KR (1) KR20020029086A (cs)
CN (1) CN1258505C (cs)
AU (1) AU6359400A (cs)
BR (1) BR0012650A (cs)
CA (1) CA2380285A1 (cs)
CZ (1) CZ2002183A3 (cs)
PL (1) PL352765A1 (cs)
WO (1) WO2001007384A1 (cs)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7880040B2 (en) 2004-04-29 2011-02-01 Honeywell International Inc. Method for producing fluorinated organic compounds
US9308199B2 (en) 2004-04-29 2016-04-12 Honeywell International Inc. Medicament formulations
US7659434B2 (en) 2004-04-29 2010-02-09 Honeywell International Inc. Method for producing fluorinated organic compounds
US7674939B2 (en) 2004-04-29 2010-03-09 Honeywell International Inc. Method for producing fluorinated organic compounds
US8084653B2 (en) 2004-04-29 2011-12-27 Honeywell International, Inc. Method for producing fluorinated organic compounds
KR20070011554A (ko) 2004-04-29 2007-01-24 허니웰 인터내셔널 인코포레이티드 1,3,3,3-테트라플루오로프로펜의 합성 방법
US9024092B2 (en) 2006-01-03 2015-05-05 Honeywell International Inc. Method for producing fluorinated organic compounds
US9102579B2 (en) 2004-04-29 2015-08-11 Honeywell International Inc. Method for producing fluorinated organic compounds
US7951982B2 (en) 2004-04-29 2011-05-31 Honeywell International Inc. Method for producing fluorinated organic compounds
MXPA06012467A (es) * 2004-04-29 2007-01-29 Honeywell Int Inc Procesos para la sintesis de 1,3,3,3-tetrafluoropropeno.
US8383867B2 (en) 2004-04-29 2013-02-26 Honeywell International Inc. Method for producing fluorinated organic compounds
CN101351430A (zh) * 2005-11-03 2009-01-21 霍尼韦尔国际公司 氟化有机化合物的制备方法
CN103044190B (zh) * 2012-12-21 2014-12-24 巨化集团技术中心 一种三氟乙烯的制备方法
WO2016092340A1 (en) * 2014-12-11 2016-06-16 Arkema France Process for the preparation of 1-chloro-2,2-difluoroethane
US10259761B2 (en) * 2015-06-04 2019-04-16 Arkema Inc. Method for producing fluorinated olefins
CN107337578B (zh) * 2017-08-03 2020-07-24 北京宇极科技发展有限公司 一种气相催化合成全氟2-丁烯的方法

Citations (20)

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DD43244A (cs) *
US2413695A (en) * 1943-06-19 1947-01-07 Kinetic Chemicals Inc Fluorinated compounds and pyrolytic methods for preparing them
US2627529A (en) * 1947-10-23 1953-02-03 Socony Vacuum Oil Co Inc Pyrolysis of difluoromonochloroethane
GB1039468A (en) * 1962-07-25 1966-08-17 Pechiney Saint Gobain Improvements in and relating to the preparation of vinylidene fluoride
US4613709A (en) * 1984-08-20 1986-09-23 Solvay & Cie. Process for the pyrolytic dehydrochlorination of haloalkanes in the presence of an initiator based on chlorinated product and the initiator employed in such a process
WO1990008755A1 (en) * 1989-02-03 1990-08-09 E.I. Du Pont De Nemours And Company Manufacture of 1,1,1,2-tetrafluoroethane
EP0402652A1 (en) * 1989-06-13 1990-12-19 Atochem North America, Inc. Gas phase catalytic process for production of vinylidene fluoride
US5155082A (en) * 1991-04-12 1992-10-13 Allied-Signal Inc. Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons
US5177271A (en) * 1992-04-30 1993-01-05 Elf Atochem North America, Inc. Production of vinylidene fluoride
FR2690687A1 (fr) * 1992-04-30 1993-11-05 Atochem North America Elf Procédé de production de fluorure de vinylidène.
EP0594859A1 (en) * 1991-11-27 1994-05-04 Daikin Industries, Ltd. Production of 1,1,1-trifluoro-2-chloroethane and/or 1,1,1,2-tetrafluoroethane
US5475167A (en) * 1995-02-17 1995-12-12 E. I. Du Pont De Nemours And Company Process for the manufacture of pentafluoroethane
US5523497A (en) * 1992-05-04 1996-06-04 Bayer Aktiengesellschaft Process for preparing hexafluorochlorobutenes
US5654494A (en) * 1995-08-18 1997-08-05 Alliedsignal Inc. Process for the manufacture of 1,1,1,2-tetrafluoroethane
GB2313118A (en) * 1996-05-13 1997-11-19 Atochem Elf Sa Synthesis of 1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3-pentafluoropropane
WO1998033755A1 (en) * 1997-01-31 1998-08-06 E.I. Du Pont De Nemours And Company The catalytic manufacture of pentafluoropropenes
EP0877009A1 (en) * 1995-12-29 1998-11-11 Daikin Industries, Limited Process for producing 1,1,1,3,3-pentafluoropropane
US5856593A (en) * 1994-08-08 1999-01-05 Imperial Chemical Industries Plc Process for the production of fluorine containing olefins
WO1999051553A1 (en) * 1998-04-03 1999-10-14 E.I. Du Pont De Nemours And Company Process for the production of fluorocarbons
EP1038858A1 (en) * 1997-12-12 2000-09-27 Daikin Industries, Limited Process for the preparation of pentafluoroethane, fluorination catalysts and process for the preparation thereof

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USRE29534E (en) * 1972-08-18 1978-02-07 E. I. Du Pont De Nemours And Company Purification of perfluorosulfonyl fluoride perfluorovinyl ethers by thermal decomposition of unstable isomers
DE3729106A1 (de) * 1987-09-01 1989-03-09 Hoechst Ag Verfahren zur gewinnung von reinem tetrafluorethylen

Patent Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD43244A (cs) *
US2413695A (en) * 1943-06-19 1947-01-07 Kinetic Chemicals Inc Fluorinated compounds and pyrolytic methods for preparing them
US2627529A (en) * 1947-10-23 1953-02-03 Socony Vacuum Oil Co Inc Pyrolysis of difluoromonochloroethane
GB1039468A (en) * 1962-07-25 1966-08-17 Pechiney Saint Gobain Improvements in and relating to the preparation of vinylidene fluoride
US4613709A (en) * 1984-08-20 1986-09-23 Solvay & Cie. Process for the pyrolytic dehydrochlorination of haloalkanes in the presence of an initiator based on chlorinated product and the initiator employed in such a process
WO1990008755A1 (en) * 1989-02-03 1990-08-09 E.I. Du Pont De Nemours And Company Manufacture of 1,1,1,2-tetrafluoroethane
EP0402652A1 (en) * 1989-06-13 1990-12-19 Atochem North America, Inc. Gas phase catalytic process for production of vinylidene fluoride
US5155082A (en) * 1991-04-12 1992-10-13 Allied-Signal Inc. Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons
EP0594859A1 (en) * 1991-11-27 1994-05-04 Daikin Industries, Ltd. Production of 1,1,1-trifluoro-2-chloroethane and/or 1,1,1,2-tetrafluoroethane
FR2690687A1 (fr) * 1992-04-30 1993-11-05 Atochem North America Elf Procédé de production de fluorure de vinylidène.
US5177271A (en) * 1992-04-30 1993-01-05 Elf Atochem North America, Inc. Production of vinylidene fluoride
US5523497A (en) * 1992-05-04 1996-06-04 Bayer Aktiengesellschaft Process for preparing hexafluorochlorobutenes
US5856593A (en) * 1994-08-08 1999-01-05 Imperial Chemical Industries Plc Process for the production of fluorine containing olefins
US5475167A (en) * 1995-02-17 1995-12-12 E. I. Du Pont De Nemours And Company Process for the manufacture of pentafluoroethane
US5654494A (en) * 1995-08-18 1997-08-05 Alliedsignal Inc. Process for the manufacture of 1,1,1,2-tetrafluoroethane
EP0877009A1 (en) * 1995-12-29 1998-11-11 Daikin Industries, Limited Process for producing 1,1,1,3,3-pentafluoropropane
GB2313118A (en) * 1996-05-13 1997-11-19 Atochem Elf Sa Synthesis of 1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3-pentafluoropropane
WO1998033755A1 (en) * 1997-01-31 1998-08-06 E.I. Du Pont De Nemours And Company The catalytic manufacture of pentafluoropropenes
EP1038858A1 (en) * 1997-12-12 2000-09-27 Daikin Industries, Limited Process for the preparation of pentafluoroethane, fluorination catalysts and process for the preparation thereof
WO1999051553A1 (en) * 1998-04-03 1999-10-14 E.I. Du Pont De Nemours And Company Process for the production of fluorocarbons

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
CHEMICAL AND PHYSICAL PROCESSES IN COMBUSTION (1996) 507-510 *
COMBUSTION SCIENCE AND TECHNOLOGY (1996), 116-117(1-6), 5-30 *
DATABASE BEILSTEIN [online] accession no. rid 175786 *
DATABASE BEILSTEIN [online] accession no. rid 1856358 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; DIFELICE, JOHN J. ET AL: "Thermal reactions of 2-chloro-1,1,1,2-tetrafluoroethane", XP002220687, retrieved from STN Database accession no. 126:117682 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SALMON, ROBERT P. ET AL: "Experimental flow tube study on pyrolysis of 2-chloro-1,1,1-trifluoroethane", XP002220688, retrieved from STN Database accession no. 126:131133 *
See also references of WO0107384A1 *

Also Published As

Publication number Publication date
EP1198441A1 (en) 2002-04-24
KR20020029086A (ko) 2002-04-17
CZ2002183A3 (cs) 2002-11-13
AU6359400A (en) 2001-02-13
PL352765A1 (en) 2003-09-08
CN1361758A (zh) 2002-07-31
WO2001007384A1 (en) 2001-02-01
CN1258505C (zh) 2006-06-07
JP2003505439A (ja) 2003-02-12
BR0012650A (pt) 2002-04-09
CA2380285A1 (en) 2001-02-01

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