EP1198441A4 - PRODUCTION OF ALIPHATIC FLUOROCARBONS - Google Patents
PRODUCTION OF ALIPHATIC FLUOROCARBONSInfo
- 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- Withdrawn
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)
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 (ja) |
JP (1) | JP2003505439A (ja) |
KR (1) | KR20020029086A (ja) |
CN (1) | CN1258505C (ja) |
AU (1) | AU6359400A (ja) |
BR (1) | BR0012650A (ja) |
CA (1) | CA2380285A1 (ja) |
CZ (1) | CZ2002183A3 (ja) |
PL (1) | PL352765A1 (ja) |
WO (1) | WO2001007384A1 (ja) |
Families Citing this family (16)
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 |
CN1972887B (zh) | 2004-04-29 | 2010-10-13 | 霍尼韦尔国际公司 | 1,3,3,3-四氟丙烯的合成方法 |
US8383867B2 (en) | 2004-04-29 | 2013-02-26 | 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 |
US7659434B2 (en) | 2004-04-29 | 2010-02-09 | 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 |
JP4864878B2 (ja) * | 2004-04-29 | 2012-02-01 | ハネウェル・インターナショナル・インコーポレーテッド | 1,3,3,3−テトラフルオロプロペンの合成法 |
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 |
US7674939B2 (en) | 2004-04-29 | 2010-03-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
WO2007056127A1 (en) * | 2005-11-03 | 2007-05-18 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
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 |
US9884797B2 (en) * | 2014-12-11 | 2018-02-06 | Arkema France | Process for the preparation of 1-chloro-2,2-difluoroethane |
CA2987113A1 (en) * | 2015-06-04 | 2016-12-08 | 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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD43244A (ja) * | ||||
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 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
2000
- 2000-07-21 CN CNB008106355A patent/CN1258505C/zh not_active Expired - Fee Related
- 2000-07-21 CZ CZ2002183A patent/CZ2002183A3/cs unknown
- 2000-07-21 BR BR0012650-0A patent/BR0012650A/pt not_active IP Right Cessation
- 2000-07-21 JP JP2001512473A patent/JP2003505439A/ja active Pending
- 2000-07-21 CA CA002380285A patent/CA2380285A1/en not_active Abandoned
- 2000-07-21 AU AU63594/00A patent/AU6359400A/en not_active Abandoned
- 2000-07-21 KR KR1020027000863A patent/KR20020029086A/ko not_active Application Discontinuation
- 2000-07-21 EP EP00950495A patent/EP1198441A4/en not_active Withdrawn
- 2000-07-21 PL PL00352765A patent/PL352765A1/xx not_active Application Discontinuation
- 2000-07-21 WO PCT/US2000/019863 patent/WO2001007384A1/en not_active Application Discontinuation
Patent Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD43244A (ja) * | ||||
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)
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 |
---|---|
PL352765A1 (en) | 2003-09-08 |
CN1361758A (zh) | 2002-07-31 |
JP2003505439A (ja) | 2003-02-12 |
CA2380285A1 (en) | 2001-02-01 |
CZ2002183A3 (cs) | 2002-11-13 |
EP1198441A1 (en) | 2002-04-24 |
AU6359400A (en) | 2001-02-13 |
KR20020029086A (ko) | 2002-04-17 |
BR0012650A (pt) | 2002-04-09 |
WO2001007384A1 (en) | 2001-02-01 |
CN1258505C (zh) | 2006-06-07 |
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