CA2380285A1 - Production of aliphatic fluorocarbons - Google Patents
Production of aliphatic fluorocarbons Download PDFInfo
- Publication number
- CA2380285A1 CA2380285A1 CA002380285A CA2380285A CA2380285A1 CA 2380285 A1 CA2380285 A1 CA 2380285A1 CA 002380285 A CA002380285 A CA 002380285A CA 2380285 A CA2380285 A CA 2380285A CA 2380285 A1 CA2380285 A1 CA 2380285A1
- Authority
- CA
- Canada
- 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.)
- Abandoned
Links
- 125000001931 aliphatic group Chemical group 0.000 title claims description 35
- 238000004519 manufacturing process Methods 0.000 title claims description 30
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 21
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012048 reactive intermediate Substances 0.000 claims abstract description 13
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims abstract description 12
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims abstract description 10
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 7
- WSJULBMCKQTTIG-UHFFFAOYSA-N 1,1,1,2,3,4,4,4-octafluorobut-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)F WSJULBMCKQTTIG-UHFFFAOYSA-N 0.000 claims abstract description 5
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical group FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 claims abstract description 3
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 claims abstract 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 32
- 239000007858 starting material Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000000543 intermediate Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 3
- KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 claims description 2
- 229950003332 perflubutane Drugs 0.000 claims description 2
- 239000000047 product Substances 0.000 description 47
- 238000000197 pyrolysis Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- NLOLSXYRJFEOTA-OWOJBTEDSA-N (e)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C\C(F)(F)F NLOLSXYRJFEOTA-OWOJBTEDSA-N 0.000 description 2
- 241000972773 Aulopiformes Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 235000019515 salmon Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 description 1
- PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical compound FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
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 | |
| US60/144,739 | 1999-07-21 | ||
| PCT/US2000/019863 WO2001007384A1 (en) | 1999-07-21 | 2000-07-21 | Production of aliphatic fluorocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2380285A1 true CA2380285A1 (en) | 2001-02-01 |
Family
ID=22509912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002380285A Abandoned CA2380285A1 (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 |
| US7674939B2 (en) | 2004-04-29 | 2010-03-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US9024092B2 (en) | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| 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 |
| ES2543408T3 (es) * | 2004-04-29 | 2015-08-19 | Honeywell International Inc. | Procedimiento para síntesis de 1,3,3,3-tetrafluoropropeno |
| 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 |
| US9102579B2 (en) | 2004-04-29 | 2015-08-11 | 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 |
| 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 |
| US9884797B2 (en) * | 2014-12-11 | 2018-02-06 | Arkema France | Process for the preparation of 1-chloro-2,2-difluoroethane |
| EP3303273A4 (en) * | 2015-06-04 | 2019-01-23 | Arkema, Inc. | PROCESS FOR PREPARING FLUORINATED OLEFINES |
| 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 |
Family Cites Families (22)
| 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 |
| FR1337360A (fr) * | 1962-07-25 | 1963-09-13 | Pechiney Saint Gobain | Procédé d'obtention de fluorure de vinylidène |
| 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 |
| EP0172596B1 (fr) * | 1984-08-20 | 1988-02-03 | SOLVAY & Cie (Société Anonyme) | Procédé de déshydrochloration pyrolytique d'halogénoalcanes en présence d'un initiateur à base de produit chloré et initiateur utilisé dans un tel procédé |
| DE3729106A1 (de) * | 1987-09-01 | 1989-03-09 | Hoechst Ag | Verfahren zur gewinnung von reinem tetrafluorethylen |
| DE69023759T3 (de) * | 1989-02-03 | 2004-05-13 | E.I. Du Pont De Nemours And Co., Wilmington | Verfahren zur herstellung von 1,1,1,2-tetrafluoroäthan. |
| CA2016686A1 (en) * | 1989-06-13 | 1990-12-13 | Maher Y. Elsheikh | 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 |
| JP2661441B2 (ja) * | 1991-11-27 | 1997-10-08 | ダイキン工業株式会社 | １，１，１−トリフルオロ−２−クロロエタンおよび／または１，１，１，２−テトラフルオロエタンの製法 |
| US5177271A (en) * | 1992-04-30 | 1993-01-05 | Elf Atochem North America, Inc. | Production of vinylidene fluoride |
| FR2690687B1 (fr) * | 1992-04-30 | 1995-01-27 | Atochem North America Elf | Procédé de production de fluorure de vinylidène. |
| DE4214739A1 (de) * | 1992-05-04 | 1993-11-11 | Bayer Ag | Verfahren zur Herstellung von Hexafluorchlorbutenen |
| DK0775100T3 (da) * | 1994-08-08 | 2000-11-27 | Ici Plc | Fremgangsmåde til fremstilling af trifluorethylen |
| 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 |
| JP3818398B2 (ja) * | 1995-12-29 | 2006-09-06 | ダイキン工業株式会社 | １，１，１，３，３−ペンタフルオロプロパンの製造方法 |
| FR2748473B1 (fr) * | 1996-05-13 | 1998-07-24 | Atochem Elf Sa | Synthese du 1-chloro-3,3,3 trifluoropropene et sa fluoration en 1,1,1,3,3 pentafluoropropane |
| EP0958265B1 (en) * | 1997-01-31 | 2003-04-02 | E.I. Du Pont De Nemours And Company | The catalytic manufacture of pentafluoropropenes |
| JP3520900B2 (ja) * | 1997-12-12 | 2004-04-19 | ダイキン工業株式会社 | ペンタフルオロエタンの製造方法、並びにフッ素化用触媒及びその製造方法 |
| AU3378099A (en) * | 1998-04-03 | 1999-10-25 | E.I. Du Pont De Nemours And Company | Process for the production of fluorocarbons |
-
2000
- 2000-07-21 AU AU63594/00A patent/AU6359400A/en not_active Abandoned
- 2000-07-21 BR BR0012650-0A patent/BR0012650A/pt not_active IP Right Cessation
- 2000-07-21 EP EP00950495A patent/EP1198441A4/en not_active Withdrawn
- 2000-07-21 CA CA002380285A patent/CA2380285A1/en not_active Abandoned
- 2000-07-21 PL PL00352765A patent/PL352765A1/xx not_active Application Discontinuation
- 2000-07-21 CZ CZ2002183A patent/CZ2002183A3/cs unknown
- 2000-07-21 CN CNB008106355A patent/CN1258505C/zh not_active Expired - Fee Related
- 2000-07-21 WO PCT/US2000/019863 patent/WO2001007384A1/en not_active Application Discontinuation
- 2000-07-21 KR KR1020027000863A patent/KR20020029086A/ko not_active Application Discontinuation
- 2000-07-21 JP JP2001512473A patent/JP2003505439A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1361758A (zh) | 2002-07-31 |
| AU6359400A (en) | 2001-02-13 |
| BR0012650A (pt) | 2002-04-09 |
| KR20020029086A (ko) | 2002-04-17 |
| CZ2002183A3 (cs) | 2002-11-13 |
| PL352765A1 (en) | 2003-09-08 |
| CN1258505C (zh) | 2006-06-07 |
| WO2001007384A1 (en) | 2001-02-01 |
| EP1198441A4 (en) | 2003-01-22 |
| JP2003505439A (ja) | 2003-02-12 |
| EP1198441A1 (en) | 2002-04-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |