CA2987113A1 - Method for producing fluorinated olefins - Google Patents
Method for producing fluorinated olefinsInfo
- Publication number
- CA2987113A1 CA2987113A1 CA2987113A CA2987113A CA2987113A1 CA 2987113 A1 CA2987113 A1 CA 2987113A1 CA 2987113 A CA2987113 A CA 2987113A CA 2987113 A CA2987113 A CA 2987113A CA 2987113 A1 CA2987113 A1 CA 2987113A1
- Authority
- CA
- Canada
- Prior art keywords
- reactant
- catalyst
- fhc
- reaction
- proviso
- 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
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000376 reactant Substances 0.000 claims abstract description 126
- 238000000034 method Methods 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 150000004820 halides Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 1
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006578 reductive coupling reaction Methods 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 238000010485 C−C bond formation reaction Methods 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- -1 extinguishers Substances 0.000 description 1
- 235000019000 fluorine Nutrition 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07C17/26—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
-
- 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
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562170716P | 2015-06-04 | 2015-06-04 | |
| US62/170,716 | 2015-06-04 | ||
| PCT/US2016/035140 WO2016196538A1 (en) | 2015-06-04 | 2016-06-01 | Method for producing fluorinated olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2987113A1 true CA2987113A1 (en) | 2016-12-08 |
Family
ID=57441881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2987113A Abandoned CA2987113A1 (en) | 2015-06-04 | 2016-06-01 | Method for producing fluorinated olefins |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10259761B2 (OSRAM) |
| EP (1) | EP3303273A4 (OSRAM) |
| JP (1) | JP2018516268A (OSRAM) |
| KR (1) | KR20180015646A (OSRAM) |
| CN (1) | CN107614468A (OSRAM) |
| CA (1) | CA2987113A1 (OSRAM) |
| MX (1) | MX2017015568A (OSRAM) |
| WO (1) | WO2016196538A1 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106833536B (zh) * | 2016-12-26 | 2019-08-20 | 浙江衢化氟化学有限公司 | 一种含有氢氟烯烃的制冷剂组合物 |
| JP7287965B2 (ja) * | 2019-11-13 | 2023-06-06 | フジアン ヨンジン テクノロジー カンパニー リミテッド | ２，３，３，３－テトラフルオロプロペン（１２３４ｙｆ）および２，３－ジクロロ－１，１，１－トリフルオロプロパン（２４３ｄｂ）の新しい合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL264123A (OSRAM) | 1960-04-28 | |||
| EP0334796B1 (de) | 1988-03-19 | 1993-05-12 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von ungesättigten halogenierten Kohlenwasserstoffen |
| JP3008510B2 (ja) * | 1991-02-16 | 2000-02-14 | ダイキン工業株式会社 | 含フッ素エタンの２量体の製法 |
| DE4416326A1 (de) * | 1994-05-09 | 1995-11-16 | Bayer Ag | Verfahren zur Herstellung von Hexafluor-C¶4¶-Verbindungen |
| JP2003505439A (ja) * | 1999-07-21 | 2003-02-12 | ヘイロウカーボン プロダクツ コーポレイション | 脂肪族フルオロカーボンの製法 |
| US6806396B2 (en) * | 2001-12-18 | 2004-10-19 | E. I. Du Pont De Nemours And Company | Disposal of fluoroform (HFC-23) |
| CN1968915B (zh) * | 2004-04-29 | 2011-08-03 | 霍尼韦尔国际公司 | 1,3,3,3-四氟丙烯的合成方法 |
| US7135601B2 (en) | 2005-03-28 | 2006-11-14 | Honeywell International Inc. | Catalytic method for the production of fluoroalkylenes from chlorofluorohydrocarbons |
| JP5416587B2 (ja) * | 2006-10-03 | 2014-02-12 | メキシケム、アマンコ、ホールディング、ソシエダッド、アノニマ、デ、カピタル、バリアブレ | プロセス |
| KR20140097148A (ko) * | 2011-11-04 | 2014-08-06 | 셀마 벡터세빅 | 2,3,3,3-테트라플루오로프로펜의 제조 방법 |
| CN104045508B (zh) * | 2014-06-09 | 2016-05-18 | 巨化集团技术中心 | 同时制备三氟氯乙烯和四氟乙烯的方法 |
-
2016
- 2016-06-01 WO PCT/US2016/035140 patent/WO2016196538A1/en not_active Ceased
- 2016-06-01 US US15/571,079 patent/US10259761B2/en not_active Expired - Fee Related
- 2016-06-01 EP EP16804273.7A patent/EP3303273A4/en not_active Withdrawn
- 2016-06-01 JP JP2017562650A patent/JP2018516268A/ja active Pending
- 2016-06-01 CA CA2987113A patent/CA2987113A1/en not_active Abandoned
- 2016-06-01 MX MX2017015568A patent/MX2017015568A/es unknown
- 2016-06-01 KR KR1020177034900A patent/KR20180015646A/ko not_active Withdrawn
- 2016-06-01 CN CN201680032241.1A patent/CN107614468A/zh not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180015646A (ko) | 2018-02-13 |
| EP3303273A1 (en) | 2018-04-11 |
| EP3303273A4 (en) | 2019-01-23 |
| CN107614468A (zh) | 2018-01-19 |
| MX2017015568A (es) | 2018-04-26 |
| US20180162795A1 (en) | 2018-06-14 |
| JP2018516268A (ja) | 2018-06-21 |
| US10259761B2 (en) | 2019-04-16 |
| WO2016196538A1 (en) | 2016-12-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20220823 |
|
| FZDE | Discontinued |
Effective date: 20220823 |