JP2019523263A5 - - Google Patents
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- Publication number
- JP2019523263A5 JP2019523263A5 JP2019503744A JP2019503744A JP2019523263A5 JP 2019523263 A5 JP2019523263 A5 JP 2019523263A5 JP 2019503744 A JP2019503744 A JP 2019503744A JP 2019503744 A JP2019503744 A JP 2019503744A JP 2019523263 A5 JP2019523263 A5 JP 2019523263A5
- Authority
- JP
- Japan
- Prior art keywords
- ccl
- haloalkane
- olefin
- chcl
- fluorination
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 19
- 150000001350 alkyl halides Chemical class 0.000 claims 11
- 238000003682 fluorination reaction Methods 0.000 claims 8
- 150000001336 alkenes Chemical class 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 6
- 238000003780 insertion Methods 0.000 claims 5
- 230000037431 insertion Effects 0.000 claims 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 3
- 229910018287 SbF 5 Inorganic materials 0.000 claims 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910000423 chromium oxide Inorganic materials 0.000 claims 1
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662367412P | 2016-07-27 | 2016-07-27 | |
| US62/367,412 | 2016-07-27 | ||
| PCT/US2017/043497 WO2018022500A1 (en) | 2016-07-27 | 2017-07-24 | Process for producing halogenated olefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019523263A JP2019523263A (ja) | 2019-08-22 |
| JP2019523263A5 true JP2019523263A5 (enExample) | 2020-09-03 |
| JP6995108B2 JP6995108B2 (ja) | 2022-02-21 |
Family
ID=59416872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019503744A Active JP6995108B2 (ja) | 2016-07-27 | 2017-07-24 | ハロゲン化オレフィンを製造するための方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11731925B2 (enExample) |
| EP (1) | EP3490964B1 (enExample) |
| JP (1) | JP6995108B2 (enExample) |
| CN (1) | CN109476567B (enExample) |
| ES (1) | ES2891525T3 (enExample) |
| WO (1) | WO2018022500A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021150801A1 (en) | 2020-01-23 | 2021-07-29 | The Chemours Company Fc, Llc | Synthesis of (e)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene |
| US12286386B2 (en) | 2020-03-04 | 2025-04-29 | The Chemours Company Fc, Llc | Process to produce (Z)-1,1,1,4,4,4-hexafluoro-2-butene and intermediates |
| CN116265097B (zh) * | 2021-12-17 | 2024-10-08 | 中国科学院宁波材料技术与工程研究所 | 用于气固相反应连续生产1,1,1,3-四氯丙烷的催化剂、其制备方法与应用 |
| WO2024163379A1 (en) | 2023-01-30 | 2024-08-08 | The Chemours Company Fc, Llc | Co-production of 1,1,1-trifluoropropene (1243zf) and e-1,1,1,4,4,4-hexafluoro-2-butene (e-1336mzz) |
| CN116037119B (zh) * | 2023-03-31 | 2023-07-07 | 北京宇极科技发展有限公司 | 引发剂、氟化催化剂、气相连续反应制备氢氟烯烃的方法 |
| WO2025096368A2 (en) | 2023-10-30 | 2025-05-08 | The Chemours Company Fc, Llc | Compositions comprising 1,3,3,3-tetrafluoropropene, methods of making same, and uses thereof |
| TW202528277A (zh) | 2023-10-30 | 2025-07-16 | 美商科慕Ｆｃ有限責任公司 | 包含１，３，３，３－四氟丙烯的組成物、其製造方法、及其用途 |
| WO2025160054A2 (en) | 2024-01-22 | 2025-07-31 | The Chemours Company Fc, Llc | Synthesis of 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258500A (en) | 1959-08-17 | 1966-06-28 | Du Pont | Process for fluorinating halohydro-carbons |
| US3528500A (en) | 1969-02-24 | 1970-09-15 | Joe R Brown | Tubing anchor |
| JPS5929042B2 (ja) * | 1975-07-09 | 1984-07-18 | 株式会社トクヤマ | パ−ハロゲン化アルカンとオレフイン類との付加反応方法 |
| JPS58146567A (ja) | 1982-02-25 | 1983-09-01 | Agency Of Ind Science & Technol | イオノフオアとして有用なポリエ−テル誘導体 |
| US4828818A (en) | 1987-03-13 | 1989-05-09 | Allied-Signal Inc. | Chromium aerogel method of producing same and fluorinating process utilizing same |
| US5036036A (en) | 1989-06-13 | 1991-07-30 | E. I. Du Pont De Nemours And Company | Chromium oxide catalyst composition |
| FR2669022B1 (fr) | 1990-11-13 | 1992-12-31 | Atochem | Procede de fabrication du tetrafluoro-1,1,1,2-ethane. |
| US6755942B1 (en) | 1995-08-01 | 2004-06-29 | E. I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons and selected compounds and azeotropes with HF |
| KR100516407B1 (ko) * | 1995-08-01 | 2005-09-27 | 이.아이,듀우판드네모아앤드캄파니 | 할로카본의 제조 방법, 선택된 화합물 및 ｈｆ 함유 공비조성물 |
| US6187978B1 (en) * | 1999-05-12 | 2001-02-13 | Alliedsignal Inc. | Continuous process for manufacturing halogenated compounds |
| WO2008030442A1 (en) * | 2006-09-05 | 2008-03-13 | E. I. Du Pont De Nemours And Company | Processes for producing 1,2,3,3,3-pentafluoropropene and precursors thereof |
| WO2009085862A1 (en) | 2007-12-19 | 2009-07-09 | Occidental Chemical Corporation | Methods of making chlorinated hydrocarbons |
| CN102405202B (zh) | 2009-04-23 | 2015-02-11 | 大金工业株式会社 | 制备2-氯-3,3,3-三氟丙烯的方法 |
| WO2010131766A2 (en) * | 2009-05-13 | 2010-11-18 | Daikin Industries, Ltd. | Process for preparing chlorine-containing fluorocarbon compound |
| US8461401B2 (en) * | 2010-03-26 | 2013-06-11 | Honeywell International Inc. | Method for making hexafluoro-2-butene |
| US8604257B2 (en) * | 2010-05-21 | 2013-12-10 | Honeywell International Inc. | Process for the preparation of fluorinated cis-alkene |
| RU2010147002A (ru) * | 2010-11-17 | 2012-05-27 | Е.И.Дюпон де Немур энд Компани (US) | Каталитический синтез галогенированных углеводородов |
| RU2010147004A (ru) | 2010-11-17 | 2012-05-27 | Е.И.Дюпон де Немур энд Компани (US) | Каталитический синтез внутренних фторбутенов и внутренних фторпентенов |
| CN106795071A (zh) * | 2014-08-12 | 2017-05-31 | 科慕埃弗西有限公司 | 用于制备支链氟烷基烯烃的方法 |
| US9896400B2 (en) * | 2014-10-16 | 2018-02-20 | Spolek Pro Chemickou A Hutni Vyrobu A.S. | Process for producing a chlorinated C3-6 alkane |
| CN104529695B (zh) * | 2015-01-26 | 2016-06-22 | 杭州芳环科技有限公司 | 一种制备1,1,1,4,4,4-六氟-2-丁烯的方法 |
-
2017
- 2017-07-24 US US16/320,320 patent/US11731925B2/en active Active
- 2017-07-24 JP JP2019503744A patent/JP6995108B2/ja active Active
- 2017-07-24 EP EP17745637.3A patent/EP3490964B1/en active Active
- 2017-07-24 ES ES17745637T patent/ES2891525T3/es active Active
- 2017-07-24 WO PCT/US2017/043497 patent/WO2018022500A1/en not_active Ceased
- 2017-07-24 CN CN201780046290.5A patent/CN109476567B/zh active Active
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