ES2654159T3 - Método para preparar cis-hexafluoro-2-buteno - Google Patents
Método para preparar cis-hexafluoro-2-buteno Download PDFInfo
- Publication number
- ES2654159T3 ES2654159T3 ES11759913.4T ES11759913T ES2654159T3 ES 2654159 T3 ES2654159 T3 ES 2654159T3 ES 11759913 T ES11759913 T ES 11759913T ES 2654159 T3 ES2654159 T3 ES 2654159T3
- Authority
- ES
- Spain
- Prior art keywords
- hexafluoro
- butene
- cis
- reaction
- facilitate
- 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.)
- Active
Links
- 239000003054 catalyst Substances 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract description 10
- 239000013110 organic ligand Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 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 abstract description 3
- 238000003682 fluorination reaction Methods 0.000 abstract description 3
- NLOLSXYRJFEOTA-UPHRSURJSA-N (z)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C/C(F)(F)F NLOLSXYRJFEOTA-UPHRSURJSA-N 0.000 abstract 3
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 11
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 11
- 229940045803 cuprous chloride Drugs 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229960002089 ferrous chloride Drugs 0.000 description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 2
- PREWBNUKNNTMHC-UHFFFAOYSA-N 2-chloro-1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)CC(Cl)C(F)(F)F PREWBNUKNNTMHC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- -1 Hexamethylene phosphamide Chemical compound 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JMLPVHXESHXUSV-UHFFFAOYSA-N dodecane-1,1-diamine Chemical compound CCCCCCCCCCCC(N)N JMLPVHXESHXUSV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- 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
- 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
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
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)
- Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31787910P | 2010-03-26 | 2010-03-26 | |
| US317879P | 2010-03-26 | ||
| US201113045926 | 2011-03-11 | ||
| US13/045,926 US8461401B2 (en) | 2010-03-26 | 2011-03-11 | Method for making hexafluoro-2-butene |
| PCT/US2011/028476 WO2011119370A2 (en) | 2010-03-26 | 2011-03-15 | Method for making hexafluoro-2-butene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2654159T3 true ES2654159T3 (es) | 2018-02-12 |
Family
ID=44657198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11759913.4T Active ES2654159T3 (es) | 2010-03-26 | 2011-03-15 | Método para preparar cis-hexafluoro-2-buteno |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8461401B2 (https=) |
| EP (1) | EP2552873B1 (https=) |
| JP (3) | JP5913279B2 (https=) |
| CN (1) | CN102884030B (https=) |
| ES (1) | ES2654159T3 (https=) |
| MX (1) | MX2012011055A (https=) |
| WO (1) | WO2011119370A2 (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2968009B1 (fr) | 2010-11-25 | 2012-11-16 | Arkema France | Fluides frigorigenes contenant du (e)-1,1,1,4,4,4-hexafluorobut-2-ene |
| EP3543311B1 (en) | 2010-11-25 | 2022-11-09 | Arkema France | Use of compositions of chloro-trifluoropropene and hexafluorobutene |
| FR2968310B1 (fr) | 2010-12-03 | 2012-12-07 | Arkema France | Compositions a base de 1,1,1,4,4,4-hexafluorobut-2-ene et de 3,3,4,4,4-pentafluorobut-1-ene |
| FR2977256B1 (fr) | 2011-07-01 | 2013-06-21 | Arkema France | Compositions de 2,4,4,4-tetrafluorobut-1-ene et de cis-1,1,1,4,4,4-hexafluorobut-2-ene |
| CN103917507A (zh) * | 2011-10-24 | 2014-07-09 | 纳幕尔杜邦公司 | 制备氢单氯氟丁烷和氢单氯氟戊烷化合物的催化方法 |
| JP5790438B2 (ja) * | 2011-11-21 | 2015-10-07 | セントラル硝子株式会社 | トランス−１−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
| FR2989084B1 (fr) | 2012-04-04 | 2015-04-10 | Arkema France | Compositions a base de 2,3,3,4,4,4-hexafluorobut-1-ene |
| FR2989374A1 (fr) * | 2012-04-11 | 2013-10-18 | Arkema France | Procede de preparation d'un compose olefinique sous forme d'un isomere specifique. |
| US9234123B2 (en) * | 2013-03-21 | 2016-01-12 | Hsi Fire & Safety Group, Llc | Compositions for totally non-flammable aerosol dusters |
| US20170015607A1 (en) * | 2014-03-21 | 2017-01-19 | The Chemours Company Fc, Llc | Processes for the production of z 1,1,1,4,4,4 hexafluoro 2-butene |
| US9353030B2 (en) * | 2014-07-25 | 2016-05-31 | Honeywell International Inc. | One-step process for hexafluoro-2-butene |
| CN104447186B (zh) * | 2014-11-20 | 2016-08-17 | 西安近代化学研究所 | 一种2,4,4-三氯-1,1,1-三氟丁烷的制备方法 |
| CN104370690B (zh) * | 2014-11-20 | 2016-08-17 | 西安近代化学研究所 | 一种反式-1,1,1,4,4,4-六氟-2-丁烯的合成方法 |
| 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 |
| MX2018001489A (es) | 2015-08-07 | 2018-04-24 | Chemours Co Fc Llc | Isomerizacion catalitica de z-1,1,14,4,4,-hexafluoro-2-buteno a e-1,1,1,4,4,4-hexafluoro-2-buteno. |
| KR102716246B1 (ko) * | 2016-01-22 | 2024-10-11 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 폴리아이소시아네이트/활성 수소-함유 화합물 반응 생성물의 발포 |
| JP6995108B2 (ja) * | 2016-07-27 | 2022-02-21 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | ハロゲン化オレフィンを製造するための方法 |
| WO2019051390A1 (en) | 2017-09-11 | 2019-03-14 | The Chemours Company, Fc, Llc | AZEOTROPIC COMPOSITIONS COMPRISING HYDROGEN FLUORIDE AND FLUOROCARBONS |
| JP7270609B2 (ja) * | 2017-09-11 | 2023-05-10 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | （ｅ）－１，１，１，４，４，４－ヘキサフルオロブタ－２－エンを調製するための液相プロセス |
| CN107759440B (zh) * | 2017-11-07 | 2020-07-03 | 中国民航大学 | 一种将含氟烯烃双键上的氟置换成氢的方法 |
| CA3083919C (en) * | 2017-12-04 | 2022-07-26 | The Chemours Company Fc, Llc | Process for preparing 1,1,3-trichloro-4,4,4-trifluorobut-1-ene via catalysis in the absence of hydrogen fluoride (hf) |
| CN109678650A (zh) * | 2018-12-25 | 2019-04-26 | 西安近代化学研究所 | 一种1,1,1,3-四氯-4,4,4-三氟丁烷的制备方法 |
| CN110590496A (zh) * | 2019-09-24 | 2019-12-20 | 浙江三美化工股份有限公司 | 一种气相连续合成顺式-1,1,1,4,4,4-六氟-2-丁烯的方法 |
| KR20220131950A (ko) | 2020-01-23 | 2022-09-29 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | (e)-1,1,1,4,5,5,5-헵타플루오로-4-(트라이플루오로메틸)펜트-2-엔의 합성 |
| JP7697960B2 (ja) | 2020-03-04 | 2025-06-24 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | （ｚ）－１，１，１，４，４，４－ヘキサフルオロ－２－ブテン及び中間体を生成するためのプロセス |
| CN112159301B (zh) * | 2020-09-29 | 2022-12-13 | 西安近代化学研究所 | 一种2-氯-1,1,1,4,4,4-六氟-2-丁烯的合成方法 |
| US20230373887A1 (en) * | 2020-10-15 | 2023-11-23 | Resonac Corporation | Method for storing fluorobutene |
| KR102924118B1 (ko) * | 2020-10-15 | 2026-02-09 | 가부시끼가이샤 레조낙 | 플루오로부텐의 보관 방법 |
| KR102924126B1 (ko) * | 2020-10-15 | 2026-02-06 | 가부시끼가이샤 레조낙 | 플루오로-2-부텐의 보관 방법 |
| JPWO2022080272A1 (https=) * | 2020-10-15 | 2022-04-21 | ||
| CN116472258A (zh) * | 2020-10-15 | 2023-07-21 | 株式会社力森诺科 | 氟-2-丁烯的保存方法 |
| JPWO2022080275A1 (https=) * | 2020-10-15 | 2022-04-21 | ||
| WO2022085544A1 (ja) * | 2020-10-22 | 2022-04-28 | Ａｇｃ株式会社 | 電気設備 |
| CN114716297B (zh) * | 2021-01-06 | 2023-10-27 | 浙江省化工研究院有限公司 | 一种e-1,1,1,4,4,4-六氟-2-丁烯的制备方法 |
| CN114292158B (zh) * | 2021-12-01 | 2024-01-02 | 西安近代化学研究所 | 一种制备顺式-1,1,1,4,4,4-六氟-2-丁烯的方法 |
| KR102788759B1 (ko) | 2022-05-13 | 2025-04-01 | (주)후성 | 1,1,1,4,4,4-헥사플루오로-2-부텐의 제조방법 |
| CN116037117B (zh) * | 2023-03-31 | 2023-07-25 | 北京宇极科技发展有限公司 | 引发剂、氟化催化剂和e-1,3,3,3-四氟丙烯与z-1,3,3,3-四氟丙烯的制备方法 |
| CN116037120B (zh) * | 2023-03-31 | 2023-07-14 | 北京宇极科技发展有限公司 | 1,1,1,4,4,4-六氟-2-丁烯的正反异构体的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210340A (en) | 1987-07-30 | 1993-05-11 | Bayer Aktiengesellschaft | Preparation of polyfluorobutenes |
| DE4213975A1 (de) * | 1992-04-29 | 1993-11-04 | Bayer Ag | Verfahren zur herstellung von hexafluorbutan und dabei zugaengliche zwischenprodukte |
| US5516951A (en) | 1992-11-20 | 1996-05-14 | Daikin Industries Ltd. | Process for preparing 1,1,1,4,4,4-hexafluoro-2-butene and 1,1,1,4,4,4-hexafluorobutane |
| JP3304468B2 (ja) | 1993-01-29 | 2002-07-22 | ダイキン工業株式会社 | １，１，１，４，４，４−ヘキサフルオロ−２−ブテン類及び１，１，１，４，４，４−ヘキサフルオロブタンの製造方法 |
| DE4305163A1 (de) * | 1993-02-19 | 1994-08-25 | Bayer Ag | Verfahren zur Herstellung von Hexafluorbuten |
| JP4724997B2 (ja) * | 2000-02-02 | 2011-07-13 | ダイキン工業株式会社 | 含水素フッ素化炭化水素の製造方法 |
| JP2003015619A (ja) | 2001-06-28 | 2003-01-17 | Pioneer Electronic Corp | 画像処理装置、画像処理方法およびコンピュータ読み取り可能な記録媒体 |
| US20030028057A1 (en) * | 2001-07-20 | 2003-02-06 | Stephen Owens | Methods and materials for the preparation and purification of halogenated hydrocarbons |
| US20050177012A1 (en) * | 2001-07-20 | 2005-08-11 | Pcbu Services, Inc. | Halocarbon production processes, halocarbon separation processes, and halocarbon separation systems |
| US7897823B2 (en) | 2004-10-29 | 2011-03-01 | E. I. Du Pont De Nemours And Company | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes |
| CA2629356A1 (en) * | 2005-11-10 | 2007-05-24 | Great Lakes Chemical Corporation | Compositions ,combustion prevention compositions, methods for preventing and/or extinguishing combustion, combustion prevention systems, and production processes |
| CN101578252B (zh) * | 2006-09-05 | 2013-11-27 | 纳幕尔杜邦公司 | 1,2,3,3,3-五氟丙烯生产方法 |
| US8063257B2 (en) * | 2007-01-03 | 2011-11-22 | Honeywell International Inc. | Method for producing 2,3,3,3-tetrafluoropropene |
| WO2009117458A2 (en) | 2008-03-19 | 2009-09-24 | E. I. Du Pont De Nemours And Company | Process for making 1,1,1,4,4,4-hexafluoro-2-butene |
| JP5439739B2 (ja) * | 2008-05-12 | 2014-03-12 | 日本ゼオン株式会社 | 含フッ素アルケン化合物とその製造方法 |
| EP2310347A4 (en) * | 2008-07-31 | 2012-10-31 | Honeywell Int Inc | PROCESS FOR THE PREPARATION OF PERFLUORATED CIS-ALKEN |
| US8426655B2 (en) * | 2010-03-26 | 2013-04-23 | Honeywell International Inc. | Process for the manufacture of hexafluoro-2-butene |
-
2011
- 2011-03-11 US US13/045,926 patent/US8461401B2/en active Active
- 2011-03-15 ES ES11759913.4T patent/ES2654159T3/es active Active
- 2011-03-15 WO PCT/US2011/028476 patent/WO2011119370A2/en not_active Ceased
- 2011-03-15 MX MX2012011055A patent/MX2012011055A/es active IP Right Grant
- 2011-03-15 JP JP2013501301A patent/JP5913279B2/ja active Active
- 2011-03-15 CN CN201180016420.3A patent/CN102884030B/zh active Active
- 2011-03-15 EP EP11759913.4A patent/EP2552873B1/en active Active
-
2015
- 2015-10-16 JP JP2015204460A patent/JP6088618B2/ja active Active
-
2017
- 2017-02-03 JP JP2017018610A patent/JP2017125023A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN102884030B (zh) | 2015-11-25 |
| WO2011119370A2 (en) | 2011-09-29 |
| JP2016034970A (ja) | 2016-03-17 |
| US20110237844A1 (en) | 2011-09-29 |
| JP5913279B2 (ja) | 2016-04-27 |
| EP2552873A4 (en) | 2014-09-10 |
| CN102884030A (zh) | 2013-01-16 |
| WO2011119370A3 (en) | 2011-12-22 |
| EP2552873B1 (en) | 2017-10-18 |
| JP6088618B2 (ja) | 2017-03-01 |
| EP2552873A2 (en) | 2013-02-06 |
| MX2012011055A (es) | 2013-01-28 |
| JP2017125023A (ja) | 2017-07-20 |
| JP2013523637A (ja) | 2013-06-17 |
| US8461401B2 (en) | 2013-06-11 |
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