CA2719042A1 - Process for making 1,1,1,4,4,4-hexafluoro-2-butene - Google Patents
Process for making 1,1,1,4,4,4-hexafluoro-2-butene Download PDFInfo
- Publication number
- CA2719042A1 CA2719042A1 CA2719042A CA2719042A CA2719042A1 CA 2719042 A1 CA2719042 A1 CA 2719042A1 CA 2719042 A CA2719042 A CA 2719042A CA 2719042 A CA2719042 A CA 2719042A CA 2719042 A1 CA2719042 A1 CA 2719042A1
- Authority
- CA
- Canada
- Prior art keywords
- tube
- hcfc
- copper
- hexafluoro
- butene
- 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
- 238000000034 method Methods 0.000 title claims abstract description 41
- 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 title claims abstract description 10
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000010949 copper Substances 0.000 claims abstract description 23
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052802 copper Inorganic materials 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 150000001408 amides Chemical class 0.000 claims abstract description 16
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract description 13
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007791 liquid phase Substances 0.000 description 12
- 239000012808 vapor phase Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 9
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- -1 Cul Inorganic materials 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3784708P | 2008-03-19 | 2008-03-19 | |
| US61/037,847 | 2008-03-19 | ||
| PCT/US2009/037459 WO2009117458A2 (en) | 2008-03-19 | 2009-03-18 | Process for making 1,1,1,4,4,4-hexafluoro-2-butene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2719042A1 true CA2719042A1 (en) | 2009-09-24 |
Family
ID=40843928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2719042A Abandoned CA2719042A1 (en) | 2008-03-19 | 2009-03-18 | Process for making 1,1,1,4,4,4-hexafluoro-2-butene |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8436216B2 (enExample) |
| EP (2) | EP2260015B1 (enExample) |
| JP (1) | JP5341978B2 (enExample) |
| KR (1) | KR20110005815A (enExample) |
| CN (2) | CN102015592B (enExample) |
| BR (1) | BRPI0906249A2 (enExample) |
| CA (1) | CA2719042A1 (enExample) |
| ES (1) | ES2397588T3 (enExample) |
| MX (2) | MX2010010239A (enExample) |
| RU (1) | RU2476415C2 (enExample) |
| WO (1) | WO2009117458A2 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5266902B2 (ja) * | 2008-06-20 | 2013-08-21 | 日本ゼオン株式会社 | 含フッ素オレフィン化合物の製造方法 |
| JP5350901B2 (ja) * | 2009-06-12 | 2013-11-27 | Ａｇｃセイミケミカル株式会社 | テトラフルオロエチレン骨格を有する化合物の製造方法 |
| US8461401B2 (en) | 2010-03-26 | 2013-06-11 | Honeywell International Inc. | Method for making hexafluoro-2-butene |
| US8426655B2 (en) * | 2010-03-26 | 2013-04-23 | Honeywell International Inc. | Process for the manufacture of hexafluoro-2-butene |
| US8901360B2 (en) | 2010-05-21 | 2014-12-02 | Honeywell International Inc. | Process for cis 1,1,1,4,4,4-hexafluoro-2-butene |
| US8530709B2 (en) * | 2010-05-21 | 2013-09-10 | Honeywell International Inc. | Process for the production of fluorinated alkenes |
| US8604257B2 (en) | 2010-05-21 | 2013-12-10 | Honeywell International Inc. | Process for the preparation of fluorinated cis-alkene |
| TW201414823A (zh) * | 2012-09-19 | 2014-04-16 | Du Pont | 包含ｚ－１，１，１，４，４，４－六氟－２－丁烯及２，２－二氯－１，１，１－三氟乙烷之組合物及其使用方法 |
| SG10201703513WA (en) | 2012-10-30 | 2017-06-29 | Air Liquide | Fluorocarbon molecules for high aspect ratio oxide etch |
| US9748366B2 (en) | 2013-10-03 | 2017-08-29 | Applied Materials, Inc. | Etching oxide-nitride stacks using C4F6H2 |
| JP6570078B2 (ja) * | 2014-02-07 | 2019-09-04 | 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−ブテンを生成するための統合方法 |
| CN103755519A (zh) * | 2014-02-24 | 2014-04-30 | 山东联创节能新材料股份有限公司 | 六氟丁烯的合成方法 |
| CN106687430B (zh) * | 2014-03-21 | 2021-04-27 | 科慕埃弗西有限公司 | 生产z-1，1，1，4，4，4-六氟-2-丁烯的方法 |
| US9353030B2 (en) * | 2014-07-25 | 2016-05-31 | Honeywell International Inc. | One-step process for hexafluoro-2-butene |
| 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 |
| EP3253844B1 (en) | 2015-02-06 | 2022-06-22 | The Chemours Company FC, LLC | Compositions comprising z-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof |
| CN112920777A (zh) | 2015-02-06 | 2021-06-08 | 科慕埃弗西有限公司 | 包含e-1,1,1,4,4,4-六氟-2-丁烯的组合物及其用途 |
| WO2017027323A1 (en) | 2015-08-07 | 2017-02-16 | The Chemours Company Fc, Llc | Catalytic isomerization of z-1,1,1,4,4,4-hexafluoro-2-butene to e-1,1,1,4,4,4-hexafluoro-2-butene |
| CN106669837B (zh) * | 2015-11-06 | 2020-12-29 | 东莞东阳光科研发有限公司 | 一种制备1,1,1,4,4,4-六氟-2-丁烯的方法 |
| CN106925354B (zh) * | 2015-12-30 | 2020-04-17 | 浙江省化工研究院有限公司 | 一种用于制备卤代烯烃的液相催化剂 |
| CN106928017B (zh) * | 2015-12-30 | 2020-12-08 | 浙江省化工研究院有限公司 | 一种制备1,1,1,4,4,4-六氟-2-丁烯的方法 |
| CN107586251A (zh) * | 2017-07-26 | 2018-01-16 | 江苏蓝色星球环保科技股份有限公司 | 一种1，1，1，4，4，4‑六氟‑2‑丁烯的制备方法 |
| CN108359121B (zh) | 2017-12-14 | 2019-03-15 | 浙江衢化氟化学有限公司 | 一种共沸和类共沸组合物 |
| CN110396037B (zh) * | 2018-04-25 | 2022-04-15 | 浙江蓝天环保高科技股份有限公司 | 一种制备八氟-2-丁烯的方法 |
| CN109331864B (zh) * | 2018-10-26 | 2019-12-31 | 东莞东阳光科研发有限公司 | 一种氢化偶联催化剂及其制备方法及制备1,1,1,4,4,4-六氟-2-丁烯的方法 |
| WO2022085544A1 (ja) | 2020-10-22 | 2022-04-28 | Ａｇｃ株式会社 | 電気設備 |
| KR102788759B1 (ko) | 2022-05-13 | 2025-04-01 | (주)후성 | 1,1,1,4,4,4-헥사플루오로-2-부텐의 제조방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4634797A (en) * | 1985-02-07 | 1987-01-06 | Halocarbon Products Corporation | Coupling of chloroperfluoroalkanes |
| 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 |
| DE4214739A1 (de) | 1992-05-04 | 1993-11-11 | Bayer Ag | Verfahren zur Herstellung von Hexafluorchlorbutenen |
| WO1994012454A1 (fr) * | 1992-11-20 | 1994-06-09 | Daikin Industries, Ltd. | Procede de production de 1,1,1,4,4,4-hexafluoro-2-butene et de 1,1,1,4,4,4-hexafluorobutane |
| DE4416326A1 (de) * | 1994-05-09 | 1995-11-16 | Bayer Ag | Verfahren zur Herstellung von Hexafluor-C¶4¶-Verbindungen |
| EP0709357A1 (de) * | 1994-10-28 | 1996-05-01 | Hoechst Aktiengesellschaft | Verfahren zur Kreuzkupplung von aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten mit terminalen Alkinen |
| RU2210559C2 (ru) * | 1999-08-20 | 2003-08-20 | Институт элементоорганических соединений им.А.Н. Несмеянова РАН | Способ получения фторолефинов |
| US7708903B2 (en) * | 2005-11-01 | 2010-05-04 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins and uses thereof |
-
2009
- 2009-03-18 ES ES09721223T patent/ES2397588T3/es active Active
- 2009-03-18 MX MX2010010239A patent/MX2010010239A/es active IP Right Grant
- 2009-03-18 RU RU2010142463/04A patent/RU2476415C2/ru not_active IP Right Cessation
- 2009-03-18 EP EP09721223A patent/EP2260015B1/en not_active Not-in-force
- 2009-03-18 MX MX2014000371A patent/MX345217B/es unknown
- 2009-03-18 CN CN2009801141451A patent/CN102015592B/zh not_active Expired - Fee Related
- 2009-03-18 CN CN201310486564.6A patent/CN103626627B/zh not_active Expired - Fee Related
- 2009-03-18 US US12/922,858 patent/US8436216B2/en not_active Expired - Fee Related
- 2009-03-18 EP EP20110007704 patent/EP2399892A3/en not_active Withdrawn
- 2009-03-18 KR KR1020107023271A patent/KR20110005815A/ko not_active Withdrawn
- 2009-03-18 WO PCT/US2009/037459 patent/WO2009117458A2/en not_active Ceased
- 2009-03-18 CA CA2719042A patent/CA2719042A1/en not_active Abandoned
- 2009-03-18 JP JP2011500913A patent/JP5341978B2/ja not_active Expired - Fee Related
- 2009-03-18 BR BRPI0906249-1A patent/BRPI0906249A2/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009117458A3 (en) | 2010-03-11 |
| EP2260015A2 (en) | 2010-12-15 |
| EP2399892A2 (en) | 2011-12-28 |
| MX345217B (es) | 2017-01-20 |
| KR20110005815A (ko) | 2011-01-19 |
| CN103626627B (zh) | 2016-04-06 |
| EP2399892A3 (en) | 2012-06-13 |
| RU2476415C2 (ru) | 2013-02-27 |
| US20110028769A1 (en) | 2011-02-03 |
| US8436216B2 (en) | 2013-05-07 |
| CN102015592A (zh) | 2011-04-13 |
| BRPI0906249A2 (pt) | 2015-06-30 |
| JP5341978B2 (ja) | 2013-11-13 |
| EP2260015B1 (en) | 2012-10-31 |
| WO2009117458A2 (en) | 2009-09-24 |
| MX2010010239A (es) | 2010-10-05 |
| ES2397588T3 (es) | 2013-03-08 |
| RU2010142463A (ru) | 2012-04-27 |
| CN103626627A (zh) | 2014-03-12 |
| CN102015592B (zh) | 2013-11-20 |
| JP2011515408A (ja) | 2011-05-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20140318 |