JP2015530417A5 - - Google Patents
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- Publication number
- JP2015530417A5 JP2015530417A5 JP2015534687A JP2015534687A JP2015530417A5 JP 2015530417 A5 JP2015530417 A5 JP 2015530417A5 JP 2015534687 A JP2015534687 A JP 2015534687A JP 2015534687 A JP2015534687 A JP 2015534687A JP 2015530417 A5 JP2015530417 A5 JP 2015530417A5
- Authority
- JP
- Japan
- Prior art keywords
- hexafluoro
- butyne
- alkali metal
- chloro
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 23
- WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical compound FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 claims description 12
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- JRENXZBKMHPULY-UPHRSURJSA-N (z)-2-chloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C(/Cl)C(F)(F)F JRENXZBKMHPULY-UPHRSURJSA-N 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical group [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- JRENXZBKMHPULY-OWOJBTEDSA-N (e)-2-chloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C(\Cl)C(F)(F)F JRENXZBKMHPULY-OWOJBTEDSA-N 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- JRENXZBKMHPULY-UHFFFAOYSA-N 2-chloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)C=C(Cl)C(F)(F)F JRENXZBKMHPULY-UHFFFAOYSA-N 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 5
- DRNMSWBRUAIIJO-UHFFFAOYSA-N 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)C(Cl)C(Cl)C(F)(F)F DRNMSWBRUAIIJO-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KQBWUCNIYWMKEK-UHFFFAOYSA-N 1-chloro-1-fluorobut-1-ene Chemical compound CCC=C(F)Cl KQBWUCNIYWMKEK-UHFFFAOYSA-N 0.000 description 2
- DUPQXMJUMBAVMO-UHFFFAOYSA-N 1-chloro-1-fluorobutane Chemical group CCCC(F)Cl DUPQXMJUMBAVMO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 1
- ZRLVUNNBSSUWAC-UHFFFAOYSA-M hydrogen sulfate;tetraoctylazanium Chemical compound OS([O-])(=O)=O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC ZRLVUNNBSSUWAC-UHFFFAOYSA-M 0.000 description 1
- KKWUACQXLWHLCX-UHFFFAOYSA-N hydron;tetradecan-1-amine;chloride Chemical compound Cl.CCCCCCCCCCCCCCN KKWUACQXLWHLCX-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical group CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CUXKZYSCZCNPNX-UHFFFAOYSA-N tetradecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCC[NH3+] CUXKZYSCZCNPNX-UHFFFAOYSA-N 0.000 description 1
- KEVJUENWYCMNET-UHFFFAOYSA-M tetradodecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC KEVJUENWYCMNET-UHFFFAOYSA-M 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- SNNIPOQLGBPXPS-UHFFFAOYSA-M tetraoctylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC SNNIPOQLGBPXPS-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261707231P | 2012-09-28 | 2012-09-28 | |
| US201261707220P | 2012-09-28 | 2012-09-28 | |
| US61/707,220 | 2012-09-28 | ||
| US61/707,231 | 2012-09-28 | ||
| PCT/US2013/062080 WO2014052695A1 (en) | 2012-09-28 | 2013-09-27 | Dehydrochlorination of chlorinated reactants to produce 1,1,1,4,4,4-hexafluoro-2-butyne |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015530417A JP2015530417A (ja) | 2015-10-15 |
| JP2015530417A5 true JP2015530417A5 (enExample) | 2016-08-25 |
| JP6272877B2 JP6272877B2 (ja) | 2018-01-31 |
Family
ID=49354928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015534687A Active JP6272877B2 (ja) | 2012-09-28 | 2013-09-27 | １，１，１，４，４，４−ヘキサフルオロ−２−ブチンを製造するための塩素化反応物の脱塩酸 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2922809A1 (enExample) |
| JP (1) | JP6272877B2 (enExample) |
| KR (1) | KR102147909B1 (enExample) |
| CN (2) | CN108530261A (enExample) |
| IN (1) | IN2015DN01199A (enExample) |
| MX (1) | MX371333B (enExample) |
| WO (1) | WO2014052695A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9440896B2 (en) | 2012-09-28 | 2016-09-13 | The Chemours Company Fc, Llc | Dehydrochlorination of HCFC-336 isomers to 1,1,1,4,4,4-hexafluoro-2-butyne |
| 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 |
| US9328042B2 (en) | 2014-08-11 | 2016-05-03 | The Chemours Company Fc, Llc | Integrated process for the production of Z-1,1,1,4,4,4-hexafluoro-2-butene |
| CN106349007B (zh) * | 2016-08-22 | 2019-06-11 | 巨化集团技术中心 | 一种z-hfo-1336的制备方法 |
| EP3658523B1 (en) * | 2017-07-27 | 2023-04-26 | The Chemours Company FC, LLC | Process for preparing (z)-1,1,1,4,4,4-hexafluoro-2-butene |
| JP6933239B2 (ja) | 2019-02-21 | 2021-09-08 | ダイキン工業株式会社 | ハロゲン化アルケン化合物及びフッ化アルキン化合物の製造方法 |
| WO2020171011A1 (ja) * | 2019-02-21 | 2020-08-27 | ダイキン工業株式会社 | ハロゲン化アルケン化合物及びフッ化アルキン化合物の製造方法 |
| MY208986A (en) * | 2019-04-05 | 2025-06-14 | Chemours Co Fc Llc | Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same |
| JP7682098B2 (ja) * | 2019-04-05 | 2025-05-23 | 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－ヘキサフルオロブタ－２－エン及びそれを生成するための中間体を生成するためのプロセス |
| CA3131606A1 (en) * | 2019-04-05 | 2020-10-08 | The Chemours Company Fc, Llc | Process for producing 1,1,1,4,4,4-hexafluorobut-2-ene |
| MX2021011163A (es) * | 2019-04-05 | 2021-10-22 | Chemours Co Fc Llc | Procesos para producir z-1,1,1,4,4,4-hexafluorobut-2-eno e intermediarios para producirlo. |
| CN110950735B (zh) * | 2019-10-22 | 2022-08-30 | 浙江巨化技术中心有限公司 | 一种气相法制备1,1,1,4,4,4-六氟-2-丁炔的方法 |
| CN110845296A (zh) * | 2019-12-12 | 2020-02-28 | 岳阳市宇恒化工有限公司 | 一种制备炔基化合物的方法 |
| 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 |
| CN114409514B (zh) * | 2021-12-21 | 2023-07-18 | 西安近代化学研究所 | 一种1,1,1,4,4,4-六氟-2-丁酮的合成方法 |
| WO2025019738A1 (en) | 2023-07-20 | 2025-01-23 | The Chemours Company Fc, Llc | Compositions of chlorofluorinated compounds |
| WO2025019740A1 (en) | 2023-07-20 | 2025-01-23 | The Chemours Company Fc, Llc | Compositions comprising 1,1,1,4,4,4-hexafluoro-2-butyne |
| WO2025019754A1 (en) * | 2023-07-20 | 2025-01-23 | The Chemours Company Fc, Llc | Processes for the production of hexafluoro-2-butyne and compositions thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6210027A (ja) * | 1985-07-08 | 1987-01-19 | Daikin Ind Ltd | ２−トリフルオロメチル−３，３，３−トリフルオロプロペンの製法 |
| US6548719B1 (en) | 2001-09-25 | 2003-04-15 | Honeywell International | Process for producing fluoroolefins |
| JP5380882B2 (ja) * | 2007-04-17 | 2014-01-08 | セントラル硝子株式会社 | ３，３，３−トリフルオロプロピンの製造方法 |
| WO2009035130A2 (en) * | 2007-09-11 | 2009-03-19 | Daikin Industries, Ltd. | Process for producing 2,3,3,3-tetrafluoropropene |
| JP2010037205A (ja) | 2008-07-31 | 2010-02-18 | Nippon Zeon Co Ltd | フッ素アルカン化合物、その製造方法及びパーフルオロアルキン化合物の製造方法 |
| US8667404B2 (en) | 2008-08-06 | 2014-03-04 | Autodesk, Inc. | Predictive material editor |
| US8901360B2 (en) * | 2010-05-21 | 2014-12-02 | Honeywell International Inc. | Process for cis 1,1,1,4,4,4-hexafluoro-2-butene |
-
2013
- 2013-09-27 MX MX2015003797A patent/MX371333B/es active IP Right Grant
- 2013-09-27 EP EP13776644.0A patent/EP2922809A1/en not_active Withdrawn
- 2013-09-27 KR KR1020157007748A patent/KR102147909B1/ko active Active
- 2013-09-27 WO PCT/US2013/062080 patent/WO2014052695A1/en not_active Ceased
- 2013-09-27 JP JP2015534687A patent/JP6272877B2/ja active Active
- 2013-09-27 CN CN201810409549.4A patent/CN108530261A/zh active Pending
- 2013-09-27 CN CN201380050238.9A patent/CN104684877A/zh active Pending
-
2015
- 2015-02-13 IN IN1199DEN2015 patent/IN2015DN01199A/en unknown
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