JP2017504609A5 - - Google Patents
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- Publication number
- JP2017504609A5 JP2017504609A5 JP2016541625A JP2016541625A JP2017504609A5 JP 2017504609 A5 JP2017504609 A5 JP 2017504609A5 JP 2016541625 A JP2016541625 A JP 2016541625A JP 2016541625 A JP2016541625 A JP 2016541625A JP 2017504609 A5 JP2017504609 A5 JP 2017504609A5
- Authority
- JP
- Japan
- Prior art keywords
- halide
- catalyst
- reaction
- reactor
- selectivity
- 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
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- -1 antimony metalloid Chemical class 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- 229910001507 metal halide Inorganic materials 0.000 description 6
- 150000005309 metal halides Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910000856 hastalloy Inorganic materials 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052752 metalloid Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- 150000002738 metalloids Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical group Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019125345A JP6888896B2 (ja) | 2013-12-18 | 2019-07-04 | ３，３，３−トリフルオロプロペンの２，３−ジクロロ−１，１，１−トリフルオロプロパンへの触媒的塩素化 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361917657P | 2013-12-18 | 2013-12-18 | |
| US61/917,657 | 2013-12-18 | ||
| PCT/US2014/071114 WO2015095497A1 (en) | 2013-12-18 | 2014-12-18 | Catalytic chlorination of 3,3,3-trifluoropropene to 2,3-dichloro-1,1,1-trifluoropropane |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019125345A Division JP6888896B2 (ja) | 2013-12-18 | 2019-07-04 | ３，３，３−トリフルオロプロペンの２，３−ジクロロ−１，１，１−トリフルオロプロパンへの触媒的塩素化 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017504609A JP2017504609A (ja) | 2017-02-09 |
| JP2017504609A5 true JP2017504609A5 (enExample) | 2017-11-02 |
| JP6553619B2 JP6553619B2 (ja) | 2019-07-31 |
Family
ID=53403684
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016541625A Active JP6553619B2 (ja) | 2013-12-18 | 2014-12-18 | ３，３，３−トリフルオロプロペンの２，３−ジクロロ−１，１，１−トリフルオロプロパンへの触媒的塩素化 |
| JP2019125345A Active JP6888896B2 (ja) | 2013-12-18 | 2019-07-04 | ３，３，３−トリフルオロプロペンの２，３−ジクロロ−１，１，１−トリフルオロプロパンへの触媒的塩素化 |
| JP2021084699A Active JP7697816B6 (ja) | 2013-12-18 | 2021-05-19 | １，１，１－トリフルオロ－２，３－ジクロロプロパンを含む組成物 |
| JP2023150037A Pending JP2023169295A (ja) | 2013-12-18 | 2023-09-15 | １，１，１－トリフルオロ－２，３－ジクロロプロパンを含む組成物 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019125345A Active JP6888896B2 (ja) | 2013-12-18 | 2019-07-04 | ３，３，３−トリフルオロプロペンの２，３−ジクロロ−１，１，１−トリフルオロプロパンへの触媒的塩素化 |
| JP2021084699A Active JP7697816B6 (ja) | 2013-12-18 | 2021-05-19 | １，１，１－トリフルオロ－２，３－ジクロロプロパンを含む組成物 |
| JP2023150037A Pending JP2023169295A (ja) | 2013-12-18 | 2023-09-15 | １，１，１－トリフルオロ－２，３－ジクロロプロパンを含む組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9938208B2 (enExample) |
| EP (2) | EP3643695B1 (enExample) |
| JP (4) | JP6553619B2 (enExample) |
| KR (5) | KR102666338B1 (enExample) |
| CN (2) | CN106164026B (enExample) |
| MX (2) | MX2016007916A (enExample) |
| WO (1) | WO2015095497A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106164026B (zh) * | 2013-12-18 | 2021-02-09 | 纳幕尔杜邦公司 | 使3,3,3-三氟丙烯催化氯化成2,3-二氯-1,1,1-三氟丙烷 |
| HRP20231540T1 (hr) | 2017-03-10 | 2024-03-01 | The Chemours Company Fc, Llc | Postupak za pripremu 3,3,3-trifluoroprop-1-ena |
| JP2019151629A (ja) * | 2018-03-05 | 2019-09-12 | セントラル硝子株式会社 | 化合物の製造方法 |
| FR3081721B1 (fr) * | 2018-06-01 | 2022-04-15 | Arkema France | Procede de preparation d'un sel de lithium de bis(fluorosulfonyl)imide |
| US20210198168A1 (en) | 2018-07-09 | 2021-07-01 | The Chemours Company Fc, Llc | Compositions and methods for an integrated 2,3,3,3-tetrafluoropropene manufacturing process |
| JP2024515192A (ja) | 2021-04-19 | 2024-04-05 | 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 | ３，３，３－トリフルオロプロペン（１２４３ｚｆ）を含有する組成物並びに当該組成物の製造及び使用方法 |
| KR20240138166A (ko) | 2023-03-10 | 2024-09-20 | 광주과학기술원 | 전기화학적 탈합금 처리를 이용한 고함량의 비금속을 함유하는 전이금속 촉매 및 이의 제조방법 |
| WO2025064346A1 (en) | 2023-09-18 | 2025-03-27 | The Chemours Company Fc, Llc | Processes for preparing 2-chloro-1,1,1,2-tetrafluoropropane |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3331962A1 (de) * | 1983-09-05 | 1985-03-21 | Wacker-Chemie GmbH, 8000 München | Verfahren zur aufbereitung von chlorwasserstoff als einsatzstoff fuer den ethylenoxichlorierungsprozess |
| DE3445896C1 (de) * | 1984-12-15 | 1986-04-10 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur kontinuierlichen Herstellung von 1.2-Dichlorethan |
| IN172054B (enExample) * | 1988-02-24 | 1993-03-27 | Du Pont | |
| US5120883A (en) * | 1991-08-26 | 1992-06-09 | E. I. Du Pont De Nemours And Company | Catalytic process for producing CCl3 CF3 |
| KR950011099B1 (ko) * | 1992-06-05 | 1995-09-28 | 한국과학기술연구원 | 1,1,1-트리플루오로-2,2-디클로로에탄의 제조 방법 |
| US6204418B1 (en) * | 1994-09-07 | 2001-03-20 | John E. Stauffer | Process for the chlornation of hydrocarbons |
| CN1178883C (zh) * | 1998-06-02 | 2004-12-08 | 纳幕尔杜邦公司 | 六氟丙烯和任选地其他含氟卤代碳氢化合物的制备方法 |
| US6583328B1 (en) * | 1999-04-05 | 2003-06-24 | Pcbu Services, Inc. | Method for the preparation of 1,1,1,3,3-pentafluoropropene and 1,1,1,3,3-pentafluoropropane |
| JP2002273206A (ja) * | 2001-03-16 | 2002-09-24 | Mitsubishi Chemicals Corp | 合成反応装置及びそれを用いる合成反応方法 |
| JP2007105668A (ja) * | 2005-10-14 | 2007-04-26 | Mitsubishi Chemicals Corp | 気液反応方法及びそのための装置 |
| US8071825B2 (en) * | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| GB0706978D0 (en) * | 2007-04-11 | 2007-05-16 | Ineos Fluor Holdings Ltd | Process |
| GB0806419D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| JP5701205B2 (ja) * | 2008-05-07 | 2015-04-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | ２，３−ジクロロ−１，１，１−トリフルオロプロパン、２−クロロ−１，１，１−トリフルオロプロペン、２−クロロ−１，１，１，２−テトラフルオロプロパンまたは２，３，３，３−テトラフルオロプロペンを含む組成物 |
| FR2935700B1 (fr) | 2008-09-11 | 2013-05-10 | Arkema France | Procede de preparation de composes trifluores et tetrafluores |
| WO2010071136A1 (ja) * | 2008-12-16 | 2010-06-24 | 旭硝子株式会社 | ２－クロロ－１，１，１，２－テトラフルオロプロパンおよび２，３，３，３－テトラフルオロプロペンの製造方法 |
| CN102686542A (zh) * | 2009-12-23 | 2012-09-19 | 阿克马法国公司 | 1233xf到1234yf的催化气相氟化 |
| WO2011135395A1 (en) * | 2010-04-26 | 2011-11-03 | Arkema France | Process for the manufacture of 2-chloro-3, 3,3-trifluoropropene (hcfo1233xf) by liquid phase fluorination of pentachloropropane |
| KR101641740B1 (ko) * | 2010-04-30 | 2016-07-21 | 동우 화인켐 주식회사 | 구리와 티타늄을 포함하는 금속막용 식각액 조성물 |
| US8927791B2 (en) * | 2010-04-29 | 2015-01-06 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
| CN102336630B (zh) * | 2011-07-07 | 2014-01-29 | 浙江衢化氟化学有限公司 | 一种2，3-二氯-1，1，1-三氟丙烷的催化合成方法 |
| JP6245013B2 (ja) * | 2013-04-02 | 2017-12-13 | セントラル硝子株式会社 | １，２−ジクロロ−３，３，３−トリフルオロプロペンの製造方法 |
| CN103418367B (zh) * | 2013-07-12 | 2015-10-28 | 西安近代化学研究所 | 一种用于氯氟烷烃制备含氟烯烃的催化剂及制备方法 |
| CN106164026B (zh) * | 2013-12-18 | 2021-02-09 | 纳幕尔杜邦公司 | 使3,3,3-三氟丙烯催化氯化成2,3-二氯-1,1,1-三氟丙烷 |
-
2014
- 2014-12-18 CN CN201480075865.2A patent/CN106164026B/zh active Active
- 2014-12-18 CN CN202011000993.4A patent/CN112321383A/zh active Pending
- 2014-12-18 MX MX2016007916A patent/MX2016007916A/es unknown
- 2014-12-18 KR KR1020237009965A patent/KR102666338B1/ko active Active
- 2014-12-18 EP EP19217132.0A patent/EP3643695B1/en active Active
- 2014-12-18 KR KR1020167018850A patent/KR102369619B1/ko active Active
- 2014-12-18 EP EP14872853.8A patent/EP3083536B1/en active Active
- 2014-12-18 KR KR1020227006274A patent/KR102515340B1/ko active Active
- 2014-12-18 WO PCT/US2014/071114 patent/WO2015095497A1/en not_active Ceased
- 2014-12-18 KR KR1020247015438A patent/KR102771487B1/ko active Active
- 2014-12-18 KR KR1020257005228A patent/KR20250026892A/ko active Pending
- 2014-12-18 JP JP2016541625A patent/JP6553619B2/ja active Active
- 2014-12-18 US US15/106,418 patent/US9938208B2/en active Active
-
2016
- 2016-06-16 MX MX2022016383A patent/MX2022016383A/es unknown
-
2018
- 2018-02-20 US US15/899,990 patent/US10843987B2/en active Active
-
2019
- 2019-07-04 JP JP2019125345A patent/JP6888896B2/ja active Active
-
2021
- 2021-05-19 JP JP2021084699A patent/JP7697816B6/ja active Active
-
2023
- 2023-09-15 JP JP2023150037A patent/JP2023169295A/ja active Pending
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