JP2014503494A5 - - Google Patents
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- JP2014503494A5 JP2014503494A5 JP2013538962A JP2013538962A JP2014503494A5 JP 2014503494 A5 JP2014503494 A5 JP 2014503494A5 JP 2013538962 A JP2013538962 A JP 2013538962A JP 2013538962 A JP2013538962 A JP 2013538962A JP 2014503494 A5 JP2014503494 A5 JP 2014503494A5
- Authority
- JP
- Japan
- Prior art keywords
- ppm
- hcfo
- trifluoropropene
- chloro
- tetrafluoropropane
- 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.)
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- 238000000034 method Methods 0.000 claims description 18
- 239000012535 impurity Substances 0.000 claims description 12
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims description 10
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims description 8
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims description 8
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 claims description 8
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims description 7
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 claims description 4
- ZHJBJVPTRJNNIK-UPHRSURJSA-N (z)-1,2-dichloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(\Cl)=C\Cl ZHJBJVPTRJNNIK-UPHRSURJSA-N 0.000 claims description 4
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 claims description 4
- PFFGXVGPSGJOBV-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropane Chemical compound FCCC(F)(F)F PFFGXVGPSGJOBV-UHFFFAOYSA-N 0.000 claims description 4
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 4
- IAPGBTZUBKUKOR-UHFFFAOYSA-N 2,3-dichloro-3,3-difluoroprop-1-ene Chemical compound FC(F)(Cl)C(Cl)=C IAPGBTZUBKUKOR-UHFFFAOYSA-N 0.000 claims description 4
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 4
- PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical compound FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 claims description 4
- HXNJCCYKKHPFIO-UHFFFAOYSA-N 3-chloro-1,1,2,3-tetrafluoroprop-1-ene Chemical compound FC(Cl)C(F)=C(F)F HXNJCCYKKHPFIO-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical class FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41407410P | 2010-11-16 | 2010-11-16 | |
| US61/414,074 | 2010-11-16 | ||
| US13/281,063 US8975454B2 (en) | 2008-07-31 | 2011-10-25 | Process for producing 2,3,3,3-tetrafluoropropene |
| US13/281,063 | 2011-10-25 | ||
| PCT/US2011/060519 WO2012067980A2 (en) | 2010-11-16 | 2011-11-14 | Process for producing 2,3,3,3-tetrafluoropropene |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016146072A Division JP2016222697A (ja) | 2010-11-16 | 2016-07-26 | ２，３，３，３−テトラフルオロプロペンの製造法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014503494A JP2014503494A (ja) | 2014-02-13 |
| JP2014503494A5 true JP2014503494A5 (enExample) | 2014-12-25 |
| JP6013353B2 JP6013353B2 (ja) | 2016-10-25 |
Family
ID=46084581
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013538962A Active JP6013353B2 (ja) | 2010-11-16 | 2011-11-14 | ２，３，３，３−テトラフルオロプロペンの製造法 |
| JP2016146072A Pending JP2016222697A (ja) | 2010-11-16 | 2016-07-26 | ２，３，３，３−テトラフルオロプロペンの製造法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016146072A Pending JP2016222697A (ja) | 2010-11-16 | 2016-07-26 | ２，３，３，３−テトラフルオロプロペンの製造法 |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US8975454B2 (enExample) |
| EP (1) | EP2640682B1 (enExample) |
| JP (2) | JP6013353B2 (enExample) |
| KR (1) | KR20130140073A (enExample) |
| CN (3) | CN103328423A (enExample) |
| ES (1) | ES2692858T3 (enExample) |
| MX (1) | MX2013005514A (enExample) |
| WO (1) | WO2012067980A2 (enExample) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20230150900A1 (en) * | 2004-04-29 | 2023-05-18 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US9024092B2 (en) * | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8845921B2 (en) * | 2008-04-09 | 2014-09-30 | Honeywell International Inc. | Separation of close boiling compounds by addition of a third compound |
| CA3076129C (en) | 2008-05-07 | 2022-10-18 | The Chemours Company Fc, Llc | Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene |
| WO2011077191A1 (en) * | 2009-12-23 | 2011-06-30 | Arkema France | Catalytic gas phase fluorination of 1230xa to 1234yf |
| FR2962130B1 (fr) * | 2010-06-30 | 2012-07-20 | Arkema France | Composition a base de 2,3,3,3-tetrafluoropropene |
| FR2962442B1 (fr) | 2010-07-09 | 2016-02-26 | Arkema France | Composition stable de 2,3,3,3-tetrafluoropropene |
| US8796493B2 (en) | 2011-09-30 | 2014-08-05 | Honeywell International Inc. | Methods to separate halogentated olefins from 2-chloro-1,1,1,2-tetrafluoropropane using a solid adsorbent |
| WO2013119919A1 (en) | 2012-02-10 | 2013-08-15 | Haiyou Wang | Improved process for the manufacture of 2,3,3,3-tetrafluoropropene |
| KR20150021551A (ko) * | 2012-06-06 | 2015-03-02 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 플루오로올레핀 중 RfCCX 불순물의 감소 방법 |
| FR3000096B1 (fr) | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
| US9242910B2 (en) * | 2013-03-15 | 2016-01-26 | Honeywell International Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US10995047B2 (en) | 2013-03-15 | 2021-05-04 | The Chemours Company Fc, Llc | Process for the reduction of RƒC≡CX impurities in fluoroolefins |
| KR20250150693A (ko) * | 2013-03-15 | 2025-10-20 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜 생성물에서 할로겐화 에틸렌 불순물을 제거하는 방법 |
| US20150259267A1 (en) | 2014-03-14 | 2015-09-17 | E.I. Du Pont De Nemours And Company | PROCESS FOR THE REDUCTION OF RfC=CX IMPURITIES IN FLUOROOLEFINS |
| EP3412647B2 (en) * | 2013-03-15 | 2024-02-14 | The Chemours Company FC, LLC | Process for the reduction of alkyne impurities in fluoroolefins |
| US9233895B2 (en) | 2013-03-15 | 2016-01-12 | Honeywell International, Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| WO2015120234A1 (en) * | 2014-02-10 | 2015-08-13 | Merkel Daniel C | Reactor for liquid phase fluorination reactions |
| KR101624081B1 (ko) | 2014-06-10 | 2016-05-24 | 주식회사 엘지화학 | 열 회수 장치 |
| PL3098281T3 (pl) * | 2014-09-25 | 2021-01-25 | Daikin Industries, Ltd. | Kompozycja zawierająca HFC i HFO |
| CN106458802B (zh) | 2014-09-26 | 2020-03-31 | 大金工业株式会社 | 卤代烯烃类组合物 |
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| JP6503765B2 (ja) * | 2015-02-02 | 2019-04-24 | セントラル硝子株式会社 | 含フッ素オレフィンを構成成分とする共沸様組成物 |
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| JP6028825B2 (ja) * | 2015-03-31 | 2016-11-24 | ダイキン工業株式会社 | ハイドロフルオロオレフィン化合物を含有する組成物 |
| JP2018513197A (ja) * | 2015-04-24 | 2018-05-24 | ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． | ２４４ｂｂ中の１２３３ｘｆの濃度を減少させる方法 |
| US9764998B2 (en) * | 2015-05-12 | 2017-09-19 | Honeywell International Inc. | Process for making HCFO-1233zd |
| EP3297980A4 (en) | 2015-05-21 | 2018-12-26 | The Chemours Company FC, LLC | HYDROFLUORINATION OF 1233xf TO 244bb BY SbF5 |
| JP6102984B2 (ja) * | 2015-05-29 | 2017-03-29 | ダイキン工業株式会社 | 含フッ素化合物の製造方法 |
| GB201512510D0 (en) * | 2015-07-17 | 2015-08-19 | Mexichem Fluor Sa De Cv | Process |
| US9938213B2 (en) * | 2015-08-19 | 2018-04-10 | Honeywell International Inc. | Methods for removing acidic impurities from halogenated propenes |
| MX2018001665A (es) * | 2015-09-16 | 2018-05-07 | Honeywell Int Inc | Proceso novedoso para fabricar 2-cloro-3,3,3-trifluoropropeno a partir de 1,2-dicloro-3,3,3-trifluoropropeno. |
| MX2018004232A (es) * | 2015-10-15 | 2018-05-15 | Honeywell Int Inc | Reactor y proceso de dishidrogenacion. |
| JP2018538130A (ja) * | 2015-11-05 | 2018-12-27 | ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． | １２３０ｘａプロセスによる１２３４ｙｆ中の副生成物の無水塩酸又は塩酸水溶液からフッ素化有機化合物を除去する方法 |
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| FR3056210B1 (fr) * | 2016-09-22 | 2020-03-13 | Arkema France | Procede de separation du 2-chloro-1,1,1,2-tetrafluoropropane et du 2-chloro-3,3,3-trifluoropropene. |
| FR3056209B1 (fr) * | 2016-09-22 | 2018-09-07 | Arkema France | Procede de preparation de 2-chloro-1,1,1-trifluoropropane. |
| JP6968162B2 (ja) | 2016-11-08 | 2021-11-17 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | フッ素化シクロブタンを生成するためのプロセス |
| CN106631682B (zh) * | 2016-12-31 | 2023-08-25 | 山东华安新材料有限公司 | 一种从2-氯-1,1,1,2-四氟丙烷中分离水的设备及方法 |
| GB201701099D0 (en) | 2017-01-23 | 2017-03-08 | Mexichem Fluor Sa De Cv | Process |
| PT3592723T (pt) * | 2017-03-10 | 2023-12-19 | Chemours Co Fc Llc | Processo de preparação de 3,3,3-trifluoroprop-1-eno |
| FR3065725B1 (fr) * | 2017-04-28 | 2020-01-24 | Arkema France | Procede de purification du 1,1,1,2,2-pentafluoropropane. |
| US10233137B1 (en) * | 2017-10-13 | 2019-03-19 | Honeywell International Inc. | Method for removing unsaturated halogenated impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf) |
| US10125066B1 (en) * | 2017-11-29 | 2018-11-13 | Honeywell International Inc. | Process for making high purity 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US10351494B1 (en) * | 2018-01-08 | 2019-07-16 | Honeywell International Inc. | Systems and methods for reducing the formation of impurities during 244bb dehydrochlorination to 1234yf |
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| FR3076553B1 (fr) | 2018-01-08 | 2020-07-31 | Arkema France | Procede de purification du 1,1,1,2,3-pentafluoropropane et utilisation de celui-ci pour l'obtention de 2,3,3,3-tetrafluoropropene de haute purete. |
| FR3078699B1 (fr) * | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| EP3978580B1 (en) * | 2018-04-30 | 2023-06-14 | The Chemours Company FC, LLC | Stabilized fluoroolefin compositions and method for their production, storage and usage |
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| JP2021527055A (ja) * | 2018-06-06 | 2021-10-11 | ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． | ＨＣＦＣ−２４４ｂｂを脱塩化水素化してＨＦＯ−１２３４ｙｆを製造する方法 |
| FR3083232B1 (fr) | 2018-06-27 | 2021-11-12 | Arkema France | Procede de production du 1-chloro-3,3,3-trifluoropropene |
| FR3084359B1 (fr) * | 2018-07-25 | 2021-11-26 | Arkema France | Procede de production et de purification du 2-chloro-1,1,1,2-tetrafluoropropane. |
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| KR101394583B1 (ko) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
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2011
- 2011-10-25 US US13/281,063 patent/US8975454B2/en active Active
- 2011-11-14 ES ES11841964.7T patent/ES2692858T3/es active Active
- 2011-11-14 JP JP2013538962A patent/JP6013353B2/ja active Active
- 2011-11-14 MX MX2013005514A patent/MX2013005514A/es unknown
- 2011-11-14 CN CN2011800650324A patent/CN103328423A/zh active Pending
- 2011-11-14 CN CN201610597146.8A patent/CN106278803A/zh active Pending
- 2011-11-14 CN CN201610597147.2A patent/CN106278804A/zh active Pending
- 2011-11-14 WO PCT/US2011/060519 patent/WO2012067980A2/en not_active Ceased
- 2011-11-14 KR KR1020137015281A patent/KR20130140073A/ko not_active Ceased
- 2011-11-14 EP EP11841964.7A patent/EP2640682B1/en not_active Revoked
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2015
- 2015-03-10 US US14/643,668 patent/US10155706B2/en active Active
- 2015-03-10 US US14/643,607 patent/US9260365B2/en active Active
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2017
- 2017-02-28 US US15/445,407 patent/US10125068B2/en active Active
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