JP2017171673A5 - - Google Patents
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- JP2017171673A5 JP2017171673A5 JP2017091549A JP2017091549A JP2017171673A5 JP 2017171673 A5 JP2017171673 A5 JP 2017171673A5 JP 2017091549 A JP2017091549 A JP 2017091549A JP 2017091549 A JP2017091549 A JP 2017091549A JP 2017171673 A5 JP2017171673 A5 JP 2017171673A5
- Authority
- JP
- Japan
- Prior art keywords
- composition according
- mole percent
- chloro
- hydrocarbons
- lewis acid
- 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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- 239000003054 catalyst Substances 0.000 claims description 10
- 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
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 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 6
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical class [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical class F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 claims 2
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 claims 1
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims 1
- IAOGXBHBKZGVGJ-UHFFFAOYSA-N 2,3,3-trichloro-3-fluoroprop-1-ene Chemical compound FC(Cl)(Cl)C(Cl)=C IAOGXBHBKZGVGJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910007926 ZrCl Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical class O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims 1
- 229910001887 tin oxide Inorganic materials 0.000 claims 1
- YUOWTJMRMWQJDA-UHFFFAOYSA-J tin(iv) fluoride Chemical class [F-].[F-].[F-].[F-].[Sn+4] YUOWTJMRMWQJDA-UHFFFAOYSA-J 0.000 claims 1
- 239000011787 zinc oxide Chemical class 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7318608P | 2008-06-17 | 2008-06-17 | |
| US61/073,186 | 2008-06-17 | ||
| US12/484,588 US8916733B2 (en) | 2008-06-17 | 2009-06-15 | Processes for hydrofluorination of 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane |
| US12/484,588 | 2009-06-15 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014243223A Division JP6169065B2 (ja) | 2008-06-17 | 2014-12-01 | ２−クロロ−３，３，３−トリフルオロプロペンの２−クロロ−１，１，１，２−テトラフルオロプロパンへのフッ化水素化のための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017171673A JP2017171673A (ja) | 2017-09-28 |
| JP2017171673A5 true JP2017171673A5 (enExample) | 2018-03-29 |
| JP6434077B2 JP6434077B2 (ja) | 2018-12-05 |
Family
ID=40973192
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009144277A Active JP5686958B2 (ja) | 2008-06-17 | 2009-06-17 | ２−クロロ−３，３，３−トリフルオロプロペンの２−クロロ−１，１，１，２−テトラフルオロプロパンへのフッ化水素化のための方法 |
| JP2014243223A Active JP6169065B2 (ja) | 2008-06-17 | 2014-12-01 | ２−クロロ−３，３，３−トリフルオロプロペンの２−クロロ−１，１，１，２−テトラフルオロプロパンへのフッ化水素化のための方法 |
| JP2017091549A Active JP6434077B2 (ja) | 2008-06-17 | 2017-05-02 | ２−クロロ−３，３，３−トリフルオロプロペンの２−クロロ−１，１，１，２−テトラフルオロプロパンへのフッ化水素化のための方法 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009144277A Active JP5686958B2 (ja) | 2008-06-17 | 2009-06-17 | ２−クロロ−３，３，３−トリフルオロプロペンの２−クロロ−１，１，１，２−テトラフルオロプロパンへのフッ化水素化のための方法 |
| JP2014243223A Active JP6169065B2 (ja) | 2008-06-17 | 2014-12-01 | ２−クロロ−３，３，３−トリフルオロプロペンの２−クロロ−１，１，１，２−テトラフルオロプロパンへのフッ化水素化のための方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8916733B2 (enExample) |
| EP (1) | EP2135855A3 (enExample) |
| JP (3) | JP5686958B2 (enExample) |
| KR (1) | KR101624183B1 (enExample) |
| CN (2) | CN105037074B (enExample) |
| MX (3) | MX2009006519A (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9024092B2 (en) * | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US20230150900A1 (en) * | 2004-04-29 | 2023-05-18 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8664455B2 (en) * | 2008-08-08 | 2014-03-04 | Honeywell International Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US8952208B2 (en) * | 2006-01-03 | 2015-02-10 | Honeywell International Inc. | Method for prolonging a catalyst's life during hydrofluorination |
| US8916733B2 (en) * | 2008-06-17 | 2014-12-23 | Honeywell International Inc. | Processes for hydrofluorination of 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane |
| MX351915B (es) | 2009-12-22 | 2017-11-03 | E I Du Pont De Nemours And Company Star | Composiciones que comprenden 2,3,3,3-tetrafluoropropeno, 1,1,2,3-tetracloropropeno, 2-cloro-3,3,3-trifluoropropeno, o 2-cloro-1,1,1,2-tetrafluoropropano. |
| US8114308B2 (en) * | 2010-03-30 | 2012-02-14 | Honeywell International Inc. | Azeotrope-like composition of 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf) and hydrogen fluoride (HF) |
| US8927791B2 (en) * | 2010-04-29 | 2015-01-06 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
| ES2637832T3 (es) | 2010-10-25 | 2017-10-17 | Arkema France | Proceso para la fabricación de 2-cloro-1,1,1,2-tetrafluoropropano por fluoración en fase líquida de 2-cloro-3,3,3-trifluoropropeno |
| US9890096B2 (en) * | 2011-01-19 | 2018-02-13 | Honeywell International Inc. | Methods of making 2,3,3,3-tetrafluoro-2-propene |
| US9012702B2 (en) | 2011-02-21 | 2015-04-21 | E. I. Du Pont De Nemours And Company | Catalytic dehydrochlorination of hydrochlorofluorocarbons |
| WO2013071024A1 (en) * | 2011-11-10 | 2013-05-16 | Mario Joseph Nappa | Catalytic fluorination process of making hydrohaloalkane |
| WO2014164611A1 (en) * | 2013-03-12 | 2014-10-09 | Honeywell International Inc. | A method for mitigating hfc-245cb formation during hcfo-1233xf hydrofluorination to hcfc-244bb |
| EP2970060A4 (en) | 2013-03-13 | 2016-10-26 | Honeywell Int Inc | STEP-BY-STEP FLUORING METHOD AND REACTOR SYSTEM |
| MX2015011268A (es) * | 2013-03-15 | 2015-12-03 | Honeywell Int Inc | Proceso de fabricacion de 2-cloro-1,1,1,2-tetrafluoropropano (hcfc-244bb). |
| JP6648039B2 (ja) * | 2014-02-10 | 2020-02-14 | 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． | 液相フッ素化反応のための反応器 |
| CN105330511A (zh) * | 2014-08-07 | 2016-02-17 | 西安近代化学研究所 | 一种制备2-氯-1,1,1,2-四氟丙烷的方法 |
| KR102699589B1 (ko) * | 2015-05-21 | 2024-08-28 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | SbF5에 의한 1233xf의 244bb로의 히드로플루오린화 |
| US10562831B2 (en) * | 2015-09-21 | 2020-02-18 | Arkema Inc. | Process for making tetrachloropropene by catalyzed gas-phase dehydrochlorination of pentachloropropane |
| JP6360084B2 (ja) * | 2016-01-14 | 2018-07-18 | アルケマ フランス | ２−クロロ−３，３，３−トリフルオロプロペンの液相フッ素化で２−クロロ−１，１，１，２−テトラフルオロプロペンを製造する方法 |
| US10246389B1 (en) * | 2018-01-08 | 2019-04-02 | Honeywell International Inc. | Compositions containing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| FR3084359B1 (fr) | 2018-07-25 | 2021-11-26 | Arkema France | Procede de production et de purification du 2-chloro-1,1,1,2-tetrafluoropropane. |
| CN109608302B (zh) * | 2018-11-27 | 2021-08-06 | 浙江三美化工股份有限公司 | 一种2，3，3，3-四氟丙烯的制备方法 |
| USD1000414S1 (en) * | 2023-05-18 | 2023-10-03 | Song WAN | Ear pad |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5316690A (en) * | 1991-04-18 | 1994-05-31 | Allied Signal Inc. | Hydrochlorofluorocarbons having OH rate constants which do not contribute substantially to ozone depletion and global warming |
| JP3213929B2 (ja) * | 1994-07-14 | 2001-10-02 | ダイキン工業株式会社 | １，１，１，２，３，３，３−ヘプタフルオロプロパンの製造方法 |
| US5616819A (en) * | 1995-08-28 | 1997-04-01 | Laroche Industries Inc. | Process for preparing fluorinated aliphatic compounds |
| US5905174A (en) * | 1997-04-15 | 1999-05-18 | Central Glass Company, Limited | Method for producing 3,3-dichloro-1,1,1-triflouroacetone |
| EP0939071B1 (en) * | 1998-02-26 | 2003-07-30 | Central Glass Company, Limited | Method for producing fluorinated propane |
| JP3031465B2 (ja) * | 1998-02-26 | 2000-04-10 | セントラル硝子株式会社 | １，１，１，３，３−ペンタフルオロプロパンの製造方法 |
| JP3031464B2 (ja) * | 1998-02-26 | 2000-04-10 | セントラル硝子株式会社 | １，１，１，３，３−ペンタフルオロプロパンの製造方法 |
| JP2000063301A (ja) * | 1998-08-18 | 2000-02-29 | Central Glass Co Ltd | フッ素化プロパンの製造方法 |
| US6063970A (en) | 1998-10-08 | 2000-05-16 | Laroche Industries, Inc. | Process for preparing fluorinated aliphatic compounds |
| US6759381B1 (en) * | 2003-05-06 | 2004-07-06 | Honeywell International Inc. | Azeotrope-like compositions of 1-chloro-1,3,3,3-tetrafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene |
| JP4257424B2 (ja) * | 2004-03-09 | 2009-04-22 | 独立行政法人産業技術総合研究所 | フッ素化反応用触媒 |
| US20090182179A1 (en) * | 2008-01-15 | 2009-07-16 | Honeywell International Inc. | Hydrofluorination of 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane with catalysts of sbcl3, sbcl5, sbf5, ticl4, sncl4, cr2o3 and fluorinated cr2o3 |
| US8067649B2 (en) * | 2004-04-29 | 2011-11-29 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8324436B2 (en) * | 2006-01-03 | 2012-12-04 | Honeywell International Inc. | Gas phase synthesis of 2,3,3,3-tetrafluoro-1-propene from 2-chloro-3,3,3-trifluoro-1-propene |
| US8664455B2 (en) * | 2008-08-08 | 2014-03-04 | Honeywell International Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| ES2639623T5 (es) | 2006-01-03 | 2024-10-04 | Honeywell Int Inc | Método para preparar compuestos orgánicos fluorados |
| KR101550250B1 (ko) | 2007-06-27 | 2015-09-04 | 알케마 인코포레이티드 | 하이드로플루오로올레핀의 제조 방법 |
| US7795480B2 (en) * | 2007-07-25 | 2010-09-14 | Honeywell International Inc. | Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) |
| US8916733B2 (en) * | 2008-06-17 | 2014-12-23 | Honeywell International Inc. | Processes for hydrofluorination of 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane |
-
2009
- 2009-06-15 US US12/484,588 patent/US8916733B2/en active Active
- 2009-06-16 EP EP09162839A patent/EP2135855A3/en not_active Withdrawn
- 2009-06-16 CN CN201510463262.6A patent/CN105037074B/zh active Active
- 2009-06-16 CN CN200910152393.7A patent/CN101607865B/zh active Active
- 2009-06-17 MX MX2009006519A patent/MX2009006519A/es active IP Right Grant
- 2009-06-17 KR KR1020090053798A patent/KR101624183B1/ko active Active
- 2009-06-17 MX MX2016016327A patent/MX359226B/es unknown
- 2009-06-17 JP JP2009144277A patent/JP5686958B2/ja active Active
- 2009-06-17 MX MX2014008615A patent/MX345304B/es unknown
-
2014
- 2014-12-01 JP JP2014243223A patent/JP6169065B2/ja active Active
-
2017
- 2017-05-02 JP JP2017091549A patent/JP6434077B2/ja active Active
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