JP5595689B2 - 2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)を製造するための改良法 - Google Patents
2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)を製造するための改良法 Download PDFInfo
- Publication number
- JP5595689B2 JP5595689B2 JP2009184438A JP2009184438A JP5595689B2 JP 5595689 B2 JP5595689 B2 JP 5595689B2 JP 2009184438 A JP2009184438 A JP 2009184438A JP 2009184438 A JP2009184438 A JP 2009184438A JP 5595689 B2 JP5595689 B2 JP 5595689B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- chloro
- catalyst
- liquid phase
- pressure
- 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.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8720608P | 2008-08-08 | 2008-08-08 | |
| US61/087,206 | 2008-08-08 | ||
| US12/512,955 US8664455B2 (en) | 2008-08-08 | 2009-07-30 | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| US12/512,955 | 2009-07-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010043080A JP2010043080A (ja) | 2010-02-25 |
| JP2010043080A5 JP2010043080A5 (enExample) | 2014-05-15 |
| JP5595689B2 true JP5595689B2 (ja) | 2014-09-24 |
Family
ID=41059831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009184438A Expired - Fee Related JP5595689B2 (ja) | 2008-08-08 | 2009-08-07 | 2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)を製造するための改良法 |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US8664455B2 (enExample) |
| EP (1) | EP2151425B1 (enExample) |
| JP (1) | JP5595689B2 (enExample) |
| KR (1) | KR101619423B1 (enExample) |
| AT (1) | ATE512125T1 (enExample) |
| MX (1) | MX2009008451A (enExample) |
Families Citing this family (54)
| 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 |
| US8071825B2 (en) | 2006-01-03 | 2011-12-06 | 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 |
| 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 |
| US20170253545A1 (en) | 2007-01-03 | 2017-09-07 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US9670117B2 (en) | 2007-01-03 | 2017-06-06 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| WO2013067350A1 (en) * | 2011-11-04 | 2013-05-10 | Selma Bektesevic | Process for producing 2,3,3,3-tetrafluoropropene |
| US9493384B2 (en) | 2007-07-06 | 2016-11-15 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US9416074B2 (en) | 2007-07-06 | 2016-08-16 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| 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 |
| US8975454B2 (en) | 2008-07-31 | 2015-03-10 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| 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. |
| EP2534121B1 (en) * | 2010-02-12 | 2019-05-15 | Daikin Industries, Ltd. | Process for producing fluorine-containing alkene compound |
| HUE032122T2 (hu) * | 2010-03-10 | 2017-08-28 | Arkema France | Eljárás fluorozásra folyadékfázisban |
| 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) |
| US20110245548A1 (en) * | 2010-03-31 | 2011-10-06 | Honeywell International Inc. | Catalyst life improvement in the vapor phase fluorination of chlorocarbons |
| WO2011130108A1 (en) * | 2010-04-14 | 2011-10-20 | Arkema Inc. | Process for the manufacture of tetrafluoroolefins |
| JP6014584B2 (ja) * | 2010-04-26 | 2016-10-25 | アルケマ フランス | ペンタクロロプロパンの液相フッ素化による2−クロロ−3,3,3−トリフルオロプロペン(HCFO1233xf)の製造方法 |
| US8927791B2 (en) * | 2010-04-29 | 2015-01-06 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
| US8263817B2 (en) | 2010-07-06 | 2012-09-11 | E I Du Pont De Nemours And Company | Synthesis of 1234YF by selective dehydrochlorination of 244BB |
| 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 |
| EP2640681B1 (en) * | 2010-11-15 | 2017-10-18 | Arkema France | Process for the manufacture of 2-chloro-3,3,3-trifluoropropene (hcfo 1233xf) by liquid phase fluorination of pentachloropropane |
| US9890096B2 (en) * | 2011-01-19 | 2018-02-13 | Honeywell International Inc. | Methods of making 2,3,3,3-tetrafluoro-2-propene |
| EP2665693B1 (en) * | 2011-01-21 | 2017-07-19 | Arkema France | Catalytic gas phase fluorination |
| WO2013049743A1 (en) * | 2011-09-30 | 2013-04-04 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| MX348598B (es) * | 2011-09-30 | 2017-06-21 | Honeywell Int Inc | Proceso para producir 2,3,3,3 - tetrafluoropropeno. |
| 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 |
| JP6223346B2 (ja) * | 2011-10-14 | 2017-11-01 | 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. | 2,3,3,3−テトラフルオロプロペンの製造方法 |
| KR20140075790A (ko) * | 2011-10-14 | 2014-06-19 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜의 제조 방법 |
| CN104080759A (zh) * | 2011-10-14 | 2014-10-01 | 塞尔马·贝克特什维克 | 生产2,3,3,3-四氟丙烯的方法 |
| JP6518869B2 (ja) * | 2011-11-04 | 2019-05-29 | 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. | 2,3,3,3−テトラフルオロプロペンの製造方法 |
| WO2013071024A1 (en) * | 2011-11-10 | 2013-05-16 | Mario Joseph Nappa | Catalytic fluorination process of making hydrohaloalkane |
| IN2014DN06917A (enExample) | 2012-02-10 | 2015-05-15 | Haiyou Wang | |
| US9328043B2 (en) * | 2012-02-29 | 2016-05-03 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| GB201207666D0 (en) | 2012-05-02 | 2012-06-13 | Mexichem Amanco Holding Sa | Process |
| US20140215970A1 (en) * | 2013-02-04 | 2014-08-07 | Honeywell International Inc. | METHODS OF HANDLING CHLORINATED COMPOUNDS USED FOR MANUFACTURING HFO-1234yf |
| 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 |
| US9353029B2 (en) * | 2013-03-14 | 2016-05-31 | Honeywell International, Inc. | Fluorination process and reactor |
| MX2015011268A (es) * | 2013-03-15 | 2015-12-03 | Honeywell Int Inc | Proceso de fabricacion de 2-cloro-1,1,1,2-tetrafluoropropano (hcfc-244bb). |
| US20140275651A1 (en) * | 2013-03-15 | 2014-09-18 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US9233895B2 (en) | 2013-03-15 | 2016-01-12 | Honeywell International, Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| FR3003568B1 (fr) * | 2013-03-20 | 2018-06-29 | Arkema France | Composition comprenant hf et 3,3,3-trifluoro-2-chloropropene |
| MX2015014453A (es) * | 2013-04-18 | 2016-02-03 | Honeywell Int Inc | Sistema de reaccion y proceso para producir organicos fluorados. |
| JP6210073B2 (ja) * | 2015-01-21 | 2017-10-11 | ダイキン工業株式会社 | フルオロプロペンの製造方法 |
| KR102699589B1 (ko) * | 2015-05-21 | 2024-08-28 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | SbF5에 의한 1233xf의 244bb로의 히드로플루오린화 |
| JP7413275B2 (ja) * | 2018-01-09 | 2024-01-15 | アーカイブ オート インク | 車両データの取得およびアクセスシステム、および方法 |
| WO2019220463A1 (en) * | 2018-05-18 | 2019-11-21 | Srf Limited | Preparation of 2,3,3,3-tetrafluoropropene, intermediate and composition thereof |
| CN119118782A (zh) | 2018-06-06 | 2024-12-13 | 霍尼韦尔国际公司 | 用于HCFC-244bb的脱氯化氢以制备HFO-1234yf的方法 |
| CN112424152A (zh) * | 2018-07-18 | 2021-02-26 | 科慕埃弗西有限公司 | 绝热反应区中卤烯烃的产生 |
| FR3084359B1 (fr) | 2018-07-25 | 2021-11-26 | Arkema France | Procede de production et de purification du 2-chloro-1,1,1,2-tetrafluoropropane. |
| US20250197609A1 (en) | 2023-12-13 | 2025-06-19 | Blue Evolution, Inc. | Ecofriendly, biodegradable biological polysaccharide composition for packaging materials |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU36877A1 (enExample) | 1958-05-21 | |||
| US2931840A (en) | 1958-11-25 | 1960-04-05 | Du Pont | Process for preparing 2, 3, 3, 3-tetrafluoropropene |
| JPH01207250A (ja) | 1988-02-12 | 1989-08-21 | Daikin Ind Ltd | 含フツ素オレフインの製造方法 |
| US5155082A (en) | 1991-04-12 | 1992-10-13 | Allied-Signal Inc. | Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons |
| KR0125143B1 (ko) | 1994-12-02 | 1997-11-27 | 김은영 | 1,1,1-트리플루오로-2,2-디클로로에탄의 불소화 촉매 및 그것의 제조방법 |
| EP0939071B1 (en) | 1998-02-26 | 2003-07-30 | Central Glass Company, Limited | Method for producing fluorinated propane |
| BE1011765A3 (fr) | 1998-02-26 | 2000-01-11 | Solvay | Procede d'hydrofluoration d'hydrocarbures. |
| US6500795B2 (en) | 2001-01-24 | 2002-12-31 | Honeywell International Inc. | Azeotrope-like composition of 1-chloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
| US9005467B2 (en) | 2003-10-27 | 2015-04-14 | Honeywell International Inc. | Methods of replacing heat transfer fluids |
| US7592494B2 (en) | 2003-07-25 | 2009-09-22 | Honeywell International Inc. | Process for the manufacture of 1,3,3,3-tetrafluoropropene |
| CA2564903C (en) | 2004-04-29 | 2012-12-04 | Honeywell International Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene |
| 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 |
| US8084653B2 (en) * | 2004-04-29 | 2011-12-27 | 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) |
| ES2639623T5 (es) * | 2006-01-03 | 2024-10-04 | Honeywell Int Inc | Método para preparar compuestos orgánicos fluorados |
| US8071825B2 (en) | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8952208B2 (en) | 2006-01-03 | 2015-02-10 | Honeywell International Inc. | Method for prolonging a catalyst's life during hydrofluorination |
| US8034251B2 (en) | 2007-01-03 | 2011-10-11 | Honeywell International Inc. | Azeotropic compositions of 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), and hydrogen fluoride (HF) |
| KR101550250B1 (ko) | 2007-06-27 | 2015-09-04 | 알케마 인코포레이티드 | 하이드로플루오로올레핀의 제조 방법 |
| US9040759B2 (en) | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| US7795480B2 (en) | 2007-07-25 | 2010-09-14 | Honeywell International Inc. | Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) |
| US9035111B2 (en) | 2007-08-22 | 2015-05-19 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US20090224207A1 (en) | 2008-03-06 | 2009-09-10 | Pham Hang T | Azeotrope-Like Composition of 2-Chloro-3,3,3-Trifluoropropene (HCFC-1233xf) and Hydrogen Fluoride (HF) |
| 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 |
| US8252965B2 (en) | 2008-08-22 | 2012-08-28 | Honeywell International Inc. | Method for separating halocarbons |
-
2009
- 2009-07-30 US US12/512,955 patent/US8664455B2/en not_active Expired - Fee Related
- 2009-08-05 EP EP09167306A patent/EP2151425B1/en active Active
- 2009-08-05 AT AT09167306T patent/ATE512125T1/de not_active IP Right Cessation
- 2009-08-07 JP JP2009184438A patent/JP5595689B2/ja not_active Expired - Fee Related
- 2009-08-07 KR KR1020090073012A patent/KR101619423B1/ko not_active Expired - Fee Related
- 2009-08-07 MX MX2009008451A patent/MX2009008451A/es active IP Right Grant
-
2013
- 2013-09-09 US US14/021,256 patent/US9181151B2/en not_active Expired - Fee Related
-
2015
- 2015-11-09 US US14/936,160 patent/US10160703B2/en not_active Expired - Fee Related
-
2017
- 2017-02-21 US US15/437,956 patent/US10112879B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009008451A (es) | 2010-03-22 |
| EP2151425A2 (en) | 2010-02-10 |
| US10112879B2 (en) | 2018-10-30 |
| US20140012047A1 (en) | 2014-01-09 |
| US20170158585A1 (en) | 2017-06-08 |
| US9181151B2 (en) | 2015-11-10 |
| ATE512125T1 (de) | 2011-06-15 |
| EP2151425A3 (en) | 2010-03-31 |
| US8664455B2 (en) | 2014-03-04 |
| US20160214914A1 (en) | 2016-07-28 |
| KR20100019397A (ko) | 2010-02-18 |
| EP2151425B1 (en) | 2011-06-08 |
| US20100036179A1 (en) | 2010-02-11 |
| US10160703B2 (en) | 2018-12-25 |
| KR101619423B1 (ko) | 2016-05-10 |
| JP2010043080A (ja) | 2010-02-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5595689B2 (ja) | 2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)を製造するための改良法 | |
| JP6188767B2 (ja) | フッ化水素化中の触媒寿命を延ばす方法 | |
| CN101665403B (zh) | 生产2-氯-1,1,1,2-四氟丙烷(HCFC-244bb)的改进方法 | |
| JP6463329B2 (ja) | 2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)の製造方法 | |
| CN105188909B (zh) | 氟化方法与反应器 | |
| US9233895B2 (en) | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120731 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120731 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130925 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131001 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131227 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140108 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140401 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20140401 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140708 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140806 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5595689 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |