JP2010536776A - アルミニウム触媒を用いた１，２，３，３，３−ペンタフルオロプロペンのｅ異性体とｚ異性体間での触媒異性化 - Google Patents
アルミニウム触媒を用いた１，２，３，３，３−ペンタフルオロプロペンのｅ異性体とｚ異性体間での触媒異性化 Download PDFInfo
- Publication number
- JP2010536776A JP2010536776A JP2010521163A JP2010521163A JP2010536776A JP 2010536776 A JP2010536776 A JP 2010536776A JP 2010521163 A JP2010521163 A JP 2010521163A JP 2010521163 A JP2010521163 A JP 2010521163A JP 2010536776 A JP2010536776 A JP 2010536776A
- Authority
- JP
- Japan
- Prior art keywords
- pentafluoropropene
- ratio
- hfc
- starting material
- catalyst
- 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.)
- Pending
Links
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical class F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 title claims abstract description 53
- 239000003054 catalyst Substances 0.000 title claims abstract description 20
- 238000006317 isomerization reaction Methods 0.000 title description 15
- 230000003197 catalytic effect Effects 0.000 title description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title 1
- 229910052782 aluminium Inorganic materials 0.000 title 1
- 239000007858 starting material Substances 0.000 claims abstract description 24
- -1 aluminum chlorofluoride Chemical compound 0.000 claims abstract description 16
- 239000012467 final product Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 54
- 239000000047 product Substances 0.000 claims description 14
- 239000007791 liquid phase Substances 0.000 claims description 3
- DMUPYMORYHFFCT-OWOJBTEDSA-N (e)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(\F)C(F)(F)F DMUPYMORYHFFCT-OWOJBTEDSA-N 0.000 claims description 2
- 230000007423 decrease Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 12
- 230000003247 decreasing effect Effects 0.000 description 9
- 230000008901 benefit Effects 0.000 description 7
- 239000003507 refrigerant Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000788 chromium alloy Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229940124568 digestive agent Drugs 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95618507P | 2007-08-16 | 2007-08-16 | |
| PCT/US2008/073085 WO2009026080A1 (en) | 2007-08-16 | 2008-08-14 | Catalytic isomerization between e and z isomers of 1,2,3,3,3 pentafluoropropene using aluminum catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010536776A true JP2010536776A (ja) | 2010-12-02 |
| JP2010536776A5 JP2010536776A5 (enExample) | 2011-09-29 |
Family
ID=40122339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010521163A Pending JP2010536776A (ja) | 2007-08-16 | 2008-08-14 | アルミニウム触媒を用いた１，２，３，３，３−ペンタフルオロプロペンのｅ異性体とｚ異性体間での触媒異性化 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8058491B2 (enExample) |
| JP (1) | JP2010536776A (enExample) |
| CN (1) | CN101796003A (enExample) |
| WO (1) | WO2009026080A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010536777A (ja) * | 2007-08-16 | 2010-12-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アルミニウム触媒を用いた１，２，３，３，３−ペンタフルオロプロペンのｅ異性体とｚ異性体間での触媒異性化 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110009678A1 (en) * | 2007-09-13 | 2011-01-13 | Arkema Inc. | Compositions containing a combination of z and e stereoisomers of hydrofluoroolefins |
| US8710282B2 (en) * | 2008-03-14 | 2014-04-29 | Honeywell International Inc. | Integrated process for the manufacture of fluorinated olefins |
| CN112811975B (zh) * | 2021-04-22 | 2021-07-30 | 泉州宇极新材料科技有限公司 | 气相异构化制备z-1-r-3,3,3-三氟丙烯的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08500347A (ja) * | 1992-07-31 | 1996-01-16 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | １，１，２−トリクロロトリフルオロエタンの異性化方法 |
| WO2008008351A2 (en) * | 2006-07-13 | 2008-01-17 | E. I. Du Pont De Nemours And Company | Catalytic isomerization between e and z isomers of 1,2,3,3,3-pentafluoropropene |
| JP2010523635A (ja) * | 2007-04-11 | 2010-07-15 | イネオス、フラウアー、ホールディングス、リミテッド | （ヒドロハロ）フルオロアルケンを異性化する方法 |
| JP2010536777A (ja) * | 2007-08-16 | 2010-12-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アルミニウム触媒を用いた１，２，３，３，３−ペンタフルオロプロペンのｅ異性体とｚ異性体間での触媒異性化 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3398204A (en) * | 1965-08-26 | 1968-08-20 | Dow Chemical Co | Isomerization process |
| US3914167A (en) * | 1974-08-26 | 1975-10-21 | Dow Chemical Co | Process for making cis-1,3-dichloropropene |
| US5157171A (en) * | 1989-10-16 | 1992-10-20 | E. I. Du Pont De Nemours And Company | Process for chlorofluoropropanes |
| US5162594A (en) | 1990-10-11 | 1992-11-10 | E. I. Du Pont De Nemours And Company | Process for production of polyfluoroolefins |
| US5182594A (en) * | 1991-10-09 | 1993-01-26 | Hopson Talmadge W | CRT method of and apparatus for illuminating photographic negatives to produce a hard copy |
| EP0644173A1 (en) * | 1992-06-05 | 1995-03-22 | Daikin Industries, Limited | Processes for producing 1,1,1,2,3-pentafluoropropene and producing 1,1,1,2,3-pentafluoropropane |
| US5396000A (en) * | 1993-05-24 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,2,3,-pentafluoropropane |
| JP4031052B2 (ja) | 1997-01-31 | 2008-01-09 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ペンタフルオロプロペンの接触製造 |
| US6031141A (en) * | 1997-08-25 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Fluoroolefin manufacturing process |
| US6389284B1 (en) * | 1999-05-27 | 2002-05-14 | Qwest Communications International, Inc. | System and method for controlling wireless network access |
| JP4232506B2 (ja) * | 2002-06-24 | 2009-03-04 | 株式会社豊田自動織機 | 摺動部品 |
| ES2407430T3 (es) | 2003-01-07 | 2013-06-12 | Nanofluor Gmbh | Procedimiento para la preparación de fluoruros metálicos de elevada área superficial |
| US7563936B2 (en) | 2006-10-27 | 2009-07-21 | Honeywell International Inc | Processes for geometric isomerization of halogenated olefins |
-
2008
- 2008-08-14 CN CN200880103058A patent/CN101796003A/zh active Pending
- 2008-08-14 US US12/674,961 patent/US8058491B2/en not_active Expired - Fee Related
- 2008-08-14 JP JP2010521163A patent/JP2010536776A/ja active Pending
- 2008-08-14 WO PCT/US2008/073085 patent/WO2009026080A1/en not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08500347A (ja) * | 1992-07-31 | 1996-01-16 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | １，１，２−トリクロロトリフルオロエタンの異性化方法 |
| WO2008008351A2 (en) * | 2006-07-13 | 2008-01-17 | E. I. Du Pont De Nemours And Company | Catalytic isomerization between e and z isomers of 1,2,3,3,3-pentafluoropropene |
| JP2010523635A (ja) * | 2007-04-11 | 2010-07-15 | イネオス、フラウアー、ホールディングス、リミテッド | （ヒドロハロ）フルオロアルケンを異性化する方法 |
| JP2010536777A (ja) * | 2007-08-16 | 2010-12-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アルミニウム触媒を用いた１，２，３，３，３−ペンタフルオロプロペンのｅ異性体とｚ異性体間での触媒異性化 |
Non-Patent Citations (1)
| Title |
|---|
| JPN6012042298; Ｊｏｕｒｎａｌ ｏｆ Ｆｌｕｏｒｉｎｅ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．４４ ｎｏ．１, 1989, ｐ．１６７-１７４ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010536777A (ja) * | 2007-08-16 | 2010-12-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アルミニウム触媒を用いた１，２，３，３，３−ペンタフルオロプロペンのｅ異性体とｚ異性体間での触媒異性化 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20100197979A1 (en) | 2010-08-05 |
| WO2009026080A1 (en) | 2009-02-26 |
| CN101796003A (zh) | 2010-08-04 |
| US8058491B2 (en) | 2011-11-15 |
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