RU2451659C2 - Способы каталитического получения гексафторпропенов - Google Patents
Способы каталитического получения гексафторпропенов Download PDFInfo
- Publication number
- RU2451659C2 RU2451659C2 RU2009104933/04A RU2009104933A RU2451659C2 RU 2451659 C2 RU2451659 C2 RU 2451659C2 RU 2009104933/04 A RU2009104933/04 A RU 2009104933/04A RU 2009104933 A RU2009104933 A RU 2009104933A RU 2451659 C2 RU2451659 C2 RU 2451659C2
- Authority
- RU
- Russia
- Prior art keywords
- hfc
- catalyst
- minutes
- reactor
- sccm
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title abstract description 12
- 230000003197 catalytic effect Effects 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 53
- SUAMPXQALWYDBK-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluoropropane Chemical compound FCC(F)(F)C(F)(F)F SUAMPXQALWYDBK-UHFFFAOYSA-N 0.000 claims abstract description 16
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims abstract description 15
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims abstract 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 abstract description 5
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 44
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 claims description 28
- 239000011651 chromium Substances 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 239000011261 inert gas Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 12
- 229910000423 chromium oxide Inorganic materials 0.000 description 9
- 230000008901 benefit Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003507 refrigerant Substances 0.000 description 7
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 6
- 238000004508 fractional distillation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000005796 dehydrofluorination reaction Methods 0.000 description 5
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 229910001026 inconel Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical class FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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
- 229910000831 Steel Inorganic materials 0.000 description 2
- JOSWYUNQBRPBDN-UHFFFAOYSA-P ammonium dichromate Chemical compound [NH4+].[NH4+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JOSWYUNQBRPBDN-UHFFFAOYSA-P 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- 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 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004279 X-ray Guinier Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000000788 chromium alloy Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 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
- 239000003989 dielectric material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- -1 heat transfer media Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/132—Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/22—Halogenating
- B01J37/26—Fluorinating
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83093906P | 2006-07-13 | 2006-07-13 | |
| US60/830,939 | 2006-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009104933A RU2009104933A (ru) | 2010-08-20 |
| RU2451659C2 true RU2451659C2 (ru) | 2012-05-27 |
Family
ID=38645716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009104933/04A RU2451659C2 (ru) | 2006-07-13 | 2007-07-11 | Способы каталитического получения гексафторпропенов |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7982073B2 (enExample) |
| EP (3) | EP2386534A1 (enExample) |
| JP (1) | JP5764291B2 (enExample) |
| CN (2) | CN101489960B (enExample) |
| ES (1) | ES2523694T3 (enExample) |
| RU (1) | RU2451659C2 (enExample) |
| WO (1) | WO2008008350A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8377327B2 (en) * | 2006-06-27 | 2013-02-19 | E I Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| CN101578252B (zh) * | 2006-09-05 | 2013-11-27 | 纳幕尔杜邦公司 | 1,2,3,3,3-五氟丙烯生产方法 |
| KR101397113B1 (ko) | 2006-10-03 | 2014-05-19 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| CN103553871A (zh) * | 2006-10-31 | 2014-02-05 | 纳幕尔杜邦公司 | 氟丙烷、卤代丙烯以及2-氯-3,3,3-三氟-1-丙烯与hf的共沸组合物和1,1,1,2,2-五氟丙烷与hf的共沸组合物的制备方法 |
| FR2932799B1 (fr) * | 2008-06-18 | 2010-08-13 | Arkema France | Procede de preparation de composes fluores |
| US8487145B2 (en) | 2009-06-03 | 2013-07-16 | E I De Pont De Nemours And Company | Catalysts and process to manufacture 2,3,3,3-tetrafluoropropene |
| MX2011012774A (es) | 2009-06-03 | 2012-01-20 | Du Pont | Catalizadores y proceso para la fabricacion de 2,3,3,3-tetrafluoropropeno. |
| WO2011077192A1 (en) | 2009-12-23 | 2011-06-30 | Arkema France | CATALYTIC GAS PHASE FLUORINATION OF 1233xf TO 1234yf |
| JP5984796B2 (ja) | 2010-05-03 | 2016-09-06 | アーケマ・インコーポレイテッド | ペンタフルオロアルカンの脱フッ化水素化反応によるテトラフルオロオレフィンの形成 |
| US8513474B2 (en) * | 2010-06-24 | 2013-08-20 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| US8263817B2 (en) * | 2010-07-06 | 2012-09-11 | E I Du Pont De Nemours And Company | Synthesis of 1234YF by selective dehydrochlorination of 244BB |
| US9724684B2 (en) * | 2011-02-21 | 2017-08-08 | The Chemours Company Fc, Llc | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
| GB2492847A (en) * | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| CN104024189B (zh) * | 2011-12-28 | 2016-01-13 | 旭硝子株式会社 | 2,3,3,3-四氟丙烯的纯化方法，纯化装置及制造方法 |
| GB201207666D0 (en) | 2012-05-02 | 2012-06-13 | Mexichem Amanco Holding Sa | Process |
| KR101500655B1 (ko) * | 2013-09-17 | 2015-03-12 | 한국과학기술연구원 | 금속불소화물 촉매 제조방법 및 이를 이용한 탈불산화 방법 |
| GB2519572B (en) | 2013-10-25 | 2015-12-30 | Mexichem Amanco Holding Sa | Process for isomerising (hydro)(halo)fluoroalkenes |
| MX383780B (es) * | 2014-02-13 | 2025-03-14 | Fram Group Ip Llc | Composición y método para la fabricación de un aislante para una bujía. |
| US9302962B2 (en) | 2014-08-14 | 2016-04-05 | The Chemours Company Fc, Llc | Dehydrofluorination of 245fa to 1234ze |
| GB2540427B (en) | 2015-07-17 | 2017-07-19 | Mexichem Fluor Sa De Cv | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| GB201615209D0 (en) | 2016-09-07 | 2016-10-19 | Mexichem Fluor Sa De Cv | Catalyst and process using the catalyst |
| GB201615197D0 (en) | 2016-09-07 | 2016-10-19 | Mexichem Fluor Sa De Cv | Catalyst and process using the catalyst |
| CN108014827A (zh) * | 2017-12-12 | 2018-05-11 | 西安近代化学研究所 | 一种高比表面纳米氟氧铬催化剂的制备方法 |
| GB2580623A (en) | 2019-01-17 | 2020-07-29 | Mexichem Fluor Sa De Cv | Method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2461523A (en) * | 1946-12-04 | 1949-02-15 | Du Pont | Dehydrofluorination of polyfluoroalkanes |
| EP0234002A1 (en) * | 1986-01-22 | 1987-09-02 | ATOCHEM NORTH AMERICA, INC. (a Pennsylvania corp.) | Process for converting a 1,1,1-trifluoroalkane into a 1,1-difluoroalkene |
| EP0726243A1 (en) * | 1992-06-05 | 1996-08-14 | Daikin Industries, Limited | Method for manufacturing 1,1,1,2,3-pentafluoropropene and method for manufacturing 1,1,1,2,3-pentafluoropropane |
| RU2005115867A (ru) * | 2002-10-25 | 2006-01-10 | Ханивелл Интернэшнл, Инк. (Us) | Композиции, содержащие фторзамещенные олефины |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258500A (en) | 1959-08-17 | 1966-06-28 | Du Pont | Process for fluorinating halohydro-carbons |
| US4828818A (en) | 1987-03-13 | 1989-05-09 | Allied-Signal Inc. | Chromium aerogel method of producing same and fluorinating process utilizing same |
| US5036036A (en) | 1989-06-13 | 1991-07-30 | E. I. Du Pont De Nemours And Company | Chromium oxide catalyst composition |
| 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 |
| JP4378779B2 (ja) * | 1998-07-17 | 2009-12-09 | ダイキン工業株式会社 | 含フッ素エタンの製造方法 |
| US6124510A (en) * | 1998-07-21 | 2000-09-26 | Elf Atochem North America, Inc. | 1234ze preparation |
| KR20070011554A (ko) * | 2004-04-29 | 2007-01-24 | 허니웰 인터내셔널 인코포레이티드 | 1,3,3,3-테트라플루오로프로펜의 합성 방법 |
| US7897823B2 (en) * | 2004-10-29 | 2011-03-01 | E. I. Du Pont De Nemours And Company | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes |
| US7476771B2 (en) | 2005-11-01 | 2009-01-13 | E.I. Du Pont De Nemours + Company | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US7423188B2 (en) | 2005-11-01 | 2008-09-09 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising E-1,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US7388117B2 (en) | 2005-11-01 | 2008-06-17 | E.I. Du Pont De Nemours And Company | Azeotrope compositions comprising 1,2,3,3,3-pentafluoropropene and hydrogen fluoride and uses thereof |
| US7722781B2 (en) | 2006-06-27 | 2010-05-25 | E.I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| US7420094B2 (en) * | 2006-09-05 | 2008-09-02 | E.I. Du Pont De Nemours And Company | Catalytic isomerization processes of 1,3,3,3-tetrafluoropropene for making 2,3,3,3-tetrafluoropropene |
-
2007
- 2007-07-11 CN CN200780026549.6A patent/CN101489960B/zh active Active
- 2007-07-11 CN CN201210144189.2A patent/CN102690165B/zh active Active
- 2007-07-11 ES ES07796773.5T patent/ES2523694T3/es active Active
- 2007-07-11 WO PCT/US2007/015751 patent/WO2008008350A2/en not_active Ceased
- 2007-07-11 EP EP11005073A patent/EP2386534A1/en not_active Ceased
- 2007-07-11 EP EP07796773.5A patent/EP2041054B1/en active Active
- 2007-07-11 JP JP2009519495A patent/JP5764291B2/ja active Active
- 2007-07-11 EP EP11005072A patent/EP2386533A1/en not_active Withdrawn
- 2007-07-11 RU RU2009104933/04A patent/RU2451659C2/ru not_active IP Right Cessation
- 2007-07-11 US US12/373,594 patent/US7982073B2/en active Active
-
2011
- 2011-06-03 US US13/152,405 patent/US8148586B2/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2461523A (en) * | 1946-12-04 | 1949-02-15 | Du Pont | Dehydrofluorination of polyfluoroalkanes |
| EP0234002A1 (en) * | 1986-01-22 | 1987-09-02 | ATOCHEM NORTH AMERICA, INC. (a Pennsylvania corp.) | Process for converting a 1,1,1-trifluoroalkane into a 1,1-difluoroalkene |
| EP0726243A1 (en) * | 1992-06-05 | 1996-08-14 | Daikin Industries, Limited | Method for manufacturing 1,1,1,2,3-pentafluoropropene and method for manufacturing 1,1,1,2,3-pentafluoropropane |
| US5679875A (en) * | 1992-06-05 | 1997-10-21 | Daikin Industries, Ltd. | Method for manufacturing 1,1,1,2,3-pentafluoropropene 1,1,1,2,3-pentafluoropropane |
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Also Published As
| Publication number | Publication date |
|---|---|
| US8148586B2 (en) | 2012-04-03 |
| JP2009542812A (ja) | 2009-12-03 |
| JP5764291B2 (ja) | 2015-08-19 |
| US20100004492A1 (en) | 2010-01-07 |
| RU2009104933A (ru) | 2010-08-20 |
| CN101489960A (zh) | 2009-07-22 |
| EP2041054A2 (en) | 2009-04-01 |
| CN101489960B (zh) | 2014-03-05 |
| US7982073B2 (en) | 2011-07-19 |
| ES2523694T3 (es) | 2014-11-28 |
| CN102690165B (zh) | 2015-08-19 |
| EP2041054B1 (en) | 2014-08-27 |
| WO2008008350A2 (en) | 2008-01-17 |
| CN102690165A (zh) | 2012-09-26 |
| US20110237845A1 (en) | 2011-09-29 |
| WO2008008350A3 (en) | 2008-03-13 |
| EP2386533A1 (en) | 2011-11-16 |
| EP2386534A1 (en) | 2011-11-16 |
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