JP2010508294A5 - - Google Patents
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- JP2010508294A5 JP2010508294A5 JP2009534879A JP2009534879A JP2010508294A5 JP 2010508294 A5 JP2010508294 A5 JP 2010508294A5 JP 2009534879 A JP2009534879 A JP 2009534879A JP 2009534879 A JP2009534879 A JP 2009534879A JP 2010508294 A5 JP2010508294 A5 JP 2010508294A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorinated olefin
- fluorinated
- formula
- degree
- conversion
- 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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- 238000000034 method Methods 0.000 claims description 35
- 150000001336 alkenes Chemical class 0.000 claims description 31
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052736 halogen Chemical group 0.000 claims description 10
- 229910052739 hydrogen Chemical class 0.000 claims description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 238000003541 multi-stage reaction Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000005796 dehydrofluorination reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 2
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 2
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 2
- VRVIDSRWPUGFBU-UHFFFAOYSA-N 2-chloro-1,1,1-trifluoropropane Chemical compound CC(Cl)C(F)(F)F VRVIDSRWPUGFBU-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 229910001512 metal fluoride Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/588,464 US7560602B2 (en) | 2005-11-03 | 2006-10-27 | Process for manufacture of fluorinated olefins |
| US11/588,464 | 2006-10-27 | ||
| PCT/US2007/082601 WO2008057794A1 (en) | 2006-10-27 | 2007-10-26 | Process for the manufacture of fluorinated olefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010508294A JP2010508294A (ja) | 2010-03-18 |
| JP2010508294A5 true JP2010508294A5 (enExample) | 2010-12-16 |
| JP5588174B2 JP5588174B2 (ja) | 2014-09-10 |
Family
ID=39201461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009534879A Active JP5588174B2 (ja) | 2006-10-27 | 2007-10-26 | フッ素化オレフィンの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7560602B2 (enExample) |
| EP (1) | EP2076478B2 (enExample) |
| JP (1) | JP5588174B2 (enExample) |
| KR (2) | KR20090071510A (enExample) |
| CN (1) | CN101553453B (enExample) |
| ES (1) | ES2394870T5 (enExample) |
| RU (1) | RU2457195C2 (enExample) |
| WO (1) | WO2008057794A1 (enExample) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7880040B2 (en) * | 2004-04-29 | 2011-02-01 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8067649B2 (en) * | 2004-04-29 | 2011-11-29 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| CN101479217B (zh) * | 2006-06-27 | 2013-02-06 | 纳幕尔杜邦公司 | 四氟丙烯生产方法 |
| WO2008002499A2 (en) * | 2006-06-27 | 2008-01-03 | E. I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| US8263816B2 (en) | 2006-06-27 | 2012-09-11 | E I Du Pont De Nemours And Company | 1,2,3,3,3-Pentafluoropropene production processes |
| US8377327B2 (en) | 2006-06-27 | 2013-02-19 | E I Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| US8013194B2 (en) † | 2008-03-14 | 2011-09-06 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| EP4328213A3 (en) * | 2006-10-27 | 2024-04-03 | Honeywell International Inc. | A high purity 2,3,3,3-tetrafluoropropene |
| GB0625214D0 (en) * | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| US7884254B2 (en) * | 2007-08-08 | 2011-02-08 | Honeywell International Inc. | Dehydrochlorination of hydrochlorofluorocarbons using pre-treated activated carbon catalysts |
| US8044250B2 (en) * | 2007-11-16 | 2011-10-25 | Honeywell International Inc. | Manufacture of 1,1,1,2,3,3-hexafluoropropane and 1,1,1,2-tetrafluoropropane via catalytic hydrogenation |
| JP4849058B2 (ja) | 2007-11-21 | 2011-12-28 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| WO2009084703A1 (en) | 2007-12-27 | 2009-07-09 | Daikin Industries, Ltd. | Process for producing 1,1,1,2-tetrafluoropropene |
| GB0801209D0 (en) | 2008-01-23 | 2008-02-27 | Ineos Fluor Holdings Ltd | Process |
| JP5136111B2 (ja) * | 2008-02-19 | 2013-02-06 | セントラル硝子株式会社 | フルオロオレフィンとフッ化水素の分離方法 |
| US8710282B2 (en) | 2008-03-14 | 2014-04-29 | Honeywell International Inc. | Integrated process for the manufacture of fluorinated olefins |
| FR2929272B1 (fr) * | 2008-03-28 | 2010-04-09 | Arkema France | Procede pour la preparation du 2,3,3,3-tetrafluoro-1-propene |
| RU2010149957A (ru) | 2008-05-07 | 2012-06-20 | Е.И. Дюпон Де Немур Энд Компани (Us) | Композиции, включающие 1,1,1,2,3-пентафторпропан или 2,3,3,3-тетрафторпропен |
| GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
| FR2935703B1 (fr) * | 2008-09-11 | 2010-09-03 | Arkema France | Procede de preparation de composes fluores. |
| US8609909B2 (en) * | 2009-01-30 | 2013-12-17 | Honeywell International Inc. | Process for the purification of hydrofluoroolefins |
| 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 |
| US7985884B2 (en) * | 2009-06-03 | 2011-07-26 | E. I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
| FR2948362B1 (fr) * | 2009-07-23 | 2012-03-23 | Arkema France | Procede de preparation de composes fluores |
| FR2948361B1 (fr) | 2009-07-23 | 2011-08-05 | Arkema France | Procede de preparation de composes fluores |
| CN101628850B (zh) * | 2009-08-14 | 2012-09-19 | 西安近代化学研究所 | Z-1,2,3,3,3-五氟丙烯的制备方法 |
| CN101628849B (zh) * | 2009-08-14 | 2012-10-10 | 西安近代化学研究所 | Z-1,2,3,3,3-五氟丙烯的制备方法 |
| US8129574B2 (en) * | 2009-08-31 | 2012-03-06 | Honeywell International Inc. | Hydrogenation process for fluorocarbons |
| US8158549B2 (en) | 2009-09-04 | 2012-04-17 | Honeywell International Inc. | Catalysts for fluoroolefins hydrogenation |
| JP2013527273A (ja) | 2010-04-16 | 2013-06-27 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ２，３，３，３−テトラフルオロプロペンおよび１，１，１，２−テトラフルオロエタンを含んでなる組成物、それを含有する冷却装置、およびその中で冷却を生じる方法 |
| US20110269999A1 (en) | 2010-04-29 | 2011-11-03 | Honeywell International Inc. | Process for dehydrohalogenation of halogenated alkanes |
| US8436218B2 (en) * | 2010-05-27 | 2013-05-07 | Honeywell International Inc. | Azeotrope-like composition of hexafluoropropane, hexafluoropropene and hydrogen fluoride |
| US8513474B2 (en) | 2010-06-24 | 2013-08-20 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| 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 |
| JP5434970B2 (ja) * | 2010-07-12 | 2014-03-05 | セントラル硝子株式会社 | ドライエッチング剤 |
| US8680345B2 (en) | 2011-01-07 | 2014-03-25 | Honeywell International Inc. | Low temperature production of 2-chloro-3,3,3-trifluoropropene |
| CN103328424A (zh) | 2011-02-04 | 2013-09-25 | 旭硝子株式会社 | 2,3,3,3-四氟丙烯的纯化方法 |
| TW201247315A (en) | 2011-05-16 | 2012-12-01 | Du Pont | Catalytic hydrogenation of fluoroolefins, alpha-alumina supported palladium compositions and their use as hydrogenation catalysts |
| JP6034653B2 (ja) * | 2012-10-22 | 2016-11-30 | 住友精化株式会社 | パラフィンの製造方法 |
| CN103073386B (zh) * | 2012-12-31 | 2014-08-20 | 浙江衢化氟化学有限公司 | 一种2,3,3,3-四氟丙烯的制备方法 |
| US9272968B2 (en) | 2013-03-14 | 2016-03-01 | Honeywell International Inc. | Process to suppress the formation of 3,3,3-trifluoropropyne in fluorocarbon manufacture |
| US9290424B2 (en) | 2013-03-14 | 2016-03-22 | Honeywell International Inc. | Processes for the hydrogenation of halogenated alkenes and the manufacture of fluorinated olefins |
| KR101500655B1 (ko) | 2013-09-17 | 2015-03-12 | 한국과학기술연구원 | 금속불소화물 촉매 제조방법 및 이를 이용한 탈불산화 방법 |
| CN110240535B (zh) | 2014-08-14 | 2022-09-13 | 科慕埃弗西有限公司 | 通过脱氟化氢来制备E-1,3,3,3-四氟丙烯(HFC-1234ze)的方法 |
| FR3033791B1 (fr) | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| JP6623561B2 (ja) * | 2015-05-29 | 2019-12-25 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| US10738001B2 (en) | 2015-06-05 | 2020-08-11 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| GB201512510D0 (en) | 2015-07-17 | 2015-08-19 | Mexichem Fluor Sa De Cv | Process |
| GB2540427B (en) | 2015-07-17 | 2017-07-19 | Mexichem Fluor Sa De Cv | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| KR20160017661A (ko) | 2016-01-29 | 2016-02-16 | 한국과학기술연구원 | 헥사플루오로프로필렌으로부터 2,3,3,3-테트라플루오로프로펜과 1,3,3,3-테트라플루오로프로펜의 제조방법 |
| KR101914236B1 (ko) | 2017-01-11 | 2018-12-28 | 한국과학기술연구원 | 1,2,3,3,3-펜타플루오로프로펜 제조방법 |
| JP6624126B2 (ja) * | 2017-03-13 | 2019-12-25 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| 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 |
| CN113195443A (zh) * | 2018-12-19 | 2021-07-30 | 大金工业株式会社 | 氟代乙烷的制造方法和氟代烯烃的制造方法 |
| JP6835060B2 (ja) * | 2018-12-27 | 2021-02-24 | ダイキン工業株式会社 | シクロブテンの製造方法 |
| CN111558386B (zh) * | 2020-04-10 | 2023-05-12 | 西安近代化学研究所 | 气相氟化合成氢氟烯烃用氟化铁基催化剂及其制备方法和应用 |
| WO2022218204A1 (zh) | 2021-04-15 | 2022-10-20 | 浙江省化工研究院有限公司 | 制备2,3,3,3-四氟丙烯的方法 |
| CN116874345B (zh) * | 2023-09-06 | 2024-08-06 | 北京宇极科技发展有限公司 | 气相连续制备e-1,1,1,4,5,5,5-七氟-4-(三氟甲基)戊-2-烯的方法 |
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| US4033899A (en) * | 1974-12-30 | 1977-07-05 | Texaco Inc. | Alkylation fluosulfonic-sulfuric acid catalyst recovery process with silica-alumina removal of fluoride compounds |
| US4138355A (en) * | 1976-08-10 | 1979-02-06 | Halocarbon Products Corporation | Fluorine substitution in 1,1,1-trihalomethanes |
| US5334783A (en) * | 1988-03-14 | 1994-08-02 | Hoechst Aktiengesellschaft | Process for the preparation of hexafluoropropene |
| RU2026279C1 (ru) * | 1989-02-03 | 1995-01-09 | Е.И.Дюпон Де Немур Энд Компани | Способ гидрогенолиза и/или дегидрогалогенирования фторгалоуглеродов и/или фторгалоуглеводородов |
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| ES2543408T3 (es) * | 2004-04-29 | 2015-08-19 | Honeywell International Inc. | Procedimiento para síntesis de 1,3,3,3-tetrafluoropropeno |
| CN1976885B (zh) * | 2004-04-29 | 2010-05-26 | 霍尼韦尔国际公司 | 1,3,3,3-四氟丙烯和2,3,3,3-四氟丙烯的合成方法 |
| 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 |
| US20060106262A1 (en) * | 2004-11-18 | 2006-05-18 | Optimer Photonics, Inc. | Electrooptic chromophores with large optical birefringence for applications at high speed and short wavelengths |
| US8044250B2 (en) † | 2007-11-16 | 2011-10-25 | Honeywell International Inc. | Manufacture of 1,1,1,2,3,3-hexafluoropropane and 1,1,1,2-tetrafluoropropane via catalytic hydrogenation |
-
2006
- 2006-10-27 US US11/588,464 patent/US7560602B2/en active Active
-
2007
- 2007-10-26 ES ES07863530T patent/ES2394870T5/es active Active
- 2007-10-26 JP JP2009534879A patent/JP5588174B2/ja active Active
- 2007-10-26 KR KR1020087012977A patent/KR20090071510A/ko not_active Ceased
- 2007-10-26 KR KR1020147017940A patent/KR20140090702A/ko not_active Ceased
- 2007-10-26 WO PCT/US2007/082601 patent/WO2008057794A1/en not_active Ceased
- 2007-10-26 EP EP07863530.7A patent/EP2076478B2/en active Active
- 2007-10-26 CN CN2007800400996A patent/CN101553453B/zh active Active
- 2007-10-26 RU RU2008122213/04A patent/RU2457195C2/ru not_active IP Right Cessation
-
2009
- 2009-02-19 US US12/389,110 patent/US7786333B2/en active Active
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