JP2015502390A - フッ素化オレフィン化合物の調製方法 - Google Patents
フッ素化オレフィン化合物の調製方法 Download PDFInfo
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- JP2015502390A JP2015502390A JP2014548136A JP2014548136A JP2015502390A JP 2015502390 A JP2015502390 A JP 2015502390A JP 2014548136 A JP2014548136 A JP 2014548136A JP 2014548136 A JP2014548136 A JP 2014548136A JP 2015502390 A JP2015502390 A JP 2015502390A
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- catalyst
- propene
- ccl
- oxygen
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- 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
- 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
- C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
- C07C17/158—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of 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
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/26—Chromium
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- 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)
Abstract
Description
ct(s.g/cm3)=(W/F)×(273/(273+T))×((101325+P)/101325)
(式中、Wは流動床中の触媒の量をグラムで表し、Fは標準温度及び標準圧力条件下のガス流の速度を表し、Tは反応温度を℃で表し、Pは圧力をパスカルで表す)により本発明において定義された反応物を含むガス混合物と触媒の間の接触時間(ct)は、好ましくは1〜50秒の間、及び有利には2〜40秒の間である。
Lv(cm/秒)=F×((273+T)/273)×(101325/(101325+P)×S)(式中、F、T及びPは上記のように定義され、Sは反応器の内部断面の面積(cm2)−空塔線速度としても知られる−である)により本発明において定義された、流動床反応器に導入される反応物を含むガス流の線速度は、好ましくは0.5〜200cm/秒の間、及び有利には1〜100cm/秒の間である。
Claims (10)
- 流動床反応器において懸濁液中に保持されたフッ素化触媒及び分子状酸素の存在下、HFによる、並びに式CX3CHClCH2Xのハロプロパン、及び式CX3CCl=CH2、CClX2CCl=CH2、CX2=CClCH2Xのハロプロペン(Xは、独立にフッ素原子又は塩素原子を表す)から選択される少なくとも1つの化合物の気相フッ素化の少なくとも1つの段階を含む、2,3,3,3−テトラフルオロ−1−プロペンの製造方法。
- 前記分子状酸素が、空気、富化空気又は高純度酸素の形態であることを特徴とする、請求項1に記載の方法。
- 前記ハロプロパンが、2,3−ジクロロ−1,1,1−トリフルオロプロパン及び/又は1,1,1,2,3−ペンタクロロプロパンから選択されることを特徴とする、請求項1又は2に記載の方法。
- 式CX3CCl=CH2の前記ハロプロペンが、2−クロロ−3,3,3−トリフルオロ−1−プロペンから選択されることを特徴とする、請求項1又は2に記載の方法。
- 酸素:フッ素化される化合物モル比が0.01〜1の間、好ましくは0.05〜0.2の間であることを特徴とする、請求項1から4の何れか一項に記載の方法。
- 反応物を含むガス混合物と前記触媒の間の接触時間が、1〜50秒の間であることを特徴とする、請求項1から5の何れか一項に記載の方法。
- 前記触媒が、クロム又は担持されていてもよいクロムを含む混合触媒をベースとすることを特徴とする、請求項1から6の何れか一項に記載の方法。
- 前記触媒粒子の平均径が、20〜200ミクロンの間であることを特徴とする、請求項7に記載の方法。
- 前記触媒が活性化段階に供されることを特徴とする、請求項1から8の何れか一項に記載の方法。
- 前記反応物の流れが、前記反応器に接線方向に注入されることを特徴とする、請求項1から9の何れか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1162314A FR2984886B1 (fr) | 2011-12-22 | 2011-12-22 | Procede de preparation de composes olefiniques fluores |
FR1162314 | 2011-12-22 | ||
PCT/FR2012/052752 WO2013093272A1 (fr) | 2011-12-22 | 2012-11-29 | Procédé de préparation de composes oléfiniques fluores |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015502390A true JP2015502390A (ja) | 2015-01-22 |
JP5988516B2 JP5988516B2 (ja) | 2016-09-07 |
Family
ID=47436093
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014548136A Expired - Fee Related JP5988516B2 (ja) | 2011-12-22 | 2012-11-29 | フッ素化オレフィン化合物の調製方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9187387B2 (ja) |
EP (1) | EP2794527B8 (ja) |
JP (1) | JP5988516B2 (ja) |
CN (1) | CN104010999B (ja) |
ES (1) | ES2645748T3 (ja) |
FR (1) | FR2984886B1 (ja) |
WO (1) | WO2013093272A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016222619A (ja) * | 2015-06-02 | 2016-12-28 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9975824B2 (en) * | 2014-09-30 | 2018-05-22 | Daikin Industries, Ltd. | Method for producing 2,3,3,3-tetrafluoropropene |
KR20180000720A (ko) | 2015-05-21 | 2018-01-03 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | SbF5에 의한 1233xf의 244bb로의 히드로플루오린화 |
CN116037119B (zh) * | 2023-03-31 | 2023-07-07 | 北京宇极科技发展有限公司 | 引发剂、氟化催化剂、气相连续反应制备氢氟烯烃的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2010531897A (ja) * | 2007-06-27 | 2010-09-30 | アーケマ・インコーポレイテッド | ヒドロフルオロオレフィンを製造する2段階法 |
WO2010123154A2 (en) * | 2009-04-23 | 2010-10-28 | Daikin Industries, Ltd. | Process for preparation of 2,3,3,3-tetrafluoropropene |
WO2011099605A2 (en) * | 2010-02-12 | 2011-08-18 | Daikin Industries, Ltd. | Process for producing fluorine-containing alkene compound |
WO2011130108A1 (en) * | 2010-04-14 | 2011-10-20 | Arkema Inc. | Process for the manufacture of tetrafluoroolefins |
Family Cites Families (13)
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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 |
KR101349634B1 (ko) | 2005-11-03 | 2014-01-09 | 허니웰 인터내셔널 인코포레이티드 | 플루오르화된 유기 화합물의 제조 방법 |
EP2546225B1 (en) | 2006-01-03 | 2017-12-20 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
KR101394583B1 (ko) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
US8398882B2 (en) | 2006-10-31 | 2013-03-19 | E I Du Pont De Nemours And Company | Processes for the production of fluoropropanes and halopropenes and azeotropic compositions of 2-chloro-3,3,3-trifluoro-1-propene with HF and of 1,1,1,2,2-pentafluoropropane with HF |
GB0625214D0 (en) | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
US8563789B2 (en) * | 2007-06-27 | 2013-10-22 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
JP5003822B2 (ja) | 2007-12-27 | 2012-08-15 | ダイキン工業株式会社 | 1,1,1,2−テトラフルオロプロペンの製造方法 |
CN101215220A (zh) * | 2008-01-16 | 2008-07-09 | 西安近代化学研究所 | 1,1,1,3-四氟丙烯的制备方法 |
US8252965B2 (en) * | 2008-08-22 | 2012-08-28 | Honeywell International Inc. | Method for separating halocarbons |
PL2516366T3 (pl) * | 2009-12-23 | 2017-04-28 | Arkema France | Katalityczne fluorowanie 1233xf do 1234yf w fazie gazowej |
US20110245548A1 (en) | 2010-03-31 | 2011-10-06 | Honeywell International Inc. | Catalyst life improvement in the vapor phase fluorination of chlorocarbons |
CN102001911B (zh) | 2010-09-20 | 2013-09-25 | 西安近代化学研究所 | 2,3,3,3-四氟丙烯的制备方法 |
-
2011
- 2011-12-22 FR FR1162314A patent/FR2984886B1/fr not_active Expired - Fee Related
-
2012
- 2012-11-29 WO PCT/FR2012/052752 patent/WO2013093272A1/fr active Application Filing
- 2012-11-29 US US14/366,853 patent/US9187387B2/en not_active Expired - Fee Related
- 2012-11-29 ES ES12806596.8T patent/ES2645748T3/es active Active
- 2012-11-29 CN CN201280063297.5A patent/CN104010999B/zh not_active Expired - Fee Related
- 2012-11-29 EP EP12806596.8A patent/EP2794527B8/fr not_active Not-in-force
- 2012-11-29 JP JP2014548136A patent/JP5988516B2/ja not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010531897A (ja) * | 2007-06-27 | 2010-09-30 | アーケマ・インコーポレイテッド | ヒドロフルオロオレフィンを製造する2段階法 |
WO2010123154A2 (en) * | 2009-04-23 | 2010-10-28 | Daikin Industries, Ltd. | Process for preparation of 2,3,3,3-tetrafluoropropene |
WO2011099605A2 (en) * | 2010-02-12 | 2011-08-18 | Daikin Industries, Ltd. | Process for producing fluorine-containing alkene compound |
WO2011130108A1 (en) * | 2010-04-14 | 2011-10-20 | Arkema Inc. | Process for the manufacture of tetrafluoroolefins |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016222619A (ja) * | 2015-06-02 | 2016-12-28 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
US9856191B2 (en) | 2015-06-02 | 2018-01-02 | Daikin Industries, Ltd. | Process for producing fluorine-containing olefin |
Also Published As
Publication number | Publication date |
---|---|
US9187387B2 (en) | 2015-11-17 |
FR2984886B1 (fr) | 2013-12-20 |
FR2984886A1 (fr) | 2013-06-28 |
ES2645748T3 (es) | 2017-12-07 |
CN104010999A (zh) | 2014-08-27 |
EP2794527A1 (fr) | 2014-10-29 |
JP5988516B2 (ja) | 2016-09-07 |
CN104010999B (zh) | 2016-01-06 |
EP2794527B8 (fr) | 2017-11-29 |
EP2794527B1 (fr) | 2017-10-04 |
WO2013093272A1 (fr) | 2013-06-27 |
US20140364658A1 (en) | 2014-12-11 |
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