JP2012529481A - ペンタフルオロプロパンの製造方法 - Google Patents
ペンタフルオロプロパンの製造方法 Download PDFInfo
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- JP2012529481A JP2012529481A JP2012514512A JP2012514512A JP2012529481A JP 2012529481 A JP2012529481 A JP 2012529481A JP 2012514512 A JP2012514512 A JP 2012514512A JP 2012514512 A JP2012514512 A JP 2012514512A JP 2012529481 A JP2012529481 A JP 2012529481A
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- pentafluoropropane
- pentafluoropropene
- hydrogen
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims abstract description 22
- 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 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007789 gas Substances 0.000 claims abstract description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- 230000003134 recirculating effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- -1 olefin compound Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
【解決手段】反応器中で水素化触媒の存在下に超化学量論量で気相の1,2,3,3,3-ペンタフルオロプロペンを水素と反応させ、反応器から出てくるガス状排出物の一部を再循環する、1,2,3,3,3-ペンタフルオロプロパンの製造方法。
Description
本発明方法を用いることによって、水素化反応の発熱性を制御でき、および/または、HFC-245ebの水素化反応を制限でき、および/または、触媒の非活性化を減らすことができる。
(i)1,2,3,3,3-ペンタフルオロプロペンを、反応器中で水素化触媒の存在下に、80〜250℃、好ましくは110〜160℃の温度で、超化学量論量で、水素と気相で反応させ、
(ii)1,1,1,2,3-ペンタフルオロプロパンと、未反応水素と、場合によって生じる未反応1,2,3,3,3-ペンタフルオロプロペン、1,1,1,2-テトラフルオロプロパンおよびフッ化水素酸とを含む、反応器からのガス状排出物の一部を再循環し、
(iii)反応器からのガス状排出物の残りの部分から、必要に応じて精製段階を実施した後に、1,1,1,2,3-ペンタフルオロプロパンを回収する。
反応器への循環流および反応物は反応器に導入する前に予備加熱できる。
本発明の水素化反応は0.5〜20バールの絶対圧力、有利には1〜5バールの絶対圧力で行うのが好ましい。
本発明の方法では、断熱反応器を用いるのが好ましい。
本発明の特に好ましい触媒はアルミナをベースにした担体上にパラジウムを含む触媒である。触媒中のパラジウムの量は、0.05〜10重量%、有利には0.1〜5重量%であるのが好ましい。
触媒の比表面積は4m2/g以上であるのが好ましい。触媒担体として用いるアルミナはα多形相で提供されるのが有利である。
変換率は変換されたHFO-1225yeの百分率で定義される。
生成物Xの選択率は、変換されたHFO-1225yeのモル数に対する生成した生成物Xのモル数の百分率で定義される。
469gの触媒を収容した内径が2.1cmで、長さが120cm(すなわち320cm3)の固定床の形をしたステンレス鋼製の管状反応器を用いた。触媒は0.2重量%の、α−アルミナに担持されたパラジウムを含む。
反応時間中に、1.41モル/時の水素と、0.7モル/時の1,2,3,3,3-ペンタフルオロプロペンとを連続注入し、再循環ループの流量は0.490Sm3/時(すなわち反応器出口のガス状排出物の93.7容量%)にした。触媒床入口の水素/HFO-1225yeモル比は16である。圧力は1バールの絶対圧力である。反応器入口の温度は60℃で、反応中に得られる最高反応器温度は124℃である。接触時間は2.3秒である。
得られたHFO-1225yeの変換率は100%、HFC-245ebの選択率は95.7%、HFC-254ebの選択率は4.1%である。80時間の運転中に非活性化は観察されなかった。
上記と同じ装置および同じ触媒を用いた。反応時間を通じて0.84モル/時の水素と、0.7モル/時の1,2,3,3,3-ペンタフルオロプロペンとを連続注入し、再循環ループへの流量は0.970Sm3/時にした(すなわち、再循環率は98容量%)。反応器入口の水素/HFO-1225yeモル比は1.18である。圧力は2バールの絶対圧力である。触媒床入口の温度は63℃で、反応中に得られる最高反応器温度は90℃である。接触時間は1.2秒である。
得られたHFO-1225yeの変換率は100%、HFC-245ebの選択率は79%、HFC-254ebの選択率は20.0%である。
実施例2と同じ条件下で運転したが、反応器入口の水素/HFO-1225yeモル比を5.2にし、触媒床入口の温度を100℃にした。反応中に得られる最高温度は123℃である。
得られたHFO-1225yeの変換率は100%、HFC-245ebの選択率は89.6%、HFC-254ebの選択率は10.2%である。
Claims (9)
- 下記(i)〜(iii)を特徴とする1,1,1,2,3-ペンタフルオロプロパンの製造方法:
(i)1,2,3,3,3-ペンタフルオロプロペンを、反応器中で水素化触媒の存在下に、80〜250℃、好ましくは110〜160℃の温度で、超化学量論量で、水素と気相で反応させ、
(ii)1,1,1,2,3-ペンタフルオロプロパンと、未反応水素と、場合によって生じる未反応1,2,3,3,3-ペンタフルオロプロペン、1,1,1,2-テトラフルオロプロパンおよびフッ化水素酸とを含む、反応器からのガス状排出物の一部を再循環し、
(iii)反応器からのガス状排出物の残りの部分から、必要に応じて精製段階を実施した後に、1,1,1,2,3-ペンタフルオロプロパンを回収する。 - 再循環されるガス状排出物の部分が反応器出口の全流出物の少なくとも80容量%、好ましくは93〜98容量%を占める請求項1に記載の方法。
- 反応器出口のガス状排出物が、5〜96容量%の1,1,1,2,3-ペンタフルオロプロパンと、2〜90容量%の水素と、1〜20容量%の1,1,1,2-テトラフルオロプロパンと、0〜10容量%の1,2,3,3,3-ペンタフルオロプロペンとを含む請求項1または2に記載の方法。
- 触媒が必要に応じて担持されたパラジウムを含む請求項1〜3のいずれか一項に記載の方法。
- 担体がアルミナをベースにした担体である請求項4に記載の方法。
- 上記モル比を1.5〜40、好ましくは3〜10にする請求項1〜5のいずれか一項に記載の方法。
- 接触時間を0.2〜20秒、好ましくは1〜5秒にする請求項1〜6のいずれか一項に記載の方法。
- 水素化反応を0.5〜20バールの絶対圧力、好ましくは1〜5バールの絶対圧力で行う請求項1〜7のいずれか一項に記載の方法。
- 連続的に行う請求項1〜8のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0953937A FR2946644B1 (fr) | 2009-06-12 | 2009-06-12 | Procede de fabrication du pentafluoropropane. |
FR0953937 | 2009-06-12 | ||
PCT/FR2010/050866 WO2010142878A1 (fr) | 2009-06-12 | 2010-05-06 | Procede fabrication du pentafluoropropane |
Publications (2)
Publication Number | Publication Date |
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JP2012529481A true JP2012529481A (ja) | 2012-11-22 |
JP5693571B2 JP5693571B2 (ja) | 2015-04-01 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2012514512A Active JP5693571B2 (ja) | 2009-06-12 | 2010-05-06 | ペンタフルオロプロパンの製造方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8946493B2 (ja) |
EP (2) | EP3072871B1 (ja) |
JP (1) | JP5693571B2 (ja) |
CN (1) | CN101921169B (ja) |
ES (1) | ES2584954T3 (ja) |
FR (1) | FR2946644B1 (ja) |
PL (1) | PL2440510T3 (ja) |
WO (1) | WO2010142878A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10221113B2 (en) | 2011-05-16 | 2019-03-05 | The Chemours Company Fc, Llc | Catalytic hydrogenation of fluoroolefins, alpha-alumina supported palladium compositions and their use as hydrogenation catalysts |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110028770A1 (en) * | 2009-08-03 | 2011-02-03 | Honeywell International Inc. | Hydrogenation catalyst |
US8513474B2 (en) | 2010-06-24 | 2013-08-20 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
GB201112370D0 (en) * | 2011-07-19 | 2011-08-31 | Mexichem Amanco Holding Sa | Process |
US9290424B2 (en) | 2013-03-14 | 2016-03-22 | Honeywell International Inc. | Processes for the hydrogenation of halogenated alkenes and the manufacture of fluorinated olefins |
FR3067617B1 (fr) * | 2017-06-20 | 2019-07-19 | Arkema France | Catalyseur a base d'alumine alpha et procede d'hydrogenation d'une olefine en presence de celui-ci. |
CN107698421A (zh) * | 2017-09-06 | 2018-02-16 | 巨化集团技术中心 | 一种制备1,1,1,2,3‑五氟丙烷的方法 |
US11746245B2 (en) | 2018-02-02 | 2023-09-05 | The Boeing Company | Soluble corrosion resistant sol-gel |
FR3093721A1 (fr) | 2019-03-12 | 2020-09-18 | Arkema France | Procédé de production de fluorooléfines |
Citations (6)
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WO1993025510A1 (en) * | 1992-06-05 | 1993-12-23 | Daikin Industries, Ltd. | Processes for producing 1,1,1,2,3-pentafluoropropene and producing 1,1,1,2,3-pentafluoropropane |
WO2008030440A2 (en) * | 2006-09-05 | 2008-03-13 | E. I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
JP2008110980A (ja) * | 2006-10-27 | 2008-05-15 | Honeywell Internatl Inc | ハロゲン化アルカンの選択的脱ハロゲン化水素のための方法 |
JP2008162999A (ja) * | 2006-10-27 | 2008-07-17 | Honeywell Internatl Inc | フッ素化アルカンの製造方法 |
WO2009064939A2 (en) * | 2007-11-16 | 2009-05-22 | Honeywell International Inc. | Manufacture of 1,1,1,2,3,3-hexafluoropropane and 1,1,1,2-tetrafluoropropane via catalytic hydrogenation |
WO2009138764A1 (en) * | 2008-05-15 | 2009-11-19 | Ineos Fluor Holdings Limited | Process for the preparation of 2, 3, 3, 3-trifluoropropene |
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2009
- 2009-06-12 FR FR0953937A patent/FR2946644B1/fr active Active
-
2010
- 2010-05-06 EP EP16166229.1A patent/EP3072871B1/fr active Active
- 2010-05-06 PL PL10727461.5T patent/PL2440510T3/pl unknown
- 2010-05-06 US US13/377,189 patent/US8946493B2/en active Active
- 2010-05-06 EP EP10727461.5A patent/EP2440510B1/fr active Active
- 2010-05-06 JP JP2012514512A patent/JP5693571B2/ja active Active
- 2010-05-06 ES ES10727461.5T patent/ES2584954T3/es active Active
- 2010-05-06 WO PCT/FR2010/050866 patent/WO2010142878A1/fr active Application Filing
- 2010-06-10 CN CN201010202924.1A patent/CN101921169B/zh active Active
Patent Citations (6)
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WO1993025510A1 (en) * | 1992-06-05 | 1993-12-23 | Daikin Industries, Ltd. | Processes for producing 1,1,1,2,3-pentafluoropropene and producing 1,1,1,2,3-pentafluoropropane |
WO2008030440A2 (en) * | 2006-09-05 | 2008-03-13 | E. I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
JP2008110980A (ja) * | 2006-10-27 | 2008-05-15 | Honeywell Internatl Inc | ハロゲン化アルカンの選択的脱ハロゲン化水素のための方法 |
JP2008162999A (ja) * | 2006-10-27 | 2008-07-17 | Honeywell Internatl Inc | フッ素化アルカンの製造方法 |
WO2009064939A2 (en) * | 2007-11-16 | 2009-05-22 | Honeywell International Inc. | Manufacture of 1,1,1,2,3,3-hexafluoropropane and 1,1,1,2-tetrafluoropropane via catalytic hydrogenation |
WO2009138764A1 (en) * | 2008-05-15 | 2009-11-19 | Ineos Fluor Holdings Limited | Process for the preparation of 2, 3, 3, 3-trifluoropropene |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10221113B2 (en) | 2011-05-16 | 2019-03-05 | The Chemours Company Fc, Llc | Catalytic hydrogenation of fluoroolefins, alpha-alumina supported palladium compositions and their use as hydrogenation catalysts |
US10633311B2 (en) | 2011-05-16 | 2020-04-28 | The Chemours Company Fc, Llc | Catalytic hydrogenation of fluoroolefins, alhpa-alumina supported palladium compositions and their use as hydrogenation catalysts |
US11124469B2 (en) | 2011-05-16 | 2021-09-21 | The Chemours Company Fc, Llc | Catalytic hydrogenation of fluoroolefins, alpha-alumina supported palladium compositions and their use as hydrogenation catalysts |
US11702378B2 (en) | 2011-05-16 | 2023-07-18 | The Chemours Company Fc, Llc | Catalytic hydrogenation of fluoroolefins, alpha-alumina supported palladium compositions and their use as hydrogenation catalysts |
Also Published As
Publication number | Publication date |
---|---|
FR2946644B1 (fr) | 2011-10-14 |
EP3072871A1 (fr) | 2016-09-28 |
US8946493B2 (en) | 2015-02-03 |
ES2584954T3 (es) | 2016-09-30 |
EP2440510B1 (fr) | 2016-04-27 |
CN101921169A (zh) | 2010-12-22 |
FR2946644A1 (fr) | 2010-12-17 |
US20120101315A1 (en) | 2012-04-26 |
JP5693571B2 (ja) | 2015-04-01 |
EP3072871B1 (fr) | 2019-06-26 |
CN101921169B (zh) | 2016-01-20 |
PL2440510T3 (pl) | 2016-10-31 |
WO2010142878A1 (fr) | 2010-12-16 |
EP2440510A1 (fr) | 2012-04-18 |
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