JP5926296B2 - ヒドロクロロフルオロカーボンの選択的触媒接触脱塩化水素化 - Google Patents
ヒドロクロロフルオロカーボンの選択的触媒接触脱塩化水素化 Download PDFInfo
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- JP5926296B2 JP5926296B2 JP2013555480A JP2013555480A JP5926296B2 JP 5926296 B2 JP5926296 B2 JP 5926296B2 JP 2013555480 A JP2013555480 A JP 2013555480A JP 2013555480 A JP2013555480 A JP 2013555480A JP 5926296 B2 JP5926296 B2 JP 5926296B2
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- carbon
- dehydrochlorination
- ccl
- catalytic
- chclch
- Prior art date
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- 238000007033 dehydrochlorination reaction Methods 0.000 title claims description 25
- 230000003197 catalytic effect Effects 0.000 title description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 230000008901 benefit Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- QJMGASHUZRHZBT-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)CCl QJMGASHUZRHZBT-UHFFFAOYSA-N 0.000 description 4
- 239000003575 carbonaceous material Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 3
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 2
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 238000010306 acid treatment Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- -1 hydro chloro fluoro olefins Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- B01J37/06—Washing
-
- 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
- B01J37/08—Heat treatment
- B01J37/082—Decomposition and pyrolysis
- B01J37/084—Decomposition of carbon-containing compounds into carbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
Description
以下の実施例において本明細書に記載した概念をさらに説明するが、これらは、特許請求の範囲に記載した本発明の範囲を限定するものではない。
Claims (6)
- 脱塩化水素化プロセスであって、
反応域において式RfCHClCH2Clをカーボン触媒と接触させて、式RfCCl=CH2を含む生成混合物を生成させるステップを含み、
式中、Rfは、過フッ化アルキル基、
であり、
前記反応域における温度は、325℃から500℃であり、
式R f CCl=CH 2 に対する生成物選択性は、少なくとも90モル%である、
ことを特徴とするプロセス。 - 前記カーボン触媒は、活性炭であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- 前記カーボン触媒は、酸洗浄した活性炭であることを特徴とする請求項2に記載の脱塩化水素化プロセス。
- 前記カーボン触媒は、非酸洗浄の活性炭であることを特徴とする請求項2に記載の脱塩化水素化プロセス。
- Rfは、CF3であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
- RfCCl=CH2に対する脱塩化水素化選択性は、少なくとも95モル%であることを特徴とする請求項1に記載の脱塩化水素化プロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161444868P | 2011-02-21 | 2011-02-21 | |
US61/444,868 | 2011-02-21 | ||
PCT/US2012/025881 WO2012115934A1 (en) | 2011-02-21 | 2012-02-21 | Selective catalytic dehydrochlorination of hydrochlorofluorocarbons |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014513674A JP2014513674A (ja) | 2014-06-05 |
JP5926296B2 true JP5926296B2 (ja) | 2016-05-25 |
Family
ID=45815964
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013555480A Active JP5926296B2 (ja) | 2011-02-21 | 2012-02-21 | ヒドロクロロフルオロカーボンの選択的触媒接触脱塩化水素化 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8884082B2 (ja) |
EP (1) | EP2678299A1 (ja) |
JP (1) | JP5926296B2 (ja) |
KR (1) | KR101950323B1 (ja) |
CN (2) | CN106957210B (ja) |
MX (1) | MX2013009579A (ja) |
TW (1) | TW201238937A (ja) |
WO (1) | WO2012115934A1 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9724684B2 (en) | 2011-02-21 | 2017-08-08 | The Chemours Company Fc, Llc | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
US9012702B2 (en) | 2011-02-21 | 2015-04-21 | E. I. Du Pont De Nemours And Company | Catalytic dehydrochlorination of hydrochlorofluorocarbons |
JP2018027895A (ja) * | 2015-01-06 | 2018-02-22 | 旭硝子株式会社 | (e)−1−クロロ−3,3,3−トリフルオロプロペンの製造方法 |
KR20180000720A (ko) | 2015-05-21 | 2018-01-03 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | SbF5에 의한 1233xf의 244bb로의 히드로플루오린화 |
EP3347334A4 (en) * | 2015-09-11 | 2019-05-01 | The Chemours Company FC, LLC | DEHYDROHALOGENATION OF HYDROCHLOROFLUOROCARBONES |
WO2020014130A1 (en) | 2018-07-09 | 2020-01-16 | The Chemours Company Fc, Llc | Compositions and methods for an integrated 2,3,3,3-tetrafluoropropene manufacturing process |
WO2020018764A1 (en) | 2018-07-18 | 2020-01-23 | The Chemours Company Fc, Llc | Production of haloolefins in an adiabatic reaction zone |
US11904301B2 (en) | 2018-09-07 | 2024-02-20 | The Chemours Company Fc, Llc | Fluorine removal from antimony fluorohalide catalyst using chlorocarbons |
Family Cites Families (27)
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US2898383A (en) | 1958-08-27 | 1959-08-04 | Columbia Southern Chem Corp | Dehydrochlorination of tetrachloroethane |
US3631207A (en) | 1966-07-14 | 1971-12-28 | Detrex Chem Ind | Tri- and tetrachloroethylene process |
SU1706690A1 (ru) | 1988-04-19 | 1992-01-23 | Всесоюзный Научно-Исследовательский Институт Технического Углерода | Пористый углеродный материал |
US5136113A (en) | 1991-07-23 | 1992-08-04 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenolysis |
US8530708B2 (en) | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
US8084653B2 (en) | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
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 |
EP2377610A3 (en) | 2004-12-22 | 2012-02-08 | E. I. Du Pont De Nemours And Company | Process for increasing the fluorine content by photochemical reactions |
JP2006193437A (ja) * | 2005-01-11 | 2006-07-27 | Central Glass Co Ltd | 1,1,3,3,3−ペンタフルオロプロペンの製造方法 |
US8071825B2 (en) | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
BRPI0717091A2 (pt) * | 2006-10-03 | 2013-11-26 | Ineos Fluor Holdings Ltd | Processos para preparação de um composto e para isomerização de um composto, uso de um catalisador, fluido, mistura refrigerante, e, automóvel. |
GB0806422D0 (en) | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
CN103483141B (zh) * | 2006-10-31 | 2015-09-16 | 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 |
GB0625214D0 (en) * | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
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US7884254B2 (en) * | 2007-08-08 | 2011-02-08 | Honeywell International Inc. | Dehydrochlorination of hydrochlorofluorocarbons using pre-treated activated carbon catalysts |
KR101656109B1 (ko) * | 2008-05-07 | 2016-09-08 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 2,3-다이클로로-1,1,1-트라이플루오로프로판, 2-클로로-1,1,1-트라이플루오로프로펜, 2-클로로-1,1,1,2-테트라플루오로프로판 또는 2,3,3,3-테트라플루오로프로펜을 포함하는 조성물 |
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WO2011077192A1 (en) * | 2009-12-23 | 2011-06-30 | Arkema France | CATALYTIC GAS PHASE FLUORINATION OF 1233xf TO 1234yf |
US9012702B2 (en) | 2011-02-21 | 2015-04-21 | E. I. Du Pont De Nemours And Company | Catalytic dehydrochlorination of hydrochlorofluorocarbons |
US9724684B2 (en) | 2011-02-21 | 2017-08-08 | The Chemours Company Fc, Llc | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
-
2012
- 2012-02-16 US US13/397,967 patent/US8884082B2/en active Active
- 2012-02-17 TW TW101105220A patent/TW201238937A/zh unknown
- 2012-02-21 JP JP2013555480A patent/JP5926296B2/ja active Active
- 2012-02-21 CN CN201710167541.7A patent/CN106957210B/zh active Active
- 2012-02-21 MX MX2013009579A patent/MX2013009579A/es active IP Right Grant
- 2012-02-21 EP EP12708434.1A patent/EP2678299A1/en not_active Withdrawn
- 2012-02-21 WO PCT/US2012/025881 patent/WO2012115934A1/en active Application Filing
- 2012-02-21 CN CN2012800098297A patent/CN103370293A/zh active Pending
- 2012-02-21 KR KR1020137024270A patent/KR101950323B1/ko active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
MX2013009579A (es) | 2013-09-06 |
JP2014513674A (ja) | 2014-06-05 |
WO2012115934A1 (en) | 2012-08-30 |
US20120215036A1 (en) | 2012-08-23 |
US8884082B2 (en) | 2014-11-11 |
CN106957210A (zh) | 2017-07-18 |
KR20140004753A (ko) | 2014-01-13 |
US20140012048A9 (en) | 2014-01-09 |
CN103370293A (zh) | 2013-10-23 |
CN106957210B (zh) | 2019-07-16 |
EP2678299A1 (en) | 2014-01-01 |
KR101950323B1 (ko) | 2019-02-20 |
TW201238937A (en) | 2012-10-01 |
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