KR101386906B1 - HFC-245fa로 부터 HFO 트랜스-1234ze를 제조하는방법 - Google Patents
HFC-245fa로 부터 HFO 트랜스-1234ze를 제조하는방법 Download PDFInfo
- Publication number
- KR101386906B1 KR101386906B1 KR1020070085689A KR20070085689A KR101386906B1 KR 101386906 B1 KR101386906 B1 KR 101386906B1 KR 1020070085689 A KR1020070085689 A KR 1020070085689A KR 20070085689 A KR20070085689 A KR 20070085689A KR 101386906 B1 KR101386906 B1 KR 101386906B1
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- South Korea
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- tetrafluoropropene
- catalyst
- trans
- hfc
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- 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
-
- 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
- C07C17/25—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
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- 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
- Y02P20/10—Process efficiency
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)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83987306P | 2006-08-24 | 2006-08-24 | |
| US60/839,873 | 2006-08-24 | ||
| US11/775,318 | 2007-07-10 | ||
| US11/775,318 US8067650B2 (en) | 2006-08-24 | 2007-07-10 | Process for the production of HFO trans-1234ze from HFC-245fa |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20080018851A KR20080018851A (ko) | 2008-02-28 |
| KR101386906B1 true KR101386906B1 (ko) | 2014-04-18 |
Family
ID=39133586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020070085689A Active KR101386906B1 (ko) | 2006-08-24 | 2007-08-24 | HFC-245fa로 부터 HFO 트랜스-1234ze를 제조하는방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8067650B2 (enExample) |
| EP (3) | EP4046983A1 (enExample) |
| JP (5) | JP2008150356A (enExample) |
| KR (1) | KR101386906B1 (enExample) |
| CN (1) | CN101265155B (enExample) |
| CA (1) | CA2598386C (enExample) |
| DE (1) | DE07253347T1 (enExample) |
| ES (1) | ES2910712T3 (enExample) |
| MX (1) | MX2007010287A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230031414A (ko) * | 2021-08-27 | 2023-03-07 | (주)후성 | 하이드로플루오로올레핀의 제조 시 HFO-1234ze(E)의 생산량을 증가시키는 방법 |
Families Citing this family (53)
| 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 |
| US8067650B2 (en) * | 2006-08-24 | 2011-11-29 | Honeywell International Inc. | Process for the production of HFO trans-1234ze from HFC-245fa |
| 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 |
| GB0706978D0 (en) | 2007-04-11 | 2007-05-16 | Ineos Fluor Holdings Ltd | Process |
| GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
| US8445736B2 (en) * | 2008-06-26 | 2013-05-21 | Arkema Inc. | Catalytic gas phase fluorination of 1230xa to 1234yf |
| US20100016457A1 (en) * | 2008-07-16 | 2010-01-21 | Bowman James M | Hfo-1234ze mixed isomers with hfc-245fa as a blowing agent, aerosol, and solvent |
| JP5304887B2 (ja) * | 2008-08-06 | 2013-10-02 | ダイキン工業株式会社 | 2,3,3,3−テトラフルオロプロペンと1,3,3,3−テトラフルオロプロペンの製造方法 |
| JP5277813B2 (ja) * | 2008-09-11 | 2013-08-28 | セントラル硝子株式会社 | フッ素化プロペンの製造方法 |
| US9926244B2 (en) | 2008-10-28 | 2018-03-27 | Honeywell International Inc. | Process for drying HCFO-1233zd |
| US9540296B2 (en) | 2015-03-19 | 2017-01-10 | Honeywell International Inc. | Process for drying HCFO-1233zd |
| WO2010059496A1 (en) * | 2008-11-19 | 2010-05-27 | Arkema Inc. | Process for the manufacture of hydrochlorofluoroolefins |
| US8987534B2 (en) | 2008-11-19 | 2015-03-24 | Arkema Inc. | Process for the manufacture of hydrochlorofluoroolefins |
| US8987535B2 (en) | 2008-11-19 | 2015-03-24 | Arkema Inc. | Process for the manufacture of hydrochlorofluoroolefins |
| US8217208B2 (en) | 2008-12-12 | 2012-07-10 | Honeywell International, Inc. | Isomerization of 1-chloro-3,3,3-trifluoropropene |
| US8288598B2 (en) * | 2009-01-16 | 2012-10-16 | Honeywell International Inc. | Isomerization of 1,1,3,3-tetrafluoropropene |
| WO2010101198A1 (en) | 2009-03-04 | 2010-09-10 | Daikin Industries, Ltd. | Process for preparing fluorine-containing propenes containing 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene |
| US8747691B2 (en) | 2010-05-06 | 2014-06-10 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and water |
| US8951431B2 (en) * | 2010-05-06 | 2015-02-10 | E I Du Pont De Nemours And Company | Azeotrope-like compositions of pentafluoropropene and water |
| US8518293B2 (en) * | 2010-09-03 | 2013-08-27 | Honeywell International Inc. | 1,3,3,3-tetrafluoropropene process azeotropes with HF |
| IT1406472B1 (it) | 2010-12-22 | 2014-02-28 | Nuovo Pignone Spa | Prova per similitudine di prestazione di compressore |
| US8436217B2 (en) | 2011-04-25 | 2013-05-07 | Honeywell International Inc. | Integrated process to co-produce 1,1,1,3,3-pentafluoropropane, trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene |
| GB2492847A (en) * | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| US8921621B2 (en) * | 2012-02-15 | 2014-12-30 | Honeywell International Inc. | Process for the production of HCFC-1233zd |
| US9938212B2 (en) * | 2012-03-28 | 2018-04-10 | Honeywell International Inc. | Integrated process to coproduce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane |
| US8664456B2 (en) * | 2012-03-28 | 2014-03-04 | Honeywell International Inc. | Integrated process for the co-production of trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane |
| US20130283832A1 (en) * | 2012-04-30 | 2013-10-31 | Trane International Inc. | Refrigeration system with purge using enrivonmentally-suitable chiller refrigerant |
| GB201207666D0 (en) | 2012-05-02 | 2012-06-13 | Mexichem Amanco Holding Sa | Process |
| CN103880590B (zh) * | 2012-12-19 | 2016-10-05 | 中化蓝天集团有限公司 | 一种制备1,3,3,3-四氟丙烯的工艺 |
| US9272968B2 (en) | 2013-03-14 | 2016-03-01 | Honeywell International Inc. | Process to suppress the formation of 3,3,3-trifluoropropyne in fluorocarbon manufacture |
| US9162947B2 (en) | 2013-03-15 | 2015-10-20 | Honeywell International Inc. | High temperature isomerization of (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene |
| KR20250150693A (ko) | 2013-03-15 | 2025-10-20 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜 생성물에서 할로겐화 에틸렌 불순물을 제거하는 방법 |
| US9187386B2 (en) * | 2013-05-23 | 2015-11-17 | The Chemours Company Fc, Llc | Catalytic process of making 1,3,3,3-tetrafluoropropene |
| US9302962B2 (en) * | 2014-08-14 | 2016-04-05 | The Chemours Company Fc, Llc | Dehydrofluorination of 245fa to 1234ze |
| 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 |
| CN105111038B (zh) * | 2015-08-18 | 2017-11-21 | 巨化集团技术中心 | 一种用甲基氯化镁制备2,3,3,3‑四氟丙烯的方法 |
| EP3353138B1 (en) * | 2015-09-21 | 2024-07-03 | Arkema, Inc. | Process for making tetrachloropropene by catalyzed gas-phase dehydrochlorination of pentachloropropane |
| 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 |
| CN106866353B (zh) * | 2016-12-28 | 2019-06-18 | 陕西延长石油集团氟硅化工有限公司 | 一种合成反式-1,3,3,3-四氟丙烯的方法 |
| CN106831316B (zh) * | 2016-12-28 | 2019-11-15 | 陕西延长石油集团氟硅化工有限公司 | 一种生产反式-1,3,3,3-四氟丙烯的方法 |
| CN106883095B (zh) * | 2016-12-28 | 2020-02-18 | 西安近代化学研究所 | 一种生产反式-1,3,3,3-四氟丙烯的工艺 |
| MY202072A (en) | 2018-10-26 | 2024-04-02 | Chemours Co Fc Llc | Hfo-1234ze and hfo-1234yf compositions and processes for producing and using the compositions |
| US11209196B2 (en) | 2018-10-26 | 2021-12-28 | The Chemours Company Fc, Llc | HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions |
| BR112021022059A2 (pt) | 2018-10-26 | 2021-12-28 | Chemours Co Fc Llc | Composições de fluoropropeno, métodos de produção de uma mistura e de resfriamento, processos para transferência de calor, para tratamento de uma superfície e para formação de uma composição, sistema de refrigeração, aparelhos de refrigeração, uso da composição de fluoropropeno e método para substituição de um refrigerante |
| MX2021005780A (es) * | 2018-11-15 | 2021-07-02 | Arkema Inc | Metodo para neutralizar y eliminar hf de una corriente de crudo que contiene hidroclorofluoroolefina. |
| GB2580623A (en) | 2019-01-17 | 2020-07-29 | Mexichem Fluor Sa De Cv | Method |
| JP6933239B2 (ja) * | 2019-02-21 | 2021-09-08 | ダイキン工業株式会社 | ハロゲン化アルケン化合物及びフッ化アルキン化合物の製造方法 |
| JP7353013B2 (ja) * | 2019-08-29 | 2023-09-29 | フジアン ヨンジン テクノロジー カンパニー リミテッド | フルオロベンゼンおよびその触媒の製造プロセス |
| CN115722255B (zh) * | 2022-10-13 | 2024-08-27 | 浙江衢化氟化学有限公司 | 一种用于生产1,1,1,2,3-五氯丙烷的负载型催化剂及其制备方法和应用 |
| CN115322071B (zh) * | 2022-10-17 | 2023-01-31 | 山东东岳化工有限公司 | 以1,1,1,2,3-五氟丙烷为原料联产制备三氟丙烯和四氟丙烯的方法 |
| TW202535813A (zh) | 2023-10-30 | 2025-09-16 | 美商科慕Fc有限責任公司 | 包含1,3,3,3-四氟丙烯的組成物、其製備方法、及其用途 |
| TW202528277A (zh) | 2023-10-30 | 2025-07-16 | 美商科慕Fc有限責任公司 | 包含1,3,3,3-四氟丙烯的組成物、其製造方法、及其用途 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11140002A (ja) * | 1997-11-11 | 1999-05-25 | Central Glass Co Ltd | 1,3,3,3−テトラフルオロプロペンの製造法 |
| US6124510A (en) * | 1998-07-21 | 2000-09-26 | Elf Atochem North America, Inc. | 1234ze preparation |
| US20050090698A1 (en) * | 2003-10-27 | 2005-04-28 | Honeywell International, Inc. | Process for producing fluoropropenes |
| EP2014637A1 (en) * | 2006-08-24 | 2009-01-14 | Honeywell International Inc. | Process for the production of HFO trans-1234ZE from HFC-245FA |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA675318A (en) | 1963-12-03 | W. Clark Jared | Fluorination of hexachlorobutadiene | |
| US2892000A (en) | 1957-02-15 | 1959-06-23 | Du Pont | Manufacture of vinyl fluoride and 1, 1-difluoroethane |
| GB921254A (en) | 1960-06-10 | 1963-03-20 | Union Carbide Corp | Improvements in and relating to fluorination |
| NL298215A (enExample) | 1962-09-26 | 1900-01-01 | ||
| US3398204A (en) * | 1965-08-26 | 1968-08-20 | Dow Chemical Co | Isomerization process |
| JPS58185588A (ja) | 1982-04-23 | 1983-10-29 | Shionogi & Co Ltd | 空気酸化によるハロメチル化合物の酸化方法および酸化生成物 |
| US5268122A (en) * | 1991-08-28 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes for their production, and use of gem-dihydropolyfluoroalkanes in cleaning compositions |
| BR9306493A (pt) | 1992-06-05 | 1998-09-15 | Daikin Ind Ltd | Método para a manufatura de 1,1,1,2,3-pentafluoropropeno e método para a manufatura de 1,1,1,2,3-pentafluoropropano |
| 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 |
| IT1282961B1 (it) | 1996-05-06 | 1998-04-02 | Ausimont Spa | Processo per la rigenerazione di un catalizzatore a base di composti di cromo trivalente |
| JPH1017502A (ja) * | 1996-07-01 | 1998-01-20 | Central Glass Co Ltd | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
| US5895639A (en) | 1996-07-03 | 1999-04-20 | Alliedsignal Inc. | Separation of hydrogen fluoride from a fluorocarbon/hydrogen fluoride azeotropic mixture by sulfuric acid |
| US5763706A (en) | 1996-07-03 | 1998-06-09 | Alliedsignal Inc. | Process for the manufacture of 1,1,1,3,3-pentafluoropropane and 1,1,1,3,3,3-hexafluoropropane |
| US5710352A (en) | 1996-09-19 | 1998-01-20 | Alliedsignal Inc. | Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene |
| US5945573A (en) | 1997-01-31 | 1999-08-31 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,3,3-pentafluoropropane |
| JP4031052B2 (ja) * | 1997-01-31 | 2008-01-09 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ペンタフルオロプロペンの接触製造 |
| US5986151A (en) * | 1997-02-05 | 1999-11-16 | Alliedsignal Inc. | Fluorinated propenes from pentafluoropropane |
| US5895825A (en) * | 1997-12-01 | 1999-04-20 | Elf Atochem North America, Inc. | Preparation of 1,1,1,3,3-pentafluoropropane |
| DE69909860T2 (de) | 1998-02-26 | 2004-05-27 | Central Glass Co., Ltd., Ube | Verfahren zur Herstellung von fluorierten Propanen |
| JP3031465B2 (ja) * | 1998-02-26 | 2000-04-10 | セントラル硝子株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
| JP3518321B2 (ja) | 1998-03-23 | 2004-04-12 | ダイキン工業株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
| US6548719B1 (en) * | 2001-09-25 | 2003-04-15 | Honeywell International | Process for producing fluoroolefins |
| US7592494B2 (en) * | 2003-07-25 | 2009-09-22 | Honeywell International Inc. | Process for the manufacture of 1,3,3,3-tetrafluoropropene |
| KR20070011554A (ko) * | 2004-04-29 | 2007-01-24 | 허니웰 인터내셔널 인코포레이티드 | 1,3,3,3-테트라플루오로프로펜의 합성 방법 |
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| 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 |
| US7485760B2 (en) | 2006-08-24 | 2009-02-03 | Honeywell International Inc. | Integrated HFC trans-1234ze manufacture process |
-
2007
- 2007-07-10 US US11/775,318 patent/US8067650B2/en active Active
- 2007-08-23 CN CN2007101857572A patent/CN101265155B/zh active Active
- 2007-08-23 CA CA2598386A patent/CA2598386C/en active Active
- 2007-08-23 MX MX2007010287A patent/MX2007010287A/es active IP Right Grant
- 2007-08-24 JP JP2007218239A patent/JP2008150356A/ja not_active Withdrawn
- 2007-08-24 KR KR1020070085689A patent/KR101386906B1/ko active Active
- 2007-08-24 DE DE07253347T patent/DE07253347T1/de active Pending
- 2007-08-24 EP EP21217051.8A patent/EP4046983A1/en active Pending
- 2007-08-24 ES ES17152564T patent/ES2910712T3/es active Active
- 2007-08-24 EP EP17152564.5A patent/EP3176147B1/en active Active
- 2007-08-24 EP EP07253347A patent/EP2014637A1/en not_active Withdrawn
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2014
- 2014-01-28 JP JP2014013192A patent/JP6294087B2/ja active Active
-
2016
- 2016-11-17 JP JP2016223894A patent/JP2017061524A/ja not_active Withdrawn
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2018
- 2018-03-26 JP JP2018058161A patent/JP6574284B2/ja active Active
-
2019
- 2019-08-15 JP JP2019149017A patent/JP2019214596A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11140002A (ja) * | 1997-11-11 | 1999-05-25 | Central Glass Co Ltd | 1,3,3,3−テトラフルオロプロペンの製造法 |
| US6124510A (en) * | 1998-07-21 | 2000-09-26 | Elf Atochem North America, Inc. | 1234ze preparation |
| US20050090698A1 (en) * | 2003-10-27 | 2005-04-28 | Honeywell International, Inc. | Process for producing fluoropropenes |
| EP2014637A1 (en) * | 2006-08-24 | 2009-01-14 | Honeywell International Inc. | Process for the production of HFO trans-1234ZE from HFC-245FA |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230031414A (ko) * | 2021-08-27 | 2023-03-07 | (주)후성 | 하이드로플루오로올레핀의 제조 시 HFO-1234ze(E)의 생산량을 증가시키는 방법 |
| KR102630195B1 (ko) * | 2021-08-27 | 2024-01-29 | (주)후성 | 하이드로플루오로올레핀의 제조 시 HFO-1234ze(E)의 생산량을 증가시키는 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101265155A (zh) | 2008-09-17 |
| JP2008150356A (ja) | 2008-07-03 |
| EP3176147B1 (en) | 2022-03-09 |
| US20080051611A1 (en) | 2008-02-28 |
| CA2598386A1 (en) | 2008-02-24 |
| ES2910712T3 (es) | 2022-05-13 |
| CA2598386C (en) | 2014-08-12 |
| EP2014637A1 (en) | 2009-01-14 |
| US8067650B2 (en) | 2011-11-29 |
| JP2017061524A (ja) | 2017-03-30 |
| JP6294087B2 (ja) | 2018-03-14 |
| JP6574284B2 (ja) | 2019-09-11 |
| JP2019214596A (ja) | 2019-12-19 |
| JP2014098007A (ja) | 2014-05-29 |
| DE07253347T1 (de) | 2009-06-04 |
| JP2018115195A (ja) | 2018-07-26 |
| KR20080018851A (ko) | 2008-02-28 |
| MX2007010287A (es) | 2008-10-28 |
| EP4046983A1 (en) | 2022-08-24 |
| EP3176147A1 (en) | 2017-06-07 |
| CN101265155B (zh) | 2013-08-21 |
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