KR20090048378A - 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 - Google Patents
2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 Download PDFInfo
- Publication number
- KR20090048378A KR20090048378A KR1020080111026A KR20080111026A KR20090048378A KR 20090048378 A KR20090048378 A KR 20090048378A KR 1020080111026 A KR1020080111026 A KR 1020080111026A KR 20080111026 A KR20080111026 A KR 20080111026A KR 20090048378 A KR20090048378 A KR 20090048378A
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- propene
- contacting
- intermediate composition
- reactor
- 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.)
- Ceased
Links
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 24
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 titanium halides Chemical class 0.000 claims abstract description 11
- 239000007858 starting material Substances 0.000 claims abstract description 9
- 239000012467 final product Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000010936 titanium Substances 0.000 claims abstract description 4
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 32
- 239000007789 gas Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052787 antimony Inorganic materials 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 claims 1
- 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 8
- 239000000047 product Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- CAQPTDOAJUMIAI-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)C(F)(F)F CAQPTDOAJUMIAI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000007233 catalytic pyrolysis Methods 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000000178 monomer 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
- 229920000642 polymer Polymers 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010891 toxic waste Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98659907P | 2007-11-09 | 2007-11-09 | |
| US60/986,599 | 2007-11-09 | ||
| US12/265,335 | 2008-11-05 | ||
| US12/265,335 US8324436B2 (en) | 2006-01-03 | 2008-11-05 | Gas phase synthesis of 2,3,3,3-tetrafluoro-1-propene from 2-chloro-3,3,3-trifluoro-1-propene |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020150145173A Division KR20150122110A (ko) | 2007-11-09 | 2015-10-19 | 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090048378A true KR20090048378A (ko) | 2009-05-13 |
Family
ID=40624390
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020080111026A Ceased KR20090048378A (ko) | 2007-11-09 | 2008-11-10 | 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 |
| KR1020150145173A Ceased KR20150122110A (ko) | 2007-11-09 | 2015-10-19 | 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 |
| KR1020160175475A Ceased KR20170000378A (ko) | 2007-11-09 | 2016-12-21 | 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020150145173A Ceased KR20150122110A (ko) | 2007-11-09 | 2015-10-19 | 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 |
| KR1020160175475A Ceased KR20170000378A (ko) | 2007-11-09 | 2016-12-21 | 2-클로로-3,3,3-트리플루오로-1-프로펜으로부터 2,3,3,3-테트라플루오로-1-프로펜의 가스상 합성 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8324436B2 (https=) |
| JP (1) | JP5462469B2 (https=) |
| KR (3) | KR20090048378A (https=) |
| CN (1) | CN101440017B (https=) |
| AT (1) | ATE551314T1 (https=) |
| ES (1) | ES2381885T3 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9024092B2 (en) * | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US20230150900A1 (en) * | 2004-04-29 | 2023-05-18 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US20090182179A1 (en) * | 2008-01-15 | 2009-07-16 | Honeywell International Inc. | Hydrofluorination of 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane with catalysts of sbcl3, sbcl5, sbf5, ticl4, sncl4, cr2o3 and fluorinated cr2o3 |
| US8952208B2 (en) * | 2006-01-03 | 2015-02-10 | Honeywell International Inc. | Method for prolonging a catalyst's life during hydrofluorination |
| US9493384B2 (en) | 2007-07-06 | 2016-11-15 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US9035111B2 (en) * | 2007-08-22 | 2015-05-19 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| CN104164214B (zh) * | 2008-05-07 | 2018-04-24 | 科慕埃弗西有限公司 | 可用作热传递组合物的组合物 |
| US8916733B2 (en) * | 2008-06-17 | 2014-12-23 | Honeywell International Inc. | Processes for hydrofluorination of 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane |
| FR2935700B1 (fr) * | 2008-09-11 | 2013-05-10 | Arkema France | Procede de preparation de composes trifluores et tetrafluores |
| JP5581858B2 (ja) | 2009-07-21 | 2014-09-03 | セントラル硝子株式会社 | ２−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
| CN102686542A (zh) * | 2009-12-23 | 2012-09-19 | 阿克马法国公司 | 1233xf到1234yf的催化气相氟化 |
| US8426656B2 (en) | 2010-04-05 | 2013-04-23 | Honeywell International Inc. | Integrated process to co-produce trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene |
| US8927791B2 (en) * | 2010-04-29 | 2015-01-06 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
| US8436218B2 (en) | 2010-05-27 | 2013-05-07 | Honeywell International Inc. | Azeotrope-like composition of hexafluoropropane, hexafluoropropene and hydrogen fluoride |
| CN102199071B (zh) * | 2011-04-08 | 2013-05-01 | 北京宇极科技发展有限公司 | 一种2,3,3,3-四氟丙烯的合成方法 |
| JP6271431B2 (ja) * | 2011-09-30 | 2018-01-31 | 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． | ２，３，３，３−テトラフルオロプロペンの製造方法 |
| CN103946196B (zh) * | 2011-09-30 | 2016-12-14 | 霍尼韦尔国际公司 | 制造2,3,3,3-四氟丙烯的方法 |
| WO2013119919A1 (en) | 2012-02-10 | 2013-08-15 | Haiyou Wang | Improved process for the manufacture of 2,3,3,3-tetrafluoropropene |
| JP6043415B2 (ja) * | 2015-08-20 | 2016-12-14 | アルケマ フランス | ２，３，３，３−テトラフルオロプロペンの製造方法 |
| US10005705B2 (en) | 2015-11-12 | 2018-06-26 | Honeywell International Inc. | Process for the production of fluorinated cyclobutane |
| US9790151B2 (en) | 2015-11-12 | 2017-10-17 | Honeywell International Inc. | Process for making 2,3,3,3-tetrafluoropropene and/or vinylidine fluoride |
| US9856193B2 (en) | 2015-11-12 | 2018-01-02 | Honeywell International Inc. | Process for the production of fluorinated cyclobutane |
| BR112019009013A2 (pt) | 2016-11-08 | 2019-07-16 | Honeywell Int Inc | processo para a produção de ciclobutano fluorado |
| CN112313199A (zh) | 2018-06-06 | 2021-02-02 | 霍尼韦尔国际公司 | 用于HCFC-244bb的脱氯化氢以制备HFO-1234yf的方法 |
| CN112739673B (zh) | 2018-08-24 | 2025-03-25 | 霍尼韦尔国际公司 | 用于产生三氟碘甲烷和三氟乙酰碘的方法 |
| CN113242876A (zh) | 2018-12-21 | 2021-08-10 | 霍尼韦尔国际公司 | 包含1,2,2-三氟-1-三氟甲基环丁烷的发泡剂组合物及发泡方法 |
| US11554956B2 (en) | 2019-04-16 | 2023-01-17 | Honeywell International Inc. | Integrated process and catalysts for manufacturing hydrogen iodide from hydrogen and iodine |
| MX2022011805A (es) | 2020-03-24 | 2023-01-11 | Generation Bio Co | Vectores de adn no virales y usos de estos para expresar agentes terapéuticos con factor ix. |
| AU2021244559A1 (en) | 2020-03-24 | 2022-11-17 | Generation Bio Co. | Non-viral DNA vectors and uses thereof for expressing Gaucher therapeutics |
| WO2024040222A1 (en) | 2022-08-19 | 2024-02-22 | Generation Bio Co. | Cleavable closed-ended dna (cedna) and methods of use thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931840A (en) | 1958-11-25 | 1960-04-05 | Du Pont | Process for preparing 2, 3, 3, 3-tetrafluoropropene |
| JPH01207250A (ja) | 1988-02-12 | 1989-08-21 | Daikin Ind Ltd | 含フツ素オレフインの製造方法 |
| JP2755530B2 (ja) | 1992-08-28 | 1998-05-20 | 株式会社トクヤマ | 含フッ素アルコールの製造方法 |
| CA2564991C (en) * | 2004-04-29 | 2013-03-19 | Honeywell International Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene |
| US8084653B2 (en) * | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US9024092B2 (en) * | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8664455B2 (en) * | 2008-08-08 | 2014-03-04 | Honeywell International Inc. | Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) |
| SI3336074T1 (sl) | 2006-01-03 | 2025-09-30 | Honeywell International Inc. | Postopek za proizvodnjo fluoriranih organskih spojin |
-
2008
- 2008-11-05 US US12/265,335 patent/US8324436B2/en active Active
- 2008-11-10 AT AT08168778T patent/ATE551314T1/de active
- 2008-11-10 CN CN2008101779703A patent/CN101440017B/zh active Active
- 2008-11-10 ES ES08168778T patent/ES2381885T3/es active Active
- 2008-11-10 KR KR1020080111026A patent/KR20090048378A/ko not_active Ceased
- 2008-11-10 JP JP2008287911A patent/JP5462469B2/ja active Active
-
2015
- 2015-10-19 KR KR1020150145173A patent/KR20150122110A/ko not_active Ceased
-
2016
- 2016-12-21 KR KR1020160175475A patent/KR20170000378A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US8324436B2 (en) | 2012-12-04 |
| US20120203036A9 (en) | 2012-08-09 |
| US20090124837A1 (en) | 2009-05-14 |
| ATE551314T1 (de) | 2012-04-15 |
| ES2381885T3 (es) | 2012-06-01 |
| KR20150122110A (ko) | 2015-10-30 |
| JP5462469B2 (ja) | 2014-04-02 |
| CN101440017A (zh) | 2009-05-27 |
| CN101440017B (zh) | 2013-11-20 |
| KR20170000378A (ko) | 2017-01-02 |
| JP2009137945A (ja) | 2009-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 20081110 |
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