KR20190086789A - 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 - Google Patents
하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 Download PDFInfo
- Publication number
- KR20190086789A KR20190086789A KR1020197020662A KR20197020662A KR20190086789A KR 20190086789 A KR20190086789 A KR 20190086789A KR 1020197020662 A KR1020197020662 A KR 1020197020662A KR 20197020662 A KR20197020662 A KR 20197020662A KR 20190086789 A KR20190086789 A KR 20190086789A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrochlorofluoropropane
- fluoropropene
- temperature
- conversion
- chloropropane
- 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
- 238000006243 chemical reaction Methods 0.000 title abstract description 28
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 claims abstract description 19
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 12
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims description 8
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 9
- 238000000197 pyrolysis Methods 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 abstract 1
- 230000008901 benefit Effects 0.000 description 7
- 238000007033 dehydrochlorination reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910001026 inconel Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 3
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 239000006200 vaporizer Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- LLJWABOOFANACB-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)CC(F)(F)Cl LLJWABOOFANACB-UHFFFAOYSA-N 0.000 description 2
- LDMYCECIGXPKDO-UHFFFAOYSA-N 2-chloro-1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)(Cl)C(F)(F)F LDMYCECIGXPKDO-UHFFFAOYSA-N 0.000 description 2
- JYNCTFQDWJMJDI-UHFFFAOYSA-N 2-chloro-1,1,1,3,3-pentafluoropropane Chemical compound FC(F)C(Cl)C(F)(F)F JYNCTFQDWJMJDI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JSECXTYNFBONSF-UHFFFAOYSA-N 3-chloro-1,1,1,2-tetrafluoropropane Chemical compound ClCC(F)C(F)(F)F JSECXTYNFBONSF-UHFFFAOYSA-N 0.000 description 2
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical compound FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 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 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 description 1
- CNNJBYUJTYGLGG-UHFFFAOYSA-N 2-chloro-1,1,1,3-tetrafluoropropane Chemical group FCC(Cl)C(F)(F)F CNNJBYUJTYGLGG-UHFFFAOYSA-N 0.000 description 1
- XTRPJEPJFXGYCI-UHFFFAOYSA-N 3-chloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)CCl XTRPJEPJFXGYCI-UHFFFAOYSA-N 0.000 description 1
- SOPMTTFVKDXVEM-UHFFFAOYSA-N 3-chloro-1,1,1,2,3-pentafluoropropane Chemical group FC(Cl)C(F)C(F)(F)F SOPMTTFVKDXVEM-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 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 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10858508P | 2008-10-27 | 2008-10-27 | |
| US61/108,585 | 2008-10-27 | ||
| PCT/US2009/061828 WO2010062527A1 (en) | 2008-10-27 | 2009-10-23 | Conversion of hydrofluorochloropropanes to fluoropropenes |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020187033522A Division KR20180127527A (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20190086789A true KR20190086789A (ko) | 2019-07-23 |
Family
ID=41832362
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197020662A Ceased KR20190086789A (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
| KR1020177007120A Active KR101938099B1 (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
| KR1020117012022A Ceased KR20110089307A (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
| KR1020187033522A Ceased KR20180127527A (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177007120A Active KR101938099B1 (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
| KR1020117012022A Ceased KR20110089307A (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
| KR1020187033522A Ceased KR20180127527A (ko) | 2008-10-27 | 2009-10-23 | 하이드로플루오로클로로프로판의 플루오로프로펜으로의 전환 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2346800B1 (enExample) |
| JP (1) | JP5513513B2 (enExample) |
| KR (4) | KR20190086789A (enExample) |
| CN (2) | CN104262078A (enExample) |
| BR (1) | BRPI0914365A2 (enExample) |
| CA (1) | CA2736437A1 (enExample) |
| ES (1) | ES2391611T3 (enExample) |
| MX (1) | MX2011004319A (enExample) |
| PL (1) | PL2346800T3 (enExample) |
| RU (1) | RU2011121361A (enExample) |
| WO (1) | WO2010062527A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2760812A4 (en) * | 2011-09-30 | 2015-08-05 | Honeywell Int Inc | PROCESS FOR THE PREPARATION OF 2,3,3,3-TETRAFLUOROPROPES |
| KR20140110029A (ko) * | 2012-01-09 | 2014-09-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 반응기 패시베이션 방법 |
| CN105753641B (zh) * | 2014-12-13 | 2018-08-31 | 西安近代化学研究所 | 1,3,3,3-四氟丙烯的制备方法 |
| EP3297980A4 (en) | 2015-05-21 | 2018-12-26 | The Chemours Company FC, LLC | HYDROFLUORINATION OF 1233xf TO 244bb BY SbF5 |
| CN108640812A (zh) * | 2018-06-21 | 2018-10-12 | 岳阳景嘉化工有限公司 | 一种2，3-二氯丙烯的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5420368A (en) * | 1994-06-29 | 1995-05-30 | E. I. Du Pont De Nemours And Company | Production CF3 CH2 CF3 and/or CF3 CH═CF2 by the conversion of fluorinated ethers |
| US7230146B2 (en) * | 2003-10-27 | 2007-06-12 | Honeywell International Inc. | Process for producing fluoropropenes |
| US7592494B2 (en) * | 2003-07-25 | 2009-09-22 | Honeywell International Inc. | Process for the manufacture of 1,3,3,3-tetrafluoropropene |
| US7091388B2 (en) * | 2003-09-26 | 2006-08-15 | Honeywell International Inc. | Method of making 1,1,3,3,3-pentafluoropropene |
| US8084653B2 (en) * | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US20060094911A1 (en) * | 2004-10-29 | 2006-05-04 | Rao Velliyur N M | Noncatalytic manufacture of 1,1,3,3,3-pentafluoropropene from 1,1,1,3,3,3-hexafluoropropane |
| ATE515548T1 (de) * | 2004-12-21 | 2011-07-15 | Honeywell Int Inc | Stabilisierte iodkohlenstoffzusammensetzungen |
| LT2546224T (lt) * | 2006-01-03 | 2019-01-10 | Honeywell International Inc. | Fluorintų organinių junginių gamybos būdas |
| US8071825B2 (en) * | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| WO2008002499A2 (en) * | 2006-06-27 | 2008-01-03 | E. I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
-
2009
- 2009-10-23 WO PCT/US2009/061828 patent/WO2010062527A1/en not_active Ceased
- 2009-10-23 RU RU2011121361/04A patent/RU2011121361A/ru not_active Application Discontinuation
- 2009-10-23 MX MX2011004319A patent/MX2011004319A/es active IP Right Grant
- 2009-10-23 KR KR1020197020662A patent/KR20190086789A/ko not_active Ceased
- 2009-10-23 CN CN201410432880.XA patent/CN104262078A/zh active Pending
- 2009-10-23 EP EP09752568A patent/EP2346800B1/en active Active
- 2009-10-23 KR KR1020177007120A patent/KR101938099B1/ko active Active
- 2009-10-23 ES ES09752568T patent/ES2391611T3/es active Active
- 2009-10-23 CA CA2736437A patent/CA2736437A1/en not_active Abandoned
- 2009-10-23 KR KR1020117012022A patent/KR20110089307A/ko not_active Ceased
- 2009-10-23 KR KR1020187033522A patent/KR20180127527A/ko not_active Ceased
- 2009-10-23 PL PL09752568T patent/PL2346800T3/pl unknown
- 2009-10-23 CN CN200980142737.4A patent/CN102197012B/zh active Active
- 2009-10-23 JP JP2011533364A patent/JP5513513B2/ja active Active
- 2009-10-23 BR BRPI0914365A patent/BRPI0914365A2/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110089307A (ko) | 2011-08-05 |
| CN104262078A (zh) | 2015-01-07 |
| KR20180127527A (ko) | 2018-11-28 |
| BRPI0914365A2 (pt) | 2015-10-20 |
| EP2346800A1 (en) | 2011-07-27 |
| CN102197012B (zh) | 2014-10-01 |
| JP2012506863A (ja) | 2012-03-22 |
| WO2010062527A1 (en) | 2010-06-03 |
| KR101938099B1 (ko) | 2019-01-11 |
| MX2011004319A (es) | 2011-05-30 |
| JP5513513B2 (ja) | 2014-06-04 |
| RU2011121361A (ru) | 2012-12-10 |
| CA2736437A1 (en) | 2010-06-03 |
| KR20170032492A (ko) | 2017-03-22 |
| ES2391611T3 (es) | 2012-11-28 |
| EP2346800B1 (en) | 2012-08-29 |
| CN102197012A (zh) | 2011-09-21 |
| PL2346800T3 (pl) | 2013-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A107 | Divisional application of patent | ||
| PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 20190716 Application number text: 1020187033522 Filing date: 20181120 |
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| PG1501 | Laying open of application | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20190814 Comment text: Request for Examination of Application |
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| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20190923 Patent event code: PE09021S01D |
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| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20200121 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20190923 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |