CN104262078A - 氢氟氯丙烷向氟丙烯的转化 - Google Patents
氢氟氯丙烷向氟丙烯的转化 Download PDFInfo
- Publication number
- CN104262078A CN104262078A CN201410432880.XA CN201410432880A CN104262078A CN 104262078 A CN104262078 A CN 104262078A CN 201410432880 A CN201410432880 A CN 201410432880A CN 104262078 A CN104262078 A CN 104262078A
- Authority
- CN
- China
- Prior art keywords
- chloropropane
- fluoro
- fluorine
- reaction vessel
- tetra
- 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.)
- Pending
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 58
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 238000000197 pyrolysis Methods 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 37
- VEDYTOUMKRUZAN-UHFFFAOYSA-N ClCCC.[F] Chemical compound ClCCC.[F] VEDYTOUMKRUZAN-UHFFFAOYSA-N 0.000 claims description 36
- QBTUCBKAWGUMMK-UHFFFAOYSA-N C=CC.[F] Chemical group C=CC.[F] QBTUCBKAWGUMMK-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 23
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims description 13
- PFDZQZAOZNELDX-UHFFFAOYSA-N 1-chloro-3-fluoropropane Chemical compound FCCCCl PFDZQZAOZNELDX-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000006200 vaporizer Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000012159 carrier gas Substances 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 235000011089 carbon dioxide Nutrition 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 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 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000000463 material Substances 0.000 description 9
- 238000007033 dehydrochlorination reaction Methods 0.000 description 7
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical group CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910000990 Ni alloy Inorganic materials 0.000 description 5
- 229910001026 inconel Inorganic materials 0.000 description 5
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 229910000792 Monel Inorganic materials 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 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
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JSECXTYNFBONSF-UHFFFAOYSA-N 3-chloro-1,1,1,2-tetrafluoropropane Chemical compound ClCC(F)C(F)(F)F JSECXTYNFBONSF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) 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
- 150000001336 alkenes Chemical class 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
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 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
- 238000005554 pickling Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 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
- 238000010189 synthetic method 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10858508P | 2008-10-27 | 2008-10-27 | |
| US61/108585 | 2008-10-27 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980142737.4A Division CN102197012B (zh) | 2008-10-27 | 2009-10-23 | 氢氟氯丙烷向氟丙烯的转化 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104262078A true CN104262078A (zh) | 2015-01-07 |
Family
ID=41832362
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980142737.4A Active CN102197012B (zh) | 2008-10-27 | 2009-10-23 | 氢氟氯丙烷向氟丙烯的转化 |
| CN201410432880.XA Pending CN104262078A (zh) | 2008-10-27 | 2009-10-23 | 氢氟氯丙烷向氟丙烯的转化 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980142737.4A Active CN102197012B (zh) | 2008-10-27 | 2009-10-23 | 氢氟氯丙烷向氟丙烯的转化 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2346800B1 (enExample) |
| JP (1) | JP5513513B2 (enExample) |
| KR (4) | KR101938099B1 (enExample) |
| CN (2) | CN102197012B (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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP2802549B1 (en) * | 2012-01-09 | 2019-03-27 | The Chemours Company FC, LLC | Process for reactor passivation |
| 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 |
| MX395316B (es) | 2015-05-21 | 2025-03-25 | Chemours Co Fc Llc | Hidrofluoracion de 1233xf a 244bb por sbf5. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050070746A1 (en) * | 2003-09-26 | 2005-03-31 | Honeywell International,Inc. | Method of making 1,1,3,3,3-pentafluoropropene |
| WO2007079431A2 (en) * | 2006-01-03 | 2007-07-12 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| CN101133008A (zh) * | 2004-10-29 | 2008-02-27 | 纳幕尔杜邦公司 | 从1,1,1,3,3,3-六氟丙烷非催化法生产1,1,3,3,3-五氟丙烯 |
Family Cites Families (7)
| 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 |
| US8084653B2 (en) * | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| WO2006069362A2 (en) * | 2004-12-21 | 2006-06-29 | Honeywell International Inc. | Stabilized iodocarbon compositions |
| US8071825B2 (en) * | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| JP2009542650A (ja) * | 2006-06-27 | 2009-12-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | テトラフルオロプロペン製造方法 |
-
2009
- 2009-10-23 PL PL09752568T patent/PL2346800T3/pl unknown
- 2009-10-23 WO PCT/US2009/061828 patent/WO2010062527A1/en not_active Ceased
- 2009-10-23 CN CN200980142737.4A patent/CN102197012B/zh active Active
- 2009-10-23 MX MX2011004319A patent/MX2011004319A/es active IP Right Grant
- 2009-10-23 ES ES09752568T patent/ES2391611T3/es active Active
- 2009-10-23 KR KR1020177007120A patent/KR101938099B1/ko active Active
- 2009-10-23 CN CN201410432880.XA patent/CN104262078A/zh active Pending
- 2009-10-23 RU RU2011121361/04A patent/RU2011121361A/ru not_active Application Discontinuation
- 2009-10-23 BR BRPI0914365A patent/BRPI0914365A2/pt not_active IP Right Cessation
- 2009-10-23 KR KR1020187033522A patent/KR20180127527A/ko not_active Ceased
- 2009-10-23 KR KR1020197020662A patent/KR20190086789A/ko not_active Ceased
- 2009-10-23 JP JP2011533364A patent/JP5513513B2/ja active Active
- 2009-10-23 KR KR1020117012022A patent/KR20110089307A/ko not_active Ceased
- 2009-10-23 CA CA2736437A patent/CA2736437A1/en not_active Abandoned
- 2009-10-23 EP EP09752568A patent/EP2346800B1/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050070746A1 (en) * | 2003-09-26 | 2005-03-31 | Honeywell International,Inc. | Method of making 1,1,3,3,3-pentafluoropropene |
| CN101133008A (zh) * | 2004-10-29 | 2008-02-27 | 纳幕尔杜邦公司 | 从1,1,1,3,3,3-六氟丙烷非催化法生产1,1,3,3,3-五氟丙烯 |
| WO2007079431A2 (en) * | 2006-01-03 | 2007-07-12 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2736437A1 (en) | 2010-06-03 |
| KR101938099B1 (ko) | 2019-01-11 |
| BRPI0914365A2 (pt) | 2015-10-20 |
| CN102197012A (zh) | 2011-09-21 |
| ES2391611T3 (es) | 2012-11-28 |
| PL2346800T3 (pl) | 2013-01-31 |
| KR20190086789A (ko) | 2019-07-23 |
| WO2010062527A1 (en) | 2010-06-03 |
| KR20180127527A (ko) | 2018-11-28 |
| CN102197012B (zh) | 2014-10-01 |
| EP2346800A1 (en) | 2011-07-27 |
| EP2346800B1 (en) | 2012-08-29 |
| MX2011004319A (es) | 2011-05-30 |
| RU2011121361A (ru) | 2012-12-10 |
| KR20110089307A (ko) | 2011-08-05 |
| KR20170032492A (ko) | 2017-03-22 |
| JP2012506863A (ja) | 2012-03-22 |
| JP5513513B2 (ja) | 2014-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20171227 Address after: Delaware, USA Applicant after: THE CHEMOURS COMPANY FC, LLC Address before: Wilmington, Delaware, USA Applicant before: E. I. du Pont de Nemours and Co. |
|
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150107 |