ES2568619T3 - Procedimiento para preparar 2-cloro-3,3,3-trifluoropropeno - Google Patents
Procedimiento para preparar 2-cloro-3,3,3-trifluoropropeno Download PDFInfo
- Publication number
- ES2568619T3 ES2568619T3 ES13716454.7T ES13716454T ES2568619T3 ES 2568619 T3 ES2568619 T3 ES 2568619T3 ES 13716454 T ES13716454 T ES 13716454T ES 2568619 T3 ES2568619 T3 ES 2568619T3
- Authority
- ES
- Spain
- Prior art keywords
- reaction
- hcfo
- water
- reactor
- ppm
- 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.)
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- 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 52
- 238000000034 method Methods 0.000 title claims description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000000460 chlorine Substances 0.000 claims abstract description 37
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 29
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000007858 starting material Substances 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 21
- 239000007789 gas Substances 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 19
- 229910000856 hastalloy Inorganic materials 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 6
- JAQKPYNFGZPKTM-UHFFFAOYSA-N 1,2,3-trichloro-1,1-difluoropropane Chemical compound FC(F)(Cl)C(Cl)CCl JAQKPYNFGZPKTM-UHFFFAOYSA-N 0.000 description 6
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QJMGASHUZRHZBT-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)CCl QJMGASHUZRHZBT-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- -1 chloropropene compound Chemical class 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- GVVUPGXFVJLPDE-OWOJBTEDSA-N (e)-1,3,3,3-tetrachloroprop-1-ene Chemical compound Cl\C=C\C(Cl)(Cl)Cl GVVUPGXFVJLPDE-OWOJBTEDSA-N 0.000 description 2
- AUCDWYVJFVHEHQ-UHFFFAOYSA-N 1,1,2,3-tetrachloro-1-fluoropropane Chemical compound FC(Cl)(Cl)C(Cl)CCl AUCDWYVJFVHEHQ-UHFFFAOYSA-N 0.000 description 2
- PQUUGVDRLWLNGR-UHFFFAOYSA-N 2,3,3,3-tetrachloroprop-1-ene Chemical compound ClC(=C)C(Cl)(Cl)Cl PQUUGVDRLWLNGR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000008187 granular material Substances 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- 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
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261614102P | 2012-03-22 | 2012-03-22 | |
| US201261614102P | 2012-03-22 | ||
| PCT/JP2013/059161 WO2013141409A1 (en) | 2012-03-22 | 2013-03-21 | Process for preparing 2-chloro-3,3,3-trifluoropropene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2568619T3 true ES2568619T3 (es) | 2016-05-03 |
Family
ID=48096127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13716454.7T Active ES2568619T3 (es) | 2012-03-22 | 2013-03-21 | Procedimiento para preparar 2-cloro-3,3,3-trifluoropropeno |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9162945B2 (forum.php) |
| EP (1) | EP2828228B1 (forum.php) |
| JP (1) | JP5773086B2 (forum.php) |
| KR (1) | KR101613808B1 (forum.php) |
| CN (1) | CN104203881A (forum.php) |
| ES (1) | ES2568619T3 (forum.php) |
| IN (1) | IN2014KN01700A (forum.php) |
| WO (1) | WO2013141409A1 (forum.php) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140079508A (ko) | 2011-10-31 | 2014-06-26 | 다이킨 고교 가부시키가이샤 | 2-클로로-3,3,3-트리플루오로프로펜의 제조방법 |
| GB2559056B (en) | 2015-07-17 | 2019-09-11 | Mexichem Fluor Sa De Cv | Process for preparing 245cb and 1234yf from 243db |
| JP2017193511A (ja) | 2016-04-21 | 2017-10-26 | ダイキン工業株式会社 | ハイドロクロロフルオロカーボン及び／又はハイドロフルオロカーボンの製造方法 |
| JP6319535B1 (ja) | 2017-01-31 | 2018-05-09 | ダイキン工業株式会社 | 含フッ素ハロゲン化炭化水素の製造方法 |
| JP7151257B2 (ja) * | 2018-08-07 | 2022-10-12 | Ａｇｃ株式会社 | ２－クロロ－３，３－ジフルオロプロペンの製造方法、２－クロロ－１，１，２－トリフルオロプロパンの製造方法、２，３，３－トリフルオロプロペンの製造方法、１，２－ジクロロ－２，３，３－トリフルオロプロパンの製造方法、１－クロロ－２，３，３－トリフルオロプロペンの製造方法 |
| CN114599762A (zh) * | 2019-11-06 | 2022-06-07 | 霍尼韦尔国际公司 | 2-氯-3,3,3-三氟丙烯（hcfo-1233xf）和水的共沸物或类共沸物组合物 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9303208A (es) | 1992-06-17 | 1994-01-31 | Alliend Signal Inc | Mejoras en un proceso de fluorizacion en fase de vapor. |
| EP0777637A1 (en) | 1994-08-17 | 1997-06-11 | AlliedSignal Inc. | A process for preparing 1,1,1-trifluoroethane |
| JP4397687B2 (ja) | 2001-06-28 | 2010-01-13 | ハネウェル・インターナショナル・インコーポレーテッド | 弗素化触媒を調製する方法 |
| US8084653B2 (en) * | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US8058486B2 (en) | 2004-04-29 | 2011-11-15 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| PL3336073T3 (pl) | 2006-01-03 | 2023-03-20 | Honeywell International Inc. | Sposób wytwarzania fluorowanych związków organicznych |
| US8071825B2 (en) | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8952208B2 (en) | 2006-01-03 | 2015-02-10 | Honeywell International Inc. | Method for prolonging a catalyst's life during hydrofluorination |
| CN101528645B (zh) | 2006-10-31 | 2013-10-30 | 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 |
| US8076521B2 (en) | 2007-06-27 | 2011-12-13 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| US8563789B2 (en) * | 2007-06-27 | 2013-10-22 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| US7795480B2 (en) | 2007-07-25 | 2010-09-14 | Honeywell International Inc. | Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) |
| KR101392589B1 (ko) * | 2009-04-23 | 2014-05-21 | 다이킨 고교 가부시키가이샤 | 2-클로로-3,3,3-트리플루오로프로펜의 제조 방법 |
| US8618340B2 (en) * | 2009-11-03 | 2013-12-31 | Honeywell International Inc. | Integrated process for fluoro-olefin production |
| WO2011077191A1 (en) | 2009-12-23 | 2011-06-30 | Arkema France | Catalytic gas phase fluorination of 1230xa to 1234yf |
| US8680345B2 (en) * | 2011-01-07 | 2014-03-25 | Honeywell International Inc. | Low temperature production of 2-chloro-3,3,3-trifluoropropene |
| KR20140071457A (ko) | 2011-09-30 | 2014-06-11 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜의 제조 방법 |
| KR20140079508A (ko) * | 2011-10-31 | 2014-06-26 | 다이킨 고교 가부시키가이샤 | 2-클로로-3,3,3-트리플루오로프로펜의 제조방법 |
| CN107021868A (zh) | 2013-03-12 | 2017-08-08 | 霍尼韦尔国际公司 | 用于减少1233xf氢氟化为244bb过程中245cb形成的方法 |
-
2013
- 2013-03-21 EP EP13716454.7A patent/EP2828228B1/en not_active Revoked
- 2013-03-21 WO PCT/JP2013/059161 patent/WO2013141409A1/en active Application Filing
- 2013-03-21 US US14/379,044 patent/US9162945B2/en active Active
- 2013-03-21 CN CN201380015774.5A patent/CN104203881A/zh active Pending
- 2013-03-21 IN IN1700KON2014 patent/IN2014KN01700A/en unknown
- 2013-03-21 ES ES13716454.7T patent/ES2568619T3/es active Active
- 2013-03-21 KR KR1020147027151A patent/KR101613808B1/ko active Active
- 2013-03-21 JP JP2014540251A patent/JP5773086B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015506909A (ja) | 2015-03-05 |
| EP2828228A1 (en) | 2015-01-28 |
| KR20140130732A (ko) | 2014-11-11 |
| US9162945B2 (en) | 2015-10-20 |
| US20150057473A1 (en) | 2015-02-26 |
| KR101613808B1 (ko) | 2016-04-19 |
| WO2013141409A1 (en) | 2013-09-26 |
| IN2014KN01700A (forum.php) | 2015-10-23 |
| EP2828228B1 (en) | 2016-02-17 |
| CN104203881A (zh) | 2014-12-10 |
| JP5773086B2 (ja) | 2015-09-02 |
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