JP2017523954A5 - - Google Patents
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- JP2017523954A5 JP2017523954A5 JP2016573570A JP2016573570A JP2017523954A5 JP 2017523954 A5 JP2017523954 A5 JP 2017523954A5 JP 2016573570 A JP2016573570 A JP 2016573570A JP 2016573570 A JP2016573570 A JP 2016573570A JP 2017523954 A5 JP2017523954 A5 JP 2017523954A5
- Authority
- JP
- Japan
- Prior art keywords
- hydro
- catalyst
- chloro
- hcl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 32
- 239000003054 catalyst Substances 0.000 claims 13
- 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 claims 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 8
- 230000001172 regenerating effect Effects 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 239000012320 chlorinating reagent Substances 0.000 claims 4
- 238000005660 chlorination reaction Methods 0.000 claims 4
- 238000007033 dehydrochlorination reaction Methods 0.000 claims 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 claims 3
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical group FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims 3
- BLEZTPDKUBSTII-UHFFFAOYSA-N 1-chloro-1-fluoroprop-1-ene Chemical compound CC=C(F)Cl BLEZTPDKUBSTII-UHFFFAOYSA-N 0.000 claims 3
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 claims 3
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims 3
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- -1 fluoro alkene Chemical class 0.000 claims 3
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims 2
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical group CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims 2
- PLTIOZOVDUUXDQ-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CC(Cl)Cl PLTIOZOVDUUXDQ-UHFFFAOYSA-N 0.000 claims 2
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical group FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 229960002003 hydrochlorothiazide Drugs 0.000 claims 2
- 239000011261 inert gas Substances 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- QJMGASHUZRHZBT-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)CCl QJMGASHUZRHZBT-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1413340.9 | 2014-07-28 | ||
| GB1413340.9A GB2528690B (en) | 2014-07-28 | 2014-07-28 | Process for preparing a (hydro)(chloro)fluoroalkene |
| PCT/GB2015/052165 WO2016016625A1 (en) | 2014-07-28 | 2015-07-27 | Process for the preparation of halogenated alkenes by dehydrohalogenation of halogenated alkanes |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018084183A Division JP6674974B2 (ja) | 2014-07-28 | 2018-04-25 | ハロゲン化アルカンの脱ハロゲン化水素化によるハロゲン化アルケンの調製のための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017523954A JP2017523954A (ja) | 2017-08-24 |
| JP2017523954A5 true JP2017523954A5 (enExample) | 2018-03-29 |
| JP6334741B2 JP6334741B2 (ja) | 2018-05-30 |
Family
ID=51587349
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016573570A Active JP6334741B2 (ja) | 2014-07-28 | 2015-07-27 | ハロゲン化アルカンの脱ハロゲン化水素化によるハロゲン化アルケンの調製のための方法 |
| JP2018084183A Active JP6674974B2 (ja) | 2014-07-28 | 2018-04-25 | ハロゲン化アルカンの脱ハロゲン化水素化によるハロゲン化アルケンの調製のための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018084183A Active JP6674974B2 (ja) | 2014-07-28 | 2018-04-25 | ハロゲン化アルカンの脱ハロゲン化水素化によるハロゲン化アルケンの調製のための方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9944578B2 (enExample) |
| EP (2) | EP3077352B1 (enExample) |
| JP (2) | JP6334741B2 (enExample) |
| ES (2) | ES2687400T3 (enExample) |
| GB (1) | GB2528690B (enExample) |
| WO (1) | WO2016016625A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6763431B2 (ja) * | 2016-07-11 | 2020-09-30 | ダイキン工業株式会社 | １−クロロ−１，２−ジフルオロエチレンの製造方法 |
| CN107324968B (zh) | 2017-07-24 | 2020-08-04 | 浙江衢化氟化学有限公司 | 一种联产低碳发泡剂的方法 |
| US10351494B1 (en) * | 2018-01-08 | 2019-07-16 | Honeywell International Inc. | Systems and methods for reducing the formation of impurities during 244bb dehydrochlorination to 1234yf |
| JP7166889B2 (ja) * | 2018-11-20 | 2022-11-08 | ダイキン工業株式会社 | １，２－ジフルオロエチレンの製造方法 |
| FR3094714B1 (fr) * | 2019-04-03 | 2021-04-23 | Arkema France | Procédé de purification du 1-chloro-3,3,3-trifluoropropène |
| US11795125B2 (en) * | 2022-01-26 | 2023-10-24 | Honeywell International Inc. | Integrated process for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from a mixture of high-boiling fluorinated components |
| CN115572208B (zh) * | 2022-08-29 | 2024-09-17 | 西安近代化学研究所 | 一种2-氯-3,3,3-三氟丙烯的制备方法 |
| CN116178097B (zh) * | 2023-04-24 | 2023-07-07 | 山东澳帆新材料有限公司 | 一种高选择性制备2-氯-1,1,1,2-四氟丙烷的方法 |
| CN117599817B (zh) * | 2023-10-30 | 2025-10-21 | 浙江工业大学 | 一种聚磷酸表面修饰的金属基催化剂及其制备方法和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4001779A1 (de) * | 1989-02-01 | 1990-08-02 | Inst Francais Du Petrole | Verfahren zur regenerierung eines katalysators fuer die reformierung oder die herstellung aromatischer kohlenwasserstoffe |
| US5202102A (en) * | 1991-05-22 | 1993-04-13 | The Dow Chemical Company | Gas phase dehydrohalogenation using a pretreated catalyst |
| US8530708B2 (en) | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
| JP5270361B2 (ja) * | 2005-11-03 | 2013-08-21 | ハネウェル・インターナショナル・インコーポレーテッド | フッ素化有機化合物の製造方法 |
| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| US7884254B2 (en) * | 2007-08-08 | 2011-02-08 | Honeywell International Inc. | Dehydrochlorination of hydrochlorofluorocarbons using pre-treated activated carbon catalysts |
| WO2011130108A1 (en) * | 2010-04-14 | 2011-10-20 | Arkema Inc. | Process for the manufacture of tetrafluoroolefins |
| US8653309B2 (en) * | 2011-04-20 | 2014-02-18 | Honeywell International Inc. | Process for producing trans-1233zd |
| 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 |
| JP6223346B2 (ja) | 2011-10-14 | 2017-11-01 | 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 |
| US8829254B2 (en) * | 2012-02-14 | 2014-09-09 | Honeywell International Inc. | Process for making 1,3,3,3-tetrafluoropropene |
| US8889924B2 (en) * | 2012-02-14 | 2014-11-18 | Honeywell International Inc. | Process for the production of 1,3,3,3-tetrafluoropropene |
| JP6107467B2 (ja) * | 2012-06-29 | 2017-04-05 | セントラル硝子株式会社 | １−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
| KR20250152674A (ko) * | 2013-03-15 | 2025-10-23 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜 생성물에서 할로겐화 에틸렌 불순물을 제거하는 방법 |
-
2014
- 2014-07-28 GB GB1413340.9A patent/GB2528690B/en active Active
-
2015
- 2015-07-27 WO PCT/GB2015/052165 patent/WO2016016625A1/en not_active Ceased
- 2015-07-27 ES ES15756440.2T patent/ES2687400T3/es active Active
- 2015-07-27 ES ES18167117T patent/ES2811050T3/es active Active
- 2015-07-27 US US15/329,392 patent/US9944578B2/en active Active
- 2015-07-27 EP EP15756440.2A patent/EP3077352B1/en active Active
- 2015-07-27 JP JP2016573570A patent/JP6334741B2/ja active Active
- 2015-07-27 EP EP18167117.3A patent/EP3366662B1/en active Active
-
2018
- 2018-04-16 US US15/953,743 patent/US10442743B2/en active Active
- 2018-04-25 JP JP2018084183A patent/JP6674974B2/ja active Active
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