JP2016511285A5 - - Google Patents
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- JP2016511285A5 JP2016511285A5 JP2016501546A JP2016501546A JP2016511285A5 JP 2016511285 A5 JP2016511285 A5 JP 2016511285A5 JP 2016501546 A JP2016501546 A JP 2016501546A JP 2016501546 A JP2016501546 A JP 2016501546A JP 2016511285 A5 JP2016511285 A5 JP 2016511285A5
- Authority
- JP
- Japan
- Prior art keywords
- halogenated
- chcl
- tetrafluoropropene
- mixture
- impurity
- 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
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- 238000000034 method Methods 0.000 claims description 82
- 239000012535 impurity Substances 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 60
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 57
- 239000003463 adsorbent Substances 0.000 claims description 28
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000010457 zeolite Substances 0.000 claims description 18
- 229910021536 Zeolite Inorganic materials 0.000 claims description 17
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 17
- -1 olefin compound Chemical class 0.000 claims description 12
- 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 description 10
- 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 9
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 229920010524 Syndiotactic polystyrene Polymers 0.000 claims description 6
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229920006037 cross link polymer Polymers 0.000 claims description 6
- 239000012025 fluorinating agent Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- CDOOAUSHHFGWSA-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropene Chemical compound FC=CC(F)(F)F CDOOAUSHHFGWSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 3
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910021555 Chromium Chloride Inorganic materials 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- MLDREZJSPHHHPU-UHFFFAOYSA-N [Fe+3].FOF Chemical compound [Fe+3].FOF MLDREZJSPHHHPU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- UGWBWPXTGFPEFG-UHFFFAOYSA-N chloro hypochlorite chromium Chemical compound [Cr].ClOCl UGWBWPXTGFPEFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 229910021563 chromium fluoride Inorganic materials 0.000 claims description 3
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 3
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 3
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- KQOALLXEWMGDKG-UHFFFAOYSA-N chloro hypochlorite iron(3+) Chemical compound [Fe+3].ClOCl KQOALLXEWMGDKG-UHFFFAOYSA-N 0.000 claims 2
- 239000002808 molecular sieve Substances 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 2
- 238000001179 sorption measurement Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 27
- 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 5
- 239000005977 Ethylene Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- YPLPZEKZDGQOOQ-UHFFFAOYSA-M iron oxychloride Chemical compound [O][Fe]Cl YPLPZEKZDGQOOQ-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361792669P | 2013-03-15 | 2013-03-15 | |
| US61/792,669 | 2013-03-15 | ||
| PCT/US2014/024467 WO2014150889A1 (en) | 2013-03-15 | 2014-03-12 | Methods for removing halogenated ethylene impurities in 2,3,3,3-tetrafluoropropene product |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018200956A Division JP2019048827A (ja) | 2013-03-15 | 2018-10-25 | ２，３，３，３−テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016511285A JP2016511285A (ja) | 2016-04-14 |
| JP2016511285A5 true JP2016511285A5 (enExample) | 2018-05-31 |
Family
ID=51530207
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016501546A Pending JP2016511285A (ja) | 2013-03-15 | 2014-03-12 | ２，３，３，３−テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
| JP2018200956A Pending JP2019048827A (ja) | 2013-03-15 | 2018-10-25 | ２，３，３，３−テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
| JP2020164391A Pending JP2021006551A (ja) | 2013-03-15 | 2020-09-30 | ２，３，３，３−テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
| JP2022115527A Active JP7470744B2 (ja) | 2013-03-15 | 2022-07-20 | ２，３，３，３－テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
| JP2024061949A Pending JP2024096818A (ja) | 2013-03-15 | 2024-04-08 | ２，３，３，３－テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018200956A Pending JP2019048827A (ja) | 2013-03-15 | 2018-10-25 | ２，３，３，３−テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
| JP2020164391A Pending JP2021006551A (ja) | 2013-03-15 | 2020-09-30 | ２，３，３，３−テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
| JP2022115527A Active JP7470744B2 (ja) | 2013-03-15 | 2022-07-20 | ２，３，３，３－テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
| JP2024061949A Pending JP2024096818A (ja) | 2013-03-15 | 2024-04-08 | ２，３，３，３－テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US9447004B2 (enExample) |
| EP (3) | EP3925946A1 (enExample) |
| JP (5) | JP2016511285A (enExample) |
| KR (5) | KR20250152674A (enExample) |
| CN (1) | CN105026351A (enExample) |
| ES (1) | ES2972152T3 (enExample) |
| MX (1) | MX378625B (enExample) |
| PL (1) | PL2970058T3 (enExample) |
| PT (1) | PT2970058T (enExample) |
| WO (1) | WO2014150889A1 (enExample) |
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| KR20250152674A (ko) * | 2013-03-15 | 2025-10-23 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜 생성물에서 할로겐화 에틸렌 불순물을 제거하는 방법 |
| GB2528690B (en) | 2014-07-28 | 2017-03-01 | Mexichem Amanco Holding Sa | Process for preparing a (hydro)(chloro)fluoroalkene |
| JP5915808B1 (ja) * | 2014-12-24 | 2016-05-11 | ダイキン工業株式会社 | 反応に用いた触媒の取り出し方法 |
| JP6028825B2 (ja) * | 2015-03-31 | 2016-11-24 | ダイキン工業株式会社 | ハイドロフルオロオレフィン化合物を含有する組成物 |
| CN107635955A (zh) | 2015-05-21 | 2018-01-26 | 科慕埃弗西有限公司 | 通过SbF5进行的1233xf至244bb的氢氟化 |
| US9938213B2 (en) * | 2015-08-19 | 2018-04-10 | Honeywell International Inc. | Methods for removing acidic impurities from halogenated propenes |
| CN108349755A (zh) * | 2015-11-05 | 2018-07-31 | 霍尼韦尔国际公司 | 用于从通过1230xa得到1234yf的方法的无水或含水氢氯酸副产物中去除氟化有机物的方法 |
| CN106345264B (zh) * | 2016-07-19 | 2018-10-30 | 浙江博瑞电子科技有限公司 | 一种使用杂质分解剂的有机氟气体的提纯方法 |
| WO2018085512A2 (en) * | 2016-11-02 | 2018-05-11 | Honeywell International Inc. | Process for reducing 3,3,3-trifluoropropyne in 2,3,3,3-tetrafluoropropene |
| JP7003934B2 (ja) * | 2016-11-15 | 2022-02-04 | Ａｇｃ株式会社 | １－クロロ－２，３，３－トリフルオロプロペンの製造方法 |
| JP7024727B2 (ja) * | 2016-11-30 | 2022-02-24 | Ａｇｃ株式会社 | １－クロロ－２，３，３－トリフルオロプロペンの製造方法 |
| CN107008103A (zh) * | 2017-05-05 | 2017-08-04 | 上海化工研究院有限公司 | 一种物理吸附脱出气相中挥发性氯代烃的方法 |
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| CN109985663B (zh) * | 2017-12-29 | 2020-09-08 | 华中科技大学 | 一种对一锅法原位合成的Cu-SSZ-13分子筛进行后处理的方法 |
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| CN119118781A (zh) | 2018-06-06 | 2024-12-13 | 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 |
| US10941091B2 (en) * | 2018-12-03 | 2021-03-09 | Honeywell International Inc. | Processes for producing high-purity trifluoroiodomethane |
| EP3834914A1 (en) * | 2019-12-13 | 2021-06-16 | General Electric Technology GmbH | Use of a transition metal oxide for removing fluorinated by-products from a gas, device and method for removing such by-products |
| CN112169767B (zh) * | 2020-09-30 | 2022-06-10 | 中船(邯郸)派瑞特种气体股份有限公司 | 一种去除六氟丁二烯中氯烃杂质的吸附剂 |
| US12083493B2 (en) * | 2021-03-04 | 2024-09-10 | American Air Liquide, Inc. | Selective adsorption of halocarbon impurities containing cl, br and i in fluorocarbons or hydrofluorocarbons using adsorbent supported metal oxide |
| JP7441985B2 (ja) * | 2022-02-21 | 2024-03-01 | ダイキン工業株式会社 | 分離方法 |
| JP7744595B2 (ja) * | 2023-08-23 | 2025-09-26 | ダイキン工業株式会社 | 分離方法 |
| TW202513512A (zh) * | 2023-09-29 | 2025-04-01 | 美商科慕Ｆｃ有限責任公司 | 用於純化共同生產的ｈｆｏ－ｅ／ｚ－１１３２之程序及其組成物 |
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| JP5747684B2 (ja) | 2010-09-14 | 2015-07-15 | セントラル硝子株式会社 | ヒドロフルオロカーボンまたはヒドロクロロフルオロカーボンの脱水方法、および該脱水方法を用いた１，３，３，３−テトラフルオロプロペンの製造方法 |
| JP5817373B2 (ja) | 2010-11-10 | 2015-11-18 | セントラル硝子株式会社 | トランス−１，３，３，３−テトラフルオロプロペンの製造方法 |
| US8337595B2 (en) | 2011-04-20 | 2012-12-25 | Honeywell International Inc. | Purification of trans-1,3,3,3-tetrafluoropropene |
| US8570723B2 (en) | 2011-05-18 | 2013-10-29 | Myerchin Enterprises, Inc. | Actuated hinge and cable assembly for use with computer display monitors |
| GB2492847A (en) | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| US8796493B2 (en) * | 2011-09-30 | 2014-08-05 | Honeywell International Inc. | Methods to separate halogentated olefins from 2-chloro-1,1,1,2-tetrafluoropropane using a solid adsorbent |
| JP5899974B2 (ja) * | 2012-02-02 | 2016-04-06 | セントラル硝子株式会社 | （ｅ）−１−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
| JP2013241390A (ja) * | 2012-04-27 | 2013-12-05 | Asahi Glass Co Ltd | フルオロオレフィンの精製方法、およびフルオロオレフィンの製造方法 |
| KR20250152674A (ko) * | 2013-03-15 | 2025-10-23 | 허니웰 인터내셔날 인코포레이티드 | 2,3,3,3-테트라플루오로프로펜 생성물에서 할로겐화 에틸렌 불순물을 제거하는 방법 |
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2014
- 2014-03-12 KR KR1020257033234A patent/KR20250152674A/ko active Pending
- 2014-03-12 KR KR1020157029299A patent/KR20150131272A/ko not_active Abandoned
- 2014-03-12 PT PT147677694T patent/PT2970058T/pt unknown
- 2014-03-12 KR KR1020217033846A patent/KR102554663B1/ko active Active
- 2014-03-12 PL PL14767769.4T patent/PL2970058T3/pl unknown
- 2014-03-12 WO PCT/US2014/024467 patent/WO2014150889A1/en not_active Ceased
- 2014-03-12 EP EP21176638.1A patent/EP3925946A1/en active Pending
- 2014-03-12 EP EP25152123.3A patent/EP4549417A3/en active Pending
- 2014-03-12 CN CN201480015919.6A patent/CN105026351A/zh active Pending
- 2014-03-12 US US14/206,026 patent/US9447004B2/en active Active
- 2014-03-12 JP JP2016501546A patent/JP2016511285A/ja active Pending
- 2014-03-12 KR KR1020257033235A patent/KR20250150693A/ko active Pending
- 2014-03-12 KR KR1020237022959A patent/KR20230107715A/ko not_active Ceased
- 2014-03-12 ES ES14767769T patent/ES2972152T3/es active Active
- 2014-03-12 MX MX2015010801A patent/MX378625B/es unknown
- 2014-03-12 EP EP14767769.4A patent/EP2970058B1/en active Active
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2016
- 2016-09-16 US US15/267,599 patent/US10099977B2/en active Active
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2018
- 2018-10-12 US US16/158,567 patent/US10676415B2/en active Active
- 2018-10-25 JP JP2018200956A patent/JP2019048827A/ja active Pending
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2020
- 2020-09-30 JP JP2020164391A patent/JP2021006551A/ja active Pending
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2022
- 2022-07-20 JP JP2022115527A patent/JP7470744B2/ja active Active
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2024
- 2024-04-08 JP JP2024061949A patent/JP2024096818A/ja active Pending
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