JP2019501914A5 - - Google Patents
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- Publication number
- JP2019501914A5 JP2019501914A5 JP2018533861A JP2018533861A JP2019501914A5 JP 2019501914 A5 JP2019501914 A5 JP 2019501914A5 JP 2018533861 A JP2018533861 A JP 2018533861A JP 2018533861 A JP2018533861 A JP 2018533861A JP 2019501914 A5 JP2019501914 A5 JP 2019501914A5
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- halogenated
- reaction mixture
- combination
- liquid phase
- 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
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- 238000000034 method Methods 0.000 claims description 105
- 239000000047 product Substances 0.000 claims description 38
- 239000011541 reaction mixture Substances 0.000 claims description 31
- 239000007791 liquid phase Substances 0.000 claims description 27
- 150000001336 alkenes Chemical class 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 16
- 239000010949 copper Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000012071 phase Substances 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 5
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 claims description 4
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical group ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 claims description 4
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 4
- 239000000956 alloy Substances 0.000 claims description 4
- 229910045601 alloy Inorganic materials 0.000 claims description 4
- 239000003729 cation exchange resin Substances 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 4
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 claims description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 2
- OXFUXNFMHFCELM-UHFFFAOYSA-N tripropan-2-yl phosphate Chemical compound CC(C)OP(=O)(OC(C)C)OC(C)C OXFUXNFMHFCELM-UHFFFAOYSA-N 0.000 claims description 2
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 claims description 2
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 claims description 2
- NZIQBDROTUFRHZ-UHFFFAOYSA-N tritert-butyl phosphite Chemical compound CC(C)(C)OP(OC(C)(C)C)OC(C)(C)C NZIQBDROTUFRHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001503 Glucan Polymers 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- -1 alkene fluoride Chemical class 0.000 description 6
- 229920005990 polystyrene resin Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- 150000001734 carboxylic acid salts Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- 239000000011 acetone peroxide Substances 0.000 description 1
- 235000019401 acetone peroxide Nutrition 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
Images
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662274601P | 2016-01-04 | 2016-01-04 | |
| US62/274,601 | 2016-01-04 | ||
| US201662277400P | 2016-01-11 | 2016-01-11 | |
| US62/277,400 | 2016-01-11 | ||
| PCT/US2017/012223 WO2017120264A1 (en) | 2016-01-04 | 2017-01-04 | Improved processes for preparing halogenated alkanes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019501914A JP2019501914A (ja) | 2019-01-24 |
| JP2019501914A5 true JP2019501914A5 (enExample) | 2020-02-20 |
| JP6843866B2 JP6843866B2 (ja) | 2021-03-17 |
Family
ID=57868382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018533861A Active JP6843866B2 (ja) | 2016-01-04 | 2017-01-04 | ハロゲン化アルカンを調製するための改善されたプロセス |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10513478B2 (enExample) |
| EP (2) | EP3770139A1 (enExample) |
| JP (1) | JP6843866B2 (enExample) |
| CN (1) | CN108368012B (enExample) |
| CA (1) | CA3008291A1 (enExample) |
| WO (1) | WO2017120264A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021520370A (ja) * | 2018-04-03 | 2021-08-19 | ブルー キューブ アイピー エルエルシー | ジェットループ反応器中の塩素化アルカンの苛性脱塩化水素により塩素化アルケンを調製するための改善されたプロセス |
| WO2019195254A1 (en) * | 2018-04-03 | 2019-10-10 | Blue Cube Ip Llc | Method for production of a halogenated alkane using an absorber-reactor combination |
| CN111056913A (zh) * | 2019-12-09 | 2020-04-24 | 宁波巨化化工科技有限公司 | 一种1，1，1，3-四氯丙烷的连续生产方法 |
| CN114605225A (zh) * | 2020-12-04 | 2022-06-10 | 中国科学院上海有机化学研究所 | 一种连续合成1,1,1,3,3-五氯丙烷的方法 |
| CN114605226B (zh) * | 2020-12-04 | 2025-12-02 | 中国科学院上海有机化学研究所 | 一种连续合成1,1,1,3-四氯丙烷的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650914A (en) | 1983-07-06 | 1987-03-17 | Monsanto Company | Process for producing 1,1,2,3-tetrachloropropene |
| DE3731995A1 (de) * | 1987-09-23 | 1989-04-06 | Bayer Ag | Verfahren zum entfernen von eisenhalogeniden aus fluessigen, mit wasser nicht mischbaren organischen stoffen |
| US6313360B1 (en) | 2000-09-29 | 2001-11-06 | Vulcan Materials Company | Process for the manufacture of 1, 1, 1, 3, 3-pentachloropropane |
| EP2447238A4 (en) * | 2009-06-24 | 2012-12-19 | Tokuyama Corp | METHOD FOR PRODUCING CHLORINE-CARBONATED HYDROGEN |
| EP2714631B1 (en) * | 2011-05-31 | 2020-05-13 | Blue Cube IP LLC | Process for the production of chlorinated propenes |
| JP5741516B2 (ja) * | 2012-04-19 | 2015-07-01 | ダイキン工業株式会社 | フルオロアルキルアイオダイドの製造方法 |
| US8907147B2 (en) * | 2013-02-04 | 2014-12-09 | Honeywell International Inc. | Synthesis of 1,1,2,3-tetrachloropropene |
| CN104557401B (zh) * | 2015-01-23 | 2017-03-29 | 浙江大学 | 使用移动床技术增产丙烯和芳烃的方法 |
-
2017
- 2017-01-04 CN CN201780004718.XA patent/CN108368012B/zh active Active
- 2017-01-04 EP EP20192243.2A patent/EP3770139A1/en active Pending
- 2017-01-04 WO PCT/US2017/012223 patent/WO2017120264A1/en not_active Ceased
- 2017-01-04 CA CA3008291A patent/CA3008291A1/en not_active Abandoned
- 2017-01-04 JP JP2018533861A patent/JP6843866B2/ja active Active
- 2017-01-04 US US16/067,700 patent/US10513478B2/en active Active
- 2017-01-04 EP EP17701208.5A patent/EP3400206B1/en active Active
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