CN107597184B - 一种铁基吡咯烷酮离子液体催化剂的制备方法和应用 - Google Patents
一种铁基吡咯烷酮离子液体催化剂的制备方法和应用 Download PDFInfo
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- CN107597184B CN107597184B CN201710697083.8A CN201710697083A CN107597184B CN 107597184 B CN107597184 B CN 107597184B CN 201710697083 A CN201710697083 A CN 201710697083A CN 107597184 B CN107597184 B CN 107597184B
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- ionic liquid
- iron
- liquid catalyst
- catalyst
- pyrrolidone ionic
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- 239000003054 catalyst Substances 0.000 title claims abstract description 59
- 239000002608 ionic liquid Substances 0.000 title claims description 66
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims description 41
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title claims description 35
- 229910052742 iron Inorganic materials 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims description 52
- -1 pyridine diimine iron compound Chemical class 0.000 claims description 37
- 238000003756 stirring Methods 0.000 claims description 22
- 238000001816 cooling Methods 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910000071 diazene Inorganic materials 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 238000003760 magnetic stirring Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- GRAORJFMGCQWRN-UHFFFAOYSA-N Butyl undecylenate Chemical compound CCCCOC(=O)CCCCCCCCC=C GRAORJFMGCQWRN-UHFFFAOYSA-N 0.000 claims 1
- FXNFFCMITPHEIT-UHFFFAOYSA-N Ethyl 10-undecenoate Chemical compound CCOC(=O)CCCCCCCCC=C FXNFFCMITPHEIT-UHFFFAOYSA-N 0.000 claims 1
- YWSDDOFJTUOVMX-VAWYXSNFSA-N Methyl (E)-2-dodecenoate Chemical compound CCCCCCCCC\C=C\C(=O)OC YWSDDOFJTUOVMX-VAWYXSNFSA-N 0.000 claims 1
- SHCSFZHSNSGTOP-UHFFFAOYSA-N Methyl 4-pentenoate Chemical compound COC(=O)CCC=C SHCSFZHSNSGTOP-UHFFFAOYSA-N 0.000 claims 1
- FTJATNSAFIFEDU-UHFFFAOYSA-N ethyl hept-6-enoate Chemical compound CCOC(=O)CCCCC=C FTJATNSAFIFEDU-UHFFFAOYSA-N 0.000 claims 1
- CRHITZQXHNFRAZ-FPLPWBNLSA-N methyl (z)-dec-4-enoate Chemical compound CCCCC\C=C/CCC(=O)OC CRHITZQXHNFRAZ-FPLPWBNLSA-N 0.000 claims 1
- RCMPWMPPJYBDKR-UHFFFAOYSA-N methyl hept-6-enoate Chemical compound COC(=O)CCCCC=C RCMPWMPPJYBDKR-UHFFFAOYSA-N 0.000 claims 1
- ASKDFGVMJZMYEM-UHFFFAOYSA-N methyl hex-5-enoate Chemical compound COC(=O)CCCC=C ASKDFGVMJZMYEM-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 29
- 150000001336 alkenes Chemical class 0.000 description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 10
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 150000002506 iron compounds Chemical class 0.000 description 8
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 6
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 6
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 6
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 5
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N levobunolol Chemical compound O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C IXHBTMCLRNMKHZ-LBPRGKRZSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HDMQOTMYJDPYOW-UHFFFAOYSA-N N1C(CCC1)=O.[Fe] Chemical compound N1C(CCC1)=O.[Fe] HDMQOTMYJDPYOW-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VOLSNBKYZVQSNK-UHFFFAOYSA-N dimethoxy(tetradecyl)silane Chemical compound C(CCCCCCCCCCCCC)[SiH](OC)OC VOLSNBKYZVQSNK-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- VRINOTYEGADLMW-UHFFFAOYSA-N heptyl(trimethoxy)silane Chemical compound CCCCCCC[Si](OC)(OC)OC VRINOTYEGADLMW-UHFFFAOYSA-N 0.000 description 1
- RSKGMYDENCAJEN-UHFFFAOYSA-N hexadecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OC)(OC)OC RSKGMYDENCAJEN-UHFFFAOYSA-N 0.000 description 1
- CZWLNMOIEMTDJY-UHFFFAOYSA-N hexyl(trimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)OC CZWLNMOIEMTDJY-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- IBOFHQZUWNBWNJ-UHFFFAOYSA-N iron;pyridine-2,3-diimine Chemical class [Fe].N=C1C=CC=NC1=N IBOFHQZUWNBWNJ-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 description 1
- PNVQXNRVDYKIKF-UHFFFAOYSA-N trimethoxy-[2-(4-methylphenyl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCC1=CC=C(C)C=C1 PNVQXNRVDYKIKF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- Y02P20/584—Recycling of catalysts
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- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
重复次数 | 烯烃转化率/% | β-加成产物收率/% |
1 | 98.5 | 96.5 |
2 | 96.5 | 95.3 |
3 | 97.5 | 94.5 |
4 | 95.0 | 92.6 |
5 | 94.5 | 93.2 |
Claims (6)
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CN201710697083.8A CN107597184B (zh) | 2017-08-15 | 2017-08-15 | 一种铁基吡咯烷酮离子液体催化剂的制备方法和应用 |
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CN201710697083.8A CN107597184B (zh) | 2017-08-15 | 2017-08-15 | 一种铁基吡咯烷酮离子液体催化剂的制备方法和应用 |
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CN107597184A CN107597184A (zh) | 2018-01-19 |
CN107597184B true CN107597184B (zh) | 2019-12-06 |
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Families Citing this family (2)
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CN113600237B (zh) * | 2021-08-27 | 2023-04-18 | 河北美邦工程科技股份有限公司 | 一种用于催化乙炔氢氯化反应的聚离子液体催化剂 |
CN113788775B (zh) * | 2021-09-03 | 2023-04-07 | 南昌大学 | 磺酸功能化的吡咯烷酮离子液体催化剂及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4101534B2 (ja) * | 2002-03-04 | 2008-06-18 | 丸善石油化学株式会社 | 第8族金属錯体触媒およびこれを利用するアルデヒドの製造方法 |
CN101850269A (zh) * | 2010-05-27 | 2010-10-06 | 杭州师范大学 | 烯烃硅氢加成铂催化剂的促进剂、其制备方法及其应用 |
CN104119371A (zh) * | 2014-03-26 | 2014-10-29 | 杭州师范大学 | 一种烯烃硅氢加成反应的方法 |
CN104324751A (zh) * | 2014-08-18 | 2015-02-04 | 杭州师范大学 | 一种用于烯烃硅氢加成反应的催化剂、其制备方法及采用该催化剂的烯烃硅氢加成反应 |
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2017
- 2017-08-15 CN CN201710697083.8A patent/CN107597184B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4101534B2 (ja) * | 2002-03-04 | 2008-06-18 | 丸善石油化学株式会社 | 第8族金属錯体触媒およびこれを利用するアルデヒドの製造方法 |
CN101850269A (zh) * | 2010-05-27 | 2010-10-06 | 杭州师范大学 | 烯烃硅氢加成铂催化剂的促进剂、其制备方法及其应用 |
CN104119371A (zh) * | 2014-03-26 | 2014-10-29 | 杭州师范大学 | 一种烯烃硅氢加成反应的方法 |
CN104324751A (zh) * | 2014-08-18 | 2015-02-04 | 杭州师范大学 | 一种用于烯烃硅氢加成反应的催化剂、其制备方法及采用该催化剂的烯烃硅氢加成反应 |
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