CN107226903A - 一种合成手性二醇的双功能、双金属催化剂及其应用 - Google Patents
一种合成手性二醇的双功能、双金属催化剂及其应用 Download PDFInfo
- Publication number
- CN107226903A CN107226903A CN201610983096.7A CN201610983096A CN107226903A CN 107226903 A CN107226903 A CN 107226903A CN 201610983096 A CN201610983096 A CN 201610983096A CN 107226903 A CN107226903 A CN 107226903A
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- Prior art keywords
- oxygen
- catalyst
- difunctional
- synthesis
- makrolon
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Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 41
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 22
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 22
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 42
- 239000004425 Makrolon Substances 0.000 claims abstract description 35
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 23
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- -1 diol compound Chemical class 0.000 claims abstract description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004417 polycarbonate Substances 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 239000002262 Schiff base Substances 0.000 claims abstract description 4
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 4
- 239000004305 biphenyl Substances 0.000 claims abstract description 4
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 4
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- PRRSFMGODMUPJN-CABZTGNLSA-N 2-fluoro-4-[(2r,3s)-5,5,5-trifluoro-3-(3-fluoro-4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C1([C@@H](CC(F)(F)F)[C@@H](C)C=2C=C(F)C(O)=CC=2)=CC=C(O)C(F)=C1 PRRSFMGODMUPJN-CABZTGNLSA-N 0.000 claims description 6
- HJSSBIMVTMYKPD-UHFFFAOYSA-N 3,5-difluorophenol Chemical class OC1=CC(F)=CC(F)=C1 HJSSBIMVTMYKPD-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- SGXJIMGHOCRJJW-UHFFFAOYSA-N [O].[N+](=O)([O-])C1=C(C=CC=C1)O Chemical compound [O].[N+](=O)([O-])C1=C(C=CC=C1)O SGXJIMGHOCRJJW-UHFFFAOYSA-N 0.000 claims description 6
- DUZNLCNPJVJPHK-UHFFFAOYSA-N [O].[N+](=O)([O-])C1=CC=C(C=C1)O Chemical compound [O].[N+](=O)([O-])C1=CC=C(C=C1)O DUZNLCNPJVJPHK-UHFFFAOYSA-N 0.000 claims description 6
- LCZSFVMKKSGELK-UHFFFAOYSA-N [O].[N+](=O)([O-])C=1C=C(C=C(C=1)[N+](=O)[O-])O Chemical compound [O].[N+](=O)([O-])C=1C=C(C=C(C=1)[N+](=O)[O-])O LCZSFVMKKSGELK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 229910001914 chlorine tetroxide Inorganic materials 0.000 claims description 6
- 229950009730 pentafluranol Drugs 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 6
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- LWFZZYSDYXSRSX-UHFFFAOYSA-N [O].[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])O Chemical compound [O].[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])O LWFZZYSDYXSRSX-UHFFFAOYSA-N 0.000 claims description 4
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 claims description 3
- INKDAKMSOSCDGL-UHFFFAOYSA-N [O].OC1=CC=CC=C1 Chemical compound [O].OC1=CC=CC=C1 INKDAKMSOSCDGL-UHFFFAOYSA-N 0.000 claims description 3
- PMUMDPQYCZXYFX-UHFFFAOYSA-N [O].[N+](=O)([O-])C=1C=C(C=CC=1)O Chemical compound [O].[N+](=O)([O-])C=1C=C(C=CC=1)O PMUMDPQYCZXYFX-UHFFFAOYSA-N 0.000 claims description 3
- 125000005466 alkylenyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000004651 carbonic acid esters Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- 230000004913 activation Effects 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 150000004714 phosphonium salts Chemical group 0.000 abstract description 2
- 239000004593 Epoxy Substances 0.000 description 10
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000012648 alternating copolymerization Methods 0.000 description 4
- WVEPPXXXZXVMAR-UHFFFAOYSA-N formic acid;toluene Chemical compound OC=O.CC1=CC=CC=C1 WVEPPXXXZXVMAR-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 235000013844 butane Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- PQXKWPLDPFFDJP-ZXZARUISSA-N (2r,3s)-2,3-dimethyloxirane Chemical compound C[C@H]1O[C@H]1C PQXKWPLDPFFDJP-ZXZARUISSA-N 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical class [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SFLZKCRQLOAHLV-UHFFFAOYSA-N [O].FC(C=1C=C(C=C(C=1)C(F)(F)F)O)(F)F Chemical compound [O].FC(C=1C=C(C=C(C=1)C(F)(F)F)O)(F)F SFLZKCRQLOAHLV-UHFFFAOYSA-N 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GCNLQHANGFOQKY-UHFFFAOYSA-N [C+4].[O-2].[O-2].[Ti+4] Chemical compound [C+4].[O-2].[O-2].[Ti+4] GCNLQHANGFOQKY-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004177 carbon cycle Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UQXKXGWGFRWILX-UHFFFAOYSA-N ethylene glycol dinitrate Chemical compound O=N(=O)OCCON(=O)=O UQXKXGWGFRWILX-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
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CN201610983096.7A CN107226903B (zh) | 2016-11-09 | 2016-11-09 | 一种合成手性二醇的双功能、双金属催化剂及其应用 |
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CN107226903A true CN107226903A (zh) | 2017-10-03 |
CN107226903B CN107226903B (zh) | 2019-08-23 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114163627A (zh) * | 2021-11-09 | 2022-03-11 | 大连理工大学 | 一类双功能双金属催化剂及其应用 |
CN114479055A (zh) * | 2022-02-28 | 2022-05-13 | 大连理工大学 | 一种用于环氧烷烃、环状酸酐和二氧化碳共聚的双功能催化剂和应用方法 |
WO2023134011A1 (zh) * | 2022-01-17 | 2023-07-20 | 中国科学院长春应用化学研究所 | 一种双核席夫碱钴配合物及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1560111A (zh) * | 2004-02-27 | 2005-01-05 | 大连理工大学 | 一种高分子量完全交替结构聚碳酸酯的制备方法 |
CN101020747A (zh) * | 2007-03-21 | 2007-08-22 | 大连理工大学 | 用于合成聚碳酸酯的双功能催化剂 |
CN103102480A (zh) * | 2013-01-24 | 2013-05-15 | 大连理工大学 | 用于合成立构规整性聚碳酸酯的双金属催化剂 |
CN103170365A (zh) * | 2013-01-29 | 2013-06-26 | 沈阳金久奇科技有限公司 | 一种高活性双功能催化剂及其制备方法和应用 |
-
2016
- 2016-11-09 CN CN201610983096.7A patent/CN107226903B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1560111A (zh) * | 2004-02-27 | 2005-01-05 | 大连理工大学 | 一种高分子量完全交替结构聚碳酸酯的制备方法 |
CN101020747A (zh) * | 2007-03-21 | 2007-08-22 | 大连理工大学 | 用于合成聚碳酸酯的双功能催化剂 |
CN103102480A (zh) * | 2013-01-24 | 2013-05-15 | 大连理工大学 | 用于合成立构规整性聚碳酸酯的双金属催化剂 |
CN103170365A (zh) * | 2013-01-29 | 2013-06-26 | 沈阳金久奇科技有限公司 | 一种高活性双功能催化剂及其制备方法和应用 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114163627A (zh) * | 2021-11-09 | 2022-03-11 | 大连理工大学 | 一类双功能双金属催化剂及其应用 |
WO2023134011A1 (zh) * | 2022-01-17 | 2023-07-20 | 中国科学院长春应用化学研究所 | 一种双核席夫碱钴配合物及其制备方法和应用 |
CN114479055A (zh) * | 2022-02-28 | 2022-05-13 | 大连理工大学 | 一种用于环氧烷烃、环状酸酐和二氧化碳共聚的双功能催化剂和应用方法 |
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