CN110218302A - 一种基于1,3,5-苯三甲醛的共轭微孔聚合物及其制备方法 - Google Patents
一种基于1,3,5-苯三甲醛的共轭微孔聚合物及其制备方法 Download PDFInfo
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- CN110218302A CN110218302A CN201910635689.8A CN201910635689A CN110218302A CN 110218302 A CN110218302 A CN 110218302A CN 201910635689 A CN201910635689 A CN 201910635689A CN 110218302 A CN110218302 A CN 110218302A
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- microporous polymer
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- benzene
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- 229920000642 polymer Polymers 0.000 title claims abstract description 64
- 230000021615 conjugation Effects 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006482 condensation reaction Methods 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 17
- 230000008569 process Effects 0.000 claims abstract description 6
- 238000005815 base catalysis Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 238000000944 Soxhlet extraction Methods 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- LASVAZQZFYZNPK-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5-triazine Chemical compound CC1=NC(C)=NC(C)=N1 LASVAZQZFYZNPK-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 7
- 239000012065 filter cake Substances 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 9
- 238000010521 absorption reaction Methods 0.000 abstract description 7
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 7
- 229910000510 noble metal Inorganic materials 0.000 abstract description 7
- 239000011148 porous material Substances 0.000 abstract description 7
- 230000002776 aggregation Effects 0.000 abstract description 5
- 238000004220 aggregation Methods 0.000 abstract description 5
- 239000002245 particle Substances 0.000 abstract description 5
- 238000001308 synthesis method Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000013310 covalent-organic framework Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007210 heterogeneous catalysis Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002957 persistent organic pollutant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000013317 conjugated microporous polymer Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- -1 halogenated aryl hydrocarbon Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000013315 hypercross-linked polymer Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000013316 polymer of intrinsic microporosity Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000010792 warming Methods 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/18—Definition of the polymer structure conjugated
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/59—Stability
- C08G2261/592—Stability against heat
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
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CN201910635689.8A CN110218302B (zh) | 2019-07-15 | 2019-07-15 | 一种基于1,3,5-苯三甲醛的共轭微孔聚合物及其制备方法 |
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CN201910635689.8A CN110218302B (zh) | 2019-07-15 | 2019-07-15 | 一种基于1,3,5-苯三甲醛的共轭微孔聚合物及其制备方法 |
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CN110218302B CN110218302B (zh) | 2021-08-20 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111057221A (zh) * | 2019-12-26 | 2020-04-24 | 上海交通大学 | 一种碳碳双键连接的有机框架超长纳米纤维材料及其制备方法 |
CN112898469A (zh) * | 2021-01-25 | 2021-06-04 | 三明学院 | 一种具有微孔结构的全芳基簇发光聚合物及其制备方法 |
CN113845646A (zh) * | 2021-10-20 | 2021-12-28 | 浙江时间新材料有限公司 | 一种基于嘧啶和氰基的双功能化共轭微孔聚合物及其制备方法和应用 |
CN114181378A (zh) * | 2021-11-25 | 2022-03-15 | 上海科技大学 | 一种三芳基硼类共轭聚合物多孔材料及其制备方法和用途 |
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CN103282984A (zh) * | 2010-11-26 | 2013-09-04 | 巴斯夫欧洲公司 | 制备含氮的多孔碳质材料的方法 |
CN106084217A (zh) * | 2016-05-27 | 2016-11-09 | 山西师范大学 | 一种三嗪基多孔聚合物材料、Ag/三嗪基多孔聚合物催化剂及其将二氧化碳转化为炔酸的应用 |
CN108892759A (zh) * | 2018-06-07 | 2018-11-27 | 台州学院 | 一种共轭微孔聚合物及其制备方法 |
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2019
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CN103282984A (zh) * | 2010-11-26 | 2013-09-04 | 巴斯夫欧洲公司 | 制备含氮的多孔碳质材料的方法 |
CN106084217A (zh) * | 2016-05-27 | 2016-11-09 | 山西师范大学 | 一种三嗪基多孔聚合物材料、Ag/三嗪基多孔聚合物催化剂及其将二氧化碳转化为炔酸的应用 |
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Non-Patent Citations (3)
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LEI LIU ET AL.: "Microporous polymelamine network for highly selective CO2 adsorption", 《POLYMER》 * |
NING XU,ET AL.: "Continuous detection of HCl and NH3 gases with a high-performance fluorescent polymer sensor", 《NEW J. CHEM》 * |
YOMNA H. ABDELMOATY ET AL.: "Nitrogen-Rich Porous Polymers for Carbon Dioxide and Iodine Sequestration for Environmental Remediation", 《ACS APPL. MATER. INTERFACES》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111057221A (zh) * | 2019-12-26 | 2020-04-24 | 上海交通大学 | 一种碳碳双键连接的有机框架超长纳米纤维材料及其制备方法 |
CN112898469A (zh) * | 2021-01-25 | 2021-06-04 | 三明学院 | 一种具有微孔结构的全芳基簇发光聚合物及其制备方法 |
CN113845646A (zh) * | 2021-10-20 | 2021-12-28 | 浙江时间新材料有限公司 | 一种基于嘧啶和氰基的双功能化共轭微孔聚合物及其制备方法和应用 |
CN114181378A (zh) * | 2021-11-25 | 2022-03-15 | 上海科技大学 | 一种三芳基硼类共轭聚合物多孔材料及其制备方法和用途 |
CN114181378B (zh) * | 2021-11-25 | 2023-06-16 | 上海科技大学 | 一种三芳基硼类共轭聚合物多孔材料及其制备方法和用途 |
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Application publication date: 20190910 Assignee: Sanmen Zhongliang Pharmacy Co.,Ltd. Assignor: TAIZHOU University Contract record no.: X2024330000659 Denomination of invention: A Conjugated Microporous Polymer Based on 1,3,5-Benzenetrialdehyde and Its Preparation Method Granted publication date: 20210820 License type: Common License Record date: 20240927 Application publication date: 20190910 Assignee: Sanmen County Dexin Pharmacy Co.,Ltd. Assignor: TAIZHOU University Contract record no.: X2024330000658 Denomination of invention: A Conjugated Microporous Polymer Based on 1,3,5-Benzenetrialdehyde and Its Preparation Method Granted publication date: 20210820 License type: Common License Record date: 20240927 |