CN110327974A - 一种交联降冰片烯共聚物/炭黑三维网络负载钯纳米催化剂及其制备方法与应用 - Google Patents
一种交联降冰片烯共聚物/炭黑三维网络负载钯纳米催化剂及其制备方法与应用 Download PDFInfo
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- CN110327974A CN110327974A CN201910684771.XA CN201910684771A CN110327974A CN 110327974 A CN110327974 A CN 110327974A CN 201910684771 A CN201910684771 A CN 201910684771A CN 110327974 A CN110327974 A CN 110327974A
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- Prior art keywords
- carbon black
- dimensional network
- norbornene copolymer
- catalyst
- crosslinking
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 134
- 229920001577 copolymer Polymers 0.000 title claims abstract description 66
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 54
- 239000006229 carbon black Substances 0.000 title claims abstract description 50
- 238000004132 cross linking Methods 0.000 title claims abstract description 32
- 239000011943 nanocatalyst Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 15
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 239000006185 dispersion Substances 0.000 claims description 11
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 11
- 239000012279 sodium borohydride Substances 0.000 claims description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 239000012295 chemical reaction liquid Substances 0.000 claims description 10
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 9
- 229920000636 poly(norbornene) polymer Polymers 0.000 claims description 9
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229920002521 macromolecule Polymers 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000011984 grubbs catalyst Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000007789 gas Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 9
- 239000002184 metal Substances 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 8
- 238000004064 recycling Methods 0.000 abstract description 8
- 239000002105 nanoparticle Substances 0.000 abstract description 7
- 238000011109 contamination Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 7
- 239000012300 argon atmosphere Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000013049 sediment Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- ZQTYQMYDIHMKQB-UHFFFAOYSA-N exo-norborneol Chemical compound C1CC2C(O)CC1C2 ZQTYQMYDIHMKQB-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- VLCPISYURGTGLP-UHFFFAOYSA-N 1-iodo-3-methylbenzene Chemical compound CC1=CC=CC(I)=C1 VLCPISYURGTGLP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 1
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
- -1 3- methyl iodobenzene benzene Chemical compound 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000002082 metal nanoparticle Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/04—Substitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (10)
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CN201910684771.XA CN110327974B (zh) | 2019-07-26 | 2019-07-26 | 一种交联降冰片烯共聚物/炭黑三维网络负载钯纳米催化剂及其制备方法与应用 |
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CN201910684771.XA CN110327974B (zh) | 2019-07-26 | 2019-07-26 | 一种交联降冰片烯共聚物/炭黑三维网络负载钯纳米催化剂及其制备方法与应用 |
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CN110327974B CN110327974B (zh) | 2022-03-15 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110339860A (zh) * | 2019-07-29 | 2019-10-18 | 湖北工程学院 | 交联降冰片烯共聚物复合炭黑三维网络固载铂纳米催化剂及其制备方法和应用 |
WO2023206835A1 (zh) * | 2022-04-28 | 2023-11-02 | 湖北工程学院 | 一种交联降冰片烯共聚物/炭黑三维网络固载双金属铜/金纳米催化剂及其制备方法和应用 |
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KR20020082396A (ko) * | 2001-04-21 | 2002-10-31 | 삼성전자 주식회사 | 아세탈기를 포함하는 포토레지스트용 노르보넨 공중합체,그의 제조방법 및 그를 포함하는 포토레지스트 조성물 |
CN1585781A (zh) * | 2002-07-10 | 2005-02-23 | Lg化学株式会社 | 制备含有酯或乙酰功能基团的降冰片烯基加成聚合物的方法 |
CN103433071A (zh) * | 2013-09-17 | 2013-12-11 | 绍兴文理学院 | Ipn负载钯纳米催化剂及其制备和应用 |
CN104511310A (zh) * | 2015-01-21 | 2015-04-15 | 东华理工大学 | 一种介孔碳负载氮杂环卡宾钯催化剂及制备方法和应用 |
CN105032492A (zh) * | 2015-01-26 | 2015-11-11 | 商丘师范学院 | 多孔网状高聚物包覆磁性纳米粒子负载钯催化剂及其制备方法 |
CN105344380A (zh) * | 2015-12-08 | 2016-02-24 | 镇江市高等专科学校 | 一种金属有机框架/石墨烯负载钯纳米复合催化剂及其制备方法和应用 |
-
2019
- 2019-07-26 CN CN201910684771.XA patent/CN110327974B/zh active Active
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KR20020082396A (ko) * | 2001-04-21 | 2002-10-31 | 삼성전자 주식회사 | 아세탈기를 포함하는 포토레지스트용 노르보넨 공중합체,그의 제조방법 및 그를 포함하는 포토레지스트 조성물 |
CN1585781A (zh) * | 2002-07-10 | 2005-02-23 | Lg化学株式会社 | 制备含有酯或乙酰功能基团的降冰片烯基加成聚合物的方法 |
CN103433071A (zh) * | 2013-09-17 | 2013-12-11 | 绍兴文理学院 | Ipn负载钯纳米催化剂及其制备和应用 |
CN104511310A (zh) * | 2015-01-21 | 2015-04-15 | 东华理工大学 | 一种介孔碳负载氮杂环卡宾钯催化剂及制备方法和应用 |
CN105032492A (zh) * | 2015-01-26 | 2015-11-11 | 商丘师范学院 | 多孔网状高聚物包覆磁性纳米粒子负载钯催化剂及其制备方法 |
CN105344380A (zh) * | 2015-12-08 | 2016-02-24 | 镇江市高等专科学校 | 一种金属有机框架/石墨烯负载钯纳米复合催化剂及其制备方法和应用 |
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ANGELA N等: ""Investigation of activity,stability,and degradation mechanism of surface-supported Pd-PEPPSI complexes for Suzuki-Miyaura coupling"", 《JOURNAL OFMOLECULARCATALYSISA:CHEMICAL》 * |
李景波等: ""负载钯催化剂应用于Suzuki偶联反应的研究进展"", 《宜春学院学报》 * |
邱杨成: ""降冰片烯诱导下的钯催化苯环间位芳基化偶联反应研究"", 《中国优秀硕士论文数据库》 * |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110339860A (zh) * | 2019-07-29 | 2019-10-18 | 湖北工程学院 | 交联降冰片烯共聚物复合炭黑三维网络固载铂纳米催化剂及其制备方法和应用 |
CN110339860B (zh) * | 2019-07-29 | 2022-03-01 | 湖北工程学院 | 交联降冰片烯共聚物复合炭黑三维网络固载铂纳米催化剂及其制备方法和应用 |
WO2023206835A1 (zh) * | 2022-04-28 | 2023-11-02 | 湖北工程学院 | 一种交联降冰片烯共聚物/炭黑三维网络固载双金属铜/金纳米催化剂及其制备方法和应用 |
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