CN109364921A - 一种用于常温常压催化Suzuki偶联反应的催化剂 - Google Patents
一种用于常温常压催化Suzuki偶联反应的催化剂 Download PDFInfo
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- CN109364921A CN109364921A CN201811287714.XA CN201811287714A CN109364921A CN 109364921 A CN109364921 A CN 109364921A CN 201811287714 A CN201811287714 A CN 201811287714A CN 109364921 A CN109364921 A CN 109364921A
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- catalyst
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- suzuki coupling
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- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 67
- 239000003054 catalyst Substances 0.000 title claims abstract description 61
- 238000006069 Suzuki reaction reaction Methods 0.000 title claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 63
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 60
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 15
- 229910000420 cerium oxide Inorganic materials 0.000 claims abstract description 6
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 14
- 239000002077 nanosphere Substances 0.000 claims description 12
- 239000004793 Polystyrene Substances 0.000 claims description 11
- 229920002223 polystyrene Polymers 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 8
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229910052684 Cerium Inorganic materials 0.000 claims description 6
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
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- 229920003081 Povidone K 30 Polymers 0.000 claims description 2
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- 229910003445 palladium oxide Inorganic materials 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims 1
- 150000003797 alkaloid derivatives Chemical class 0.000 claims 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 abstract description 9
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
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- 239000011943 nanocatalyst Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
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- 230000008878 coupling Effects 0.000 description 20
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- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 17
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- 239000008367 deionised water Substances 0.000 description 13
- 229910021641 deionized water Inorganic materials 0.000 description 13
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- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 4
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 4
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 4
- VLCPISYURGTGLP-UHFFFAOYSA-N 1-iodo-3-methylbenzene Chemical compound CC1=CC=CC(I)=C1 VLCPISYURGTGLP-UHFFFAOYSA-N 0.000 description 4
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 description 4
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical group C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 4
- NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 4
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 150000008424 iodobenzenes Chemical class 0.000 description 4
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007210 heterogeneous catalysis Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 description 2
- BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000004768 bromobenzenes Chemical class 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- 229920002554 vinyl polymer Polymers 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/63—Platinum group metals with rare earths or actinides
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (7)
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110433825A (zh) * | 2019-07-30 | 2019-11-12 | 北京氦舶科技有限责任公司 | 一种单原子钯基催化剂及其制备方法和应用 |
CN110681379A (zh) * | 2019-09-03 | 2020-01-14 | 北京氦舶科技有限责任公司 | 单原子钯催化剂及其制备和在Suzuki反应中的应用 |
CN113634258A (zh) * | 2021-09-16 | 2021-11-12 | 浙江理工大学 | 一种用于光催化还原二氧化碳生成乙烯的催化剂及其制备方法 |
CN114082447A (zh) * | 2021-11-17 | 2022-02-25 | 甘肃警察职业学院 | 一种咪唑类离子液体单原子催化剂的制备方法及其应用 |
Citations (4)
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EP1010464B1 (en) * | 1998-12-17 | 2004-09-22 | Agency Of Industrial Science And Technology | Palladium ceria supported catalyst and process for the synthesis of methanol |
CN103599776A (zh) * | 2013-11-21 | 2014-02-26 | 福州大学 | 一种Pd/CeO2可见光光催化剂及其制备方法和应用 |
CN105233877A (zh) * | 2014-06-23 | 2016-01-13 | 绍兴文理学院 | 一种多孔海绵状壳聚糖负载钯催化材料的制备方法 |
CN108017083A (zh) * | 2018-02-08 | 2018-05-11 | 济南大学 | 一种由空心颗粒构筑的CeO2多孔纳米簇及其制备方法 |
-
2018
- 2018-10-31 CN CN201811287714.XA patent/CN109364921B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1010464B1 (en) * | 1998-12-17 | 2004-09-22 | Agency Of Industrial Science And Technology | Palladium ceria supported catalyst and process for the synthesis of methanol |
CN103599776A (zh) * | 2013-11-21 | 2014-02-26 | 福州大学 | 一种Pd/CeO2可见光光催化剂及其制备方法和应用 |
CN105233877A (zh) * | 2014-06-23 | 2016-01-13 | 绍兴文理学院 | 一种多孔海绵状壳聚糖负载钯催化材料的制备方法 |
CN108017083A (zh) * | 2018-02-08 | 2018-05-11 | 济南大学 | 一种由空心颗粒构筑的CeO2多孔纳米簇及其制备方法 |
Non-Patent Citations (3)
Title |
---|
FRANCESCO AMOROSO ET AL.: "An efficient and reusable catalyst based on Pd/CeO2 for the room temperature aerobic Suzuki-Miyaura reaction in water/ethanol", 《JOURNAL OF MOLECULAR CATALYSIS A:CHEMICAL》 * |
JUN ZHANG ET AL.: "Creation of three-dimensionally ordered macroporous Au/CeO2 catalysts with controlled pore sizes and their enhanced catalytic performance for formaldehyde oxidation", 《APPLIED CATALYSIS B:ENVIRONMENTAL》 * |
XIAOYAN ZHANG ET AL.: "C-C Coupling on Single-Atom-Based Heterogeneous Catalyst", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110433825A (zh) * | 2019-07-30 | 2019-11-12 | 北京氦舶科技有限责任公司 | 一种单原子钯基催化剂及其制备方法和应用 |
CN110681379A (zh) * | 2019-09-03 | 2020-01-14 | 北京氦舶科技有限责任公司 | 单原子钯催化剂及其制备和在Suzuki反应中的应用 |
CN113634258A (zh) * | 2021-09-16 | 2021-11-12 | 浙江理工大学 | 一种用于光催化还原二氧化碳生成乙烯的催化剂及其制备方法 |
CN113634258B (zh) * | 2021-09-16 | 2023-01-03 | 浙江理工大学 | 一种用于光催化还原二氧化碳生成乙烯的催化剂及其制备方法 |
CN114082447A (zh) * | 2021-11-17 | 2022-02-25 | 甘肃警察职业学院 | 一种咪唑类离子液体单原子催化剂的制备方法及其应用 |
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CP02 | Change in the address of a patent holder |
Address after: 201204 first floor, No. 30, Lane 676, Wuxing Road, Pudong New Area, Shanghai Patentee after: Xiyuan environmental protection (Shanghai) Co.,Ltd. Address before: 200120 1st floor, No.8 Lane 676, Wuxing Road, Pudong New Area, Shanghai Patentee before: Xiyuan environmental protection (Shanghai) Co.,Ltd. |