CN113522357A - 一种离子液体催化剂及其制备方法与应用 - Google Patents
一种离子液体催化剂及其制备方法与应用 Download PDFInfo
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- CN113522357A CN113522357A CN202110960431.2A CN202110960431A CN113522357A CN 113522357 A CN113522357 A CN 113522357A CN 202110960431 A CN202110960431 A CN 202110960431A CN 113522357 A CN113522357 A CN 113522357A
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- Prior art keywords
- ionic liquid
- dicyclopentadiene
- ethylene glycol
- reaction
- meth
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- 239000003054 catalyst Substances 0.000 title claims abstract description 82
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- JMVUBVFMLWTPDW-UHFFFAOYSA-N 3-ethyl-1h-imidazol-3-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CC[N+]=1C=CNC=1 JMVUBVFMLWTPDW-UHFFFAOYSA-N 0.000 claims abstract description 29
- UJJCJWRYKMTSNM-UHFFFAOYSA-N 1,3-dimethylimidazolidin-2-one;sulfuric acid Chemical compound OS(O)(=O)=O.CN1CCN(C)C1=O UJJCJWRYKMTSNM-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000002156 mixing Methods 0.000 claims abstract description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 127
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 77
- 238000006243 chemical reaction Methods 0.000 claims description 49
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 29
- 238000005886 esterification reaction Methods 0.000 claims description 29
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- 238000010438 heat treatment Methods 0.000 claims description 25
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- 239000000463 material Substances 0.000 claims description 21
- ZFARPPONQWFWLM-UHFFFAOYSA-N 5-(2-cyclopenta-2,4-dien-1-yloxyethoxy)cyclopenta-1,3-diene Chemical compound C1(C=CC=C1)OCCOC1C=CC=C1 ZFARPPONQWFWLM-UHFFFAOYSA-N 0.000 claims description 19
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- IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- TVEOIQKGZSIMNG-UHFFFAOYSA-N hydron;1-methyl-1h-imidazol-1-ium;sulfate Chemical compound OS([O-])(=O)=O.C[NH+]1C=CN=C1 TVEOIQKGZSIMNG-UHFFFAOYSA-N 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 238000001308 synthesis method Methods 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- CPQUDUZKHJNUHS-UHFFFAOYSA-N 1-[2-(cyclopenten-1-yloxy)ethoxy]cyclopentene Chemical compound C=1CCCC=1OCCOC1=CCCC1 CPQUDUZKHJNUHS-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
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Images
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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
-
- 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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- 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
- B01J2231/49—Esterification or transesterification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
序号 | 产率 | 纯度 |
1 | 92.5% | 99.53% |
2 | 92.3% | 99.50% |
3 | 92.3% | 99.50% |
4 | 92.2% | 99.49% |
5 | 91.9% | 99.43% |
6 | 91.6% | 99.32% |
7 | 91.3% | 99.30% |
8 | 91.3% | 99.28% |
9 | 90.8% | 99.20% |
10 | 90.5% | 98.89% |
Claims (10)
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114177941A (zh) * | 2021-12-16 | 2022-03-15 | 太仓运通新材料科技有限公司 | 一种酯化催化剂及其制备方法 |
CN114213252A (zh) * | 2021-12-30 | 2022-03-22 | 广东希必达新材料科技有限公司 | 一种连续制备双环戊烯基丙烯酸酯的方法 |
CN114213252B (zh) * | 2021-12-30 | 2024-05-31 | 广东希必达新材料科技有限公司 | 一种连续制备双环戊烯基丙烯酸酯的方法 |
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US4097677A (en) * | 1976-07-07 | 1978-06-27 | Rohm And Haas Company | Unsaturated esters of glycol monodicyclopentenyl ethers |
WO2008108221A1 (ja) * | 2007-03-06 | 2008-09-12 | Nippon Steel Chemical Co., Ltd. | 環状グアニジンイオン液体 |
CN101837302A (zh) * | 2010-05-20 | 2010-09-22 | 华东师范大学 | 一种手性咪唑啉酮类离子液体催化剂的制备方法 |
CN102617414A (zh) * | 2012-03-02 | 2012-08-01 | 苏州氟特电池材料有限公司 | 含氯磺酰/磷酰亚胺碱金属盐和含氟磺酰/磷酰亚胺碱金属盐的制备方法 |
CN106045849A (zh) * | 2016-06-02 | 2016-10-26 | 山东瑞博龙化工科技股份有限公司 | (甲基)丙烯酸双环戊二烯基氧乙酯的合成方法 |
CN109206625A (zh) * | 2017-06-30 | 2019-01-15 | 翁秋梅 | 一种物理分相超分子动态聚合物及其应用 |
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2021
- 2021-08-20 CN CN202110960431.2A patent/CN113522357B/zh active Active
Patent Citations (6)
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US4097677A (en) * | 1976-07-07 | 1978-06-27 | Rohm And Haas Company | Unsaturated esters of glycol monodicyclopentenyl ethers |
WO2008108221A1 (ja) * | 2007-03-06 | 2008-09-12 | Nippon Steel Chemical Co., Ltd. | 環状グアニジンイオン液体 |
CN101837302A (zh) * | 2010-05-20 | 2010-09-22 | 华东师范大学 | 一种手性咪唑啉酮类离子液体催化剂的制备方法 |
CN102617414A (zh) * | 2012-03-02 | 2012-08-01 | 苏州氟特电池材料有限公司 | 含氯磺酰/磷酰亚胺碱金属盐和含氟磺酰/磷酰亚胺碱金属盐的制备方法 |
CN106045849A (zh) * | 2016-06-02 | 2016-10-26 | 山东瑞博龙化工科技股份有限公司 | (甲基)丙烯酸双环戊二烯基氧乙酯的合成方法 |
CN109206625A (zh) * | 2017-06-30 | 2019-01-15 | 翁秋梅 | 一种物理分相超分子动态聚合物及其应用 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN114177941A (zh) * | 2021-12-16 | 2022-03-15 | 太仓运通新材料科技有限公司 | 一种酯化催化剂及其制备方法 |
CN114213252A (zh) * | 2021-12-30 | 2022-03-22 | 广东希必达新材料科技有限公司 | 一种连续制备双环戊烯基丙烯酸酯的方法 |
CN114213252B (zh) * | 2021-12-30 | 2024-05-31 | 广东希必达新材料科技有限公司 | 一种连续制备双环戊烯基丙烯酸酯的方法 |
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