CN117050218A - 含有Nd-MIL-103的稀土催化剂以及基于该催化剂的制备顺式聚丁二烯的方法 - Google Patents
含有Nd-MIL-103的稀土催化剂以及基于该催化剂的制备顺式聚丁二烯的方法 Download PDFInfo
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- CN117050218A CN117050218A CN202311309214.2A CN202311309214A CN117050218A CN 117050218 A CN117050218 A CN 117050218A CN 202311309214 A CN202311309214 A CN 202311309214A CN 117050218 A CN117050218 A CN 117050218A
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- Prior art keywords
- mil
- rare earth
- earth catalyst
- polybutadiene
- catalyst containing
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- 239000003054 catalyst Substances 0.000 title claims abstract description 77
- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract description 59
- 150000002910 rare earth metals Chemical class 0.000 title claims abstract description 57
- 229920002857 polybutadiene Polymers 0.000 title claims abstract description 54
- 239000005062 Polybutadiene Substances 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 18
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 88
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 25
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 150000001298 alcohols Chemical class 0.000 claims abstract description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 36
- 229910052779 Neodymium Inorganic materials 0.000 claims description 23
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 230000032683 aging Effects 0.000 claims description 8
- -1 alcohol compound Chemical class 0.000 claims description 8
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical group CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 238000009826 distribution Methods 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 74
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 33
- 238000003756 stirring Methods 0.000 description 30
- 239000002244 precipitate Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000002608 ionic liquid Substances 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 16
- SATWKVZGMWCXOJ-UHFFFAOYSA-N 4-[3,5-bis(4-carboxyphenyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C=2C=CC(=CC=2)C(O)=O)=CC(C=2C=CC(=CC=2)C(O)=O)=C1 SATWKVZGMWCXOJ-UHFFFAOYSA-N 0.000 description 11
- 230000009471 action Effects 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 11
- 239000011259 mixed solution Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 238000011049 filling Methods 0.000 description 10
- 239000001632 sodium acetate Substances 0.000 description 10
- 235000017281 sodium acetate Nutrition 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 238000001291 vacuum drying Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000013241 lanthanide-based metal–organic framework Substances 0.000 description 4
- 239000012621 metal-organic framework Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- 238000007210 heterogeneous catalysis Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000863902 Odilia Species 0.000 description 1
- 235000011449 Rosa Nutrition 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- LUTCIFPQNFPSIZ-UHFFFAOYSA-K n,n-diethylethanamine;trichloroalumane;hydrochloride Chemical compound [Al+3].Cl.[Cl-].[Cl-].[Cl-].CCN(CC)CC LUTCIFPQNFPSIZ-UHFFFAOYSA-K 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/06—Butadiene
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
Description
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CN202311309214.2A CN117050218B (zh) | 2023-10-11 | 2023-10-11 | 含有Nd-MIL-103的稀土催化剂以及基于该催化剂的制备顺式聚丁二烯的方法 |
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CN117050218A true CN117050218A (zh) | 2023-11-14 |
CN117050218B CN117050218B (zh) | 2024-02-13 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117264103A (zh) * | 2023-11-21 | 2023-12-22 | 传化智联股份有限公司 | 一种含有新癸酸钕的稀土催化剂及基于该催化剂的聚丁二烯的制备方法 |
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CN113801063A (zh) * | 2021-08-27 | 2021-12-17 | 浙江工业大学 | 1-(4-羧过氧苄基)-3-甲基咪唑四氯化铝盐或铁盐及其制备和应用 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117264103A (zh) * | 2023-11-21 | 2023-12-22 | 传化智联股份有限公司 | 一种含有新癸酸钕的稀土催化剂及基于该催化剂的聚丁二烯的制备方法 |
CN117264103B (zh) * | 2023-11-21 | 2024-02-20 | 传化智联股份有限公司 | 一种含有新癸酸钕的稀土催化剂及基于该催化剂的聚丁二烯的制备方法 |
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Address after: 311215 Xiaoshan economic and Technological Development Zone, Zhejiang, Hangzhou Applicant after: TRANSFAR ZHILIAN CO.,LTD. Applicant after: Zhejiang Chuanhua Synthetic Materials Co.,Ltd. Applicant after: JIANG University OF TECHNOLOGY Applicant after: Zhejiang ChuanHua functional new material Co.,Ltd. Applicant after: HANGZHOU TRANSFAR FINE CHEMICAL CO.,LTD. Address before: 311215 Xiaoshan economic and Technological Development Zone, Zhejiang, Hangzhou Applicant before: TRANSFAR ZHILIAN CO.,LTD. Applicant before: ZHEJIANG TRANSFAR SYNTHETIC MATERIALS Co.,Ltd. Applicant before: JIANG University OF TECHNOLOGY Applicant before: Zhejiang ChuanHua functional new material Co.,Ltd. Applicant before: HANGZHOU TRANSFAR FINE CHEMICAL CO.,LTD. |
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