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Cyclopentadiene-N-(2-methylquinoline) titanium benzoic amide coordination compound as well as preparation method and application thereof

A cyclopentadienyl, benzamide titanium technology, applied in chemical instruments and methods, organic chemistry, metallocene and other directions, can solve the problems of difficult structural modification, poor stability, and limiting the practical application of metallocene catalysts

Inactive Publication Date: 2012-04-18
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, metallocenes not only require the presence of a large amount of MAO to show high activity, but also have difficulty in structural modification and poor stability, which limit the practical application of metallocene catalysts to a certain extent.

Method used

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  • Cyclopentadiene-N-(2-methylquinoline) titanium benzoic amide coordination compound as well as preparation method and application thereof
  • Cyclopentadiene-N-(2-methylquinoline) titanium benzoic amide coordination compound as well as preparation method and application thereof
  • Cyclopentadiene-N-(2-methylquinoline) titanium benzoic amide coordination compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0051] Concrete preparation process is as follows:

[0052] 1. The general method of ligand synthesis

[0053] React 2-methyl-8-aminoquinoline with 1 equivalent of 4-substituted benzoic acid, and use 1 / 3 equivalent of triphenyl phosphite as a dehydrating agent, use xylene as a solvent, reflux for 6 hours, and concentrate , basic alumina or silica gel column chromatography, rinse with petroleum ether / ethyl acetate (5:1-10:1), the second effluent component is the product, and the solvent is removed to obtain a white solid N-(2-methyl quinoline) benzoic acid amide.

[0054] Second, the general method of synthesis of titanium complexes

[0055] At room temperature, the tetrahydrofuran solution of N-(2-methylquinoline)-benzoic acid amide was added dropwise to 1 equivalent of KH, and the reaction was stirred for 12 hours to obtain a yellow suspension. At -78°C, 1 equivalent of tetrahydrofuran solution of cyclopentadienyl titanium complex was added dropwise to the above suspension...

Embodiment 1

[0060] Example 1, Preparation of 4-methoxy-N-(2-methylquinoline) benzoic acid amide [ligand 1]

[0061]In 250ml flask, add 2-methyl-8-aminoquinoline (6.32g, 40mmol), 4-methoxybenzoic acid (6.08g, 40mmol) and dehydrating agent triphenyl phosphite (12.4g, 40mmol), Reflux in 100ml of xylene for 6 hours, remove the solvent in vacuo, and dissolve the residue with dichloromethane, perform basic alumina column chromatography, rinse with petroleum ether / ethyl acetate (10:1, v / v), The separated product was analyzed by thin layer chromatography, and the second eluent fraction (Rf=0.4) was collected, and the solvent was removed to obtain a white solid 4-methoxy-N-(2-methylquinoline) benzoic acid amide [ligand 1] 10.7 g, yield 92.0%. Melting point: 130-131°C.

[0062] The structural confirmation data are as follows:

[0063] 1 H NMR (CDCl 3 , 300MHz): δ10.77(s, N-H, 1H), 8.90(dd, J=7.5Hz, J=7.2Hz, 1H), 8.08(d, J=8.8Hz, 2H), 8.06(m, 1H) , 7.51(m, 2H), 7.36(d, J=8.5Hz, 1H), 7.06(d, J=...

Embodiment 2

[0067] Example 2, preparation of 4-methyl-N-(2-methylquinoline) benzoic acid amide [ligand 2]

[0068] Experimental procedure is with embodiment 1,2-methyl-8-aminoquinoline and 4-methylbenzoic acid condensation obtains white solid 4-methyl-N-(2-methylquinoline)-benzoic acid amide [ligand 2], rinsed with petroleum ether / ethyl acetate (10:1, v / v), separated the product by thin-layer chromatography, and collected the second elution fraction (Rf=0.4), with a yield of 91.2%. Melting point: 104-105°C.

[0069] The structural confirmation data are as follows:

[0070] 1 H NMR (CDCl 3 , 300MHz): δ10.84(s, N-H, 1H), 8.89(dd, J=7.0Hz, J=6.8Hz, 1H), 8.06(d, J=8.4Hz, 1H), 7.98(d, J= 8.8Hz, 2H), 7.54-7.47(m, 2H), 7.37-7.33(m, 1H), 7.22(d, J=8.4Hz, 2H), 2.78(s, CH 3 , 3H), 2.46(s, CH 3 , 3H).

[0071] 13 C NMR (CDCl 3 , 75MHz): δ162.0, 159.7, 154.3, 134.3, 133.1, 126.8, 126.0, 124.5, 122.4, 119.7, 118.3, 114.2, 112.9, 111.2, 22.4, 20.1.FT-IR (KBr, cm -1 ): 3345(m), 3050(w), 2913(w...

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Abstract

The invention discloses a cyclopentadiene-N-(2-methylquinoline) titanium benzoic amide coordination compound as well as a preparation method and application thereof. The coordination compound has a structural formula shown as a formula I, wherein R1-R10 are respectively hydrogen, methoxy, methyl or halogen; and Cp' is cyclopentadienyl, methyl cyclopentadienyl or pentamethyl cyclopentadienyl. A catalyst composition prepared from the cyclopentadiene-N-(2-methylquinoline) titanium benzoic amide coordination compound and a trialkylaluminum compound can catalyze ethylene homopolymerisation / Alpha-olefin copolymerization by higher activity. A titanic coordination compound containing the pentamethyl cyclopentadienyl and a methoxy-substituted coordination compound shows higher activity which reaches 4540kg.mol-1(Ti).h-1 to the maximum. Polyethylene with higher molecular weight reaching 437kg.mol-1 can be obtained by using the coordination compound containing the cyclopentadienyl to catalyze vinyle polymerization; activity for ethylene / 1-hexene copolymerization can reach 2380kg.mol-1(Ti).h-1, the molecular weight reaches 213kg.mol-1, and the content of comonomer 1-hexylene in a copolymer ranges 0.5 mol percent to 20 mol percent.

Description

technical field [0001] The invention relates to cyclopentadiene-N-(2-methylquinoline)benzoic acid amide titanium complex and its preparation method and application. Background technique [0002] Due to its unique properties, polymer materials have become a very important class of materials, and their application range has penetrated into various fields of production and life, and will play a greater role. Half of the usage of polymer materials is polyolefin resin. Compared with other resin materials, polyolefin resin has excellent environmental coordination. It is a material that is used for key promotion in the automobile industry in developed countries. It reached 83.3 million tons; among them, polyethylene is the synthetic resin with the fastest development, the largest output and extremely wide uses, reaching 51.1 million tons that year. Industrialized polyethylene catalysts have Ziegler-Natta type catalysts (DE Pat 889229 (1953); IT Pat 545332 (1956) and IT Pat536899 (...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/00C08F4/6592C08F10/02
Inventor 张文娟刘绍峰孙文华
Owner INST OF CHEM CHINESE ACAD OF SCI