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Large sterically hindered flexible diimine ligands, nickel and palladium diimine complexes based thereon and their catalytic applications

A technology of diimine ligand and diimine palladium, which is applied in the preparation of imino compounds, palladium organic compounds, nickel organic compounds, etc., can solve the problems of increasing the activation energy of ethylene monomer, disadvantages, etc., and achieve good catalytic activity, Excellent elastic recovery performance, the effect of good recovery performance

Active Publication Date: 2022-08-09
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Basically, these catalysts not only exhibit good thermal stability but are also capable of producing polyolefins with higher molecular weights, tunable branching densities, and efficient incorporation of polar comonomers, but their rigid sterically hindered substituents It will prevent the insertion of ethylene monomer or significantly increase the activation energy of ethylene monomer insertion, which is not conducive to the progress of polymerization
The use of α-diimine ligands with flexible steric hindrance for nickel and palladium catalyzed olefin polymerization may solve the above problems, but there are no related reports so far.

Method used

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  • Large sterically hindered flexible diimine ligands, nickel and palladium diimine complexes based thereon and their catalytic applications
  • Large sterically hindered flexible diimine ligands, nickel and palladium diimine complexes based thereon and their catalytic applications
  • Large sterically hindered flexible diimine ligands, nickel and palladium diimine complexes based thereon and their catalytic applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] In this example, a large sterically hindered flexible diimine ligand L1 is prepared, and its structure is as follows:

[0042]

[0043]The synthesis process is as follows: under nitrogen atmosphere, acenaphthene quinone (0.55g, 3mmol, 1.0eq) and 2,6-bis(pent-3-yl)aniline (1.54g, 6.6mmol, 2.2eq) were respectively suspended in acetonitrile (40mL) ) and acetic acid (16 mL), then mixed. The mixture was vigorously stirred at 90°C for 12 hours, turning into a reddish-brown solution. Subsequently, the solution was cooled to room temperature and the yellow precipitate was collected by filtration. The solid was washed with acetonitrile, and after vacuum drying, L1 was obtained as a yellow powder in 74% yield (1.36 g). 1 H NMR (500MHz, CDCl 3 )δ7.84(d, J=8.2Hz, 2H, Ar-H), 7.32(t, J=7.7Hz, 2H, Ar-H), 7.19(m, 6H, Ar-H), 6.68(d, J=7.1Hz, 2H, Ar-H), 2.62 (m, 4H, CH), 1.66 (m, 4H, CH) 2 ),1.57(m,4H,CH 2 ),1.48(m,4H,CH 2 ),1.40(m,4H,CH 2 ),0.83(s,12H,CH 3 ),0.52(s,12H,CH 3...

Embodiment 2

[0045] The present embodiment prepares a large sterically hindered flexible diimine ligand L2, and its structure is as follows:

[0046]

[0047] The same method was used for the synthesis of L1, except that 2,6-bis(hept-4-yl)aniline (1.91 g, 6.6 mmol, 2.2 equiv) was used. L2 was obtained as a yellow powder in 71% yield (1.54 g). 1 H NMR (500MHz, CDCl 3 )δ7.82(d,J=8.2Hz,2H,Ar-H),7.33-7.29(m,2H,Ar-H),7.19-7.14(m,6H,Ar-H),6.66(d,J = 7.2Hz, 2H, Ar-H), 2.79–2.73 (m, 4H, CH), 1.54 (ddd, J = 16.2, 9.3, 5.6Hz, 4H, CH) 2 ),1.49–1.38(m,8H,CH 2 ),1.39–1.30(m,4H,CH 2 ),1.30–1.15(m,8H,CH 2 ),0.91(tdd,J=13.9,11.2,6.6Hz,8H,CH 2 ),0.80(t,J=7.3Hz,12H,CH 3 ),0.34(t,J=7.3Hz,12H,CH 3 ). 13 C NMR (126MHz, CDCl 3 )δ160.51(C=N),149.86,140.65,133.41,130.87,129.88,128.58,127.38,124.64,123.93,123.57,38.98,38.79,37.27,20.66,20.57,14.55,14.00 z): Calculate C 52 H 73 N 2 :725.5774,Actual measurement,725.5754,[M+H] + .

Embodiment 3

[0049] The present embodiment prepares a large sterically hindered flexible diimine ligand L3, and its structure is as follows:

[0050]

[0051] The same method was used for the synthesis of L1, except that 2,6-bis(non-5-yl)aniline (2.28 g, 6.6 mmol, 2.2 equiv) was used. The resulting L3 was a yellow powder with a yield of 96.0% (2.41 g). 1 H NMR (500MHz, CDCl3): δ7.81 (d, J=8.2Hz, 2H, Ar-H), 7.30 (t, J=7.7Hz, 2H, Ar-H), 7.20–7.14 (m, 6H Ar -H), 6.67 (m, 2H, Ar-H), 2.76–2.69 (m, 4H, CH), 1.62–1.55 (m, 4H, CH) 2 ),1.44(m,8H,CH 2 ),1.39–1.32(m,4H,CH 2 ),1.27–1.20(m,8H,CH 2 ),1.18–1.12(m,6H,CH 2 ),0.91–0.71(m,30H,CH 2 ,CH 3 ),0.35(t,J=6.6Hz,12H,CH 3 ). 13 C NMR (126MHz, CDCl 3 ):δ160.70(C=N),150.25,140.96,133.67,131.20,130.15,128.73,127.64,124.92,124.34,123.78,39.94,36.69,34.92,30.40,29.82,23.44,3.98.70 -MS(m / z): Calculate C 60 H 89 N 2 :837.7026,Actual measurement,837.7012,[M+H] +

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Abstract

The invention discloses large sterically hindered flexible diimine ligands, diimine nickel and palladium complexes based thereon and their catalytic applications. By introducing flexible substituents of different structures on the diimine ligands, a series of The steric effect of nickel diimide and palladium catalysts. The catalyst obtained by the invention has high thermal stability and high activity for catalyzing olefin polymerization, and the catalyst can regulate the molecular weight and branching density of polyolefin by changing the chain length of the substituent.

Description

technical field [0001] The invention belongs to the technical field of polyolefin preparation, and in particular relates to a catalyst for alpha-olefin polymerization. Background technique [0002] Polyolefin materials are indispensable in people's production, life and industrial applications, and are widely used. Since its inception, the exploration of olefin polymerization catalysts has been a frontier issue in the field of polymer science. The quality and performance of polyolefin materials are closely related to catalysts, and every discovery and improvement of new catalysts has played a major role in promoting the olefin polymerization industry. Throughout the history of the olefin polymerization industry, technological progress has been closely related to the discovery of new catalysts and the successful development of technologies. During olefin polymerization, the catalyst often determines the polymerization behavior, particle morphology, topology, and properties o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/20C07C249/02C07F15/04C07F15/00C08F10/00C08F10/02C08F4/70
CPCC07C251/20C07F15/045C07F15/006C08F10/00C08F10/02C07C2603/20C08F4/7006Y02P20/584
Inventor 代胜瑜李帅康
Owner ANHUI UNIVERSITY
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