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Pyridine diimine iron olefin polymerizing catalyst, as well as preparation method and application thereof

A technique for the polymerization of iron pyridinediimide and olefins, which is applied in the direction of iron organic compounds, etc., which can solve the problems of complex preparation process and short catalytic life of catalysts, and achieve the effects of simple preparation method, increased molecular weight, and extended service life

Inactive Publication Date: 2009-04-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During catalytic polymerization, the aryl ortho substituent R 2 Catalysts with low steric hindrance have a short catalytic life, and only low molecular weight polyolefins or oligomers can be obtained
[0007] Li Yuesheng of Changchun Institute of Applied Chemistry prepared a cyclic or multinuclear pyridinediimide iron catalyst, which can improve the inhibition of deactivation of this type of catalyst and improve its service life (CN 1245424C, CN1250577C, CN 1306014A), but the complex The preparation process is complicated

Method used

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  • Pyridine diimine iron olefin polymerizing catalyst, as well as preparation method and application thereof
  • Pyridine diimine iron olefin polymerizing catalyst, as well as preparation method and application thereof
  • Pyridine diimine iron olefin polymerizing catalyst, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The asymmetrically substituted amine represented by formula (IV) prepared in this example, wherein R 1 =H,R 2 =CH 3 , the preparation process is as follows:

[0044] Under a nitrogen atmosphere, 15 mL of styrene and 2 mL of trifluoromethanesulfonic acid were injected into a reactor containing 25 ml of p-toluidine xylene solution (containing 13.9 g of p-toluidine xylene), and the reaction was stirred and refluxed at 130 °C. After 30 hours, the product was an orange-red oil, which was separated by a silica gel column, and the eluent was a mixed solvent of petroleum ether:ethyl acetate=20:1 (volume ratio) to obtain 5.31 g of a light red oil, which was The target product of this example has a yield of 19.4%.

[0045] 1 H NMR (300MHz, CDCl 3 ): δ (ppm): 6.9-7.3 (m, 7H, aryl-H), 6.59 (d, 1H, aryl-H), 4.12 (q, 1H, CHCH 3 ), 3.30 (2H, NH 2 ), 2.35(s, 3H, p-CH 3 ), 1.67(d, 3H, CHCH 3 ).

[0046] Mass spectrum EI-MS (m / z): 212.2 [M] + .

Embodiment 2

[0048] The asymmetrically substituted amine represented by formula (IV) prepared in this example, wherein R 1 =CH 3 , R 2 =CH 3 , the preparation process is as follows:

[0049] Under a nitrogen atmosphere, 20 mL of styrene and 3 mL of trifluoromethanesulfonic acid were injected into a reactor containing 25 mL of xylene solvent (containing 15 mL of 2,4-dimethylaniline), and the reaction was stirred and refluxed at 160° C. for 30 hours. The crude product obtained from the reaction was recrystallized with a mixed solvent of petroleum ether and ethyl acetate (v:v=20:1) to obtain 8.43 g of white flocculent crystals, which was the target product of this example, with a yield of 31%.

[0050] 1 H NMR (300MHz, CDCl 3 ): δ (ppm): 7.16-7.30 (m, 5H, aryl-H), 6.99 (s, 1H, aryl-H), 6.84 (s, 1H, aryl-H), 4.12 (q, 1H, CHCH) 3 ), 2.30(s, 3H, p-CH 3 ), 2.13(s, 3H, O-CH 3 ), 1.62 (d, 3H, CHCH3).

[0051]Mass spectrum EI-MS (m / z): 226.2 [M] + .

Embodiment 3

[0053] The asymmetrically substituted amine represented by formula (IV) prepared in this example, wherein R 1 =H,R 2 =OCH 3 , the preparation process is as follows:

[0054] Under a nitrogen atmosphere, 13 mL of styrene and 2 mL of trifluoromethanesulfonic acid were injected into a reactor equipped with 25 ml of xylene solvent (containing 15.7 g of p-methoxyaniline), and the reaction was stirred and refluxed at 160 ° C for 30 hours. It was an orange-red oil, and the product was separated by a silica gel column, and the eluent was a mixed solvent of petroleum ether: ethyl acetate=5:1 (volume ratio) to obtain 3.19 g of white crystals, which was the target product of this example. , the yield is 11%.

[0055] 1 H NMR (300MHz, CDCl 3 ): δ (ppm): 7.18-7.30 (m, 5H, aryl-H), 6.91 (s, 1H, aryl-H), 6.58-6.69 (m, 2H, aryl-H), 4.11 (q, 1H, CHCH 3 ), 3.80(s, 3H, p-OCH 3 ), 3.18 (2H, NH 2 ), 1.61(d, 3H, CHCH 3 ).

[0056] Mass spectrum EI-MS (m / z): 228.5 [M] + .

[0057] 2. Pr...

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Abstract

The invention discloses a bis (imino) pyridine iron olefin polymerization catalyst and a preparation method and application thereof. The catalyst is a novel bis(imino)pyridine iron complex with the asymmetric substitution of position 2 and 6 of an aromatic ring; and the structural formula of the catalyst is shown in formula (I), wherein X is halogen, R1 is alkyl, and R2 is the alkyl or oxyl. The catalyst can be obtained through a Friedel-Crafts reaction, a ketoamine condensation reaction and a coordination reaction. The preparation method is simple, and raw materials are cheap. The catalyst can catalyze the polymerization of ethylene under the activation of MAO to prepare polyethylene with high molecular weight and wide distribution.

Description

technical field [0001] The invention relates to the field of olefin catalytic polymerization, in particular to a pyridinediimide iron olefin polymerization catalyst and a preparation method and application thereof. Background technique [0002] Polyolefin is one of the most widely used resins, and its output accounts for more than half of the total output of polymer materials. Due to its excellent processing and use performance and low price, it has become the world's largest output and consumption of synthetic resin varieties. Widely used. Used in industry, agriculture, national defense, transportation and people's daily life. Among them, the catalyst is the core of the development of the polyolefin industry and the key to control the structure and properties of the polyolefin. [0003] On the basis of the traditional propylene polymerization catalyst system (Ziegler-Natta catalyst), a metallocene catalyst with a single active center has been found, which can catalyze the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F4/70C08F10/00C08F10/02C07F15/03
Inventor 郭丽华高海洋伍青张玲
Owner SUN YAT SEN UNIV
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