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Unsaturated cyclosubstituted diacid ester compound suitable for preparing olefin polymerization catalyst

A technology of compounds and diacids, applied in the field of unsaturated ring-substituted diacids, which can solve the unsatisfactory balance of activity/isotacticity, etc.

Inactive Publication Date: 2014-09-24
BEIJING LIHE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the activity / isotacticity balance of Ziegler-Natta catalyst components prepared with the above compounds for olefin polymerization is not satisfactory, so further research and development is required

Method used

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  • Unsaturated cyclosubstituted diacid ester compound suitable for preparing olefin polymerization catalyst
  • Unsaturated cyclosubstituted diacid ester compound suitable for preparing olefin polymerization catalyst
  • Unsaturated cyclosubstituted diacid ester compound suitable for preparing olefin polymerization catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Synthesis of fluorene-9-methyl formate-9-ethyl formate

[0053] Step A: Add 18g of sodium hydride, 50g of fluorene, and 150mL of toluene to a 1000mL three-necked flask in sequence under nitrogen protection, turn on mechanical stirring, heat up to 125°C under reflux, and keep the reaction for 4h; cool down to 90°C, and slowly add 146.1 g diethyl carbonate, drop it within 1.5 hours, and continue to react for 3 hours after the drop; cool to 20°C, slowly add a mixture of 60g concentrated hydrochloric acid and 75g water, and control the temperature not to exceed 40°C; filter and separate the organic phase, washed with water until neutral, and the organic phase was rotary evaporated to obtain a reddish-brown liquid; the liquid obtained by rotary evaporation was refluxed overnight with 157.4g of acetic acid and 63g of 10% hydrochloric acid; the mixture was lowered to 20°C and separated; the organic phase was rotary evaporated Then add 30% NaOH solution to adjust ...

Embodiment 2

[0057] Example 2 Synthesis of fluorene-9,9-diethyl carboxylate

[0058] (1.6M, 15mmol) n-butyllithium / hexane solution was added dropwise at -78°C to 20mL tetrahydrofuran solution containing 16mmol diisopropylamine, the above solution was stirred at -78°C for 45 minutes, and After stirring at 0°C for 20 minutes, the temperature was lowered to -78°C. A 20 mL tetrahydrofuran solution containing 7.0 mmol fluorene was added dropwise to the above stirring solution within 30 minutes at -78°C, and 33 mmol of ethyl chloroformate was added to the above mixture. The reaction system was warmed up to room temperature and stirred at room temperature for 3 hours. The above reaction mixture was poured into 100 mL of water, extracted with ether (three extractions, 50 mL of ether each time), the organic phase was dried with magnesium sulfate, and the crude product obtained after concentration was recrystallized with petroleum ether to obtain the product at 100-101°C.

[0059] Diethyl fl...

Embodiment 3

[0060] Example 3 Synthesis of fluorene-9,9-dimethyl-dicarboxylate

[0061] The synthesis steps are the same as in Example 2, except that ethyl chloroformate is replaced by methyl chloroformate.

[0062] Dimethyl fluorene-9,9-dicarboxylate 1 H-NMR (CDCl 3 )δ (ppm): 3.759 (s, 6H, methyl hydrogen), 7.359-7.392 (t, 2H, aromatic ring hydrogen), 7.443-7.475 (t, 2H, aromatic ring hydrogen), 7.720-7.735 (d, 2H , aromatic ring hydrogen), 7.799-7.7814 (d, 2H, aromatic ring hydrogen).

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Abstract

The invention provides an unsaturated cyclosubstituted diacid ester compound and a preparation method thereof, and application of the unsaturated cyclosubstituted diacid ester compound in preparing an olefin polymerization catalyst component. When being used for preparing the Ziegler-Natta catalyst component as an electron donor, the compound can enable the catalyst component to have excellent activity and polymer products with high degree of isotacticity can be obtained.

Description

technical field [0001] The present invention relates to a kind of unsaturated ring substituted diacid ester compound, the preparation method of this compound and its CH 2 = Use in the preparation of CHR olefin polymerization catalysts, wherein R is hydrogen or a hydrocarbyl group containing 1-12 carbon atoms. Background technique [0002] The electron donor compound can change the nature of the active center of the olefin polymerization Ziegler-Natta catalyst to the greatest extent, thereby changing the performance of the catalyst to the greatest extent, so the research on the high-efficiency Ziegler-Natta catalyst is in a sense, It is the research of seeking better electron donors. At present, domestic and foreign research on internal electron donors mainly focuses on traditional fatty acid esters and aromatic ester compounds; diethers (such as EP0361493, EP0728724) and succinates (such as WO9856834, WO0063261, WO03022894) compounds; Alcohol esters (such as CN1580033, CN1...

Claims

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Application Information

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IPC IPC(8): C07C69/753C07C67/36C07C205/49C07C229/48C07C69/74C07C69/76C07D207/22C07D495/04C07D487/04C07D231/56C07D231/54C07D209/42C07D233/44C07D233/28C07D333/38C07D211/90C07D213/73C07D309/32C07D335/02C07D487/14C07D237/04C07D215/50C07F7/08C08F4/649
CPCC07C69/753C07C69/74C07C69/76C07C205/49C07C229/48C07D207/22C07D209/42C07D211/90C07D213/73C07D215/50C07D231/54C07D231/56C07D233/28C07D233/44C07D237/04C07D309/32C07D333/38C07D335/02C07D487/04C07D487/14C07D495/04C07F7/081C08F10/00C08F4/6494
Inventor 王志武李树行李华姝张军伟章慧陈业娜代金松马庆利王敬禹李树宾陈颢雷凤瑶白伟李利革高勇
Owner BEIJING LIHE TECH
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