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Silicon ether compound and preparation method and application thereof

A kind of technology of compound and silyl ether, applied in the application field of preparing olefin polymerization catalyst, can solve problems such as synthesis method not reported in literature

Inactive Publication Date: 2004-11-03
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art has never used γ-[(trihydrocarbylsilyl)oxy]ether compounds as external electron donors for olefin polymerization, but, quite surprisingly, the inventors have found a class of γ-[(tri Hydrocarbylsiliconyl)oxyl]ether compounds, used as external electron donor compounds for olefin polymerization, with excellent performance
Compound 9-(alkoxymethyl)-9-[(trihydrocarbylsilyl)oxymethyl]fluorene compounds and 9,9-bis[(trihydrocarbylsilyl)oxymethyl]fluorene compounds are both It is a special γ-[(trihydrocarbyl silyl)oxyl] ether compound, and there are no literature reports on these two compounds and their synthetic methods

Method used

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  • Silicon ether compound and preparation method and application thereof
  • Silicon ether compound and preparation method and application thereof
  • Silicon ether compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Preparation of 9-(methoxymethyl)-9-(hydroxymethyl)fluorene

[0074] Under nitrogen protection and anhydrous conditions, 80ml of tetrahydrofuran, 22.6g of 9,9-bis(hydroxymethyl)fluorene and 57g of methyl iodide were sequentially added, stirred and the reactants were completely mixed evenly. At room temperature, within 2 hours, 4.6 g of sodium hydride with a content of 52% was added in batches, and stirring was continued for 2 hours after the addition was completed.

[0075] Unreacted methyl iodide was recovered by distillation, and the remaining material was diluted with 100 ml of water and extracted twice with 100 ml of ether. The ether extracts were combined and dried by adding anhydrous sodium sulfate. After the dried ether solution was evaporated to dryness, 22.8 g of crude product were obtained. After separation and purification by column chromatography, 14.9 g of 9-(methoxymethyl)-9-(hydroxymethyl)fluorene was obtained (yield 62%).

[0076] 1 H-NMR (CDCl 3 / TM...

Embodiment 2

[0078] Preparation of 9-(methoxymethyl)-9-[(trimethylsilyl)oxymethyl]fluorene

[0079] 1g of 9-(methoxymethyl)-9-(hydroxymethyl)fluorene was dissolved in 20ml of dichloromethane. The solution was cooled below 5°C, 0.7ml of triethylamine was added, stirred for 5 minutes, then 0.6ml of trimethylchlorosilane was added dropwise, and stirred for 2 hours. Stir for an additional 1 hour at room temperature. The reaction solution was washed with water, and the separated organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 1.41 g of a concentrate (yield 86%). Mass spectrometry (EI) m / e: 312 (M+).

[0080] 1H-NMR (CDCl3 / TMS) δ (ppm): 0.15 (s, 9H, 3CH3), 3.42 (s, 3H, -OCH3), 3.74 (s, 2H, -CH2O-), 3.82 (s, 2H, - CH2O-), 7.36(t, 2H, ArH), 7.44(t, 2H, ArH), 7.70(d, 2H, ArH), 7.80(d, 2H, ArH).

Embodiment 3

[0082] Preparation of 9,9-bis[(trimethylsilyl)oxymethyl]fluorene

[0083] Mix 1 g of 9,9-bis(hydroxymethyl)fluorene and 20 ml of dichloromethane, and cool the mixture with an ice bath. 1.9 ml of triethylamine was added to the mixture, and 1.4 ml of trimethylsilyl chloride was added dropwise. Stir under ice bath for 2 hours. The reaction solution was washed with water, and the organic layer was separated, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 1.14 g of a concentrate (yield 88%). Mass spectrometry (EI) m / e: 370 (M+).

[0084] 1 H-NMR (CDCl 3 / TMS) δ (ppm): 0.08 (s, 18H, 6CH 3 ), 3.77 (s, 4H, 2-CH 2 O-), 7.26(t, 2H, ArH), 7.38(t, 2H, ArH), 7.62(d, 2H, ArH), 7.72(d, 2H, ArH).

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Abstract

The present invention relates to one new kind o silyl-ether compound and its preparation and application. The compound has the structure shown in the general expression (I).

Description

technical field [0001] The invention relates to a novel silicon ether compound, a preparation method of the compound and an application of the compound in preparing an olefin polymerization catalyst. Background technique [0002] WO 00 / 63261 discloses external electron donor compounds (external electron donors) for the polymerization of olefins, ie of the general formula R 11 R 12 bSi(OR 13 ) a silicon compound of c, wherein a and b are integers from 0 to 2, c is an integer from 1 to 3 and the sum of (a+b+c) is 4, R 11 , R 12 and R 13 respectively C 1 ~C 18 Hydrocarbyl, optionally containing heteroatoms. Wherein particularly preferred silicon compound, a is 1, b is 1, c is 2, R 11 and R 12 At least one of R is selected from branched alkyl, alkenyl, alkylene, cycloalkyl or aryl groups having 3 to 10 carbon atoms, optionally containing heteroatoms, and R 13 for C 1 ~C 10 Alkyl groups, especially methyl groups, such as cyclohexylmethyldimethoxysilane. In addition, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C08F10/00C08F110/06
CPCC07F7/1856C08F110/06C08F10/00C07F7/1804C08F4/6465C08F2500/15C08F2500/12
Inventor 谢伦嘉高明智李天益赵思源张明森吴长江
Owner CHINA PETROLEUM & CHEM CORP
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