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Gamma-alkyl heteroatom substituted ether and its synthesis method

A carbon atom and ether compound technology, which is applied in the application field of 9--9-fluorene compound and the preparation of olefin polymerization catalyst, can solve problems such as difficult synthesis, achieve good performance and improve the effect of activity

Inactive Publication Date: 2005-02-16
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, 9-(hydroxymethyl)-9-(halomethyl)fluorene is difficult to synthesize

Method used

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  • Gamma-alkyl heteroatom substituted ether and its synthesis method
  • Gamma-alkyl heteroatom substituted ether and its synthesis method
  • Gamma-alkyl heteroatom substituted ether and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Preparation of 9-(methoxymethyl)-9-(hydroxymethyl)fluorene

[0058] In an anhydrous and nitrogen atmosphere, 80ml of tetrahydrofuran (THF), 22.6g of 9,9-bis(hydroxymethyl)fluorene and 57g of methyl iodide were sequentially added, and stirred to make the mixture completely uniform. At room temperature, 4.6 g of sodium hydride with a content of 52% was added in portions during 2 hours, and stirring was continued for 2 hours after the addition was complete.

[0059] Unreacted methyl iodide was recovered by distillation, the remaining material was diluted with 100ml of water, and extracted twice with diethyl ether, 100ml each time. 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, with a yield of 62%.

[0060] 1 H-NMR (C...

Embodiment 2

[0062] Preparation of 9-(methoxymethyl)-9-(sulfonyloxymethyl)fluorene

[0063] 5.45g of 9-(methoxymethyl)-9-(hydroxymethyl)fluorene was dissolved in 50ml of dichloromethane. The solution was cooled to -5-0°C, 4ml of triethylamine and 2.2ml of methanesulfonyl chloride were added in sequence, and the reaction was stirred for 6 hours. Then, the reaction solution was washed with water and a saturated aqueous solution of sodium bicarbonate, respectively. The separated organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated to obtain 14.2g of 9-(methoxymethyl)-9-(sulfonyloxymethyl)fluorene (96% yield), mp70~ 72°C.

[0064] 1 H-NMR (CDCl 3 / TMS) δ (ppm): 2.85 (s, 3H, -OSO 2 CH 3 ), 3.40 (s, 3H, -OCH 3 ), 3.60 (s, 2H, -CH 2 O-), 4.50(s, 2H, -CH 2 OSO 2 -), 7.32(t, 2H, J=7.6Hz, 2ArH), 7.43(t, 2H, J=7.2, 7.6Hz, 2ArH), 7.64(d, 2H, J=7.6Hz, 2ArH), 7.75(d , 2H, J=7.2Hz, 2ArH).

Embodiment 3

[0066] Preparation of 9-(methoxymethyl)-9-(ethylthiomethyl)fluorene

[0067] Under nitrogen protection, 18ml of dry toluene and 1g of sodium metal were added to the reaction flask, and then 6.8ml of ethanethiol was added. Stir at room temperature until the sodium metal reaction disappears. A solution of 5.8 g of 9-(methoxymethyl)-9-(sulfonyloxymethyl)fluorene dissolved in 58 ml of dimethylformamide (DMF) was added dropwise. The reaction solution was reacted in an oil bath at 40°C for 24 hours, and then reacted at 60-72°C for 7 hours. Cool to room temperature, add 120ml of toluene and 120ml of deionized water, shake to separate the water layer. The aqueous layer was extracted with 76 ml of toluene. The toluene layers were combined, washed with water, then dried over anhydrous sodium sulfate, and concentrated to obtain 4.6 g of 9-(methoxymethyl)-9-(ethylthiomethyl)fluorene (yield 88.6%), mp80-81 ℃. Mass spectrometry (EI) m / e: 284 (M + ).

[0068] 1 H-NMR (CDCl 3 / TMS) δ...

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PUM

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Abstract

A gamma-heteroatom substituted alkyl ether compound containnig fluorene structure, its synthesizing process, and its application to preparing the catalyst for olefin polymerization are disclosed. As shown in the ganeral formula, R1 and R2 may be the same or not the same, representing 1-20 C atom-contained straight chain or branching alkyl, cycloalkyl, aryl, alkaryl or aralkyl group; A represents S or Z-R3 groups, where Z is N or P and R3 represents H or 1-10 C atom-contained straight chain or branching alkyl, cycloalkyl, aryl, alkaryl or aralkyl group.

Description

technical field [0001] The present invention relates to a class of novel gamma-hydrocarbyl heteroatom-substituted ether compounds containing a fluorene structure, in particular to a class of 9-(hydrocarbyloxymethyl)-9-(hydrocarbylthiomethyl)fluorene compounds, The preparation method of the compound and the application of the compound in the preparation of olefin polymerization catalysts. Background technique [0002] It is known that 1,3-diether compounds are used as electron donors in olefin polymerization catalysts, for example, 1,3-propylene diether compounds containing fluorene structure disclosed in documents CN1298887 and CN1143651 and heteroatom-containing polycyclic Alkene 1,3-propanediether derivatives, etc. [0003] At present, the literature reports two synthetic methods of β-oxyl sulfide compounds: [0004] The first method is to prepare β-alkoxy sulfide by reacting β-alkoxy haloalkane with sodium mercaptide, as reported in the literature, 1-chloro-2-ethoxyetha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/567C07C43/168C08F10/00
Inventor 谢伦嘉赵思源李天益张明森吴长江刘海涛王占英
Owner CHINA PETROLEUM & CHEM CORP
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