High-solubility triaryl carboborate as well as preparation method and application thereof

A triarylcarboborate, high solubility technology, applied in the field of high solubility triarylcarboborate and its preparation, can solve the problems of increased separation cost, high price, and rare reports on the development of efficient organoboron

Active Publication Date: 2020-09-22
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the cost of producing these high-performance polyolefins is relatively high, mainly because a large amount of high-priced MAO or MMAO needs to be added in the production of these high-performance polyolefins, thereby increasing the cost
In addition, the addition of a large amount of MAO or MMAO introduces a large amount of ash into the polyolefin, which limits its application. Therefore, the development of a co-catalyst with good effect and low addition is to promote the production of metallocene polyolefin and solution-processed homogeneous catalyst with high performance. The focus of polyolefin development
Organic boron additives solve this problem to a certain extent, but at present most patents such as CN103304587A, US5473036, JP09295985, US6162950, ​​US6169208, US6241917 report organic boron has low solubility in alkane, and it is easy to be carried in polymerization during use. into other polar solvents, thus increasing the cost of separation
Moreover, these patents also mainly focus on optimizing the synthesis route of a certain organic boron agent, and the development of new high-efficiency organic boron is rarely reported.
In addition, although the existing boron agent is used as a cocatalyst to catalyze olefin polymerization together with the main catalyst, although it has certain applications in industry, it is easy to form a relatively stable ion pair with the main catalyst because of its small structural hindrance, thereby To a certain extent, the coordination of olefins in the active center of the main catalyst is limited, thereby limiting the further improvement of catalytic activity and the improvement of catalytic efficiency. In actual production, the capacity of the device is limited, so the development of new additives It is of great significance to promote the further development of olefin polymerization

Method used

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  • High-solubility triaryl carboborate as well as preparation method and application thereof
  • High-solubility triaryl carboborate as well as preparation method and application thereof
  • High-solubility triaryl carboborate as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1, the preparation of compound 3

[0046]

[0047] (1) Under the standard schlenk technique, add 15.6 g of 2,2'-dibromobiphenyl (0.05 mol) into the reaction flask, add 100 mL of toluene as a solvent, and start stirring. Then, 62.5 mL of butyllithium hexane solution (0.1 mol, 2 eq., 1.6 mol / L) was added to the solution at -78°C, slowly raised to room temperature, and stirred for 48 h. Then, 52.5 mL of boron tribromide dichloromethane solution (0.0525 mol, 1.05 eq., 1 mol / L) was added at -78 ° C, and after the addition was completed, it was raised to room temperature and stirred for 12 h. After the reaction, the solvent was sucked dry. Then, 150 mL of toluene was added to the reaction flask, and then 17.4 g of (pentafluorophenyl) lithium (0.1 mol, 2 eq.) was added, and the reaction was stirred for 8 h. After the reaction, add an appropriate amount of water to stir, and then stand still to separate the liquids to obtain the upper layer (toluene layer) clear ...

Embodiment 2

[0051] Embodiment 2, the preparation of compound 4

[0052]

[0053] (1) Under a nitrogen atmosphere, accurately weighed 1,2-dibromotetrafluorobenzene (61.57 g, 0.2 mol) and 200 mL of anhydrous tetrahydrofuran were added into a dry two-neck round bottom flask. Then the solution was cooled to -78°C, and 125 mL of n-hexane solution of butyllithium (0.2 mol, 1.6 mol / L, 1 eq.) was added dropwise under vigorous stirring. After the dropwise addition, continue to stir at this temperature for 10 min and then slowly rise to room temperature, then add 21.6 g of 1,4-dibromobutane (0.1 mol, 0.5 eq.) and stir overnight. After the reaction was completed, 25mL of 5% hydrochloric acid solution was added to the solution, the organic layer was separated, the aqueous layer was extracted with ether (20mL×4), the organic layers were combined and washed with anhydrous MgSO 4 dry. The solvent was spun off with a rotary evaporator to obtain an off-white solid. Recrystallized with absolute ethan...

Embodiment 3

[0058] Embodiment 3, the preparation of compound 5

[0059]

[0060](1) Under the condition of anhydrous and anaerobic nitrogen blowing reflux, add 60mL of 3-chlorophenylmagnesium bromide THF solution (0.03mol, 0.5mol / L) to the reaction flask at room temperature and then start stirring, slowly 1.18 g of diethyl carbonate (0.01 mol, 1 / 3 eq.) was added dropwise, and after the addition was complete, the reaction bottle was placed in an oil bath and refluxed at 80° C. for 12 h. After the reaction is completed, cool to room temperature, then add 60 mL of octadecylmagnesium chloride THF solution (0.03 mol, 0.5 mol / L, 1 eq.) dropwise to the reaction solution, stir for 4 hours, and dropwise add saturated ammonium chloride aqueous solution, a large amount of magnesium hydroxide precipitated immediately. Continue to drop the solution until the layers are separated and the upper layer is clear. Separate the supernatant, dissolve the lower layer with dilute hydrochloric acid, and extra...

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Abstract

The invention relates to high-solubility triaryl carboborate as well as a preparation method and application thereof. The structural general formula is shown in the specification. The high-solubilitytriaryl carboborate has the advantages of cheap and easily available raw materials, quite simple synthesis and high solubility in an alkane solvent, can be used as a cocatalyst to catalyze olefin polymerization, solves the problem that the cocatalyst needs to be dissolved in a polar solvent, and is beneficial to reduction of solvent separation and cost reduction in an olefin solution polymerization process. In addition, the structural rigidity and steric hindrance of the anion part of the boron agent with the structure are increased due to bridging, and the coordination effect with a main catalyst is reduced while the anion part serving as a cocatalyst stabilizes the cation center of the main catalyst, so that the olefin coordination capability is enhanced, and the activity is greatly improved.

Description

technical field [0001] The invention relates to the technical field of olefin polymerization co-catalysts, in particular to a high-solubility triarylcarboborate and its preparation method and application. Background technique [0002] Polyolefin products have become the most popular resin materials because of their abundant raw materials, low price, convenient production and processing, and superior performance. Moreover, with the improvement of people's living standards and the new needs of some special fields, there is an increasing demand for high-performance polyolefins produced by homogeneous catalysts such as metallocene polyolefins and solution methods. However, the cost of producing these high-performance polyolefins is relatively high, mainly because a large amount of high-priced MAO or MMAO needs to be added in the production of these high-performance polyolefins, thereby increasing the cost. In addition, the addition of a large amount of MAO or MMAO introduces a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C08F10/00C08F110/02C08F4/6592
CPCC07F5/02C08F10/00C08F110/02C08F4/6592
Inventor 王金强郭华张彦雨古亮亮苗春萌林小杰张田财郗朕捷刘万弼刘帮明陈冠良黄玲燕石正喜黄明路
Owner WANHUA CHEM GRP CO LTD
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