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A kind of preparation method of bicyclohexane liquid crystal monomer

A technology of liquid crystal monomer and dicyclohexane, which is applied in the field of preparation of liquid crystal monomer materials, can solve the problems of short synthesis route, unfavorable product yield and purity, high activity, etc., achieve short synthesis route, reduce the cost of synthetic raw materials, and chemical stable effect

Active Publication Date: 2011-11-30
江苏广域化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although the synthesis route of this reaction is short, it uses alkyl acid chloride as the starting raw material, and the raw material itself has high activity and is easily hydrolyzed, which is unfavorable to the yield and purity of the product.

Method used

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  • A kind of preparation method of bicyclohexane liquid crystal monomer
  • A kind of preparation method of bicyclohexane liquid crystal monomer
  • A kind of preparation method of bicyclohexane liquid crystal monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] compound resolve resolution:

[0047] (1) Preparation of trans-4-(trans-4-propylcyclohexyl) methyl cyclohexylcarboxylate

[0048] Add 200g (7.5mol) methanol and 130g (0.56mol) trans-4-(trans-4-propylcyclohexyl) cyclohexyl formic acid in the reaction vessel, add 147g (1.5mol) dropwise to the reaction vessel under stirring Concentrated H 2 SO 4 , the temperature is controlled at 65°C, after the reaction is completed for 12 hours under stirring, the liquid is separated after cooling, and the lower layer is separated, and the upper layer is the product layer. The lower sulfuric acid layer was extracted with petroleum ether, the organic layers were combined, and the organic layer was washed with water until neutral. The organic layer was concentrated to obtain 139.1 g of the compound methyl trans-4-(trans-4-propylcyclohexyl)cyclohexylcarboxylate.

[0049] H-NMR of the obtained product trans-4-(trans-4-propylcyclohexyl)cyclohexylcarboxylate methyl ester: δ0.8-0.9(5H), 0...

Embodiment 2

[0059] compound resolve resolution:

[0060] (1) Preparation of trans-4-(trans-4-propylcyclohexyl) methyl cyclohexylcarboxylate

[0061] Add 240g (7.5mol) methanol and 126g (0.56mol) trans-4-(trans-4-propylcyclohexyl) cyclohexyl formic acid in the reaction vessel, add 147g (1.5mol) dropwise to the reaction vessel under stirring Concentrated H 2 SO 4 , the temperature is controlled at 65°C, after the reaction is completed for 12 hours under stirring, the liquid is separated after cooling, and the lower layer is separated, and the upper layer is the product layer. Extract the lower sulfuric acid layer with 100ml×3 petroleum ether at 100°C, combine the organic layers, and wash the organic layers with water until neutral. The organic layer was concentrated to obtain 136 g of methyl trans-4-(trans-4-propylcyclohexyl)cyclohexylcarboxylate.

[0062] H-NMR of the obtained product trans-4-(trans-4-propylcyclohexyl)cyclohexylcarboxylate methyl ester: δ0.8-0.9(5H), 0.9-1.1(6H), 1.2...

experiment example 3

[0072] compound resolve resolution:

[0073] (1) Preparation of trans-4-(trans-4-heptylcyclohexyl)cyclohexyl formate methyl ester

[0074] 240 g of methanol and 157 g of trans-4-(trans-4-heptylcyclohexyl)cyclohexylcarboxylic acid were added to the reaction vessel. Add 134 g of concentrated H dropwise to the reaction vessel with stirring 3 PO 4 , temperature controlled at 70°C, stirred and reacted for 8 hours, cooled and allowed to stand for liquid separation, the lower sulfuric acid layer was separated, and the upper layer was the product layer. The sulfuric acid layer in the lower layer was extracted with petroleum ether at a temperature of 120°C, and the organic layers were combined. The organic layer was washed with water until neutral, and the organic layer was concentrated to obtain 163 g.

[0075] (2) Preparation of trans-4-(trans-4-heptylcyclohexyl)cyclohexylmethanol

[0076] 24.6g of calcium chloride, 29g of sodium borohydride were added to 350ml of tetrahydrofu...

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Abstract

The invention provides a method for synthesizing bicyclohexane-based liquid crystal monomers. (1) take it as a raw material, and undergo esterification reaction with methanol under acidic conditions to obtain compound III; (2) use borohydride or aluminum hydride and The metal salt mixed system is a reducing agent, and the compound III generated in step (1) is reduced to compound IV in an organic solvent; (3) compound IV reacts with p-toluenesulfonyl chloride (TosCl) under alkaline conditions to generate compound V; ( 4) Compound V reacts with Grignard reagent alkylmagnesium halide in an organic solvent to generate compound I. The chemical properties of the raw materials used in the synthesis method are stable, easy to obtain, and cheap, the synthesis route is short, the yield is high, the total yield reaches more than 55%, and the purity of the target product reaches 99.96%. Overall, the synthesis cost is low, easy to control, and convenient operation, suitable for industrialized mass production.

Description

technical field [0001] The invention relates to the preparation of a liquid crystal monomer material, in particular to a preparation method of a bis-trans cyclohexane type monomer liquid crystal. Background technique [0002] With the development of TN-LCD, STN-LCD and TFT-LCD technology, liquid crystal display technology is more and more widely used in people's production and life, especially the application of TFT-LCD products has brought about a revolution in display technology change. In order to improve the performance of liquid crystal materials, new liquid crystal compounds such as ethane and polyfluorine containing dicyclohexyl have been researched and developed. These compounds have unique properties such as low viscosity and high resistivity, especially the viscosity ratio of the bicyclohexyl system. Other systems have much lower viscosities, so these materials are widely used in liquid crystal displays. [0003] Disclosed in the patent DE332173 is the synthetic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/08C07C13/28C07C1/00
Inventor 史海滨邓友节宋斌
Owner 江苏广域化学有限公司