Preparation method of cyclohexyl fluorine-containing cyanophenyl derivative liquid crystalline monomer

A technology of fluorine-containing benzonitrile and liquid crystal monomers, which is applied in the preparation of organic compounds, carboxylic acid nitriles, and liquid crystal materials. It can solve the problems of cumbersome operations, high safety risks, and high production costs, and achieve shortened reaction routes and high activity. High, short response time effect

Active Publication Date: 2017-01-11
VALIANT CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The present invention uses 2,6-difluoro-4-bromoxynil or 2-fluoro-4-bromoxynil as raw materials, reacts with cyclohexyl ketone compounds through metallization reaction, and then dehydrates and hydrogenates to prepare this kind of Liquid crystal monomer solves the shortcomings of high safety risk, cumbersome operation and high production cost in industrial production. Compared with the existing technology, the production is simple, safe and economical, and it is more conducive to industrial production

Method used

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  • Preparation method of cyclohexyl fluorine-containing cyanophenyl derivative liquid crystalline monomer
  • Preparation method of cyclohexyl fluorine-containing cyanophenyl derivative liquid crystalline monomer
  • Preparation method of cyclohexyl fluorine-containing cyanophenyl derivative liquid crystalline monomer

Examples

Experimental program
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Effect test

Embodiment 1

[0045] When n=1, R 1 is n-propyl, X is F atom, Y is H atom, and compound IV is 2-fluoro-4-(4'-propyl-bicyclohexyl)-benzonitrile

[0046] (1) In a 2000mL three-necked bottle, add 199g (1.0mol) 2-fluoro-4-bromobenzonitrile, then add 900g tetrahydrofuran, mix well, add 222g (1.0mol) 4-propyl bicyclohexyl ketone, in At a temperature of -60°C to -70°C, add 400mL (1.0mol) of n-butyllithium solution (2.5mol / L) dropwise. 300g of glacial acetic acid with a mass fraction of 20% was hydrolyzed, the hydrolyzed layers were separated, and after the organic phase was washed and neutralized, tetrahydrofuran was removed to obtain 304.2g of light yellow liquid 2-fluoro-4-(4-hydroxyl-4'-propyl-bicyclic Hexyl)-benzonitrile, the yield is 88.7%;

[0047] (2) Add 304.2 g (0.887 mol) of 2-fluoro-4-(4-hydroxyl 4'-propyl-bicyclohexyl)-benzonitrile obtained in step (1) into a 2000 mL three-necked flask, and then add 912.6 g toluene and 30.6g (0.1774mol) p-toluenesulfonic acid, at a temperature of 110...

Embodiment 2

[0050] When n=0, R 1 is n-propyl, X is an F atom, Y is an H atom, and compound IV is 2-fluoro-4-(4'-propyl-cyclohexyl)-benzonitrile

[0051] (1) In a 2000mL three-necked bottle, add 199g (1.0mol) 2-fluoro-4-bromobenzonitrile, then add 900g tetrahydrofuran, mix well, add 140g 4-propyl cyclohexanone (1.0mol), in At a temperature of -60°C to -70°C, add 400mL (1.0mol) of n-butyllithium solution (2.5mol / L) dropwise, and after the dropwise addition is completed and kept warm for 2-3 hours, the metallization reaction is carried out, and the reaction is completed. Pour 300g of glacial acetic acid with a mass fraction of 20% for hydrolysis, hydrolyze and separate layers, wash the organic phase with water to neutralize, and remove tetrahydrofuran to obtain 235.1g of light yellow liquid 2-fluoro-4-(1-hydroxyl-4'-propyl -cyclohexyl)-benzonitrile, the yield is 90.0%;

[0052] (2) Add 235.1g (0.9mol) of 2-fluoro-4-(1-hydroxy-4'-propyl-cyclohexyl)-benzonitrile obtained in step (1) into a 2...

Embodiment 3

[0055] When n=1, R 1 is pentyl, X is F atom, Y is F atom, compound IV is 2,6-difluoro-4-(4'-pentyl-bicyclohexyl)-benzonitrile

[0056] (1) Into a 2000mL three-necked bottle, add 108.5g (0.5mol) 2,6-difluoro-4-bromobenzonitrile, then add 545g tetrahydrofuran, mix well, add 125g (0.5mol) 4-pentylbicyclo For hexyl ketone, add 200mL (0.5mol) of n-butyllithium solution (2.5mol / L) dropwise at a temperature of -60°C to -70°C. , after the reaction is complete, pour 150g of glacial acetic acid with a mass fraction of 20% for hydrolysis, hydrolysis and layering, and after the organic phase is washed with water to neutrality, 174.1g of 2,6-difluoro-4-(4-hydroxy- 4'-pentyl-bicyclohexyl)-benzonitrile, the yield was 89.5%;

[0057] (2) Add 174.1 g (0.45 mol) of 2,6-difluoro-4-(4-hydroxy-4'-pentyl-bicyclohexyl)-benzonitrile obtained in step (1) into a 2000 mL three-necked flask , then add 522.3g toluene and 15.6g (0.09mol) p-toluenesulfonic acid, at 110°C, reflux and separate water to kee...

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Abstract

The invention discloses a preparation method of a cyclohexyl fluorine-containing cyanophenyl derivative liquid crystalline monomer, belonging to the technical field of liquid crystal display. The structural general formula of the liquid crystalline monomer is as shown in the description, wherein R1 represents C1-C5 linear chain alkyl, n is equal to 0 or 1, X and Y represent F or H atom, and at least one of X and Y represents the F atom. The preparation method comprises the steps of carrying out metallization reaction and cyclohexyl ketone compound reaction on the raw material, namely 2,6-difluoro-4-bromoxynil or 2-fluoro-4-bromoxynil, and carrying out dehydration and hydrogenation, so as to obtain the liquid crystalline monomer. The preparation method has the beneficial effects that the process route is simple, reaction conditions are mild, and the production cost is lowered; and the preparation method is beneficial to large-scale production and has a very good application prospect.

Description

technical field [0001] The invention relates to a preparation method of a cyclohexyl fluorine-containing benzonitrile derivative liquid crystal monomer, belonging to the technical field of liquid crystal display. Background technique [0002] With the development of super twisted nematic liquid crystal (STN-LCD) and thin film transistor array driven liquid crystal display (TFT-LCD) technology, liquid crystal display technology is more and more widely used in people's production and life, especially TFT-LCD The application of the product has brought about a revolutionary change in display technology. Although there have been many reports on liquid crystal materials, not all of them are suitable for use in display devices, because liquid crystal materials for display must meet a wide operating temperature range, low operating voltage, low viscosity, fast response, and high resistance. Rate, moderate dielectric anisotropy and other characteristics. [0003] In order to improv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/50C09K19/30
CPCC07C253/30C07C255/50C07C255/53C09K19/3003C09K2019/301
Inventor 王磊朱世乾侯菲菲申川生吕东泽张云
Owner VALIANT CO LTD
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