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Method for producing cyclohexyl group olefin hydrocarbon liquid crystal material

A cyclohexyl olefin and cyclohexyl technology, applied in the direction of liquid crystal materials, chemical instruments and methods, hydrocarbons, etc., can solve the problems of easy structural conversion, pollution, serious pollution, etc., achieve small optical anisotropy and wide application Prospect, effect of simple preparation method

Active Publication Date: 2008-08-20
内蒙古永太化学有限公司
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Problems solved by technology

[0010] 4-Substituted cyclohexanone as raw material, reacts with chloromethyl methyl ether triphenyl phosphonium salt and tert-butoxide potassium to synthesize cis-trans 4-substituted cyclohexyl formaldehyde, using chloromethyl methyl ether triphenyl quaternary Phosphine salt reagent, which is prepared by the reaction of chloromethyl methyl ether and triphenylphosphine, wherein chloromethyl methyl ether is highly toxic, irritating, seriously polluting, and requires high purity, especially the prepared chloromethyl methyl ether The quality stability of ether triphenyl phosphonium salt is poor, and the purity of chloromethyl methyl ether triphenyl phosphonium salt seriously affects the yield of producing 4-substituted cyclohexyl formaldehyde, and the reaction is not easy to control
At the same time, the 4-substituted cyclohexyl formaldehyde prepared by the above reaction is a cis-trans compound. It is necessary to convert the 4-substituted cyclohexyl formaldehyde cis structure into a trans structure, and the structural conversion reaction is a chemical equilibrium reaction, and it is impossible to completely convert it into a trans structure. Formula structure, so the obtained trans-4-substituted cyclohexyl carboxaldehyde also contains part of the cis-4-substituted cyclohexyl carboxaldehyde of the cis structure. When purified by recrystallization, structural conversion is easy to occur, and it is difficult to obtain extremely high purity trans-4-substituted cyclohexylcarbaldehyde
Therefore this synthetic route obtains the low yield of trans-4-substituted cyclohexyl olefin, high cost, serious pollution, and difficult control of chemical synthesis reaction

Method used

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  • Method for producing cyclohexyl group olefin hydrocarbon liquid crystal material
  • Method for producing cyclohexyl group olefin hydrocarbon liquid crystal material
  • Method for producing cyclohexyl group olefin hydrocarbon liquid crystal material

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Embodiment 1, preparation trans, trans-4-(4-propylcyclohexyl) cyclohexylethylene

[0046] 1. Preparation of trans, trans-4-(4-propylcyclohexyl) cyclohexylcarbonyl chloride

[0047] In the reflux condenser with drying tube, in a 250mL three-necked flask, add trans, trans-4-(4-propylcyclohexyl)cyclohexyl formic acid (0.1mol), thionyl chloride (0.15mol), benzene ( 100 mL), stirred and refluxed for 10 hours. The reaction mixture was rotary evaporated to remove the solvent, and the solvent and thionyl chloride were spin-dried as much as possible, and sealed for later use.

[0048] 2. Preparation of trans, trans-4-(4-propylcyclohexyl)cyclohexylcarbaldehyde

[0049] In a 500ml three-necked flask, add trans, trans-4-(4-propylcyclohexyl)cyclohexylcarbonyl chloride and 200mlTHF prepared in the previous step, under nitrogen protection, add 2.8g Pd / C (5%), under nitrogen protection , Add 35g (0.3mol) triethylsilane at -5°C in one go, and the reaction takes about 1 hour. The cat...

Embodiment 2

[0056] Embodiment 2, preparation trans, trans-4-[4-(4-methylphenyl) cyclohexyl] cyclohexylethylene

[0057] 1. Preparation of trans, trans-4-[4-(4-methylphenyl)cyclohexyl]cyclohexylcarbonyl chloride

[0058] Trans, trans-4-[4-(4-methylphenyl)cyclohexyl]cyclohexylcarboxylic acid (0.1mol), thionyl chloride (0.15mol), benzene (100mL), the preparation method is the same as in Example 1 .

[0059] 2. Preparation of trans, trans-4-[4-(4-methylphenyl)cyclohexyl]cyclohexylcarbaldehyde

[0060] In a 500ml three-necked flask, add trans, trans-4-[4-(4-methylphenyl)cyclohexyl]cyclohexylcarbonyl chloride and 200ml dioxane prepared in the previous step, and add 2.8g Pd / C (10%), under the protection of nitrogen, add 35g (0.3mol) triethylsilane at 20°C in one batch, and the reaction takes about 1 hour. The catalyst was removed by filtration, petroleum ether was recrystallized to obtain 19.5 g of white solid, the purity of aldehyde was 98.5% (GC), the yield was 85%, DSC: C117N151I.

[006...

Embodiment 3

[0067] Example 3, trans, trans-4-[4-(3,4-difluorophenyl) cyclohexyl] cyclohexylethylene

[0068] 1. Preparation of trans, trans-4-[4-(3,4-difluorophenyl) cyclohexyl] cyclohexyl formyl chloride

[0069] Trans, trans-4-[4-(3,4-difluorophenyl)cyclohexyl]cyclohexylcarboxylic acid (0.1mol), thionyl chloride (0.15mol), benzene (100mL), the preparation method is the same as the implementation example 1.

[0070] 2. Preparation of trans, trans-4-[4-(3,4-difluorophenyl)cyclohexyl]cyclohexylcarbaldehyde

[0071] In a 500ml three-necked flask, add trans, trans-4-[4-(3,4-difluorophenyl)cyclohexyl]cyclohexylcarbonyl chloride and 200ml dichloromethane prepared in the previous step, under nitrogen protection, add 3.2g Pd / C (10%), under the protection of nitrogen, 35 g (0.3 mol) triethylsilane was added at 25° C. at one time, and the reaction took about 1.5 hours. The catalyst was removed by filtration, petroleum ether was recrystallized to obtain 25 g of white solid, the purity of aldehyd...

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Abstract

The invention discloses a preparation method of trans-4-replacing cyclohexyl formaldehyde and trans-4-replacing cyclohexyl olefin, which uses trans-4-replacing cyclohexyl formic acid as raw material, and prepares the trans-4-cyclohexyl olefin by acyl chloride, silicon hydrogen alkane reduction, and reaction with methyl bromide triphenylphosphine quarter phosphonium. The preparation method of the trans-4-replacing cyclohexyl formaldehyde and the trans-4-replacing cyclohexyl olefin is simple in method, clean in using, and has wide application prospect.

Description

technical field [0001] The invention relates to a preparation method of trans-4-substituted cyclohexylcarbaldehyde and trans-4-substituted cyclohexylalkene. 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 sexual change. At present, one of the main development directions of liquid crystal display technology is to improve the response speed and realize the fast response of dynamic images, such as liquid crystal display devices such as 3G mobile phones, computers and LCD TVs. In order to improve the response speed, reducing the viscosity of mixed liquid crystals has become the main direction for the development of liquid crystal materials. [0003] The trans-4-substituted cyclohexyl olefin liquid crystal compound has excellent properties ...

Claims

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Application Information

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IPC IPC(8): C07C13/28C07C1/207C09K19/30
Inventor 何人宝钟建新王莺妹章正秋
Owner 内蒙古永太化学有限公司
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