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Production of 1,4-bis(O-styryl)

A technology of cyanostyrene and o-cyanobenzyl, applied in 1 field, can solve the problems of low product purity and yield, cumbersome operation, high energy consumption, etc., and achieve the effects of simple operation, low energy consumption, energy consumption and environmental protection

Inactive Publication Date: 2006-08-16
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The object of the present invention is to provide a kind of preparation method of 1,4-bis(o-cyano styryl) benzene which is energy-saving, environment-friendly, high in product purity and yield and simple in operation and easy to mass-produce, and overcomes existing The technology has defects such as high energy consumption, non-environmental protection, low product purity and yield, and cumbersome operation.

Method used

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  • Production of 1,4-bis(O-styryl)
  • Production of 1,4-bis(O-styryl)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 16g of commercially available o-cyanobenzyl chloride (99wt%) into a 250mL four-neck flask with a condenser, stir and heat up to 100°C, add 13g of trimethyl phosphite (98wt%) within 2.5 hours After the addition, the temperature was raised to 130°C, and the stirring reaction was continued for 2 hours to remove the methyl chloride gas, then the reaction liquid was cooled to 28°C, and 6.3g of terephthalaldehyde and 10g of N,N-dimethylformamide (DMF) were added, Stir evenly, add 54g of sodium ethylate ethanol solution (16wt%) dropwise within two hours at a temperature of 30°C, react for 2 hours, filter to obtain the crude product, then wash with ethanol and water in turn, filter and dry to obtain yellow-green crystals The product has a melting point of 230-231° C. and a reaction yield of 87%.

Embodiment 2

[0024] Add 62g of commercially available o-cyanobenzyl chloride (99wt%) into a 500mL four-neck flask with a condenser, stir and heat up to 110°C, add 51g trimethyl phosphite (98wt%) within 2.5 hours After the addition, the temperature was raised to 120°C, and the stirring reaction was continued for 3 hours to remove the methyl chloride gas, then the reaction solution was cooled to 20°C, 25g of terephthalaldehyde and 50g of DMF were added, and 215g of sodium ethylate ethanolic solution was added dropwise within two hours ( 10wt%), the reaction time was continued for 2 hours, the crude product was obtained by filtration, washed with ethanol and water, and dried to obtain a yellow-green crystalline product with a melting point of 229-231° C. and a yield of 82%.

Embodiment 3

[0026] According to the feeding ratio and method of Example 2, 50 g of dimethylformamide solvent was changed to 50 g of tetrahydrofuran. The crude product was washed with ethanol and water, and dried to obtain a yellow-green crystal product with a melting point of 228-230° C. and a yield of 73%.

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Abstract

Production of 1,4-diphe(ortho-cyano phenylethylene) is carried out by putting ortho-cyano benzyl chloride into closed reactor with condensing refluxing device at normal pressure, agitating at 100~110DEG C for 2~3hrs, adding into trimethyl phosphite in proportion of ortho-cyano benzyl chloride: trimethyl phosphite=1:1, heating to 120~130DEG C while reacting for 2~3hrs, cooling reactant to 20~30DEG C, adding into terephthalic aldehyde and solvent in proportion of terephthalic aldehyde: ortho-cyano benzyl chloride=1:2mol, dripping into sodium ethylate alcohol solution with concentration 10~16wt%, in 2~3hrs, reacting, filtering to obtain reactant after 2hrs, washing by alcohol and water separately and drying to obtain final product. It is simple and safe, has less consumption and more yields.

Description

technical field [0001] The present invention relates to a kind of preparation method of 1,4-bis (o-cyano styryl) benzene, specifically, relate to a kind of with o-cyano benzyl chloride as raw material, successively with trimethyl phosphite and p-benzene A method for preparing 1,4-bis(o-cyano-styryl)benzene by condensation of diformaldehyde. Background technique [0002] Distyrylbenzene derivatives have many varieties of fluorescent dyes, good whitening effect, pure shade, suitable for various whitening processes, and occupy a very important position in fluorescent whitening agents. The representative one is: 1,4-bis(o-cyanostyrene) benzene, which has good solubility in most organic solvents, is stable to cationic softeners, and can be mixed with sodium hypochlorite, hydrogen peroxide and reducing Use bleach with bath. It can be used for whitening polyester, acetate fiber, nylon, etc., with light fastness of 5 grades and excellent washing fastness; in the application of pol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/51
Inventor 薛为岚许新刚曾作祥陈健康郁伟明
Owner EAST CHINA UNIV OF SCI & TECH
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