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Method for synthesizing ultraviolet photoinitiator of p-dimethylamin benzoic ether compounds

A technology of dimethylaminobenzoic acid and ester compounds, which is applied in the field of synthesis of p-dimethylaminobenzoic acid ester compounds as an ultraviolet photoinitiator, and can solve problems such as low esterification yield, affecting yield, and large amount of acidic wastewater. problem, to achieve the effect of moderate length of synthetic route, solvent recovery and application, and environmental friendliness

Active Publication Date: 2010-10-20
INSIGHT FINECHEM
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  • Application Information

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Problems solved by technology

Method (1) exists that p-dimethylaminobenzoic acid cost is more expensive, and esterification yield is low, and the shortcomings such as acid waste water amount are big
Method (II) exists that nitrogen methylation is difficult to complete, the methylation reagent dimethyl sulfate used is highly toxic, and the amount of acidic wastewater is large; the cost of using methyl chloride and methyl iodide is high, and both of them have esters in the methylation process. There are some disadvantages such as partial hydrolysis and affecting the yield

Method used

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  • Method for synthesizing ultraviolet photoinitiator of p-dimethylamin benzoic ether compounds
  • Method for synthesizing ultraviolet photoinitiator of p-dimethylamin benzoic ether compounds
  • Method for synthesizing ultraviolet photoinitiator of p-dimethylamin benzoic ether compounds

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Embodiment 1

[0030] step one:

[0031] (1) Preparation of p-dimethylaminobenzonitrile

[0032] In a 1L autoclave, add 74.0g (0.5mol) p-nitrobenzonitrile, 100ml methanol, 90g formaldehyde (wt 40%) and 10g concentrated sulfuric acid, then add 3.7g Pd / C (wt 5%) to seal the reaction The system was replaced with nitrogen and hydrogen 3 times successively. After stirring for 15 minutes, the temperature was raised to 60°C. Hydrogen was passed through to maintain the hydrogen pressure at 0.5MPa. The hydrogen absorption rate was regularly measured. When no hydrogen was absorbed for 30 minutes, the reaction was stopped. Cool to room temperature and release the pressure, filter the reaction solution to recover Pd / C, neutralize to neutral with 20% aqueous sodium bicarbonate solution, add 150ml of toluene for extraction, stand to separate the organic layer, and recover the solvent by distillation under reduced pressure, the obtained crude product is further 65.7g of the product was obtained by rectifi...

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Abstract

The invention relates to a method for synthesizing an ultraviolet photoinitiator of p-dimethylamin benzoic ether compounds of ethyl p-dimethylaminobenzoate (EDB), isoamyl p-dimethylaminobenzoate (IADB) and isooctyl p-dimethylaminobenzoate (EHA, trade name thereof is 507) and a production process thereof. The method comprises the following steps of: performing nitro reduction reaction and nitrogenmethylation reaction by using nitrobenzonitrile as a raw material to obtain p-dimethylamino cyanophenyl; reacting the cyanophenyl with a Vilsmeier reagent to generate an intermediate; and performing hydrolyzation in an alkyl alcohol / water / hydrogen chloride (HCl) system to obtain the corresponding p-dimethylamin benzoic ether compounds, wherein the purity of the product is over 98 percent and the total yield is over 80 percent. The synthesizing method has the characteristics of mild reaction condition, simple operation, environmental friendliness, easy recovery and application of solvent and suitability for industrial production.

Description

field of invention [0001] The present invention relates to ultraviolet photoinitiator ethyl p-dimethylaminobenzoate (EDB), isopentyl p-dimethylaminobenzoate (IADB) and isooctyl p-dimethylaminobenzoate (EHA, trade name is 507) and Synthesis method and production process of similar compounds. The method of the present invention is to take p-nitrobenzonitrile as raw material, through nitro reduction, aminomethylation reaction, obtains p-dimethylaminobenzonitrile, this benzonitrile reacts with Vilsmeier reagent to generate intermediate, finally in alkyl alcohol / The corresponding p-dimethylaminobenzoate compounds are obtained by hydrolysis in the water / HCl system, the product purity is greater than 98%, and the total yield is more than 80%. The synthesis method of the invention has the characteristics of no harsh conditions, simple operation, environmental friendliness, and easy recycling of solvents, and is suitable for industrial production. Background of the invention [00...

Claims

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Application Information

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IPC IPC(8): C07C227/26C07C229/60
Inventor 李永芳王先文陈文王中奎
Owner INSIGHT FINECHEM
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