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A kind of preparation method of ultraviolet photoinitiator p-dimethylaminobenzoate compound

A technology of dimethylaminobenzoic acid and ester compounds, which is applied in the field of preparation of p-dimethylaminobenzoic acid ester compounds as an ultraviolet photoinitiator, and can solve the problems of unfriendly environment, high production cost and low esterification yield , to achieve the effect of reducing production cost, less risk, and simple operation

Active Publication Date: 2015-07-29
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The problem of method 1) is that the yield of esterification is low, resulting in high production costs, and it also produces a large amount of acidic wastewater, which is not environmentally friendly; the disadvantage of method 2) is that nitrogen methylation is difficult to complete, and dimethyl sulfate More toxic, more wastewater, methyl iodide and sodium cyanoborohydride are highly toxic and costly; method 3) avoids the use of more toxic reagents, and does not produce acidic wastewater, but uses expensive noble metal compounds, four ( Triphenylphosphine) palladium and benzyl bromide catalyst or indazolium salt catalyst, the cost of the catalyst is high and the amount used is large, so the overall cost is very high, and it is not suitable for industrial production

Method used

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  • A kind of preparation method of ultraviolet photoinitiator p-dimethylaminobenzoate compound
  • A kind of preparation method of ultraviolet photoinitiator p-dimethylaminobenzoate compound
  • A kind of preparation method of ultraviolet photoinitiator p-dimethylaminobenzoate compound

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Embodiment 1

[0027] Embodiment 1: the preparation of methyl p-dimethylaminobenzoate

[0028] In a 500ml four-necked bottle, add 250ml methanol, 7g ferric perchlorate hexahydrate, and 53.0g p-dimethylaminobenzaldehyde. Cool the reaction to about -5°C, add 43ml of 33% hydrogen peroxide dropwise to the reaction, and the dropwise addition is completed in about 1 hour. After the dropwise addition is completed, slowly rise to room temperature for 3 hours. TLC or GC monitors the reaction end point. After the reaction is complete, the methanol is recovered by distillation under normal pressure and then under reduced pressure. The residue is rectified under reduced pressure to obtain 58 g of the product (conditions for collecting fractions: 101-105 °C / 0.05 mm Hg), and the yield is 91.0 %, purity 99.2%.

Embodiment 2

[0029] Embodiment 2: the preparation of methyl p-dimethylaminobenzoate

[0030] In a 500ml four-neck flask, add 250ml methanol, 10g ferric perchlorate hexahydrate, and 53.0g p-dimethylaminobenzaldehyde. Cool the reaction to about -5°C, add 43ml of 33% hydrogen peroxide dropwise to the reaction, and the dropwise addition is completed in about 1 hour. After the dropwise addition is completed, slowly rise to room temperature for 3 hours. TLC or GC monitors the end point of the reaction. After the reaction is complete, methanol is recovered by distillation under normal pressure and then under reduced pressure. The residue is rectified under reduced pressure to obtain 57.1 g of the product (conditions for collecting fractions: 101-105 °C / 0.05 mm Hg). 90.5%, purity 99.4%.

Embodiment 3

[0031] Embodiment 3: the preparation of ethyl p-dimethylaminobenzoate

[0032] In a 500ml four-necked bottle, add 300ml ethanol, 7g ferric perchlorate hexahydrate, and 53.0g p-dimethylaminobenzaldehyde. Cool the reaction to about -5°C, add 43ml of 33% hydrogen peroxide dropwise to the reaction, and the dropwise addition is completed in about 1 hour. After the dropwise addition is completed, slowly rise to room temperature for 3 hours. TLC or GC monitors the end point of the reaction. After the reaction is complete, the solvent is recovered by distillation under normal pressure and then under reduced pressure. The residue is rectified under reduced pressure to obtain 64.2g of the product (conditions for collecting fractions: 110~115°C / 0.02mm Hg), the yield 93.5%, purity 99.3%.

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Abstract

The invention relates to a preparation method for p-dimethylamino methyl benzoate, p-dimethylamino ethyl benzoate (EBD), p-dimethylamino isoamyl benzoate (DMBI) and p-dimethylamino benzoic di-iso-octyl sebacate (EHA) compounds of an ultraviolet initiating agent. P-dimethylamino benzaldehyde serving as a raw material reacts with alkyl alcohol and hydrogen peroxide under catalysis of ferric perchlorate to obtain corresponding p-dimethylamino benzoate compounds; the purity of a product is higher than or equal to 99 percent. The preparation method disclosed by the invention has the advantages that the raw materials are low in cost and readily available; the reaction conditions are mild and are easy to operate; the purity is high, the yield is high, the amount of three wastes is small; the preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and specifically relates to an ultraviolet photoinitiator methyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate (EDB), isoamyl p-dimethylaminobenzoate (DMBI), The preparation method of the isooctyl p-dimethylaminobenzoate (EHA) similar compound uses p-dimethylaminobenzaldehyde as a raw material, under the catalysis of ferric perchlorate, reacts with alcohol and hydrogen peroxide to obtain the corresponding p-dimethylaminobenzoic acid Preparation method of ester compound. Background technique [0002] P-dimethylaminobenzoate series compounds are a kind of high-efficiency amine accelerators, used together with free radical (II) type photoinitiators, and are widely used in varnish coating systems on paper, wood, metal and plastic surfaces, Ink, adhesive and other aspects of UV curing. It can also be used for the ultraviolet radiation polymerization of single or multiple monomers,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/60C07C227/02
Inventor 赵国锋白振锋张齐马小文武瑞刘艳丽吕振波李可
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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