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Preparation method for benzoyldiphenyl phosphine oxide derivatives

A technology of benzoyl diphenyl and diphenyl phosphine oxide, which is applied in the field of polymers, can solve the problems of low yield and achieve the effects of increasing yield, reducing waste, and reducing reaction steps

Active Publication Date: 2015-12-30
QINGDAO FUSILIN CHEM SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing production method generally has the problem of low yield, such as Chinese patent CN1486986A using PhPCl 2 As a raw material, first react with an active metal [M] to obtain an active intermediate PhP [M] 2 , and in turn with R 1 COCl, RX reaction, oxidation to produce monoacyl phosphine oxide
After the patent improves the existing technology, the yield is only increased to about 70%.

Method used

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  • Preparation method for benzoyldiphenyl phosphine oxide derivatives
  • Preparation method for benzoyldiphenyl phosphine oxide derivatives
  • Preparation method for benzoyldiphenyl phosphine oxide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Preparation of 2,4,6-trimethylbenzoyldiphenylphosphine oxide (TPO)

[0083] Introduce nitrogen into the reaction kettle to remove the air, add 20.2g (0.1mol) diphenylphosphine oxide, 30.3g (23mL) dichloromethane and 0.56g (0.010mol) KOH, stir, filter with suction, at room temperature Add to 34.10g (0.11mol) of 2,4,6-trimethylbenzoic anhydride organic solvent, the organic solvent is 40g of dichloromethane, after the addition, reflux at 80°C for 20h. The light yellow liquid was obtained by filtration, and then recrystallized with benzene to obtain 27.86 g of light yellow crystalline powder with a yield of 80% and a purity of 99%.

[0084] The reaction mechanism of the present embodiment is:

[0085]

[0086] The present invention also carried out nuclear magnetic and infrared characterizations of the TPO obtained in this embodiment, and the characterization results are as follows: figure 1 , figure 1 with image 3 as shown, figure 1 For the TPO that the embodiment...

Embodiment 2

[0089] Preparation of Benzoyldiphenylphosphine Oxide

[0090] Introduce nitrogen into the reaction kettle to remove air, add 20.20g (0.1mol) diphenylphosphine oxide, 30.3g (23mL) dichloromethane and 0.62g (0.011mol) KOH, stir, and add dropwise to In the organic solvent of 24.86g (0.11mol) of benzoic anhydride, the organic solvent is 35g of dichloromethane, and after the addition is completed, the reaction is refluxed at 70°C for 20h. The light yellow liquid was obtained by filtration, and then recrystallized with petroleum ether to obtain 25.27 g of light yellow crystalline powder with a yield of 85% and a purity of more than 99%.

[0091] The product of this example was detected according to the characterization method in Example 1, and it was proved that the product obtained in this example was the target product benzoyldiphenylphosphine oxide.

Embodiment 3

[0093] Preparation of p-toluyldiphenylphosphine oxide

[0094] Introduce nitrogen into the reaction kettle to remove the air, add 20.2g (0.1mol) diphenylphosphine oxide, 30.3g (23mL) dichloromethane and 0.67g (0.012mol) KOH, stir, filter with suction, and Add to 27.94g (0.11mol) of p-toluic anhydride organic solvent, the organic solvent is 37g of toluene, after the addition, reflux at 75°C for 20h, filter to obtain a light yellow liquid, and then use petroleum ether for recrystallization , to obtain 26.72g of light yellow crystalline powder with a yield of 85% and a purity of 99%.

[0095] The product of this example was detected according to the characterization method in Example 1, and it was proved that the product obtained in this example was the target product p-toluyldiphenylphosphine oxide.

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Abstract

A provided preparation method for benzoyldiphenyl phosphine oxide derivatives comprises the following steps: mixing a diphenylphosphine oxide derivative, a first solvent and a catalyst under an oxygen-free condition, so as to obtain a first reaction solution; dissolving a benzoic anhydride derivative in a second solvent, so as to obtain a second reaction solution; and mixing the first reaction solution and the second reaction solution to perform a nucleophilic reaction, so as to obtain the corresponding benzoyldiphenyl phosphine oxide derivative with the structure shown as a formula I. The provided preparation method for the benzoyldiphenyl phosphine oxide derivatives employs a one-step reaction, reaction steps are reduced, and further waste caused by incapability of 100% utilizing the raw materials and intermediates in the multiple reaction steps is reduced, and the yield of the final product is increased. Raw material waste reduction during reaction and selection on reaction conditions enable the yield of the preparation method is substantially improved, and the yield is between 80%-91%.

Description

technical field [0001] The invention relates to the technical field of polymers, in particular to a preparation method of benzoyl diphenylphosphine oxide derivatives. Background technique [0002] Benzoyl diphenylphosphine oxide compounds are an important class of photoinitiators, widely used in various coatings, especially in the preparation process of screen printing ink, lithographic printing, flexo printing ink, and wood coating. [0003] At present, the industrial method for preparing benzoyldiphenylphosphine oxide compounds generally adopts the synthesis of metal sodium or metal lithium, chlorinated biphenylphosphine and acid chloride as raw materials. However, the existing production method generally has the problem of low yield, such as Chinese patent CN1486986A using PhPCl 2 As a raw material, first react with an active metal [M] to obtain an active intermediate PhP [M] 2 , and in turn with R 1 COCl, RX reaction, after oxidation, the monoacyl phosphine oxide is p...

Claims

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Application Information

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IPC IPC(8): C07F9/53
Inventor 侯计金何伟段好东王忠卫吴邦元
Owner QINGDAO FUSILIN CHEM SCI & TECH
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