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Green environment-friendly preparation method of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (TPO)

A technology of trimethylbenzoyl and diphenylphosphine oxide, which is applied in chemical instruments and methods, organic chemistry, compounds of Group 5/15 elements of the periodic table, etc., can solve the problem of high cost of organic oxidants and unfavorable industrial production , environment and product pollution, to achieve the effect of low cost, easy operation and easy operation

Inactive Publication Date: 2017-06-30
SHANDONG UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

This technique has the following disadvantages: 1) the yield is low, the yield of the target product is only 55%, and the cost of the organic oxidant is high; 2) the by-products left in the system after part of the organic oxidant is reduced cause certain problems to the recovery of the product Difficulty; 3) oxidant by-products have caused environmental and product pollution, which is unfavorable for industrialized production
[0005] Patent CN 99813713.8 discloses the synthetic technique of TPO, uses metal lithium, 2,4,6-trimethylbenzoic acid base chlorine and P-chlorobiphenylphosphine etc., with hydrogen peroxide and organic peroxy compound (as peracetic acid or air, pure oxygen) as an oxidant, naphthalene as a catalyst to carry out synthesis at 120 ° C, the method has the advantage of not having to separate intermediate products, but the synthesis steps are many, the cost of raw materials is high, and the yield is low

Method used

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  • Green environment-friendly preparation method of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (TPO)

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add 37.61g of 2,4,6-trimethylbenzaldehyde and 56.17g of diphenylphosphine oxide into a three-necked flask containing 450mL of dichloromethane and stir, and react at room temperature (25°C) for 6 hours, and the precipitated white solid For TPO intermediates. Then put the three-necked bottle into a low-temperature water bath to cool to 8-10°C, and add 0.2309g of vanadium pentoxide (V 2 o 5 ), 37mL H 2 o 2 (mass fraction 30%), reacted at low temperature for 0.5 hours, then placed at room temperature (25° C.) for stirring, and reacted for 3 hours.

[0025] After the reaction, add 5% Na to the three-neck flask 2 S 2 o 3 Aqueous solution neutralizes unreacted H 2 o 2 , to obtain the reaction solution. Then put the reaction solution into a precipitation kettle, separate the water layer, collect the organic layer, wash three times with saturated brine, then add anhydrous sodium sulfate to remove water, then recrystallize, suction filter, and dry to obtain a light yello...

Embodiment 2

[0027] Add 37.61g of 2,4,6-trimethylbenzaldehyde and 56.17g of diphenylphosphine oxide into a three-necked flask containing 450mL of dichloromethane and stir, and react at room temperature for 6 hours. The white solid that precipitates is the TPO intermediate . Then put the three-necked bottle into a low-temperature water bath to cool to 8-10°C, and add 0.4075g of vanadyl sulfate (VOSO 4 ), 37mL H 2 o 2 (30%), reacted at low temperature for 0.5 hours, then put it under normal temperature to stir, and reacted for 4 hours.

[0028] After the reaction, add 5% Na to the three-neck flask 2 S 2 o 3 Aqueous solution neutralizes unreacted H 2 o 2 , to obtain the reaction solution. Then put the reaction solution into a precipitation kettle, separate the water layer, collect the organic layer, wash three times with saturated brine, then add anhydrous sodium sulfate to remove water, then recrystallize, suction filter, and dry to obtain a light yellow powder The solid is the TPO ...

Embodiment 3

[0030] Add 37.61g of 2,4,6-trimethylbenzaldehyde and 56.17g of diphenylphosphine oxide into a three-necked flask with 450mL of dichloromethane and stir for 6 hours, then put the three-necked flask into a low-temperature water bath to cool to 8~10℃, add 0.6126g vanadyl oxalate (VOC 2 o 4 ·5H 2 O), 37mL H 2 o 2 (30%), reacted at low temperature for 0.5 hours, then put it under normal temperature for stirring, and reacted for 5 hours.

[0031] After the reaction, add 5% Na to the filtrate 2 S 2 o 3 Aqueous solution neutralizes unreacted H 2 o 2 , extracted, collected the organic layer, washed three times with saturated brine, then added anhydrous sodium sulfate to remove water, then recrystallized, filtered with suction, and dried to obtain a light yellow powdery solid, which was the TPO product, with a yield of 96%.

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Abstract

The invention discloses a green environment-friendly preparation method of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (TPO). The method comprises the following steps: a. adding 2,4,6-trimethylbenzaldehyde and diphenylphosphine oxide into a dichloromethane-filled three-neck flask, and stirring to react at normal temperature to obtain a TPO intermediate; b. cooling the three-neck flask in a low-temperature water bath to 8-10 DEG C, sequentially adding a vanadium catalyst and an oxidizer hydrogen peroxide into the three-neck flask, stirring to react for 0.5 hour, putting the three-neck flask at normal temperature, and continuing stirring for 3-5 hours; and c. adding a sodium thiosulfate water solution into the three-neck flask, treating to remove the unreacted oxide to obtain a reaction solution, and carrying out separation purification on the reaction solution to obtain the TPO product. The clean environment-friendly H2O2 used as the oxidizer is matched with the vanadium catalyst to constitute the green environment-friendly oxidization system, thereby lowering the production cost, enhancing the product yield, being environment-friendly and being beneficial to implementing commercialized production.

Description

technical field [0001] The invention relates to a synthesis process of monoacylphosphine oxide, in particular to a green and environment-friendly preparation method of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide based on a green oxidation system, which belongs to organic The field of synthetic technology. Background technique [0002] Photocuring technology is a technology that under the irradiation of light (ultraviolet light or visible light), oligomers and active monomers are polymerized, cross-linked and cured under the action of an initiator. Because of its energy saving, environmental protection, economy, high efficiency and wide applicability It has been widely used in coatings, paints, printing inks, biomedical material preparation, 3D printing and other fields. The light source, the curing matrix containing unsaturated bonds and the initiator are the three main factors to achieve photocuring, and the initiator is particularly important. The choice of the initiat...

Claims

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Application Information

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IPC IPC(8): C07F9/53
CPCC07F9/5337
Inventor 于青赵君静王婷婷王忠卫
Owner SHANDONG UNIV OF SCI & TECH
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