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A kind of preparation method of bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide

A technology of trimethylbenzoyl and phenylphosphine oxide, which is applied in the field of preparation of bisphenylphosphine oxide, can solve the problems of increasing by-products, unfavorable safety, failure to recycle, etc., and achieves the reduction of organic matter content and yield reduction. The effect of reducing the efficiency and reducing the process cost

Active Publication Date: 2022-06-21
TIANJIN JIURI NEW MATERIALS CO LTD
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Problems solved by technology

[0004] In the prior art, the preparation method of two (2,4,6-trimethylbenzoyl) phenyl phosphine oxides generally comprises: at first metal sodium and phenyl phosphorus dichloride react, add proton source (alcohols, amine class) dissociation to obtain phenylphosphine hydrogen, phenylphosphine hydrogen reacts with 2.4.6-trimethylbenzoyl chloride under alkaline conditions, and finally oxidizes to obtain the target product. The main problem that this process exists is: dissociation The agent needs more than 2 equivalents, and it cannot be recycled, and a large amount of waste water containing organic matter is produced, and there is phenylphosphine hydrogen in the reaction process, which has a stench and is flammable, and there is a great potential safety hazard;
[0005] CN100436461C discloses a kind of preparation method of acyl phosphine, and preparation method comprises: (1) make organophosphorus halide react with metal sodium in the presence of activator in solvent, wherein metal sodium is in the solvent with the alkali metal particles of average particle size≤500 μm (2) Subsequent reaction with acid halides; in this reaction, chlorobenzene and / or n-butanol are used as activators, but there is still the possibility of producing phenylphosphine hydrogen during its preparation, which is not conducive to The safety of the reaction, at the same time, due to the presence of n-butanol, it will quickly react with the acid halide to form an ester, increasing the by-products and consuming the acid halide, increasing the cost

Method used

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  • A kind of preparation method of bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide
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  • A kind of preparation method of bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide

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Embodiment 1

[0097] The present embodiment provides a preparation method of bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide, comprising:

[0098] (1) In a 500mL four-necked flask, add 11g of sodium metal and 150g of toluene, heat up to 100°C under nitrogen protection, and stir for 3h to beat the sodium metal into sodium sand to obtain a sodium sand suspension;

[0099] (2) keep the reflux state, in step (1), add 21g phenyl phosphine dichloride dropwise to the sodium-sand suspension, add about 2h, keep the reflux for 4h, until the reaction solution turns bright yellow, then under the reflux state 4.2g (0.5eq) of tetrahydrofuran was added, the dripping was completed in about 0.5h, the temperature was kept under reflux for 2h, the temperature was lowered to 70°C under nitrogen protection, 43g mes-trimethylbenzoyl chloride was added dropwise, the reaction temperature was controlled at 75°C, the addition was completed in about 2h, and 75°C was added dropwise. Incubate the reaction at ℃ for 8h...

Embodiment 2

[0104] The present embodiment provides a preparation method of bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide, comprising:

[0105] (1) In a 500mL four-neck flask, add 11g of sodium metal and 150g of toluene, add 4.2g (0.5eq) of tetrahydrofuran, heat up to 100°C under nitrogen protection, and stir for 3h to make sodium metal into sodium sand to obtain a sodium sand suspension ;

[0106] (2) maintain the reflux state, in step (1), add 21 g of phenyl phosphine dichloride dropwise to the sodium-sand suspension, add it for about 2 hours, and keep refluxing for 4 hours until the reaction solution turns bright yellow, and the nitrogen protection is lowered to 70°C, dropwise add 43g mes-trimethylbenzoyl chloride, control the reaction temperature to 75°C, finish the addition in about 2h, and keep the reaction at 75°C for 8h;

[0107] (3) After the reaction in step (2) is completed, add 120 g of water dropwise to the reaction solution, stir at room temperature for 0.5 h, stand for ...

Embodiment 3

[0112] The present embodiment provides a preparation method of bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide, comprising:

[0113] (1) In a 500mL four-neck flask, add 20g of metallic sodium and 150g of toluene, heat up to 100°C under nitrogen protection, and stir the sodium for 2h to make sodium sand to obtain a sodium sand suspension;

[0114] (2) keep the reflux state, add 21 g of phenylphosphine dichloride dropwise to the sodium-sand suspension, add it for about 2 h, keep it at reflux for 6 h, until the reaction solution becomes bright yellow, add 1.7 g of tetrahydrofuran (0.2 g of tetrahydrofuran (0.2 g) under reflux conditions eq), after dropping for about 0.5h, the temperature was kept under reflux for 4h, the temperature was lowered to 70°C under nitrogen protection, 43g of mesityl benzoyl chloride was added dropwise, the reaction temperature was controlled at 70°C, the addition was completed for about 2h, and the reaction was kept at 70°C for 10h;

[0115] (3) afte...

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Abstract

The invention provides a kind of preparation method of bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide, in the preparation method, add specific Ether compounds are used as complexing agents, and the addition of complexing agents can effectively inhibit the formation of phenylphosphine sodium polyphosphides, promote the formation of phenylphosphine sodium, and do not need to go through the phenylphosphine hydrogen process, which reduces the process cost and improves the production efficiency. The safety of the process; in addition, the above-mentioned complexing agent is a polar aprotic solvent with a small amount. Compared with the traditional method using a protic solvent as an activator or a proton source, it can reduce the content of organic matter in wastewater and has Certain environmental benefits and cost savings.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to a preparation method of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide. Background technique [0002] Acylphosphine oxide compounds are used as efficient photoinitiators for initiating the radiation polymerization of some unsaturated resins under UV light irradiation, especially for white formulations and glass fiber reinforced polyester / styrene systems and with light stabilizers Compatible with varnish systems and paint systems for outdoor use, such as for wood, paper, metal, plastic, optical fiber, as well as printing inks and pre-impregnated systems. [0003] Among them, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (initiator 819) and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide (initiator TPO) Two of them are widely used and widely used. [0004] In the prior art, the preparation method of bis(2,4,6-trimethylbenzoyl) phenylphosphine oxide generally includes: first, r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6568
CPCC07F9/65685
Inventor 赵国锋张齐毛桂红张建锋武瑞
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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