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Preparation method of bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide

A technology of trimethylbenzoyl and phenyl phosphine oxide, which is applied in the field of preparation of bisphenyl phosphine oxide, can solve problems such as unfavorable safety, inability to recover, increase by-products, etc., and achieve better inhibition effect.

Active Publication Date: 2021-01-01
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Abstract
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  • Claims
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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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  • Preparation method of bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide

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Embodiment 1

[0097] This embodiment provides a preparation method of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, comprising:

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

[0099] (2) Keep the reflux state, add 21g of phenylphosphine dichloride dropwise to the sodium sand suspension in step (1), add it in about 2h, keep it warm and reflux for 4h, until the reaction solution becomes bright yellow, then in the reflux state Add 4.2g (0.5eq) tetrahydrofuran, drop it for about 0.5h, keep it warm and reflux for 2h, lower the temperature to 70°C under the protection of nitrogen, add 43g of m-trimethylbenzoyl chloride dropwise, control the reaction temperature at 75°C, and finish adding in about 2h, 75 ℃ heat preservation reaction for 8h;

[0100] (3) After the reaction in step (2) ends, add 120g of wa...

Embodiment 2

[0104] This embodiment provides a preparation method of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, comprising:

[0105] (1) In a 500mL four-necked bottle, 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 3 hours to beat the sodium metal into sodium sand to obtain a sodium sand suspension ;

[0106] (2) Keep the reflux state, add dropwise 21g phenylphosphine dichloride in the sodium sand suspension in step (1), add about 2h, insulate and reflux for 4h, until the reaction solution becomes bright yellow, nitrogen protection lowers the temperature to At 70°C, add 43g of mesitylene benzoyl chloride dropwise, control the reaction temperature at 75°C, finish adding in about 2 hours, and keep the reaction at 75°C for 8 hours;

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

Embodiment 3

[0112] This embodiment provides a preparation method of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, comprising:

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

[0114] (2) Keep the reflux state, add 21g of phenylphosphine dichloride dropwise to the sodium sand suspension, add about 2h, keep warm and reflux for 6h, until the reaction solution turns bright yellow, add 1.7g of tetrahydrofuran (0.2 eq), about 0.5h after dripping, heat preservation and reflux for 4h, under nitrogen protection, lower the temperature to 70°C, add 43g of mesitylene benzoyl chloride dropwise, control the reaction temperature at 70°C, finish adding about 2h, and keep the temperature at 70°C for 10h;

[0115] (3) After the reaction finishes, 120g of water is added dropwise to the reaction solution, stirred at room tempe...

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Abstract

The invention provides a preparation method of bis (2,4,6-trimethylbenzoyl)phenyl phosphine oxide, which comprises the following steps: adding a specific ether compound as a complexing agent in the reaction of sodium sand and phenyl phosphine dichloride, and adding the complexing agent to effectively inhibit the formation of phenyl phosphine sodium polyphosphide and promote the generation of phenyl phosphine sodium; a phenyl phosphine hydrogen process is not needed, so that the process cost is reduced, and the safety of the process is improved; besides, the complexing agent is a polar aproticsolvent, is low in dosage, can reduce the content of organic matters in the wastewater compared with a traditional method adopting a protic solvent as an activating agent or a proton source, has certain environmental benefits and saves the cost.

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 high-efficiency photoinitiators, suitable for initiating radiation polymerization of some unsaturated resins under ultraviolet light, especially for white formulations and glass fiber reinforced polyester / styrene systems and with light stabilizers Compatible with varnish systems and paint systems for exterior use, such as for wood, paper, metal, plastics, optical fibers, printing inks and pre-impregnated systems, etc. [0003] Among them, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (initiator 819) and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide (initiator TPO) These are two of them that are commonly and widely used. [0004] In the prior art, the preparation method of two (2,4,6-trimethylbenzoyl) phenyl phosphine oxides generall...

Claims

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Application Information

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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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