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Preparation method of diphenyl phenylphosphonate

A technology of diphenyl phenyl phosphonate and triphenyl phosphite, which is applied in the field of preparation of diphenyl phenyl phosphonate, can solve problems such as difficult industrial production, environmental pollution, and difficult separation, and achieve environmental protection. Less pollution, simple post-treatment, and improved yield

Active Publication Date: 2020-09-08
ZHEJIANG WANSHENG
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

But metal catalyst Raney nickel is used in this method, and Raney nickel is easy to catch fire at high temperature, but this method is difficult to carry out reaction under the temperature lower than 300 ℃, and there is the existence of by-product phenol in the reaction product, by-product To be processed, the process of processing will cause environmental pollution
[0008] In 2006, Yao and Levchik (Tetrahedron Letters, 47 (2006) 277-281) added halogenated benzene and triethyl phosphite to triphenyl phosphite, and used anhydrous nickel chloride as a catalyst to carry out the catalytic reaction. Phenyl ester and triethyl phosphite are first transesterified, and after the transesterification, the isomerization reaction is carried out. After the process of transesterification, there is a large amount of diphenyl ethyl phosphate impurities (about 10%). This impurity It is difficult to separate from the target product. If it is refined, the refined treatment process will increase the cost of synthesis, and it is difficult to carry out industrial production

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  • Preparation method of diphenyl phenylphosphonate
  • Preparation method of diphenyl phenylphosphonate
  • Preparation method of diphenyl phenylphosphonate

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preparation example Construction

[0029] The invention provides a kind of preparation method of diphenyl phenylphosphonate, comprising the following steps:

[0030] (1) Under Raney nickel catalysis and protective atmosphere conditions, using benzene bromide as an initiator, triphenyl phosphite is carried out to isomerization reaction, and the gained reaction feed liquid is subjected to vacuum distillation and solid-liquid separation successively to obtain separating liquid;

[0031] (2) The separation liquid and phenylphosphonic acid dichloride are mixed for esterification reaction to obtain diphenyl phenylphosphonic acid;

[0032] Wherein, the molar ratio of triphenyl phosphite to benzene bromide is 1:(0.5-2); the temperature of the isomerization reaction is 220-260°C.

[0033] In the invention, under the conditions of Raney nickel catalysis and protective atmosphere, benzene bromide is used as an initiator to perform isomerization reaction on triphenyl phosphite. In the present invention, the protective at...

Embodiment 1

[0046] 1. Wet catalyst Raney nickel (8kg, dosage is 2.58% of the mass of triphenyl phosphite, Raney nickel particle size 50μm) is added to the reaction kettle, and the temperature is raised to 120~ After vacuum dehydration at 125°C for 2 hours, slowly add triphenyl phosphite (310kg, 1kmol) under nitrogen protection, raise the temperature to 240-250°C, start to add benzene bromide (80kg, 0.51kmol) dropwise, and add dropwise for 2h , keep warm for half an hour after the dropwise addition, monitor by liquid chromatography, and stop the reaction after monitoring the complete reaction of the raw material triphenyl phosphite;

[0047] The monitoring data in the reaction process are shown in Table 1:

[0048] Monitoring data in the reaction process of table 1

[0049]

[0050] 2. Lower the temperature of the reaction feed solution in step 1 to 70-80°C, recover excess benzene bromide under reduced pressure, the vacuum degree is 2-3mmHg, the recovery temperature is 130-135°C, and a...

Embodiment 2

[0058] 1. Catalyst Raney nickel (7 kg of recovered Raney nickel, add 1 kg of dried new catalyst, the dosage is 2.58% of the mass of triphenyl phosphite, and the Raney nickel particle size is 50 μm) into the reaction kettle, add phosphorous acid Triphenyl ester (310kg, 1kmol), under the protection of nitrogen, the temperature was raised to 240-250°C, and benzene bromide (80kg, 1.02kmol) was added dropwise for 3 hours. The method is monitored, and the reaction is stopped after monitoring the complete reaction of the raw material triphenyl phosphite;

[0059] The monitoring data during the reaction are shown in Table 2:

[0060] Table 2 reaction process monitoring data

[0061]

[0062]

[0063] 2. After the reaction, cool down to 70-80°C, and start to reduce the pressure to recover excess benzene bromide. The vacuum degree is 2-3mmHg, and the recovery temperature is 140-145°C. After recovery, filter the catalyst under nitrogen pressure filtration at 60-65°C , and the cat...

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Abstract

The invention belongs to the technical field of organic synthesis, and provides a preparation method of diphenyl phenylphosphonate. The preparation method comprises the following steps: under the conditions of Raney nickel catalysis and protective atmosphere, by taking bromobenzene as an initiator, carrying out an isomerization reaction on triphenyl phosphite, carrying out reduced pressure distillation and solid-liquid separation on the reaction liquid, mixing the obtained separation liquid with phenylphosphonic dichloride, and carrying out an esterification reaction to obtain diphenyl phenylphosphonate, wherein the molar ratio of triphenyl phosphite to bromobenzene is 1:(0.5-2), and the temperature of the isomerization reaction is 220-260 DEG C. According to the method, the isomerizationreaction temperature is remarkably reduced by controlling the dosage of bromobenzene; impurity generated by the isomerization reaction is phenol, and the impurity generated in the first step reacts with phenylphosphonic dichloride to be converted into the target product diphenyl phenylphosphonate, so that the yield of the synthesis method is increased, and the purity of the obtained product is high; and bromobenzene and raney nickel in the method disclosed by the invention can be recycled, so that the reaction cost is low, and the environmental pollution is small.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of diphenyl phenylphosphonate. Background technique [0002] Aryl phosphates belong to halogen-free phosphates, which are mainly used in flame-retardant plasticizers of engineering plastics and phenolic resin laminates, and can be used as halogen-free and environmentally friendly flame retardants. A special form of base phosphate, the English name is: Benzen phosphoniciddi-phenvlester, the structural formula is as follows: [0003] [0004] CAS: 3049-24-9, molecular formula: C 18 h 15 o 3 P, the physical and chemical properties are as follows: white, odorless crystalline powder, slightly deliquescent; vapor pressure 0.01kPa / 20°C; flash point 220°C; melting point 58-62°C; boiling point 370°C; solubility: insoluble in water, slightly soluble In alcohol, soluble in benzene, chloroform, acetone, easily soluble in ether; relative density (water=1)...

Claims

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Application Information

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IPC IPC(8): C07F9/40
CPCC07F9/4084C07F9/4021Y02P20/584
Inventor 吕云兴高洪明王秋伟
Owner ZHEJIANG WANSHENG
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