Method for preparing allyl phosphonic acid dimethyl ester

A technology of dimethyl allyl phosphonate and trimethyl phosphite, which is applied in the field of preparation of dimethyl allyl phosphonate, can solve the problems of no suitable preparation method, limited application and popularization, and poor reaction selectivity. Achieve good application development prospects, increase reaction yield, and good reaction selectivity

Active Publication Date: 2014-06-25
SHANDONG XINGQIANG CHEM IND TECH RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because dimethyl allyl phosphonate does not have a preparation method suitable for industrialization, its application and promotion are limited.
Although the synthesis process of dimethyl allyl phosphonate is disclosed at present, there are disadvantages such as long reaction time, too expensive raw materials, high toxicity, and poor reaction selectivity.

Method used

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  • Method for preparing allyl phosphonic acid dimethyl ester
  • Method for preparing allyl phosphonic acid dimethyl ester
  • Method for preparing allyl phosphonic acid dimethyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Set up a 250mL four-necked flask equipped with a stirrer, thermometer, high-efficiency reflux condenser and methyl chloride collector, replace the air in the device with nitrogen, add 150ml of chlorobenzene, 12.4g (0.1mol) With trimethyl phosphate, 0.075gKI and 0.01g hydroquinone, the temperature was raised to 110℃, and within 4h, 9.2g (0.12mol) chloropropene was uniformly injected by a subsurface micro pump. After the injection is completed, the reaction is kept at 110°C for 4h, the excess chloropropene is recovered by distillation, and then the solvent is removed by distillation under reduced pressure (recycling), and then the fraction at 88-92°C under the pressure of 3950Pa is collected to obtain the product dimethyl allylphosphonic acid ester. The yield is 75.6%, boiling point: 182°C, refractive index: n D 25 =1.4387, density (25℃): 1.049g / cm 3 .

Embodiment 2

[0026] Example 2 Set up a 250mL four-necked flask equipped with a stirrer, thermometer, high-efficiency reflux condenser and methyl chloride collector, replace the air in the device with nitrogen, add 100ml DMF, 12.4g (0.1mol) phosphorous acid With trimethyl ester, 0.075g Na I and 0.01g hydroquinone, the temperature was raised to 110°C, and within 5 hours, 10.72g (0.14mol) of chloropropene was uniformly injected by a micro pump below the liquid surface. After the injection is completed, the temperature is raised to 130°C and the reaction is kept for 4 hours. The excess chloropropene is distilled to recover, and then the solvent is removed under reduced pressure (recovery), and then the fraction at 88-92°C under the pressure of 3950Pa is collected to obtain the product allylphosphonic acid two Methyl ester. The yield is 84.7%, boiling point: 182°C, refractive index: n D 25 =1.4387, density (25℃): 1.049g / cm 3 .

Embodiment 3

[0027] Example 3 Set up a 250mL four-necked flask equipped with a stirrer, thermometer, high-efficiency reflux condenser and methyl chloride collector, replace the air in the device with nitrogen, add 150ml diethylene glycol dimethyl ether, 12.4g (0.1mol) trimethyl phosphite, 0.1g CuCl and 0.01g hydroquinone, raise the temperature to 110°C, and inject 12.25g (0.16mol) chloropropene evenly in a subsurface micro pump within 4h. After the injection, the temperature is raised to 160°C and the reaction is kept for 5 hours. The excess chloropropene is distilled to recover, and then the solvent is removed under reduced pressure (recycling), and then the fraction at 88-92°C under the pressure of 3950Pa is collected to obtain the product allylphosphonic acid two Methyl ester. The yield is 83.2%, boiling point: 182°C, refractive index: n D 25 =1.4387, density (25℃): 1.049g / cm 3 .

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Abstract

The invention relates to a method for preparing allyl phosphonic acid dimethyl ester. The method comprises the following steps: adding an organic solvent, trimethyl phosphate, a proper amount of catalyst and a small amount of polymerization inhibitor hydroquinone into a reaction device, heating to be 110 DEG C, within 4-6 hours, injecting chloropropene of which the mole amount is 1-2 times that of the trimethyl phosphate below the liquid level, after injection, raising the temperature of the system to be 110-160 DEG C, keeping the temperature for reacting for 4-6 hours, distilling to recycle excessive chloropropene, further performing reduced pressure distillation to remove the solvent, and subsequently collecting fraction under the pressure of 3950Pa at 88-92 DEG C, thereby obtaining the product allyl phosphonic acid dimethyl ester. The preparation method of the allyl phosphonic acid dimethyl ester is high in product yield and simple to operate, the reaction is performed at normal pressure, the product is easy to separate and purify, the equipment investment is small, on-scale production is easy to achieve, and a good application and development prospect is achieved.

Description

Technical field [0001] The invention relates to a preparation method of dimethyl allylphosphonate. The compound is a reactive halogen-free organic phosphine flame retardant suitable for use as a flame retardant for materials such as unsaturated resins and polyolefins. Background technique [0002] The types of flame retardants can be simply divided into two categories: additive type and reactive type. The additive type is convenient for application, but it is easy to migrate and has a greater impact on the mechanical properties of the material. The reactive flame retardant can overcome the above shortcomings and become a new type of flame retardant. Hot spot for agent development. [0003] At present, halogen flame retardants and phosphorus flame retardants are the two main types of flame retardants with the widest application range and high comprehensive cost performance. However, halogen-containing flame-retardant materials will release a large amount of harmful gas when a fire ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40
Inventor 王彦林俞春雷黄俊男
Owner SHANDONG XINGQIANG CHEM IND TECH RES INST CO LTD
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