Method for the production of hydroxymethyl alkyl phosphinic acids and its ester thereof

A technology for hydroxymethyl hydrocarbyl phosphinic acid and hydrocarbyl phosphinic acid ethyl ester is applied in the field of preparation of hydroxymethyl hydrocarbyl phosphinic acid and its ester compound, and achieves the effects of rich and diverse raw material sources and green synthesis process.

Inactive Publication Date: 2006-12-20
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Method for the production of hydroxymethyl alkyl phosphinic acids and its ester thereof
  • Method for the production of hydroxymethyl alkyl phosphinic acids and its ester thereof
  • Method for the production of hydroxymethyl alkyl phosphinic acids and its ester thereof

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Embodiment 1

[0016] Embodiment 1: Synthesis of ethyl phenylphosphonite: the phenylphosphine dichloride of 44.75g (0.25 mole) is dripped in the 250 milliliter four-neck flask that 46g (1 mole) ethanol is housed under stirring , control the dropwise addition temperature at 5-10°C, complete the addition in 30 minutes, then raise the temperature to 30°C for 2 hours, and pass the generated hydrogen chloride gas into another flask, absorb it with water to form hydrochloric acid. Raise the temperature to 75°C, distill under reduced pressure, distill unreacted ethanol and ethyl chloride, and the residual liquid is ethyl phenylphosphinate, which is a colorless, slightly viscous liquid, which can be used directly without purification. Next reaction.

Embodiment 2

[0017] Embodiment 2: Synthesis of hydroxymethylphenylphosphinic acid: get 50g of ethyl phenylphosphinate synthesized in Example 1, put it into a 250ml four-neck flask, heat to 80°C, and add 15g in batches After the addition of paraformaldehyde, the temperature was raised to 110°C for 1 hour to complete the reaction. Then add 100 ml of 10% dilute hydrochloric acid and keep the temperature at 70° C. for 1 hour. Part of the water, hydrogen chloride, ethyl chloride, etc. were evaporated under reduced pressure. After cooling down, a white solid could be obtained by filtration. The resulting solid was recrystallized in water, filtered, and dried to obtain 43 g of the target product, hydroxymethylphenylphosphinic acid, with a melting point of 138° C. and an acid value of 232.1 mg NaOH / g (theoretical value 232.52 mg NaOH / g).

Embodiment 3

[0018] The synthesis of embodiment 3 hydroxymethylphenylphosphinic acid ethylene glycol esters: add ethylene glycol 134g, hydroxymethylphenylphosphinic acid 43g in a 250 milliliters of there-necked flasks equipped with oil bath, stirring and rectifying column , start stirring, heat up to 140°C, reflux occurs in the rectification column, take out part of the water generated by the reaction, control the reflux ratio, heat up to 160-180°C, and a large amount of water is separated through the rectification column. After 2 hours of reaction time, the reaction was stopped, and the temperature was lowered to obtain 156 grams of a solution containing ethylene glycol and ethylene glycol hydroxymethylphenyl phosphinate. The solution can be directly used in the preparation of flame-retardant polyester.

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Abstract

This invention provides modified method for producing hydroxymethyl-hydrocarbyl phosphinic acid and esterified compound thereof, comprising: hydrocarbyl-dichlorophosphine reacts with ethanol to prepare alkyl phosphonite, and then reacts with paraformaldehyde to prepare hydroxymethyl-hydrocarbyl phosphinic acid; hydrocarbyl phosphinic acid reacts with paraformaldehyde to prepare hydroxymethyl-hydrocarbyl phosphinic acid and then reacts with some diatomic alcohol for esterification. The esterified compound provided by this invention can be used as copolymerization combustion inhibitor of polyester.

Description

Technical field: [0001] The invention relates to a preparation method of a kind of methylol hydrocarbyl phosphinic acid and its esterified products used as polymer monomers or flame retardants. It belongs to the field of chemical industry and is especially suitable for the field of flame retardant materials. Background technique: [0002] Certain methods for the preparation of hydroxymethylalkylphosphinic acids and their esters are known in the art. For example, U.S. 3,962,194 discloses a method for preparing flame-retardant polyethylene terephthalate using antimony trioxide as a catalyst and phenylphosphinate as a comonomer. Among them, the ester of methylol hydrocarbyl phosphinic acid is used because the polycondensation of polyester requires high temperature and high vacuum as conditions. Considering that the flame retardant monomer will have a certain volatilization loss under this condition, in this case, the use of methylol This loss can be minimized by reacting the ...

Claims

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Application Information

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IPC IPC(8): C07F9/30C07F9/32
Inventor 王利生毋俊生康惠宝李弥异李晓华王忠卫杨梅
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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