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CN-117229218-B - Preparation method of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, special equipment and application thereof

CN117229218BCN 117229218 BCN117229218 BCN 117229218BCN-117229218-B

Abstract

The invention provides a preparation method of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, special equipment and application thereof, wherein the preparation method comprises the following steps of S1 continuously inputting dry inorganic acid gas into a reactor, S2 mixing raw material N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine and an auxiliary agent and then inputting the mixture into the reactor, S3 carrying out cyclization reaction on the raw material and the auxiliary agent under the catalysis of the acid gas to obtain a mixture of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, water and the auxiliary agent, and S4 cooling and separating the mixture obtained in the step S3 to obtain 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione solid and an auxiliary agent aqueous solution respectively. The preparation method of the 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione has the advantages of continuity, high efficiency, simplicity, near zero emission, mild reaction conditions and the like, can effectively shorten the reaction time, improve the production efficiency, reduce the safety risk, ensure that the product yield can reach more than 93 percent and the purity can reach more than 99 percent.

Inventors

  • LI WEI
  • Qian shengli
  • SHI YONG
  • WU CHUNHUI

Assignees

  • 江苏快达农化股份有限公司

Dates

Publication Date
20260508
Application Date
20230914

Claims (8)

  1. 1. A method for preparing 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, which is characterized by comprising the following steps: s1, continuously inputting dry acid gas into a reactor (2), and controlling the jacket temperature and the cavity internal pressure of the reactor (2), wherein the acid gas is one of hydrogen chloride, hydrogen bromide and hydrogen iodide; S2, mixing raw material N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine and an auxiliary agent, and then inputting the mixture into a reactor (2), wherein the auxiliary agent is one or two of monoglyceride stearate, polyethylene glycol, sodium lignin sulfonate, sodium polyacrylate, polydimethylsiloxane, polyoxypropylene glycerol ether, glycerol random polyether, benzyl triethylamine chloride and tetrabutylammonium chloride; S3, controlling the rotating speed of the reactor (2), and performing cyclization reaction on raw materials N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine and an auxiliary agent under the catalysis of the acid gas and at a preset reaction temperature to obtain a mixture of a product 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, water and the auxiliary agent; S4, cooling and separating the mixture obtained in the step S3 to obtain 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione solid and an aqueous solution of an auxiliary agent respectively.
  2. 2. The preparation method of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione according to claim 1, characterized in that the reactor (2) is a continuous tubular reactor, a spiral stirring structure (21) is arranged inside the reactor (2), and the raw material N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine and the auxiliary agent undergo continuous cyclization reaction under the action of the spiral stirring structure (21).
  3. 3. The process for preparing 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione according to claim 1, wherein the jacket temperature in the reactor (2) in step S1 is 80 to 150 ℃ and the pressure in the cavity is 0.05 to 1.0MPa.
  4. 4. The method for preparing 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione according to claim 1, wherein the mass concentration of the auxiliary agent is 0.1 to 5%.
  5. 5. The process for the preparation of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione according to claim 1, wherein the rotational speed of the reactor (2) during the cyclization reaction in step S3 is from 50 to 300 rpm and the reaction temperature is from 70 to 140 ℃.
  6. 6. The process for producing 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione according to claim 1, wherein the aqueous solution of the auxiliary agent obtained in step S4 is concentrated by membrane distillation and then fed to step S2 for reuse.
  7. 7. An apparatus for preparing the 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione according to claim 1, comprising a mixer (1) and a reactor (2); The mixer (1) is provided with a feed inlet A and a feed inlet B, the raw material N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine enters from the feed inlet A, the auxiliary agent enters from the feed inlet B, and the discharge outlet of the mixer (1) is communicated with the feed inlet of the reactor (2); The reactor (2) is provided with an air inlet C, an air outlet D and a discharge hole E, the acid gas enters from the air inlet C, the gas generated by the cyclization reaction of the raw material N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] aminoacetic acid and the auxiliary agent under the catalysis of the acid gas enters a tail gas removal system through the air outlet D, and the mixture of the product 3- (3, 5-dichlorophenyl) -2, 4-imidazolidindione, water and the auxiliary agent enters a separator through the discharge hole E for separation; The reactor (2) is a continuous tubular reactor, a spiral stirring structure (21) is arranged in the reactor (2), and the raw materials N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine, the auxiliary agent and the acid gas are pushed to the other end through the spiral stirring structure (21) when entering from one end of the reactor (2) for cyclization reaction, so that continuous cyclization reaction is realized.
  8. 8. Use of the method for the preparation of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione according to any one of claims 1 to 6 for the preparation of iprodione bactericides.

Description

Preparation method of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, special equipment and application thereof Technical Field The invention relates to the field of compound preparation, in particular to a preparation method of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, special equipment and application thereof. Background 3- (3, 5-Dichlorophenyl) -2, 4-imidazolidinedione is an important intermediate for synthesizing the bactericidal agent iprodione. The current preparation method commonly adopted in industry is to take N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine as a raw material and dehydrate and cyclize at a certain temperature to prepare the 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione. The industrial production process is usually carried out in an intermittent reaction kettle, the post-treatment process is complex, and the production efficiency is low. In the cyclization process, the chlorine on the benzene ring is easy to generate hydrolysis side reaction, the acid catalyst cannot be recycled, the yield is generally not more than 92%, and the purity is not more than 99%. For example, chinese patent CN 107245055 discloses a process for the preparation of iprodione by mixing N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine with an organic solvent and preparing the intermediate 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione under the catalytic action of a mixture of concentrated sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid. The preparation method uses organic solvent, VOCs are easy to be discharged in the production operation process, the environment is polluted, and the health of production operators is negatively influenced. In the chemical production process, a large amount of flammable and explosive organic solvents are used, so that potential safety hazards are increased. In addition, the amount of the strong acid catalyst is large, a large amount of acid wastewater generated by post-treatment cannot be recycled continuously, and a large pressure is brought to environmental protection treatment. Chinese patent CN109265401 discloses another test method for preparing iprodione intermediate 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, mixing N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine with 20% hydrochloric acid, stirring, heating and refluxing to obtain the product. Although the test method successfully obtains the target product, the preparation method of mixing and heating with the dilute hydrochloric acid has slow reaction rate and is easy to produce the decomposed product 3, 5-dichloroaniline. In addition, the feeding concentration needs to be controlled at a lower concentration, otherwise, after the system is heated, the materials are easy to expand to generate the danger of flushing, the preparation efficiency is low, and the safety is poor. Moreover, the dilute hydrochloric acid is adopted as a catalytic system, so that the problems of large amount of acid wastewater after treatment, high recovery cost and the like exist, and the feasibility of industrial operation is not high. Disclosure of Invention Aiming at the defects in the prior art, the invention aims to provide a preparation method, special equipment and application of 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione. The preparation method of the 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione provided by the invention comprises the following steps: S1, continuously inputting dry acid gas into a reactor, and controlling the jacket temperature and the internal pressure of a cavity of the reactor; s2, mixing raw material N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] aminoacetic acid and an auxiliary agent, and inputting the mixture into a reactor; S3, controlling the rotating speed of a reactor, and performing cyclization reaction on raw materials N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine and an auxiliary agent under the catalysis of acid gas and at a preset reaction temperature to obtain a mixture of a product 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione, water and the auxiliary agent; S4, cooling and separating the mixture obtained in the step S3 to obtain 3- (3, 5-dichlorophenyl) -2, 4-imidazolidinedione solid and an aqueous solution of an auxiliary agent respectively. In some embodiments, the reactor is a continuous tubular reactor, a dynamic stirring structure is arranged in the reactor, and the raw material N- [ [ (3, 5-dichlorophenyl) amino ] carbonyl ] glycine and the auxiliary agent are subjected to continuous cyclization reaction under the action of the dynamic stirring structure. In some embodiments, the acid gas in step S1 is one of hydrogen chloride, hydrogen bromide, hydrogen iodide. In some embodiments, the temperature of the jacket in the reactor in step S1 is 80-150℃and the pressure inside the cavity is 0.05-1.0MPa. In some embodiments, the auxiliary agent in step S2 is one or two of monoglyceride stearate, polyethylene gly