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Preparation method of methylene succinyl chloride

A technology for the acylation of methylene succinyl and chloride, which is applied in the field of preparation of methylene succinyl chloride, can solve the problems of difficult control of carboxyl reaction, difficult temperature control, poor double bond activity, etc., and achieve stable quality, The effect of controllable reaction conditions and simple production process

Active Publication Date: 2014-09-10
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] There are many new technologies in the industry, such as the reaction method of chlorine gas, chlorine acid and sulfur dichloride, and the direct reaction of sulfur, chlorine gas and chlorine acid, but the latter reacts violently and the temperature is difficult to control. Reduce the heat exchange between chlorine and chilled water to ensure the ideal reaction temperature
Moreover, itaconic acid (methylene succinic acid) molecule contains two carboxyl groups, due to the interaction, it has a high melting point and poor double bond activity.
In the chloroacylation reaction, the reaction of the carboxyl group is not easy to control

Method used

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  • Preparation method of methylene succinyl chloride
  • Preparation method of methylene succinyl chloride

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[0019] The preparation method of methylene succinoyl chloride provided by the present invention comprises the steps of chloroacylation reaction of itaconic acid and chloroacylating reagent, crude product filtration and the like. The chloroacylation reaction of the present invention is carried out at an absolute pressure of 0-100Kpa and 30-200°C, and nitrogen gas is introduced into the system to facilitate the discharge of gas products. During the reaction, a solvent may or may not be used, and each reactant is reacted in a molten state.

[0020] The chloroacylating agent used in the present invention can be any one or more of thionyl chloride, phosphorus pentachloride, phosphorus trichloride, and benzoyl chloride.

Embodiment 1

[0022] The preparation method of the methylene succinoyl chloride described in the present embodiment specifically comprises the following steps:

[0023] Add 30 g of itaconic acid, 80 g of phosphorus pentachloride and 2 g of N,N-dimethylformamide into a 500 ml four-neck flask equipped with a stirrer, thermometer, exhaust gas outlet, and air inlet. The tail gas absorption system is an absorption bottle filled with 150ml 30% sodium hydroxide solution and a vacuum pump. Turn on the vacuum pump so that the gas in the four-neck flask is discharged through the absorption bottle, and the vacuum degree of the system is maintained at about 20KPa. The temperature was raised to 80°C, and the reaction was kept for 2 hours. After the reaction, the material was cooled to 20°C and filtered through a sand core funnel to obtain 32.3 g of methylene succinoyl chloride with a yield of 83.9%.

[0024] H NMR spectroscopy (such as figure 1 (shown) shows that: the chemical shifts at 6.52 and 5.93...

Embodiment 2

[0026] The preparation method of the methylene succinoyl chloride described in the present embodiment specifically comprises the following steps:

[0027] Add 30 g of itaconic acid, 32 g of thionyl chloride and 2 g of N,N-dimethylformamide into a 500ml four-neck flask equipped with a stirrer, thermometer, exhaust gas outlet, and air inlet, and turn on the vacuum pump to make The gas in the four-neck flask is discharged through the absorption bottle, and the system maintains a vacuum of 20KPa. Raise the temperature to 80°C, add 40 g of thionyl chloride to the constant-pressure dropping funnel, start to add the thionyl chloride dropwise, and keep the reaction for 2 hours. The temperature was raised to 110°C, and unreacted raw materials were evaporated under a negative pressure of 80°C. Cool to room temperature and filter with a sand core funnel to obtain 33.9 g of methylene succinoyl chloride with a yield of 88.1%. H NMR and IR spectrogram data are similar to Example 1, indica...

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Abstract

The invention provides a preparation method of methylene succinyl chloride. The preparation method comprises the following steps: adding itaconic acid, a chloroacylation reagent and a catalyst into a reactor, reacting in the presence or absence of a solvent to prepare a crude product of methylene succinyl chloride, and performing post-treatment operations of filtering and the like to prepare a final product of methylene succinyl chloride. The production process is simple, the reaction conditions are controllable, the problem of difficult control of itaconic acid due to reaction of two carboxyl groups in chloroacylation reaction is solved, and finally prepared methylene succinyl chloride is high in yield and purity and stable in quality.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, in particular to a preparation method of methylene succinoyl chloride. Background technique [0002] Acid chlorides refer to compounds containing -C(O)Cl functional groups, belonging to the category of acid halides, which are carboxylic acid derivatives formed after the hydroxyl group in carboxylic acid is replaced by chlorine. Low-level acid chlorides are liquids with a pungent smell, and high-level ones are solids. The most commonly used preparation method of acid chloride is to prepare by reacting thionyl chloride, phosphorus trichloride, phosphorus pentachloride and carboxylic acid. The preparation equation is as follows: [0003] R-COOH + SOCl 2 → R-COCl + SO 2 + HCl [0004] 3R-COOH + PCl 3 → 3R-COCl + H 3 PO 3 [0005] R-COOH + PCl 5 → R-COCl + POCl 3 + HCl. [0006] There are many new technologies in the industry, such as the reaction method of chlorin...

Claims

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Application Information

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IPC IPC(8): C07C57/66C07C51/60
CPCC07C51/60C07C57/66
Inventor 王传兴高传慧李东阳刘军凯武玉民
Owner QINGDAO UNIV OF SCI & TECH
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