Method for preparing paraphthaloyl chloride

A technology of terephthaloyl chloride and terephthalic acid, which is applied in the field of chemical raw material preparation, can solve the problems of high cost and low catalyst activity, and achieve the effects of high product yield and purity, and simple and convenient reaction operation.

Active Publication Date: 2014-04-02
河南能源集团研究总院有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the outstanding problems of low catalyst activity and high cost in the preparation of terephthaloyl chloride by the reaction of terephthalic acid and thionyl chloride, the purity of the product can reach more than 99% after multiple recrystallizations or multiple vacuum distillations. , the purpose of the present invention is: to develop a kind of cheap and easy to obtain, stable high activity, high selectivity catalyst to thionyl chloride, be used for catalyzing the reaction of terephthaloyl dichloride and thionyl chloride, high yield makes High Purity Terephthaloyl Chloride

Method used

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  • Method for preparing paraphthaloyl chloride
  • Method for preparing paraphthaloyl chloride
  • Method for preparing paraphthaloyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 100 grams of terephthalic acid (PTA), 300 grams of thionyl chloride (SOCl 2 ) and 2 grams of 1-methylpyrrolidine were added to a 1-liter round-bottomed flask, stirred evenly, heated to 100°C for 10 hours, and the generated HCl and SO 2 The mixed gas is first absorbed with water, and then absorbed with 30% NaOH solution. After the reaction is completed, the catalyst and excess SOCl are recovered by distillation 2 156 grams, and 110 grams of product terephthaloyl chloride (TPC) were obtained by rectification under reduced pressure, and the separation yield was 90%. The product was detected by GC-MS and 1 H NMR, 13 C NMR was used for qualitative analysis, and gas chromatography detected that the purity was higher than 99%.

Embodiment 2～25

[0021] The specific method of Examples 2-25 is similar to that of Example 1, and the specific reaction conditions and results are listed in Table 1.

Embodiment 26

[0023] With the SOCl that embodiment 1 reclaims 2 and catalyst into a 1 L round bottom flask, followed by SOCl 2 145 grams, stirred evenly, raised the temperature to 100°C and reacted for 10 hours, the generated HCl and SO 2 The mixed gas is first absorbed with water, and then absorbed with 30% NaOH solution. After the reaction is completed, the catalyst and excess SOCl are recovered by distillation 2 156 grams, and obtain product TPC110 grams by rectification under reduced pressure, and separation yield is 90%. The product was detected by GC-MS and 1 H NMR, 13 C NMR was used for qualitative analysis, and gas chromatography detected that the purity was higher than 99%.

[0024] According to Example 1, it can be seen that 1-methylpyrrolidine can catalyze PTA and SOCl 2 The reaction prepares TPC, and the product yield can reach 90%. Examples 2-3 show that with 1-methylpiperidine and 1-ethylpiperidine as catalysts, the TPC yield can also reach 90%. Embodiment 4 does not us...

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Abstract

The invention relates to a method for preparing paraphthaloyl chloride. The method comprises the following steps: mixing thionyl chloride and terephthalic acid according to the mass ratio of 2:1 to 5:1; adding one or more of nitrogen-containing organic bases such as substituted pyrrolidine, substituted piperidine, substituted pyridine, (substituted) quinoline, (substituted) isoquinoline, (substituted) phenanthroline, substituted imidazole, substituted benzimidazole and the like as a catalyst, which are 0.5-2% of mass of terephthalic acid; reacting at 70-120 DEG C for 4-16 hours; distilling and recovering excessive thionyl chloride; distilling or rectifying in vacuum to recover the catalyst, so as to obtain the product paraphthaloyl chloride by vacuum rectification, wherein the yield can be up to 96%, and the purity is higher than 99%. The method has the advantages that the catalyst is low in price and available, and can be recycled, the product is high in yield and purity, the reaction operation is simple and convenient and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical raw material preparation, and in particular relates to a method for preparing terephthaloyl dichloride. Background technique [0002] Terephthaloyl chloride is an important organic chemical raw material, which can be used as a medicine and pesticide intermediate, and can also be used to synthesize high-temperature resistant and high-strength polymer materials such as aramid 1414, polyarylsulfone, polyester, and polyarylate. Widely used in aircraft, rockets, missiles, space suits, special military uniforms and fire fighting equipment. [0003] Terephthaloyl chloride can be produced by hydrolysis of p-xylene after photocatalytic chlorination. However, the reaction temperature of this method is as high as 200-300°C, the energy consumption is high, and the product yield is not high. Terephthaloyl chloride can also be prepared from terephthalic acid through acid chloride reaction. The commonly used a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C63/30C07C51/60C07C51/64
CPCY02P20/584C07C51/60
Inventor 黄义争付瑶徐杰宋灿高进魏灵朝苗虹蒋元力
Owner 河南能源集团研究总院有限公司
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