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A kind of method for preparing aromatic diacid chloride

An aromatic diacid chloride and aromatic technology, which is applied in the field of preparation of aromatic diacid chloride, can solve the problems of long reaction time, shortened reaction time, and low product yield, and achieves short reaction time, simple and convenient reaction operation, and high product yield. high effect

Active Publication Date: 2018-05-18
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problem of preparing phthaloyl dichloride, isophthaloyl chloride, terephthaloyl dichloride and other aromatic diacids by reacting aromatic diacids such as phthalic acid, isophthalic acid and terephthalic acid with thionyl chloride Problems such as low catalyst activity, high cost, long reaction time, and low product yield in the process, the purpose of the invention is to: develop a kind of aromatic compound such as sulfur oxychloride and phthalic acid, isophthalic acid, terephthalic acid The rapid reaction method of dicarboxylic acid can produce phthaloyl dichloride, isophthaloyl dichloride, terephthaloyl dichloride and other aromatic diacid dichlorides in high yield, shorten the reaction time and improve the efficiency of the device

Method used

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  • A kind of method for preparing aromatic diacid chloride
  • A kind of method for preparing aromatic diacid chloride
  • A kind of method for preparing aromatic diacid chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 5.0 grams of terephthalic acid (PTA), 20.0 grams of thionyl chloride (SOCl 2 ) and 0.1 gram of 1-methylpyrrolidine were added into a 50ml reactor equipped with a reflux condenser, heated to reflux at 130°C for 2 hours, the generated HCl and SO 2 The gas is passed into water and 30% NaOH solution sequentially in time, and the pressure in the reactor is 0.1MPa. Recovery of catalyst and excess SOCl by distillation 2 , Distilled under reduced pressure to obtain 1.8 grams of product terephthaloyl chloride (TPC), the molar yield relative to PTA was 36%. The product was detected by GC-MS and 1 H NMR, 13 CNMR is used for qualitative analysis, and the purity detected by gas chromatography and liquid chromatography is higher than 99%.

[0018] Table 1. Aromatic dicarboxylic acid and SOCl 2 Reaction Conditions and Results of Preparation of Aromatic Diformyl Chloride

[0019]

[0020]

Embodiment 2～3

[0022] The specific procedure of Examples 2-3 is similar to that of Example 1, and the specific reaction conditions and results are shown in Table 1.

Embodiment 4

[0024] 5.0 grams of PTA, 20.0 grams of SOCl 2 Add 0.1 gram of 1-methylpyrrolidine into a 50ml reactor, heat at 130°C for 2 hours, the pressure in the reactor gradually rises to 2.8MPa, cool down to 25°C, and the gas in the reactor is sequentially passed into water and 30% NaOH solution , the HCl and SO generated by the absorption reaction 2 gas. After the reaction, the mixture is distilled to recover the catalyst and excess SOCl 2 , and then distilled under reduced pressure to obtain 6.0 g of product TPC with a molar yield of 99%. The product was detected by GC-MS and 1 H NMR, 13 C NMR for qualitative analysis, gas chromatography, liquid chromatography detection purity higher than 99%.

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Abstract

The invention relates to a method for preparing aromatic diacid chloride, specifically, in a pressure reactor, using thionyl chloride, phthalic acid, isophthalic acid, terephthalic acid and other aromatic diacids as raw materials, pyrrole Alkanes, piperidines, pyridines, quinolines, isoquinolines, o-phenanthrolines, imidazoles, benzimidazoles and other nitrogen-containing organic bases or their derivatives are used as catalysts, reacted at 90-135°C for 1-3 hours, and the pressure of the reaction system is controlled Between 0.2 and 4Mpa, distill or vacuum distillation to recover thionyl chloride and catalyst, and the molar yield of phthaloyl dichloride, isophthaloyl dichloride, terephthaloyl dichloride and other aromatic diacid chlorides is up to 99%. , with a purity of over 99%. The invention has the advantages of short reaction time, high product yield, simple and convenient reaction operation and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing aromatic diacid chlorides. Background technique [0002] Aromatic diacid chlorides such as phthaloyl dichloride, isophthaloyl dichloride and terephthaloyl dichloride are important organic chemical raw materials, which can be used as pharmaceutical and pesticide intermediates, as well as polymer monomers for the synthesis of Aramid 1313, aramid 1414, polyaryl sulfone, poly (aryl) ester and other high temperature resistant, high strength polymer materials are widely used in aircraft, rockets, missiles, special military uniforms and fire fighting equipment. [0003] Terephthaloyl chloride can be obtained by hydrolyzing 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. Aromatic diacid chlorides such as phthaloyl ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/60C07C63/22C07C63/24C07C63/30B01J31/02
Inventor 黄义争徐杰高进苗虹孙颖路芳
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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