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Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor

A technology of microchannel reactor and p-toluenesulfonyl chloride, which is applied in chemical instruments and methods, chemical/physical/physicochemical reactors, sulfonic acid preparation, etc., can solve the problem of high raw material cost of thionyl chloride, difficult removal of phosphoric acid, Affect product quality and other issues, to achieve the effect of easy automatic production, increase product yield, and curb side reactions

Active Publication Date: 2021-08-20
JINHUA SHUANGHONG CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of these methods is: (1) phosgene in the phosgene method is highly toxic gas, uses unsafe and the raw material cost of thionyl chloride is higher; (2) thionyl chloride method can produce the sulfur dioxide of polluting environment By-products; (3) The by-product phosphorous acid or phosphoric acid generated by the phosphorus oxychloride method or the phosphorus oxychloride method is difficult to remove, which affects product quality

Method used

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  • Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor
  • Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor
  • Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1, utilize the method for continuously synthesizing p-toluenesulfonyl chloride in microchannel reactor:

[0059] The feed list is shown in Table 1 below; the feed amount refers to the amount of raw materials entering the static mixer.

[0060] Table 1

[0061] name molecular weight moles Feed amount (g) toluene 92.14 1 92.14 Chlorosulfonic acid (calculated by 100%) 116.52 2.01 234.21 1,2-Dichloroethane 98.96 15 1484.40 Tetraethylammonium chloride 165.7 0.05 8.29

[0062] Send toluene, chlorosulfonic acid, dichloroethane and tetraethylammonium chloride into the constant temperature static mixer with a metering pump at a molar ratio of 1:2.01:15:0.05, and control the temperature of the materials in the constant temperature static mixer Not higher than -5°C (generally -10°C ~ -5°C), the material flowing out from the outlet of the constant temperature static mixer is injected into the microchannel reactor at 1....

Embodiment 2

[0064] The feed list is as shown in Table 2.

[0065] Table 2

[0066] name molecular weight moles Quantity (grams) toluene 92.14 1 92.14 Chlorosulfonic acid (calculated by 100%) 116.52 2.01 234.21 Dichloromethane 84.93 15 1273.95 Piperazine 86.14 0.1 8.61

[0067] The flow rate of the material is 1ml / min, injected into the microchannel reactor, and the temperature of the material in the microchannel reactor is precisely controlled at 60±0.2°C, and the retention time of the material in the reactor is about 26 minutes. The constant temperature static collector controls the temperature 10±0.2°C. The rest are equal to Example 1.

[0068] The result is:

[0069] The filter cake is the crude product of p-toluenesulfonyl chloride. According to capillary gas chromatography analysis, the purity of p-toluenesulfonyl chloride is 98.28%, and the yield is 94.66%. The purity of o-toluenesulfonyl chloride recovered from the filtrate wa...

Embodiment 3

[0071] Feeding table is as follows Table 3.

[0072] table 3

[0073] name molecular weight moles Quantity (grams) toluene 92.14 1 92.14 Chlorosulfonic acid (calculated by 100%) 116.52 2.01 234.21 Dichloromethane 84.93 15 1273.95 Triethylamine 101.19 0.05 5.06

[0074] The flow rate of the material is 1.2ml / min; the channel diameter of the microchannel reactor is about 500 microns, and the length is about 15000mm. The temperature of the material in the microchannel reactor is precisely controlled at 60±0.2°C. The time is about 21 minutes, and the constant temperature static collector controls the temperature at 10±0.2°C. The rest are equal to Example 1.

[0075] The result is:

[0076] The filter cake is crude p-toluenesulfonyl chloride, and analyzed by capillary gas chromatography: the crude p-toluenesulfonyl chloride has a purity of 97.99% and a yield of 90.55%. The purity of o-toluenesulfonyl chloride recovered from th...

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Abstract

The invention discloses a method for continuously synthesizing paratoluensulfonyl chloride by using a micro-channel reactor. The method comprises the following steps: by using alkyl halide as a solvent, toluene as a raw material, chlorosulfonic acid as a chlorosulfonating agent and a material obtained by mixing toluene, chlorosulfonic acid, alkyl halide and a catalyst as a reaction starting material, feeding the reaction starting material into a microchannel reactor, carrying out chlorosulfonation reaction, and performing post-treatment on a reaction product flowing out of the microchannel reactor to obtain paratoluensulfonyl chloride. According to the invention, continuous production of p-toluenesulfonyl chloride can be realized, the production efficiency can be greatly improved, and the output of waste acid can be greatly reduced.

Description

technical field [0001] The invention relates to the technical field of fine chemical intermediates, in particular to a process for preparing p-toluenesulfonyl chloride by chlorosulfonating toluene with chlorosulfonic acid in a microchannel reactor. Background technique [0002] p-toluenesulfonyl chloride is a very important fine chemical intermediate, which is widely used in dyestuff, medicine and pesticide industry. In the dye industry, it is mainly used for the manufacture of disperse, ice dyeing, and acid dyes; in the pharmaceutical industry, it is mainly used for the production of sulfamethazone, etc.; in the pesticide industry, it is mainly used for mesotrione, sulcotrione, and nail cream Ling and so on. [0003] The synthetic route of p-toluenesulfonyl chloride mainly uses toluene and chlorosulfonic acid as raw materials, and ammonium chloride, N, N-dimethylacetamide and triethylamine as catalysts to prepare p-toluenesulfonate through sulfonation and acyl chloride rea...

Claims

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Application Information

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IPC IPC(8): C07C309/86C07C303/02C07C303/08B01J19/00
CPCC07C303/02C07C303/08B01J19/0093B01J2219/00957B01J2219/00961B01J2219/00984C07C309/86C07C309/30
Inventor 徐建成肖刚郑伟良
Owner JINHUA SHUANGHONG CHEM CO LTD
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