Method for catalyzed synthesis of N-(phosphonomethyl) iminodiacetic acid by p-toluenesulfonic acid

A technology of p-toluenesulfonic acid and diglyphosate, which is applied in the chemical industry, can solve the problems of decreased yield of diglyphosate, volatile loss, poor operating environment, etc., and achieve the effects of reducing production costs, high solubility, and reducing material loss

Inactive Publication Date: 2014-02-05
CHONGQING UNISPLENDOUR CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since the amount of hydrochloric acid used in the reaction process is excessive relative to iminodiacetic acid, there is a large amount of hydrochloric acid in the system after the reaction, which is difficult to carry out post-treatment, and attempts to reduce the amount of hydrochloric acid have resulted in the production of diglyphosate rate dropped significantly
In addition, because hydrochloric acid is a volatile acid, it is easy to be volatile and lost in the production process of bisglyphosate and form a large amount of acid mist, which in turn brings many problems such as poor operating environment and easy corrosion of equipment.

Method used

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  • Method for catalyzed synthesis of N-(phosphonomethyl) iminodiacetic acid by p-toluenesulfonic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add phosphorous acid 91.6g (content 98.5%, 1.1mol), formaldehyde 97.3g (content 37%, 1.2mol), p-toluenesulfonic acid monohydrate 9.5g (content 99%, 0.05mol) and water 200mL into the reactor, Heat to 115-120°C, add a suspension consisting of 135.7g of iminodiacetic acid (content 98%, 1mol) and water 300mL dropwise at a constant speed within 3 hours, and keep it warm for 2 hours after adding; transfer the reaction solution to the crystallizer In the medium, lower the temperature to 10-15°C, heat and crystallize for 2 hours; then transfer the solid-containing liquid to a separator, separate the liquid from the solid, wash the solid with 20 mL of water, and dry to obtain 210.0 g of bisglyphosate (white solid), with a content of 98.7% , yield 91.3%; mother liquor weighs 603g, which contains 8.9g p-toluenesulfonic acid.

[0027] Transfer the mother liquor to the concentrator, concentrate to remove 140g of water, and then send it back to the reactor, add 0.6g of p-toluenesulfo...

Embodiment 2

[0030] Add 150.4g of phosphorous acid (content 60%, 1.1mol), 19.2g of p-toluenesulfonic acid monohydrate (content 99%, 0.1mol) and 300mL of water into the reactor, heat to 115-120°C, within 3 hours at the same time Add formaldehyde 97.3g (content 37%, 1.2mol) and a suspension composed of iminodiacetic acid 135.7g (content 98%, 1mol) and water 300mL dropwise at a uniform speed, and keep warm for 2 hours after adding; transfer the reaction solution to the crystallization In the container, cool down to 10-15°C, heat and crystallize for 2 hours; then transfer the solid-containing liquid to the separator, separate the liquid from the solid, wash the solid with 20 mL of water, and dry to obtain 215.7 g of bisglyphosate (white solid), with a content of 98.3 %, the yield is 93.4%; the mother liquor weighs 607g, which contains 9.3g of p-toluenesulfonic acid.

[0031] Transfer the mother liquor to the concentrator, concentrate to remove 250g of water, then return to the reactor, add 10....

Embodiment 3

[0034] Add 135.7g of iminodiacetic acid (content 98%, 1mol), phosphorous acid 91.6g (content 98.5%, 1.1mol), 201.5g of p-toluenesulfonic acid monohydrate (content 99%, 1.05mol) and water into the reactor 500mL, heat to 115-120°C, add formaldehyde 97.3g (content 37%, 1.2mol) dropwise at a uniform speed, and keep warm for 2 hours after adding; hour; then transfer the solid-containing liquid to the separator, separate the liquid from the solid, wash the solid with 20mL of water, and dry to obtain 212.0g of bisglyphosate (white solid), with a content of 98.5% and a yield of 92.0%; the weight of the mother liquor is 792.0g, of which Contains 199.6g of p-toluenesulfonic acid.

[0035] Transfer the mother liquor to the concentrator, concentrate to remove 42g of water, and then send it back to the reactor, add 2.0g of p-toluenesulfonic acid monohydrate, and add 135.7g of iminodiacetic acid (content 98%, 1mol) and phosphorous acid 87.4g (content 98.5%, 1.05mol), heated to 115-120°C, a...

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Abstract

The invention discloses a method for catalyzed synthesis of N-(phosphonomethyl) iminodiacetic acid by p-toluenesulfonic acid. The method comprises the following steps: by taking iminodiacetic acid, phosphorous acid and formaldehyde as raw materials, carrying out reaction at 100-120 DEG C under catalysis of p-toluenesulfonic acid; cooling a reaction liquid; crystallizing; carrying out solid separation to obtain the N-(phosphonomethyl) iminodiacetic acid; after concentrating mother liquor, supplementing the p-toluenesulfonic acid; and then, adding a reaction raw material for synthesis of next batch. According to the method disclosed by the invention, by adopting the p-toluenesulfonic acid to replace hydrochloric acid as a catalyst, the p-toluenesulfonic acid is high in boiling point and not easy to volatilize. In the production process, the p-toluenesulfonic acid is free from volatilization loss, and does not form acid mist, so that the operating environment is good and the equipment is not easy to corrode. In addition, the p-toluenesulfonic acid is great in water solubility, and the mother liquor which is appropriately concentrated can be directly used, thus not only is generation of a plenty of acid and salt containing wastewater avoided, but also the material loss is reduced and the production cost is lowered.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to a method for synthesizing organic compounds. Background technique [0002] Diglyphosate (N-phosphoromethyliminodiacetic acid) is an important synthetic raw material for the broad-spectrum herbicide glyphosate (N-phosphoromethylglycine). The main synthesis method of bisglyphosate is to react iminodiacetic acid, phosphorous acid and formaldehyde under the catalysis of hydrochloric acid. Since the amount of hydrochloric acid used in the reaction process is excessive relative to iminodiacetic acid, there is a large amount of hydrochloric acid in the system after the reaction, which is difficult to carry out post-treatment, and attempts to reduce the amount of hydrochloric acid have resulted in the production of diglyphosate rate dropped significantly. In addition, because hydrochloric acid is a volatile acid, it is easy to be volatile and lost in the production process of bisglyphosat...

Claims

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Application Information

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IPC IPC(8): C07F9/38
Inventor 丁永良刘佳吴传隆游欢李静张飞屈洋李双龙李朝全
Owner CHONGQING UNISPLENDOUR CHEM
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