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Use of monosodium iminodiacetic acid solutions for preparing N-phosphonomethyliminodiacetic acid

A technology of monosodium iminodiacetic acid and disodium iminodiacetic acid, which is applied in the field of N-phosphonomethylglycine, can solve the problems of expensive transportation and expensive storage and transportation solutions, and achieve the goals of preventing precipitation and being easy to store and transport Effect

Inactive Publication Date: 2000-01-26
MONSANTO CO (MONSANTO CY)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Dilute solutions contain a lot of water making shipping more expensive
Heating to a temperature range sufficient to maintain solubility and prevent crystallization is impractical in some cases, or makes storing and transporting the solution expensive

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A hot (57.4° C.) solution of disodium iminodiacetate (1400 g, 42.38%, DSIDA, 593.3 g, 3.3 moles) was placed in a reactor equipped with a stirrer, heating mantle, water condenser and gas introduction tube. Hydrogen chloride gas is added to introduce the strong acid. Hydrogen chloride gas was introduced to the reactor surface at 57.4°C. Gas was passed through the reactor for about 45 minutes at a temperature between 57.4-93.4°C. The heating mantle of the reactor was replaced with a water bath and the reaction mixture was allowed to cool to 73°C. An additional amount of hydrogen chloride was bubbled into the cooled mixture while a slight vacuum was applied. A total of 139.2 g (3.8 moles) of hydrogen chloride were added. The solution was cooled to ambient temperature. A homogeneous phase remained with no apparent visible precipitate. The pH was found to be about 4. This solution is suitable for on-site storage or transport to off-site subsequent processing.

Embodiment 2

[0029] A monosodium iminodiacetic acid (IDA) solution (43.4g, 30.6%, IDA, 13.3g, 0.1 mole) was prepared and 26g of it was put into a glass reactor capable of low-pressure reaction. Hydrochloric acid (37.9% HCl, 18.0 g) and phosphorous acid (9.46 g) were added and the mixture was heated to 120°C. Formaldehyde (48.8%, CH 2 O, 8.2g) and the rest of the IDA-sodium solution. The solution was kept at 120°C for 90 minutes and then cooled. Filtration, washing and drying afforded N-phosphonomethyliminodiacetic acid (21.4 g, 97%, 91% yield) and 56.5 g of filtrate.

Embodiment 3

[0031] Preparation of monosodium iminodiacetic acid / phosphorous acid solution

[0032] The disodium iminodiacetic acid solution (921g, 40.35%, DSIDA, 371.6g, 2.1 mole) of 60 ℃ is put into reactor, and reactor is equipped with stirrer, has auxiliary heating / cooling jacket and water condenser, and heating to 90°C. Phosphorus trichloride (97.6g, 98.5%, 96.1g, PCl 3, 0.7 mol) added below the surface of the DSIDA solution. Warm the reaction and keep the temperature below 105°C during this addition. The reaction mixture was cooled to 95°C and a reaction mixture containing 2.08 moles of MSIDA, 2.1 moles of NaCl and 0.7 moles of H 3 PO 3 The solution 1011g. This solution can be used to prepare N-phosphonomethyliminodiacetic acid.

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PUM

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Abstract

A method is described for making solution stable salts of iminodiacetic acid (IDA), useful as precursors in the manufacture of N-phosphonomethylglycine. Concentrated dialkali salts of IDA which are insoluble at temperatures below about 55 DEG C., such as the disodium salt (DSIDA) are acidified to monoalkali salts, such as monosodium IDA (MSIDA). The resulting salts are stable in solution, and may conveniently be stored or transported in solution without recourse to dilution, heating, or similar measures.

Description

technical background [0001] The present invention relates to N-phosphonomethylglycine (glyphosate), in particular to a preparation method of concentrated iminodiacetic acid monosodium solution for manufacturing N-phosphonomethylglycine. [0002] N-phosphonomethylglycine (glyphosate) is an important broad-spectrum herbicide. A conventional precursor of glyphosate is N-phosphonomethyliminodiacetic acid (PMIDA), whose general chemical formula (I) is as follows: [0003] h 2 o 3 PCHN 2 (CH 2 COOH) 2 [0004] An earlier method for preparing the above compound (I) is disclosed in US3288846 by Irani et al. In this method, iminodiacetic acid (IDA) is used as starting material and prepared by hydrolysis of iminodiacetonitrile. Several process steps are required to recover and purify IDA. This acid is then phosphonomethylated with phosphorous acid and formaldehyde in the presence of mineral acids. In one embodiment, phosphorus trichloride is added to the aqueous re...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07F9/38
Inventor L・R・史密斯
Owner MONSANTO CO (MONSANTO CY)
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