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Method for the manufacture of phosphonoalkyl iminodiacetic acid

A technology of phosphonoalkyliminodiacetic acid and iminodiacetic acid, which is applied in the field of N-phosphonomethylaminoacetic acid and phosphonomethyliminodiacetic acid (PMIDA) components, which can solve the lack of reaction product selection Sexuality, adverse effects on the economy of chloride ion equipment, etc.

Active Publication Date: 2012-08-15
MONSANTO TECH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main difficulties can be attributed to the choice of acid catalyst (usually sulfuric acid and / or hydrochloric acid), the presence of chlorides (usually alkali metal chlorides), undesirable levels of by-product formation, and lack of selectivity for reaction products
In addition, PMIDA prepared according to the prior art requires special care when converting to glyphosate, while the corrosiveness of chloride ions can adversely affect the economics of the equipment
[0008] Although a lot of money has been spent to alleviate the qualitative and / or economical aspects of the fabrication technology, at best only marginal solutions are obtained for specific defects

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] In a three-necked round bottom flask equipped with a mechanical stirrer, mix 33.28g (0.25mol) of iminodiacetic acid (IDA) with 20.5g (0.25mol, 1 equivalent) of phosphorous acid and 122.5g (1.25mol, 5 equivalents) ) Phosphoric acid mixed. The reaction mixture was heated to 140 °C. Then 20.68 ml of 36.6 wt% aqueous formaldehyde (1.1 equivalents) were added over 60 minutes. During the addition, the temperature of the reaction mixture dropped from 140°C to 125°C. At the end of the formaldehyde addition, the reaction mixture was refluxed for 30 minutes. The precipitate formed on cooling the reaction mixture was isolated by filtration and rinsed with fresh water. After drying the precipitate, use 1 H NMR and 31 P NMR analysis was performed and identified as N-(phosphonomethyl)iminodiacetic acid (PMIDA, 28 g, 61.2% yield) with a purity of 81.3%.

Embodiment 2

[0053] In a three-necked round-bottomed flask equipped with a mechanical stirrer, mix 33.28g (0.25mol) of iminodiacetic acid (IDA) with 20.5g (0.25mol, 1 equivalent) of phosphorous acid, 122.5g (1.25mol, 5 equivalents) ) of phosphoric acid and 13.6g of water were mixed. The reaction mixture was heated to 130°C. Then 18.80 ml of 36.6 wt% aqueous formaldehyde (1 equivalent) were added over 118 minutes. During the addition, the temperature of the reaction mixture dropped from 130°C to 124°C. At the end of the formaldehyde addition, the reaction mixture was refluxed for 30 minutes. The precipitate formed on cooling the reaction mixture was isolated by filtration and rinsed with fresh water. After drying the precipitate, use 1 H NMR and 31 P NMR analysis was performed and identified as N-(phosphonomethyl)iminodiacetic acid (PMIDA, 39.7 g, 79.5% yield) with a purity of 94.4%.

Embodiment 3

[0055] In a three-necked round-bottomed flask equipped with a mechanical stirrer, mix 33.28g (0.25mol) of iminodiacetic acid (IDA) with 20.5g (0.25mol, 1 equivalent) of phosphorous acid, 122.5g (1.25mol, 5 equivalents) ) of phosphoric acid and 13.6g of water were mixed. The reaction mixture was heated to 140 °C. Then 18.80 ml of 36.6 wt% aqueous formaldehyde (1 equivalent) were added over 118 minutes. During the addition, the temperature of the reaction mixture dropped from 140°C to 130°C. At the end of the formaldehyde addition, the reaction mixture was refluxed for 30 minutes. The precipitate formed on cooling the reaction mixture was isolated by filtration and rinsed with fresh water. After drying the precipitate, use 1 H NMR and 31 P NMR analysis was performed and identified as N-(phosphonomethyl)iminodiacetic acid (PMIDA, 35.3 g, 71.7% yield) with a purity of 91.4%.

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PUM

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Abstract

An improved method for the manufacture of phosphonoalkyl iminodiacetic acid M2PO3-X-N- (CH2COOM) 2, wherein X is a C1-6 linear or branched alkyl group and M is selected from hydrogen, alkali, earth-alkali, ammonium and protonated amine is disclosed. The iminodiacetic acid starting material is reacted with a substantially stoichiometric amount of phosphorous acid, in the presence of a large excess of phosphoric acid to thereby yield a reaction medium insoluble reaction product (PAIDA) which can be separated from the reaction medium. In a particularly preferred approach, the phosphorous acid is prepared in situ starting from liquid P4O6.

Description

technical field [0001] The present invention relates to a process for the preparation of phosphonoalkyliminodiacetic acid (PAIDA), in particular phosphonomethyliminodiacetic acid (PMIDA) components, PMIDA is the main intermediate used in the preparation of glyphosate, grass Glyphosate is also known as N-phosphonomethylaminoacetic acid. In the presence of phosphoric acid, the iminodiacetic acid (IDA) starting component reacts with phosphorous acid and formaldehyde. The amount of phosphorous acid used is the stoichiometric level required for the synthesis of phosphonomethyliminodiacetic acid compounds. The reaction is carried out in the presence of a large amount of phosphoric acid, in particular a phosphoric acid:phosphorous acid molar ratio of 9:0.8 to 1:1. It has been found that, in the context of the claimed technology, the reaction products, primarily phosphonoalkyliminodiacetic acids, are substantially insoluble in the reaction medium and can be routinely isolated and re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/38
CPCC07F9/3808
Inventor 帕特里克·诺特戴维·莱米塞德里克·尼古拉斯·皮拉尔
Owner MONSANTO TECH LLC