Glyphosate → Iminodiacetic acid

Participants

Reaction Steps

N-phosphonomethylglycine (glyphosate) is an important broad spectrum herbicide. One conventional precursor to glyphosate is N-phosphonomethyliminodiacetic acid having the following structure: ##STR1## Conventional routes to compound (I) typically involve phosphonomethylating iminodiacetic acid (IDA), the latter obtained by recovering (IDA) from the crude hydrolysate of iminodiacetonitrile (IDAN) by acidification with a mineral acid, crystallization of IDA, filtration thereof, and drying. Such processes result in waste in that the alkali metal salt solution separated from IDA upon the filtration step contains unrecovered IDA. Indeed, fractional crystallization is necessary to precipitate the alkali metal salt, which can then be separated from the IDA solution by centrifugation. In U.S. Pat. No. 3,808,269, disclosed is a process of recovering IDA from an aqueous solution of sodium sulfate and the amino acid by adjusting the pH of the solution to 1.5-3 to form an IDA precipitate and a first mother liquor, and separating and recovering the IDA precipitate therefrom. Sodium sulfate can then be precipitated from the first mother liquor by concentrating the liquor and adjusting the temperature so as to prevent the concomitant precipitation of IDA. The process can then be repeated. However, at some point successive fractional crystallization steps become uneconomical, notwithstanding the presence of additional product in the solution. U.S. Pat. No. 3,852,344 discloses a similar process wherein the sulfuric acid is replaced with hydrochloric acid, with sodium chloride being recovered as the by-product instead of sodium sulfate.

Provenance & Evidence