Control of N-(phosphonomethyl)iminodiacetic acid conversion in manufacture of glyphosate

Patent metadata

Field	Value
Publication number	US-9409935-B2
Application number	US-88428910-A
Country	US
Kind code	B2
Filing date	Sep 17, 2010
Priority date	Apr 1, 2005
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

This invention relates to the preparation of N-(phosphonomethyl)glycine (“glyphosate”) from N-(phosphonomethyl)iminodiacetic acid (“PMIDA”), and more particularly to methods for control of the conversion of PMIDA, for the identification of reaction end points relating to PMIDA conversion and the preparation of glyphosate products having controlled PMIDA content.

First claim

What is claimed is:

1. A method for monitoring or detecting a conversion of N-(phosphonomethyl)iminodiacetic acid to N-(phosphonomethyl)glycine in the course of a catalytic oxidation of N-(phosphonomethyl)iminodiacetic acid in an aqueous medium, the method comprising:
introducing an aqueous medium containing N-(phosphonomethyl)iminodiacetic acid into an oxidation reaction zone;
contacting N-(phosphonomethyl)iminodiacetic acid with an oxidizing agent in the aqueous medium within said oxidation reaction zone in the presence of an oxidation catalyst, thereby effecting oxidation of N-(phosphonomethyl)iminodiacetic acid and producing N-(phosphonomethyl)glycine;
measuring the generation of carbon dioxide in said reaction zone;
identifying a transition point after which the rate of oxidation of N-(phosphonomethyl)iminodiacetic acid is non-zero order;
estimating residual N-(phosphonomethyl)iminodiacetic acid concentration at a base point during non-zero order oxidation;
identifying an end point subsequent to the base point from a correlation of carbon dioxide generation with residual N-(phosphonomethyl)iminodiacetic acid in the reaction zone during non-zero order oxidation;
wherein the measured generation of carbon dioxide is adjusted to account for an estimate of carbon dioxide generated by oxidation of formaldehyde and formic acid in said reaction zone to provide an estimated conversion of N-(phosphonomethyl)iminodiacetic acid to N-(phosphonomethyl)glycine.

2. A method as set forth in claim 1 wherein identification of said transition point comprises measurement of the instantaneous rate of carbon dioxide generation, the instantaneous rate of oxygen consumption, or the instantaneous rate of heat generation in the reaction zone, said transition point being indicated by a decline in any of said instantaneous rates.

3. A method as set forth in claim 1 wherein the N-(phosphonomethyl)iminodiacetic acid concentration at said base point is estimated from cumulative carbon dioxide generation to that point as adjusted by an estimate of cumulative carbon dioxide attributable to oxidation of formaldehyde and formic acid.

4. A method as set forth in claim 1 wherein the N-(phosphonomethyl)iminodiacetic acid concentration at said base point is determined from analysis of a sample taken at the base point.

5. A method as set forth in claim 1 wherein the end point subsequent to the base point is estimated from cumulative CO 2 generation subsequent to the base point as adjusted by an estimate of the cumulative carbon dioxide generation subsequent to the base point that is attributable to oxidation of formaldehyde or formic acid.

6. A method as set forth in claim 1 wherein the end point subsequent to the base point is estimated from instantaneous CO 2 generation rates subsequent to the base point as adjusted by an estimate of the instantaneous carbon dioxide generation rates subsequent to the base point that are attributable to oxidation of formaldehyde or formic acid.

Assignees

• Haupfear Eric A
• Monsanto Technology Llc

Inventors

• Haupfear Eric A

Classifications

• C07F9/3813 Primary

  N-Phosphonomethylglycine; Salts or complexes thereof · CPC title

• G01N2201/1222

  Endpoint determination; reaction time determination · CPC title

• Y10T436/204998

  Inorganic carbon compounds · CPC title

• Y10T436/163333

  Organic [e.g., chemical warfare agents, insecticides, etc.] · CPC title

• G01N31/00

  Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods · CPC title