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

Patent metadata

Field	Value
Publication number	US-11067502-B2
Application number	US-201615198188-A
Country	US
Kind code	B2
Filing date	Jun 30, 2016
Priority date	Apr 1, 2005
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

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. One such method involves obtaining a series of Fourier transform infrared (“FTIR”) analyses of the PMIDA content of the aqueous reaction medium or a sample thereof during the course of the reaction. From a plurality of FTIR analyses, a projection is made of the batch reaction time or continuous oxidation residence time within the oxidation reaction zone at which a target conversion or end point may be anticipated to be attained or is attained.

First claim

What is claimed is:

1. A method for monitoring or detecting conversion of N-(phosphonomethyl)iminodiacetic acid to N-(phosphonomethyl)glycine or an intermediate for N-(phosphonomethyl)glycine during catalytic oxidation of N-(phosphonomethyl)iminodiacetic acid in an aqueous medium within an oxidation reaction zone, the method comprising:
introducing the aqueous medium containing N-(phosphonomethyl)iminodiacetic acid into said 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 catalytic oxidation of N-(phosphonomethyl)iminodiacetic acid and producing N-(phosphonomethyl)glycine;
obtaining a series of Fourier transform infrared (FTIR) analyses of the N-(phosphonomethyl)iminodiacetic acid content of the aqueous medium during the catalytic oxidation, wherein said series of FTIR analyses is obtained under non-zero order reaction conditions;
identifying a target conversion of N-(phosphonomethyl)iminodiacetic acid to N-(phosphonomethyl)glycine or said intermediate for N-(phosphonomethyl)glycine, and/or a target end point defined by a target residual N-(phosphonomethyl)iminodiacetic acid content; and
from said series of FTIR analyses, projecting a batch reaction time or continuous oxidation residence time within said oxidation reaction zone necessary to achieve said target conversion or said target end point; and
wherein said projecting is made on the basis of a substantially first order reaction and said batch reaction time or continuous oxidation residence time is projected based on straight line extrapolation on a logarithmic plot of remaining N-(phosphonomethyl)iminodiacetic acid concentration versus time.

2. A method as set forth in claim 1 wherein a kinetic rate constant for the catalytic oxidation of N-(phosphonomethyl)iminodiacetic acid is estimated from one or more of historical FTIR data, other analytical data or operational data obtained from laboratory and industrial oxidation reactions.

3. A method as set forth in claim 1 wherein said catalytic oxidation is conducted in a batch mode and a rate constant is estimated from a rate of decline in the reaction rate of the catalytic oxidation as a function of time as determined from a plurality of analyses taken during the course of the catalytic oxidation, or from a preceding batch.

4. A method as set forth in claim 3 wherein said rate constant is estimated from the rate of decline in the reaction rate as a function of time in a recently preceding batch.

5. A method as set forth in claim 1 wherein the catalytic oxidation is conducted in a continuous oxidation reaction zone.

6. A method a set forth in claim 5 wherein the catalytic oxidation is conducted in a continuous back mixed reaction zone, and the order of the catalytic oxidation is estimated from one or more of historical FTIR data, other analytical data or operational data obtained from laboratory and industrial oxidation reactions.

7. A method as set forth in claim 6 wherein the order of the catalytic oxidation is estimated from historical FTIR data, other analytical data or operational data obtained from recently preceding operations within said continuous back mixed reaction zone.

8. A method as set forth in claim 6 wherein a kinetic rate constant for the catalytic oxidation of N-(phosphonomethyl)iminodiacetic acid is estimated from one or more of historical HPLC data, FTIR data, other analytical data or operational data obtained from laboratory and industrial oxidation reactions.

9. A method as set forth in claim 6 wherein said operational data are selected from the group consisting of a rate of exothermic heat generation, a rate of oxygen consumption in the continuous back mixed reaction zone, a rate of generation of CO 2 in the continuous back mixed reaction zone, and combinations thereof.

10. A method as set forth in claim 6 wherein a kinetic rate constant for the catalytic oxidation of N-(phosphonomethyl)iminodiacetic acid is estimated from the N-(phosphonomethyl)iminodiacetic acid content of a feed solution entering said back mixed reaction zone and the N-(phosphonomethyl)iminodiacetic acid content of a reaction solution withdrawn from said back mixed reaction zone as a function of the residence time of said back mixed reaction zone.

Assignees

• Monsanto Technology Llc

Inventors

• Eaton David R
• Gavlick Walter K
• Haupfear Eric A

Classifications

• G01N33/0004

  Gaseous mixtures, e.g. polluted air · CPC title

• C07F9/3813 Primary

  N-Phosphonomethylglycine; Salts or complexes thereof · CPC title

• G01N31/22

  using chemical indicators (G01N31/02 takes precedence) · CPC title

• B01J2219/00202

  at the reactor outlet · CPC title

• Y10T436/207497

  Molecular oxygen · CPC title