CA2401248A1 - Method for the production of n-(phosphonomethyl)glycine - Google Patents

Method for the production of n-(phosphonomethyl)glycine Download PDF

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Publication number
CA2401248A1
CA2401248A1 CA002401248A CA2401248A CA2401248A1 CA 2401248 A1 CA2401248 A1 CA 2401248A1 CA 002401248 A CA002401248 A CA 002401248A CA 2401248 A CA2401248 A CA 2401248A CA 2401248 A1 CA2401248 A1 CA 2401248A1
Authority
CA
Canada
Prior art keywords
phosphonomethyl
glycine
reaction solution
mother liquor
catalyst
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002401248A
Other languages
French (fr)
Other versions
CA2401248C (en
Inventor
Martin Hitzler
Franz Thalhammer
Benedikt Hammer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Technology LLC
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2401248A1 publication Critical patent/CA2401248A1/en
Application granted granted Critical
Publication of CA2401248C publication Critical patent/CA2401248C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof

Abstract

The invention relates to a method for producing N-(phosphonomethyl)glycine involving the following steps: (a) oxidizing N-(phosphonomethyl)iminodiacetic acid (PMIDA) with peroxides or oxygen in an aqueous medium and in the presence of a heterogeneous catalyst at a temperature ranging from 50 to 150 °C; (b) subsequently separating the solid catalyst out of the aqueous reaction suspension of step (a); (c) concentrating the clear reaction solution from step (b), especially by evaporation, and; (d) separating the N-(phosphonomethyl)glycine out of the concentrated reaction solution from step (c), especially by filtration. According to the invention, the aqueous reaction solution from step (d) (mother liquor) is returned with small amounts of N-(phosphonomethyl)glycine and byproducts to step (b) (catalyst separation) and/or to step (c) (concentration). This results in distinctly increasing the yield with a constant product purity and in noticeably reducing the amount of mother liquor.
CA002401248A 2000-02-19 2001-02-16 Method for the production of n-(phosphonomethyl)glycine Expired - Lifetime CA2401248C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10007702A DE10007702A1 (en) 2000-02-19 2000-02-19 Process for the preparation of N- (phosphonomethyl) glycine
DE10007702.1 2000-02-19
PCT/EP2001/001749 WO2001060830A1 (en) 2000-02-19 2001-02-16 Method for producing n-(phosphonomethyl)glycine

Publications (2)

Publication Number Publication Date
CA2401248A1 true CA2401248A1 (en) 2001-08-23
CA2401248C CA2401248C (en) 2005-09-20

Family

ID=7631612

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002401248A Expired - Lifetime CA2401248C (en) 2000-02-19 2001-02-16 Method for the production of n-(phosphonomethyl)glycine

Country Status (11)

Country Link
US (1) US6730813B2 (en)
EP (1) EP1257557B1 (en)
CN (1) CN1177851C (en)
AR (1) AR027414A1 (en)
AT (1) ATE249469T1 (en)
AU (1) AU2001262077A1 (en)
BR (1) BR0108489B1 (en)
CA (1) CA2401248C (en)
DE (2) DE10007702A1 (en)
DK (1) DK1257557T3 (en)
WO (1) WO2001060830A1 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE60115019T2 (en) * 2000-05-22 2006-08-03 Monsanto Technology Llc. REACTION SYSTEMS FOR THE PREPARATION OF N- (PHOSPHONOMETHYL) GLYCINE COMPOUNDS
ATE382626T1 (en) * 2003-09-17 2008-01-15 Monsanto Technology Llc METHOD FOR RECOVERING A CRYSTALLINE PRODUCT FROM A SOLUTION
TW200624151A (en) * 2004-11-12 2006-07-16 Monsanto Technology Llc Recovery of noble metals from aqueous process streams
CN101583425A (en) * 2005-02-17 2009-11-18 孟山都技术公司 Transition metal-containing catalysts and catalyst combinations including transition metal-containing catalysts and processes for their preparation and use as oxidation catalysts
EP1853115B1 (en) 2005-03-04 2019-01-09 Monsanto Technology, LLC Mitigating necrosis in transgenic glyphosate-tolerant cotton plants treated with herbicidal glyphosate formulations
US7771494B2 (en) * 2007-01-31 2010-08-10 Monsanto Technology Llc Process for selective removal of water and impurities from N-(phosphonomethyl)glycine
CN101440106B (en) * 2008-12-19 2012-02-29 安徽锦邦化工股份有限公司 Novel process for recovering waste acid from glyphosate production
CN107884375B (en) * 2017-11-10 2020-10-16 华南师范大学 Method and kit for detecting ferric ions
CN111333519A (en) * 2020-03-11 2020-06-26 陈兴华 Comprehensive treatment and resource recycling method for glyphosate mother liquor
CN113185548A (en) * 2021-05-10 2021-07-30 浙江新安化工集团股份有限公司 Glyphosate synthesis method for improving utilization rate of dimethyl phosphite

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL285361A (en) 1961-11-13 1900-01-01
US3969398A (en) * 1974-05-01 1976-07-13 Monsanto Company Process for producing N-phosphonomethyl glycine
NL7713959A (en) * 1976-12-20 1978-06-22 Monsanto Co PROCESS FOR PREPARING N-PHOSPHONOMETHYLGLYCIN SALTS.
US4579689A (en) 1985-02-11 1986-04-01 Monsanto Company Oxidation with coated catalyst
US4582650A (en) 1985-02-11 1986-04-15 Monsanto Company Oxidation with encapsulated co-catalyst
US4853159A (en) * 1987-10-26 1989-08-01 Monsanto Company Process for producing N-phosphonomethylglycine
US4851131A (en) 1987-12-31 1989-07-25 Monsanto Company Process for treating glyphosate process waste streams
EP0413672B1 (en) 1989-08-17 1995-02-15 Monsanto Company Process for purifying N-phosphonomethylglycine
US5087740A (en) 1989-08-17 1992-02-11 Monsanto Company Process for purifying N-phosphonomethylglycine
ES2021229A6 (en) * 1990-03-12 1991-10-16 Ercros Sa Preparation of n-phosphonomethylglycin by oxidation of n-phosphonomethyliminodiacetic acid.
US5948938A (en) * 1995-03-07 1999-09-07 Sankyo Company, Limited Process for preparing N-phosphonomethylglycine
US6365772B1 (en) * 1995-05-30 2002-04-02 Hampshire Chemical Corp. Facile synthesis of phosphonomethylglycine from phosphonomethyliminodiacetic acid
US5606107A (en) 1995-06-07 1997-02-25 Monsanto Company Formic acid and formaldehyde destruction in waste streams
GB9515265D0 (en) 1995-07-25 1995-09-20 Zeneca Ltd Chemical process
US5962729A (en) * 1998-05-14 1999-10-05 Calgon Carbon Corporation Method for the manufacture of N-phosphonomethylglycine from N-phosphonomethyliminodiacetic acid using a catalytic carbon
DE19938622C2 (en) 1999-08-14 2002-10-02 Sueddeutsche Kalkstickstoff Process for the preparation of N- (phosphonomethyl) glycine
HUP0203589A3 (en) * 1999-12-21 2003-04-28 Monsanto Technology Llc Saint Process for the oxidation of formil acid or formaldehide and process for making n-(phosphonomethyl)glycine or salt thereof in the presente of a supple mental promoter in conjunction with a carbonsupported, noble-metal-containg catalyst
US6670505B1 (en) 2000-03-07 2003-12-30 Eastman Chemical Company Process for the recovery of organic acids from aqueous solutions
DE60115019T2 (en) 2000-05-22 2006-08-03 Monsanto Technology Llc. REACTION SYSTEMS FOR THE PREPARATION OF N- (PHOSPHONOMETHYL) GLYCINE COMPOUNDS

Also Published As

Publication number Publication date
AU2001262077A1 (en) 2001-08-27
AR027414A1 (en) 2003-03-26
US20030050503A1 (en) 2003-03-13
EP1257557A1 (en) 2002-11-20
US6730813B2 (en) 2004-05-04
DE10007702A1 (en) 2001-08-23
EP1257557B1 (en) 2003-09-10
WO2001060830A1 (en) 2001-08-23
DK1257557T3 (en) 2004-01-19
BR0108489B1 (en) 2012-09-04
DE50100607D1 (en) 2003-10-16
CN1411464A (en) 2003-04-16
CA2401248C (en) 2005-09-20
BR0108489A (en) 2003-04-22
CN1177851C (en) 2004-12-01
ATE249469T1 (en) 2003-09-15

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Effective date: 20210216

MKEX Expiry

Effective date: 20210216