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WO1996020944A1 - Procede de preparation de n-phosphomethylglycine - Google Patents

Procede de preparation de n-phosphomethylglycine Download PDF

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Publication number
WO1996020944A1
WO1996020944A1 PCT/EP1995/005095 EP9505095W WO9620944A1 WO 1996020944 A1 WO1996020944 A1 WO 1996020944A1 EP 9505095 W EP9505095 W EP 9505095W WO 9620944 A1 WO9620944 A1 WO 9620944A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
activated carbon
cooh
temperatures
reaction
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.)
Ceased
Application number
PCT/EP1995/005095
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Priority to AU43471/96A priority Critical patent/AU4347196A/en
Publication of WO1996020944A1 publication Critical patent/WO1996020944A1/fr
Anticipated expiration legal-status Critical
Ceased 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 Table
    • 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 ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or 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

Definitions

  • the invention relates to a new process for the preparation of N-phosphonomethylglycine, a compound known to be herbicidally active
  • N-phosphonomethyl-glycine is obtained if N-phosphonomethyl-iminodiacetic acid is oxidized with oxygen in the presence of water using an activated carbon catalyst (cf. DE-A 2519388 and EP-A 019445; cf. also EP -A 125363 and US-P 4397676).
  • an activated carbon catalyst cf. DE-A 2519388 and EP-A 019445; cf. also EP -A 125363 and US-P 4397676.
  • the yields vary greatly and the product is usually more or less contaminated by the starting material or by-products.
  • the activated carbon catalysts used contain further, catalytically active constituents.
  • the N-phosphonomethylglycine of the formula (I) can be obtained in good yields and in high purity by the process according to the invention in a technically simple manner using inexpensive auxiliaries.
  • the method according to the invention thus represents a valuable enrichment of the prior art.
  • the process according to the invention is carried out using oxygen.
  • atmospheric oxygen can be used.
  • pure oxygen that is to say largely freed from the other constituents of the air, is preferably used
  • the process according to the invention is carried out in the presence of activated carbon as a catalyst.
  • activated carbon Practically all known types of activated carbon come into consideration here, but it is not necessary to use activated carbon which is activated, that is to say which contains additional reaction-accelerating constituents, such as, for example, No ⁇ t pure activated carbon ("p A") can also be used as a catalyst in the process according to the invention
  • the process according to the invention is carried out in the presence of a suitable basic reaction auxiliary.
  • a suitable basic reaction auxiliary All customary inorganic or organic bases are suitable. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates , such as lithium, sodium, potassium or calcium hydride, lithium, sodium or potassium amide, sodium or potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropoxide, sodium - or potassium tert-butoxide, sodium or potassium hydroxide, ammonium hydroxide, sodium, potassium or calcium acetate,
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 20 ° C and 120 ° C, especially at temperatures between 80 ° C and 1 10 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • 0.5 to 5 mol, preferably 1 to 3 mol of oxygen, 0.1 to 2 mol, preferably 0.5 to 1 mol of basic, are generally employed per mol of starting compound of the formula (II) Reaction aids, 10 to 200 g, preferably 20 to 100 g of activated carbon and 0.5 to 3 liters, preferably 1 to 2 liters of water.
  • the N-phosphonomethyl-iminodiacetic acid of the formula (II) is initially introduced into water and the basic reaction auxiliary is added with slow heating. After practically a clear solution has been formed by briefly stirring this mixture at elevated temperature, the activated carbon is added and, at a further elevated temperature, oxygen is passed in via a frit over a period of several hours. When the reaction has ended, the mixture is filtered, if appropriate under reduced pressure, and the filtrate is acidified and concentrated with a strong acid, such as hydrochloric acid. The residue is stirred with a little water and the crystalline product isolated by suction. Manufacturing example
  • N-phosphonomethyl-iminodiacetic acid 22.7 g (0.10 mol) of N-phosphonomethyl-iminodiacetic acid are placed in 200 ml of water and, with slow warming to 90 ° C., 9.0 g (0.05 mol) of guanidine carbonate are added after heating for 15 minutes 90 ° C become 5.0 g
  • Activated carbon is added and oxygen is introduced into the boiling mixture (approx. 105 ° C) for three hours via a frit. Then it is cooled to room temperature (approx. 20 ° C), concentrated to approx. Half the volume and sucked off

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)

Abstract

On obtient le principe actif herbicide N-phosphométhylglycine (I): (HO)2P(O)-CH2-NH-CH2-COOH, de grande pureté, à de bons niveaux de rendement, par réaction d'acide N-phosphométhyliminodiacétique de la formule (II): (HO)2P(O)-CH2-N(CH2-COOH2), avec de l'oxygène, en présence de charbon actif servant de catalyseur, en présence d'un auxiliaire de réaction basique et en présence d'eau servant de diluant, à des températures comprises entre 0 et 150 °C. On utilise de préférence du carbonate de guanidine comme auxiliaire de réaction et du charbon actif pas particulièrement activé ('p.A.'), comme catalyseur.
PCT/EP1995/005095 1995-01-04 1995-12-22 Procede de preparation de n-phosphomethylglycine Ceased WO1996020944A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU43471/96A AU4347196A (en) 1995-01-04 1995-12-22 Process for producing n-phosphonomethyl glycine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1995100121 DE19500121A1 (de) 1995-01-04 1995-01-04 Verfahren zur Herstellung von N-Phosphonomethylglycin
DE19500121.4 1995-01-04

Publications (1)

Publication Number Publication Date
WO1996020944A1 true WO1996020944A1 (fr) 1996-07-11

Family

ID=7750987

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/005095 Ceased WO1996020944A1 (fr) 1995-01-04 1995-12-22 Procede de preparation de n-phosphomethylglycine

Country Status (3)

Country Link
AU (1) AU4347196A (fr)
DE (1) DE19500121A1 (fr)
WO (1) WO1996020944A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999058537A1 (fr) * 1998-05-14 1999-11-18 Calgon Carbon Corporation Procede de production de n - phosphonomethylglycine a partir d'acide n - phosphonomethyliminodiacetique a l'aide de carbone catalytique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5942643A (en) * 1998-05-14 1999-08-24 Calgon Carbon Corporation Method for the manufacture of N-phosphonomethylglycine from N-phosphonomethyliminodiacetic acid using a low temperature catalytic carbon

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2519388A1 (de) * 1974-05-01 1975-11-13 Monsanto Co Verfahren zur herstellung von n-phosphonmethylglycin
US4147719A (en) * 1976-12-20 1979-04-03 Monsanto Company Process for producing N-phosphonomethylglycine salts
EP0088180A1 (fr) * 1982-03-08 1983-09-14 Geshuri Laboratories Ltd. Dérivés de la N-phosphonométhylglycine
EP0125363A1 (fr) * 1983-05-17 1984-11-21 Geshuri Laboratories Ltd. Procédé pour préparer la N-phosphonométhylglycine acide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2519388A1 (de) * 1974-05-01 1975-11-13 Monsanto Co Verfahren zur herstellung von n-phosphonmethylglycin
US4147719A (en) * 1976-12-20 1979-04-03 Monsanto Company Process for producing N-phosphonomethylglycine salts
EP0088180A1 (fr) * 1982-03-08 1983-09-14 Geshuri Laboratories Ltd. Dérivés de la N-phosphonométhylglycine
EP0125363A1 (fr) * 1983-05-17 1984-11-21 Geshuri Laboratories Ltd. Procédé pour préparer la N-phosphonométhylglycine acide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999058537A1 (fr) * 1998-05-14 1999-11-18 Calgon Carbon Corporation Procede de production de n - phosphonomethylglycine a partir d'acide n - phosphonomethyliminodiacetique a l'aide de carbone catalytique

Also Published As

Publication number Publication date
AU4347196A (en) 1996-07-24
DE19500121A1 (de) 1996-07-11

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