Glyphosate → Glyphosate

HRID 1413643Notes

Reaction equation

HRID 1413643 reaction equation
C1(=O)OC(=O)C=C1.[OH-].[Na+:9].[P:10]([CH2:14][NH:15][CH2:16][C:17]([OH:19])=[O:18])([OH:13])([OH:12])=[O:11].C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+:51].[Na+].[Na+].C(CN(CP(O)(O)=O)C(=O)/C=C\C(O)=O)(O)=O>CCOCC>[Na:9][Na:51].[P:10]([CH2:14][NH:15][CH2:16][C:17]([OH:19])=[O:18])([OH:13])([OH:12])=[O:11]

Participants

8

Reactant 5

HCID 3496GlyphosateHCID 7923Maleic Anhydride2×HCID 14798Sodium Hydroxide2×HCID 164825TartrazineHCID 88760695HCID 88760695, compound

Product 2

HCID 3496GlyphosateHCID 141233Disodium

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the disodium salt of N-phosphonomethylglycine is prepared as described in Example I and 11.0 grams (0.11 mole) of finely ground maleic anhydride is added with stirring. Some sodium hydroxide is added to keep the pH at almost 9, and a small portion of ether is added to help dissolve particles of the anhydride. Stirring is continued for several days, and 2.0 or 4.0 gram portions of maleic anhydride are added until no further N-phosphonomethylglycine remains in the reaction mixture. During this period, small portions of sodium hydroxide are added as needed to maintain a pH of about 8. When reaction is complete, the mixture is filtered, rinsed with water, concentrated and then dried. The product, containing disodium maleate by-product, is obtained as a colorless glass, and it is identified by nuclear magnetic resonance (nmr) as the trisodium salt of N-carboxymethyl-N-(phosphonomethyl)maleamic acid. ##STR4##

Workup

  1. additionis added
  2. stirringStirring
  3. waitis continued for several days
  4. waitDuring this period
  5. temperatureto maintain a pH of about 8
  6. customWhen reaction
  7. filtrationthe mixture is filtered
  8. washrinsed with water
  9. concentrationconcentrated
  10. customdried
  11. additionThe product, containing disodium maleate by-product
  12. customis obtained as a colorless glass, and it

Sources & evidence

ORD record
ord-0593874fef0944228fa76d047d190eac
Source dataset
uspto-grants-1981_02
Patent number
US04251257

Reaction notes

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