Methane → Glyphosate

HRID 461577Notes

Reaction equation

HRID 461577 reaction equation
C(OCC)C1OC1.C.[Na:9][Na:10].C(OCC(O)C[N:17]([CH2:22][P:23]([OH:26])([OH:25])=[O:24])[CH2:18][C:19]([OH:21])=[O:20])C.[H][H].[P]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[Na:9][Na:10].[P:23]([CH2:22][NH:17][CH2:18][C:19]([OH:21])=[O:20])([OH:26])([OH:25])=[O:24]

Participants

10

Reactant 6

HCID 297MethaneHCID 19919Oxirane, 2-(ethoxymethyl)-2×HCID 141233DisodiumHCID 5462309PhosphorusHCID 22765467HCID 22765467, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 3496GlyphosateHCID 141233Disodium

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A solution of the disodium salt of N-phosphonomethylglycine is prepared as in Example 1. To 27.5 grams (0.0437 mole) of the solution is added 5.1 grams (0.05 mole) of ethyl glycidyl ether. The solution is diluted with 30 ml. water and 1 drop of Aliquat 336 phase-transfer catalyst solution is added. It is then rotated on a polymer wheel for 5 days, treated with 1.0 gram of ethyl glycidyl ether, rotated for 10 days, then warmed with charcoal and filtered to remove resinous material. The solution is then rotoevaporated to dryness, and the solid is redried over potassium hydroxide pellets at 100° C. and <1 mm. Hg. The product, obtained as a tan, brittle foamed glass, is the disodium salt of N-(3-ethoxy-2-hydroxy-1-propyl)-N-phosphonomethylglycine. Elemental analysis shows 31.15% carbon, 5.62% hydrogen and 8.87% phosphorus as against calculated values of 30.49%, 5.12% and 9.83% for C8H16NNa2O7P.

Workup

  1. additionThe solution is diluted with 30 ml
  2. waitrotated for 10 days
  3. filtrationfiltered
  4. customto remove resinous material
  5. dry with materialthe solid is redried over potassium hydroxide pellets at 100° C.
  6. customThe product, obtained as a tan, brittle

Sources & evidence

ORD record
ord-b4932c528d584db0997ebb5ccb03cfce
Source dataset
uspto-grants-1977_12
Patent number
US04063922

Reaction notes

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