Formaldehyde → N-(Carboxymethyl)-N-(phosphonomethyl)glycine

HRID 260570

Reaktionsgleichung

Reaktionsgleichung von HRID 260570
O.[P:2]([OH:5])([OH:4])[OH:3].S(=O)(=O)(O)O.[NH:11]([CH2:16][C:17]([OH:19])=[O:18])[CH2:12][C:13]([OH:15])=[O:14].[CH2:20]=O>>[P:2]([CH2:20][N:11]([CH2:16][C:17]([OH:19])=[O:18])[CH2:12][C:13]([OH:15])=[O:14])([OH:5])([OH:4])=[O:3]

Komponenten

6

Edukt 5

HCID 712FormaldehydeHCID 962WaterHCID 1118Sulfuric AcidHCID 8897Iminodiacetic acidHCID 107909Phosphorous acid

Produkt 1

HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycineAusbeute 61 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Water (17.3 g, 0.961 moles) was charged to a 250 ml three neck flask fitted with thermometer, condenser, dropping funnel and stirrer. Phosphorous acid (42.6 g, 0.514 moles), sulphuric acid (50.0 g, 0.500 moles--added over 10 minutes during which an exotherm from 20° C. to 60° C. was observed) and iminodiacetic acid (66.5 g,0.490 moles) were added to the stirred reaction flask. The reaction mixture was then heated to 120° C. and formaldehyde (48.2 g at 36.1% strength, 0.580 moles) was added over one hour. The temperature was maintained between 110° and 120° C. during addition. On complete addition, the reaction mixture was allowed to cool to 25° C. over 90 minutes and the reaction mixture was filtered. The filter cake was washed with water (57 ml) and the product was dried in a vacuum oven to yield 67.9 g of N-phosphonomethyliminodiacetic acid at 98.0% strength, equivalent to an isolated yield of 59.8%. The filtrates (128.0 g) and the water wash (66.0 g) were analysed at 13.7% and 5.5% N-phosphonomethyliminodiacetic acid respectively. This was equivalent to a total conversion yield of 78.9% N-phosphonomethyliminodiacetic acid.

Aufarbeitung

  1. customfitted with thermometer, condenser
  2. additionwere added to the stirred reaction flask
  3. temperatureThe temperature was maintained between 110° and 120° C. during addition
  4. additionOn complete addition
  5. temperatureto cool to 25° C. over 90 minutes
  6. filtrationthe reaction mixture was filtered
  7. washThe filter cake was washed with water (57 ml)
  8. customthe product was dried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-881c40ec38ba494984efd934042e0713
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05527953

Verknüpfte Notizen

Wird geladen…