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Methylphosphonic acid

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Through Hydrolysis

Lab · Class 10–11Equilibrium

Preparation

Methylphosphonic acid can be prepared from triethylphosphite by first using a Michaelis-Arbuzov reaction to generate the phosphorus(V) centre:

CH3Cl + P(OC2H5)3 → CH3PO(OC2H5)2 + C2H5Cl

The resulting dialkylphosphonate is then treated with chlorotrimethylsilane before hydrolysis of the siloxyphosphonate to generate the desired product.

CH3PO(OC2H5)2 + 2 Me3SiCl → CH3PO(OSiMe3)2 + 2 C2H5Cl
CH3PO(OSiMe3)2 + 2H2O → CH3PO(OH)2 + 2 HOSiMe3

The reaction pathway proceeds via the siloxyphosphonate intermediate due to the difficulty in directly hydrolysing dialkylphosphonates. Katritzky and co-workers published a one-pot synthesis of methylphosphonic acid in 1989.

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