HYDROXYMETHYL PHOSPHORUS DERIVATIVES FROM TETRAKIS(HYDROXYMETHYL) PHOSPHONIUM CHLORIDE. REACTION WITH LEAD CARBONATE AND OXIDE

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Abstract
A novel and convenient method has been developed for the preparation of tris(hydroxy-methyl) phosphine oxide (THPO) from tetrakis (hydroxymethyl) phosphonium chloride (THPC). The method consists essentially of oxidative deformylation of THPC with lead carbonate in n-propyl alcohol. The reaction is facilitated by azeotropic distillation of di-n-propylformal and n -propyl alcohol.The reaction of THPC with lead carbonate as well as with lead oxide has been studied in detail in aqueous solution and in n-propyl alcohol. The reaction proceeds via the initial formation of tetrakis(hydroxymethyl) phosphonium hydroxide (THPOH) followed by deformylation to tris (hydroxymethyl) phosphine (THP). THP then undergoes oxidation by air as well as by lead carbonate or oxide to THPO. If air is bubbled through the mixture at elevated temperatures, atmospheric oxidation predominates with little or no oxidation by the lead compound.Depending upon the reaction conditions, a phosphonium hydroxide, a phosphine, or a phosphine oxide are products of the reaction of tetrakis(hydoxymethyl) phosphonium chloride with lead carbonate or oxide.

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