Reaction with Alcohols, Phenol and Amines

While red phosphorus (from P4 + PI3) gave only orange solids free of iodine when contacted with methanol or ethanol at room temperature for several days a mixture of the corresponding alkylphosphines and phosphonium salts was produced when white phosphorus was heated with methanol or ethanol at about 250 °C for several hours (Berthaud). 

Phenol did not react with red phosphorus at 300 °C in the absence of water but in the presence of small quantities of water, reaction at 250 °C gave small yields of phenylphosphine, diphenylphosphine, and phenylpho honic acid Larger amounts of water favor the formation of (PhO)3P=O  

White phosphorus in contact with ethylamine in a sealed tube at room temperature tons first red, then dark-red, and finally rives a black precipitate of approximate composition Pc.3 jH (C2HsNH2)o.26 - Other amines give apparently similar products Obviously the effect of amine consists mainly in the conversion of white phosphorus to another modification 

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