ACTION OF PHOSPHIDE OF SODIUM ON HALOID ETHERS, 187 
methyl- and ethyl-phosphines. His first attempts were made with the view of 
obtaining a phenyl-phosphine analogous to aniline, a substance highly interest- 
ing from a theoretical point of view. 
To obtain this body he heated, under varying conditions, phenyl-chloride 
and iodide of phosphonium ; but the experiments did not lead to a successful 
result, the phenyl-chloride becoming reduced to benzol, which even at high 
temperatures was not further acted upon. ‘That the reaction did not proceed in 
the desired manner was, as he says, not surprising, considering the inertness of 
chloride of phenyl and the fact that aniline cannot be obtained by acting 
on it with ammonia. 
Equally unsuccessful were his efforts to obtain the tertiary phosphine and 
the quaternary compound by the action of phenol upon iodide of phosphonium, 
though phosphorised bodies resulted, the nature of which he did not ascertain. 
Experiments to obtain a phosphorised toluidine led to no successful 
issue ; but, on the other hand, the preparation of a phosphorus analogue of 
benzylamine presented no difficulty, as indeed he did not doubt, considering 
the readiness with which chloride of benzyl reacts with ammonia. 
Benzyl Phosphine, C,H,PH,.—This body is formed when chloride of 
benzyl (which may be employed in the crude condition) is heated for six hours 
at a temperature of 160° with a mixture of phosphonium iodide and zinc 
oxide. The substances are taken in the proportions of 2 molecules benzyl 
chloride, 2 of phosphonium iodide, and 1 of zinc oxide. 
When complete reaction has occurred the sealed tubes in which the mixture 
has been heated contain a white crystalline mass. On opening them a large 
quantity of phosphuretted hydrogen is evolved. On distilling the product of 
the reaction with water a heavy, oily liquid passes over of highly characteristic 
odour. This is separated, dried with caustic potash, and distilled in hydrogen. 
The thermometer rises to 180°, and then remains stationary, whilst a considerable 
quantity of a colourless, highly refractive liquid distils. | This is monobenzyl- 
phosphine, whilst the lower boiling fraction consists mainly of toluol, and the 
residue in the retort contains dibenzyl-phosphine and other products. <A 
simple distillation of the crude benzyl-phosphine thus obtained gives the pure 
body boiling at 180°C. In its properties it resembles in the main other 
primary phosphines. It oxidises in contact with the air, its temperature 
rising to 100° C., thick white vapours being formed. It is insoluble in water, 
but easily soluble in alcohol and ether. It forms a colourless crystalline 
hydriodate, only slightly soluble in fuming hydriodic acid, and which, like other 
salts of primary phosphines, decomposes in contact with water into hydriodic 
acid and the free base. Monobenzyl-phosphine also combines with hydro- 
chloric acid, and gives a yellow insoluble chloro-platinate. 
