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ACTION OF PHOSPHIDE OF SODIUM ON HALOID ETHERS. 185 
a substance which he also prepared by the action of terchloride of phos- 
phorus on mercury di-phenyl, 
PCl, + Hg(C,H;).=(C,H;)PCl, + HgCl(C,H,) . 
By the action of water on this body, phosphenylous acid is produced, 
(C,H;)PCl, + 2H,O =(C,H;)PO,H, +2HCl, 
and this when destructively distilled yields phenyl-phosphine—the phosphorus 
analogue of aniline, 
3 {(C,H);PO,H,} =(C,H,)PH,+2C;H, + 2HPO,. 
The same body results when hydriodate of phosphenyl-iodide (obtained by 
the action of hydriodic acid on phosphenyl-chloride) is decomposed with 
alcohol. 
We were led in the first instance to the experiments to be presently 
described by the difficulty which one of us had experienced in preparing 
triethyl-phosphine on the large scale. Hormann’s later method had been at 
first resorted to, but in spite of numerous experiments, it had led to no satis- 
factory results. The pressure produced when alcohol and iodide of phos- 
phonium are heated together is enormous, especially at the high temperature 
(180° C.) at which they react, and in almost nine cases out of ten it was found 
that the sealed tubes burst. , 
Nor is the other process for preparing triethyl-phosphine, viz., by treating 
zinc-ethyl with terchloride of phosphorus, a simple operation. The preparation 
of zinc-ethyl is expensive and troublesome, and although it reacts readily with 
the terchloride, the reaction is not so simple as might be expected. Scarcely 
50 per cent. of the theoretical quantity of crude phosphine can be obtained, 
and this crude product contains impurities in considerable quantities, which 
are very difficult to remove. The preparation of triethyl-phosphine is in fact 
an expensive, uncertain, and troublesome operation. 
Such being the case, and one of us requiring large quantities of it, the 
question naturally presented itself—Is there no simpler and less expensive 
process for preparing a tertiary phosphine? It seemed to us that one of the 
processes—and in fact the earliest—for preparing these bodies ought to be an 
extremely good one, if the difficulties attending its general application could be 
removed. The process to which we allude depends upon the ease with which 
metallic phosphides can be formed, and the readiness with which haloid ethers 
act on them. As before stated, THENARD, Beruz, Canours, HOFMANN and 
others, have worked with this process, but it has not met with great favour, 
and was abandoned by Hormann (who employed phosphide of sodium) on 
