ACTION OF PHOSPHIDE OF SODIUM ON HALOID ETHERS. 201 
with boiling alcohol, and adding water to the filtered solution, small lemon- 
yellow plates separated as the solution cooled. They were not analysed. 
Oxalate of Tetrabenzyl- Phosphonium.—On adding excess of oxalic acid to a 
dilute and hot solution of the base, and then allowing the mixture to cool, long 
needles separated. The salt was analysed by drying at 100° C., and determining 
oxalic acid in the dried compound by precipitation with chloride of calcium, 
the oxalate of calcium being eventually ignited and converted into quicklime. 
0-741 gave 0-088 Ca0=—0:1383 C,0,=17°9 per cent. 
0:70 lost)» 0-029. H,0= BT . 
Calculated for 
Obtained. 
(C,H.,,),PHC,0O, . 
C0), a Ted : 4 =) waleeil 
{(C,H,),PHC,0,},H,0 . 
HOT: .. Ok é é 5 Be 
Acetate of Tetrabenzyl-Phosphonium.—This salt is the most soluble of any 
of the compounds of tetrabenzyl-phosphonium which we have examined. It is 
obtained by the action of the chloride on acetate of silver, and crystallises from 
alcohol with difficulty. It was not analysed. 
Chlorate of Tetrabenzyl-Phosphonium.—This salt was prepared by the action 
of chlorate of barium on the acid sulphate. It crystallises in long needles from 
a moderately concentrated solution. Heated above its melting point, it puffs. 
Examination of the Residues from the Preparation of Chloride of Tetrabenzyl- 
Phosphonium. 
After extracting the chloride of the phosphonium from the product of 
action of chloride of benzyl on phosphide of sodium (by boiling the latter 
repeatedly with water) a solid orange-coloured mass remains, which contains 
large quantities of amorphous phosphorus, and also organic phosphorus 
compounds. 
We thought it possible, if not indeed probable, that these would contain 
tribenzyl-phosphine, for it is only natural to suppose that that body is first 
formed in the reaction, and is only converted into the phosphonium compound 
by the continued action of the chloride of benzyl. If this were the case some 
of the phosphine might, we considered, remain unacted upon, and would be 
found in the residues. 
Moreover, we thought that phosphides of sodium of a different composition 
from the tri-sodium phosphide might be formed along with that body by the 
