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ACTION OF PHOSPHIDE OF SODIUM ON HALOID ETHERS. 191 
drop down the wide tube used as a reversed condenser in the preparation of 
the phosphide of sodium. The tap is turned so that the benzyl-chloride may 
drip fast on to the phosphide of sodium contained in the flask (in which it has 
been made), which is heated in an oil bath. Care must be taken, however, 
lest the benzyl-chloride run in too rapidly, as in that case the ebullition (caused 
by the reaction) may be so violent that liquid collects in the condensing tube 
and is blown out by the vapour. 
That reaction is occurring in the proper manner may be known by the 
change of colour of the phosphide of sodium from black to orange. It is 
advisable after the reaction has proceeded for some time, to remove the flask 
from the oil bath and to shake it vigorously ; but as the lower portions of the 
phosphide are apt to become superheated, the shaking must be done cautiously. 
PREPARATION OF TETRABENZYL-PHOSPHONIUM CHLORIDE. 
1 2 3 4 5 6 7 8 9 10 11 12 
Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. 
Benzyl-Chloride............, 100 | 160 200} 115 | 220} 220 |} 100 | 100 | 100 | 200 | 100 | 100 
RT Ole neactiesis cen sesnen ic'ceas 100 | 160 |Toluol|Toluol) 500 | 500 |100-40100-60)100-55)100-75/100-55|100-60 
PIDGIN. secs sinnesacenseanees 14 | 22°5 28 17 31 31 14 14 18 28 21 20 
Phosphorus.........:2s0000 6 21 26 15 28 28 9 8 ey 26 19 19 
Unacted on _ benzyl- | 
chloride and xylol... eee ove eee eee eee wee eee | 
Yield of (C,H,),PClt..... 12| 93 7 7 12 Flask broke 4 | 23 | 38 | 17 | 38 
Theoretical yield ..........) 88 | 141 176 | 101 193 | 193 | 88 88 88 176 88 88 
13 14 15 16 17 18 19 20 21 22 23 
Grms. | Grms.|Grms.| Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. | Grms. 
Benzyl-Chloride.........) 100 | 100 | 100 200 100 200 200 200 200 200 200 
PROLOG  ctiticessceceesssres 100-25)100-25| 100-25|245—200}120-100|200-170 200-180 230-205 220-175 220-178)/220-176 
SSEETIG dais sir nicis Saisie ase 20 20 20 35 20 40 40 40 40 40 40 
Phosphorus............... 19 19 19 33 19 38 38 38 38 38 38 
Unacted on benzyl- 
chloride and xylol 80 90 90 78 35 40 60 30 52 58 75 
Yield of (C,H,),PC1t..| 18 7 5 20 43 FOk ZO) eat AOecle «65x, p IBiyrlygl3y 
Theoretical yield .......| 88 88 88 176 88 176 176 176 176 176 176 
* In 7 and subsequent experiments a quantity of the xylol was distilled off after the preparation of the phosphide of 
sodium, and before the chloride of benzyl was allowed to act onit. The numbers after the sign — show how much of the 
xylol was thus distilled off. 
+ The chloride was squeezed in a cloth filter until it was as dry as possible and then weighed. 
