C. Friedel and J. M. Crafts on Etherification. 41 
the identity of the bodies. The quantity of these iodids which 
was obtai was, however, comparatively small; in each of 
the tubes the principal portion of the reaction was an ether, 
which was regained from the sulphuric acid employed in purify- 
ing the iodids, by the addition of water. 
he ether obtained in this manner was not pure, being mixed 
with a small quantity of the iodids, and with traces of the alco- 
hols, but it distilled in greater part at 100°-120°, and after a 
few fractionated distillations a large quantity of a product whose 
boiling point was near 110° was obtained. In order to rid this 
product of the iodids with which it was mixed, it was heated 
some time with sodium; the iodids were destroyed with forma- 
tion of iodid of sodium and the radicals ethyl and amyl. From 
these latter the ether was freed by repeated fractionated distilla- 
tion as far as possible, but the analyses below show that the 
body was not perfectly pure; the traces of these hydrocarbons 
which it contained was not, however, sufficient to leave any 
doubt as to its identity with the mixed oxyd of ethyl and amyl, 
On O. It distilled at 110°-118° (true boiling point =112°). 
; . 
“Analysis I is of the product obtained from the tube contain- 
ing iodid of amyl and common alcohol; analysis 11, of that ob- 
tained from iodid of ethyl and amylic alcohol. 
L IL Theory. 
PS iy ee 72°55 72°41 
iW = 1492. - ~. : 13°79 
The ether could only have contained a trace of an alcohol, but, 
as the action of sodium of a mixture of an alcohol with the 
iodid of the radical of another alcohol gives rise to a mixed 
ether, we repeated the experiment, taking care to destroy the 
alcohol more completely by repeated treatments with concentra- 
ted sulphuric acid before acting upon the iodid with sodium, but 
we did not observe that the quantity of mixed ether formed was 
diminished after this precaution had been taken. 
In the foregoing experiments common ether as well as amylic 
ether were formed, but in much smaller quantity than the mixed 
ether. The principal reaction which took place in the tubes is 
therefore expressed by the equation: 
nto? + RI = _fO + HL 
The iodhydric acid in presence of an excess of alcohol would 
| 
— 
~ 
co 
cm) 
ts rise to the formation of water and of the iodid of the alco- 
olic radical, | 
tO + Hl = BI + 4,0, 7 
and the iodid would in this manner be continually decomposed — 
Am. Jour. Sct.—Szconp Szrres, Vou. XL, No. 118.—Juty, 1865. 
6 : 
al 
