Dr. Simpson on the Action of Acids on Glycol. 71 
tate of glycol and diethylglycol, I resolved to try the action of chlor- 
acetine on ethylate of soda, thinking that probably the body in 
question might be generated by the following reaction :— 
C,H, C, H, 
C.H. 0. bor N } O,=C, H, 0, } 0,+NaCl. 
a 
C, H, 
Cl 
In order to settle this point, I exposed equivalent quantities of 
these bodies in a sealed balloon to the temperature of a water-bath 
for about two hours. My expectations, however, were not realized. 
On opening the balloon, I found that the reaction had proceeded too 
far, acetic ether having been formed along with the chloride of 
sodium. 
Action of Hydrochloric and Butyric Acids on Glycol.—Formation of 
Chlorbutyrine of Glycol. 
This compound is prepared in the same manner as its homologue, 
namely by transmitting a stream of dry hydrochloric acid gas 
through a mixture of equivalent quantities of butyric acid and glycol, 
maintained at the temperature of 100°C. As soon as the reaction 
is finished, the product is well washed with water, dried by means 
of chloride of calcium, and distilled. The greater part passes over 
between 160° and 182°. This must be rectified, and the quantity dis- 
tilling between 175° and 182° collected apart. This gave, on analysis, 
results agreeing with the formula c i O } O,, as will be seen from 
8 vp agg 
the following table :— Cl 
—— 7 
i Il. 
piy.8 547-84 47°76 or 
Hjiep 7:30 7°31 
O, .... 21°28 ss ire 
Cl .... 23°58 ai 23°88 
The reaction, to which the formation of this body is due, may be 
thus explained :— 
C, H, C,H,0, POR 
a} Ot : | 0,4HC1=6' Ff", | 0.4410. 
Cl 
Chlorbutyrine of glycol, as I may call this compound, has a pun- 
gent and somewhat bitter taste. It boils at about 180°. Its specific 
gravity at zero is 10854. It is insoluble in water, but freely soluble 
in alcohol. It is decomposed with difficulty by a boiling solution of 
potash, but readily by solid potash,—chloride of potassium, butyrate 
of potash, and oxide of ethylene, being formed. 
I have ascertained that acetobutyrate of glycol, the ether I have 
already described, can be prepared from this body as well as from 
chloracetine, by exposing it to the action of acetate of silver. The 
process is the same as that I have already given, with this difference, 
that the reacting bodies must not be heated above 150°C. The 
