May 4, 1877.) 29 |Smith. 
CONTRIBUTIONS FROM THE LABORATORY OF THE UNIVERSITY OF 
PENNSYLVANIA. 
No. IX. 
Upon some new Chlorine Derivatives from Toluol. 
By Epear F. Smitru, Ph.D., ; 
ASSISTANT IN ANALYTICAL CHEMISTRY, UNIVERSITY OF PENNSYLVANIA. 
(Read before the American Philosophical Society, May 4, 1877.) 
The first of these derivatives which it is my intention to describe in the 
following lines was obtained by me some time ago, and also a description 
of it published (Inaugural Dissertation, Gottingen, 1876), but as it is in- 
timately connected with the subsequent work a brief description of its 
production and properties may probably not be amiss. 
PRODUCTION OF TOLUOLTRICHLORIDE OR BENZYLTRICHLORIDE. 
This was obtained in the usual manner, viz.: By the introduction of a 
calculated amount of dry chlorine into boiling Toluol. The liquid boiling 
at 218° C. was collected and treated as follows : 
FORMATION OF C,, Cl,g. 
The pure Benzyltrichloride was placed in a large flask and dried chlorine 
gas conducted into the liquid until it was no longer absorbed and the vacant 
space also filled with it, when the flask was tightly corked and exposed to 
the action of the sun-light. After standing a few days the green color of 
the chlorine had disappeared. The flask was again filled with the gas and 
this operation repeated, until the chlorine was apparently no longer ab- 
sorbed. The flask was now set in a rather cool place and allowed to re- 
main there forsome time. After standing several months I noticed that 
crystals had separated from the liquid. These were immediately brought 
upon a filter, washed thoroughly with water and then pressed between 
filter paper to remove any Benzyltrichloride that may have adhered to the 
crystal mass. After drying the compound by exposure to the air, it was 
pulverized and dissolved in chloroform, from which solution it crystallized 
in fine, colorless crystals, which after repeated re-crystallization fused at 
1520-1589 C. 
Properties. —The compound possesses an odor very similar to that of cam- 
phor, is insoluble in water and alcohol, but readily soluble in chloroform. It 
is volatile without decomposition. My attempts to affect the introduction of 
the NO, group were unsuccessful. Even with the aid of heat nitric acid 
is without any action. 
If the compound is allowed to crystallize slowly from a chloroform solu- 
tion, crystals may be obtained half an inch long and one-fourth of an inch 
broad. These have prism and dome faces. 
I never succeeded in obtaining the compound during summer, very 
probably because the Benzyltrichloride held it in solution. 
Numerous analyses made of the compound lead to the following formu- 
tan ib@'C],, =" (E,/C), © Ch). (C, Cl; C Cl,).  (C, Cl, C Ci). 
