368 On the Action of Chlorine on Cinnamic Acid. 



vjipour, which affects the eyes strongly, is given off. When the 

 liquid is concentrated and allowed to cool, the oil is found to 

 be converted into a crystalline mass. The crystals were pu- 

 rified by being repeatedly crystallized ; they had a strong acid 

 reaction and were very soluble, both in hot water and in al- 

 cohol, out of which liquids they crystallized very readily. 

 When dried at 212° F. and subjected to analysis, 0*2128 grni. 

 substance gave 0-388 CO. and 0-061 HO. '. '"V'^"" ""'J^' 



Lalculated numbers. ^ ^ j ... 



Atoms, per cent. Fount!. •'"'/'^^ 



Carbon . 14- 50-25 49-72C*^-> ''••"' 



Hydrogen "'5"*' u^-ggijayuinruj ud j^^jgn bttiitit, 

 Nitroffen . ■'! ■ '^''g**?^ ■''"' >ilni'(um d-jum ,iut 

 Oxygen . 8 38-29 * thfyziv vlJaisloJ 



i 00-00 

 The silver salt was prepared by neutralizing the acid with 

 ammonia and precipitating the solution with nitrate of silver. 

 The salt formed a rather bulky precipitate. 



a. 0-2225 of the silver salt gave 0-0844 metallic silver 

 = 38-83 per cent, oxide; the calculated quantity is 39"12:|ier 

 cent, oxide. 



b. 0-2985 of the silver salt gave 0-329 carbonic acid apd 

 0*041 water. 



It is evident from the results of these analyses that the acid 

 and the salt have precisely the composition of nitrobenzoic 

 acid and its silver salt, with the character of which substances 

 they exactly correspond. I am induced to believe, therefore, 

 that the oil is essentially a carburetted hydrogen belonging to 

 the benzoic acid series, in which variable quantities of the hy- 

 drogen are replaced by chlorine ; and that the small quantity 

 of oxygen it contains, amounting in some instances to little 

 more than two per cent., is the result of foreign admixture. 

 The most probable source of this impurity is a little oil of 

 bitter almonds, for, so far as we know, oil of bitter almonds is 

 always generated whenever cinnamic acid is treated with an 

 oxidizing agent; at least it is so when cinnamic acid is boiled 

 with peroxide of lead, with chromic acid, or with sulphuric 

 acid and peroxide of manganese, or any other hy peroxide. 

 This view of the constitution of the chlorinated oil is strongly 

 confirmed by the effect of nitric acid upon it, which, as we 

 have seen, converts it into nitrobenzoic acid. Now nitric acid, 

 as is well known, also converts oil of bitter almonds into nitro- 



