192 . EXAMINATION OF A NAPHTHA PROM LIME-SOAP. 



is doubtless toluole mixed with a portion of one of the more highly hydrogenized 

 substances which occur with it in the crude naphtha. 



Attempts to obtain a purer product by first converting portions of the crude frac- 

 tions 108°-109° and 111 -112° into nitro-toluole led to no useful result, the mixture 

 of nitro-products, etc., obtained being quite unmanageable, at least when in small quan- 

 tity, as in the present case. 



A portion of the product boiling at 111 (corrected) was converted into nitro-toluole 

 and toluidin, and the latter was then heated with arsenic acid, a magnificent product 

 of anilin-red being thus obtained. This toluidin gave no reaction for anilin on beinc 

 tested with hypochlorite of lime. It may here be remarked that we have in the same 

 way repeatedly obtained anilin-red from toluidin prepared from samples of toluole ob- 

 tained from coal-tar naphtha by the process of fractional condensation. 



' 



Caprylene = C 16 H 16 "j At 117°-127° there was a large heap, amounting to 



- an <l - > about 800 c. c. It had two principal summits, one at 



Hydride of Capnjl = C 16 H 18 . J 123°-124°, the other at 126°-127°, and a subsidiary 

 elevation at 118°-120° ; but this last was probably caused by some irregularity in the 

 conditions under which the distillation was conducted, the work of two operators 

 having overlapped at this point. Moreover, as will be seen directly, analyses of the 

 subsidiary heap, after purification, indicated that it, as well as the fraction 123°-124°, 

 belongs to the C n H n series. 



All of the fractions from 117° to 127° constituting the great heap were treated with 

 diluted sulphuric acid in the usual way, after which the fractions belonging to each of 

 the three summits were separately and repeatedly distilled through Warren's hot 

 condenser ; the same thermometers, condenser, and retort being used in the distillation 

 of each of the summits. The relative importance of the fraction 123°-124° was main- 

 tained throughout, this fraction being far larger than any of the others. The fractions 

 125°-126° and 126°-127° also held their own during these redistillations ; but the posi- 

 tion of the lower, subsidiary summit changed materially, the greater portion of it 

 having finally collected at 121°-122°. It is probable that by continued redistillation 

 this might all have been collected at 123°-124°, or rather that these two heaps could 

 have been made to coalesce at some point between 122° and 124° ; but the quantity of 

 material being small, we have made no special eifort to effect this result. 



Previous to the treatment with acid, the heap 117°-127° had a remnant of the 

 offensive odor of the original crude hydro-carbon oil together with a trace of the odor 

 of acetone ; but on the addition of diluted sulphuric acid, an odor like that of mint was 



