118 
MR, C. SCHORLEMMER ON THE NORMAL PARAFFINS. 
(2) On evaporating the mother-liquor a second crop was obtained, 0166 of which 
gave 0-0800 Ag. 
Found. 
, v N 
Calculated for C 6 H u 0 2 Ag. I. II. 
48-43 per cent. Ag 48 - 59 4819 
The calcium salt crystallizes from a hot concentrated solution in shining scales ; by 
spontaneous evaporation it is obtained in ramified needles. 
The most characteristic salt of this acid is the barium salt, which could not be obtained 
in the crystalline state, but which on evaporating an aqueous or alcoholic solution at a 
higher or at the common temperature, is always obtained as an amorphous, gum-like 
mass. 
As the caproic acids of different origin have been so far very little studied, I have not 
investigated the salts of my acid more fully. 
The oxidation products of the secondary hexyl alcohol or methyl-butyl carbinol, viz. 
acetic acid and normal butyric acid , are quite sufficient to prove that the hexane in petro- 
leum is a normal paraffin, the constitution of which is expressed by the formula 
ch 3 — ch 2 — ch 2 — ch 2 — ch 2 — ch 3 . 
Hexan e from Mann ite. 
Erlenmeyer and Wanklyn obtained this hydrocarbon by heating the secondary hexyl 
iodide obtained from mannite with zinc and water. I found it more convenient to act 
on the iodide with zinc and hydrochloric acid in the cold. To prepare it, a flask is filled 
with finely granulated zinc, the iodide is added, and then so much dilute hydrochloric 
acid that the zinc is not completely covered. The vessel must be immersed in cold 
water, or else a very violent reaction sets in. After a few hours the heavy iodide has 
disappeared and a light layer swims on the top, which, when subjected to distillation, 
was found to consist of a liquid boiling at about 70°, besides a smaller quantity of a body 
boiling at above 190°. 
The liquid boiling at 70° had the odour of hexene, and the reaction with bromine 
showed that this body was present. In order to remove it, bromine was added drop by 
drop to the well-cooled liquid as long as its colour disappeared, and then hexane and 
hexene dibromide separated by fractional distillation. 
The hexane from mannite, after being purified by treatment with nitric and sulphuric 
acids and rectification over sodium, is a mobile liquid, having the faint but characteristic 
odour of the paraffins. It boils constantly at 71°*5, and has at 17° the specific gravity 
0-6630. 
By acting with chlorine on its vapour a product is obtained, the greater portion of 
which boils at 126° to 12 8°*5, and a smaller at 128°*5 to 130°. Besides these, higher 
