MR. C. SCHORLEMMER ON THE NORMAL PARAFFINS. 
119 
chlorinated products had been formed, but only in a small quantity. From the liquid 
boiling between 126° and 130°, the alcohols were prepared and separated by fractional 
distillation into two portions ; one, being about § of the whole, boiled constantly at 
140° to 141° ; between 141° and 150° only a small quantity distilled, the remainder coming 
over between 150° and 153°. The products of oxidation were the same as those from the 
petroleum hexane, viz. methyl-butyl ketone and caproic acid. 
The methyl-butyl ketone boiled constantly at 127°, and appears to be identical with 
that which Erlenmeyer and Wanklyn obtained from the secondary hexyl alcohol; on 
further oxidation it yields acetic acid and normal butyric acid, the presence of the latter 
being proved by the characteristic properties of the calcium salt. 
The analyses of the silver salts, which were obtained as described above, gave the fol- 
lowing results : — 
Calculated for silver butyrate . . . . 55*38 per cent. 
1st fraction, 0*375 gave 0*1975 Ag=55*35 per cent. 
2nd „ 0*1241 „ 0*0685 Ag=55*19 per cent. 
3rd „ 0*1365 „ 0*079 Ag=57*88 per cent. 
4th „ 0*183 „ 0*118 Ag=64*48 per cent. 
Calculated for silver acetate 
64*67 per cent. 
The caproic acid, of which I obtained only a small quantity, had the same odour as 
that from petroleum, and the same boiling-point, viz. 201° to 204°. 
0*1655 of silver caproate, which formed small needles, gave 0*0803 Ag=48*5 per cent., 
the calculated quantity being 48*43 per cent. 
The calcium salt had the same properties as that from petroleum ; the barium salt, 
however, was not amorphous, but crystallized most readily in plates or broad needles. 
On decomposing the monochlorides with potassium acetate about equal quantities of 
the acetic ethers and hexene were formed, and by oxidizing the mixture of the two 
alcohols the quantity of acetone was double that of the caproic acid. Now, as the 
hexene was no doubt derived from the secondary chloride, it appears that by the action 
of chlorine upon the hydrocarbon ^ is converted into the primary chloride, and § into 
the secondary one. 
The hexane of mannite and some of the derivatives boil a few degrees higher than 
the corresponding compounds from petroleum, and also the barium salts of the two 
caproic acids exhibit a decided difference. The hexane from petroleum is certainly not 
a pure compound ; but whether this is the cause of the difference between the two hydro- 
carbons, or whether we have here a case of fine isomerism, for which an explanation has 
to be found, it is at present impossible to decide ; the formation of acetic and normal 
butyric acids, however, proves that the hexane from mannite is also a normal hydro- 
carbon. 
The products formed by acting with zinc and hydrochloric acid on hexyl iodide consist 
