1872.] Mr. C. Schorlemmer on the Normal Paraffins, 137 



III. " On the Normal Paraffins." By C. Schorlemmer, F.R.S. 

 Received December 20, 1871. 



(Abstract.) 



Some of the results of this research have already been published in two 

 previous communications*. It was there pointed out that the constitution 

 assigned to the normal paraffins (i. e. that they contain the carbon atoms 

 linked together in a single chain) was ascertained partly by preparing them 

 by synthesis from other normal compounds, and partly by studying the 

 oxidation products of the alcohols obtained from them. The best method 

 to prepare these alcohols is to pass a current of dry chlorine into the 

 vapour of the boiling hydrocarbon ; a mixture of a primary and a secondary 

 chloride is obtainedf, and these, by heating the mixture with glacial acetic 

 acid and potassium acetate to 200°, are completely decomposed, the primary 

 chloride yielding the corresponding acetate, whilst the secondary compound 

 partly splits up into an olefine and hydrochloric acid, and partly is con- 

 verted into the acetate of the secondary radical. By treating the acetates 

 with an alcoholic solution of caustic potash, the alcohols are formed, which 

 can be only approximately separated by fractional distillation, as the dif- 

 ference between their boiling-points is only about 10°. 



Pentane or normal amyl hydride, C. H 12 , boiling at 37°-39°, is found in 

 considerable quantity in Pennsylvania petroleum. The secondaiy pentyl 



alcohol or methyl-propyl carbinol, ^ g 3 1 CH OH (boiling-point 120°- 

 122°), gives on oxidation methyl propyl ketone, £ S 3 1 CO, which on 



further oxidation splits up into acetic acid and propionic acid. The pri- 

 mary pentyl alcohol is identical with the normal amyl alcohol, which 

 Lieben and Rossi obtained from normal butyric acid, and yields on oxida- 

 tion normal valerianic acid, boiling at 184°-187°. 



Hexane or normal hexyl hydride, C 6 H 14 .— (1) Hexane from petroleum, 

 boiling at 69°-70°, yields the following derivatives :— (a) Methyl-butyl 

 CHI 



carbinol, q H 3 j CH. OH (boiling-point 140°-142°),the oxidation products 

 of which consist of methyl-butyl ketone, q | CO, and acetic acid and 



normal butyric acid, (b) Primary hexyl alcohol, boiling at 150°-155°, 

 from which caproic acid, boiling at 201°-204°, was obtained. 



(2) Hexane from mannite was obtained by acting with hydrochloric 

 acid and zinc upon the secondary hexyl iodide prepared from mannite. 

 It boils at 71°-5, and its specific gravity at 17° is 0'6630. The deri- 



* Proc. Eoy. Soc. vol. xix. pp. 20 & 487. 



t The same mixture is obtained by the action of chlorine in the cold, or in presence 

 of iodine; but at the same time a large quantity of higher chlorinated substitution 

 products is formed, which is not the case by acting with chlorine on the vapour. 



M 2 



