1869.] Mr. C. Schorlemmcr on Octyl Compounds. 



25 



XV. " Researches on the Hydrocarbons of the series C n H 2n+2 . 

 — No. V. On Octyl compounds." By C. Schorlemmer. 

 Communicated by Prof. Stokes,, Sec. R.S. Received June 

 17, 1869. 



After I had found that the octylalcohol obtained by distilling castor 

 oil with caustic soda, is methyl-hexyl carbinol, or a secondary alcohol*, 

 it appeared to me of great interest to study the chemical structure of those 

 alcohols which can be obtained from the different hydrocarbons of the 

 formula C s H 13 , the more so as Cahours and Pelouze assert that the deri- 

 vatives of the octane contained in petroleum are identical with those derived 

 from the castor-oil alcoholf, a statement which was afterwards confirmed 

 by Chapman J. 



The hydrocarbons which I used for my experiments were hydride of 

 octyl, or octane from petroleum, and the hydrocarbon of the same com- 

 position, which I obtained by acting upon iso-octyl iodide with zinc and 

 hydrochloric acid. The two hydrocarbons, as well as their derivatives, 

 resemble each other in their physical properties so much, that one would 

 be inclined to consider them as identical ; their chemical properties, how- 

 ever, prove that they are only isomeric. 



(1) Derivatives of Octane from Petroleum. 



The boiling-point of this hydrocarbon is given differently by different 

 observers between 116° and 120°; according to my latest researches, it 

 appears to boil a few degrees higher. After fractionating it for a very 

 long time, the greater portion was found to boil between 120° and 125°; 

 it was now heated with nitric acid and again fractionated over sodium. A 

 considerable portion distilled now at 119°-122°, but by far the largest 

 quantity at 122°-125°. From this latter portion I prepared the octyl- 

 chloride, a colourless liquid, which smells like oranges, and boils at 1/3°- 

 1/6°. This chloride was heated up to 200° for several hours with con- 

 centrated acetic acid and potassium acetate. It was thus completely de- 

 composed ; the chief product of the reaction consisted of octylene, besides 

 that a much smaller quantity of octyl-acetate had been formed. This 

 ether is a colourless liquid, boiling at 200°-205°, and having a pleasant 

 pear-like odour. It was converted into octyl-alcohol by heating it with 

 an alcoholic solution of caustic potash. This alcohol, after being purified 

 by washing it several times with water, and drying over fused potassium 

 carbonate, was obtained as a colourless oily liquid, boiling at 180°-182°, 

 and possessing exactly the odour of methyl-hexyl carbinol. 



The alcohol was oxidized by mixing it slowly with a cold solution of 

 2 parts of potassium dichromate and 3 parts of sulphuric acid in 1 0 parts 

 of water, care being taken to avoid as much as possible any elevation of 



* Proc. Koy. Soc. vol. xvi. p. 376. t Ann. Chem. Phys. 4 ser. voL i. p. 53. 



\ Journ. Chem. Soc. N. S. vol. hi. p. 296. 



