♦ 



— 109 — 



for several days. Combustion showed the fraction to consist of a hydro- 

 carbon C15H24, only slightly contaminated by oxygenous constituents. 



0,4062 g. substance: 1,2836 g. C0 2 , 0,4194 g. H 2 0. 

 Found Calc. for 



C 86,18% 88,23% 



H 11,48% 11,77% 



For purposes of further purification the hydrocarbon was treated with 

 metallic sodium and resolved into separate fractions. By this method we 

 finally isolated an oil possessing the following constants: b. p. 95,5° (4 mm.), 

 258 to 261° (756 mm.), di 5 o 0,9206, « D — 81°56', n D20O 1,50049. 



The fraction was treated for obtaining nitrosate and nitrosochloride, but 

 without positive result. The strong lsevorotation of all these fractions ap- 

 peared to indicate that they might consist of gurjun balsam oil. Now it is 

 well-known that some time ago Deussen and Philipp 1 ), by oxidising gurjun 

 balsam oil with permanganate in acetone solution, obtained a reaction- 

 product which, it appears, may serve as a criterion for the detection of the 

 addition of gurjun balsam oil to other oils, a view which is borne out by 

 our present experience. The oxidation-product, b. p. 175 to 178° (12 mm.), 

 is according to Deussen a ketone, and is sharply characterised by a semi- 

 carbazone melting at 234° and rather sparingly soluble in alcohol. The 

 fractions of our sample with the strongest rotatory power had already 

 been used up for other reactions, and for the purpose of oxidation only 

 the two following fractions, amounting in all to about 14 g., were left: 



(1) B. p. 255 to 260°, « D — 50° 32', 



(2) B. p. 260 to 262°, a D — 48° 53'. 



The oil was dissolved in about 200 g. acetone, diluted with 35 g. water, 

 and to the clear solution were gradually added 15 g. solid powdered per- 

 manganate. The unattacked oil, which boiled at 104 to 105° (5 mm.) was 

 removed by fractionation and the distillation-residue treated with semi- 

 carbazide. The reaction-product was left standing overnight, when, after 

 the addition of water, it was deposited as an oily precipitate, solidifying 

 in part after prolonged cooling in ice under stirring with alcohol. The 

 semicarbazone, repeatedly recrystallised from hot alcohol, had m. p. 234°, 

 and, with a semicarbazone of the same m. p. and constants, prepared from 

 gurjun balsam oil for purposes of comparison, suffered no depression 

 mi m. p. These two bodies were therefore identical. 



From the result of the above examination it is to be concluded that 

 the strongly lsevorotatory oil which had been added to the stearoptene 

 of the rose oil consisted principally of gurjun balsam oil, which had been 

 improperly added to the rose oil for purposes of adulteration. Possibly 



!) Liebigs Annalen 369 (1909), 56; 374 (1910), 105. Report April 1910, 146. 



