314 



REPORT — 1873. 



the " myristicol " of Gladstone. After several fractionations, however, it* 

 became evident that this substance alters by the action of heat upon it, be- 

 coming changed, first, into liquids of the same composition but higher boiling- 

 point, and finally into an isomeric resin, not volatile at 300°. The purest 

 unaltered "myristicol" obtained boiled between 212° and 218°; both this 

 and the higher isomerides boiling at 2Go° to 285° and the resin not volatile 

 at 300° gave on analysis numbers which lay between those required for the 

 formula) C,„HjjO and Cj^Hj^O, more nearly approximating to the latter; from 

 this it is concluded that the " myristicol " of Gladstone is essentially a peculiar 

 kind of camphor, C^gtl^fi, which on heating becomes transformed into a mix- 

 ture of polymerides bcariug to it the same relation that the colophenes and 

 cedrenes bear to the tcrpenes ; this conclusion is strongly supported by the 

 physical properties of these polj^meridcs as examined by Dr. Gladstone. 



This polymerization by heat of C,(,II,j,0 bodies probably affords an ex- 

 planation of the anomalous results obtained in the distillation of certain 

 naturally oxidized essential oils, such as lign aloes, from which no substance 

 of constant boiling-point can be obtained, the distillates obtained in one 

 operation continually altering in another. 



The action of phosphorus pentachloride on myristicol has been examined, 

 and ajspears to be in accordance with the equation 



C,„H„0 + PCL = P0Cl3+HCl+C,„H,Cl, . 



a reaction 



that it may be written C^, 



0. 



kind of alcohol or phenol, i. e. 

 The resulting product 0^^11^.01 is diiH- 



iudicatiug that myristicol is a 

 K. ] 



cult to obtain even approximately pure, as the action of heat causes it to 

 split up into HCl and Cj^^Hj^. The hydrocarbon thus formed has not j-et 

 been thoroughly examined ; a considerable quantity of it becomes pol3'merized 

 at the moment of its formation into a yellow-brown viscid resin, not volatile 

 at the extreme limit of the mercurial thermometer, and having apparently 

 the composition (C^JI^.)^. It is proposed to obtain myristicol in larger 

 quantities, and to examine more fully this action, and also the action of 

 phosphoric anhydride &c. on it. Camphor gives rise, by the action of 

 dehydrating agents, to cymene, Cj^H^^ ; it wiU be of interest to determine 

 whether such a reaction takes place with myristicol, and if so whether the 

 same cymene is formed. 



The hydrocarbons contained in the nutmeg-oil distillates boiling below 180° 

 were heated for some time in contact Avith sodium, and submitted to careful 

 fractional distHlatiou over that metal for several weeks ; fiually the whole 

 was almost entirely split up into two portions — one constituting about three 

 fourths of the whole and boiling at 163° to 166°, and the other, about one 

 Tsixth as large in quantity, boiling at 173° to 177°. Intermediate fx-actions 

 were at first obtained ; but by successive distillations these split up almost 

 entirely into the higher and lower fractions. A small quantity was also 

 obtained boiling above 177° ; but this contained a miniite quantity of an ox- 

 idized constituent not destroyed by the sodium, distillates at 179° to 181° 

 and 181° to 185° giving numbers on analysis adding up to 98-6 and 98-8 

 respectively : — 



■ The following percentages were obtained with the fractions that were free 

 from oxidized substances : — ■ 



