318 . REPORT— 1873. 



Even had this yellow resin been pure terephthalie acid it would not have 

 amounted to more than 0"3 per cent, of the hydrocarbon used. 



The nitric-acid solution was evaporated to drj'ness, the residue ueutralized 

 by ammonia, and barium nitrate added in the cold ; a copious precipitate 

 of oxalate was obtained, from which pure oxalic acid and calcium and silver 

 oxalates were procured and analyzed. The filtrate on boiling gave a trifling 

 sandy precipitate, which was nothing but oxalate ; no trace of Kachler'a 

 camphoronic acid could be detected. 



The filtrate was precipitated by lead acetate, the copious pi-ecipitate well 

 washed and decomposed by sulphuretted hydrogen, and the evaporated solu^ 

 tion thus obtained extracted with ether ; after evaporation a yellow sour 

 syrup was obtained, which, on standing for several months over sulphuric 

 acid, refused to deposit crystals, but gradually thickened, and finally became 

 a semisolid mass much resembling soft toffy : no crystals could be obtained by 

 pressure in blotting-paper. On combustion this gave numbers indicating 

 approximately the formula C^^H^gOj^, but differing considerably from those 

 required for either camphresinic or camphoronic acids. Converted into cal- 

 cium salt a gummy salt was obtained, which, after drying at 160°, contained 

 18-1 to 18-5 of calcium. On dissolving this in water and precipitating by 

 alcohol a calcium salt was thrown down resembling the original one in aU 

 respects, but containing 20-8 per cent, of calcium after drying at 160°. From 

 this it appears that the syrupy toffy-like acid was a mixture. The isolation 

 of the constituents of this mixture has not j'ct been finished. 



On treating the 163°-1G4° nutmcg-terpene in the same way, precisely 

 similar results were obtained, with this difference, that the brown resinous 

 product formed after the action had gone on for a short time was converted, 

 by longer treatment, into a yellow resin, which, after purification by solution 

 in ammonia, treatment with animal charcoal, and precipitation of the nearly 

 decolorized solution by nitric acid, furnished a mixture of toluic and tereph- 

 thalie acids. In one carefully conducted quantitative experiment, 105-8 

 grammes of pure hydrocarbon gave 14-0 of a mixture which, on analysis, ap- 

 peared to contain the acids in the proportions denoted by 40^11^0^ -l-C^H^O^ ; 

 ■i. e. the mixture was 13-2 per cent, of the hydrocarbon. In other experiments, 

 with the mixture of hydrocarbons boiling below 180° contained in the nut- 

 meg-oil, 17 to 18 per cent, of a mixture of C^H^O, and C^HyOj in nearly 

 equal proportions was obtained. 



It was found difficult to separate completely the toluic and terephthalie 

 acids by boiling water or alcohol, in which the latter is much the least soluble ; 

 but approximately pure specimens of each acid were isolated and recognized 

 by combustion, properties, and preparation of barium salts. 



The nitric-acid solution was found to contain oxalic acid, recognized by its 

 properties and the analysis of its calcium salt ; this was separated, and the 

 filtrate treated in the manner above described ; finally a syrupy toffy-hke 

 acid was obtained, much resembling that from hesperidene. This gave 

 numbers agreeing with the formula Cj^Hj^O^ ; on conversion into calcium 

 salt and precipitation by alcohol, a substance Avas obtained which, after drying 

 at 160°, contained 20'4 per cent, of calcium The examination of these pro- 

 ducts is not yet concluded, 



5. Action of Hydriodic Add on Hesperidene- — Gaseous hydriodic acid was 

 passed into hesperidene till saturated ; the substance remained liquid : after 

 agitation with dilute caustic soda the liquid boiled at near 220°, with partial 

 decomposition, and gave numbers indicating the compound Cj^HjuHI mixed 

 with some unaltered hydrocarbon. 



