M. Lossen on Naphthaline. 513 



Otto and Monies describe the formation of a mercury com- 

 pound of naphthaline. When to monobrominated naphthaline 

 dissolved in benzole sodium amalgam is added, a violent reac- 

 tion ensues; the bromine is taken away, but, instead of the two 

 rests, G 10 H 7 , uniting together to form a dinaphthyle analogous to 

 dibenzyle and ditolyle, mercury takes its place and a mercury 

 naphthyle is formed, in accordance with the following equation : 



2€ 10 H 7 Br + Na 2 Hg" = ||° w } Hg" + 2 NaBr. 



Monobrominated Mercury 



naphthaline. naphthyle. 



Mercury-naphthyle is easily prepared in large quantities. It 

 forms colourless needles which are readily soluble in hot benzole, 

 but very little so in alcohol, and not at all in water. They melt 

 at 248°. Iodine unites directly with it, forming a compound 

 crystallizing in beautiful satin scales. 



Lossen* has made a very exhaustive examination of the pro- 

 ducts of oxidation of naphthaline. By the action of a boiling solu- 

 tion of permanganate of potassium it yields phthalic acid, € 8 H 6 G 4 . 

 Laurent had stated that by the action of a mixture of sulphuric 

 acid and bichromate of potassium, a new acid, naphthesic acid, was 

 formed, to which he assigned the formula G 10 H 6 9 4 . Lossen has 

 ascertained that this substance is really the anhydride of phthalic 

 acid, G 8 H 6 O 3 , and that this substance and phthalic acid are 

 the main products of the oxidation of naphthaline by the above 

 agents. 



A mixture of manganic oxide and sulphuric acid yields prin- 

 cipally phthalic acid ; but there is formed at the same time some 

 quantity of the body dinaphthyle, G 20 H 14 , which is produced from 

 naphthaline by direct oxidation, 



* H J +e - G 10 H 7 / + H_| e ' 



This body melts at 154° C, is quite volatile, and boils at a tem- 

 perature higher than that of boiling mercury. From solution 

 in ether-alcohol it crystallizes in regular octahedra. It forms 

 with bromine dibromo dinaphthyle, € 20 H 12 Br 2 , a compound of 

 great stability, and when bromine is in great excess hexabromo- 

 dinaphthyle, G 20 H 8 Br 6 . By the action of strong nitric acid on 

 naphthyle, € 20 H 10 (NO 2 ) 4 , tetranitrodinaphthyle is formed. 



* Liebig's Annalen, October 1867. 



