NEF. BIVALENT CARBON. 171 



in an ethereal solution of the substance after a few moments a rise 

 in temperature, " which often is so great that the ether begins to 

 boil." * The carbyloxime formed in the nascent state polymerizes to 

 a great extent, just as has often been noticed in analogous cases with 

 isocyanides. For this reason it seems to me highly probable that 

 Scholvien's isocyanuric acid f consists simply of polymerized carbyl- 

 oxime, and probably possesses the constitution 



OH 



C-N-C 



I I 



HON-C-NOH. 



All the properties of the substance can easily be explained by this 

 formula, and a further study of it will be taken up very shortly ; 

 especially also because Scholvien states that on treating the silver 

 salt CgHNgOsAga with ethyliodide, " a filtrate was obtained smelling 

 strongly of carbylamine." $ It is very likely that in this reaction no 

 ethyl isocyanide, but ethylcarbyloxime, C2H5ON : C, is formed, — a 

 substance which, as will be shown farther on, cannot be distinguished 

 from ethyl isocyanide in respect to odor. 



Ehrenberg has already had an ethereal solution of formylchlorid- 

 oxime (containing also mercuric chloride and hydrogen chloride) in his 

 hands. He obtained it by passing dry hydrogen chloride over mercu- 

 ric fulminate suspended in absolute ether; and he assumes that free 

 fulminic acid may possibly be present in the solution. He describes 

 the ethereal solution § as a "strong-smelling liquid, bringing teai's to 

 the eyes, and affecting the mucous membrane, and causing an intensely 

 bitter taste in the mouth. The smell reminds one^of prussic acid, but 

 this could not be detected in the solution. On attempting to distil 

 off the ether, the mass all at once decomposed with violence and with 

 a hissing noise." 



Ehrenbeig was, in consequence, unable to isolate the product, and 

 studied only the action of aqueous ammonia upon the ethereal solution 

 of the substance. The nature of the compounds which he obtained in 

 this way is cleared up by the experiments mentioned below. 



Fulminic acid salts can therefore be obtained synthetically in four 

 different ways, as follows. 



1. From sodic nitromethane : 



H2C : N-ONa + hgCl = C : NOhg + NaCl + n„0. 



II 

 O 



* Journ. f. prakt. Chem., [2.], XXXII. 463. | Ibid., XXXII. 473. 



t Ibid., XXXII. 464. § Ibid., XXX. 44 



