go Journal of Agricultural Research voi. x, no. i 



(2) by heating urea. Wohler's synthesis of cyanuric acid has been 



recently modified by Von Walther (12), whose method has been outlined 



above. Besides these classic methods of preparation, the literature is 



replete with descriptions of the synthesis of this compound, and mention 



is frequently made of the occurrence of cyanuric acid as a by-product in 



\ \ 



reactions involving compounds having the C:NH or — C.NHj groups. 



NH 



Cvanuric acid is also formed from its isomer cyamelid, C — O — C:NH 



II 



o— c— o 



NH 

 on prolonged digestion with cold dilute alkali (5). This reaction should 

 be emphasized, since it suggests that cyamelid, if present in the soil, 

 would be converted into cyanuric acid by the method here followed. 

 The isolation of cyanuric acid might even be taken as indicative of the 

 presence of cyamelid, since an alkaline extraction would convert cyamelid 

 into cyanuric acid. Cyamelid may therefore be the precursor of the 

 cyanuric acid isolated in our experiments. Cyamelid is insoluble in all 

 the ordinary organic solvents, and the solvents in which it is soluble 

 (alkali and concentrated acid) convert it into cyanuric acid. It seems 

 impossible therefore to determine whether or not cyamelid is a soil 

 constituent and the mother substance of the cyanuric acid isolated. 



Although so frequently referred to in the literature, cyanuric acid has 

 apparently never been previously isolated from a natural source. The 

 above methods of obtaining cyanuric acid suggest the possibility of its 

 formation by the decomposition of nucleoprotein or purin bases, 

 some of which have been previously isolated from soil (9). It is also 

 conceivable that the source of cyanuric acid is urea. 



LITERATURE CITED 

 (i) Beilstein, F. 



1893. HANDBUCH der organischen chemie. Aufl. 3, Bd. I. Hamburg, 

 Leipzig. 



(2) BERZELIUS, Jacob. 



1830-31. JAHRES-BERICKT UBER DIE FORTSCHRITTE DER PHYSISCHEN WISSEN- 

 SCHAFTEN. AUS DEM SCHWEDISCHEN UBERSETZT VON F. WOHLER. 



Jahrg. 9, 1830; Jahrg. lo, 183 1. 



Reference to Serrulas (Jahrg. 9, p. 86), and to Wohler and Scheele 

 (Jahrg. 10, p. 82). 



(3) Cohen, J. B. 



1909. ORGANIC CHEMISTRY FOR ADVANCED STUDENTS. V.I. London. 



• (4j Hantzsch, a. 



1902. uEbEr structurisomerE quecksilbER-cyanurate. In Eer. Deut. 

 Chem. Gesell., Jahrg. 35, No. 14, p. 2717-2723. 



(5) 



1905. UEBER DAS CYAMEUD. In Bcr. Deut. Chem, Gesell., Jahrg. 38, No. 4, 



p. 1013-1021. . 



