172 J-TT.] 



HYDROGEN CYANIDE 



267 



According to Kerp (loc. cit, 611) free 

 hydrogen cyanide is also evolved. 



Or potassium chloracetate, by the 

 action of a nitrite, yields nitromethane 

 (Preibisch, Journ. pr. Ch. [2] 8, 316). 

 The latter, by the action of alkalis, 

 gives ' methazonic acid ' (Lecco, Ber. 

 9, 705 ; Dunstan and Goulding, Trans. 

 Ch. Soc. 77, 1262), which, on heating 

 with acids or alkalis or by oxidation 

 with potassium permanganate, yields 

 hydrogen cyanide (D. and G., loc. cit. 

 1264). 



A solution of copper acetate heated 

 with ammonia gives cuprous cyanide 

 (Vittenet, Bull. Soc. [3] 21, 261). 



Acetic acid and methyl alcohol [13] 

 give dimethylacetoacetic methyl ester, 

 which, on treatment with nitric acid, 

 yields a compound decomposable by al- 

 kali with the formation of hydrogen 

 cyanide among other products (W. H. 

 Perkin, junr., Proc. Ch. Soc. 17, 204). 



[K.] From propionic acid [Vol. II] 

 by heating dry sodium propionate 

 with a nitrite as above (Kerp, loc. cit. 

 611). 



[L.] From tarlaric acid [Vol. II] as 

 above, potassium sodium tartrate or 

 neutral sodium tartrate being fused with 

 nitrite. Free hydrogen cyanide is also 

 evolved (Warren, loc. cit. ; Kerp, loc. 

 cit. 611). 



Or indirectly from tartaric acid 

 through 'nitrotartaric acid' (Dessaignes, 

 Ann. 82, 362 ; Demole, Ber. 10, 1789 ; 

 Kekule, Aim. 221, 245). The latter [or 

 the ' dioxytartaric ' acid obtained from 

 it by the action of ethyl nitrite (Kekule", 

 loc. cit. 247), or .by decomposition by 

 aqueous sodium carbonate and acetate 

 (Thiele and Dralle, Ann. 302, 291, 

 note)] gives glyoxal on heating with 

 acid sodium sulphite in aqueous solution 

 (Hinsberg, Ber. 24, 3236). Subsequent 

 steps through glyoxime and cyanogen, 

 &c., as above under E. 



NOTE : Dioxytartaric acid can also be ob- 

 tained from tartaric acid through its oxidation 

 product, dihydroxymalei'c acid (see under 

 furfural [126 ; E]), and further oxidation of 

 the latter by bromine and water (Fenton, 

 Trans. Ch. Soc. 67, 48 ; 73, 71). 



[M.] From oxalic acid [Vol. II] by 

 heating the ammonium salt alone or 



with phosphorus pentoxide, &c. (Dumas, 

 Ann. 1O, 295 ; Bertagnini, Ann. 104, 

 176 ; Storch, Ber. 19, 2459). The 

 cyanogen thus formed can be con- 

 verted into hydrogen cyanide as above 

 under A. 



[N.] From lactic acid [Vol. II] 

 through ' nitrolactic acid ' (Henry, Ber. 

 3, 532), the latter undergoing spon- 

 taneous decomposition with evolution 

 of hydrogen cyanide (IdicL). 



[O.] Jfwn&acetie aldehyde [92] through 

 glyoxal by oxidation with nitric acid 

 (Liubavin, Ber. 8, 768 ; Journ. Russ. 

 Soc. 7, 249 ; 13, 496 ; Ber. 10, 1366 ; 

 De Forcrand, Bull. Soc. [2] 41, 242 ; 

 Spiegel, Ch. Zeit. 19, 1423), and then 

 through the oxime and cyanogen as 

 above under E. 



[P.] From catechol [69], which gives 

 dioxytartaric acid when acted upon by 

 nitrous gas in ethereal solution (Barth, 

 Monats. 1, 869). Subsequent steps as 

 above under L. 



[Q.] Protocatechuic acid [Vol. II] 

 gives dioxytartaric acid when treated as 

 above (Gruber, Ber. 12, 514). 



[B,.] Quinone [142] gives hydrogen 

 cyanide when oxidised by nitric acid in 

 excess (Kerp, Ber. 3O, 612). 



[S.] From fflycocoll [Vol. II], which 

 gives hydrogen cyanide when heated 

 with dilute sulphuric acid and manga- 

 nese dioxide (Watts's Diet., Morley and 

 Muir, II, 627). Or glycin ethyl ester, 

 by the action of nitrous acid, gives 

 ethyl diazoacetate (Curtius, Journ. pr. 

 Ch. [2] 38, 401). The latter, on treat- 

 ment with sodium ethylate, yields the 

 sodium derivative of ethyl isodiazoace- 

 tate. Free ethyl isodiazoacetate gives 

 hydrogen cyanide among the products 

 of its decomposition by heat (Hantzsch 

 and Lehmann, Ber. 34, 2506). 



[T.] From wetfiylamine [Vol. II] by 

 the action of heat on the vapour (Wurtz, 

 Ann. Chim. [3] 30, 454), or by com- 

 bustion of the moist vapour (Tollens, 

 Zeit. [2] 2, 516). Hydrogen cyanide 

 is also among the products of oxidation 

 of methylamine by monopersulphuric 

 acid (Bamberger and Seligman, Ber. 

 35, 4299). 



[U.] Trimetkylamine [Vol. II], when 

 the vapour is passed through a red-hot 



