266 



CYANOGEN COMPOUNDS 



[172 C-J. 



nitro-derivatives of which give hy- 

 drogen cyanide among the products 

 of the action of alkali (Hiibner and 

 Post, Ber. 5, 408). From benzene via 

 nitrobenzene, phenylhydroxylamine, and 

 nitrosobenzene. The latter gives hy- 

 drogen cyanide among the products of 

 the action of alkali (Bamberger, Ber. 

 33, 1939). 



Or from benzene through trichlor- 

 phenomalic acid (see under carbon di- 

 sulphide [160; N]) and chloroform, 

 'and then as under E below. 



Or from toluene [64 ; A, &c.] through 

 o-nitrofcolnene and o-toluidine, the latter 

 giving hydrogen cyanide by the action 

 of sodium hypochlorite (Meigen and 

 Normann, Ber. 33, 2714). 



[D.] From phenol [60], hydrogen 

 cyanide being among the products of 

 the action of alkali on the nitro-deriva- 

 tives (Hiibner and Post, as above : see 

 also Wedekind and Haussermann, Ber. 

 35, 1133). 



From phenol and ethyl alcohol 

 [14] through coumarone (see under 

 phlorol [64; Cl) and nitrocoumarone 

 (see under salicylic aldehyde [117; A]). 

 The latter gives hydrogen cyanide 

 among the products of its decomposition 

 by sodium ethylate (Stoermer and Kah- 

 lert, Ber. 35, 1640). 



[E.] From ethyl alcohol [14] through 

 chloroform (see under methane [l; D]). 

 Hydrogen cyanide is formed by passing 

 ammonia and chloroform vapour through 

 a hot tube, or by heating chloroform and 

 alcoholic ammonia to 180-190 (Heintz, 

 Ann. 100, 369 ; Cloe'z, Jahresber. 1858, 

 345). Also by the action of caustic 

 potash on chloroform in presence of 

 aqueous ammonia (Hofmann, Ann. 144, 

 116). 



Alcohol also gives hydrogen cyanide 

 among the products of its oxidation by 

 nitric acid, possibly through the forma- 

 tion of an oximido-compound (Gill and 

 Meusel, Zeit. [2] 5, 66; Hantzsch, 

 Ann. 222, 65). 



Or from alcohol through glyoxal by 

 oxidation with nitric acid (Debus, Ann. 

 102, 20; 107, 199; 110, 316; 118, 

 253). The oxime (glyoxime) gives 

 cyanogen on heating with acetic anhy- 

 dride (Lach, Ber. 17, 1573), and- this 



can be converted into hydrogen cyanide 

 as above under A. 



NOTE : The following compounds thus be- 

 come, through chloroform, generators of hydro- 

 gen cyanide (see under carbon disulphide [160 ; 

 D ; E ; F ; K ; L ; M]) : 



Acetone [106] ; aldehyde [92] ; acetic, gallic, or 

 salicylic acid [Vol. II] ; phenol [60]. The last 

 three through trichlor-aa-glyceric acid and 

 chloroform. 



[F.] From formic aldehyde [9l], the 

 polymeric oxime of which gives hydro- 

 gen cyanide on sudden heating (Scholl, 

 Ber. 24, 577). Or formoxime yields 

 hydrogen cyanide on dehydration by 

 phosphorus pentoxide (Dunstan and 

 Bossi, Trans. Ch. Soc. 73, 360). 



[G.] From isolutyric aldehyde [94] 

 through the a-brom-paraldehyde by 

 bromination (Franke, Monats. 21, 205). 

 The latter gives an oxime which, by 

 the action of acetic anhydride, yields a 

 resinous nitrile which is decomposed by 

 sodium carbonate into hydrogen cyanide 

 and acetone (Ibid. 210 : see also under 

 acetone [106 ; DD]). 



[H.] Uextrose, Itevuluse [154; 155], 

 and many sugars give hydrogen cyanide 

 among the products of their oxidation 

 by nitric acid (Hautzsch, Ann. 222, 

 65 : for production from saccharose see 

 Burls, Evans, andDesch, Ch. News. 68, 



75)- 



[I.] From formic acid [Vol. II] by 



heating the dry ammonium salt (Pelouze 

 and Dobereiner, Ann. 2, 90), or by dis- 

 tilling this salt or formamide with phos- 

 phorus pentoxide (Lorin, Ann. 132, 

 255 ; Hofmann, Journ. pr. Ch. 91, 61 ; 

 Journ. Ch. Soc. 16, 74). By distilling 

 ammonium formate (or formamide) into 

 heated potash potassium cyanide is 

 formed (Glock, Germ. Pat. 108152 of 

 1899; Ch. Centr. 1900, 1, 1115). 



Or phospham, when heated with for- 

 mic acid, gives at 150-200 hydrogen 

 cyanide (Vidal, Germ. Pat. 101391 of 

 1898; Ch. Centr. 1899, 1, 960; also 

 Eng. Pat. 4227 of 1898; Journ. Soc. 

 Ch. Ind. 18, 398). 



[J.] From acetic acid [Vol. II], dry 

 sodium acetate giving the cyanide (15 

 p.c.) on heating with a nitrite (Warren, 

 Ch. News, 72, 40 ; Kerp, Ber. 3O, 610 : 

 see also Roussin, Comp. Rend. 47, 875). 



