26 



HYDROCARBONS 



[l T-HH. 



the acid potassium salt, Petersen, Ch. 

 Centr. 1897, 2, 519; 1900, 2, 171), 

 and then as above under D. 



Or succinic acid gives a dibromo-acid 

 on bromination (Kekule, Ann. 117, 123 ; 

 Ann. Suppl. 1, 352 ; Bourgoin, Bull. 

 Soc. [2] 19, 148 ; Gorodetzky and 

 Hell, Ber. 21, 1731); and this by treat- 

 ment with alcoholic potash gives acetyl- 

 enedicarboxylic acid (Bandrowsky, Ber. 

 10, 838 ; Baeyer, Ber. 18, 677 ; 2269), 

 the sodium salt of which gives, on the 

 addition of silver nitrate, silver acetylide 

 (Lessen, Ann. 272, 140). Acetylene 

 liberated from the latter gives methane 

 as above under A. 



[U.] Fumaric acid [Vol. II] combines 

 with bromine to form dibromsuccinic 

 acid (Kekule", Ann. Suppl. 1, 131 ; 

 Baeyer, loc. cit. ; Kirchhoff, Ann. 280, 

 209; Michael, Journ. pr. Ch. [2] 52, 

 395). Subsequent steps as above 

 under T. 



Or fumaric (or male'ic) acid gives 

 acetylene on electrolysis of a strong 

 solution of the sodium salt (Kekule", 

 Ann. 131, 85). 



Or male'ic acid (anhydride) on com- 

 bination with bromine gives isodibrom- 

 succinic acid (Kirchhoff, Ann. 280, 207), 

 and this on heating with strong hydro- 

 bromic acid gives dibromsuccinic acid 

 (Michael, Journ. pr. Ch. [2] 62, 324). 

 Subsequent steps as above under T. 

 Isodibromsuccinic acid also on treatment 

 with alcoholic potash gives acetylene- 

 dicarboxylic acid (Bandrowsky, Ber. 10, 

 838), which gives acetylene and methane 

 as above under T. 



[V.] Azelctic acid [Vol. II] gives 

 a small quantity of ethylene among 

 the products of its distillation with 

 soda-lime (Miller and Tschitschkin, Ch. 

 Centr. 1899, 2, 182). Ethylene gives 

 methane as above under D. 



[W.] Salicylic acid [Vol. II] by the 

 action of potassium chlorate and hydro- 

 chloric acid gives trichlor-aa-glyceric 

 acid, from which chloroform can be 

 obtained (see under M above). 



[X.] From gallic acid [Vol. II] 

 through trichlor-aa-glyceric acid by the 

 action of potassium chlorate and hydro- 

 chloric acid and chloroform, &c., as 

 before (see under M above). 



[Y.] MetJiylamine [Vol. II] gives 

 methane among the products of its re- 

 duction by strong aqueous hydriodic 

 acid at a high temperature (Berthelot, 

 as above under I). 



[Z.] TrimetJiylamine [Vol. II] on 

 heating the hydrochloride to 326 de- 

 composes with the formation of methyl 

 chloride (Vincent, Journ. Pharm. [4] 

 30, 132; Jahresber. 1878, 1 1 35). Me- 

 thyl chloride gives methane among the 

 products of pyrogenic decomposition 

 (Perrot, Ann. 101, 375), or a solution 

 of the chloride might be reduced as 

 above under C. 



[AA.] Benzene (see under cymene 

 [6 ; I, &c.]) by the action of sulphuric 

 acid and potassium chlorate gives tri- 

 chlorphenomalic acid, CC1 3 . CO . CH : 

 CH.COOH (Carius, Ann. 142, 129; 

 Kekule and Strecker, Ann. 223, 170; 

 Anschiitz, Ann. 254, 152), and this 

 decomposes into chloroform (and malei'c 

 acid) on heating with barium hydroxide 

 solution. For reduction of chloroform 

 to methane see above under D. 



[BB.] From malic acid [Vol. II], 

 which gives bromoform by the action 

 of bromine and alkali (Cahours, Ann. 64, 

 351). Subsequent steps as above under D. 



[CO.] From citric acid [Vol. II], 

 which gives bromoform as above. 



[DD.] Ethylamine [Vol. II] gives 

 methane among the products of pyro- 

 genic decomposition (Miiller, Bull. Soc. 

 [2] 45, 43 8 )- 



[EE.] Glucose [154] gives an oxime 

 which on reduction yields the base 

 glucamine. The latter gives iodoform 

 with iodine (Maquenne and .Roux, 

 Comp. Rend. 132, 980). From iodoform 

 to methane as above under D. 



[PP.] From isovaleric acid [Vol. II], 

 methane being among the products of 

 the dry distillation of the calcium salt 

 (Dilthey, Ber. 34, 2115). 



[GQ.] Isoamyl alcohol [22] gives 

 methane among the products or pyro- 

 genic decomposition by the contact 

 action of certain heated metals on the 

 vapour (Ipatieff, Ber. 35, 1053). 



[HH.] From acrole'in [101] through 

 propinal and acetylene (see under 

 cymene [6 ; XVIII]), and then as 

 under A above. 



