HYDROCARBONS 



[1 A-D. 



manganese, lanthanum, yttrium, ura- 

 nium, and thorium, praseo- and neo- 

 didymium produced in the electric fur- 

 nace give methane (in most cases mixed 

 with other gases) when acted upon by 

 water (Moissan, Proc. Roy. Soc. 60, 

 156; Bull. Soc. [3] 11, 1012 ; 15, 1285 ; 

 >. Rend. 



17, 15 ; Comp. 



122, 362; 423 



1462 ; Ann. Chim. [7] 9, 302 ; Moissan 

 and Etard, Ann. Chim. [7] 12, 429; 

 Lebeau, Comp. Rend. 121,498; Moissan, 

 Comp. Rend. 131, 595; Berthelot, Comp. 

 Rend. 132, 281). 



Carbon and hydrogen combine directly 

 to form acetylene when the electric arc 

 passes between carbon poles in an at- 

 mosphere of hydrogen (Berthelot, Ann. 

 Chim. [4] 13, 143; Comp. Rend. 54, 

 640 ; Bone and Jerdan, Trans. Ch. Soc. 

 71, 41 ; 79, 1042). Or certain metallic 

 carbides, such as those of barium, cal- 

 cium, strontium, and lithium prepared in 

 the electric furnace, give acetylene when 

 acted upon by water (Moissan, Bull. Soc. 

 [3] 16, 1285 ; the production of acety- 

 lene from calcium carbide and water was 

 first observed by Wohler, Ann. 124, 220 : 

 the technical production of calcium car- 

 bide is due to Willson, 1894. Wohler 

 prepared calcium carbide by strongly 

 heating an alloy of zinc and calcium with 

 charcoal : Maquenne prepares barium 

 carbide by heating barium carbonate 

 with magnesium powder and carbon ; 

 Ann. Chim. [6] 28, 266). Acetylene 

 gives methane when passed over finely 

 divided nickel heated to 300 (Sabatier 

 and Senderens, Comp. Rend. 124, 617) 

 or when heated per se to 1 150 (Bone and 

 Jerdan, Proc. Ch. Soc. 17, 164). Or 

 acetylene forms a compound with mer- 

 curic chloride (see under acetaldehyde 

 [92; A]), and this on treatment with 

 iodine and alkali gives iodoform (Le 

 Comte, Journ. Pharm. 16, 297). From 

 iodoform as under D below. 



Carbon monoxide and hydrogen give 

 methane under the influence of the silent 

 electric discharge (Brodie, Proc. Roy. 

 Soc. 21, 245 ; Ann. 169, 270). So also 

 (probably) does a mixture of carbon di- 

 oxide and hydrogen (Collie, Trans. Ch. 

 Soc. 79, 1067). Methane is produced 

 by the catalytic action of finely divided 

 heated nickel or cobalt on a mixture of 



hydrogen with carbon dioxide or mon- 

 oxide (Sabatier and Senderens, Comp. 

 Rend. 134, 514; 689). 



[B.] Heptane [2] gives methane among 

 the gases produced by heating the hydro- 

 carbon to 900 (Worstall and Burwell, 

 Am. Ch. Journ. 19, 815). 



[C.] From methyl alcohol [13] through 

 methyl iodide and the action of sodium 

 on the moist ethereal solution or of the 

 copper-zinc couple or aluminium amal- 

 gam on the alcoholic solution of the 

 iodide (Gladstone and Tribe, Trans. Ch. 

 Soc. 45, 154; Wright, Ibid. 47, 200 ; 

 Bone and Wheeler,lbid. 81,541). Magne- 

 sium amalgam reduces the alkyl iodides 

 more readily than the copper-zinc couple 

 (Meunier, Comp. Rend. 134, 47 2). Me- 

 thyl iodide (or chloride) gives methane 

 by heating with potassium hydride 

 (Moissan, Comp. Rend. 134, 389). Or 

 from methyl iodide through zinc methyl 

 (Frankland, Ann. 85, 346 ; 111, 62) and 

 decomposition of the latter by water 

 (Ibid. Phil. Trans. 1852, 2, 417 ; Laden- 

 burg and Kriigel, Ber. 32, 1821), or by 

 alcohol in an atmosphere of nitrogen or 

 hydrogen (Tolkatscheff, Journ. Russ. 

 Soc. 33, 469). Magnesium methiodide 

 gives methane on decomposition by water 

 (Grignard, Ann. Chim. [7] 24, 433 ; 

 Tschugaeff, Ber. 35, 3912). 



From methyl alcohol by passing the 

 vapour over heated magnesium (Keiser 

 and Breed, Ch. News, 71, 118), or by 

 passing the electric arc through the va- 

 pour (Lob, Ber. 34, 917), or by pyro- 

 genic contact decomposition (Ipatieff, 

 Ber. 35, 1055; 1060). From methyl 

 alcohol through methyl ether (Dumas 

 and Peligot, Ann. 15, 12 ; Kane, Ann. 

 19, 166 ; Ebelmen, Ann. 57, 328 ; 

 Erlenmeyer and Kriechbaumer, Ber. 7, 

 699 ; Tellier, Arch. Pharm. 10, 57). 

 The latter gives methane on passing 

 through a hot tube (Tischtschenko, Ch. 

 Centr. 1900, 1, 586, from Journ. Russ. 

 Soc. 31, 784). 



[D.] From ethyl alcohol [14] through 

 chloroform (Liebig, Ann. 1, 198 ; Sou- 

 beiran, Ann. Chim. [2] 48, 131; Sou- 

 beiran and Mialhe", Ann. 71, 225; 

 Kessler, Journ. Pharm. 13, 162; Belo- 

 houbek, Ann. 165, 349 ; Goldberg, 

 Journ. pr. Ch. [2] 24, 114 ; for electro- 



