258 THANN AND WANKLYN ON THE ACTlON OF XXTI.-Action of Metals upon Iodide of Ethylene C4€1412. By CARLVONTHANand J. A. WANKLYN. WHENzinc acts upon iodide of ethyl it combines both with the iodine and with the ethyl producing iodidc of zinc and zinc-ethyl. METALS UPON IODIDE OF ETHYLENE In like manner it seemed possible that zinc would act upon iodide of ethylene in such a manner as to give iodide of zinc and a compound of zinc with the biatomic radical ethylene thus :-(C,H,)"I + Zn = (C,H,)"Zn + Zn,I We have tried the experiment using ether to dissolve the iodide of ethylene and obtained a negative answer as regards the production of a compound of the biatomic ethylene with zinc. Our research was conducted as follows :-The iodide of ethylene was prepared by passing olefiant gas over iodine gently warmed with hot water.The product was freed from excess of iodine by means of a solution of caustic potash washedand dried by pressure between folds of bibulous paper; afterwards it was exposed for a short time in vacuo over sulyhuric acid. The ether was dried by standing over solid caustic potash. The zinc mas pretty pure and finely granulated. A few grammes of this iodide of ethylene were introduced into a glass tube along with zinc and ether and hermetically sealed therein before the blowpipe. The tube so prepared was kept at ordinary temperatures and in the dark. Large quantities of a combustible gas were gradually evolved This gas was allowed to escape from time to time by opening the tube; and some of it was collected over water transferred to the mercurial trough and aiialysed when it proved to be perfectly pure olefiant gas as the following particu- lars of rhe analysis show :-Volume Pressure in Metres.I---I-I I Tempe-rature Centi-grade Volume at 1 metre and 0°C. Volume of gas taken . . . . . . . . 83 *5 0 -1483 1'7.8" 11 *61 After the addition of oxygcn .. .. 46'7'6 0 5272 17.7" 231 5 After the explosion . . . . . . . 440.8 0 5022 11.5" 208 '1 After the absorption of carbonic acid . . 409-8 0 -4860 20.9" 185 0 Found Calculated for C4H4 Volume taken . . 11-61 1106% Contraction . . . 23-40 23.24 Carbonic acid . 23.10 23-24 Oxygen consumed 34.89 34.86 260 THANN AND WANKLYN ON THE ACTION OF That the gas was not a mixture having the same percentage composition and condensation as ethylene was proved by its complete absorption by fuming sulphuric acid.The residue in the production tube consisted apparently of nothing beyond iodide of zinc dissolved in ether. Some of the contents were withdrawn and treated with water with which they did not effervesce ; the rest were distilled directly fkom the produc- tion tube a cork and bent tube having been previously adapted thereto. This distillation i~ascommenced in the water bath and finished over the naked flame. No product containing zinc dis- tilled over. No compound of ethylene and zinc seems there- fore to be formed by this process and the reaction which actually takes place may be thus written :-(C4H4)”IQ+ Zn = C[H4 + Zn,I With other metals we have obtained similar results.Sodium with ethereal solution of iodide of ethylene evolves gas rapidly at ordinary temperatures. This gas was evidently ethylene as it was soluble in fuming sulphuric acid after it had been free from ether vapour by washing with water. The iodide of sodium which formed simultaneously with the gas was coloured blue. A blue coloration of iodide of sodium had been previously remarked by one of us when iodide of ethyl ether and sodium are brought together. Mercury also evolves gas when placed in an ethereal solution of iodide of ethylene. In that case the evolution takes place slowly; but ultimately an immense quantity of gas is given off even when the experiment is conducted at ordinary temperatures and with exclusion of light.At the same time iodide of mercury makes its appearance and gradually assumes the red modification. No signs of any combination between ethylene and mercury were observable. We have also extended our experiments to chloride of ethylene (C4H4)”C12 (Dutch liquid). This liquid mixed with-dry ether is not acted upon by zinc either at ordinary temperatures or in the water bath. By sodium however it is attacked when gently warmed even though the heating falls considerably short of 100OC. Olefiant gas and blue chloride of sodium are the products. The gas was collected over water and subsequently treated with strong sulphuric acid by which it was perfectly absorbed proving tha entire absence of frce hydrogen.NETBLS UPON IODIDE OF ETHYLENE. The reactions established in this paper are of interest in relation to the theory of biatomic radicals and may be regarded as cases in which the biatomic radical ethylene is isolated. Just as under certain conditions iodide of ethyl yields ethyl when acted upon by zinc so does iodide of ethylene yield ethylene when treated with that metal. The parallelism bet ween the following equations is obvious :-~(c,H,I) + Zn = z~,I,+ 3:s-j-45 (C4H,)”I + Zn = Zn,T -k C,”H4 It is our intention to seek for metallic combinations of the biatomic radical ethylene by the employment of other methods than the one mentioned in this paper.