( 202 ) 



The method, however, appeared iiiipraclieable as the ehlorocyelo- 

 hexaiie was not readily converted into the alcohol. Makkownikoff 

 has tried to attain this by using alcoholic potash ; we have tried it 

 by shaking the said chloro-conipound for several days and at different 

 temperatures with silver oxide and water -f- alcohol, but a trans- 

 formation worthy of the name was not conti'olled. 



The chlorination of cyclohexane in quantities of 80 — 100 grams 

 to the monochlorocompound was moreover a disagreeable and slow 

 operation. The most satisfactory results were obtained by Makkowmkoff's 

 first method (A. 301, 184) by pouring the hydrocarbon on to water 

 in a Drephsel flask and then passing chlorine into the water at 30 — 40^. 

 The influence of light is very pronounced in this case. Direct sunlight 

 causes explosion. If chlorine is passed through the hydrocarbon 

 exposed to faint light it dissolves with a yellow colour. If now this 

 solution is exposed to sunlight a violent evolution of hydrogen chloride 

 takes place ; in strong light this is accompanied by luminous i)henomena. 



Mr. VAN DER Laan, howe^■er, succeeded in readilj- preparing 

 ketohexamethylene by another process. It appeared that phenol and 

 hydrogen combine to hexahydrophenol by the method of Sabatier 

 and Senderens and that the cyclohexanol obtained could then be 

 oxidised to the corresponding ketone: 



C,H,OH + 3H, = C,H,,OH ; C,H,,OII -j- = C,EJ) -f II./l 



For the preparation of cycloliexanol 0,H„OH a combustion tube 

 was quite filled wqth iiickeloxide Avhich w\as tlien reduced by means 

 of pure hydrogen. By means of an aebestos stopper, one end of the 

 tube was connected with a wash-bottle containing phenol; this was 

 placed in an airbath heated to 160—170°. The tube was placed in 

 a combustion furnace in an iron gutter lined with asbestos. The bulbs 

 of two thermometers were also placed in the gutter and the flames 

 were so regulated that they showed 140— 160 \ By means of another 

 asbestos stopper, the other end of the tube Avas connected with an 

 adapter leading into a flask closed with a doubly-perforated cork. 

 Through the second hole w\as passed a gas exit tube by means of 

 which the absorption could be controlled. 



The current of pure and dry hydrogen which Avas passed into the 

 wash-bottle containing the phenol charged itself with vapour which 

 m the presence of an excess of hydrogen was exposed to the catalytic 

 action of the nickel. 



In the receiver a Hquid consisting of two layers collected, the bottom 

 layer being ^vater. 



The top layer was submitted to distillation. From 85°— 110° a liquid 



