Dr. Simpson on the Action of Acids on Glycol. 473 



Action of Hydrochloric and Acetic Acids on Glycol — Chloracetine 

 of Glycol. — A mixture of equivalent quantities of glycol and glacial 

 acetic acid was introduced into a long tube and saturated with dry- 

 hydrochloric acid. The tube was then hermetically sealed, and ex- 

 posed to the temperature of a water-bath for about four hours. On 

 opening the tube and adding water to its contents, a heavy oil sepa- 

 rated, which was well washed with the water, in order to remove any 

 acetic acid or uudecomposed glycol it might contain, dried over chlo- 

 ride of calcium, and distilled. Almost the entire quantity passed 

 over between 144° and 146°. Specimens obtained at different times 

 gave the following numbers on analysis, which lead to the formula 



CI 



Cg 48-00 39-18 38-96 38-98 



H, 7-00 5-71 6-05 599 



O^ 32-00 26-14 



CI 35-50 28-97 27-48* 



122-50 100-00 

 I propose to call this body chloracetine of glycol. It is the inter- 

 mediate compound between Dutch liquid and diacetate of glycol. Its 

 formation may be thus explained : — 



^'h l^^+ ^^g^^4o., + HCl=^'JJ^Q |0, + 4H0. 



Chloracetine of glycol is a colourless liquid, heavier than water, 

 its specific gravity being 1-1783 at 0° Cent. It boils at 145°, distil- 

 ling without decomposition. It is not decomposed by cold water, at 

 least not to any great extent ; even boiling water effects its decom- 

 position with difficulty. Heated with potash, it gives chloride of 

 potassium and acetate of potash. It is probable that the ether of 

 glycol is also formed in this reaction, or perhaps glycol itself. This 

 point I have not yet been able to determine. Chloracetine is iso- 

 meric with a compound I obtained a short time ago, by exposing 

 ordinary aldehyde to the action of chloride of acetyle (C^H3 0,Cl)t. 

 This body differs from the chloracetine in its boiling-point, which is 

 about 23 degrees lower, and in being more readily decomposed both 

 by water and potash. The products formed by the action of potash 

 also establish a difference between these bodies. Both give chloride 

 of potassium and acetate of potash, but the body from aldehyde gives, 

 in addition, resin of aldehyde ; whereas from chloracetine no resin 

 could be obtained. (Chloracetine has since been prepared by 

 M. Lorenzo in a manner analogous to that by which I prepared its 

 isomer, namely, by treating glycol with chloride of acetyle. These 

 compounds find their places in two verj' remarkable series of iso- 

 meric bodies, proceeding from ethylene (defiant gas) and ethylidine 

 (C^ H^ ?), supposed to be contained in aldehyde and in the chloride 

 of ethylidine C, H, CI.,. The following is a list of these compounds : — 



* A slight loss occurred in this analysis, 

 t Comptes Rendus, 29 Nov, 1858. 



