Pentachloride of Phosphorus on Malic Acid. 281 



From considerations which we shall not discuss here, it ap- 

 peared probable that malic and tartaric acids might be produced 

 from succinic acid by a process similar to that by which we ob- 

 tained glycolic and glyoxjdic acids from acetic acid, namely, by 

 treating bromine or chlorine replacement acids derived from 

 succinic acid with the hydrate of silver or potassium. Thus 

 ■with monobromo-succinic acid we should expect the following 

 reaction : — 



Malic acid. 

 And with bibromo-succinic acid the following : — 



Tartaric acid. 

 We are now endeavouring to obtain the bromo- or chloro- 

 succinic acids, so that we may fully investigate this matter. 



The late experiments of Wurtz on lactic acid show that when 

 it is distilled with pentachloride of phosphorus, it yields a sub- 

 stance, C^H^O^CP, which has since been shown to be the 

 chloride of chloropropionyle ; for by the action of water it is 

 converted into chloropropionic acid, which, when acted upon by 

 nascent hydrogen, is converted into propionic acid. 



We may here mention that we have made similar experiments 

 witli glycolic acid. This substance, when distilled with penta- 

 chloride of phosphorus, yielded oxychloride of phosphorus and 

 chloride of chloracetylc, which with water decomposed into hy- 

 drochloric and chloracetic acids ; and this chloracetic acid was 

 converted into acetic by the action of nascent hydrogen. 



With these results before us, it appeared probable, if malic 

 acid stood to succinic acid as lactic and glycolic stand to pro- 

 pionic and acetic, that by treatment with pentachloride of phos- 

 phorus it would yield a chloride which would represent the 

 chloride of chlorosuccinyle, C«(H3 C\)0\ CP. 



We have made this experiment, and obtained the following 

 results : — 



One part of malatc of calcium was well mixed with four of 

 pentachloride of ])liospliorus ; this was then placed in a retort 

 connected with a receiver and suitaljle apparatus for absorbing 

 liydrochloric acid. On applying heat to the retort for a few 

 moments, chemical action set in and continued for some time; 

 after it had ceased, heat was again applied until no more liquid 

 distilled over. 



Phil. Muij. S. 4 Vol. 17. No. 114. April 1859. U 



