64 KANSAS ACADEMY OF SCIENCE. 



II. 0.4108 gram substance required 28.20 cc. AgNOs solution, rep- 

 resenting 0.0984 gram CI. 



III. 0.3450 gram substance required 23.53 cc. AgNOs solution, 

 representing 0,0821 gram 01. 



Calculated for Found. 



CI-SO2-OC2H.5. I. II. III. 



S 22.18 22.51 



01 24.52 .... 23.96 23.80 



Ohlorsulphonic ethyl ester is a colorless, limpid liquid, possessing 

 a sharp, pungent odor, irritating to the eyes and exciting tears. Its 

 boiling-point under a pressure of 14 mm. is 52°, and under 20 ram. 

 58"^. The specific gravity is 1.3630 at 18^ It is soluble in ligroin, 

 chloroform, and ether, but attacks ether when warmed. It is also 

 soluble in fuming nitric acid, and is precipitated unchanged by the 

 addition of water. Water affects it only slightly in the cold, even 

 after standing with it for weeks ; but on heating, decomposition 

 quickly sets in. Thus, 4.8 grams of the ester heated in a distilling 

 flask containing 40 cc. water, gave 150 cc. of ethyl chloride, or 16 

 per cent, of the theoretical amount. The decomposition of the ester 

 by alcohol has been shown by Claesson to yield ethyl chloride, hy- 

 drogen chloride, ethyl sulphuric acid, ether, and a small amount of 

 diethyl sulphate. 



ACTION OF CHLORSULPHONIC ETHYL ESTER UPON SODIUM ALCOHOLATES. 



1. Upon Sodium Ethylate. Twenty-five grams (2 niols.) freshly 

 prepared sodium ethylate, dried at 180° in a hydrogen stream under 

 reduced pressure, were suspended in 100 grams purified gasoline 

 ( b. p. 110°-125°). Twenty-five grams ohlorsulphonic ethyl ester were 

 slowly added by means of a dropping funnel, the mixture being con- 

 tinually agitated and kept cool in an ice-salt freezing mixture. After 

 the ester had all been added, the temperature was allowed to rise to 

 about 10°, and was kept there until the odor of the ester was no longer 

 noticeable. The gasoline solution was then decanted, filtered, and 

 subjected to distillation from a water-bath, and yielded ethyl ether, 

 which after rectification weighed 2.85 grams. The residue of salts 

 was washed with absolute ether and the washings were added to the 

 gasoline from which the ether formed in the reaction had been re- 

 moved as above described. On then removing the ether and gasoline 

 by distillation at reduced pressure, 9.92 grams diethyl sulphate, dis- 

 tilling between 96° at 18 mm. and 96° at 14 mm., were obtained — a 

 yield of 32.2 per cent. After being washed with ether, the salts were 

 dissolved in water and the solution was saturated with carbon dioxide, 

 then evaporated to dryness under reduced pressure. By digestion 

 with absolute alcohol, 12.2 grams sodium ethyl sulphate were obtained 



