A general procedure for the determination of oxirane oxygen is described. The method, originaIly proposed by Nicolet and Poulter, is based upon the quantitative opening of the oxirane ring by means of a 0.2 N solution of anhydrous hydrogen chloride in absolute ethyl ether. The method is specific for the determination of oxirane oxygen, it may be employed N STUDYIXG the mechanism of the air oxidation of unsatu-I rated fatty materials, it is essential to determine the quantity of each of several types of oxygen-containing groups in the product. It is customary to analyze for hydroxyl, carboxyl, carbonyl, and ester oxygen, but no work has been reported on the determination of oxirane oxygen (-C-C-) in such materials, even I I \/ 0 though it is well known that oxirane compounds are formed during the air or oxygen oxidation of unsaturated compounds (3, 4).Recently, Hilton (6) has suggested a method for determining oxirane oxygen in oxidized rubber, the basis for which is the reaction of diethylamine with the oxirane group under pressure in a sealed tube, followed by analysis of the reaction product for nitrogen. This method is time-consuming and inconvenient, and it is not suitable for control work. The method of Nicolet and Poulter (r), however, appears to be admirably suited for the analysis of air-oxidation reaction mixtures for oxirane oxygen. This method which is based upon the quantitative opening of the oxirane ring by means of a solution of anhydrous hydrogen chloride in absolute ethyl ether (Equation 1) :(1)was applied by them only to the analysis of the 9,lO-epoxystearic acids, derivable for oleic and elaidic acids. But whether the method is specific for oxirane oxygen and whether it is applicable to a variety of oxirane compounds in which the oxirane group is a t different positions in the molecule had to be determined before it could be employed for the analysis of air-oxidation mixtures. REAGENTS in the analysis and determination of the purity of a wide variety of oxirane compounds, and it is suitable for the determination of oxirane oxygen in air-oxidation reaction mixtures. The reaction of anhydrous hydrogen chloride with oxirane compounds in absolute ethyl ether solution is suggested as a general method for preparing chlorohydrins. heavier solid stopper.) Liquids are weighed by difference from dropping bottles; solids are weighed into tared flasks. The maximum weight of sample should be taken only when it is known that the oxirane oxygen content lies near the minimum value of the range given. Adherence to these values will ensure a proper (at least 100%) excess of hydrochloric acid-ether solution. Wash down the sides of the flask with 5 ml. of absolute ethyl ether and add exactly 25 ml. of the hydrochloric acidether solution. Stopper the flask and swirl gently to dissolve the sample. Allow the solution to stand for 3 hours at room temperature. .4dd 50 ml. of 95% ethyl alcohol and 1 ml. of the phenolphthalein indicator solution, and titrate the excess acid with 0.1 S sodium hydroxide solution. Conduc...
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.