75 per cent sulfuric acid in the liquid phase was made a few years ago (5), and the value 34.15 kg.-cal. per mole of acid reacted at 60°C. to form butylsulfuric acid (as determined in the acid reaction product) was reported.Review of the data, however, shows that an assumption was made which probably is not justified, particularly in light of the above findings. It was assumed that all of the butenes reacting with 75 per cent sulfuric acid form butylsulfuric acid. The present investigation shows that acid extracts of the butenes prepared with 75 per cent acid would undoubtedly contain less than 30 per cent of the butenes as products of sulfation. The calculated heat value, therefore, is probably several hundred per cent too high.Literature Cited
Dibbnzofuran-2-sulfonic Acid and its Alkali Salts 1593 VIII (0.2 g.) was dissolved in 8 ml. of ethanol and converted to the 2,4-dinitrophenylhydrazone by treatment with a solution of 0.16 g. of 2,4-dinitrophenylhydrazine in 0.8 ml. of sulfuric acid and 1.2 ml. of water, diluted with 4 ml. of ethanol. The mixture was heated at the reflux temperature for two hours after the appearance of a precipitate. On cooling, filtering and washing with cold alcohol a yield of 0.25 g. (88%) of the dinitrophenylhydrazone was obtained, m. p. 169-170°. After recrystallization from ethanol-ethyl acetate, acetonitrile and chloroform-carbon tetrachloride, the derivative was a crystalline crimson powder with a constant m. p. of 177-178°.
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The problem of identifying organic compounds ought to be examined periodically to determine whether a reorganization of existing information may simplify the experimental solution. Much information on organic acids is dispersed in the literature, but a general treatment aimed at many varieties of acids is missing. Acids may be considered as derivatives of many other types of compounds convertible to acids. Organic acids containing carbon, hydrogen, and oxygen only can be divided into four well-defined classes based on common physical properties and simple chemical tests.Identification of the drying oil acids calls for ultraviolet absorption studies, or chemical processes of bromination, hydroxylation, and isomerization.Practical significance of the work lies in the increased ease of identification of a large number of compounds encountered frequently in research and industrial operations.ALTHOUGH several systems for identification of organic com-IX pounds have come into common use-e.g., those of Kamm (9), Shriner and Fuson (34), and Huntress and Mulliken (7)improvements seem desirable. The system offered here aims at the identification of organic acids containing carbon, hydrogen, and oxygen (Order I acids of Huntress and Mulliken). Such a system possesses considerable generality because the acids frequently serve as suitable derivatives of many other types of compounds. Thus, easy identification of acids may mean rather easy identification of esters, aldehydes, primary alcohols, methyl ketones, nitriles, and amides, in addition to several types of hydrocarbons. The alkenes, cyclenes, and alkyl benzenes are easily characterized (36); permanganate or nitric acid oxidation generally forms an acid identifiable by the present system.Despite structural variations that may defy general treatment in any given series of compounds, the individual carboxylic acids fall into well-defined groups. For instance, a liquid acid having a sour odor, partially miscible with water, with density less than 1.0, whose alkaline solution is not soapy, would necessarily be an acyclic mono acid with 5 to 10 carbon atoms; a second acid, differing from the first only by displaying a density greater than I. 0 would have to be a cycloalkane mono acid, such as cyclohexylacetic acid. Ultimate identification of the unknown characterized in this manner would then hinge on ascertaining two or three additional properties, density, refractive index, etc., or melting points of one or two derivatives. In order to employ properties and characteristics most easily observed in the laboratory, the authors have set up a classification based on the following considerations: Class I includes liquid acids melting at 30°C. or lower. Classes II, III, and IV include solid acids melting above 30°C.Class I is subdivided according to odor, miscibility with water, density, character of alkaline solutions (soapy or not), reaction with aqueous permanganate, and determination of neutral equivalent.Classes II and III are subdivided according to limits imposed on melting ...
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