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Of Oxalic Acid in Concentrated Sulphuric Acid

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Of Oxalic Acid in Concentrated Sulphuric Acid THE CHEMICAI, KINETICS OP THE DECOMPOSITION OF OXALIC ACID IN CONCENTRATED SULPHURIC ACID BY D. M. LICHTY Introduetion A number of carbon compounds are known, which in contact with more or less concentrated sulphuric acid, split off carbon monoxide or a mixture of the monoxide and the dioxide. Potassium cyanide, for example, with ordinary concentrated sulphuric acid at room temperature *yields almost pure carbon monoxide according to the equation KCN + H,O + H,SO, = KHSO, + (NH,)HSO, + C0.l Potassium ferrocyanide, heated with concentrated sul- phuric acid, yields carbon monoxide according to the equation FeK,(CN), + I IH,SO, + 6H,O = CO + 4KHS0, + 6(HH,)HS04+ FeSO,. At first dioxide of carbon and sulphur are also formed.' According to Markownikow and Purgold,' citric acid when heated with water, orbetter withdilutedsulphuric acid at I 60°, is changed to itaconic acid, water and carbon dioxide. Further- more, a mixture4 of one part of dried citric acid and two parts of concentrated sulphuric acid, heated in a water bath, pro- duces at first formic acid and acetone dicarboxylic acid, then Publication Date: January 1, 1906 | doi: 10.1021/j150084a003 five volumes of carbon dioxide and three volumes of carbon monoxide, together with small quantities of other compounds. Formic acid or its salts warmed with sulphuric acid splits into carbon monoxide and water, Downloaded by KTH ROYAL INST OF TECHNOLOGY on September 12, 2015 | http://pubs.acs.org HC0,H = CO + H,O. Wade and Panting : Jour. Chem. SOC.,73, 255 (1898). Dammer: Anorg. Chem., 11,, 351. Zeit. fur Chemie, 1867, 265. Beilstein : Handbuch der organischen Cliemie, I, 836. 226 D. M. Lichty Heated with concentrated sulphuric acid, oxalic acid decomposes into carbon dioxide, carbon monoxide and water according to the equation (CO,H), = H,O + CO, + CO. Dobereiner showed that this decomposition occurs at room temperature in presence of slightly fuming sulphuric acid and that equal volumes of carbon dioxide and carbon monoxide are formed. In concentrated sulphuric acid the decomposition begins at I IO'-I I 5O, according to Gay-Lussac,* already at 100°-~050, according to Turner. ' This difference in the temperature at which the evolution of gas begins, depends, as we shall see, on the degree of concentration of the sulphuric acid used. According to each author there are produced equal volumes of the two oxides of carbon. The two gases are evolved in the same proportions as well when the decomposition occurs in about 98.5 percent sulphuric acid as when it occurs in about 50 percent sulphuric acid, as is shown by the analyses recorded on pp. 24 and 25. Anhydrous oxalic acid heated by itself sublimes unde- composed at 165,5' (Turner) ,4 decomposes, however, at higher temperatures, when carbon dioxide, carbon mondxide and water are the only product^.^ Crystallized oxalic acid, on the ' other hand, when heated, melts at 98' (Gay-Lussac and Turner)6 and decomposes above IIO'-II~', into five vol- umes of carbon monoxide and 6 volumes of carbon diox- ide. This excess of carbon dioxide arises through the Publication Date: January 1, 1906 | doi: 10.1021/j150084a003 simultaneous formation of formic arid. The speed of the decomposition of formic acid, oxalic acid, and potassium ferrocyanide in concentrated sulphuric acid has already been studied by Veley,' but only in respect Ann. Chim. Phys. (2), 19, 83 (1821). Downloaded by KTH ROYAL INST OF TECHNOLOGY on September 12, 2015 | http://pubs.acs.org Ibid., (2), 46, 21s (1831); Liebig's Ann., I, 20 (1832). Liebig's Ann., I, 25 (1832) ; S. Archiv., 38, 159. LOC.cit. Comptes rendus, 82, 750 (1870). 6 LOC. cit. Phil. Mag. [6],6, 277 (1903). Chemical Kinetics of 0xa.lic Acid 227 to the supersaturation of the liquid with the gaseous products, through which the rate at which the gas is evolved increases from the beginning to a maximum and then decreases accord- ing to the bimolecular law. In my judgment this investiga- tion permits conclusions only with respect to the velocity with which the gases voluntarily escape from the super- saturated solution, but nothing with certainty concerning the velocity with which the decomposition of the oxalic acid takes place. In order to get some insight into the kinetics of the reaction between oxalic and sulphuric acid, and possibly into the constitution of concentrated sulphuric acid, the investiga- tion detailed in the following pages was undertaken in the Phys- icochemical Division of the Cheniical Laboratory of the University of Heidelberg under the direction of Prof. G. B redig. Puriflcation and Dehydration of the Oxalic Acid A good quality of commercial acid was dissolved in the smallest possible quantity of boiling water and filtered hot to free it from insoluble impurities. The product obtained from this filtrate was recrystallized three times from hot, about 12 percent, hydrochloric acid and then twice from hot water. During each crystallizatim the solution was cooled with moderate rapidity and stirred constantly to obtain the acid in a fine crystalline powder. After each crystallization the mother-liquor was well aspirated off and the crystals repeat- Publication Date: January 1, 1906 | doi: 10.1021/j150084a003 edly washed with cold water. After pressing carefully be- tween filter paper, the crystallized acid was allowed to lie spread out in the air, protected from dust, to dry. From these crystals the anhydrous acid was prepared by heating at 5oo-6o0 until the weight was constant, and was then pre- Downloaded by KTH ROYAL INST OF TECHNOLOGY on September 12, 2015 | http://pubs.acs.org served in a desiccator over sulphuric acid. A hot saturated solution of the oxalic acid, acidified with nitric acid, gave no turbidity with silver nitrate solution; another acidified with hydrochloric acid gave no reaction for sulphate. Spectroscopically, no potassium was found and 228 D. 111. Lichty only a trace of sodium. About 5 grams of crystals sublimed from a platinum crucible left no weighable residue. The oxalic acid used may therefore be considered as absolutely pure. The Sulphurie Add Samples of sulphuric acid from different sources were used and will be described in detail later. Suffice to say here that the first trials were made with ordinary, about 96 percent, acid or with mixtures of such an acid and a fuming acid (see pp. 231-238). The more exact measurements were made with acid kindly furnished by the “Badische Anilin und Soda- Fabrik (p. 238).” METHOD OF INVESTIGATION A. General Considerations The reaction was allowed to take place in long-necked Erlenmeyer flasks of Jena glass, having a capacity of IOO cc and carrying a charge of 50 cc of solution. These flasks were kept within f0.1’ at a constant temperature in a thermostat of the usual Ostwald type, which was filled with water covered with paraffin oil. Over the neck of each flask was slipped a rubber ring over which in turn was put a close fitting glass cap bearing a short 7 mm outlet tube, bent at right angles. This tube was connected with tubing which led to the hood or which had a drying apparatus attached for protection against the moisture of the air. When samples for analysis were drawn into pipettes they Publication Date: January 1, 1906 | doi: 10.1021/j150084a003 became so filled with bubbles, disengaged from the solutions, saturated or perhaps supersaturated with the gaseous reaction products, that accurate measurements by this means were impossible. For this reason the samples were pipetted into weighing-glasses, cooled in running water, and then either Downloaded by KTH ROYAL INST OF TECHNOLOGY on September 12, 2015 | http://pubs.acs.org accurately measured or more frequently weighed for the analyses. The oxalic acid was determined by means of potassium permanganate solution, the titration having been carried out between 70’ to goo, and at such a dilution that the total volume of liquid at the end amounted to 40 to 50 cc. Chemical Kinetics of Oxalic Acid 229 As the results given below, and obtained with an approxi- mately one-fourth molar solution of oxalic acid in about 96 percent sulphuric acid, show, oxalic acid is but very slowly decomposed by sulphuric acid at room temperature. The figures express the number of cc of a. permanganate solution required for IO grams of oxalic acid solution. Fresh solution.. ................. 55.62 cc After 5 days.. .................55.52 cc After 12 days ................... 54.83 cc In more concentrated sulphuric acid the decomposition proceeds so much faster that it was necessary to dilute the samples at once. This was done by pipetting them into tared and cooled glass stoppered weighing-glasses, containing ' diluted sulphuric (2 volumes 96 percent to I volume water), the quantity of diluted acid having been so chosen as to make the total water in the mixture at least 5 percent. The samples consisting of at least IO grams were then weighed, and the volume of permanganate solution per IO grams calculated from the titration values. B. Method of Handling the Sulphuric Acid and of Diluting It with Water The sulphuric acid was pipetted or siphoned directly from the supply bottle into one provided with a well-fitting glass stopper, and in amounts equal to 250 grams, or such as to make the weight of the water or of 40 percent sulphuric acid required for making the desired dilution, equal to at least Publication Date: January 1, 1906 | doi: 10.1021/j150084a003 IOO mg. In order to secure both the ready mixing of the two liquids and sufficient accuracy in weighing, the water was weighed in tubes open at both ends and widened somewhat in the middle, when the amount needed did not exceed 5 grams.
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