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Proceedings Chemical Society View Article Online / Journal Homepage / Table of Contents for this issue Issued 23/11/06 PROCEEDINGS OF THR CHEMICAL SOCIETY. VOl. 22. No. 316. Thursday, November 15th, 1906, at 8.30 p.m. Professor R. MELDOLA, F.R.S., President, in the Chair. Messrs. J. Campbell Brown and W. H. Hnrtley wer8 forinally admitted Fellows of the Society. Certificates were read for the first time in favour of Messrs. : Frank Stanley Benton, Huratead, Iteigate. John Trevor Cart, B.Sc., A.I.C., 4, Simon side Tei*racc, Heaton, Published on 01 January 1906. Downloaded by State University of New York at Stony Brook 30/10/2014 07:12:26. Newcastle-on-Tyne. George William Clough, B.Sc., 29, Oseney Crescent, N.W. Victor George Jackson, 21, Frankfurt Road, Herne Hill, S.E. Louis Murgatroyd, 1, Cdton Drive, Heaton, Bradford. Robert Robertson, M. A., D.Sc., F.I.C., 9, Sewardstone Road, Waltham Abbey. Arthur Henry Salway, Ph.D., B.Sc., 15, Palmerston Road, Forest Gate, E. Robert Low Smith, 56, Genesta Road, Plumsted, S.E. William Sandilands Templeton, M. A,, RSc., Colombo, C'uylon. Maximilian Toch, 261, West "1st Street, New Pork City, U.S.A. A. certificate mas authorised by the Council for presentation to ballot under Bye-Law I (3) in favour of : Tarak Nath Majumdar, 37, Lower Chitpore Road, Calcutta, India View Article Online 280 Of the following papers, those markcd * were mad : *203. (‘The determination of the rate of chemical change by measurement of gases evolved. Preliminary notice.” By Francis Edward Everard Lamplough. The most important results of this investigation may be summarised as follows : When a chemical reaction takes place in solution resulting in the formation of a substance which is gaseous at the ordinary temperature, the solvent becomes supersaturated with the gas. The degree of supersaturation may be so great that the solvent con- tains 100 times the normal amount of the gas, and from such a solution the gas is gradually evolved. The excess of gas so dissolved may be almost entirely expelled in thirty seconds by briskly agitating the liquid, Investigation of the rate of decomposition of hydrogen peroxide showed that under such conditions of efficient stirring, the rate of evolution of a gas furnishes an accurate and reliable method of investigating reactions of this nature. The decomposition of diazobenzene chloride was shown to be strictly a unimolecular reaction throughout, the rate of which is independent of the amount of acid present. The value of the constant for the reaction was found to vary with change of temperature, increasing logarithmically with increase of temperature. The nature of the decomposition of ammonium nitrite most nearly approaches that of a quadrimolecular reaction throughout the extent of decomposition investigated. The decomposition of formic acid by sulphuric acid is a true uni- molecular reaction, and not bimdecular, as it has been hitherto Published on 01 January 1906. Downloaded by State University of New York at Stony Brook 30/10/2014 07:12:26. considered. The reaction between nickel carbonyl and iodine has also been studied. DISCUSSION. Dr. CAIN pointed out that Hantzsch had first shown that the value of the constant obtained in measurements of the rate of decomposition of diazo solutions was low at the beginning of an experiment, owing to the solubility of the nitrogen. There was no supersaturation, however, in the solutions used in the experiments by him (Dr. Gain) and Mr. Nicoll, for the deficit in the quantity of nitrogen evolved corresponded to the amount which would ordinarily remain in solution. Moreover, the values obtained for the constants agreed well with those given by Hantzsch, Euler, and other investigators, View Article Online 281 Mr. CALDWELLasked if there were any real retardation of these reactions when the solutions were not stirred. The accumulation of large amounts of the gaseous product existing in a highly super- saturated state in the solution might tend to make a reaction reversible. Mr. LAMPLOUGHin reply stated that the method adopted for the preparation of the diazobenzene chloride was that described by Dr. Cain in his paper. The solution was raised to the desired tempera- ture in 15-30 seconds. As evidence that supersaturation was really present the author referred to an actual comparison experiment, showing the volume of gas evolved from solutions stirred and not stirred, where it was seen from the lantern slide exhibited that at one time 37 C.C. of the solution at 62’ held supersaturated 22 C.C. of nitrogen, or more than thirty times the amount calculated from the solubility of the gas. The author also gave numbers showing the great difference between his constants for the reaction and those determined by Gain and Nicoll. A reaction resulting in the evolution of carbon dioxide had been studied, but owing to the greater solubility, the degree of super- saturation was small, and at present the author had not sufficient data to say whether a highly supersaturated solution is more easily formed in the case of the more insoluble gases. In the comparison experiments on the decomposition of hydrogen peroxide in which the rates of reaction were determined by measurement of the gas evolved from the stirred solution and by titration respec- tively, in the latter case the solution was not stirred, and therefore the close agreement in the results showed that the rate of evolution of gas from the stirred solution also measured truly the rate of reaction in the still liquid. Moreover, if the reaction is allowed to begin Published on 01 January 1906. Downloaded by State University of New York at Stony Brook 30/10/2014 07:12:26. without agitation and at a given time the solution is suddenly stirred, an immediate evolution of gas takes place, making the total volume of gas evolved equal to the amount given off in the same time with stirring, thus showing that stirring does not influence the rate of the reaction, but simply gives a correct method of measuring it. “204. The formation and reactions of imino-compounds. Part XI. Condensation of benzyl cyanide leading to the forma- tion of l : 3-diaminonaphthalene and its derivatives.” By Ernest Francis Joseph Atkinson and Jocelyn Field Thorpe. Benzyl cyanide condensss with its sodium derivative to form p-imino-a-cyano-ay-diphenylpropane(l), which on treatment with View Article Online 28.2 sulphuric acid is coinpletely converted into 1 : 3-dianaino-2-phenyl- naphthalene (2) . (11 (2) Benzyl cyanide also combines with the sodium derivative of ethyl cyanoacetate, forming ethyl p-iinino-a-cyano-y-phenylbutyrate(3), from which on treatment with sodium ethoxide and either methyl or ethyl iodide, etJql p-inaino-a-cpno-yy-~l~en~lrnetl~~lbutyrate (4), or ethyl P-imino-a-c?/ano-yy-;plze?zyletJ~~t~~t~~.ate(5) can be prepared. From these compounds on treatment with sulphuric acid ethyl 1 : 3-diamino- naphthalene-2-carboxylate (6), ethyl 1 : 3-diai,zino-4-metl~yZnaphtha~- ene-2-carboxylute (7), and ethyl 1 : 3-diamino-4-ethyZ~aaphtl~alene- 2-curboxylate (8) are f orined respectively : NH. C-,CHEt C6H5 CH2-- 7GH4 CH(CO,Et)* CN NH:C<C H(CO,E t ) C: NH (7) (8) The, ethyl esters (6), (7), and (8) are converted on hydrolysis into the corresponding car6oxylic acids, which on heating above their melting points are transformed into 1 : 3-diaminonaphthalene (9), 1 : 3-dicrmino- $-nmY@aaphthalene (1 0), and 1 : 3-diamino-4-ethylnuphthalene (1 l), respectively : Published on 01 January 1906. Downloaded by State University of New York at Stony Brook 30/10/2014 07:12:26. DISCUSSION. The PRESIDENTpointed out that the very elegant synthetical method of obtaining 1 : 3-diaminonaphthalene made known by the authors might prove of great practical use in preparing this base in quantity. The method hitherto available, in which dinitro-a-acetnaphthalide is. the starting point, is both circuitous and costly. View Article Online 283 In reply to a question from Mr. Lees, Dr. THORPEsaid that only primary nitriles reacted to form the imino-compounds; one of the two nitriles entering into the reaction must contain the group CII,.CN. *205. (( Note on the anhydride of phenylsuccinic acid.” By Francis Bernhard Dehn and Jocelyn Field Thorpe. The authors have investigated the anhydride of phenylsuccinic acid and conclude that it exists in only one form, which melts at 53-54”, They have been unable to prepare the other form of the anhydride melting at 150’ desccibed by Bredt and Kallen and by Wegscheider and Hecht, but by following the experimental details given by those investigators they have isolated an impure form of the acid which melts at this temperature. The authors have been unable to confirm the observation of Wegscheider and Hecht that the anhydride melting at 53-54’ gradually passes into that melting at 150’ when kept at the ordinary temperature and also at 100’. They have kept specimens of the pure anhydride for several months under these conditions and have observed no change. *206. “Influence of sodium arsenate on the fermentation of glucose by yeast-juice.’’ (Preliminary notice.) By Arthur Harden and William John Young. It has been previously shown that when a soluble phosphate is added to yeast-juice containing glucose, the rate of fermentation is greatly increased (5 to 10 times), and proceeds at a gradually diminish- Published on 01 January 1906. Downloaded by State University of New York at Stony Brook 30/10/2014 07:12:26. ing rate until an extra amount of carbon dioxide (equivalent, molecule for molecule, to the phosphate added) has been evolved. The rate then becomes equal to, or somewhat greater than, that of the original juice to which no addition has been made.
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