It resembles the hydrochlorate in its properties, but is much more soluble in boiling spirit, and forms larger crystals. Furfuraniline sulphate.-When 23 parts aniline and 35 of its sulphate were dissolved in 3000 of boiling alcohol, and 24 parts of furfurol in 200 of boiling spirit added, the mixture became deep red, and on cooling deposited minute purple needles of the furfuraniline sulphate, contaminated, however, with colourless crystals of aniline sulphate. When an attempt was made to separate these by crystallization from alcohol, the furfuraniline salt was mostly decomposed, with formation of aniline sulphate, which crystallized out. Furfuraniline oxalate.-When aniline oxalate of aniline and furfurol were dissolved in spirit, as in the preparation of the salts above described, the solution became of a deep red colour, but did not yield crystals of oxalate of furfuraniline, only oxalate of aniline and a dark red tarry matter being produced. Furfuraniline.-In order to obtain this base, a salt of furfuraniline (the hydrochlorate or nitrate) was ground up to a paste with water and strong aqueous ammonia added, the whole being intimately mixed until the purple colour disappeared, giving place to a pale brown. Warm water was then added until the liberated base became soft and plastic, so that it could be needed in successive quantities of warm water, in order to remove the ammoniacal salts and free ammonia. The base, as thus prepared, has much the pale brown glossy appearance of stick lac, and, like it, can be drawn out into strings when soft. It is insoluble in water, but very soluble in ether and alcohol, and when hydrochloric acid is added to a strong spirituous solution it becomes deep red, and solidifies in a few moments to a mass of the purple crystals of the hydrochlorate. The base decomposes, however, very rapidly when exposed to the air, or when boiled with alcohol, and will then no longer yield crystalline salts with acids. The same effect takes place, but more slowly, in a vacuum. Action of Furfurol on Toluidine Furfurtoluidine. When alcoholic solutions of toluidine and furfurol were mixed, there was no immediate change; but after standing some time they acquired a red colour as in the corresponding reaction with aniline no crystalline sabstance was produced. Furfurtoluidine hydrochlorate. The method employed to obtain this salt was similar to that used in preparing furfuraniline hydrochlorate: 12 parts toluidine hydrochlorate and 9 parts crystalline toluidine were dissolved in 150 parts hot spirit, and 8 parts of furfurol dissolved in 150 parts spirit added; the mixture acquired a deep-red colour, and on cooling became a mass of minute acicular crystals closely resembling in appearance the furfuralinine salt. It was purified by recrystallization from boiling alcohol, dried in vacuo, and analyzed. I. 232 grm. substance gave 562 grm. carbonic anhydride and ⚫135 grm. water. Theory. I. C19 H23 H11 = 23 01 = 32 9.24 Furfurtoluidine nitrate.-This was prepared in a manner similar to the hydrochlorate, substituting the equivalent proportion of toluidine nitrate: 14 parts toluidine nitrate and 9 parts toluidine were dissolved in 100 parts hot alcohol, and 8 parts furfurol in an equal quantity (100 parts) of spirit added; after standing some time the nitrate crystallized out in deep. purple needles. When purified and analyzed it gave the following I. 160 grm. substance gave 355 grm. carbonic anhydride and '098 grm. water. I. 60.52 6.81 Theory. C 19 H23 It has therefore the composition C, H2, N, NO,, H. Furfurtoluidine.-The salts of furfurtoluidine, when treated with ammonia solution, were decomposed in a manner similar to that already described under the head furfuraniline, but not quite so readily. The crude free furfurtoluidine, when digested with ether, dissolved, and on filtering the solution, distilling off the ether, and drying the residue in a vacuum over sulphuric acid, the base was obtained as a brown amorphous mass, which is brittle and easily reduced to powder. It is not as fusible as furfuraniline, and is far less readily decomposed. A carbon and hydrogen determination of the freshly prepared base, purified by ether and dried in vacuo, gave the following results :— I. 243 grm. substance gave 660 grm. carbonic anhydride and ∙159 grm. water. This corresponds pretty nearly with the formula C, H, O, N ̧. 2 s VOL. XVIII. Both furfuraniline and furfurtoluidine resemble rosaniline in giving beautifully coloured salts, whilst the bases are nearly colourless, or of a pale brown colour. Furfurnaphthylamine.-When an alcoholic solution of furfurol was added to a similar solution of naphthylamine it immediately became of a red colour, which is as fugitive as the one obtained from aniline, but much duller. Several attempts were made to prepare crystalline salts of this compound, but without success, only dark-coloured resinous substances being obtained. Several other typical bases were also tried, but without any results. These were quinidine, coniine, sparteine, and theine. It appears, therefore, from these experiments, that it is only the bases of the aromatic series which combine with furfurol to yield these peculiar-coloured salts in a crystalline state. I cannot conclude this paper without acknowledging the very efficient aid I have received from my assistant, Mr. Charles Edward Groves, in the preceding investigation. IX. "On Parasulphide of Phenyl and Parasulphobenzine." By JOHN STENHOUSE, LL.D., F.R.S., &c. Received May 27, 1870. When sulphide of phenyl, CHS, was passed several times in succession through an iron tube filled with nails and heated to low redness, a considerable amount of carbonaceous matter was deposited, and a portion of the sulphide was converted into an isomeric compound, which I propose to call Parasulphide of Phenyl. In order to obtain this substance from the dark-coloured distillate which collected in the receiver when sulphide of phenyl was submitted to the action of heat in the manner above described, it was transferred to a copper retort and distilled. The clear dark-yellow oil was then cooled for several hours in a freezing-mixture, when a considerable quantity of a white crystalline substance separated in nodules; this is freed from undecomposed sulphide of phenyl by thoroughly draining it on a vacuum filter. It can readily be purified by repeated crystallization from boiling alcohol, in which it is rather soluble. I. 197 grm. substance gave 557 grm. carbonic anhydride and ⚫092 grm. water. II. 166 grm. substance gave 473 grm. carbonic anhydride and '077 grm. water. III. 200 grm. substance gave 254 grm. barium sulphate. Parasulphide of phenyl crystallizes from alcohol in small white needles, which melt at 94° C., and can be distilled at a very high temperature. It is insoluble in water, but rather soluble in bisulphide of carbon, ether, and benzol. Parasulphobenzine.-When parasulphide of, phenyl was digested for several hours with dilute sulphuric acid and acid chromate of potassium, it was gradually converted into a new substance, having a much higher melting-point, so that the completion of the oxidation was readily observed by the entire disappearance of the fused parasulphide. The crude parasulphobenzine was then collected, well washed with water, and purified by two or three crystallizations out of boiling alcohol. I. 194 grm. substance gave 470 grm. carbonic anhydride and 075 grm. water. II. 347 grm. substance gave 843 grm. carbonic anhydride and 138 grm. water. 10 These carbon determinations correspond with the formula C1, H1, SO,; it has therefore the same percentage composition as the sulphobenzine obtained by the oxidation of sulphide of phenyl *. Parasulphobenzolene melts at 230° C., is soluble in boiling alcohol, from which it crystallizes on cooling in the form of long white shining needles. It is insoluble in water, soluble in benzol, ether, and carbon disulphide. It dissolves readily in warm sulphuric acid, forming a colourless solution, and does not blacken even when heated to the boiling-point of the acid. Water precipitates it unchanged. It is also soluble in hot strong nitric acid without change, and crystallizes out on cooling. * Proc. Roy. Soc. vol. xiv. p. 351. X. "On a Method of graphically representing the Dimensions and Proportions of the Teeth of Mammals." By GEORGE BUSK, F.R.S. Received May 20, 1870. Of all the hard parts of animals, the teeth, more especially for palæontological purposes, undoubtedly afford the most constant and the most generally available characters. Any plan, therefore, by which the study and ready comparison of these organs may be facilitated and simplified cannot fail to be of some use to the zoologist and palæontologist. Having myself found the method I am about to describe convenient in many instances, more particularly in the case of fossil mammals, I have been led to believe, by the representations of several to whom it has been communicated, that it might be found useful by others, and consequently, though at first sight but a trifling matter, worthy of a place in the 'Proceedings of the Society. The characters afforded by the teeth are derived from their number, proportions (absolute and relative), and pattern. In many cases the pattern of the teeth must undoubtedly be taken into account; but in a very great number it will be found that the number and proportions, more particularly of the premolars and molars, are sufficient for the purpose of diagnosis, or, at any rate, that a knowledge of these particulars alone will reduce the necessity for further comparison within a small compass. A good illustration of this is afforded in the smaller Felidæ, in which, owing to their high specialization, the pattern of the teeth is in the main so very closely alike as to render it of very little assistance in diagnosis, though not altogether. The statement of the particulars above mentioned, in words or figures when numerous comparisons are needed, is tedious and laborious to both writer and reader; and even in the most carefully arranged tables it is difficult without close attention to perceive at once differences which though minute are, from their constancy, important and in fact necessary for the diagnosis of nearly allied forms. My plan may be termed one for the graphic or diagrammatic representation of the absolute and relative or proportional dimensions and number of the premolar and molar teeth, or of those constituting the molar series, and which have appeared to me in most cases sufficient for the purpose in view. But of course the incisors and canines might be included in the scheme if thought requisite. The method in which these "odontograms" are prepared will be at once obvious on inspection of the accompanying examples. Each horizontal line in the figures, which represent the maxillary and mandibular molar series of a species, corresponds to a single tooth, whose extreme length or antero-posterior diameter is indicated by the extent of the lighter shade, and its extreme breadth or transverse diameter by the darker shade. Both dimensions are, of course, measured from the same base-line. |