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Proceedings Chemical Society View Article Online / Journal Homepage / Table of Contents for this issue Issued 22/11 /1900 PROCEEDINGS OF THE CHEMICAL SOCIETY. EDITED BY THE XECRETARIEX. Vol. 16. No. 228. November 15th, 1900. Professor THORPE,C.B., F.R.S., President, in the Chair. Messrs. F. C. Britten, G. C. Thomson, R. G. Halstead, and J. A. Msthews were formally admitted Fellows of the Society. The following certificates were read for the first time :-Messrs. H. H. Cousins, Government Laboratories, Kingston, Jamaica ; Robert Dodd, 28, Sibella Road, Clapham, S.W. ; Arthur Houldershaw, 71, Published on 01 January 1900. Downloaded by Temple University 28/10/2014 14:04:48. Lavender Gardens, Vest Jesmond, Newcastle-on-Tyne ; Edward Hughes, Rectory, Barmouth ; Robert Salmon Hutton, Owens College, Manchester ; Stephen Archigenes Ionides, Balliol College, Oxford ; Robert Henry Jones, Glen Albyn, Coity Road, Bridgend, Glam. ; H. T. G. van der Linde, 101, Tyndall Avenue, Toronto, Canada; William Meredith, 63, Albion Place, Ulverston ; James Moir, The Ash, 62, Hamilton Place, Aberdeen, Scotland; H. M. Smith, 79, Helix Road, Brixton, S.W. Of the following papers, those marked * were read :- "147. id Trichlorobenzoic acid." By Francis Edward Matthews, The hexachloride of benzonitrile is acted upon by alcoholic sodium hydroxide, forming a mixture of trichlorobenzoic acids, which, on frac- tional crystallisation of the barium salts, was found to give it new trichlorobenzoic acid. View Article Online 188 At present foizr of the six possible trichlorobenzoic acids are known, the missing two being CO,H CO,H Cl/\ and Cl/)Cl. Cd,) Cd,) c1 c11 \/ As the new acid was found to yield an ester readily when treated with hydrogen chloride and alcohol, which an acid having the second of the above formulae should not do, both positions adjacent to the carboxyl group being occupied by chlorine, the former of the two formule may be taken as proved. By the action of quinoline upon the nitrile, C,H,Cl,* CN, followed by steam distillation, the nitrile of the new acid, C,H,Cl,*CN, is easily prepared in a state of purity. It crystallises from aqueous alcohol in long, white, lustrous needles melting at 57'. After hydrolysis with alcoholic sodium hydroxide, the acid, which crystallises from water in small needles melting at 163', is readily obtained. The following salts have been prepared : (C,H,Cl,CO,),Ba + 3H,O ; (C,H2C1,*C02),Sr + 3H20; (C6H,CI,* cO2),ca + 4H,O ; C,H,C1,*C02Ag. The acid chloride, C,H,CI,*COCl, melts at 36'; the amide, C,H,Cl,* CONH,, crystallises in small needles which melt at 204-205'. The ethyl ester, C,;H,CI,* CO,Et, is obtained by the action of hydrogen chloride and alcohol upon the acid. It is a liquid volatile with steam and possessing, but in a lesser degree, the odour of ethyl benzoate. * 148. '' Oxidation of benzalthiosemicarbazone." By Cleorge Young Ph.D., and William Eyre, B.Sc. Published on 01 January 1900. Downloaded by Temple University 28/10/2014 14:04:48. Benzal thiosemicarbazone, C,H,*CH: N*N:C( SH) NH,, is oxidised by ferric chloride to amido~?~enyZt~~iocliaxole,C,H,.C<~~,>C*NH,. The base melts at 222--223', its hydrochloride at 213-214'. The methyl derivative, C,H,*C,N,S*CH,:NH, is an oil ; its platini- chloride, [CQHQN,S],H2PtCl,, melts at 2 18'. The acetyl derivative, C6H,*C,N2SNH*COCH,, which melts at 276', is an acid forming stable sodium and silver salts. Both the methyl and acetyl derivatives yield the same methylacetyl derivative, C6H5*C2N2SCH3:N*COCH3, which melts at 144'. Benzal-4-rnethylthiosemicarbazone,C,H,*CH:N*N:C(SH)*NH*CH,, NN is similarly oxidised to CBH,.C~S-~C*NH.CH,,met?LyZcmido- phenyZthiodiuxoZe, which melts at 183-1 54'. Its platinichloride, [CQH,N,S]2H2PtCI,, melts at 208-209'. The acetyl derivative, C,H,C2N2S*N<~~(,,,, melts at 195". View Article Online 189 Benzal-4-phenylthiosemicarbazone, C,H,*C1H: N*N :C( 5 H) NH*C,H,, yields phenylamidophenylthiodiazole, C,H,* C<TiT>C NH*C,H,, pre- viously described by Marckwald. Its silver derivative, C,,H,oN,SAg, decomposes with explosive violence when suddenly heated. "149. The nitration of benzeneazosalicylic acid." By J. T. Hewitt and J. J. Fox. One of the authors has already pointed out (Hewitt, Trans., 1900, 77, 99) that when dilute nitric acid is warmed with benzeneazophenol a substance results in which the nitro-group has entered the phenol nucleus in the ortho-position relatively to the hydroxyl. Noelting, on the other hand, by nitrating benzeneazophenol in strong sulphuric acid obtained paranitrobenzeneazophenol (Ber., 1887, 20, 2997). The authors have studied the action of nitric acid on benzeneazo- salicylic acid under varying conditions and find that with dilute acid at 65-70" the nitro-group enters the salicylic acid residue in the ortho-position relatively to the hydroxyl. The constitution of the resulting compound was determined by comparison w.~ithe product obtained from phenyldiazonium chloride and nitrosalicylic acid (CO,H:OH:NO,=l :2:3). Benxeneuxoortl~onit~osalicylicacid melts at 197' (uncorr.), its methyl ester at 132-134' and the ethyl ester at 128-129'. By the nitration of benzeneazosalicylic acid dissolved in con- centrated sulphuric acid paranitrobenzeneazosalioylic acid, identical with the substance described by Meldola (l'runs., 1885, 4'7,666), was Published on 01 January 1900. Downloaded by Temple University 28/10/2014 14:04:48. obtained. Its ethyl ester melts at 220-225'. "150. I' Upon the collection and examination of the gases produced by bacteria from certain media." By Walter C. C. Pakes and Walter H. Jollyman. The authors described a new apparatus for the collection of the gases produced by bacteria when grown either under aerobic or anaerobic conditions. Experimenting with the Bacillus pyocyuneus, which is supposed to be a strictly aerobic organism, they found that it grew in media con- taining 1 per cent. of potassium or ammonium nitrate under the strictest anaerobic conditions as the term is at present understood (that is, in the presence of hydrogen, or in the absence of any gas). They concluded, therefore, that the terms aerobic and anaerobic must be extended to include the presence of oxygen in the form of nitrates. View Article Online 190 Upon analysing the gases produced by this organism from media containing nitrates, they found that both free oxygen and free nitro- gen were evolved, the former in small quantities but constantly. 151. “The bases contained in Scottish shale oil.” By Frederic Charles Garrett, M.Sc., and John Armstrong Smythe, B.Sc., Ph.D. Though many investigators have examined the bases contained in coal tar, but little attention has been paid to those present in shale oil, the authors have therefore undertaken the examination of those obtained from the Broxburn oil. The shale, on distillation, yields gas, ammonia water and (( crude oil ” ; this crude oil ” is again distilled, giving green naphtha,” ‘( green oil ” and ‘(still coke,” the temperature towards the end of the operation rising to a red heat. A quantity of this “ green naphtha ” was washed with 4 per cent. of sulphuric acid (diluted to about 15 per cent.), Steam was blown through the reddish- brown liquid so obtained €or several hours to free it from a small quantity (about 0.1 per cent.) of an oily liquid possessing a peculiarly disgusting smell ; when this had been removed sodium hydroxide solution (174 per cent.) was added and superheated steam blown through until all the volatile bases had been driven over. The soluble bases in the distillate were thrown out by the addition of solid sodium hydroxide, the mixed bases were then dried by solid potash and fractionally distilled ; each litre of the crude acid liquor yields about 120 grams of the dry bases, of which about 25 per cent. boil below 170°, and 46 per cent. between 170” and 205’. Published on 01 January 1900. Downloaded by Temple University 28/10/2014 14:04:48. The basic oil thus obtained was then repeatedly refractionated, and an attempt made to isolate the various bases in the lower frac- tions by precipitation with mercuric chloride and fractional crystallisa- tion of the salts so obtained. The portion boiling below 125” (about 10 grams) was examined for pyridine by precipitation with potassium ferrocyanide but none mas found, the base being chiefly a-picoline (b. p. 128”); from the other fractions below 160°, the symmetrical collidine (aya’-trimethyl pyridine) and two other bases which appear to be the hitherto undeacribed lutidines (up- and ap’-dimethyl pyr- idine). The first of these boils at about 160”and yields a platinichloride melting with decomposition at 20S0, whilst the second boils at about 140’, and although no platinum compound was isolated it yielded a gold compound melting at 73‘; in each case, however, the amount of base obtained was very small. Having now obtained between two and three kilograms of the raw bases, the authors are attempting a more systematic examination of them. The authors have to thank Ah. George Beilby for calling their View Article Online 191 attention to the necessity for this work, and Mr. D. R. Steuart for kindly providing them with the raw material they required. 152. “On a simplified method for the spectrographic analysis of minerals.” By Walter Noel Hartley, F.R.S., and Hugh Ramage, A.R.C. Sc. I. The authors pointed out that some of the rare earths are very difficult to detect and others more widely diffused are not easily separated and recognised either by the ordinary methods of chemical analysis or by spectroscopic examination. A simplification of the method of obtaining oxyhydrogen blow-pipe spectra (Hartley, Phil.
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