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finely powdered alloy of lead and sodium (containing 8 per cent. of sodium) with 500 grams of bromobenzene and 20 c.c. of ethyl acetat for 60 hours. The liquid portion of the product is poured off, the residue extracted with hot benzene; the solutions are then mixed, and the excess of bromobenzene and benzene distilled off in a vacuum. The residue is first recrystallised from benzene in presence of animal charcoal, and then several times from warm ether. It forms small, colourless needles which melt at 224-225°, and decompose at 270°. Sp. gr. 1.5298 at 20°. It is very sparingly soluble in alcohol, ether, and glacial acetic acid, more soluble in benzene, chloroform, and carbon bisulphide. It burns in air with a smoky flame. When heated with hydrochloric acid at 230°, lead chloride and chlorobenzene are formed.

Lead diphenyl dinitrate, PbPh2(NO3)2 + 3H2O, is readily obtained by gradually adding lead tetraphenyl to boiling nitric acid (sp. gr. 14). The acid must be kept at its boiling point. It separates on cooling in small, lustrous plates, and is recrystallised from water made acid with nitric acid. It is rather readily soluble in water and in alcohol. It detonates when heated below its melting point. When boiled with water, the liquid remains turbid owing to the formation of a basic salt, OH⚫PbPh2 NO3; this is a white powder.

Lead diphenyl diiodide, PbPh2l, is formed when a solution of iodine in chloroform is added to lead tetraphenyl also dissolved in chloroform. It separates in gold-coloured plates which melt at 101— 103°. It is soluble in chloroform, benzene, and alcohol. The corresponding bromide is a white powder which decomposes before fusing. Lead tetraparatolyl, Pb(C,H,), is prepared similarly to the phenyl compound from 120 grams of parabromotoluene, 300 grams of alloy, 40 grams of toluene, and 4 c.c. of ethyl acetate. The heating is continued for 50 hours. It is crystallised successively from benzene and alcohol. It forms small, colourless needles which melt at 239-240°, and decompose at 254°; sp. gr. +14329 at 20°. It is more readily soluble than the phenyl compound in benzene, carbon bisulphide, and chloroform. N. H. M.

Sulphuric Acid as an Iodine-carrier. By G. S. NEUMANN (Ber., 20, 581-582).-When equimolecular proportions of iodobenzene and sulphuric acid are heated at 100° for some hours, a mixture of paradiiodobenzene, iodobenzenesulphonic acid and benzenesulphonic acid is obtained. Ortho- and para-iodotoluene under like conditions yield diiodotoluene and triiodotoluene; whilst ortho- and para-iodophenol yield diiodophenol when treated with sulphuric acid in the cold.

W. P. W.

Tribromophenol. By A. PURGOTTI (Gazzetta, 16, 526-531).— The calcium-derivative of tribromophenol crystallises in white, silky needles; the ammonium-derivative forms minute crystals, more soluble in cold water than in hot; the silver-derivative is a red, insoluble powder darkening rapidly on exposure; the lead- and zinc-derivatives are white precipitates, and the copper-derivative a violet powder, insoluble in water, soluble in ammonia. The ethyl-derivative crystallises in bril

liant prisms melting at 69°. As an antiseptic, tribromophenol seems to be superior to phenol and thymol. V. H. V.

Manufacture of Resorcinol. By O. MÜHLHÄUSER (Dingl. polyt. J., 263, 154-157).-This substance is prepared on a large scale by fusing sodium benzenedisulphonate with sodium hydroxide. Its production from benzene involves the following operations :-(1.) Preparation of benzenesulphonic acid by treating pure benzene free from thiophen with sulphuric acid of 67° B. (2.) Conversion of the monosulphonic acid into benzenedisulphonic acid by heating with an excess of sulphuric acid at 240° for about 12 hours with constant agitation. (3.) Production of sodium benzenedisulphonate by boiling the mass out with water, liming until neutral, filter-pressing, and treating the filtrate with sodium carbonate. The mixture is again filtered, and the effluent liquid evaporated to dryness. (4.) Fusing the dried salt with soda in an open cast-iron boiler fitted with agitators. (5.) Dissolving the heated mass in water, and adding hydrochloric acid to feebly acid reaction. (6.) Extracting the resorcinol from the acid solution with amyl alcohol in an extraction apparatus. (7.) Subjecting the extract to distillation to expel the alcohol; the residue containing the resorcinol being dried in enamelled iron pans. (8.) Purification of the resorcinol by fractional distillation in a vacuum. According to this method 125 kilos. of sodium benzenedisulphonate yield from 20 to 23 kilos. of pure resorcinol. D. B.

Constitution of Dinitroquinol and Formation of Nitranilic Acid. By R. NIETZKI and J. PREUSSER (Ber., 20, 797-799).—The authors find that the diacetyldiamidoquinone, C,H2O2(NHAc)2, lately described by them (Abstr., 1886, 1024), is identical with the compound obtained by Bamberger (Abstr., 1884, 309) by the oxidation of triacetyltriamidophenol, to which he gave the formula C2H20N,Og. The simpler formula is undoubtedly the correct one, as when reduced with stannous chloride and hydrochloric acid the acetyl-groups are eliminated and diamidoquinol is formed. The compound liquefies at 265-270° without showing a definite melting point. The formation of quinol proves that the quinone-oxygens must as usual be in the para-position to one another, and the formation from triacetyltriamidophenol (prepared from picric acid), that the two amido-groups (and consequently the corresponding nitro-groups in the parent dinitroquinol) are both in ortho-positions to one of the oxygen-atoms or hydroxyl-groups respectively.

Nietzki has shown that this dinitroquinol is easily converted by nitric acid into nitranilic acid in which the two nitro-gronps are in the para-position to each other. This and also the formation of paradinitrodihydroxyquinone from the same quinol, leave little doubt of the intermediate formation of a tetranitroquinol. L. T. T.

Action of Sodium Alkoxides on Benzaldehyde. By L. CLAISEN (Ber., 20, 646—650).-When 12 grams of sodium and 150 grams of methyl alcohol are heated on a water-bath and treated with 106 grams of benzaldehyde, the whole soon solidifies to a mass of

white crystals. The product consists of benzoic acid (56 grams) and benzyl alcohol (45 grams). If the mixture, after being heated for some hours on a water-bath, is first treated with glacial acetic acid (30 grams) and then with water, the product contains only a trace of benzoic acid, and consists chiefly of benzyl benzoate boiling at 323324°. This boiling point was confirmed by preparing the salt by another method. Methyl benzoate and benzyl alcohol are also formed.

When benzyl benzoate and sodium methoxide are heated on a water-bath, a mixture of benzyl alcohol and methyl benzoate are formed; the same products are obtained when methyl benzoate and a solution of sodium in benzyl alcohol are warmed together.

Benzyl benzoate is also obtained by dissolving 15 gram of sodium in benzyl alcohol, adding 200 grams of benzaldehyde and heating for some days on a water-bath. 10 grams of glacial acetic acid and then water are added, and the oil distilled. The yield of benzyl benzoate is 150 grams. N. H. M.

Quinonedioxime and Dinitrosobenzene. By R. NIETZKI and F. KEHRMANN (Ber., 20, 613-616).-Quinonedioxime, C&H1(NOH), [14], is obtained when 2 parts of hydroxylamine hydrochloride and part of hydrochloric acid are added to 1 part of quinol dissolved in the least possible quantity of cold water, and the whole allowed to remain for 12 hours. It crystallises in slender, colourless needles, decomposes at 240°, and is soluble in ether and hot water; the aqueous solution, however, undergoes partial decomposition. With dilute ammonia, it gives a greenish-yellow solution from which hydrochloric acid effects only a partial precipitation, the resulting solution yielding nitrosophenol when shaken with ether. When reduced with stannous chloride and hydrochloric acid, paraphenylenediamine is obtained.

Paradinitrosobenzene is formed by the oxidation. of quinonedioxime in alkaline solution with potassium ferricyanide. It is a goldenyellow powder, insoluble in all neutral solvents, sublimes partially without decomposition, and is slightly volatile with steam. When boiled with a solution of hydroxylamine hydrochloride, it is reconverted into quinonedioxime. W. P. W.

Introduction of Acid Radicles into Ketones. By L. CLAISEN (Ber., 20, 655-657).-Benzoylacetophenone is obtained by mixing sodium ethoxide (free from alcohol) with ethyl benzoate and acetophenone; the whole solidifies with development of heat to a crystalline mass. This is washed several times with water, then with dilute soda solution, and is then treated with carbonic anhydride. The yield is 50 per cent. of the acetophenone employed. In a similar manner, ethyl benzoylacetate can be prepared from acetophenone and ethyl carbonate, but the yield is less satisfactory than in the case of benzoylacetophenone.

Nitrosoacetophenone, CHBz: N-OH, is readily prepared by adding acetophenone and then amyl nitrite to a well cooled solution of sodium in 20 parts of alcohol, and keeping the whole in a well closed

vessel for 12 to 24 hours at a low temperature. The reddish-brown sodium salt is freed from the liquid portion of the product by suction, washed with ether, dissolved in water and treated with acetic acid. It crystallises in prisms melting at 126-127°; the solution in sulphuric acid acquires an intense yellowish-red colour when treated with phenol. It dissolves in solutions of alkalis and alkaline carbonates, and is precipitated from the solutions slowly and incompletely by carbonic anhydride. When heated alone or with sulphuric acid, it is decomposed into benzoic and hydrocyanic acids.

The condensation products of ketones with aldehydes (Claisen and Schmidt, Ber., 14, 1459) are readily prepared by means of sodium alkoxides. Benzalacetophenone is obtained by mixing 12 grams of acetophenone with 10.5 grams of benzaldehyde, adding 3 c.c. of a 20 per cent. sodium methoxide solution, and keeping the whole for some days at a winter temperature. The yield is 90 per cent. of the theoretical. N. H. M.

Separation of Ortho- and Para-toluidine. By A. WÜLFING (Dingl. polyt J., 263, 260).—On treating a mixture of para- and orthotoluidine with nitrous acid, the latter is first attacked and converted into an amidoazo-compound, after which the acid acts on the paracompound, forming a diazoamido-derivative. Hence by employing an amount of acid equivalent to the proportion of orthotoluidine, the para-compound remains unaltered. It is recommended to effect the conversion by treating toluidine hydrochloride with sodium nitrite. This process is of special utility in separating the paratoluidine contained in crude toluidine. D. B.

Manufacture of Dimethylaniline. By O. MÜHLHÄUSER (Dingl. polyt. J., 263, 348–351).—For the production of methylaniline on a commercial scale, two processes are in vogue: (1) Treating aniline with common hydrochloric acid of 21° B. and methyl alcohol, and heating the mixture under pressure; (2) Allowing methyl alcohol to act on aniline sulphate under pressure. After the completion of the reaction, the mass is rendered alkaline with lime, and distilled with steam. The oily distillate is then treated with dried salt to remove the last traces of water. The methylaniline so obtained may be used for the preparation of "violets," whilst for the manufacture of methylene-blue and malachite-green from dimethylaniline, it is necessary to subject the oil to fractional distillation, collecting the portion which comes over between 200° and 205°. D. B.

Conversion of Phenols into Amines. By V. MERZ and P. MÜLLER (Ber., 20, 544-550).-Continuing their experiments (this vol., p. 243), the authors have examined the action of mixtures of ammonium zinc bromide and ammonium bromide, and of ammonium zinc chloride and ammonium chloride on the three isomeric cresols when heated in sealed tubes for 40 hours at temperatures varying between 300° and 340°. The results are given in quantitative form, and show that under these conditions orthocresol yields about 10 per cent. of orthotoluidine and 50 per cent. of orthoditolylamine; meta

cresol yields about 27 per cent. of metatoluidine and 50 per cent. of metaditolylamine; and paracresol yields from 25 to 45 per cent. of paratoluidine and 40 to 30 per cent. of paraditolylamine; the remainder in each case consisting of unaltered cresol, and from 2 to 6 per cent. of carbonaceous residue.

The boiling point of paraditolylamine was found to be 320-321°. W. P. W. Condensation Products of Ethyleneaniline with Aldehydes. By F. Moos (Ber., 20, 732-734).-Hofmann's diethyleneaniline (diphenylpiperazine if named according to Merz and Mason's proposals, this vol., p. 498), C2H: (NPh)2: C2H1, is a very stable compound, and this stability is probably due to its hexatomic ring formation. The author has obtained analogous compounds of the general formula C2H, (NPh), CHR, containing a pentatomic ring, by the condensation of ethyleneaniline with aldehydes.

Benzaldehyde and ethyleneaniline when heated together unite, with separation of water, to form a compound, C2H (NPh)2CHPh, which crystallises in colourless needles, melts at 137°, and distils without decomposition. Cumaldehyde and ethyleneaniline, under like conditions, yield a compound, C4H6N2, crystallising in long, white, silky needles, melting at 124-125°, and soluble in ether and absolute alcohol. Salicylaldehyde and ethyleneaniline give a compound crystallising in groups of white, silky needles. It melts at 116°, and is easily soluble in ether and absolute alcohol, less so in benzene. Anisaldehyde and ethyleneaniline form a compound crystallising in colourless prisms, soluble in benzene and alcohol; it melts at 164°, and has the composition C2H2N2O. Isobutaldehyde and ethyleneaniline undergo a similar reaction, yielding a compound, CH2N2. This crystallises in large, colourless needles, melts at 95°, and is easily soluble in benzene and ether, sparingly so in water. Enanthaldehyde and ethyleneaniline yield the compound C2HN2, which crystallises in glistening needles, melts at 79°, and is easily soluble in ether, but sparingly so in benzene.

All these compounds, when warmed with dilute hydrochloric or sulphuric acid, are very readily reconverted into their constituents, thus differing from diphenylpiperazine. The author is now investigating the analogous compounds (containing a hexatomic ring) formed by the condensation of aldehydes with trimethyleneaniline.

L. T. T.

Action of Carbonyl Chloride on Ethylene- and Trimethylene-diphenyldiamine. By A. HANSSEN (Ber., 20, 781-785).— Trimethylenediphenyldiamine, C3H.(NHPh)2, was prepared by heating a mixture of aniline (4 mols.) and trimethylene bromide (1 mol.) on the water-bath. It is an oil which boils with decomposition above 360°. Its sulphate crystallises in minute needles melting at 155-156°, and is soluble in alcohol. With sodium nitrite the sulphate yields the corresponding dinitrosamine crystallising in greenish scales melting at 87°. When a solution of the diamine in benzene was slowly added to a well-cooled solution of carbonyl chloride in NPh•CH, benzene, trimethylenediphenylcarbamide, CO NPh CHCH2, and tri

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