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mercial product, since Hesse remarks that he only obtained this new substance from the chrysarobin occurring in commerce in the years 1905 and 1906.

With regard to emodinanthranol (Hesse's "emodinol "), no doubt can be entertained that this was derived chiefly from the monomethyl ether of dehydroemodinanthranol (see Note) which was isolated and described by the present authors, since the material examined by Hesse had been heated with hydriodic acid. Hesse himself shows that he could not obtain "chrysophanol methyl ether and "emodinol methyl ether" in a state of purity, and the evidence he adduces does not seem to justify the conclusion that they are present. In the material examined by the present authors, the former compound certainly did not occur, but proof of the presence of small amounts of the latter was obtained.

It has now been shown that aceto-m-4-xylidide readily yields 2: 5-dimethylindole by this method. The reaction, however, was found not to be generally applicable since 2:4 xylylsuccinamic acid, C6H3Me2 NH CO CH2 CH2 CO2H, and its derivatives, which were of interest in connection with the problem of the constitution of physostigmine, could not be converted into indoles without disruption of the molecule.

The reduction products of 3-nitro-p-tolylacrylic acid (I.) have also been described. It has been ascertained that the nitro-group of this substance is more readily attacked by reducing agents than the cinnamyl residue, so that the first product of the reaction is 3-amino-p-tolylacrylic acid (II.), which by further reduction is converted into 8-3amino p-tolylpropionic acid (III.):—

The statement made by Hesse that chrysophanolanthranol (Hesse's "chrysophanol ") is insoluble in alkalis Me in the absence of air is incorrect. This substance dissolves fairly readily in 10 per cent aqueous potassium hydroxide, yielding a bright yellow solution, which, on the admission of air, develops the deep red colour due to the formation of chrysophanol.

(NOTE. In a footnote to his paper, added after the completion of the work, Hesse states that he has never observed the occurrence of the monomethyl ether of dehydroemodinanthranol described by the present authors, but this is obviously due to his having worked almost entirely with material which had been demethylated by means of hydriodic or hydrochloric acid. In all the commercial samples of chrysarobin examined by the present authors it was present to the extent of from 13'4 to 411 per cent).

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282. "Mechanism of the Decomposition of Carbamide and Biuret by Heat, and of the Formation of Ammelide." By EMIL ALPHONSE WERNER.

In continuation of work recently published (Trans., 1913, ciii., 1010), a quantitative study of the decomposi tion of carbamide and biuret by heat has been made, the results of which have thrown new light on the mechanism of the progressive changes.

of heat on carbamide is a reversible reaction in accordance It was shown that the formation of biuret by the action with the equation :—

HN:COH
NH2

135-150°

+HN:CO

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CH
I.

The replacement of the labile hydrogen atom by an ethyl group destroys this tautomerism, and the ethyl ether can accordingly be isolated in two distinct forms.

2-Methyldihydroresorcin can be prepared from cresorcinol by reduction, but the product so obtained is impure, and it was only isolated in the form of crystalline derivatives.

281. "Researches on the Constitution of Physostigmine. Part III. The Formation of Substituted Indoles from m-4Xylidine, and the Reduction of 3-Nitro-p-tolylacrylic Acid." By ARTHUR HENRY SALWAY.

In this investigation the author has described some experiments, which were conducted with the object of ascertaining whether Madelung's reaction for the preparation of substituted indoles from o-toluidides (Ber., 1912, xlv., 1128, 3541) could be applied to acyl derivatives of m-4-xylidine, according to the scheme :

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By heating pure anhydrous biuret for five minutes at 192° (m. p. 190°), as much as 30 per cent of regenerated carbamide was extracted from the residue. The general idea that biuret decomposes directly into ammonia and cyanuric acid is therefore erroneous.

No evidence could be obtained of the formation of tricyanocarbamide, C3N3(NH CO NH2)3, described by Hantzsch and F. Hofmann (Ber., 1905, xxxviii., 1010) as perties of the substance described by them are identical a product of the action of heat on carbamide; the pro

with those of ammelide (cyanuric monamide), which has
been long since recognised by Liebig and Wöhler and
others as a product of the decomposition of carbamide.
Proof was obtained that this compound originates from the
further interaction of cyanic acid and biuret according to
the equation:-
.CONH,

CONH, >C:NH or

HN cONH,*HN:CO = HN CO NH

HN CONC•NH2+H2O,

and hence is also formed during the decomposition of biuret, but in smaller quantity, since the conditions are less favourable. Thus it was shown that the whole cycle of changes which take place during the decomposition of carbamide and biuret by heat can be simply explained by

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283. "Note on the Mechanism of a Bromination in Ketones." BY ARTHUR LAPWORTH.

H. Leuchs bas recently found that, by bromination of an optically active ketonic acid, a monobromo-derivative is obtained which exhibits some optical activity. As the activity of both compounds is dependent on enantio morphism in the arrangement of the atoms and groups itself, Leuchs concludes that the enolic form of the ketone could not have been an intermediate stage in the substitution process, and he suggests applying a similar test to active monalkylmalonic hydrogen esters (Ber., 1913, xlvi., 4238).

around the a-carbon atom to which the bromine attaches

Leuchs's inference is not quite conclusive, for the facts admit of different interpretations; for example, if the ketonic acid, like other carboxylic acids, is to any extent associated, and substitution takes place in one part of a poly. molecule only, then the remainder of the polymolecule may retain its enantiomorphous arrangement during enolisation of the first portion, and consequently the formation of a new "asymmetric" carbon atom in the latter would naturally lead to the formation of some excess, however small, of atoms of one sign. In other words, a "partial asymmetric synthesis " is possible.

The bromination of active a-methylbutyric acid has previously been studied by Schütz and Marckwald (Ber., 1896, xxix., 59), and of B-phenylisobutyric acid by Lapworth and Lenton (Proc., 1902, xviii., 35). In both instances the product was inactive.

284. "Studies in the Diphenyl Series. Part V. Derivatives and Substitution Products of the Two Isomeric o-Dinitrobenzidines and Synthesis of Derivatives of Benzery threne." By JOHN CANNELL CAIN, ALBERT COULTHARD, and FRANCES MARY GORE MICKLETHWAIT.

The authors have prepared a number of acyl and azoderivatives of the two isomeric o-dinitrobenzidines (Trans., 1912, ci., 2298), and have submitted the two bases to the diazo-reaction.

3:3-Dinitrobenzidine gives the corresponding disubstituted 3: 3-dinitrodiphenyl, but 3: 5'-dinitrobenzidine, in those cases where copper is employed, gives derivatives of benzerythrene :

Of the numerous derivatives of the two bases that have been prepared, no two corresponding ones are identical.

285. "Harmine and Harmaline. Part II. The Synthesis of iso-Harman." BY WILLIAM HENRY PERKIN, jun., and ROBERT ROBINSON.

A detailed description of work of which a preliminary account has already appeared (Proc., 1912, xxviii., 154).

NOTICES OF BOOKS.

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Researches on Irritability of Plants. By JAGADIS CHUNDER BOSE, M.A., D.Sc., C.S.I. London, New York, Bombay, and Calcutta: Longmans, Green, and Co.

1913.

THE experiments described in this book are exceedingly interesting, and the author appears to have arrived at results of vital importance in biochemistry. He has devised and perfected two pieces of apparatus which he calls the Resonant and Oscillating Recorder respectively, by means of which the amplitude and period and also the absolute rate of movement of the plant during any phase of autonomous response to stimulation can be determined with perfect accuracy. He has found it possible to record time-intervals which do not exceed one-thousandth of a second in length. The so-called sensitive plants were chosen for study, and mechanical, chemical, thermal, and electrical methods of stimulations were included. The general result of the experiments is the revelation of a remarkable similarity of response in the plant and the

animal.

Practical Sanitation. By GEORGE REID, M.D., D.Ph.

Seventeenth Edition. London: Charles Griffin and
Co., Ltd. 1913.

edition of this book was published, progress in sanitation ALTHOUGH it is only eighteen months since the sixteenth has been so rapid that in the eighteenth edition a good many alterations and additions have been found necessary. The book gives a thoroughly practical outline of the plumbers, medical officers of health, and householders elements of sanitation, and inspectors, builders, and will find it full of valuable information. The appendix on English sanitary law will serve as a useful guide to the reading of candidates for examinations on the subject. The Application of Physico-chemical Theory to Technical Processes and Manufacturing Methods. By Prof. Dr. R. KREMANN. Translated from the German by HAROLD E. POTTS, M.Sc. (Liverpool), and Edited by ALBERT MOND, Ph.D. London: Constable and Co., Ltd. 1913. THE value of a knowledge of physical chemistry to the enlightened technical chemist who is anxious to keep abreast of the times and to shake himself free from the bondage of rule-of-thumb methods is fully recognised on all sides, and in spite of the difficulty of the subject it is most necessary that the student should get an early acquaintance with it, so that when he approaches more advanced work in his own special branch he should be able to do so from the physico chemical standpoint. This book gives a useful introduction to the subject. The chapters are graduated in difficulty, and a minimum amount of mathematics is introduced. Many industries are adequately dealt with, and the phase rule is particularly clearly explained and illustrated. The translation has been carefully done and the book is well printed; the only error which a careful examination has brought to light being in the lettering of the diagram of a gas-engine, where the illustration does not agree with the text. Industrial Research in America. Presidential Address. By ARTHUR D. LITTLE. Reprinted from the Journal of Industrial and Engineering Chemistry. 1913. THIS Presidential Address, delivered before the American Chemical Society, gives a very stimulating account of the state of industrial research in America, and contains some remarkable facts and figures concerning the development of certain industries and the solution of some technical problems by American chemists. The research work done by the ten great scientific bureaus organised and controlled by the Department of Agriculture has led to results of great value, some of which are briefly summarised in the address, and short accounts are also given of the pioneer work in industrial research which is being

done by some of the Universities and technical schools. | are frequently open to criticism as to whether an analyst The words of the President regarding the applications of could do them in the time allowed, even in one's own chemical science to the industries in the future are so laboratory. The large percentage of failures show there generally applicable that they are well worth quoting :- must be something wrong. "We shall need for years to prosecute a vigorous cam. paign for a better understanding by the general public of what chemistry is and what research is. The popular imagination is ready to accept any marvel which claims the laboratory as its birthplace, but the man in the works still disbelieves that two and two in chemical nomenclature make four. We need multiplication of research laboratories in special industries, each with an adequate staff of the best men obtainable and an equipment which gives full range to their abilities."

Die Chemische Verwandtshaft. ("Chemical Affinity"). By Dr. MAX SPETER. Leipzig: Philipp Reclam, jun. 1913. (80 Pf.).

THIS booklet deals with the connection between chemical
affinity and thermic, electric, and radiant energy, and gives
a short summary of the experimental data which have been
collected and the general laws which have been deduced
from them. The author does not put before his readers
many speculations as to the nature of the force which
brings about the combination of substances, but confines
himself to the statement of the positive results which have
been obtained, and considering the very small size of the
book he does so with great completeness and clearness.

Whitaker's Almanac for 1914. Half Bound, 904 pages.
J. Whitaker and Sons.

A LIST of some thirty-five new features are given as having
been introduced in this issue, enough to show that the
publishers are fully determined to maintain the reputation
of the almanac. Among the items we note the Home
Rule Bill, Royal Flying Corps, Labour Unrest, Aero-
nautics, National Health Insurance Amendment Act,
Wireless Telegraphy, and other current topics. "Whitaker's
Almanac" is too well known to require further intro-
duction: we need only say that it is as good as ever.
Whitaker's Peerage, Baronetage, Knightage, and Cham-
pionage for 1914.

DURING the past year Honours appear to have been distributed somewhat more sparingly than of late, and the Obituary list is ominously long. A great deal of interesting and useful information is given in the way of footnotes, in addition to the official matter. Amongst other things we note that much of the fable and superstition connected with the Coronation Stone, so well known to all visitors to the Abbey, has been cleared away by Sir Archibald Geikie, who, speaking as a geologist, declares that the stone was almost certainly quarried in the sandstone district between Argyll and the Forth. An interesting account is given of the ceremony of the Coronation of the present King, together with many quaint observances not generally known.

CORRESPONDENCE.

INSTITUTE OF CHEMISTRY CONFERENCE.

To the Editor of the Chemical News. SIR,-As one who has criticised the ways of the Institute of Chemistry, I am glad to see that there is a decided opinion among teachers of chemistry that this Society might be improved.

I would suggest that it would be in its best interests to abolish the practical examinations altogether. To suggest that any examiners can tell whether a man is a competent chemist by working in a strange laboratory for six hours or so a day for three or four days, under conditions that are never found in practice, seems to me a very unscientific way of finding out a man's capabilities. The exercises set

As an alternative to practical examinations, suppose the Institute insisted upon a two years course of general chemistry in a college, or a three years course at evening classes, and then made each student analyse correctly a series of salts the composition of which was known only to a small examining committee. The diploma not to be given until the series were correctly analysed. This might take two or four or more years, either at a day college or evening classes. I do not mean the same series for every

student.

I am sorry to see the attitude taken up by some gentlemen, that class distinctions have anything to do with abilities. There are chemists in this country who have had to make the best use they could of the limited opportunities for learning which they could afford, and whose opinion would now be taken in preference to a F.I.C. in cases of dispute, but if any of these gentlemen applied under the terms of the Charter for election to the Fellowship they would probably be told that "their qualifications are not such as would justify the Council in admitting them to the F.I.C.," and probably, without any disrespect, not one of the Council would be equal to them scientifically in their special branches.-I am, &c., ERNEST A. LEWIS.

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Comptes Rendus Hebdomadaires des Séances des l'Académie des Sciences. Vol. clvii., No. 19, November 10, 1913.

Origin of Cyclic Bases of Coal-tar.-L. C. Maillard. -The cyclic bases of tars undoubtedly derive their nitrogen from ancient protein material, and according to the author's view the intermediate products are nitrated humic matter resulting from the condensation of the sugars (constituents of cellulose, &c.) with amino-acids (constituents of proteins). The formation of volatile bases at the expense of the humic matter is due to pyrogenation, but it is certain that the union of the amino-nitrogen with the carbon chain of the sugars occurs before pyrogenation.

Decomposition of Halogen Alkylates of Hexamethylene-tetramine. Marcel Sommelet. Boiling water is capable of decomposing the halogen alkylates of hexamethylene-tetramine, particularly those which are derived from benzyl chloride and analogous compounds. The somewhat unexpected result is the formation of the aldehyde of the halogen derivative. The chlorobenzylate is so sensitive to the action of water that benzoic aldehyde is obtained by simply heating its solution in aqueous alcohol. The bromotoluylates of hexamethylene-tetramine are similarly transformed into toluic aldehydes.

MEETINGS FOR THE WEEK.

MONDAY, 5th.-Society of Chemical Industry, 8.

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'Viscosity of Oils," by J. L. Strevens. "Oxygen Content of Gases from Roasting Pyrites," by Lewis T. Wright. "Electrical Conductivity of Milk during its Concentration, with suggestions for a Practical Method of Determining the End-point in the Manufacture of Sweetened Condensed Milk," by L. C. Jackson, Leslie McNab, and A. C. H. Rothera. "Monazite from some New Localities," by S J. Johnstone. Royal Institution, 3. (Christmas Lectures, TUESDAY, 6th. adapted to a juvenile auditory). "A Voyage in THURSDAY, 8th. Space," by Prof. H. H. Turrer, D.Sc., F.R.S., WEDNESDAY, 7th.-Royal Society of Arts, 5. (Juvenile Lecture. Electric Vibrations and Wireless Telegraphy)" by R. P. Howgrave-Graham, M.I.E.E.

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General Statement of Valency from the Periodic point | Electricity as a Conditioning Agent (i.) in the Proof view.

Some suggested Cross Relations between Extreme
Valency Values.

The Valencies of Zinc, Cadmium, and Mercury.

A Periodic Classification of the Elements based upon Geometrical Regularities, and the idea of Branches at certain Places.

cesses Operative in certain Chemical Changes, and (ii) in certain Primary Forms of Matter. The Study of some special Groups or Classifications of the Elements in Compounds.

A Note on the Valencies of Vanadium and Bismuth. A few statements of the Theory of the Atom based upon Experiments in Molecular Physics.

With Tables and Diagrams.

Post free from any Bookseller, 2s. 8d.

"The author has evidently carefully studied the literature of the theories of valency, and he shows much skill in stating briefly the gist of an argument and ingenuity in pointing out the directions in which fruitful research may possibly be undertaken."- Chemical News, October 3, 1913.

London: SIMPKIN, MARSHALL, HAMILTON, KENT, and CO., Ltd.,
Stationers' Hall Court, E.C.

NOW READY.

iii

GENERAL INDEX TO THE CHEMICAL NEWS,

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"The Index under review is one that will be necessary to every reader of the Chemical News, and, indeed, will be useful to all chemists, giving, as it does, references to so many subjects, such as university intelligence, &c., which are found in perhaps no other chemical journal."-Nature, June 19, 1913.

"A great service has been now performed for the active chemist in making this mass of material easily accessible through a general index. It is evident that no pains have been spared to make this work as complete and All those interested, particularly in chemistry and chemical industry, will be grateful to the management of the Chemical News for bringing to completion this great work."-American Journal of Science, July, 1913.

accurate as possible.

"The Index seems very complete, and forms an interesting survey of he period covered by it. It should be of great value to chemists who possess files of the Chemical News "Journal of the Franklin Institute, July, 1913.

"It is not merely a compilation of all the volume indexes, but is much more elaborate. Every possessor of a set of the Chemical News, whether complete or partial, will do well to add this most valuable volume to his library.”— Journal of the American Chemical Society, August, 1913.

"Although the Index contains two thousand one hundred and thirty-six columns, the book is of a convenient size, and is only an inch and five-eighths thick. All chemists should show their appreciation of the enterprise of the Chemical News by adding this valuable Index to their library."-Knowledge, November, 1913.

"This Index covers all material in the issues of the Chemical News for the first fifty years, and should be of inestimable value to every working chemist, whether a subscriber to the Chemical News or not."―Journal of Indus rial and Engineering Chemistry, November, 1913.

"The value of the Index is obvious Cons derable pains have been taken to render it a trustworthy source of reference, and the plan has been adopted of including in it both subjects and authors. This has rendered it a somewhat large volume, but the method facilitates reference, for it sometimes happens that the name of the author escapes memory, or the subject connected with his name may be forgotten. Since the references go back so far, the Index enables the reader to trace the development in many cases of industrial science, analytical processes, and so forth."-The Lancet, November 22, 1913.

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