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WATTS'

DICTIONARY OF CHEMISTRY



VOL. IV.



WATTS*



DICTIONARY OF CHEMISTRY-



REVISED AND ENTIRELY REWRITTEN



BY

M. M. PATTISON MUIE, M.A.

FELLOW, AND PRELECTOR IN CHEMISTRY, OF GONVILLE AND CAIUS COLLEGE, CAMBRIDGE

AND

H. FOESTEE MOELEY, M.A., D.Sc.

FELLOW OF UNIVERSITY COLLEGE, LONDON, AND LECTURER ON PHYSICS AND .
CHEMISTRY AT CHARING CROSS HOSPITAL MEDICAL SCHOOL



ASSISTED BY EMINENT CONTRIBUTORS

IN FOUE VOLUMES
VOL. IV.



WITH ADDENDA



OF THE

UNIVERSITY



LONDON
LONGMANS, GEEEN, AND CO.

AND NEW YOBK: 15 EAST 16 th STEEET
1894

All rights reserved



'W4
, l v,V




INTRODUCTION

TO THE AETICLES ON INOEGANIC CHEMISTET.



IT has been thought advisable to include in an ADDENDA brief accounts of
the chief work done in descriptive inorganic chemistry since the publication of
Vols. L, II., and III., and the printing^the final proofs of Vol. IV.

Nothing bearing on organic chemistry has been included hi the ADDENDA,
as to give an account of what has been done in this department since the various
volumes were published would occupy many hundred pages.

Dates are attached to the references made to original memoirs in the
ADDENDA ; and references are frequently made to abstracts of the memoirs in
the Journal of the Chemical Society.

M. M. PATTISON Muni.



INTRODUCTION
TO THE ARTICLES EELATING TO OEGANIC CHEMISTEY.



THE names used to denote ring formulas are given below for convenience of
reference.

Since the publication of the last volume I have been assisted in the work of reading
and making abstracts of original memoirs by Drs. T. Cooksey, T. A. Lawson, Samuel
Eideal, Messrs. J. Wilkie, G. N. Huntly, and J. T. Norman. I have also been assisted
by Mr. Arthur G. Green and Mr. Cecil W. Cunnington in the work of revising the
proof-sheets. I have great pleasure in thanking these gentlemen for the energetic and
efficient manner in which they have carried out their share of the work.

H. FOESTEE MOELEY.

Nomenclature of Sing Formulae.

Hydrocarbons.
Trimethylene.

Tetramethylene.



Pentametfienyl hydride.



Pyrrole.
Pyrazole.

NH <CH';CH Giy"M-

Metapyrazole.

Triazole
Osotriazole.
Tetrazole.
Pyrrodiazole.



Nitrogen compounds.

, ^-N=l



!:N



or



KTT/ N== ?

NH <CH:N




>N



Indazine.

Pseudo-indazine.
14^ JT /v>6 ja -4 Acridine.
I 4 <^ ^ ]>C 6 H 4 Phenazine.




Naphthoros-
induline.



^CH:CH
\CH:CH



INTRODUCTION.

Oxygen compounds.



Vll



<*""<*



Iso-oxazole or Isoxazple.



Coumarone.
Indoxazine.



Carbizine.



<ci;cH> NH

JH.NHv



^NH.CH



Sulphur compounds.



=
S <CH:CH



Thiophthene.



U -n- /Nx p,g- f Methenyl-amido-phenyl-mer-



CH:CH



Thiazole.






Pyroximidine.



'Phenoxazine or PTien-
azoxine.



Oiazthiole. Thiobiazole.



Piazthiole.
Imido-di-phenyl-sulphide.




INITIALS OF SPECIAL CONTRIBUTORS.



I A.



J. W. C.



G. G.



W. D. H.



SVANTE AEEHENIUS, Ph.D., Professor of Chemistry in Stockholm. Contributes
SOLUTIONS I.

J. W. CAPSTICK, D.Sc., M.A., Fellow of Trinity College, and Demonstrator in
Physics in the University, Cambridge. Contributes CAPILLAKITY, METHODS BASED
ON ; and VISCOSITY OF LIQUIDS.

GEOEGE GLADSTONE, Esq. Contributes OPTICAL METHODS, section Befraction and
Dispersion.

W. D. HALLIBUETON, M.D., F.E.S., Professor of Physiology at King's College,
London. Contributes PROTEIDS.



W. N. H. W. N. HAETLEY, F.E.S., Professor of Chemistry in the Royal College of Science,
Dublin. Contributes OPTICAL METHODS, section Spectroscopic methods.

E. A. L. E. A. LETTS, Ph.D., Professor of Chemistry at Queen's College, Belfast. Contributes
PHOSPHINES.

E. M. RAPHAEL MELDOLA, F.E.S., Professor of Chemistry in the Finsbury Technical
College. Contributes PHOTOGRAPHIC CHEMISTRY.

W. O. WILHELM OSTWALD, Ph.D., Professor of Chemistry in the University of Leipzig.
Contributes ELECTRICAL METHODS.

C. O'S. COENELIUS O'SULLIVAN, F.E.S., Burton-on-Trent. Contributes STARCH and

SUGABS.

S. U. P. SPENCER PICKEEING, M.A., F.E.S. Contributes SOLUTIONS II.
S. R. SAMUEL EIDEAL, D.Sc. Contributes TANNIN.

W. A. T. WILLIAM A. TILDEN, D.Sc., F.R.S., Professor of Chemistry at the Royal College
of Science, South Kensington. Contributes TERPENES.

T. E. T. T. E. THOEPE, D.Sc., Ph.D., F.E.S., Head of the Government Laboratories, Somerset
House. Contributes SPECIFIC VOLUMES.

Articles by Mr. MUIE are initialed M. M. P. M.

UNSIGNED ARTICLES are by Dr. MOELEY, except those in the Addenda, which are by
Mr. MUIE.




ABBREVIATIONS



I. JOURNALS AND BOOKS.

When an author has been mentioned in an article, he is usually referred to thereafter
in that article by his initial only.

A. . . Liebig's Annalen der Chemie.

A. A.. . Annales de la Sociedad Cientifica Argentina.

A. Ch. . Annales de Chimie et de Physique.

P. Am. A. Proceedings of the American Academy of Arts and Sciences.

Am. . . American Chemical Journal.

Ann. M. . Annales des Mines.

Am. S. . American Journal of Science.

A.C.J.. Journal of the American Chemical Society.

Am. Ch. American Chemist.

Am. J. American Journal of Pharmacy.

Pharm.

An. . . The Analyst.

A. Ph. S. Proceedings of the American Philosophical Society.
Ar. N. . Archives n6erlandaises The Hague.

Acad. . Mdmoires de l'Acad6mie des Sciences.

Ar. Ph. . Archiv der Pharmacie.

Ar. Sc. . Archives des Sciences phys. et nat.

B. . . . Berichte der deutschen chemischen Gesellschaft.

B. A. . Eeports of the British Association.

Bl. . . Bulletin de la Societe chimique de Paris.

B. B. . Berliner Akademie-Berichte.

B. C. . Biedermann's Centralblatt fur Agricultur-Chemie.

B. J. . . Berzelius' Jahresberichte.

B. M. . Berliner Monatsberichte.

C.S. Mem. Memoirs of the Chemical Society of London.

C.J.. . Journal of the Chemical Society of London.

C.J.Proc. Proceedings of the Chemical Society of London.

C. N. . Chemical News.

C. B. . Comptes-rendus hebdomadaires des Stances de 1'Acade'mie des Sciences
Paris.

C. C. . . Chemisches Central-Blatt.

D. P. J. Dingler's polytechniscb.es Journal.

Fr. . Fresenius' Zeitschrift fur analytische Chemie.

G. . . Gazzetta chimica italiana.

G. A. . Gilbert's Annalen der Physik und Chemie.

H. . Hoppe-Seyler's Zeitschrift fur physiologische Chemie.

L . . Proceedings of the Eoyal Irish Academy.

J. . . Jahresbericht iiber die Fortschritte der Chemie und verwandter Theile

anderer Wissenschaften.

J. C. T. . Jahresbericht fiir Chemische Technologic.

J. M. . Jahrbuch fiir Mineralogie.

J. de Ph. Journal de Physique et des Sciences accessoires.

J. Ph. . Journal de Pharmacie et de Chimie.

J. pr. . Journal fiir praktische Chemie.

J. Tin. . Jahresbericht iiber Thierchemie.

J. R. . . Journal of the Eussian Chemical Society.

J. Z. . . Jenaische Zeitschrift fiir Medicin und Naturwissenschaft.

L. V. . Landwirthschaftliche Versuchs-Stationen.

M. . . Monatshefte fiir Chemie und verwandte Theile anderer Wissenschaften.

M. S. . Le Moniteur Scientifique.

Mem. S. Memoires de la Societe d'Arcueil.

$A.

Mem. B. M6moires couronnes par 1'Acade'mie de Bruxelles.



ABBREVIATIONS.



N. . .
N.Ed.P.J.
N. J. P.
N. R. P.
N, J. T. .
N. Z. R.
P.M. .
P.. . .
P. B. . .
Pf.
Pr.E. .
Ph. . .
Ph. C. .
Pr. . .
P. R. I. .
P.Z. .
R. T. C. .
R.P. .
Q. J. S. .
S.. . .
Scher. J.
S. C. I. .
Sitz.W. .
T. or Tr.
T.E.. .
W. . .
W.J. .

z. . .

Zeit.ang.

Ch.

Z.B. .
Z.f.d.g.

Natur-

wiss.
Z.K.. .
Z. P. C.
Z. V.. .

Bn.

E.P. .
G.P. .
Gm. . .
Gm.-K. .
Gerh. .
JL. . .
G. 0. .
Stas,

Rech.
Stas,
Nouv. R,
Th.



Nature.

New Edinburgh Philosophical Journal.

Neuer Jahresbericht der Pharmacie.

Neues Eepertorium fiir die Pharmacie.

Neues Journal von Trommsdorff.

Neue Zeitschrift fur Eiibenzuckerindustrie.

Philosophical Magazine.

PoggendorfTs Annalen der Physik und Chemie.

Beiblatter zu den Annalen der Physik und Chemie.

Pfliiger's Archiv fiir Physiologic.

Proceedings of the Koyal Society of Edinburgh.

Pharmaceutical Journal and Transactions.

Pharmaceutisches Central-Blatt.

Proceedings of the Koyal Society.

Proceedings of the Eoyal Institution of Great Britain.

Pharmaceutische Zeitschrift fiir Eussland.

Eecueil des travaux chimiques des Pays-Bas.

Eepertorium fiir die Pharmacie.

Quarterly Journal of Science.

Schweigger's Journal der Physik.

Scherer's Journal der Chemie.

Journal of the Society of Chemical Industry.

Sitzungsberichte der K. Akademie zu Wien.

Transactions of the Eoyal Society.

Transactions of the Eoyal Society of Edinburgh.

Wiedemann's Annalen der Physik und Chemie.

Wagner's Jahresbericht.

Zeitschrift fiir Chemie.

Zeitschrift fiir angewandte Chemie.

Zeitschrift fiir Biologic.

Zeitschrift fiir die gesammten Naturwissenschaften.



Zeitschrift fiir Krystallographie und Mineralogie.

Zeitschrift fiir physikalische Chemie.

Zeitschrift des Vereins fiir die Eiibenzuckerindustrie des deutschen

Eeiches.

Handbuch der organischen Chemie : von F. Beilstein, 2te Auflage.
English Patent.
German Patent.

Gmelin's Handbook of Chemistry English Edition.
Gmelin-Kraut : Handbuch der anorganischen Chemie.
Traite de Chimie organique : par Charles Gerhardt.
Lehrbuch der organischen Chemie : von Aug. Kekul6.
Graham-Otto : Lehrbuch der anorganischen Chemie [5th Ed.]
Stas' Eecherches, &c. ~1

sAronstein's German translation is re-
Stas' Nouvelles Eecherches, &c. J f erred to as Chem. Proport.

Thomson's Thermochemische Untersuchungen.



Aq . .
aq . .
A' . "I
A" .
A'" . J
B'B"&c.



cone,
dil.

g.
mgm.
mm.
mol.



II. TERMS AND QUANTITIES, &c., FREQUENTLY USED.

Water ; e.g. NaOHAq means an aqueous solution of caustic soda.

18 parts by weight of water.

Eesidues of mono-, di-, and tri-basic acids. Thus, in describing the salts

of a monobasic acid NaA', CaA' 2 , A1A' 3 may be written, HA' standing

for the acid. For a dibasic acid we should write Na 2 A", CaA", A1 2 A" 3 &c.
Stand for bases of the ammonia type, in describing their salts. Thus the

hydrochloride would be B'HCl or B''2HC1, according as the base is

monacid or diacid, &c.
Concentrated.
Dilute,
gram,
milligram,
millimetre,
molecule;



ABBREVIATIONS.



XI



oil. . .

pp. . .

to ppt. .

PPg-

ppd. . .

sol. . .

insol. . .
v. e. sol. .
v. sol.

m. sol. .

si. sol. .
v. si. sol.

v. . . .

c/.. . .

c. . . .



At. w. .
Mol.w.or

M. w.
D. . . .
cor. . .
uncor. .

V.f). .* '.

S.G. . .

S.G. 1 ,? .

S.G. .



S.H. .
S.H.v.
S.H.p.
H.C. .



H.C.V.

H.C.p.
H.F.



H.F.v. .

H.F.p. .
H.V. .



T.C.

S.V.



s.v.s. .

E.G. . .

C.E. (10

to 20)

S. . . .
S. (alco-
hol)



BOO



liquid, nearly, or quite, insoluble in water,
precipitate,
to precipitate,
precipitating,
precipitated,
soluble in.
insoluble in.
very easily
very

moderately
slightly-
very slightly
see.

compare,
about.

a melting-point,
a boiling-point.
Hardness (of minerals)
Atomic weight.
Molecular weight.



soluble in.




uncorrected.

in vapour.

vapour-density, i.e. density of a gas compared with hydrogen or air.

Specific gravity compared with water.

at 10 compared with water at 0.

15 ,, 4.

12 ; compared with water of which the temperature is
not given.
Specific heat.
. ,, ,, of a gas at constant volume.

pressure.

Quantity of heat, in gram-units, produced during the complete com-
bustion of the mass of a solid or liquid body represented by its

formula, taken in grams.
Heat of combustion in gram-units of a gram-molecule of an element or

compound, when gaseous, under constant volume.
The same, under constant pressure.
Quantity of heat, in gram-units, produced during the formation of the

mass of a solid or liquid body represented by its formula, taken in

grams, from the masses of its constituent elements expressed by

their formulae, taken in grams.
Heat of formation of a gram-molecule of a gaseous compound from the

gram-molecules of its elements under constant volume.
The same, under constant pressure.
Heat of vaporisation of a liquid, i.e. gram-units of heat required to change

a gram-molecule of the liquid compound at B.P. into gas at same

temperature and pressure.
Thermal conductivity (unit to be stated).
Specific volume ; or the molecular weight of a gaseous compound divided

by the S.G. of the liquid compound at its boiling-point compared with

water at 4.
Specific volume of a solid ; or the mass of the solid expressed by its

formula, taken in grams, divided by its S.G.
Electrical conductivity (the unit is stated in each case).
Coeffioient of expansion (between 10 and 20).

|" of a gas = volume dissolved by 1 volume of water.

Solubility in water I of a liquid or solid = number of grms. dissolved by
alcohol j 100 grms. of water. In both cases the temperature

l_is stated.
Index of refraction for hydrogen line .

sodium D, &o.

Molecular refraction for sodium light, i.e. index of refraction for line D
minus one, multiplied by molecular weight, and divided by S.G. at 15
compared with water at 0.

The same ; S.G. being determined at 15-20 and referred to water at 4.
The same for line of infinite wave-length, index being determined by
Cauchy's formula (Briihl's B A ).



Xll



ABBREVIATIONS.



[o] D
[a],



Specific rotation for sodium light.
neutral tint,



-x
d



a = observed rotation for



100mm. of liquid. d=S.G. of liquid, p = no. of grammes of active
substance in 100 grammes of liquid.

M. M. Molecular magnetic rotatory power = ^ x g / x m / where m = molecular

weight of the body of S.G. = d, a angle of rotation under magnetic

influence, a! = angle of rotation of water under same influence, and

m' = molecular weight of water (18).
Ac . Acetyl C 2 H 3 0.

Bz . Benzoyl C 7 H 5 0.

Cy . Cyanogen ON.

Et . Ethyl C-ft. ^

Me . Methyl CH 3 .

Ph . PhenylC 6 H 5 . \ in formulas.

Pr . Normal Propyl CH 2 . CH 2 . CH 3 .

Isopropyl CH(CH 3 ) 2 . /

E, R' &c Alcohol radicles or alkyls.
prim . primary.
sec . secondary.

t&rt . tertiary.

n . . normal.
m, o, p meta ortho para.
c . . consecutive.
i . . irregular.

symmetrical.

u . . unsymmetrical.
pseudo.

attached to nitrogen.
Employed to denote that the substituent is attached to a carbon atom

which is next, next but one, or next but two, respectively, to the

terminal carbon atom. The end to be reckoned from is determined

by the nature of the compound. Thus CH 3 .CHBr.C0 2 H is o-bromo-

propionic acid.
denotes that the element or radicle which follows it is attached to a ter-

minal carbon atom.
o,)8,7,&c. indicate position in an open chain, only.
1,2,3, &c. indicate position in a ring only.

(o), (j8), Used when a, , &c. are employed in a sense different from the above,
&c. e.g. (o)-di-bromo-camphor.

Baeyer's Nomenclature :
(B.) . . benzene ring.

(Py.) . . pyridine ring.

Thus (JB. 1:3) dichloroquinoline, means a meta-dichloroquinoline in

which the chlorine atoms are both in the benzene ring.

While (Py. 1:3) dichloroquinoline, means a similar body, only the

chlorine atoms are in the pyridine ring. The numbers are counted

from two carbon atoms which are in different rings, but both united

to the same carbon atom.
(A.) . . denotes the central ring in the molecule of anthracene, acridines, and

azines.

eso- . . means that the element or radicle it precedes is in a closed ring.
exo- . . ,, ,, ,, not in a benzene ring.

allo- . . denotes isomerism that is not indicated by ordinary formulae ; thus maleiic

acid may be called aZZo-fumaric acid.
thio- . . denotes displacement of oxygen by sulphur.
sulpho- . the group S0 3 H, except in the word sulphocyanide.

sulphydro- the group SH.

Tribromonitrobenzene sulphonic acid [1:2:3:4:5] means that the three

bromines occupy positions 1, 2, and 3 ; the nitro- group the position 4,

and the sulpho- group the position 5.

x Denotes that the formula to which it is affixed has not been determined by
analysis. But it by no means follows that formulae without this mark are those of
analysed compounds.

All temperatures are given in degrees Centigrade unless when specially stated
otherwise.

Wave-lengths are given in 10' 7 mm.

Formulae, when used instead of names of substances, have a qualitative meaning
only.

Thomsen's notation is used in thermochemical data.



UNIVER SITT



DICTIONARY OF CHEMISTRY.



PHENYL-AZOXAZOLE



. [30].



Formed by the action of C0 2 on an alkaline
solution of the oxim of phenyl-glyoxal (Kussa-
noff, B. 24, 3503). Needles, insol. water.

PHENYL - BENZAMIDINE C 13 H I2 N 2 i.e.
C 6 H 5 C(NH).NHPh or C 6 H 5 .C(NPh).NH 2 [112].
Formed from benzonitrile and aniline hydro-
chloride at 230 (Bernthsen, A. 184, 348 ; 192,
33). Formed also from benzimido-ether and
aniline, and from CPhChNPh and NH 3 (Kobbert,
4.265,138). Nodules (from alcohol), si. sol.
water. Forms a crystalline nitrate.

Reactions. 1. Split up by heat into aniline
and benzonitrile. 2. Dry H 2 S at 130 forms
C 6 H 5 .CS.NHPh and some thio-benzamide.
3. CS 2 at 100 forms thio-benzanilide and phenyl-
benzamidine sulphocyanide. 4. Eeduced by
sodium-amalgam to C 6 H 5 .CH(NH,).NHPh.
5. Nitrous acid forms benzanilid'e (Mieran,

A. 265, 141).

The derivatives C 6 H.C(N.S0 Ph).NHPh
[139] and C 6 H 8 (S0 2 N:C(NHPh).C 6 H 5 ) s [196]
have been prepared (Wallach, A. 214, 214;
Jackson, Am. 9, 346).

s - Di - phenyl - benzamidine Ci 9 H 16 N 2 i.e.
C 6 H 5 .C(NPh).NHPh. [144].

Formation. 1. From benzanilide by treat-
ment with PC1 5 and aniline (Gerhardt, A. 108,
219 ; Hofmann, Z. 1866, 161 ; Wallach, A. 184,
83). 2. From Ph.CCL, and aniline with or with-
out ZnCL, (Limpricht, A. 135, 82 ; Dobner,

B. 15, 233). 3. A product of the action of
aniline hydrochloride at 250 on benzonitrile,
thiobenzamide, or phenyl-benzamidine (Bernth-
sen, A. 184, 352). 4. By heating benzanilide
with phenyl cyanate at 190 (Kuhn, B. 18,
1476). 5. By heating the hydrochloride of
benzimido-ether in alcohol with aniline for a
long time (Kobbert, A. 265, 155).

Properties. Needles (from alcohol), m. sol.
benzene. Its alcoholic solution is neutral to
litmus. Not affected by nitrous acid. Split up
into aniline and benzanilide when boiled for a
long time with alcohol.

Reactions. I. Dry H 2 S at 160 forms thio-
benzanilide. 2. CS, at 140 forms PhCS.NHPh
and NPhCS (Bernthsen, A. 192, 34). 3. Cone.
HClAq at 150 yields aniline and benzoic acid.

Salts. B'HCl, v. si. sol. water .
B'C 6 H 3 N 3 7 : yellow needles.

w-Di-phenyl-benzamidine
C 6 H 5 .C(NH).NPh 2 . [112]. Formed by heating
diphenylamine hydrochloride with benzonitrile
at 180 for 5 days (Bernthsen, A. 192, 5).
Trimetric tablets, v. sol. alcohol and benzene.

VOL. IV.



Its alcoholic solution turns litmus blue. Cone.
H 2 S0 4 gives a violet-blue colour on warming.

Reactions. 1. Dilute HClAq at 180 forms
NPh^z. 2. The free base and its hydro-
chloride yield benzonitrile and diphenylamine
on heating. B. Nitrous acid forms NPh.JBz
(Klobbert, A. 265, 157). 4. H 2 S at 130 forms
Ph.CS.NH 2 , diphenylamine, PhCS.NPh 2 , and
NH 3 . 5. CS 2 at 140 forms PhCS.NPh 2 and
HNCS.

Salts. B'HCl. [c. 223]. Monoclinic
crystals, a:b:c = -529:1: -507 ; = 8552'. V. soL
water, sol. alcohol, insol. ether. B'^H^tCL,
B'HNCS. [203]. Yellow prisms.

PHENYL-BENZAMIDOXIM
C 6 H 5 .C(NOH).NHPh. [136]. Formed by boil-
ing C 6 H..CS.NHPh with an alcoholic solution of
hydroxylamine (Miiller, B. 19, 1669). Needles
(from water). Yields B'HCl. ClC0 2 Et forms
C 14 H 10 N 2 2 [167].

DI-PHENYL-BENZAZIDINE C 19 H 18 N 4 i.e.
C 6 H 3 C(N.NHPh).NH.NHPh. [179]. Formed by
the action of phenyl-hydrazine on PhCCl 3 or
on the hydrochloride of benz-imido-ether dis-
solved in absolute alcohol (Pinner, B. 17, 182 ;
Marckwald, C. C. 1888, 1410). Dark-red needles.

PHENYL-BENZENE v. DIPHENYL.

p-Di-phenyl-benzene C 18 H 14 i.e. C 6 H 4 Ph 2 .
Mol. w. 230. [207]. (c. 405).

Formation. 1. A product of the action of
sodium on an ethereal solution of jp-di-bromo-
benzene, or, better, of a mixture of p-di-
bromo-benzene with bromine (Eiese, Z. [2]
6, 192, 735 ; A. 164, 168). 2. Together with its
isomeride, and other products, by passing the
vapour of benzene, or of a mixture of benzene
and toluene, through a red-hot tube (G. Schultz,

B. 6, 415; A. 174, 230; 203, 118; Carnelley,

C. J. 37, 712). 3. Together with the isomeride
and other products, by the action of A1C1 3 on a
mixture of MeCl and diphenyl (Adam, Bl. [2]
49, 97; A. Ch. [6] 15,241).

Properties. -Needles (from benzene), or iri-
descent laminae (by sublimation) ; insol. alcohol,
v. si. sol. HOAc. Its solution in benzene shows
blue fluorescence. Cone. H 2 S0 4 gives a dirty-
green solution changing to purple.- Cr0 3 in
HOAc oxidises it to diphenyl ^-carboxylic [216]
and terephthalic acids. Does not form a com-
pound with picric acid. Not volatile with steam.
Yields C 18 C1 U on exhaustive chlorination with
SbCl 5 (Merz a. Weith, B. 16, 2884).

References. BKOMo-and TRI-CHLORO- Di-

PHENYL-BENZENES.

Iso-di-phenyl-benzene C 18 H 14 . [85J. (c. 370).
Formed as above. Slender prisms, v. sol. al-

B



PHENYL-BENZENE.



cohol. Yields benzole acid on oxidation by
Cr0 3 .

s-Tri-phenyl-benzene C 24 H 1S i.e. C 6 H 3 Ph 3 .
Mol. w. 306. [171]. (above 360). Formed from
acetophenone by treatment with P 2 5 , with alco-
holic NH 3 , or with dry HC1 (Engler, B. 6, 638 ; 7,
1123). Formed also by heating C 6 H 3 (C S H 4 . GQfL} 3
with KOH (Gabriel a. Michael, B. 11,
1007). It is also a by-product in the action of
acetophenone on dimethylaniline in presence of
ZnCl, (Dobner a. Petschoff, A. 242, 336). Tri-
metric crystals ; a:b:c = -566:1: -766, si. sol. alcohol.
Yields benzoic acid on oxidation by Cr0 3 in
HOAc (Mellin, B. 23, 2533). By exhaustive
chlorination with SbCl s it yields per-chloro-tri-
phenyl-benzene (Merz a. Weith, B. 16, 2883).
On heating with I and red P at 275 it yields the
crystalline dodeca-hydride C^Hg,, and finally oily
C 24 H 38 (Mellin, B. 23, 2534). Fuming IL,S0 4 at
100 forms a disulphonic acid, which yields the
Ba salt C., 4 H 6 S 2 6 Ba crystallising in needles.

PHENYL-BENZENE-SULPHAZIDE v.

Phenyl-hydrazide of BENZENE SULPHONIC ACID.

DI-PHENYL-BENZENYL-DI-UREA
NHPh.CO.NH.CPh:N.CO.NHPh. [172].

Formed from benzamidine hydrochloride, phenyl
cyanate, and NaOHAq (Pinner, B. 22, 1607).
Needles, insol. water, v. si. sol. hot alcohol.

PHENYL-BENZIMIDO-ETHER C 15 H I5 NO i.e.
CPh(NPh).OEt. A product of the action of
aniline on benzimido-ether (Lossen, A. 265, 138).
Oil. Decomposed by cone. HClAq into EtCl and
benzanilide.

PHENYL BENZOATE v. Benzoyl derivative
of PHENOL.

PHENYL-BENZOIC ACID v. DIPHENYL-CARB-

OXYLIC ACID.

PHENYL-BENZOPHENONE C ]9 H 14 Oi.e. [1:4]
C 6 H 5 .C 6 H 4 .CO.C 6 H 5 . [104]. V.D.9'0. Formed by
oxidation of ^-benzyl-diphenyl with chromic
acid (Goldschmiedt, M. 2, 437 ; Koller, M. 12,
501). Formed also from diphenyl, BzCl, and
A1C1 3 (Wolf, B. 14, 2032). Scales, sol. alcohol.
Yields benzophenone-j0-carboxylic acid on further
oxidation by CrO s .

Oxim. [194]. Needles. When HC1 is
passed into its solution in HOAc containing
Ac 2 and the mixture heated in sealed tubes
at 100, it is converted into the isomeric
C 6 H 5 .C 6 H 4 .CO.NHC 6 H 5 [224]. The oxim is re-
duced by sodium-amalgam to the corresponding
amine C 6 H 5 .C 6 H 4 .CH(NH 2 ).C 6 H 5 [77].

Benzoyl derivative of the Oxim [193].
Needles (from alcohol).

Phenyl-hydrazide. [144]. Yellow
needles (from dilute alcohol).

Di - phenyl - benzophenone (C 6 H 3 .C 6 H 4 ) 2 CO.
[229]. Formed by the action of COCLj on
diphenyl in presence of A1C1 3 (Adam, Bl. [2] 47,
688 ; A. Ch. [6] 15, 259). Got also by oxidising
CH 2 (C 6 H 4 Ph) 2 (Weiler, B. 7, 1188). White needles,
sol. acetone, v. si. sol. alcohol. Not attacked by
fuming HN0 3 or by H 2 S0 4 and HN0 3 at 100.
By adding Na to its solution in alcohol-benzene
it is reduced to (C 6 H 5 .C 6 H 4 )oCH.OH, [151], S.
(ether) 5 ; S. (alcohol) 1-25 at 15. Potash-fusion
gives diphenyl-p-carboxylic acid [218].

PHENYL-BENZOPHENONE CARBOXYLIC
ACID C 6 H 4 Ph.CO.C 6 H 4 .C0 2 H. [220]. Formed
from diphenyl, phthalic anhydride, and A1C1 3
(Kaiser, .4. 257, 96). Needles. Yields an oxim



[140], a phenyl-hydrazide [194], and a methyl
ether Me A' [85-90].

PHENYL-BENZOYL is BENZOPHENONE.

PHENYL-BENZOYL-ACETIC ACID
CHBzPh.C0 2 H. Methyl ether MeA'. Formed
from de-oxybenzoin, NaOEt, and ClCO.,Me
(Kattner, B. 21, 1316). Oil, decomposed by dis-
tillation into CJE 2 Ph 2 , C0 2 , and HOBz.

PHENYL-BENZOYL-BUTYRIC ACID
CHBzPh.CH,.CH 2 .CO,H. (&)-Desyl-propionic
acid. [136]. Formed from deoxybenzoin,



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