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A DICTIONARY

OF



APPLIED CHEMISTRY



VOL. IV.



A DICTIONARY OF APPLIED CHEMISTRY

BY

SIR EDWARD THORPE, C.B., LL.D., F.R.S.

Assisted by Eminent Contributort

REVISED AND ENLARGED EDITION

5 Vols. Medium 8vo, 2 $s. net per volume.



LONGMANS, GREEN, AND CO.
LONDON, NEW YORK, BOMBAY, AND CALCUTTA



A DICTIONARY



OF



APPLIED CHEMISTRY



BY

SIR EDWARD THOEPE, C.B., LL.D., F.E.S.

EMERITUS PROFESSOR OF CHEMISTRY, IMPERIAL COLLF.GE OF SCIENCE AND TECHNOLOGY, SOUTH KENSINGTON,

LONDON ;

LATE PRINCIPAL OF THE GOVERNMENT LABORATORY, AND A PAST PRESIDENT OF THE
CHEMICAL SOCIETY AND OF THE SOCIETY OF CHEMICAL INDUSTRY



ASSISTED BY EMINENT CONTRIBUTORS



REVISED AND ENLARGED EDITION



IN FIVE VOLUMES



VOL. IV.



WITH



LONGMANS, GREEN, AND CO

39 PATEKNOSTER ROW, LONDON
NEW YORK, BOMBAY, AND CALCUTTA

1913



All rights reserved



ABBEEVIATIONS

OF THE TITLES OF JOURNALS AND BOOKS.



Amer. Chem. J.
Amer. J. Pharm. .
Amer. J. Sci. . .
Analyst ....
Annalen ....
Ann Chim. anal. .

Ann. Chim. Phys. .
Ann. Falsif. . . .
Ann. Inst. Pasteur.
Arch. PJiarm. . .
Bcntl. a. Trim. . .

Ber

Ber. Deut. pJiarm.

Ges

Bied. Zentr. . . .

Bio-Chcm. J. . .
Biochem. Zeitsch. .
Brewers J. . . .
Bull. Imp. Inst. .
Bull. Soc. chim. .
Chem. Ind. . . .
Cliem. News . . .
Chem. Soc. Proc. .
Chem. Soc. Trans.
Chem. Zeit. . . .
Chem. Zentr. . .
Compt. rend. . . .
Dingl. poly. J. . .
Farber-Zeit. . . .
Flilck. a. Hanb. .

Frdl

Gazz. chim. ital.
Jahrb. Min. . . .
J. Amer. Chem. Soc.
J. Ind. Eng. Chem.
J. Inst. Brewing .
J. Pharm. Chim. .
J. Phys. Chem. . .
J. pr. Chem. . . .
J. Russ. Phys. Chem.

Soc

J. Soc. Chem. Ind.
J. Soc. Dyers. . .
Min. Mag. . . .
Monatsh

Pharm. J. . . .
Pharm. Zeit. . .
Phil. Mag. . . .
Phil. Trans. . . .
Plwt. J. . . . .
Proc. Roy. Soc. . .
Rec. trav. chim.
Zeitsch. anal. Chem.
Zeitsch.angew. Chem.
Zeitsch. anorg. Chem.
Zeitsch. NaJir.

Genussm. . . .
Zeitsch. offentl.

Chem

Zeitsch. physikal.

Chem

Zeitsch. physiol.
Chem. ,



American Chemical Journal.

American Journal of Pharmacy.

American Journal of Science.

The Analyst.

Annalen der Chemie (Justus Liebig).

Annales de Chimie analytique applique'e a 1'Industrie, a 1' Agriculture,

a la Pharmacie et a la Biologic.
Annales de Chimie et de Physique.
Annales des Falsifications.
Annales de 1'Institut Pasteur.
Archiv der Pharmazie.
Bentley and Trimen. Medicinal Plants.
Berichte der Deutschen chemischen Gesellschaft.

Berichte der Deutschen pharmazeutischen Gesellschaft.
Biedermann's Zentralblatt fur Agrikulturchemie und rationellen

Landwirtschafts-Betrieb.
The Bio-Chemical Journal.
Biochemische Zeitschrift.
Brewers Journal.

Bulletin of the Imperial Institute.
Bulletin de la Societe chimique de France.
Chemische Industrie.
Chemical News.

Journal of the Chemical Society of London. Proceedings.
Journal of the Chemical Society of London. Transactions.
Chemiker Zeitung.
Chemisches Zentralblatt.

Comptes rendus hebdomadaires des Seances de PAcade'mie des Sciences.
Dingler's polytechnisches Journal.
Farber- Zeitung.

Fliickiger and Hanbury. Pharmacographia.
Friedlander's Fortschritte der Teerfarbenfabrikation.
Gazzetta chimica italiana.

Neues Jahrbuch flir Mineralogie, Geologic und Palaeontologie.
Journal of the American Chemical Society.
Journal of Industrial and Engineering Chemistry.
Journal of the Institute of Brewing.
Journal de Pharmacie et de Chimie.
Journal of Physical Chemistry.
Journal fur praktische Chemie.

Journal of the Physical and Chemical Society of Kussia.

Journal of the Society of Chemical Industry.

Journal of the Society of Dyers and Colourists.

Mineralogical Magazine and Journal of the Mineralogical Society.

Monatshefte fur Chemie und verwandte Theile anderer Wissen-

schaften.

Pharmaceutical Journal.
Pharmazeutische Zeitung.

Philosophical Magazine (The London, Edinburgh and Dublin).
Philosophical Transactions of the Koyal Society.
Photographic Journal.
Proceedings of the Royal Society.

Receuil des travaux chimiques des Pays-Bas et de la Belgique.
Zeitschrift fur analytische Chemie.
Zeitschrift fur angewandte Chemie.
Zeitschrift fur anorganische Chemie.

Zeitschrift fiir Untersuchung der Nahrungs-und Genussmittel.
Zeitschrift fiir offentliche Chemie.

Zeitschrift fiir physikalische Chemie, Stochiometrie und Verwandt-
schaftslehre.

Hoppe-Seyler's Zeitschrift fur physiologische Chemie.

266981



LIST OF CONTRIBUTORS

TO VOLUME IV.



Dr. E. F. ARMSTRONG (Messrs. Huntlcy and Palmers, Reading). [OXYDASES.]

Dr. HOWARD TURNER BARNES, M.A., M.Sc., F.R.S., Macdonald Professor of Physics
and Director of the Physics Building, McGill University, Montreal, Canada.
[PYROMETRST.]

EDWARD J. BEVAN, Esq., F.I.C., and W. BACON, Esq., London. [PAPER.]

W. H. BRAGG, Esq., M.A., F.R.S., Cavendish Professor of Physics in the University of
Leeds. [RADIOACTIVITY. Part II.]

WILLIAM BURTON, Esq., M.Sc., F.C.S., Pilkington Tile and Pottery Co., Manchester.
[POTTERY AND PORCELAIN.]

Dr. J. C. CAIN, Editor of the Journal of the Chemical Society, London. [PYRONINE
COLOURING MATTERS.]

E. G. CLAYTON, Esq., F.I.C., Analytical and Consulting Chemist, London. [PAINTS ;
PIGMENTS.]

Dr. J. B. COHEN, F.R.S., Professor of Organic Chemistry, University of Leeds. [RACEMISM.]

JAMES CONNAH, Esq., B.Sc., F.I.C., The Government Laboratory, Custom House,
London. [PARAGUAY TEA; RUM; SAKE.]

CECIL H. CRIBB, Esq., B.Sc., F.I.C., Analytical and Consulting Chemist, London.
[PEPPER ; CAYENNE PEPPER ; PIMENTO.]

W. P. DREAPER, Esq., F.I.C., Editor of the Chemical World, London. [ARTIFICIAL
SILK, LUSTRA CELLULOSE, OR CELLULO-SILK.]

CHARLES W. GAMBLE, Esq., M.Sc., Municipal Technical School, Manchester. [PHOTO-
MECHANICAL PROCESSES.]

Dr. ERNEST GOULDING, F.I.C., Imperial Institute, London. [SiLK.]

ARTHUR G. GREEN, Esq., M.Sc., F.I.C., Professor of Dyeing in the University of
Leeds. [PRIMULINE AND ITS DERIVATIVES.]

Dr. JOHN T. HEWITT, M.A., F.R.S., Professor of Chemistry in the East London College.

[QUINONES.]

GEORGE T. HOLLOWAY, Esq., A.R.C.S., F.I.C., Metallurgical Chemist, London.
[PLATINUM.]

HERBERT INGLE, Esq., B.Sc., F.I.C., late Chief Chemist to the Transvaal Agricultural
Department. [OKRA ; OLIVE ; ORANGE ; PARSNIP ; PAWPAW ; PEA ; PEA-NUT ; PEACH ;
PEAR ; PERSIMMON ; PINE APPLE ; PLUM ; POMEGRANATE ; POTATO ; PRICKLY COM-
FREY ; PRICKLY PEAR ; PUMPKIN ; RADISH ; RAPE ; RASPBERRY ; RED CURRANT ;
RHUBARB ; RICE ; SAGO ; SAINFOIN.]

MISS ZELDA KAHAN, B.Sc. [OSMIUM; PALLADIUM; RHODIUM; RUBIDIUM; RUTHENIUM.]

VIVIAN B. LEWES, Esq., F.I.C., Professor of Chemistry in the Eoyal Naval College,
Greenwich. [SMOKE AND SMOKE PREVENTION.]

Dr. JULIUS LEWKOWITSCH, M.A., F.I.C., Consulting and Analytical Chemist, London.
[OLIVE OIL ; PAINT OILS ; PALM KERNEL OIL ; PALM OIL ; PERILLA OIL ; POPPY
SEED OIL ; PORPOISE OIL ; RAPE OIL ; RAVISON OIL ; SAFFLOWER OIL ; SAPONIFICA-
TION ; SEAL OIL ; SESAME OIL ; SEWAGE FATS ; SOAP.]

T. B. LIGHTFOOT, Esq., London. [REFEIGERATING AND ICE-MAKING MACHINERY.]

Dr. GEORGE LUNGE, F.C.S., Emeritus Professor of Applied Chemistry, Zurich
Polytechnic. [POTASSIUM.]

Dr. W. MAKOWER, Victoria University, Manchester. [RADIOACTIVITY. Part I.]



viii LIST OF CONTRIBUTORS.

Dr. GILBERT T. MORGAN, A.R.C.S., F.I.C., Professor of Chemistry in the Faculty of
Applied Chemistry, Royal College of Science for Ireland, Dublin. [PRASEODYMIUM ;

QUINONEOXIME DYES J SAMAE1UM ; SCANDIUM.]

KENNETH S. MURRAY, Esq., British Oxygen Company, London. [INDUSTRIAL PRO-
DUCTION AND USES OF OXYGEN.]

G. S. NEWTH, Esq., F.I.C. [PYROTECHNY.]

Dr. THOMAS STEWART PATTERSON, The University, Glasgow. [POLARIMETRY.]

A. G. PERKIN, Esq., F.R.S., F.I.C., Clothworkers' Research Laboratory, University of
Leeds. [OLD FUSTIC ; ONION SKINS ; ORSELLINIC ACID ; PARSLEY ; PERSIAN BERRIES ;
PHCENIN AND PHCENICEIN ; POLYGONUM CUSPIDATUM ; POPLAR BUDS ; PRUNETIN ;
PURPLE OF THE ANCIENTS ; PURPUROGALLIN ; QUEBRACHO COLORADO ; QUERCETAGETIN ;
QUERCITRON BARK ; RAMALIC ACID ; RED DURA ; ROBINIA PSEUD-ACACIA ; RUBIA
KHASIANA ; RUBIA SIKKIMENSIS ; SAFFLOWER ; SAFFRON ; SANDERSWOOD ; SAPONARIA
OFFICINALIS; SCOPARIN; SCUTELLARIN.]

Dr. J. C. PHILIP, M.A., Lecturer on Physical Chemistry, Imperial College of Science
and Technology, South Kensington. [REFRACTOMETER.]

SPENCER U. PICKERING, Esq., M.A., F.R.S., Harpenden, Herts. [PLANT SPRAYS.]

Dr. J. B. READMAN, F.R.S.E. [PHOSPHORUS.]

Sir BOVERTON REDWOOD, Bart., F.I.C., F.C.S., London. [PETROLEUM.]

Dr. THOMAS K. ROSE, A.R.S.M., The Royal Mint, London. [SILVER.]

Dr. F. W. RUDLER, I.S.O., late of the Museum of Economic Geology, Jermyn St., London.
[OILSTONE ; PEARLS ; PORPHYRY ; PYRRHOTITE ; SANDSTONE ; SLATE.]

Dr. S. P. SADTLER, Philadelphia, U.S.A. [AMERICAN PETROLEUM.]

Dr. PHILIP SCHIDROWITZ, Analytical and Consulting Chemist, London. [RUBBER.]

Dr. S. B. SCHRYVER, Cancer Hospital Research Institute, Brompton, London. [PROTEINS.]

FRANK SCUDDER, Esq., F.I.C., Analytical and Consulting Chemist, Manchester.
[SEWAGE.]

Dr. ALFRED SENIER, F.I.C. , Professor of Chemistry, University College, Galway.
[OLEO-RESINS ; OPIUM; ORDEAL BEAN; PEPSIN; PICROTOXIN; QUASSIA; RESINS;
RHUBARB-ROOT ; SANTONICA ; SARSAPARILLA ; SENEGA ROOT ; SENNA LEAVES.]

Dr. IDA SMEDLEY (Mrs. HUGH MACLEAN), London. [PERFUMES (SYNTHETIC).]
ARTHUR SMITHELLS, Esq., F.R.S., Professor of Chemistry in the University of Leeds.

[RUST.]

L. J. SPENCER, Esq., M.A., Mineralogical Department, British Museum, London.
[OLIVINE ; ONYX ; ONYX-MARBLE ; OPAL ; ORANGITE ; ORPIMENT ; ORTHITE ; PATRONITE ;
PENTLANDITE ; PETALITE ; PHOSPHORITE AND ROCK-PHOSPHATE ; PITCHBLENDE ;
POLYBASITE ', POLYHALITE ; PRECIOUS STONES ; PROUSTITE ; PsiLOMELANE ; PUMICE ;
PYRARGYRITE ; PYRITES ; PYROLUSITE ; PYROMORPHITE ; PYROPHYLLITE ; QUARTZ ;
QUISQUEITE ; REALGAR; RHODOCHROSITE ; RHODONITE; ROSCOELITE; RUTILE;
SAMARSKITE ; SAMSONITE ; SAND ; SASSOLITE ; SCHEELITE ; SERPENTINE ; SMALTITE ;
SODALITE.]

Miss BEATRICE THOMAS, M.A., Girton College, Cambridge. [PTOMAINES.]

Professor J. MILLAR THOMSON, LL.D., F.R.S., King's College, London. [PHOTOGRAPHY.]

Sir WILLIAM A. TILDEN, LL.D., F.R.S., Emeritus Professor of Chemistry in the
Imperial College of Science and Technology, South Kensington. [RESIN OIL.]

Dr. LEONARD T. THORNE, F.I.C., London. [OXYGEN; OZONE.]

Dr. JOCELYN F. THORPE, F.R.S., Sorby Research Fellow, University of Sheffield.
[OXAZINE COLOURING MATTERS ; PHENOL AND ITS HOMOLOGUES ; PYRAZOLONE
COLOURING MATTERS.]

Dr. MARTHA A. WHITELEY, A.R.C.S., Demonstrator in Chemistry, Imperial College of
Science and Technology, South Kensington. [ORNITHINE ; PARABANIC ACID ;
PARAXANTHINE ; PHENYLALANINE ; PROLINE; PURINES; PYRIMIDINES OR METADI-
AZINES; SERINE.]

Dr. W. PALMER WYNNE, F.R.S., Firth Professor of Chemistry in the University
of Sheffield. [PHENANTHRENE ; QUINOLINE.]



DICTIONAEY

OF

APPLIED CHEMISTEY.



OILSTONE. A fine-grained hone-stone usec
with oil for sharpening edged tools. The most
celebrated is the Turkey oilstone, an extremely
hard and compact material, obtained in the in-
terior of Asia Minor, and exported from Smyrna.
It contains 70-75 p.c. silica, 20-25 p.c. calcium
carbonate, and a little alumina. Two varieties
are recognised, the white and the black, the
latter being slightly the harder. In this
country the Charley Forest stone has obtained
great repute as an oilstone for whetting tools
and penknives. It is a fine-grained, silicious,
slaty rock, worked at Whittle Hill in Charnwood
Forest, Leicestershire. The Welsh oilstone is a
somewhat similar material, from near Llyn Idwal
in North Wales, whilst the Devonshire oilstones
are obtained from the neighbourhood of Tavi-
stock. Several kinds of oilstone are worked in
the United States. The Arkansas stone is a
compact or fine-grained rock of bluish-white
colour, used for delicate instruments, like those
of surgeons and watchmakers. Somewhat
similar, but more abundant, is the Washita oil-
stone, a white, opaque stone used chiefly by
carpenters, from the Washita (or Ouachita)
River, Arkansas. The name * novaculite ' is also
applied to the Arkansas and Washita stones.
Their material consists almost entirely of
chalcedonic silica (99-5 p.c.).

In preparing oilstones for use, the rough
pieces are cut into regular shapes on the lapi-
dary's wheel, fed with diamond powder, and are
rubbed smooth with sand or emery on an iron
plate. The slab of stone is in some cases
cemented to a wooden base, by means of putty.
Some of the stones are used not only for sharpen-
ing tools, but for finishing turned and planed
surfaces of metal work. Oilstone powder is also
employed for grinding the brass fittings of
mathematical instruments (v. R. Knight, Trans.
Soc. Arts, 50, 233 ; C. Holtzapffel, Turning, vol.
3, 1081 ; and G. P. Merrill, The Non-metallic

erals, 2nd edit., 1910 ; v. also Whetstones).

F. W. R.

OKRA, also called gumbo ; Hibiscus escu-
lentus (Linn.), an annual plant bearing edible
VOL. IV. T.



6, 1

Min





pods. Zega (Chem. Zeit. 1900, 24, 871) found

as the average of 4 analyses
Water Protein Fat N-free extract Fibre Ash
80-7 4-2 0-4 12-1 1-2 1-4

According to American analyses (Bull. 28, U.S.

Dept. of Agric. 1899), the edible portion of the

pods, used largely as a vegetable in America,

is much more watery, as shown by the following

figures :

Water Protein Fat N-free extract Crude fibre Ash
90-2 1-6 0-2 4-0 3-4 0-6

whilst, according to the same authority, canned

okra contains



Fat
0-1



N-free extract Crude fibre Ash
2-9 0-7 1-2



Water Protein
94-4 0-7

(v. also Tinsley, Amer. Chem. J. 1893, 14,
625). H. I.

OLD FUSTIC is the wood of a tree known
as the Chlorophora tinctoria (Gaudich), pre-
viously called Morus tinctoria (Linn.) which
occurs wild in different tropical regions. The
tree frequently grows to a height of over 60
feet, is exported in the form of logs, sawn
straight at both ends, and usually deprived of
the bark. The best qualities of old fustic come
from Cuba and the poorer from Jamaica and
Brazil. It is at the present time used very
largely, and, together with logwood, is the most
important of the natural dyestuffs.

The colouring matters of old fustic were
first investigated by Chevreul (Le$ons de chimie
applique"e a la teinture, II. 150), who described
two substances, one sparingly soluble in water,
called morin, and a second somewhat more
readily soluble. Wagner (J. pr. Chem. [i.] 81,
82) termed the latter moritannic acid, and
considered that it possessed the same percentage
composition as morin. Hlaziwetz and Pfaundler
'Annalen, 127, 351), on the other hand, found
that the so-called moritannic acid was not an
acid, and as moreover its composition and
properties were quite distinct from those of
rnorin, they gave it the name ' Maclurin.'

Morin C 15 H 10 O 7 ,2H 2 O. To isolate this
colouring matter from old fustic a boiling extract



OLD FUSTIC.



of the raspejl wpod.is treated with a little acetic
aqi4 's-ld, t&en: vtith.Had acetate solution. This
' cause's fcKe pre'cipitation'of 'the morin in the form
of its yellow lead compound, whereas the main
bulk of the maclurin remains in solution. The
washed precipitate in the form of a thin cream
is run into boiling dilute sulphuric acid, and the
hot liquid, after decantation from the lead
sulphate, is allowed to stand. Crystals of crude
morin are gradually deposited, and a further
quantity can be isolated from the acid solution
by means of ether. During the preparation of
commercial fustic extract, the solution on stand-
ing, or the concentrated extract itself, deposits,
as a rule, a brownish-yellow powder, which con-
sists principally of a mixture of morin and its
calcium salt, and this forms the best source for
the preparation of large quantities of the colour-
ing matter. The product is digested with a
little boiling dilute hydrochloric acid to decom-
pose the calcium compound, extracted with
hot alcohol, and the extract evaporated. Crystals
of morin separate on standing, and a further
quantity can be isolated by the cautious addition
of a little boiling water to the mixture.

Crude morin can be partially purified by
crystallisation from dilute alcohol or dilute
acetic acid, but the product usually contains a
trace of maclurin. To remove the latter the
finely powdered substance is treated in the
presence of a little boiling acetic acid with
fuming hydrobromic acid (or hydrochloric acid),
which precipitates the morin as halogen salt,
whereas the maclurin remains in solution
(Bablich and Per kin, Chem. Soc. Trans. 1896, 69,
792). The crystals are collected, washed with
acetic acid, decomposed by water, and the
regenerated morin crystallised from dilute
alcohol.

Morin crystallises in colourless needles
(B. and P.), readily soluble in boiling alcohol,
soluble in alkaline solutions with a yellow
colour. Lead acetate solution gives a bright
orange-coloured precipitate and ferric chloride
an olive-green colouration.

Loewe (Zeitsch. anal. Chem. 14, 112) was
the first to assign to morin the formula C 15 H 10 O 7 ,
and that this was correct was shown by the
analysis of its compounds with mineral acids
(Perkin and Pate, Chem. Soc. Trans. 1895, 67,
649). The hydrochloride, hydrobromide, and
hydriodide are obtained in orange-coloured
needles, and possess the formulae C 15 H 10 7 -HC1,
C 15 H 10 7 -HBr, and C 15 H 10 0/HI, but the
sulphuric acid compound, known as anhydro-
morin sulphate C 15 H 8 6 -H 2 S0 4 , orange-red
needles, is of an abnormal character. Mono-
potassium morin C 15 H 9 O 7 K, yellow needles,
monosodium morin C 15 H 9 O 7 N 'a, magnesium morin
(C 15 H 9 7 ) 2 Mg, orange-yellow needles, and
barium morin (C 15 H 9 7 ) 2 Ba, orange crystalline
powder, have also been prepared (Perkin,
Chem. Soc. Trans. 1899, 75, 437).

When an alcoholic solution of morin is
treated with bromine (Benedikt and Hazura,
Monatsh. 5, 667 ; Hlaziwetz and Pfaundler, J.
1864, 557) it is converted into tetrabrom-morin
ethyl ether C 15 H 5 Br 4 O 7 Et,2H 2 0, colourless
needles, m.p. 155 (Herzig, Monatsh. 18, 700),
and this when digested with stannous chloride
and hydrochloric acid gives tetrabromo-morin
C 15 H B Br 4 7 (B. and H.), colourless needles,



m.p. 258. According to Perkin and Bablich,
this latter compound is more simply prepared
by the direct bromination of morin suspended
in acetic acid.

Morin forms few crystalline derivatives. By
the action of acetic anhydride, according to the
usual methods, a colourless amorphous product
results, and a crystalline pentacetylmorin has
not yet been prepared. Cold acetic anhydride,
however, converts the monopotassium salt of
the colouring matter into tetra-acetyl morin
C 15 H 6 7 (C 2 H 3 0) 4 , colourless prismatic needles,
m.p. 142-145, but this on further acetylation
gives an amorphous compound.

Tetrabromomorin, on the other hand, yields
a penta-acetyl derivative (Bablich and Perkin)
C 15 HBr 4 7 (C 2 H 3 0) 5 , colourless needles, 192-
194, and it was subsequently found by Herzig
that tetrabromomorin ethyl ether yields the
compound C 15 HBr 4 7 Et(C 2 H 3 0) 4 , m.p. 116-
120.

By fusion with alkali morin gives phloro-
glucinol (H. and P.), and resorcinol (B. and H.),
whereas in this manner Bablich and Perkin
isolated fi-resorcylic acid. When methylated
with methyl iodide morin tetramethyl ether
C 15 H 6 3 (OCH 3 ) 4 (B. and P.), yellow needles,
m.p. 131-132, is produced, but is isolated
with difficulty, and from this compound with
alcoholic potash a yellow potassium salt, readily
decomposed by water, is obtained. Mono-
acetyltetramethylmorin C 15 H 5 3 (OCH 3 ) 4 C 2 H 3 0,
colourless needles, melts at 167.

Morin tetraethyl ether C 16 H 6 3 (OC 2 H 5 ) 4
(Perkin and Phipps, Chem. Soc. Trans. 1904,
85, 61), yellow needles, m.p. 126-128, and
acetylmorintetraethyl ether

C 15 H 5 3 (OC 2 H 5 ) 4 C 2 H 3 0,

colourless needles, m.p. 121-123, could only
be prepared in small quantity.

When morin tetramethyl ether is hydrolysed
with alcoholic potash p-resorcylic acid dimethyl
ether, and phloroglucinolmonomethyl ether are
produced. Bablich and Perkin assigned to
morin the constitution of a pentahydroxyflavone
(tetrahydroxyflavonol)



OH



and that this formula correctly represents the
substance, has been proved by its synthesis
(Kostanecki, Lampe and Tambor, Ber. 1906,
39, 625), and also by the investigation of Herzig
and Hofmann (Ber. 1909, 42, 155). It has
been shown by the latter chemists that when
morin is methylated by means of methyl sul-
phate morin pentamethyl ether C 15 H 3 2 (OCH 3 ) 5 ,
needles, m.p. 154-157, can be produced.
This compound is hydrolysed with boiling
alcoholic potash into fi-resorcylic acid dimethyl
ether (1), and fisetol trimethyl ether (1) (c/.
QTJEBCETIN and FISETIN)

OCH 3 /\- OH COOH/ \OCH 3

(1) ,_CO-CH 2 OCH 3 (2) \ oc

OCH 3
the latter being identical with the compound




OLD FUSTIC.



obtained in a similar way from quercetin
pentamethyl ether.

Kostanecki, Lampe and Tambor (Ber. 1906,
39, 625) have synthesised morin by reactions
similar to those found serviceable in the artificial
preparation of fisetin and quercetin (-see YOUNG
FUSTIC and QUERCITRON BARK), but in this case
the formation of the flavanone did not pro-
ceed smoothly and only a small quantity could
be prepared. The synthesis is illustrated by the
following formulae

OCH 3

^ OH CH



CH 3



CH 3



,_CO-CH

OCH 3

2 ; -hydroxy-4': 6':2 :4-tetramethoxy chalkone .

OCH 3

I f



OCH,

l:3:2':4'-tetramethoxyflavanone.
OCH 3



CH 3



,C : NOH



CO'



a-isonitroso-l:3:2':4'-tetramethoxyflavanone.
OCH 3




Morin.

Morin dyes mordanted woollen cloth shades
which, though of a slightly stronger character,
closely resemble those given by kaempferol.

Chromium Aluminium Tin Iron
Morin . Olive yellow Yellow Lemon Deep olive

yellow brown
Kaempferol Brown yellow ,, Bright Deep olive

yellow brown

(Perkin and Wilkinson, Chem. Soc. Trans.
1902, 81, 590).

Maclurin C 13 H 10 6 . When morin is pre-
cipitated from a hot aqueous extract of old
fustic by means of lead acetate the solution
contains maclurin. After removal of lead in
the usual manner, the liquid is partially evapo-
rated and extracted with ethyl acetate, which
dissolves the colouring matter. The crude
product is crystallised from dilute acetic acid
(Perkin and Cope). A crude maclurin is also
obtained during the preparation of fustic extract,
partially in the form of its calcium salt, and
this product is treated with dilute hydrochloric
acid and crystallised from water. In order to
decolourise the crystals, acetic acid is added to
a hot aqueous solution and a little lead acetate
in such quantity that no precipitate is formed,



and the solution is treated with sulphuretted
hydrogen. The clear liquid is now much less
strongly coloured, and after repeating the opera-
tion two or three times, the maclurin, which
crystallises out on standing, possesses only a
pale yellow tint.

When quite pure maclurin consists of
colourless needles, m.p. 200 (Wagner, J. 1850,
529), somewhat soluble in boiling water, soluble
in alkalis with a pale yellow colouration. With
aqueous lead acetate it gives a yellow precipitate
and with ferric chloride a greenish- black coloura-
tion.

Hlasiwetz and Pfaundler (J. 1864, 558)
assigned the formula C 13 H 10 6 to maclurin,
and found that by boiling with potassium
hydroxide solution it gives phloroglucinol and
protocatechuic acid.

Pentabenzoylmaclurin C 13 H 6 6 (C 7 H 5 0).
melts at 155-156 (Konig and Kostanecki, Ber.
1894, 27, 1996) ; and tribrom maclurin

C 13 H 7 Br 3 6 ,H 2 0,

colourless needles has been obtained by Benedikt.
Maclurin pentamethyl ether C 13 H 6 0(OCH 3 ) 5 ,
colourless leaflets, melts at 157. Konig and
Kostanecki first assigned to maclurin the con-
stitution of a pentahydroxybenzophenone
OH

\_CO-AOH



om 'OH



W. H. Perkin and Robinson (Chem. Soc. Proc.
1906, 22, 305), and somewhat later Kostanecki
and Tambor (Ber. 1906, 39, 4022) synthesised
maclurin pentamethyl ether, by the interaction
of veratric acid and phloroglucinol trimethyl
ether in presence of aluminium chloride
OCH 3

I Innw +



OCH.



OCH 3



OCH 3



OCH,



= OCH I JOCH 3 I IOCH 3 +H2 '

Pentamethylmaclurin .

When maclurin pentamethyl ether is digested
with alcoholic potash and zinc-dust leucomaclurin-
pentamethyl ether (Kostanecki and Lampe, Ber.
1906, 39, 4014)

OCH 3

CH(OH) j



I I



OCH 3



is produced in prismatic needles, m.p. 109-
110, and this on further reduction gives penta-



Online LibraryT. E. (Thomas Edward) ThorpeA dictionary of applied chemistry (Volume 4) → online text (page 1 of 172)