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tallised nitrobenzoic acid is formed. It is not changed either by aqueous
ammonia or by ammoniacal gas. By boiling with potash-ley, it is par-
tially decomposed, with formation of chloride of potassium. With sodium,
it gives off gas, which is perhaps hydrogen, becomes hot, and at length
takes fire with explosion. (Stenhouse.)

Dissolves with difficulty in water, easily in alcohol, and is precipitated
by water. (Herzog.)

With this oil is probably identical the oil which Toel obtained by acting
with alcoholic potash on an alcoholic solution of chlorostyracin (p, 299),
filtering off the liquor from the resulting chloride of potassium and chloro-
cinnamate of potash, evaporating the alcohol, and precipitating with
water. According to Toel, it is a tolerably colourless oil which may be
distilled with water without decomposition, has a peculiar odour, and a
sharp burning taste. It rapidly becomes brown in the air, burns with
green-edged flame when set on fire, and dissolves with tolerable facility
in water.



Chlorine-nucleus C 18 C1 4 H 4 .

Tetrachlorocinnamyl.

4 2 _ C 18 C1 4 H 4 ,0 2 .



DUMAS & PELIGOT. Ann. Chim. Phys. 57, 316.

Tetrachlorcinnamyl, Chlorocinnose, Hydrure de quadrichlorocinnamyle.

Oil of cinnamon is distilled four or five times in a stream of chlorine,
until the distillate in the receiver solidifies in long white needles, which
may be obtained pure by pressing between paper.

Beautiful, dazzling white needles. Melts and sublimes unchanged at
a gentle heat.



18 C


. 108


39-94


Dumas &
Peligot.
39-33


4 Cl


... 142-4 ....


52-66


52-75


4 H


4


1-48


1-85


2 O


... 16 ....


5-92


6 07



C 18 C1 4 H 4 O 2 270-4 .... 100-00 100-00

It is not changed by boiling oil of vitriol. Not altered by distilla-
tion in dry ammoniacal-gas.

Dissolves in boiling alcohol, and crystallises on cooling.



CHLOROSTYRACIN. 299



Chlorostyracin.

= C 18 C1 4 H 5 0,C 18 H 7 3



TOEL. Ann. Pharm. 70, 6.
STRECKER. Ann. Pharm. 70, 10.
E. KOPP. Compt. chim. 1850, 144.

Dry chlorine is passed over styracin, ultimately at' 100, and the pro-
duct is freed from excess of chlorine by repeated solution in alcohol and
evaporation.

Yellow, tough, sticky mass. Smells like balsam of copaiva. Has a
sharp and grating taste.



36 C


216 ....


53-68 .


Toel.
53-64


4 Cl


142-4 ....


35-38 ,


35-50


12 H


12


2-98




4 O


.... 32 ....


7-96













C36 C1 4 H 12Q4 402-4 .... 100-00

Toel at first proposed the formula C^CFH^O 8 .

Its alcoholic solution left to stand with excess of alcoholic potash,
decomposes into chloride of potassium, chlorocinnamate of potash, and a
chlorinated oil, which remains dissolved in alcohol (p. 298). (Toel.)

Distilled in a stream of chlorine, it yields a volatile chlorinated oil,
and a crystallisable chlorinated acid which forms salts very readily
crystallisable. (E. Kopp.)

Chlorostyracin does not dissolve in water. It dissolves in hot alcohol
and ether, from which it again separates as an amorphous mass. (Toel.)



Cyanogen-nucleus C 18 CyH 7 .

Cyanide of Cinnamyl.

C 20 NH 7 2 = C 8 CyH 7 ,0 2 .

CAHOURS. N. Ann. Chim. Phys. 23, 341; J. pr. Chem. 45, 140; Ann.
Pharm. 70, 42.

In the distillation of chloride of cinnamyl with cyanide of potassium
or cyanide of mercury, a liquid passes over which rapidly becomes brown
in the air, while hydrocyanic acid and cinnamic acid are formed. This
liquid still contains chlorine, but is composed for the most part of cyanide
of cinnamyl.



300 PRIMARY NUCLEUS C 18 H 8 : NITRO-NUCLEUS C 18 XR7.



20 C


120


76-35


Cahours.
72'23


N


14


9-01


7*44


7 H


7 ....


4-45


4-39


2 O


16


10-19


15-94











C20NH7Q 2 157 .... 100-00 ....... 100-00


Nitro-nuclem C 18 XH 7 .

Nitrocinnamic Acid,

C 18 NH 7 8 = C 18 XH 7 ,0 4 .

MITSCHERLICH. (1841.) N. Ann. Chim. Phys. 4, 73; 7, 5; J. pr. Chem.

22, 192.
E. KOPP. Compt. rend. 24, 614; N. J. Pharm. 11, 426; J. pr. Chem.

41, 425; Compt. chim. 1849, 146.
J. WOLFF. Ann. Pharm. 75, 303.

Nitrozimmtsaure, Zimmtsalpetersaure.

Formation. 1 . By the action of concentrated nitric acid on cinnamic
acid. (Mitscherlich, Kopp.) 2. By heating styrone with nitric acid,
with addition of urea (p. 257). (Wolff.)

Preparation. Concentrated nitric acid is freed from nitrous acid by
boiling, and after cooling, about one-eighth of cinnamic acid is added.
The cinnamic acid dissolves in a few minutes, without disengagement of
gas, the liquid becomes heated to 40, and a mass of crystals is deposited.
In order to obtain larger quantities, cinnamic acid is triturated with
nitric acid, and cooled, so that the temperature may not rise above 50;
the mass is washed with cold water, till all nitric acid is removed,
then dissolved in boiling alcohol, and filtered; and the resulting crystals
are washed with cold alcohol. (Mitscherlich.) Kopp dissolves 1 part
of powdered cinnamic acid in 3 parts of monohydrated nitric acid, freed
from nitrous acid by passing a dry stream of air through it, the mixture
then solidifying almost immediately in consequence of the crystallisation
of the nitrocinnamic acid; washes the magma with water; then dries and
sets it aside for 24 hours with 4 parts of cold alcohol, which removes any
benzoic acid that may be present.

Properties. Very small, white crystals, with a faint yellowish tint.
Melts at about 270, and solidifies to a mass of crystals on cooling. Boils
a little above 270 with decomposition. (Mitscherlich.)



18 C .. .


108 ..


Mitscherlich.
.. 55-95 55-57 ....
.. 7-25 7-73
3-62 3-64 ....
.. 33-18 33-06


Wolff.
55-6

4-0


"N"


14


7 H


7


8 ....


64 ..



C 18 XH?O 4 193 , .. 100-00 . .. 100-00



NITROCINNAMATE OF ETHYL. 301

Forms carbostyril with sulphide of ammonium. (Chiozza.) When
nitrocinnamic acid is dissolved in alcoholic sulphide of ammonium, sulphur
separates on gently warming the liquid, while a yellow resin and an
alkaloid remain dissolved. The latter is colourless and crystallisable,
does not dissolve in water, but is soluble in alcohol and in ether, and
forms difficultly crystallisable salts. (E. Kopp.)

Nitrocinnamic acid may be boiled with excess of alkali without
decomposition.

Nitrociunamic acid scarcely dissolves in cold water, and very little
in boiling water. It does not melt to an oil when boiled with water.

It is slightly soluble without decomposition in boiling hydrochloric
acid. With bases, it acts as a feeble acid and expels carbonic acid. The
salts with alkaline bases are obtained by dissolving the acid in the
aqueous base; the rest are obtained by precipitating with the ammonia-
salt. The nitrocinnamates of ammonia, potash, and soda, are readily
soluble; the others are sparingly soluble, or insoluble. Strong acids
decompose them, liberating nitrocinnamic acid.

Nitrocinnamate of Ammonia. The solution gives off" ammonia when
evaporated, and deposits uitrocinnamic acid in indistinct crystals.

Nitrocinnamate of Potash. Deposited in nodules when the solution is
evaporated; on addition of caustic potash, it is deposited in distinct prisms.
Permanent in the air.

Nitrocinnamate of Magnesia. With magnesia-salts, nitrocinnamate
of ammonia forms, after some time, nodular crystalline groups which
dissolves with tolerable facility in water.

Nitrocinnamate of Silver is precipitated in the pulverulent form on
adding the ammonia-salt to nitrate of silver. After being dried at 100,
it does not give off water at 140, at which point decomposition begins.
When carefully heated, it decomposes so gradually that no silver escapes
as dust. Very sparingly soluble in water.

Dried at 100. Mitscherlich.

AgO 116 .... 38-66 38-18

C 18 XH 6 O 3 184 .... 61-34

C 18 AgXH 6 O 4 .... 300 .... 100-00

Nitrocinnamic acid dissolves in 327 parts of absolute alcohol at 20.
(Mitscherlich.)



Nitrocinnamate of Ethyl.

C 22 NH n 8 = C 4 H 8 0,C 18 XH 6 O a .

MITSCHERLICH. (1841.) J. pr. Chem. 22, 194.

E. KOPP. Compt. rend. 24, 615; N. J. Pharm. 11, 72.

Nitrocinnamic ether, Nitrozimmtvinester, Zimmtsalpeters'dure-naptha.
Formation. By heating together nitrocinnamic acid with alcohol and



302 PRIMARY NUCLEUS C 18 H 8 : OXYAMIDOGEN-NUCLEUS C 18 AdH 5 O 2 .

oil of vitriol. (Mitscherlich.) By the action of concentrated nitric acid
on cinnamic ether. (E. Kopp.)

Preparation. When 1 part of nitrocinnamic acid is heated with 20
parts of absolute alcohol and a little oil of vitriol, at a temperature not
exceeding 80, the acid gradually dissolves, and the ether crystallises out
on cooling. It is dissolved in alcohol containing ammonia, and allowed
to crystallise.

Prisms which melt at 136. Boils at about 300 with decomposition.



22 C


132


59-73


Mitscherlich.

58-88


N


14


6-34




11 H


11


4-97


4-96


8 O


64 ....


28-96





C 22 NH n O 8 221 .. 100-00



By boiling with potash it is converted into nitrocinnamate of potash
and alcohol.



Nitrocinnamic Anhydride,

i4 _ C 18 XH 6 3 ,C 18 XH 6 3 .



CHIOZZA. (1853.) N. Ann. Chim. Phys. 39, 231; Compt. rend. 36, 631;
Gerhardt, Traite 3, 388.

Formed by the action of oxychloride of phosphorus on nitrocinnamate
of potash.

Melts in boiling water more easily than nitrocinnamic acid, forming
a yellow resin which is easily kneaded.

Readily takes up water, and is converted into nitrocinnamic acid.
With ammonia it easily forms nitrocinnamide and nitrocinnamate of
ammonia. With alcohol it forms nitrocinnamic ether.

Sparingly soluble in ether.



Oxyamidogen-nudeus C 18 AdH 5 2 .

Carbostyril.

= c i8 AdH 5 OM



L. CHIOZZA. Compt. rend. 34, 598; J. pr. Chem. 70, 278.

When uitrocinnamic acid is heated with sulphide of ammonium to the
boiling point, sulphur is separated, and on supersaturating the mixture



CINNANILIDE. 303

with hydrochloric acid, a liquid, coloured brown by a resin, is produced.
This liquid, when evaporated, yields crystals, which are freed from adhe-
rent resin by recrystallisation from boiling alcohol.

White silky needles. When heated, it melts to a colourless oil,
which solidifies in the crystalline form on cooling, and sublimes in lustrous
needles, at a higher temperature.







(


^hiozza.








mean.


18 C


108 ....


74-5


74-6


N


14 ....


9-9


10-0


7 H


7 .


4-9


5-1


2 O


16 ....


10-7


10-3











C 18 NH7Q 2 145 .... 100-0 100*0

Remains unchanged when heated with oil of vitriol. Caustic potash
readily dissolves carbostyril, and on heating a volatile base appears to
be formed.

Nearly insoluble in cold, but readily soluble in boiling water. Dis-
solves in hydrochloric acid, not in ammonia.



Conjugated compounds containing C 18 H 8 , or a derived nucleus.

Cinnanilide.

C 30 NH 13 2 = C 18 (C 12 H 5 )AdH,0 2 .

CAHOURS. N. Ann. Chim. Phys. 23, 344; J. pr. Chem. 45, 142.

Formation and Preparation. Aniline becomes strongly heated with
chloride of cinnamyl. The resulting solid mass is repeatedly washed
with water and dilute potash, and the residue dissolved in hot alcohol:
cinnanilide then crystallises out on cooling.

Delicate needles, which melt at a moderate heat, and distil without
decomposition at a higher temperature.









Cahours.








mean.


30 C ..


180 ..


.. 80-72


80-46


N


14


6-28


6'41


13 H


.. . 13


5-83


6-13


2 O


16 ..


.. 7-17


7-00



........ 223 .... 100-00 ........ 100-00



It is scarcely attacked by potash-ley. When distilled with hydrate
of potash, it decomposes into aniline and ciunamate of potash.



304 CONJUGATED COMPOUNDS CONTAINING C^H^ & C .



Cinnanitranisidine,

i4 8 = c u AdXH 5 0,C 18 H r 3 .

CAHOURS. JT. Ann. Chim. Phys. 27, 252.

Cinnanisidide nitrique, Azoture de cinnamyle, de methyl-nitrophenyle, et
d'hydrogfrne.

When crystals of nitranisidine are introduced into chloride of ciu-
namyl, hydrochloric acid is liberated, and a solid mass is formed which
may be purified like benzonitranisidine.

Crystallises from hot alcohol in yellowish needles.



32 C


192


64-43


Cahours.
64-52


2 N .


. 28


9'39




14 H


14


4-69 ..


4-82


8 O


64


.... 21-49













C 32 N 2 H 14 O 8 .... 298 .... 100-00

It is therefore cinnamate of nitranisidine minus 2HO (Cahours.)



Hydrocinnamide.



DUMAS & PELIGOT. Ann. Chim. Phys. 57, 325.
LAURENT. Rev. scient. 10, 119; J. pr. Chem. 27, 309.
BERZELIUS. Jahresber. 23, 442.
CAHOURS. Compt. rend. 25, 458.

Hydrure d'azocinnamyle, Cinnhydramide, Cinnamyl-subnitrur.

Oil of cinnamon recently prepared from Ceylon cinnamon, is treated
with dry ammonia, and the viscid product is dissolved in ether-alcohol,
from which beautiful crystals of hydrocinnamide crystallise on cooling :
they are purified by recrystallisation. (Laurent.)

Properties. Colourless, rectangular prisms. (Laurent.) Lustrous
silky tufts. (Dumas and Peligot.) The base is replaced by two rectan-
gular faces, intersecting at a very obtuse angle. Melts and solidifies on
cooling, to a transparent, gummy, non-crystalline mass. (Laurent.)
Permanent in the air. (Dumas and Peligot.)



54 C
2 N


324

28


.... 86-17
7-44


Laurent.
85-4
7'6


24 H


24


6-39


6-5











C 54 N 2 H 24 376 .... 100-00 99-5



TRIPHENYLAMINE. 305

According to Dumas and Peligot, it is C 1S H 8 O 2 ,NH 3 and contains ll'O p. c.
ammonia, inasmuch as these chemists found that 100 parts of oil of cinnamon take up
12-3 parts (11'56 Mulder) of ammonia.

Decompositions. 1. It is decomposed by dry distillation, yielding an
oil and a solid substance. (Laurent.) 2. Not decomposed by water.
(Dumas and Peligot.) 3. When dissolved in alcohol, it is changed by
sulphuretted hydrogen into thiocinnol. (Cahours,) 4. It is not altered
by boiling hydrochloric acid, or boiling alcoholic potash. (Laurent.)
5. Decomposed by boiling nitric acid, yielding a substance which melts
in boiling water. (Laurent.)

Dissolves in alcohol and in ether, and crystallises out on cooling.
(Dumas and Peligot.)



Triphenylamine or Bicinnamylamine.

= C 18 (C 18 H 7 )NH 6 ,H 3 .



GOSSMANN. Ann. Pharm. 100, 57; J~. pr. Chem. 70, 288.

According to Gossmann, it is triphenylamine = (C 12 H 5 ) 3 E". (See xi, 334.)

Preparation. Recently prepared bisulphite of cinnamic aldehyde-
ammonia is distilled with lime, and by careful heating, a dark yellow,
oily and aqueous distillate is obtained. This liquid is boiled with dilute
aqueous potash, or carbonate of soda in order to remove the ammonia
and the hydrocarbons; freed from alkali by repeated washings with
continually smaller quantities of hot water ; dried as far as possible,
and heated in a stream of hydrogen, at first to remove the last traces of
water; and then distilled, the temperature being kept at 140 150
as long as possible. If the temperature were raised to strong ebullition,
decomposition would ensue.

Properties. Colourless oil, heavier than water. Smells feebly of oil
of cinnamon. Has an alkaline reaction.

Decompositions. 1. In moist air it becomes yellow, then reddish,
owing to the formation of a red colouring matter very difficult to remove.
2. Dissolves readily in iodide of ethyl, with slight rise of temperature;
after 24 hours, the liquid becomes filled with large crystalline plates,
which decompose after a few days, the liquor then becoming turbid, and
depositing hydrate of ethyltriphenylainine (or ethylbicinnamylamine) as a
red oil.

Combinations. Dissolves with difficulty in water. The salts, with
the exception of the platinum double salt, readily change in the air,
especially in aqueous or alcoholic solution, a red colouring matter being
formed.

Hydrochlorate of Bicinnamylamine. Concentrated hydrochloric acid
does not alter colourless bicinnamylamine; alcohol of 95 per cent, causes
the mixture to solidify to a colourless mass of crystals, which must be
washed with alcohol.

VOL. XIII. X



306 CONJUGATED COMPOUNDS CONTAINING C^H", &C.

Lustrous, somewhat reddish laminae. Not very changeable when
moist air is excluded.

When dissolved in water, alcohol or ether, it rapidly changes, and
then crystallises only after being evaporated in vacuo over oil of
vitriol.

Dissolves easily in water and alcohol, less readily in anhydrous alcohol
and ether. When ether containing alcohol is poured on it, it is deposited
as an oil, and dissolved on the addition of alcohol.

The Chloromercurate crystallises in laminee and decomposes on being
recrystallised.

Bicinnamylamine forms with nitrate of silver, a whitish yellow
compound, which presents but little appearance of crystallisation, and
soon acquires a chestnut-brown colour, probably from adhering cinnamic
aldehyde.

Bichloride of Platinum with Bidnnamylmine. When neutral alcoholic
bichloride of platinum is added to aqueous bicinnamylamine, a bright
chestnut-brown, bulky, granular, crystalline salt precipitates. When
freshly precipitated, it readily attracts moisture, but is permanent in the
air after drying. Heated with soda-lime, it is but partially decomposed,
with formation of ammonia. Dissolves readily in alcohol and in water.



36 C


216


.. 52-08


Gossmann.
52-22


N


14


3-38




15 H


15


3-62




Pt


99


.. 23-80




2 Cl


70


.. 17-12













C 36 NH i5 )PtC1 2 414 wt 100-00

Chloroplatinate of Bicinnamylamine. When an alcoholic solution of
bicinnamylamine is mixed with a recently prepared and moderately
strong alcoholic solution of bichloride of platinum, dark yellow bulky
flakes are precipitated, which may be washed with ether. (If washed with
alcohol, the flakes cake together to a resinous mass.)

Crystallises from an alcoholic solution on evaporation over oil of
vitriol, in chestnut-brown crystals belonging to the regular system, which
attain the size of 0*3 to 0'5 m.m., and have a glassy lustre. It is per-
manent in the air after drying, provided no excess of bichloride of plati-
num adheres to it.



36 C ...


216


47-88


Gossmann.
47-49


N


14


3-10




16 H


16


3-55


3-51


Pt


. 99


21-86


22-18


3 Cl


106-5 ...


23-61


23-50











C 36 NH 15 ,HCl + PtCl 2 451-5 .... lOO'OO

Oxalate of Bicinnamylamine. Deliquescent needles obtained by dis-
solving bicinnamylamine in alcoholic oxalic acid, and repeated crystal-
lisation from alcohol.



ETHYLBICINNAMYLAMINE. 30

Ethylbicinnamylamine.

_ C 12 (C 4 H S )(C 18 H 7 )NH 5 ,H 2 .



GOSSMANN. Ann. Pharm. 100, 65.

According to Gossmann, it is the hydrated oxide of ethyltriphenylammonium
= C^NH^O.HO. (See xi, 336.)

Bicinnamylamine is enclosed with excess of iodide of ethyl in glass
tubes, and the mixture left for several weeks or heated in the water-bath,
until the crystalline mass, which is at first formed, disappears, and an oily
layer which separates and floats on the surface, no longer increases. The
tubes are then opened, the contents dissolved in alcohol, the strongly acid
solution digested with excess of oxide of silver, and filtered, and the dis-
solved oxide of silver, precipitated by a little hydrochloric acid. When a
little water is added to the alcoholic solution, the base is deposited as an
oil; but when the alcoholic solution is poured into a large quantity of
water, the solution merely becomes turbid, owing to the presence of cer-
tain hydrocarbons which may be removed by filtration through a wet
filter.

Inodorous oil having a strong and pleasantly bitter taste, and a strong
alkaline reaction.

Dissolves with some difficulty in water; the solution deposits oil-drops
when boiled.

. The salts of ethylbicinnamylamine are deliquescent. The base dis-
solves oxide of silver.

Platinum Salt. Neutral bichloride of platinum precipitates from
hydrochlorate of ethylbicinnamylamine, an abundant cream-coloured
crystalline precipitate; the filtered solution, if rapidly concentrated,
deposits yellowish red, lustrous plates.

When boiled with a quantity of water insufficient for its solution, i
melts to a resin. The solution slowly evaporated deposits dark brick-red,
regular crystals of a glassy lustre, which at 90 100 become darke
and lose their lustre, and then experience no further change at ] 20



40 C


240 ....


Gossmann.
50-08 49-96
2-92 2-91
4-17 4-25
20-60 20-78
22-23 21-80


N


14 ....


20 H


20 . .


Pt


99


3 Cl ....


106-5 .







479.5 (i<< XOO-QO 99-70

Ethylbicinnamylamine dissolves easily in alcohol.



x 2



308 PRIMARY NUCLEUS C 18 H 10 .

Primary Nucleus C 18 H 10 .

Phloretic Acid.

C 18 H 10 6 s= C 18 H 10 ,0 6 .

HLASIWETZ. (1855.) Wien. Akad. Ber. 17, 382; J.pr. CJiem. 67, 105;
abstr. Ann. Pharm. 96, 118 ; J. pr. Chem. 69, 107 ; Ann. Pharm.
102, 145; Wien. Akad. JBer. 24, 237 ; Chem. Centralbl. 1857, 721;
J. pr. Chem. 72, 395.

Preparation. Phloretin is dissolved in so much potasli-ley of sp. gr.
1*25, that there shall be about 200 c.c. of liquid to half an ounce of phlore-
tin, and the solution is concentrated by boiling, until the mass becomes thick
and gelatinous. This is dissolved, treated with carbonic acid, and again
evaporated; the residue is boiled with alcohol; and the solution, which has
become clear by standing and has been poured off from some phloroglu-
cate of potash which separates as an oil, is mixed with ether, \vhereupon
phloretate of potash separates as an oily layer at the bottom. The super-
natant ether is decanted; the phloretate of potash dissolved in water; the last
traces of ether are expelled by boiling; and the solution, again evapo-
rated to a syrup and cooled, is mixed with a large excess of hydrochloric
acid, whereupon it solidifies to a crystalline magma, which is purified by
pressing, recrystallising from strong alcohol, which leaves chloride of
potassium, and then from water to which a little animal charcoal has
been added:

CWO 10 + 2IIO = C 18 H 10 O C -f C 12 H 6 O 6 .

The phloroglucin which forms at the same time, remains with the
carbonate of potash, if the above-named quantity of potash has been taken.
With less potash, alcohol would dissolve some of it.

Properties. Crystallised from water, it forms brittle prisms belonging
to the oblique prismatic system, an inch long, and with non-reflecting
faces; crystallised from ether it forms thick crystals an inch long and
half an inch broad, with imperfectly reflecting faces. Crystalline system,
the oblique prismatic. oP. ooPcc. Poo. -f f P . [P] + Pu.n.
Poo : ooP m = 138 51' ; + f Poo : ooPoo = 143 19' ; [Poo ] : oP =
114, 15'.

Melts at 128 130 without loss of weight, and becomes crystalline
on solidifying. Permanent in the air. Has a bitter, astringent taste, and
strong acid reaction.



18 C .


.. .. 108


.... 65-06


Hlasiwetz.
mean.
64-93


10 H
6 O


10
48


6-02
28-92


G-25
28 -82











C 18 H 10 O 6 166 .... 100-00 100-00

Hlasiwetz first gave the formula C 18 H U O 6 , which Gerhardt (Traite 4, 1068),
and Hlasiwetz himself afterwards, changed to C 18 H 10 O 6 . (See also Lieb. Kopp,
Jahresber. 1857, 327, and \Vurtz, N. Ann. Chim. Phijs. 52, 336.) Homologous with
salicylic acid.



PHLORETIC ACID. 309

Decompositions. 1. When heated, it gives off suffocating odours, burns,
and leaves very little charcoal. 2. With bromine it forms bibromophlo-
re tic acid. 3. Pulverised phloretic acid placed in a flask filled with
chlorine, melts, with disengagement of heat, the colour of the chlorine
disappearing, and hydrochloric acid appearing in its place. The product
dissolves in alcohol and in ether, but not in water; the solution when
evaporated, leaves a soft, sticky mass, which forms with soda a compound
solidifying after some time to a deliquescent crystalline mass. 4. With
hydrochloric acid and chlorate of potash, it assumes at first a reddish
brown colour, gives off abundance of gas when heated, again becomes
yellow, and partially changes into yellow flakes. 5. Triturated with
pentachloride of phosphorus, phloretic acid becomes warm and liquid,
and gives off much hydrochloric acid gas with effervescence. On distil-
lation, oxychloride of phosphorus passes over at 100, and a fuming
liquid remains, which decomposes with water, into phloretic acid, hydro-
chloric acid, and phosphoric acid, and at a higher temperature becomes
brown, froths up, and gives off a small quantity of oxychloride of phos-
phorus, leaving charcoal as a residue. 6. When concentrated nitric acid
is poured on phloretic acid, it dissolves, forming a red solution, with disen-
gagement of heat, intumescence, and liberation of red vapours; the solu-
tion on cooling becomes filled with yellow crystals of binitrophloretic acid.



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