A Manual of the Chemistry of the Carbon Compounds

THE CARBON COMPOUNDS', 359
By means of these reactions, artificial oil of bitter almonds is now
manufactured from toluene.
Sulpholmsaldehyde C8H6.CHS forms colourless crystals melting at
70"; it is prepared by heating benzylene dichloride with an alcoholic
solution of potassium sulphide.
C6H6.CH N
Hydrobmzamide, or Bmzylenediamine C.H..CH ,'is produced by
CaH6.CH
leaving benzaldehyde or its chloride in contact with aqueous ammonia;
it crystallizes in octahedrons, and is resolved by boiling water into
benzaldehyde and ammonia.
Amarine C^HyNj.—This isomeride of hydrobenzaraide is obtained
by the action of heat on the latter compound; and is also produced by
passing ammonia into an alcoholic solution of benzaldehyde. Amarine
crystallizes in glittering prisms melting at 100"; it has poisonous
properties, and is a base forming sparingly soluble salts.
LopHm CLHJJJNJ is formed by distilling hydrohenzamide ot amarine
; it is a base, crystallizing in long needles, melting at 2 l 70°.
When potassium cyanide is added to an alcoholic solution of benzaldehyde,
or crude oil of bitter almonds (containing prunsic acid) is
mixed with alcoholic potash, the aldehyde is converted into benzoin
CMHUO2, a compound which is a derivative of the radical stilbme
OMH12> and will be described afterwards.
BENZOIO ACID, OB PHENYLFORMIO ACID C6H6.00.0H.
This acid occurs in gum Benzoin (from Styrcuo benzoin), and is sometimes
found in the urine of herbivora, which always contains hippurio
or benzamidacetic acid. Benzole also exists as ghxeoside, called
populin, in the bark and leaves of the aspen. It has been produced
artificially by several reactions.
(1.) Au aromatic hydrocarbons containing only one alcohol-radical
wrc converted by oxidation with dilute nitric acid or chromic acid into
benzoic acid. It is also formed by oxidizing benzyl alcohol, beuzaldehyde(phenylaceticacidC0H6.CH4.CO8H,oinnamicacMC8H6.CSiH8.CO?H
and similar acids, and occurs among the products of oxidation of
albuminous substances.
(2.) Sodium benzoate is formed by passing carbon dioxide into a
mixture of bromobeuzene and sodium:—•
06H5.Br + CO8 + Na» = C6H6.CO8Na + NaBr
(3.) By treating the same mixture with ethyl chloroca chlorocatbonate, it
yields ethyl l benzoate :•—
C0HsBr + CO | JJj^ + % « C6H5.CO.00aH6 + l{aBr + NaCl