Benzoic aldehyde or bitter-almond oil is one of the oldest known products
of the vegetable kingdom, and has from time to time been made the subject
of investigation by chemists since the beginning of the century. It arises
from the fermentation of a nitrogenous compound found in the almond, and
known as amygdalin, the nature of the fermentative change undergone by
this substance having been brought to light by Woehler and Liebig. The
discovery of a green dye, requiring for its preparation a vegetable
product which was very costly, compelled the manufacturer to seek another
source of the oil. Pure chemistry again steps in, and solves the problem.
In 1863 it was known to Cahours that benzal chloride, on being heated with
water or alkali, gave benzoic aldehyde, and in 1867 Lauth and Grimaux
showed that the same compound could be formed by oxidizing benzyl chloride
in the presence of water. It was but a step from the laboratory into the
factory in this case, and at the present time the aldehyde is made on a
large scale by chlorinating boiling toluene beyond the stage of benzyl
chloride, and heating the mixture of benzal chloride and benzotrichloride
with lime and water under pressure. By this means the first compound is
transformed into benzoic aldehyde, and the second into benzoic acid. This
last substance is also required by the colour-maker, as it is used in the
manufacture of blue by the action of aniline on rosaniline; without some
such organic acid the transformation of rosaniline into the blue is very
imperfect.
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