In the apparatus for steam distillation, the greater portion
of the condensation is effected by the stream of water passing
over the receiver. It is, therefore, necessary that the stream
passing through the condenser should be sufficiently rapid to cause
it to form a uniform film over the receiving flask. A 12-l. flask
is even more efficient as a condenser than the 5-l. flask. It is
important that the tube through which the vapors leave the distillation
flask should be neither too short nor, especially, too narrow.
Where the external diameter of the steam inlet tube is 5-8 mm.,
the internal diameter of this steam head should be not less than 28 mm.
Were it less, the current of steam passing through it would be so rapid
as to prevent small quantities of liquid from returning to the flask,
and these would be driven over into the receiver.
Much time can be saved by the use of the steam distillation apparatus
described, especially when large quantities have to be handled.
The above directions avoid the use of extraction methods, which not
only consume more time but may lead to appreciable losses of material.
If the downward condenser is of iron, the apparatus is even more
efficient and the time for the steam distillation is halved.
The percentage yields have been based on the amount of aniline taken.
It would probably be more legitimate to base the calculation on the amounts
of aniline taken and of nitrobenzene not recovered, since undoubtedly
the latter is reduced to aniline during the course of the reaction.
If this be done, the yield is found to be only 55 to 60 per cent
of the calculated amount.
In a number of experiments, the glycerol used contained an appreciable
amount of water. Under these conditions, the yield of product
is much lower. "Dynamite" glycerol containing less than half a per
cent of water is best employed; U. S. P. glycerol contains 5 per
cent of water and usually gives lower yields.
3. Other Methods of Preparation
Quinoline has been produced by passing the vapor of allylaniline
over red-hot lead oxide;[1a] by heating acrylideneaniline, or better,
a mixture of aniline, glycerol and sulfuric acid;[2a] by heating
aniline with glycerol and sulfuric acid, using nitrobenzene as an
oxidizing agent;[1] by treating a mixture of glyoxal and _o_-toluidine
with alkali;[2] by treating a solution of _o_-aminobenzaldehyde with
acetaldehyde and alkali;[3] by heating methylacetanilide with zinc
chloride;[4] by heating aminoazobenzene with glycerol and sulfuric
acid;[5] by heating a mixture of aniline, glycerol and sulfuric
acid with arsenic acid.[6]
[1a] Ber. 12, 453 (1879).
[2a] Ber. 13, 911 (1880); Monatsh. 1, 316 (1880).
[1] Monatsh. 2, 141 (1881); J. prakt. Chem. (2) 49, 549 (1894),
[2] Monatsh. 15, 277 (1894).
[3] Ber. 15, 2574 (1882); 16, 1833 (1883).
[4] Ber. 23, 1903 (1890).
[5] Ber. 24, 2623 (1891)
[6] Ber. 29, 704 (1896)
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