1) Paranitroanilin

A mixture of 13.8 grams (0.1 mole) of p-nitroaniline, 30 cc. water, and 30 cc. concentrated hydrochloric
acid, is heated until solution is complete. The solution is cooled to room temperature with shaking under
the tap, 80 grams of ice is added, and then an amount of dry, powdered sodium nitrite equivalent to 6.9
grams of pure NaNO2 is added in one portion with constant shaking. Shaking is continued until most of
the precipitated material has redissolved, and the mixture is allowed to stand for about 10 minutes in ice
and is then tested with Congo red paper and sulfone reagent. Any residual undissolved material is
removed by filtration. The residue should be very small; the filtrate should be clear and almost colorless
and no cloudiness should reappear. The final diazo solution is relatively stable in the dark but is very
sensitive to light.

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Since p-nitroaniline does not form water stable salts, the base must be obtained in a highly divided state
before the diazotization reaction. A clear solution of 13.8 grams (0.1 mole) of technical p-nitroaniline in
30 cc. concentrated hydrochloric acid and 30 cc. water at 80-90°C. is added with good stirring to a mixture
of 50 cc. water and 50 grams of finely crushed ice. The temperature of the final mixture is about 8°. A 20
per cent solution containing 7 grams of sodium nitrite is then added in one portion with vigorous stirring.
The temperature rises to 15° and the solution becomes clear in a few seconds. The usual tests with Congo
red and starch-iodide are made. In large scale diazotizations, the nitrite solution should be added very
rapidly below the surface of the liquid in order to prevent the formation of large amounts of the
diazoamino compound.

2) 2-Naftolamin-1-Asam Sulfonat

In a 1-liter, five-necked flask, fitted with a stirrer, preferably of the paddle type, operating through a
mercury seal in the center neck, a dropping funnel, a thermometer, a gas inlet tube, and a gas outlet tube,
72 grams (0.5 mole) of dry β-naphthol is treated with 280 grams of hot (100°C.) completely dry
nitrobenzene. (The simplest method for drying nitrobenzene is to distill and discard the first fraction which
contains all of the water.) The resulting completely clear solution is allowed to cool with stirring, part of
the naphthol crystallizing out. The mixture is cooled in ice, and 35 cc. (62 grams) sulfuric acid-free
chlorosulfonic acid is dropped in slowly, while the temperature is kept below 5°. The hydrogen chloride
which is formed is passed through a calcium chloride tube into a suitable absorption apparatus. The β-
naphthol goes into solution rapidly, and toward the end of the reaction part of the naphtholsulfonic acid
precipitates. When all of the chlorosulfonic acid has been added, the remaining dissolved HCl is swept out
by means of a stream of dry air.
Diazotasi Kopling Salting Out

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