I.

PROSEDUR
1. Diazolization
In a 125 ml erlenmeye flask dissolve 4,8 g of sulfanilic acid crystals
(monohydrate) in 50 ml of 2,5% sodium carbonate solution (or use 1,33 g of
anhydrous sodium carbonate and 50 ml of water) by boiling. Cool the solution
under the tap, add 1,9 g of sodium nitrite and stir until it is dissolved. Pour the
solution into a beaker or flask containing about 25 g of ice and 5 ml of
concentrated hydrochloric acid. In a minute or two a powdery white precipitate of
the diazonium salt should separate and the materials is then ready for use. The
product not collected but is used as the suspension. It is more stable than most
diazonium salts, and it will keep for a few hours.
2. Orange II (1-p-Sulfobenzena azo-2-naphtol sodium salt)
In a 400 ml beaker dissolve 3,6 g of -naphtol in 20 ml of cold 10% sodium
hydroxide solution and pour into this solution with stirring the suspension of
diazotized sulfanilic acid (rinse). Coupling occurs very rapidly and the dye, being a
sodium salt separates easily from the solution on a account of the presence of a
considerable excess of sodium ion (from the soda, the nitrite, and the alkali added).
Stir the crystalline paste throughly to effect good mixing and after 5-10 minute .
Heat the mixture until the solid is dissolved. Add 10 g of sodium chloride to further
decrease the solubility of the product, bring this all into solution by heating and
strirring. Set the beaker in a pan of ice and water, and let the solution cool
undisturbed. Eventually cool throughly by stirring and collect the product on a
Buchner funnel. Use saturated sodium chloride solution rather than water for
rinsing the material out of the beaker and for washing the filter cake free from the
dark colored mother liquor. The filtration is somewhat slow. This gives a more
easily filterable product. If time permits it is still better to allow the solution to cool
at room temperature.
If the filtration must be interrupted close the rubber suction tubing (while
the pump is still running) with a screw pinch clamp placed close to the filter flask
and then disconnect the tubing from the pump. Fill the funnel and set the unit aside,
suction will maintained and filtration will continue.
The product dries only slowly and it contains about 20% of sodium
chloride. The crude yield is thus not significant and the material need not be dried
before being purified. This azo dye is too soluble to be crystallized from water. It
can be obtained in a fairly satisfactory from by adding saturated sodium chloride
1

solution to a hot, filtered solution in waterr and cooling, but the best crystals are
obtained from aqueous ethanol. Transfer the filter cake to a beaker, wash the
material from the paper and funnel with water, and bring the substance into
solution at the boiling point. Avoid a large excess of water, but use enough to
prevent separation of solid during filtration (volume about 50 ml). Filter by suction
through a Buchner funnel thas has been preheated on the steam-bath. Pour the
filtrate into a erlenmeyer flask (wash), estimate the volume and if this is greater
than 60 ml, evaporate by boiling. Cool to 80 add 100-125 ml of alcohol and allow
crystallization to proceed. Cool well before collecting. Rinse the beaker with
mother liquor and wash finally with a little alcohol. The yield of pure, crystalline
material is 6-8 g. Orange II separates from aqueous alcohol with two molecules of
water of crystallization and allowance for this should be made in calculation of the
yield. When the water of hydration is eliminated by drying at 120 the material
becomes fiery red.