ORANGE II

A. Kepustakaan
1. Fieser LF, 1957, Experiments in organic chemistry, 3 th ed. D.C Health and
company, Boston, p.192-193
2. Fessenden RJ & Fesenden JS, 1994, Organic Chemistry, 5 th edition, Brooks/ cole
Publishing Company Pasific Grove, California, 515-516, 873-876.

B. Prosedur
Diazolization
In a 125 ml Erlenmeyer 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 dissolve. 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

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 account of the presence of a considerable excess of
sodium ion (from the soda, the nitrite, and the alkali added). Stir the crystalline paste
thoroughly to effect good mixing and after 5-10 min. 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 stirring. Set the beaker in a pan of ice and water,
and let the solution cool undisturbed. Eventually cool thoroughly 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.
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 solution to a hot, filtered solution in
water 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 50ml). Filter by
suction through a Buchner funnel that has been preheated on the steam bath. Pour the
filtrate into an 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.

C. Dasar Teori
D. Tujuan
1. Mampu memahami dan menjelaskan prinsip reaksi pembentukan zat warna
melalui reaksi diazotasi dan reaksi coupling.
2. Mampu memahami dan menjelaskan kerja NaCl sebagai salting out.
3. Mampu menghasilkan zat warna yang mengkilap.

E. Alat dan Bahan

Bahan :

Asam Sulfanilat

: 4,8 gram

Na2CO3 anhidrat

: 1,33 gram

Aquadest

: 50 ml

NaNO2

: 1,9 gram

Es

: 25 gram

HCl pekat

: 5 ml

-naftol

: 3,6 gram

Larutan NaOH 10%

: 20 ml

NaCl

: 10 gram

Etanol

: 100-125 ml

Alat :

a. Erlenmeyer

h. Pompa hisap

b. Pengaduk

i. Kertas perkamen

c. Beaker glass

j. Kertas saring

d. Gelas ukur

k. Sumbat gabus

e. Anak timbangan + pinset

l. Pipet tetes

f. Corong Buchner

m. Timbangan gram

g. Labu hisap

n. Penangas air + Bunsen

F. Mekanisme Reaksi

G. Cara Kerja
Diazotasi
1. Dilarutkan 4,8 gram asam sulfanilat dalam 50 ml larutan Na2CO3 2,5% dengan
pendidihan dalam labu erlenmeyer 125 ml (dengan menggunakan 1,33 gram
Na2CO3 anhidrat dan 50 ml aquadest).
2. Larutan tersebut didinginkan dengan air kran, ditambahkan 1,9 gram NaNO2,
diaduk sampai larut.
3. Larutan tersebut dituang ke dalam beker gelas yang berisi 25 gram es dan 5 ml
HCl pekat. Dalam 1-2 menit akan terbentuk endapan putih dari garam diazonium
yang akan memisah (suspensi I)
Coupling
1. Dalam beaker 400 ml, dilarutkan 3,6 gram -naftol dalam 20 ml larutan NaOH
10%. Lalu suspensi I dituang ke dalam larutan ini sambil diaduk.
2. Pasta yang terbentuk diaduk dengan rata untuk mendapatkan campuran yang baik.
3. Setelah 5-10 menit, campuran tersebut dipanaskan sampai bagian yang padat larut,
ditambahkan 10 gram NaCl untuk mengurangi kelarutan dari hasil yang diperoleh,
dipanaskan sambil diaduk. Kemudian beaker gelas dimasukkan ke dalam wadah

yang berisi es dan air, lalu dibiarkan sampai larutan mendingin seluruhnya sambil
diaduk rata.
4. Hasil yang diperoleh dipisahkan dengan corong Buchner. Sisanya dicuci dengan
larutan jenuh NaCl sedikit.
Rekristalisasi
1. Hasil yang diperoleh ditambah air mendidih, dipanaskan sampai larut, disaring
panas.
2. Bila volume zat lebih dari 60 ml, diuapkan dulu, kemudian dinginkan sampai
temperatur 80oC, lalu ditambah etanol 100-125ml.
3. Didinginkan pelan-pelan sampai terbentuk zat warna, disaring dengan corong
Buchner. Lalu dicuci dengan sedikit etanol.
4. Hasilnya dikeringkan lalu ditimbang.
H. Skema Kerja

I. Gambar Pemasangan Alat

didinginkan
warna

sampai

terbentuk zat

etanol 100-125 ml

didinginkan
80oC

sampai

dikeringkan, lalu ditimbang

disaring dengan corong Buchner,

dicuci dengan sedikit etanol

J.

Pembahasan dan Diskusi

jika volume lebih dari 60 ml

maka diuapkan dahulu