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BAB 1

PENDAHULUAN
1.1.

DASAR TEORI
Pembuatan Orange II dilakukan melalui 2 tahap yaitu raksi diazotasi kemudian

dilanjutkan dengan reaksi coupling. Pada reaksi diazotasi ini ada beberapa syarat yaitu bahan
dasar harus amina aromatis primer, reaksi harus pada suhu rendh yaitu 0-5C, dan harus
dalam larutan asam kuat seperti HCl. Pada reaksi diazotasi ini akan terbentuk garam
diazonium dengan amina aromatis dan asam nitrit.
Orange II termasuk ke dalam zat warna asam (anionik). Zat warna asam biasanya
terdiri atas gugus SO3H atau gugus COOH yang membentuk garam dengan basa. Zat warna
ini kurang larut dalam alkohol dibandingkan zat warna basa dan zat warna ini tidak larut
dalam minyak dan lemak. Orange II juga termasuk zat warna dengan nama lain 1-psulfobenzeneas-2 naphtol sodium salt.
Pada reaksi coupling prinsipnya adalah reaksi substitusi elektrofilik pada inti
aromatis. Garam diazonium berfungsi sebagai elektrofil. Syarat reaksi coupling suasananya
harus alkalis/ netral
Pewarna asam yang larut air pewarna digunakan terutama dalam bentuk garam
natrium atau karboksilat asam sulfanilat. Senyawa-senyawa tersebut merupakan anionik yang
menempel kuat kepada kelompok kationik dalam serat secara langsung yang dapat berlaku
untuk semua jenis serat alami seperti kapas dan sutra serta sintetis seperti poliester dan rayon.
Senyawa-senyawa itujuga digunakan dalam cat, tinta, tekstil dan kertas. Tidak digunakan
sebagai pewarna makanan karena bersifat karsinogenik.

1.2.

TUJUAN
Mampu menjelaskan prinsip reaksi pembentukan zat warna melalui reaksi diazotasi
dan reaksi coupling.
Mampu menjelaskan kerja NaCl sebagai salting out
Mampu menghasilkan zat warna yang mengkilap

BAB II
METODE KERJA
2.1.
Prosedur
1. Diazotation
In a 125 ml Erlenmeyer flask dissolve 4,8 g of sulfanilic acid crystals in 50 ml
of 2,5 % sodium bicarbonate 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 glass 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
material is then ready to use. The produst is 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-sulfobenzeneas-2 naphtol sodium salt)
In a 400 ml beaker glass dissolve 3,6 g of naphthol 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 an
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 minutes.,
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 coloured mother
liquor. The filtration is somewhat slow.
The products dries only slowly and it contains about 20 % of sodium chloride.
The crude yield is thus not significant and the materials need not to be dried before
being purified. This azo dye is too soluble to be crystallized from water; it can be
obtained in a fairly satisfactory form 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 50 ml). Filter by suction through a Buchner funnel that has been
preheat 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 yirld of pure crystalline material 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.
2.2 ALAT DAN BAHAN
Alat :
1. Kasa asbes
2. Kaki tiga
3. Api Bunsen
4. Erlenmeyer 250 ml
5. Beker glass
6. Labu hisap
7. Gelas ukur
8. Corong Buchner
9. Pengaduk
10. Pipet
11. Gelas arloji
12. Corong kaca
Bahan :
1. Asam sulfanilat
2. Na2CO3
3. NaNO2
4. HCl pekat
5. -naftol
6. NaOH
7. NaCl
8. Etanol
2.3 SKEMA KERJA

4,8 gram
1,22 gram
1,9 gram
5 ml
3,6 gram
2 gram
10 gram
100-125 ml

4,8 g asam sulfanilat + 1,33 g Na2CO3 dalam 50 ml air

Panaskan ad larut, dinginkan +1,9 g NaNO2


Tuang dalam beker glass berisi 25 g es batu + 5 ml HCl pekat, aduk-aduk

+3,6g -naftol + 20 ml NaOH 10% dingin, aduk, panaskan ad larut


1,33 gram Na2CO3

4,8 gram asam sulfanilat

50 ml aquadest
didinginkan dengan air kran

+NaCl 10 g, didinginkan. Saring dengan corong Buchner, cuci dengan NaCl jenuh
didihkan

larutan dalam erlenmeyer dituang


ke beaker

Rekristalisasi
dengan
pelarut air
25 gram es
5 ml HCl pekat

1,9 gram NaNO2


aduk ad larut

Saring panas, uapkan ad 15 ml, didinginkan ad 80C


3,6 gram -naftol
terbentuk endapan putih garam
diazonium
yang
memisah
(suspensi 1)

20 ml larutan NaOH 10%

beaker glass baru

suspensi 1 dituang sambil diaduk


selama 5-10 menit

+etanol 100-125 ml. Didinginkan


10 gram NaCl

Saring dengan corong Buchner, cuci dengan etanol air

beaker diletakkan dalam wadah


berisi es dan air sambil diaduk
sampai mendingin sekuruhnya

dipanaskan ad larut

dipanaskan sambil diaduk

Keringkan dalam eksikator


hasil penyaringan

dipanaskan
sampai
larut,
disaring panas

air mendidih

2.4 disaring,
GAMBAR
PEMASANGAN ALAT
sisanya dicuci dengan sedikit
larutan jenuh NaCl

didinginkan
warna

sampai

terbentuk

zat

etanol 100-125 ml

didinginkan
80oC

sampai

dikeringkan, lalu ditimbang

disaring dengan corong Buchner,


dicuci dengan sedikit etanol

jika volume lebih dari 60 ml


maka diuapkan dahulu

NH3+
SO3-

NH2

2.5 MEKANISME REAKSI


NH2 2.5.1.1 Reaksi diazotasi
SO3H

SO3Na
NH3+

Internal neutralization

SO3-

+ Na2CO3

+ CO2 + H2O

NH2+ ClSO3Na
NH2
SO3Na

+ HCl p

+ HNO2

2.5.1.2 Reaksi coupling


OH

naftol

O NA

+ NaOH

N = N+Cl-

O-

+ H2O

O NaO3S

N=N

OH
NaO3S

N=N

Orange II = 1-p-sulfobenzena azo-2-naftol sodium salt

BAB III
PEMBAHASAN
Orange II dibuat melalui reaksi diazotasi dan coupling.