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Preparation of Sulphanilic acid

It comprises of three steps as follows: 1- Preparation of Nitrobenzene from benzene 2- Preparation of Aniline from Nitrobenzene 3- Preparation of Sulphanilic acid from Aniline

1- Preparation of Nitrobenzene:
Aromatic hydrocarbons may be nitrated with concentrated nitric acid in the presence of concentrated sulphuric acid (mixed acid reagent). It is carried out at low temperature (at 50oC), otherwise polynitration or oxidative breakdown may likely to occur. a) Equation:

b) Reagents: Conc. HNO3 Conc. H2SO4 Benzene Ahydrous CaCl2 c) iiiiii50g (35ml, 0.5mol) 74g (40ml) 26g (30ml, 0.33mol) 5g

Procedure: Take H2SO4 and HNO3 in a flask and keep the solution cool in cold water. Add C6H6 in portion wise such that temperature does not rise 55oC. Flux the solution for 40-45min at 60oC. Pour solution in cold water into a beaker to wash acid and allow this solution to stand. iv- Extract two time with 50ml water. Take lower layer in a conical flask. Put CaCl2 in conical flask. Shake vigorously. v- Heat solution and filter it after cooling. vi- Take filtrate in distilling flask. Heat solution such that temperature does not rise 214oC. vii- Yield is 85% (35g).

2- Preparation of Aniline:
Primary arylamines are generally prepared by reduction of nitro compounds. Tin and hydrochloric acid may be employed. When reduction is complete a complex amine chlorostannate may separate from which the amine is liberated by basification, using enough alkali to dissolve the tin hydroxide formed during reduction. a) Equation:

b) Reagents: Nitrobenzene Granulated tin (Sn) HCl NaOH H2O Commercial salt Ether K2Cr2O7 25g (21ml, 0.25ml) 45g (0.38ml) 100ml 75g 125ml 20g for 100ml liquid 40ml Few grams

c) Procedure: i- Place nitrobenzene and tin in a round bottomed flask equipped with reflux condenser. ii- Add 100ml HNO3 portion wise and 15ml each in reaction mixture. iii- Add HNO3 cautiously with well stirring because reaction is exothermic. Cool the reaction mixture of necessary. Proceed in this way that all the HNO3 is added. iv- Finally heat solution on water bath for 30-60min i.e. until odour of nitrobenzene is not perceptible and few drops of reaction mixture give clear solution with water. v- During cooling may white or yellow crystals of aniline chlorostannate separates. vi- Add aqueous solution of NaOH in cold reaction mixture. If liquid boil cool it.The hydroxide of tin precipitated. Aniline separates as oil. vii- Take aniline in separatory funnel. Add commercial salt and ether. Shake the solution well and allowed to stand. viii- Separate lower aqueous layer and extract further with ether. ix- Dry ethereal solution with anhydrous K2CO3 and shake for several minutes. x- Filter ethereal solution and remove ether by flash distillation. xi- Yield is 97% (18g).

3- Preparation of Sulphanilic acid: Arylamine can be sulphonated with concentrated suphuric acid by heating upto 180oC. a) Equation:

b) Reagents: Aniline Con. H2SO4 NaOH (2M) Water Decolourizing carbon

20.4g (20ml, 0.22mol) 74g (90ml) 3.4ml 400g 4g

c) Procedure: i- Place aniline in flask, add conc. H2SO4 in portion cautiously. Immerse the sol flask in cold water to keep it cool during addition. ii- Heat the solution on a water bath at 180-190oC for 5 hours. iii- Test solution by taking a few drops of reaction mixture in 2M NaOH solution, if resulting mixture is cloudy then reaction is complete. iv- Pour the solution in 400g cold water. Allow to stand for 10 minute. Filter and wash with water. Decolourize with 4g decolourizing carbon if necessary. v- Dry between sheets of filter paper or in desiccator containing anhydrous CaCl2. vi- Yield is 52-58% (20-22g).

PRACTICALS
Superwiser: Submitted by: Prof. Muzzafar Ghumman Muhammad Usman 10120606-018 BS Chemistry 7th Semester

Department of Chemistry

Govt. Murray College Sialkot.

Date: 30/03/2014