Laboratory Preparation of Aniline, Chemical reactions, and Its Uses

Table of Contents

Laboratory Preparation of aniline, chemical reactions, and its uses in organic chemistry have been discussed here:

Principle involved in laboratory preparation of Aniline

Aniline is prepared in the laboratory by the reduction of nitrobenzene with tin (Sn) and Concentrated hydrochloric acid (HCl).

Aniline, preparation of aniline, preparation of aniline from nitrobenzene

The following reactions are involved in the preparation of aniline.

Aniline, preparation of aniline, preparation of aniline from nitrobenzene

Procedure for the laboratory preparation of Aniline

In a 250 mL round bottom flask fitted with a reflux condenser, 20 mL nitrobenzene and 40 gm granulated tin are added. 50 mL of Conc. HCl is added slowly with constant shaking. The round bottom flask is cooled after each addition so that the temperature does not exceed 60°C. The reaction mixture is then heated for approximately an hour in a boiling water bath until the oily droplets of nitrobenzene disappeared. After cooling the flask, a crystalline solid mass known as phenyl ammonium chloro stannate is separated. The impure alkaline as a dark brown oil is then obtained by treating the crystalline solid mass with Conc. NaOH.

laboratory preparation of aniline, preparation of aniline

Purification of Aniline

The mixture obtained is then subjected to the process of steam distillation to separate aniline. Distillate that contains a mixture of aniline and water is extracted several times with ether. Aniline thus obtained is redistilled at 182-1850C to obtain pure and dry aniline.

steam distillation of aniline, preparation of aniline

Chemical Reactions of Aniline

preparation of acetanilide from aniline reaction

In reaction with an acid chloride or acid anhydride, aniline gives N-acyl product in presence of a catalyst.

preparation of acetanilide from aniline, acetanilide, acetanilide preparation

preparation of 2, 4, 6-tribromoaniline from aniline

Aniline reacts with aqueous Br2 to give a white precipitate of 2,4,6-tribromoaniline.

preparation of 2, 4, 6-tribromoaniline from aniline

preparation of diazonium salt from aniline

In reaction with nitrous acid (NaNO2 + HCl) in cold conditions, aniline gives benzene diazonium salt.

preparation of diazonium salt from aniline, Benzene diazonium chloride from benzene

preparation of phenol from aniline

Benzene diazonium salt formed from the reaction of aniline with nitrous acid (NaNO2 + HCl) in cold conditions when is hydrolyzed, then phenol is obtained.

preparation of phenol from aniline

preparation of sulfanilic acid from aniline

When aniline is heated with fuming sulphuric acid, sulfanilic acid, or p-aminobenzenesulphonic acid is obtained.

preparation of sulphanilic acid from aniline

preparation of azo dye from aniline

Aniline when coupled with a benzene diazonium salt, it gives p-aminobenzene (orange-red dye).

preparation of p-aminobenzene, preparation of azo dye from aniline

preparation of 2-naphthol aniline dye

Benzene diazonium salt when treated with 2-naphthol in presence of dilute NaOH at pH 9-10 yields 2-naphthol aniline.

preparation of 2-naphthol aniline dye

preparation of aniline from nitrobenzene

Aniline is prepared when nitrobenzene is reduced with tin (Sn) and Concentrated hydrochloric acid (HCl).

preparation of aniline from nitrobenzene

Uses of Aniline

  •  Uses as a pesticide and fungicides in the agricultural industry.
  • For the manufacture of dyes, sulpha drugs etc.
  • Used to determine the aromaticity of oil products.
  • For the manufacture of antioxidants and vulcanization accelerators in rubber and plastics industry.

Preparation of Aniline video

References

  • Morrison, R. T., & Boyd, R. N., Organic chemistry, Allyn and Bacon, Inc. 1987.
  • March, J., Advanced Organic Chemistry, Wiley Eastern Limited, 1986.
  • Bahl, B.S., A., Advanced Organic Chemistry, S. Chand and company Ltd, New Delhi, 1992.
  • Finar, I. L., Organic Chemistry, Vol. I and Vol. II, Prentice Hall, London, 1995.

laboratory preparation of aniline, preparation of aniline from nitrobenzene, uses of aniline

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