History and Discovery
It was first extracted from the distillation products of coal tar in 1826 by Otto Unverdorben and Friedlieb Runge in Germany. They were the first to isolate it and recognize it as a unique chemical substance. However, it was William Henry Perkin, an English chemist, who was first to synthesize it artificially in 1856 while trying to synthesize quinine. Perkin noticed that the product he obtained was not quinine but had a beautiful purple color which led to the discovery of the first synthetic dye, mauveine. This kickstarted the synthetic dye industry and established it as an important industrial chemical.
Manufacturing
It is commercially produced by the alkylation of benzene with ammonia in the presence of a catalyst. In this process, benzene reacts with ammonia at high temperatures and pressures to produce cyclohexylamine. Cyclohexylamine is then oxidized to form Aniline. This reaction involves several intermediate steps and produces by-products like biphenyl, azobenzene, and diphenylamine. It is purified through distillation. Major manufacturing companies include BASF, Bayer, Tosoh, Huntsman, CNPC, Sinopec, and Mitsubishi Gas Chemical. Global production of it is estimated to be over 5 million tons per year.
Applications and Uses
Given its reactivity, it finds application across many industries and is used to synthesize numerous chemicals and products. In the dye industry, it is used to manufacture azo dyes, which impart different colors to materials like leather, wood, paper, and textiles. It is also used to make rubber processing chemicals and polyurethane chemicals required in industries like construction, furniture, etc. Aniline is a key intermediate in the production of MDI, a crucial component of rigid and flexible foams used for insulation. It is also utilized to synthesize agricultural chemicals like weedicides, fungicides, and insecticides. Other major end-use sectors include pharmaceuticals, refrigerants, explosives, and specialty chemical manufacturing.
Properties
It is a colorless, oily liquid with an aromaticamine odor. It is soluble in water, ethanol, ether, and acetone. It has a aromatic amine functional group (-NH2) which makes it highly reactive. It undergoes electrophilic substitution reactions and acts as a nucleophile. It readily undergoes oxidation, reduction, acylation, alkylation, and diazotization reactions. Aniline's combustion gives off toxic fumes of nitrogen oxides. It is moderately toxic to humans through oral ingestion, skin absorption, or inhalation. Prolonged exposure may damage liver, kidneys, and blood cells. Hence, proper protective equipment is needed while handling it.
Future Prospects and New Applications
Though it has been produced commercially for over a century, research into new applications and derivatives continue. Areas like pharmaceuticals, agrochemicals, specialty chemicals see growing demand. New aniline-based polymers that can replace plastics are being developed. Biotechnology methods are explored for its biosynthesis from renewable feedstocks. It will remain an essential building block chemical. With availability of new cost-effective production routes, aniline application scope would further expand in materials, coatings and green technology domains in the coming decades. Continuous R&D on safety aspects will also aid it to sustain its leadership position across manufacturing industries globally.
It occupies a unique historical position as one of the earliest synthetic industrial chemicals obtained from coal tar. Over the decades, it has developed into a major petrochemical widely used across dye, rubber, agrochemical and polymer sectors. Continuous process innovations coupled with focus on new downstream derivatives have ensured sustained growth of the global . Judicious application along with safety measures will help establish it as a dependable organic chemical for diversified manufacturing needs in the future as well.
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