Oxidation of Cyclohexene to Adipic Acid

Mitchell, Jerome

Lab Partner: Atri, Jyotsna

CHM0206-Organic Chemistry II – Section 10157

Dr. Saphronia R. Wallace

August 8, 2011

The purpose of this experiment was to perform an oxidation reaction.   The oxidation reaction used was the synthesis of adipic acid from cyclohexene.   The percent yield of 53.12% adipic acid, suggests that several factors may have affected the outcome not to yield at 100% adipic acid. Even though the percent yield was low, the melting point test of the sample was 154-158°C, which was close to the literature value of 152.1°C.
Adipic acid is used to manufacture nylon and polyurethane foams.   Nylon and polyurethane are used in the make-up of medical equipment, parachutes, machine screws, clothing used from thermal insulation to sound proofing of rooms.4
Adipic acid is a white crystalline solid used primarily in the manufacture of nylon 6, 6 polymers for fibers and plastics. The largest global use of adipic acid (ADA) is in nylon 6, 6 production, which accounts for 73% of global output.  Nylon fiber accounts for 47% of the global market and nylon resin 26%. The non-nylon sector accounts for 27% of world demand, of which polyurethane (PU) is the largest. Smaller uses are in plasticizers, resins, coatings and polyamide 4,6.5  
In this experiment, adipic acid was synthesized in one step starting from cyclohexene by way of oxidation.   3 Cyclohexene + 8 KMnO4 + 4 H2O yields 3 Adipic Acid + 8 KOH + 8 MnO2 as the complete balanced equation for the experiment.   Oxidative cleavage is a known process in which the bonds of carbon atoms are broken.   During the experiment, cyclohexene was oxidized by using potassium permanganate.   The oxygen atoms in the KMnO4 are added to the carbon – carbon double bonds and dicarboxylic acid was formed.   The heated reaction mixture coagulated the manganese dioxide that was removed through filtration over a vacuum.   As a qualitative...

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