Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups.

In
molecular formulae for dicarboxylic acids, these groups are sometimes written as HO 2C-R-CO2H.
Dicarboxylic acids include two amino acids and are important. They are used to
prepare copolymers such as polyamides and polyesters.[1] In general, dicarboxylic acids show similar
chemical behaviour and reactivity as monocarboxylic acids. The ionization of the second carboxyl
group occurs less readily than the first.

Adipic acid (n=4) : Despite its name (in Latin adipis is fat), this acid (hexanedioic acid) is not
a normal constituent of natural lipids but is a product of oxidative rancidity (lipid peroxidation). It
was obtained [2] by oxidation of castor oil with nitric acid (splitting of the carbon chain close to the
OH group). Synthesized in 1902 from tetramethylene bromide, it is now obtained by oxidation
of cyclohexanol or cyclohexane. It has several industrial uses in the production
of adhesives,plasticizers, gelatinizing agents, hydraulic fluids, lubricants, emollients, as an
additive in the manufacture of some form of nylon (nylon-6,6), polyurethane foams, leather
tanning, urethane and also as an acidulant in foods. Adipic acid is used after esterification with
various groups such as dicapryl, di(ethylhexyl), diisobutyl, and diisodecyl.

Scheme 1. Synthesis of adipic acid

The oxidation of an alkene is an example of an addition reaction. Oxygen atoms in

the oxidizing
agent add to the carbon-carbon double bond. As a result, the ring opens and the
dicarboxylic
acid is formed. Several oxidants have been shown to accomplish this transformation
efficiently,
and the reagent of choice for this lab is potassium permanganate, KMnO4. The
mechanism for
the reaction is shown in Scheme 2. Notice that this reaction produces the syn-1,2diol and that
three equivalents of cyclohexene consume 4 equivalents of KMnO4. Under the
conditions that
we will use, another two equivalents of KMnO4 are consumed in the oxidation of the
diol to the
dialdehyde, and another two in the oxidation to the diacid. Overall, the conversion
of 3 moles of
cyclohexene to 3 moles of adipic acid consumes 8 moles of KMnO4

The acid is actually produced as a water-soluble potassium salt. The first step of the
work-up is
to wash the aqueous reaction mixture with an organic solvent to remove any nonacidic byproducts or intermediates. We then acidify the aqueous layer to protonate
the acid. Adipic acid

should precipitate at this stage. Keeping your aqueous volume to a minimum is

critical because
the solubility of adipic acid in water is 1.8 % by weight at room temperature.