Suberic acid is the trivial name for the compound octanedioic acid,
H H H H H H
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O H H H H H H O
The compound is a diacid, which means that it can donate two
protons. To be precise, suberic acid belongs to the
polycarboxylic acids because of the two carboxyl
groups (-CO2H) at the ends. It is a white,
fatty, crystalline substance.
The name of this compound is derived from the Latin suber,
Cork tree. The oxidation of cork with nitric acid results in a
mixture of acids by the name cerinic acid. From this mixture, Luigi
Valentino Brugnatelli, a 18th century chemist first isolated suberic
acid. In the 19th century, suberic acid was mainly produced by synthesis
from castor oil.
Suberic acid is mainly used in alkyd resins;
coatings and paints. Another application is the
synthesis of certain plastics, particularly certain types of
nylon. Because of its bifunctionality, suberic acid can
easily polymerize with a difunctional alcohol, or (in the case of nylon)
a diamine; a condensation polymerization.
x HO2C(CH2)6CO2H + x H2N(CH2)6NH2 -> -[C(CH2)6C-NH(CH2)6NH-]x- + x H2O
R.J. Fessenden and J.S. Fessenden, Organic Chemistry, 4th edition (1990), Brooks/Cole Publishing Company.