Chemistry Reference
In-Depth Information
AROMATIC ORGANIC CHEMISTRY
P
HENOLS
Aromatic rings with attached hydroxyl groups are called phenols.
CH
3
CH
CH
3
OH
O
+
O
2
+
CH
3
CCH
3
isopropylbenzene,
hydroxybenzene,
acetone
cumene
phenol
OH
OH
OH
OH
OH
OH
1,2-dihydroxybenzene,
1,3-dihydroxybenzene,
hydroquinone
catechol
resorcinol
Phenol was originally recovered during the
coking
of coal, essentially being
a by-product. Eventually, commercial routes were developed based on ben-
zene (from coal or petroleum); for example,
sulfonation
of benzene to ben-
zenesulfonic acid followed by reaction with water to phenol plus regenerated
sulfuric acid. Phenol is used to make plastics (phenol-formaldehyde and
epoxy resins) and textile fibers (nylon). Phenol is also used in solution as a
general disinfectant for cleaning toilets, stables, floors, drains, etc. and is
used both internally and externally as a disinfectant for animals.
Catechol is also obtained from coal coking and from certain wood resi-
dues. Vanillin (synthetic vanilla flavoring) is a catechol derivative. Resorcinol
and hydroquinone are currently made by the same type of chemistry used
