P-Toluic Acid on:
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''p''-Toluic acid (4-methylbenzoic acid) is a substituted
benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, wh ...
with the formula CH3C6H4CO2H. It is a white solid that is poorly soluble in water but soluble in acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
. A laboratory route to ''p''-toluic acid involves oxidation of p-cymene
''p''-Cymene is a naturally occurring aromatic organic compound. It is classified as an alkylbenzene related to a monoterpene. Its structure consists of a benzene ring ''para''-substituted with a methyl group and an isopropyl group. ''p''-Cym ...
with nitric acid.
Role in production of terephthalic acid
''p''-Toluic acid is an intermediate in the conversion of ''p''-xylene toterephthalic acid
Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tonnes are produced annua ...
, a commodity chemical used in the manufacture of polyethylene terephthalate
Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods ...
. It is generated both by the oxidation of ''p''-xylene as well as the hydrogenolysis
Hydrogenolysis is a chemical reaction whereby a carbon–carbon or carbon–heteroatom single bond is cleaved or undergoes lysis (breakdown) by hydrogen.Ralph Connor, Homer Adkins. Hydrogenolysis Of Oxygenated Organic Compounds. J. Am. Chem. Soc. ...
of 4-carboxybenzaldehyde. In related processes it is converted to methyl p-toluate, which is oxidized to monomethyl terephthalate.
See also
* ''o''-Toluic acid * ''m''-Toluic acidReferences
{{DEFAULTSORT:Toluic acid, p- Benzoic acids External linksMaterial Safety Data Sheet