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General
Process
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Methylation of hindered phenols, aromatic amines and carboxylic
acids with dimethylcarbonate and a catalytic amount of DMAP is most
effective, and the by-products are carbon dioxide and methanol.
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A
typical manufacturing process for a hindered phenol antioxidant uses
a substituted cresol raw material for the phenolic ring portion of
the molecule, and an aldehyde raw material for the bridging or
connecting group. The batch reaction takes place in an alcoholic
solvent and utilizes an acid catalyst. When the reaction is
complete, the batch is quenched with water and decanted.
Purification steps may include additional water washes/decants
before the product is slurried with a hydrocarbon solvent, vacuum
filtered, washed with additional solvent, centrifuged and dried.
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Deactivated and sterically hindered phenols have been acetylated
with acetic anhydride under microwave
irradiation and using iodine as catalyst in an eco-friendly process.
Application
&Technology
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Hindered phenol antioxidants, which contain the
2,6-di-tert-butylphenol functional group, are very effective primary
antioxidants.
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The
Oxygen Induction Time (OIT) test is an accelerated aging test that
is often used to predict the long
term stability of hydrocarbon materials including plastics, rubbers,
and adhesives. The OIT can be Studied by Hindered Phenol Stabilizers
in Natural Rubber and Hot Melt Adhesives.
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The
effects of extracellular application of some sterically-hindered
phenols can be investigated using the patch-clamp technique.
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