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Picoline refers to three different methylpyridine isomers, all with the
chemical formula C6H7N and a molar mass of 93.13 g mol−1. All three are
colourless liquids at room temperature and pressure.
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2- and
4-picoline are produced in gas phase reactions at temperatures of about
400C from acetaldehyde and ammonia with the use of solid bed or fluid
bed catalyst on the basis of aluminium silicate.
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The
high purity alpha or gamma isomer is recovered as a reffinate or extract
product, respectively.
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3-Alkylated pyridines such as 3-picoline, 3(5)-ethyl pyridine and
2-methyl-5-ethyl-pyridine (MEP) are the natural choice as starting
materials for the nicotinates.
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Pyridine bases such as 3-picoline and MEP are predominantly manufactured
by the Chichibabin reaction, where a mixture of aldehydes or ketones is
reacted with ammonia.
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3-picoline is the ideal starting-material for nicotinic acid or amide:
the methyl group can be selectively and readily oxidised to the carboxyl
derivative with few by-products or pollutants.
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High
selectivity coupled with the low molecular weight ratio (1:1.3) compared
to the end-products make picoline an attractive industrial
starting-material for the production of nicotinic derivatives.
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The
bulk of picoline is produced today by the condensation of acetaldehyde,
formaldehyde and ammonia in the gas-phase, which simultaneously produces
large quantities of pyridine. A selective and suitable alternative
method starting from these or similar simple molecules has yet to be
developed.
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