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- W137846510 abstract "N-oxides were defined, their history and chemistrysurveyed. Conventional N-oxidising reagents, such as thealiphatic and aromatic percarboxylic acids were examined.Immobilized catalysts, their applications and synthesiswere extensively reviewed and examples noted. Immobilizedpercarboxylic acids or carboxylic acids in conjunction with hydrogen peroxide were identified as potential N-oxidising reagents. The literature survey yielded eight routes which have been utilized for introduction of a carboxyl group into polystyrene. A number of these routes wereinvestigated experimentally. Two routes proved useful,(i) modification of Merrifield resin to carboxylated resinand (ii) chloroacylation of polystyrene , then formation ofthe phenyl pyridinium chloride derivative followed bycleavage afforded carboxylated polystyrene.The criteria for a useful support resin were reviewed and aporous macroreticular polystyrene-divinylbenzenecrosslinked resin was found to offer a number of advantagesover convensional gel-type resins. A sample of such aresin, XE-305 was procured from a commercial company andused for synthesis. The carboxylated derivative withcarboxylate loading from 42% to 88% were used to oxidise2-chloropyndine to its N-oxide in the presence of excesshydrogen peroxide and mineral acid. Yields of the order of33-35% were achieved. 2-Chloropyridine-N-oxide is used forthe manufacture of a number of commercially importantantifungal and anti- bacterial biocides.Despite numerous changes and modifications to the reactionconditions, including the use of a peroxide stabiliser, theyield could not be increased above 33-35%. For commercialsuccess, yields greater than 60% would have to be achievedinorder to compete with existing processes such as theperacetic acid process reported in the literature. A massbalance examination showed that up to 24% of the initial2-chloropyridine was unaccounted for at the end ofoxidation. A further study of 2-chloropyndine and itsN-oxide stability, demonstrated that product N-oxide andnot 2-chloropyridine was unstable and decomposed underconditions likely to prevail m the oxidations. No way wasfound to prevent this decomposition and so it wasconcluded that this process using immobilized catalystcould not compete with existing batch processes utilisingperacetic or acetic acid/hydrogen peroxide." @default.
- W137846510 created "2016-06-24" @default.
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- W137846510 date "1994-01-01" @default.
- W137846510 modified "2023-09-27" @default.
- W137846510 title "SYNTHESIS AND USE OF AN IMMOBILIZED CATALYST FOR THE N-OXIDATION OF 2-CHLOROPYRIDINE" @default.
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- W137846510 hasPublicationYear "1994" @default.
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