A synthesis of pseudo-mauveine and a homologue

Treatment of N-phenyl-p-phenylenediamine and two equivalents of aniline with potassium dichromate in hot water acidified with a small amount of sulfuric acid gives 3-phenylamino-5-phenyl-7-aminophenazinium sulfate (pseudo-mauveine). The oxidation of N-phenyl-p-phenylenediamine and o-toluidine with p...

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Bibliographic Details
Published inJournal of chemical research Vol. 35; no. 5; pp. 304 - 309
Main Author Plater, M. John
Format Journal Article
LanguageEnglish
Published ST ALBANS Science Reviews 2000 Ltd 01.05.2011
Sage Publications Ltd
Subjects
Aniline
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
mauveine
aniline purple
coal tar dyes
mauve
pseudo-mauveine
ANILINE
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Summary:Treatment of N-phenyl-p-phenylenediamine and two equivalents of aniline with potassium dichromate in hot water acidified with a small amount of sulfuric acid gives 3-phenylamino-5-phenyl-7-aminophenazinium sulfate (pseudo-mauveine). The oxidation of N-phenyl-p-phenylenediamine and o-toluidine with potassium dichromate in water with a small amount of sulfuric acid gives 3-phenylamino-5-(o-toluyl)-7-amino-8-methylphenazinium sulfate. Oxidation of aniline and (o or p) toluidine only gave small quantities of mauveine chromophores. Oxidation of p-toluidine gives a known dimer which gives a purple coloured solution in acid. A hypothesis is described in which N-phenyl-p-phenylenediamine may have been involved in mauveine synthesis in the nineteenth century.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
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ISSN:1747-5198
2047-6507
DOI:10.3184/174751911X13052165053977