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- Title
Uncovering John Holliday's industrial dye synthesis patented in 1865.
- Authors
Plater, Michael John; Harrison, William TA
- Abstract
Holliday's industrial dye synthesis of 1865 was repeated by heating aniline hydrochloride with nitrobenzene and the products were characterised by modern spectroscopic methods. A red dye was isolated in low yield and characterised by an X-ray single-crystal structure determination as 9-phenyl-3-anilinophenazone-2-anil. The structure was identical to that made 93 years later in 1958 by the oxidation of 2-aminodiphenylamine hydrochloride with FeCl3 followed by heating the two products with aniline. An X-ray single-crystal structure determination was obtained for an isomer of anilinoaposafranine. A proposal is made that 9-phenyl-3-anilinophenazone-2-anil, isolated from Holliday's synthesis, arises via the oxidation and dimerisation of 2-aminodiphenylamine with hot nitrobenzene so there is a common intermediate in both syntheses.
- Subjects
NITROBENZENE; ANILINE; PATENTS; X-rays; ISOMERS; DYES &; dyeing
- Publication
Journal of Chemical Research, 2023, Vol 47, Issue 3, p1
- ISSN
1747-5198
- Publication type
Article
- DOI
10.1177/17475198231175602