Uncovering John Holliday’s industrial dye synthesis patented in 1865

Michael John Plater; William TA Harrison

doi:10.1177/17475198231175602

Uncovering John Holliday’s industrial dye synthesis patented in 1865

Michael John Plater^* (Corresponding Author), William TA Harrison

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Journal	Journal of Chemical Research
Volume	47
Issue number	3
Early online date	29 May 2023
DOIs	https://doi.org/10.1177/17475198231175602
Publication status	Published - 2023

Bibliographical note

Open Access via the Sage Agreement
The authors thank the UK Engineering and Physical Sciences Research Council (EPSRC) National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-ray data collections. Data sets were obtained free of charge from the National Crystallography Centre, Southampton University.

Keywords

2-aminodiphenylamine,
aniline
anilinoaposafranine
FeCl3
nitrobenzene
p-benzoquinone

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Cite this

@article{0950b1b8ee5147a98d6a3b9988485fde,

title = "Uncovering John Holliday{\textquoteright}s industrial dye synthesis patented in 1865",

abstract = "Holliday{\textquoteright}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{\textquoteright}s synthesis, arises via the oxidation and dimerisation of 2-aminodiphenylamine with hot nitrobenzene so there is a common intermediate in both syntheses.",

keywords = "2-aminodiphenylamine,, aniline, anilinoaposafranine, FeCl3, nitrobenzene, p-benzoquinone",

author = "Plater, {Michael John} and Harrison, {William TA}",

note = "Open Access via the Sage Agreement The authors thank the UK Engineering and Physical Sciences Research Council (EPSRC) National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-ray data collections. Data sets were obtained free of charge from the National Crystallography Centre, Southampton University.",

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journal = "Journal of Chemical Research",

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AU - Plater, Michael John

AU - Harrison, William TA

N1 - Open Access via the Sage Agreement The authors thank the UK Engineering and Physical Sciences Research Council (EPSRC) National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-ray data collections. Data sets were obtained free of charge from the National Crystallography Centre, Southampton University.

PY - 2023

Y1 - 2023

N2 - 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.

AB - 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.

KW - 2-aminodiphenylamine,

KW - aniline

KW - anilinoaposafranine

KW - FeCl3

KW - nitrobenzene

KW - p-benzoquinone

U2 - 10.1177/17475198231175602

DO - 10.1177/17475198231175602

M3 - Article

SN - 1747-5198

VL - 47

JO - Journal of Chemical Research

JF - Journal of Chemical Research

IS - 3

ER -

Uncovering John Holliday’s industrial dye synthesis patented in 1865

Abstract

Bibliographical note

Keywords

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