Uncovering John Holliday’s industrial dye synthesis patented in 1865

M. Plater, W. Harrison
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引用次数: 0

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.
1865年发现约翰·霍利迪的工业染料合成专利
霍利迪1865年的工业染料合成用硝基苯加热盐酸苯胺,并用现代光谱方法对产物进行了表征。以低收率分离得到一种红色染料,并通过x射线单晶结构测定鉴定为9-苯基-3-苯胺-苯那酮-2-苯胺。该结构与93年后的1958年用FeCl3氧化2-氨基二苯胺盐酸盐,然后用苯胺加热两种产物得到的结构相同。用x射线法测定了苯胺转红花氨酸异构体的单晶结构。从Holliday的合成中分离出来的9-苯基-3-苯胺苯酮-2-苯胺是通过2-氨基二苯胺与热硝基苯的氧化和二聚化产生的,因此在两种合成中都有一个共同的中间体。
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来源期刊
Journal of Chemical Research-s
Journal of Chemical Research-s 化学科学, 有机化学, 有机合成
自引率
0.00%
发文量
0
审稿时长
1 months
期刊介绍: The Journal of Chemical Research is a peer reviewed journal that publishes full-length review and research papers in all branches of experimental chemistry. The journal fills a niche by also publishing short papers, a format which favours particular types of work, e.g. the scope of new reagents or methodology, and the elucidation of the structure of novel compounds. Though welcome, short papers should not result in fragmentation of publication, they should describe a completed piece of work. The Journal is not intended as a vehicle for preliminary publications. The work must meet all the normal criteria for acceptance as regards scientific standards. Papers that contain extensive biological results or material relating to other areas of science may be diverted to more appropriate specialist journals. Areas of coverage include: Organic Chemistry; Inorganic Chemistry; Materials Chemistry; Crystallography; Computational Chemistry.
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