INDULINES

This article appears in Volume V14, Page 507 of the Encyclopedia Britannica.

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INDULINES , a

series

SERIES (a Latin word from serere, to join)

of dyestuffs of blue, bluish-red or black shades, formed by the interaction of para-amino azo compounds with

primary

PRIMARY

monamines in the presence of a small quantity of a

mineral

MINERAL

acid. They were first discovered in 1863 (

English

ENGLISH

patent 3307) by J. Dale and H.

Caro

CARO, ANNIBALE (1507-1566)
CARO, ELME
MARIE
- MARIE
(1826-1887)

, and since then have been examined by many chemists (see O. N. Witt, Ber., 1884, 17, p. 74; O. Fischer and E. Hepp, Ann., 1890, 256, pp. 233 et seq.; F. Kehrmann, Bet., 1891, 24, pp. 584, 2167 et seq.). They are derivatives of the eurhodines (aminophenazines, aminonaphthophenazines), and by means of their diazo derivatives can be de-amidated, yielding in this way azonium salts; consequently they may be considered as amidated azonium salts. The first reaction giving a clue to their constitution was the

isolation

ISOLATION

of the intermediate azophenin by O. Witt (Jour. Chem. Soc., 1883, 43, p. 115), which was proved by Fischer and Hepp to be dianilidoquinone dianil, a similar intermediate compound being found shortly afterwards in the naphthalene

series

SERIES (a Latin word from serere, to join)

. Azophenin, Ca,H24N4, is prepared by warming quinone dianil with aniline; by melting together quinone, aniline and aniline hydrochloride; or by the action of aniline on para-nitrosophenol or para-nitrosodiphenylamine. The indulines are prepared as mentioned above from aminoazo compounds:
NH2C6H4N2Celia-I-C6I-ISNH,-> HN : C6H3 C6H4,
(aposafranine)
or by condensing oxy- and amido-

quinones

QUINONES

with phenylated ortho-diamines (F. Kehrmann, Ber., 1895, 28, p. 1714):
H0>C6H2H+C6H,NH>C6H4=
2H2O--HO>C6H2C6H5

C6H5

The indulines may be subdivided into the following groups:(I) benzindulines, derivatives of phenazine; (2) isorosindulines; and (3) rosindulines, both derived from naphthophenazine; and (4) naphthindulines, derived from naphthazine.
T
NH:C6H3 CH4 NH: CH3CioH6
I. Benzindulines. II. Isorosindulines.
NH: CioH5CH4 NH: CioH5 CioHa
The rosindulines and naphthindulines have a strongly basic

character

CHARACTER (Gr. xapareri7p, from xap&crew, to scratch)

, and their salts possess a marked red colour and fluorescence. Benzinduline (aposafranine), C16H13N3, is a strong base, but cannot be diazotized, unless it be dissolved in concentrated

mineral

MINERAL

acids. When warmed with aniline it yields anilido-aposafranine, which may also be obtained by the direct oxidation of ortho-aminodiphenylamine. Isorosinduline is obtained from quinone dichlorimide and phenyl-13-naphthylamine; rosinduline from benzeneazo-a-naphthylamine and aniline and naphthinduline from benzeneazo-a-naphthylamine and naphthylamine.

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