2-(1,3-Dihydro-3-oxo-2H-indol-2-yliden)-1,2-dihydro-3H-indol-3-on Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Indigo, known chemically as indigotin, is a common blue dye that has been highly valued
throughout history and has played a major role in trade and commerce since ancient times.
The term indigo is often used to describe many blue dyes produced from a number of plants.
For example, woad, a blue dye obtained from the plant Isatis tinctoria, was used throughout
the Mediterannean and Europe and is often identified as indigo. True indigo comes from
the leguminous plant of the genus Indigofera.
The Indigofera genus includes several hundred
species, and indigo has been obtained from a number of these, but the dominant species for
the dye are Indigofera tinctoria grown mainly in India and tropical Asia and Indigofera suff ructiosa
from the tropical Americas. The name indigo comes from the Greek indikon and Latin
indicum meaning “dye from India.” There is evidence that indigo was used several thou sand
years b.c.e. Persian rugs containing indigo color exist from several thousand years b.c.e. Textile
artifacts from Egyptian tombs provide evidence of indigo’s use by royalty from as far back as
2500 b.c.e. The writings of Herodotus from approximately 450 b.c.e. mention indigo’s use in
the Mediterranean area.
Chemische Eigenschaften
dark violet powder
Occurrence
Indigo is a perennial shrub found in several regions of the world.
History
Indigotin. The blue dye of the ancient world was derived from indigo and woad. Which plant is the oldest is a matter of conjecture. That indigo was known at least four thousand years ago is evident from ancient Sanskrit writings. Cloth dyed with indigotin (CI Natural Blue; CI 75780) has been found in Egyptian tombs and in the graves of the Incas in South America. Indigo belongs to the legume family. The two most important species are Indigo tinctoria and I. suffruticosa, found in India and the Americas, respectively. The leaves of the indigo plant do not contain the dye as such, but in the form of its precursor, a glycoside known as indican.
Verwenden
In recent years researchers have used genetic engineering using Escherichia coli to convert tryptophan into indigo. The desire for natural organic products has also revived traditional production methods of indigo on a small scale. Indigo's dominant use is as a textile dye, but indigo-related compounds have limited use as indicators and in food coloring.the Food and Drug Administration's FD&C Blue #2 contains indigotine (also known as indigo carmine), which is a sulfonated sodium salt of indigo.
Definition
indigo: A blue vat dye, C
16H
10N
2O
2.It occurs as the glucoside indican inthe leaves of plants of the genus Indigofera,from which it was formerlyextracted. It is now made synthetically.
Vorbereitung Methode
The first synthesis of indigo is attributed to Adolf von Baeyer (1835–1917), who began hisquest to synthesize indigo in 1865 but was not able to produce indigo until 1878. The syntheticproduction of indigo was first described by Baeyer and Viggo Drewson in 1882; Baeyeralso identified the structure of indigo in 1882.the Baeyer-Drewson synthesis of indigo startedwith 2-nitrobenzaldehyde and acetone proceeding through a series of steps in alkali solution.Baeyer’s work was not commercially viable, and it was not until 1897 that BASF (BadischeAnalin und Soda Fabrik) started to produce indigo commercially using a process developedby Karl von Heumann (1851–1894) that started with naphthalene. The synthetic productionof indigo spelled the end of traditional methods of indigo production. By the second decadeof the 20th century, nearly all indigo was produced synthetically.
Biologische Funktion
Indigo naturalis has a variety of pharmacological activities, such as anti-inflammatory, antioxidant, antibacterial, antiviral, immunomodulatory and so on. It has very good clinical effect on psoriasis, leukemia and ulcerative colitis.
Allgemeine Beschreibung
Dark blue powder with coppery luster. Occurs in isomeric forms (cis and trans). In solid state Indigo is in the trans form.
Air & Water Reaktionen
Insoluble in water.
Health Hazard
ACUTE/CHRONIC HAZARDS: Indigo may cause irritation of the skin and mucous membranes.
Brandgefahr
Flash point data for Indigo are not available but Indigo is probably combustible.
Sicherheitsprofil
Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.
läuterung methode
First reduce indigo in alkaline solution with sodium hydrosulfite, and filter. The filtrate is then oxidised by air, and the resulting precipitate is filtered off, dried at 65-70o, ground to a fine powder, and extracted with CHCl3 in a Soxhlet extractor. Evaporation of the CHCl3 extract gives the purified dye. [Brode et al. J Am Chem Soc 76 1034 1954; spectral characteristics are listed, Beilstein 24 II 233, 24 III/IV 1791.]
2-(1,3-Dihydro-3-oxo-2H-indol-2-yliden)-1,2-dihydro-3H-indol-3-on Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Chloressigsäure
Kaliumhydroxid
Phenyl glycine
Natriumchlorid
Disodium
Natrium
Aluminium, 2-(1,3-Dihydro-3-oxo-5-sulfo-2H-indol-2-yliden)-2,3-dihydro-3-oxo-1H-indol-5-sulfonsure Komplex
Concentrated sulfuric acid
Anilin
Natriumhydroxid
Dinatrium-5,5'-(2-(1,3-dihydro-3-oxo-2H-indazol-2-yliden)-1,2-dihydro-3H-indol-3-on)disulfonat
Indol
Aluminiumsulfat
Aluminiumhydroxid
Natriumcarbonat
Ammoniak, wasserfrei
3H-Indol-3-one, 1,2,4,5,6,7-hexahydro-
2-Phenylimino-3-indolinone
N-(Carboxymethyl)anthranilsure
Downstream Produkte
5,7-Dibrom-2-(5,7-dibrom-1,3-dihydro-3-oxo-2H-indol-2-yliden)-1,2-dihydro-3H-indol-3-on
Indolin-2,3-dion
Aluminium, 2-(1,3-Dihydro-3-oxo-5-sulfo-2H-indol-2-yliden)-2,3-dihydro-3-oxo-1H-indol-5-sulfonsure Komplex
Dinatrium-5,5'-(2-(1,3-dihydro-3-oxo-2H-indazol-2-yliden)-1,2-dihydro-3H-indol-3-on)disulfonat
Indol
Ethanone, 1-(3-hydroxy-1H-indol-2-yl)- (9CI)
C.I.Vat Blue 35
5,7-Dibrom-2-(5,7-dibrom-1,3-dihydro-3-oxo-2H-indol-2-yliden)-1,2-dihydro-3H-indol-3-on
