81-77-6

Basic information

• Product Name: Vat Blue 4
• Synonyms: 14,18-anthrazinetetrone,6,15-dihydro-9;6,15-dihydroanthrazine-5,9,14,18-tetrone;anthraquinonedeepblue;aticvatbluexrn;benzadonebluers;bleusolanthrene;blueanthraquinonepigment;blueo
• CAS NO: 81-77-6
• Molecular Formula: C₂₈H₁₄N₂O₄
• Molecular Weight: 442.42
• EINECS: 201-375-5
• Mol File: 81-77-6.mol

Chemical Properties

• Melting Point: 470-500°C
• Boiling Point: 553.06°C (rough estimate)
• Flash Point: 253.9 °C
• Appearance: blue needles with a metallic lustre
• Density: 1.3228 (rough estimate)
• Vapor Pressure: 8.92E-22mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.40±0.20(Predicted)
• Water Solubility: <0.1 g/100 mL at 21℃
• Stability: Incompatible with strong oxidizing agents.
• Merck: 14,4934
• CAS DataBase Reference: Vat Blue 4(CAS DataBase Reference)
• NIST Chemistry Reference: Vat Blue 4(81-77-6)
• EPA Substance Registry System: Vat Blue 4(81-77-6)

Safety Data

• Statements: 20/21/22
• Safety Statements: 22-36/37/39
• RTECS: CB8761100
• Hazardous Substances Data: 81-77-6(Hazardous Substances Data)

Usage

Chemical Properties

blue needles with a metallic lustre

Uses

Different sources of media describe the Uses of 81-77-6 differently. You can refer to the following data:
1. Mainly to dye cotton.
2. Indanthrone (Pigment Blue 60) functions as a blue pigment or as a dye.
3. Dinaphtho[2,3-a:2'',3''-h]phenazine-5,9,14,18(6H,15H)-tetraone is a pigment; used in preparation of Polyethylene composite material for outdoor building materials.

Preparation

(a) in potassium nitrate, LvSuanJia, glucose or organic acid salt (such as formic acid potassium or acetic acid potassium or the mixture of both) under the existence of, with potassium hydroxide treatment 2-Aminoanthracene-9,10-dione;

Definition

A blue vat dye or pigment. The molecule consists of two anthraquinone nuclei linked through two –NH groups.

Reactions

As a pigment, indanthrone is a particulate, insoluble solid dispersed directly into a vehicle, whereas as a dye it is reduced to a base-soluble hydroquinone derivative and then reoxidized onto a solid substrate.

General Description

Blue needles with a metallic luster or fine fluffy deep blue powder.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data for Vat Blue 4 are not available. Vat Blue 4 is probably combustible.

Flammability and Explosibility

Notclassified

Properties and Applications

red light blue. Slightly soluble in chloroform (heat), o-chlorophenol,Quinoline, insoluble in acetic acid, acetone, ethanol, pyridine, toluene, xylene. The strong sulfuric acid for brown, after diluted blue precipitation; In alkaline insurance powder solution for blue, acidic solutions for the red light in blue. And C.I. Vat ?Blue 4, C.I. Pigment Blue 60 the same chemical structure.

Purification Methods

Crystallise indanthrene repeatedly from 1,2,4-trichlorobenzene to give a blue powder. It is soluble in alkali and conc H2SO4. [Weinstein & Merritt J Am Chem Soc 81 3759 1959, Beilstein 24 II 317, 24 III/IV 2193.]

InChI:InChI=1/C28H14N2O4/c31-25-13-5-1-3-7-15(13)27(33)21-17(25)9-11-19-23(21)29-20-12-10-18-22(24(20)30-19)28(34)16-8-4-2-6-14(16)26(18)32/h1-12,29-30H

Upstream product

• 91-20-3 naphthalene 
• 82-27-9 2-amino-1-chloroanthraquinone 
• 86-57-7 1-Nitronaphthalene 
• 60245-50-3 1'-amino-1,2'-imino-di-anthraquinone 
• 3300-23-0 1-amino-2-bromoanthraquinone 
• 6374-73-8 2-amino-1-mercaptoanthraquinone 
• 861520-91-4 N,N'-bis-(9,10-dioxo-9,10-dihydro-[1]anthryl)-urea 
• 6370-80-5 N,N'-bis-(9,10-dioxo-9,10-dihydro-[2]anthryl)-urea 
• 5702-54-5 dinaphtho[2,3-a;2',3'-h]phenazine-5,9,14,18-tetraone 
• 100-63-0 phenylhydrazine 
• 82-45-1 1-amino-9,10-anthracenedione 
• 127-09-3 sodium acetate 
• 98-95-3 nitrobenzene 
• 117-79-3 2-aminoanthraquinone 

Downstream Products

• 120-12-7 anthracene 
• 222-64-0 dinaphtho[2,3-a;2',3'-h]phenazine 
• 6259-70-7 naphtho[2,3-f]quinoxaline-2,3,7,12(1H,4H)-tetraone 
• 5702-54-5 dinaphtho[2,3-a;2',3'-h]phenazine-5,9,14,18-tetraone 
• 3635-29-8 9,14-dihydroxy-6,15-dihydro-dinaphtho[2,3-a;2',3'-h]phenazine-5,18-dione; disodium-salt 
• 130-20-1 7,16-dichloro-6,15-dihydroanthrazine-5,9,14,18-tetrone 
• 78679-96-6 N,N'-diphenylindanthrene 

Relevant articles and documents

Indanthrone dye revisited after sixty years

Indanthrone, an old, insoluble dye can be converted into a solution processable, self-assembling and electroluminescent organic semiconductor, namely tetraoctyloxydinaptho[2,3-a:2′,3′-h]phenazine (P-C8), in a simple one-pot process consisting of the reduction of the carbonyl group by sodium dithionite followed by the substitution with solubility inducing groups under phase transfer catalysis conditions.

Improvement method for preparing C.I.vat blue 4

The invention relates to a method for preparing C.I.vat blue 4.The method comprises the steps of preparing 6,15-dihydro-5,9,14,18-anthrazinetetrone and dying 6,15-dihydro-5,9,14,18-anthrazinetetrone.The method is characterized in that according to the main steps of the step 1, on the condition of existence of a mixture of inorganic base and organic base and inert gas, 2-amino anthraquinone or 1-amino anthraquinone react in non-proton polarity organic solvent at the temperature of 140-180 DEG C so that a target object can be obtained, and the target object does not need to be reduced or refined with sodium dithionite and is directly used in the step 2.The yield of the 6,15-dihydro-5,9,14,18-anthrazinetetrone is increased, the steps of preparing the C.I.vat blue 4 are more concise, and the method for preparing the C.I.vat blue 4 has higher commercial value.

Preparation of dianthraquinone-N,N'-dihydroazine and its chlorination products

A process for preparing dianthraquinone-N,N'-dihydroazine (I) STR1 and its chlorination products (Ia) STR2 where n is 1 or 2, by condensation of 1-aminoanthraquinone (II) in the presence of an alkaline condensing aid, an oxidizing agent and a cyclic urea derivative at from 80° to 150° C. and subsequent purification and/or chlorination comprises using N,N'-dimethylpropyleneurea as the urea derivative.

ECOLOGICAL ASPECTS OF INDANTHRONE PRODUCTION.

The authors describe certain procedures for diminishing the harmful effects of indanthrone (I) production on the environment. The purpose of this work was to develop an ecologically acceptable technology for production of Vat Blue 0, with shortening and intensification of stages of low efficiency. It was found that the determining factor in production of Vat Blue 0 is the ratio of the solvent to potassium hydroxide. Melt mobility is ensured by the KOH:H//2O ratio (KOH of 88 mass % concentration is in the liquid phase even at 100 degree ). The highest indanthrone yield is attained at 1:0. 17 ratio of KOH to triethylene glycol (TEG). At 1:1 component ratio indanthrone is not formed, while at 1:05 ratio the yield is not high.