82-18-8

Basic information

• Product Name: 1,5-DIBENZAMIDOANTHRAQUINONE
• Synonyms: n,n’-(9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis-benzamid;N,N’-(9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis-Benzamide;1,5-DIBENZAMIDOANTHRAQUINONE;N,N'-(9,10-dihydro-9,10-dioxoanthracene-1,5-diyl)bisbenzamide;N,N'-1,5-anthraquinonylenebisbenzamide;N,N′-(9,10-Dihydro-9,10-dioxoanthracen-1,5-diyl)bisbenzamid;Vat yellow 3 (C.I. 61725);1,5-Bis(benzoylamino)-9,10-anthraquinone
• CAS NO: 82-18-8
• Molecular Formula: C₂₈H₁₈N₂O₄
• Molecular Weight: 446.45
• EINECS: 201-401-5
• Mol File: 82-18-8.mol

Chemical Properties

• Melting Point: 390 °C
• Boiling Point: 556.3 °C at 760 mmHg
• Flash Point: 159.5 °C
• Appearance: /
• Density: 1.409 g/cm³
• PKA: 12.04±0.20(Predicted)
• CAS DataBase Reference: 1,5-DIBENZAMIDOANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIBENZAMIDOANTHRAQUINONE(82-18-8)
• EPA Substance Registry System: 1,5-DIBENZAMIDOANTHRAQUINONE(82-18-8)

Safety Data

• Hazardous Substances Data: 82-18-8(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
1,5-Dibenzamidoanthraquinone is used as a dye for cotton fabric dyeing due to its color-changing properties and solubility in certain solvents.
The dye exhibits the following standard properties:
Ironing Fastness: ISO 5, AATCC 5
Chlorine bleach: ISO 5, AATCC 5
Light Fastness: ISO 6, AATCC 5
Mercerized: N/A
Oxygen bleach: ISO 4-5, AATCC 4
Soaping: ISO 5, AATCC 4
Fading: N/A
Stain: N/A

Preparation

1,5-Diaminoanthraquinone and Benzoyl chloride (2 Moore) condensation.

Standard

Ironing Fastness

Fading

Stain

ISO

5

AATCC

5

Synthetic route

1,5-diaminoanthraquinone (129-44-2) + benzamide (55-21-0) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
With hydrogenchloride; nitrobenzene

benzamide (55-21-0) + 1,5-Dichloroanthraquinone (82-46-2) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
With potassium carbonate; 1,2-dichloro-benzene; copper(I) bromide

1,5-diaminoanthraquinone (129-44-2) + benzoyl chloride (98-88-4) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
With 2,3-Dimethylaniline
With 1,2-dichloro-benzene at 140℃;
With nitrobenzene at 140℃;

1,5-diaminoanthraquinone (129-44-2) + benzoic acid anhydride (93-97-0) → 1,5-dibenzoylaminoanthraquinone (82-18-8) + 1-amino-5-benzamidoanthraquinone (117-06-6)

Conditions	Yield
With nitrobenzene at 175℃;

1.5-dinitroanthraquinone (82-35-9) → 1,5-dibenzoylaminoanthraquinone (82-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium sulfide 2: dimethylaniline View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4-hydroxy-anthraquinone (6370-96-3)

Conditions	Yield
With manganese(IV) oxide; sulfuric acid
With sulfuric acid

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4,8-dichloro-anthraquinone (115605-23-7)

Conditions	Yield
With chlorine

sulfuric acid (7664-93-9) + 1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4-hydroxy-anthraquinone (6370-96-3)

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-diamino-4,8-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone (119393-92-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorine 3: H2SO4 View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) → 1,5-bis-benzoylamino-4,8-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone (119504-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) → 6,12-dichloro-2,8-diphenyl-anthra[1,9-de;5,10-d'e']bis[1,3]oxazine (121474-48-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine 2: H2SO4 View Scheme

1,5-dibenzoylaminoanthraquinone (82-18-8) + benzoyl chloride (98-88-4) → 1-Chloro-5-benzoylaminoanthraquinone (117-05-5)

Conditions	Yield
In nitrobenzene

Upstream product

• 129-44-2 1,5-diaminoanthraquinone 
• 55-21-0 benzamide 
• 82-46-2 1,5-Dichloroanthraquinone 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 82-35-9 1.5-dinitroanthraquinone 

Downstream Products

• 6370-96-3 1,5-bis-benzoylamino-4-hydroxy-anthraquinone 
• 115605-23-7 1,5-bis-benzoylamino-4,8-dichloro-anthraquinone 
• 119504-37-9 1,5-bis-benzoylamino-4,8-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone 
• 121474-48-4 6,12-dichloro-2,8-diphenyl-anthra[1,9-de;5,10-d'e']bis[1,3]oxazine 
• 117-05-5 1-Chloro-5-benzoylaminoanthraquinone 

Relevant articles and documents

Process for the preparation of 1-acylamino-5(8)-chloroanthraquinones

The invention relates to a novel process for the preparation of 1-acylamino-5(8)-chloroanthraquinones, which are starting materials for the preparation of vat dyes. It is characterized in that 1,5(8)-dichloroanthraquinones is reacted with ammonia at temperatures of 190° to 240° C., the amino groups in the reaction mixture are completely acylated and the more sparingly soluble diacylaminoanthraquinone is separated off from the more readily soluble monoacylaminochloroanthraquinone. The new process yields reaction products which are purer and cheaper than those which are obtained by conventional methods. Moreover there are smaller waste water problems.