128-70-1

Basic information

• Product Name: Vat Orange 9
• Synonyms: pyranthrenedione;Pyranthron;Pyranthrone;Romantrene Golden Orange FG;Sandothrene Golden Orange NG;Solanthrene Orange F-J;Solanthrene Orange J;Tinon Golden Orange G
• CAS NO: 128-70-1
• Molecular Formula: C₃₀H₁₄O₂
• Molecular Weight: 406.43
• EINECS: 204-906-9
• Product Categories: Organics
• Mol File: 128-70-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 703.7 °C at 760 mmHg
• Flash Point: 250 °C
• Appearance: /
• Density: 1.489
• Vapor Pressure: 1.2E-19mmHg at 25°C
• Refractive Index: 1.909
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Vat Orange 9(CAS DataBase Reference)
• NIST Chemistry Reference: Vat Orange 9(128-70-1)
• EPA Substance Registry System: Vat Orange 9(128-70-1)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 128-70-1(Hazardous Substances Data)

Usage

Description

Vat Orange 9 is a yellow-orange powder that is soluble in 1,2,3,4-Tetrahydronaphthalene and Xylene, and slightly soluble in alcohol. It exhibits different color properties under various conditions, such as turning yellow-brown in strong sulfuric acid, blue-ray red body hidden color in alkaline reduction, and orange color body hidden in acid reduction.

Uses

Used in Textile Industry:
Vat Orange 9 is used as a light brittle dye for cotton fiber, providing accelerated coloration in sunlight. It is not typically used for monochromatic dyeing of cotton cloth due to its light brittle nature, and consumption should be controlled. However, it can be used for spelling color, direct printing, and discharge. It is also suitable for dyeing viscose and silk.
Used in Dyeing Polyester/Cotton Blended Fabric:
Vat Orange 9 is used for dyeing polyester/cotton blended fabric, where it exhibits serious dyeing properties.
Standard:
The standard for Vat Orange 9 includes various fastness and bleaching properties, such as:
Ironing Fastness: ISO 4, AATCC 4
Chlorine bleach: ISO 5, AATCC 5
Light Fastness: ISO 5-6, AATCC 5-6
Mercerized: Not specified
Oxygen bleach: ISO 4-5, AATCC 4-5
Soaping: ISO 4-5, AATCC 4-5
Fading: Not specified
Stain: Not specified
These properties indicate the performance and durability of Vat Orange 9 in various conditions, making it suitable for specific applications in the textile industry.

Preparation

8,16-Pyranthrenedione called. (a) 1-(2-Methyl-9,10-dioxoanthracene-1-yl)-2-methylanthracene-9,10-dione in 350 ~ 380 ℃ heat alone, or in low temperature with dehydrant processing, take off 2 Moore water; (b) 1-(2-Methyl-9,10-dioxoanthracene-1-yl)-2-methylanthracene-9,10-dione?aqueous cream content (with or without ammonia or salt all but), in 230 ~ 250 ℃ and under pressure heating 10 to 12 hours; (C) 1-(2-Methyl-9,10-dioxoanthracene-1-yl)-2-methylanthracene-9,10-dione?and Etanol/Potassium hydroxide heating 10 to 12 hours; (d) 1,6-Dibenzoylpyrene?with Aluminium chloride and Sodium chloride melting, and access to oxygen.

Standard

Ironing Fastness

Fading

Stain

ISO

4

AATCC

4

InChI:InChI=1/C30H14O2/c31-29-19-7-3-1-5-17(19)23-13-15-9-12-22-28-24(18-6-2-4-8-20(18)30(22)32)14-16-10-11-21(29)27(23)25(16)26(15)28/h1-14H

Upstream product

• 54811-16-4 1,6-dibenzoylpyrene 
• 81-26-5 2,2'-dimethyl-1,1'-bianthraquinone 
• 873987-92-9 9,10,9',10'-tetraoxo-9,10,9',10'-tetrahydro-[1,1']bianthryl-2,2'-dicarbaldehyde 
• 129-00-0 pyrene 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 55009-76-2 1,8-dibenzoylpyrene 
• 7376-03-6 phenylpyren-1-yl-methanone 
• 7446-70-0 aluminium trichloride 
• 34119-00-1 1-naphthyl(pyren-1-yl)methanone 
• 7664-93-9 sulfuric acid 
• 590-67-0 1-Methylcyclohexanol 

Downstream Products

• 191-13-9 pyranthrene 
• 19339-23-2 Leucopyranthron-dibenzoat 

Relevant articles and documents

In quest of reversibility of Friedel-Crafts acyl rearrangements in the pyrene series

Friedel-Crafts acyl rearrangements in PPA of diacetylpyrenes (80–120 °C), dibenzoylpyrenes (80–200 °C), and bis(4-flurobenzoyl)pyrenes (80–120 °C) and Scholl reactions in AlCl3/NaCl of dibenzoylpyrenes (140–200 °C) have been studied. The substrates were 1-AcPY, 2-AcPY, 1,3-Ac2PY, 1,6-Ac2PY, 1,8-Ac2PY, 2,7-Ac2PY, 1-BzPY, 1,6-Bz2PY, 1,8-Bz2PY, 1-4FBzPY, 1,6-4FBz2PY, 1,8-4FBz2PY. The mixtures of pyrene, 1-AcPY, 2-AcPY, 1,3-Ac2PY, 1,6-Ac2PY, 1,8-Ac2PY, and 2,7-Ac2PY were separated by HPLC. The following reversible intermolecular isomerizations were established: 1,6-Ac2PY ? 1,8-Ac2PY, 1,6-Bz2PY ? 1,8-Bz2PY, and 1,6-4'FBz2PY ? 1,8-4'FBz2PY, albeit not in high yields. The results substantiate Gore’s 1955 proposition that “The Friedel–Crafts acylation reaction of reactive aromatic hydrocarbons is a reversible process.” The isomerizations reported here differ from the few previously reported completely reversible intramolecular Friedel-Crafts acyl rearrangements. At ≥ 140 °C, in PPA and in AlCl3/NaCl, 1,6-Bz2PY and 1,8-Bz2PY underwent a highly regioselective double Scholl reaction to give pyranthrone (3) and deacylations to 1-BzPy (and pyrene), followed by mono-Scholl reactions to give 8H-dibenzo[def,qr]chrysen-8-one (1), and 11H-indeno[2,1-a]pyren-11-one (2). The formation of 3 and not the expected tribenzo[a,ghi,o]perylene-7,16-dione (4) from 1,8-Bz2PY indicates that 1,8-Bz2PY has first undergone isomerization to 1,6-Bz2PY. The present study confirms the linkage between Friedel-Crafts acyl rearrangements and the Scholl reaction.

Process for the production of pyranthrones or flavanthrones

A process for the production of pyranthrones or flavanthrones which comprises reacting substituted or unsubstituted 2,2'-dialkyl-1,1'-dianthraquinonyls or 2,2'-diacylamino-1,1'-dianthraquinonyls respectively in a two-phase system of aqueous organic solvents using quaternary ammonium or phosphonium compounds as catalysts.