128-70-1

Usage

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Method for synthesizing Vat Golden Orange G original dye

The invention discloses a method for synthesizing a Vat Golden Grange G original dye, which includes the specific steps of: (1) a bromination reaction: taking 2-methyl anthraquinone as a raw material, taking an aprotic solvent as a medium, and reacting with a liquid bromine in a weak base environment to generate 1-bromo-2-methyl anthraquinone; (2) a coupling reaction: taking the 1-bromo-2-methyl anthraquinone as the raw material, adding a catalyst, taking the aprotic solvent as the medium, and producing biquinone C through the coupling reaction; and (C) a closed loop oxidation reaction: taking the biquinone C as the raw material, performing the closed loop reaction in a stable solvent formed by a strong base and an alcoholic solvent, and obtaining the Vat Golden Grange G original dye through an air oxidation reaction. In this technology route, by-products are few, the environmental pollution is little, the reaction yield is higher, the reaction time is shorter, and the industrial production is more convenient.

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.