82-38-2

Usage

Uses

Used in Textile Industry:
Disperse Red 9 is used as a dyeing agent for polyester, polyamide fiber, acrylic, acetate fiber, and triacetate fiber. It provides good colorfastness properties, including ironing fastness, light fastness, perspiration fastness, and washing fastness, as per the ISO standards.
Used in Leather Industry:
Disperse Red 9 is used as a dyeing agent for sheepskin, providing a vibrant and long-lasting color.
Used in Plastic Industry:
Disperse Red 9 is used for coloring plastics, imparting a bright red hue and enhancing the appearance of plastic products.

Preparation

1-Chloroanthraquinone?or 9,10-Dioxo-9,10-dihydroanthracene-1-sulfonic acid?in pressure and in the presence of antioxidants with Methanamine for processing.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 573, 1955Synthetic Communications, 21, p. 1889, 1991 DOI: 10.1080/00397919108021779

Standard(Vinegar fiber)

Ironing Fastness

Fading

Stain

Purification Methods

Crystallise it to constant melting point from butan-1-ol, then from EtOH. It can be sublimed under vacuum. [Beilstein 7 IV 2574.]

InChI:InChI=1/C15H11NO2/c1-16-12-8-4-7-11-13(12)15(18)10-6-3-2-5-9(10)14(11)17/h2-8,16H,1H3

Upstream product

• 4597-87-9 2-(N-methylamino)pyridine 
• 82-39-3 1-methoxyanthracene-9,10-dione 
• 17613-65-9 1-phenoxy-anthraquinone 
• 82-49-5 1-anthraquinonesulfonic acid 
• 64-17-5 ethanol 
• 82-44-0 1-chloroanthracene-9,10-dione 
• 74-89-5 methylamine 
• 128-93-8 1-bromo-4-(methylamino)-9,10-anthracenedione 
• 82-45-1 1-amino-9,10-anthracenedione 
• 77-78-1 dimethyl sulfate 
• 569-06-2 1-fluoro-9,10-anthraquinone 
• 57-14-7 N,N-Dimethylhydrazine 
• 82-34-8 1-nitroanthraquinone 
• 107-13-1 acrylonitrile 

Downstream Products

• 52868-94-7 N-(9,10-dioxo-9,10-dihydro-[1]anthryl)-N-methyl-benzamide 
• 82-45-1 1-amino-9,10-anthracenedione 
• 138452-38-7 10-Benzyl-10-benzyloxy-4-methylamino-9(10H)-anthracenone 
• 128-93-8 1-bromo-4-(methylamino)-9,10-anthracenedione 
• 6374-84-1 1-methylamino-2-bromoanthraquinone 
• 3179-96-2 1-Methylamino-4-phenylaminoanthraquinone 
• 670259-07-1 1-benzoyl-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione 
• 1220-94-6 1-amino-4-(methylamino)anthraquinone 
• 138452-30-9 2-Methyl-1-phenylnaphth<1,2,3-cd>indol-6(2H)-one 
• 6373-16-6 1-methylamino-4-hydroxyanthraquinone 

Relevant academic research and scientific papers

Ionic liquids as novel and recyclable reaction media for N-alkylation of amino-9,10-anthraquinones by trialkyl phosphites

Ionic liquids such as 1,3-dialkylimidazolium bromides make excellent catalysts and solvents for N-alkylation of amino-9,10-anthraquinones in the presence of trialkyl phosphites. For triethyl phosphite, [bpim][Br] gave better results. The ionic liquids are successfully regenerated and reused.

Perfluoroalkylquinones. Synthesis Using Bis(perfluoroalkanoyl) Peroxides, Absorption Bands, and Solubility

The reactions of 1,4-benzo-, naphtho-, and 9,10-anthraquinones with bis(perfluoroalkanoyl) peroxides gave the corresponding perfluoroalkylated derivatives.Those of 2-methyl- and 2--1,4-naphthoquinones with bis(oxaperfluoroalkanoyl) peroxides afforded the dichloromethyl and trifluoromethyl derivatives, respectively.Absorption bands of the perfluoroalkylated naphtho- and anthraquinone dyes showed a slight hypsochromic shift.The solubilities of the perfluoroalkylated anthraquinone dyes into hexane were much more higher than those of the non-perfluoroalkylated ones.

Method for synthesizing solvent dye intermediate

The invention discloses a method for synthesizing a solvent dye intermediate. The dye intermediate is 1-methylaminoanthraquinone, and the method comprises the following steps: 1-aminoanthraquinone andchloromethane are used as the raw materials, and the target product is obtained by the condensation reaction under the action of a catalyst and an acid binding agent in a polar solvent. The route that 1-methylaminoanthraquinone is synthesized by using 1-aminoanthraquinone and chloromethane as the raw materials does not have nitrosamine formation, the high quality solvent dye intermediate is produced, and the quality of downstream products is improved. Moreover, the method uses ammonium chloride, ammonium acetate or ammonium nitrate as the reaction catalyst, the selectivity of the main productsecondary amine is improved, and the side reaction tertiary amine production is reduced.

Non-reductive conversion of 1-nitro-9,10-anthraquinone to 1-amino-9,10-anthraquinones

Heating 1-nitro-9,10-anthraquinone 2 with ureas 4 in N,N,N',N'-tetramethylurea (TMU) at around 130 °C resulted in the displacement of the nitro group by the amino groups, leading to the corresponding aminoanthraquinones 5 in good yields.

Process for preparing substituted aminoanthraquinones

Substituted aminoanthraquinone compounds, which are used for dye stuffs or intermediate thereof, represented by the formula (II) STR1 wherein R3 represents a C1 -C6 alkyl group which may be substituted, X represents a hydrogen atom, --COR1 or --SO2 R2 wherein R1 and R2 each represents a substituted or unsubstituted C1 -C4 alkyl or C6 -C12 aryl group, and Y and Z represent independently a hydrogen atom, a halogen atom, a nitro group or a C1 -C4 alkyl group, is prepared by allowing anthraquinone compounds represented by the formula STR2 wherein X, Y and Z are as defined above, to react with alkylating agents in organic solvents in the presence of organic quaternary ammonium salts and alkalies.

Facile synthesis of substituted n-monoalkylaromatic amines under PTC conditions

Substituted aromatic amides were alkylated under PTC conditions. Compounds with ortho electron withdrawing substituents furnished exclusively monoalkyl amines. A plausible mechanism has been suggested.

Phase transfer catalysed N-monoalkylation of amino anthraquinones

1-Alkylaminoanthraquinones (2a-f) and 1,4-bisalkylaminoanthraquinones (4a-c) were prepared from aminoanthraquinones (1,3) by alkylation with alkyl sulphate/alkyl halide in presence of powdered sodium hydroxide, potassium carbonate and phase transfer catalyst.

Formation of N-N and N-C Bond-Cleavage Products in Displacements with N,N-Disubstituted Hydrazines on 1-Halo- or 1,4-Dihaloanthracene-9,10-diones

The displacements of 1-halo- and 1,4-dihaloanthracene-9,10-diones by N,N-disubstituted hydrazines have been studied.These reactions proceed via N-N bond cleavages of the hydrazine to yield products with the regiospecific incorporation of an N,N-disubstituted amino group.In addition, pyrazoles which arise from intermediates which undergo N-C bond cleavage are also formed.The ratio of the N-N to N-C cleavage products is dependent on the reaction solvent, temperature, structure of the hydrazine, and the nature of the leaving group being displaced from the anthracene-9,10-dione.For example, treatment of 1a with N,N-dimethylhydrazine in pyridine or dimethyl sulfoxide (DMSO) leads to 3a:2c ratios of 6 and 3, respectively.Compound 1e under comparable reaction conditions gives 3a:2c product ratios of 49 and 4, respectively.The dichloro dione 1c with N,N-dimethylhydrazine in pyridine or DMSO leads predominantly to 3b in 76percent and 72percent yields, respectively, with relatively little pyrazole 2d.The more reactive difluoro dione 1h on reaction with N,N-dimethylhydrazine in pyridine leads to N-N bond-cleavage products 3c (48percent) and 3d (40percent).Treatment of 1e with 1-piperidinamine in pyridine yields 3f.The results will be discussed.

REACTION OF 1-CHLORO- AND 1-NITROANTHRAQUINONES WITH 3-ALKYLAMINO- AND 3-DIALKYLAMINOPROPIONITRILES

The reaction of 1-chloro- and 1-nitroanthraquinones with 3-alkylaminopropionitriles at 130-170 deg C leads to the formation of 1-alkylaminoanthraquinones; the reaction with 3-dialkylaminopropionitriles leads to 1-dialkylaminoanthraquinones, which undergo thermal cleavage under the reaction conditions (isoamyl alcohol, 130 deg C) with the formation of 1-alkylaminoanthraquinone.The nature of the substituted atom affects the reaction rate; the nitro group is substituted 54 times more quickly than the chlorine atom.The initial reaction rates in alcohols are 2-3 orders of magnitude higher than in benzene.

SOME RELATIONSHIPS IN THE SYNTHESIS OF BIARYLS FROM HALOGENOANTHRAQUINONES

The effects of the solvent and the concentration of the reagents on the reaction path and on the results of the synthesis of biaryls from halogenoanthraquinones were investigated for the case of the reaction of 1-chloro-4-benzoylaminoanthraquinone with copper.The use of concentrated reaction mixtures and of donating aprotic dipolar solvents with copper-aryl halide ratios slightly exceeding an equimolar ratio leads to a reduction in the induction period and to an increase in the yield of the biaryls.This explained by interaction between the copmonents of the metal-aryl halide-solvent complex.