4051-63-2

Basic information

• Product Name: Pigment Red 177
• Synonyms: C.I. 65300;4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone;pigment red 177;1,1-Bianthracene-9,9,10,10-tetrone, 4,4-diamino-;ANTHRAQUINONE RED;Pigment red 177 (C.I. 65300);Fast Red A3B;C.I. Pigment Red 177
• CAS NO: 4051-63-2
• Molecular Formula: C₂₈H₁₆N₂O₄
• Molecular Weight: 444.43764
• EINECS: 223-754-4
• Mol File: 4051-63-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 356-358°C
• Boiling Point: 797.2 °C at 760 mmHg
• Flash Point: 435.9 °C
• Appearance: /
• Density: 1.488
• Vapor Pressure: 2.03E-25mmHg at 25°C
• Refractive Index: 1.77
• PKA: -0.63±0.20(Predicted)
• Water Solubility: 25μg/L at 20-23℃
• CAS DataBase Reference: Pigment Red 177(CAS DataBase Reference)
• NIST Chemistry Reference: Pigment Red 177(4051-63-2)
• EPA Substance Registry System: Pigment Red 177(4051-63-2)

Safety Data

• Hazardous Substances Data: 4051-63-2(Hazardous Substances Data)

Usage

Description

Pigment Red 177 is a red powder with a bluish shade, which is reddish compared to A3B. It has a heat resistance of a minimum of 300°C and exhibits good light fastness with a rating of 7-8. The pigment also has a moderate acid and alkali resistance with a rating of 5, and a fastness to bleeding rating of 5. It has an oil absorption rate of 35-40%, a specific surface area of 27 m2/g, and a density of 1.60 g/cm3. The pigment has a maximum water solubility of 1.0% and a maximum residue on an 80 mesh screen of 5.0%. It has a tinging strength of 100-105%.

Uses

Used in Paint Industry:
Pigment Red 177 is used as a colorant for its excellent heat resistance, light fastness, and acid and alkali resistance. Its bluish shade with a reddish tone compared to A3B makes it suitable for creating a wide range of red hues in the paint industry.
Used in Plastics Industry:
The pigment is also used in the plastics industry for coloring various types of plastics. Its good heat resistance and resistance to acids and alkalis make it an ideal choice for use in the production of durable and long-lasting colored plastics.
Used in Printing Industry:
Pigment Red 177 is used as an ink additive for its strong tinging strength and good light fastness. Its bluish shade with a reddish tone compared to A3B allows for the creation of vibrant and long-lasting red colors in the printing industry.
Used in Coatings Industry:
The pigment is also used in the coatings industry for its excellent heat resistance, light fastness, and resistance to acids and alkalis. Its bluish shade with a reddish tone compared to A3B makes it suitable for use in the production of high-quality and durable coatings.
Used in Textile Industry:
Pigment Red 177 is used as a dye for coloring fabrics in the textile industry. Its good heat resistance, light fastness, and resistance to acids and alkalis make it an ideal choice for use in the production of long-lasting and vibrant colored textiles.

TEST ITEMS

SPECIFICATION

HEAT RESISTANCE

300°C min

LIGHT FASTNESS

7-8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

OIL ABSORPTION

35-40%

SPECIFIC SURFACE

27 m 2 /g

DENSITY

1.60 g/cm 3

RESIDUE ON 80 MESH

5.0% max

VOLATITE 105 °C

1.0% max

InChI:InChI=1/C28H16N2O4/c29-19-11-9-13(21-23(19)27(33)17-7-3-1-5-15(17)25(21)31)14-10-12-20(30)24-22(14)26(32)16-6-2-4-8-18(16)28(24)34/h1-12H,29-30H2

Synthetic route

disodium 4,4'-diamino-1,1'-bianthraquinonyl-3,3'-disulfonate (6022-22-6) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With 1-(4-sulfonylbutyl)pyridinium trifluoromethanesulfonate at 110 - 140℃; for 6.25h; Reagent/catalyst; Temperature;	98.22%
With sulfuric acid at 160℃; for 3.5h;

4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonic acid (69166-06-9) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With 1-(n-butyl)-3-methylimidazolium triflate at 140℃; for 11h; Temperature; Ionic liquid;	97.9%
With sodium hydroxide; D-glucose

1-Nitro-4-chloroanthraquinone (6337-82-2) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With copper Reduktion des Produkts;

4,4'-Dibenzoylamino-1,1'-bianthraquinonyl (94117-83-6) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With sulfuric acid at 90 - 100℃; Yield given;

1-benzamido-4-chloroanthraquinone (81-45-8) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / Copper powder / dimethylformamide / 1.5 h / Heating 2: conc.H2SO4 / 90 - 100 °C View Scheme

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous alkaline solution; copper 2: aq. NaOH solution; D-glucose View Scheme

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + benzoyl chloride (98-88-4) → 4,4'-Dibenzoylamino-1,1'-bianthraquinonyl (94117-83-6)

Conditions	Yield
With nitrobenzene at 180℃;

C9H13ClN2O3 + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C37H28N4O7 (847453-73-0)

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 6h; Heating / reflux;

C15H15ClN2O3 (847453-81-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C43H30N4O7

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 12h;
In dimethyl sulfoxide at 120℃; for 12h;

C18H35NO2 (677798-25-3) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C46H49N3O5 (677798-31-1)

Conditions	Yield
Stage #1: C18H35NO2 With thionyl chloride In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone In dimethyl sulfoxide at 80℃; for 6h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C34H14Cl4N8O4 (98809-03-1)

Conditions	Yield
In 1,4-dioxane at 100℃; for 10h;

2-Ethylhexylamine (104-75-6) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C66H86N12O4 (1227678-81-0)

Conditions	Yield
In 1,4-dioxane for 7h; Reflux;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 3-cyclohexylpropionyl chloride (39098-75-4) → C46H44N2O6 (1228443-08-0)

Conditions	Yield
In chlorobenzene for 3h; Reflux;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 4-diphenylsulfonyl chloride (1623-93-4) → C52H32N2O8S2 (1228443-12-6)

Conditions	Yield
In dichlorobenzene, 1,2- at 185℃; for 6h;

cyclopentanepropanoyl chloride (104-97-2) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C44H40N2O6 (1281462-05-2)

Conditions	Yield
In chlorobenzene at 180℃; for 2h;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 2-(benzyloxy)ethyl chloroformate (56456-19-0) → C48H36N2O10 (1228443-13-7)

Conditions	Yield
In dichlorobenzene, 1,2- at 185℃; for 10h;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + chloroacetyl chloride (79-04-9) → C32H18Cl2N2O6 (1228443-10-4)

Conditions	Yield
In chlorobenzene at 100℃; for 4h;

3-cyclohexanecarbonyl chloride (462661-49-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C42H36N2O6 (1228443-09-1)

Conditions	Yield
In dichlorobenzene, 1,2- at 180℃; for 1h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → C70H90N16O4

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone With N,N-dimethyl acetamide at 100 - 110℃; for 5h; Stage #2: N-(3-aminopropyl)cyclohexylamine at 130 - 140℃; for 3h;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 4-hydroxy-3,5-di-tert-butylphenylpropionic acid (20170-32-5) → C62H64N2O8

Conditions	Yield
Stage #1: 4-hydroxy-3,5-di-tert-butylphenylpropionic acid With thionyl chloride In N,N-dimethyl acetamide at 40 - 50℃; for 0.5h; Stage #2: 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone In N,N-dimethyl acetamide at 120 - 130℃; for 3h;

Upstream product

• 6022-22-6 disodium 4,4'-diamino-1,1'-bianthraquinonyl-3,3'-disulfonate 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 81-45-8 1-benzamido-4-chloroanthraquinone 
• 69166-06-9 4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonic acid 
• 94117-83-6 4,4'-Dibenzoylamino-1,1'-bianthraquinonyl 
• 6337-82-2 1-Nitro-4-chloroanthraquinone 

Downstream Products

• 1228443-09-1 C₄₂H₃₆N₂O₆ 
• 1228443-13-7 C₄₈H₃₆N₂O₁₀ 
• 1228443-12-6 C₅₂H₃₂N₂O₈S₂ 
• 1228443-08-0 C₄₆H₄₄N₂O₆ 
• 94117-83-6 4,4'-Dibenzoylamino-1,1'-bianthraquinonyl 

Relevant articles and documents

Method for efficiently preparing 4,4-diamino-1,1-dianthraquinone by using Bronsted acid functionalized ionic liquid

The invention discloses a method for efficiently preparing 4,4-diamino-1,1-dianthraquinone by using Bronsted acid functionalized ionic liquid. The method comprises the steps: weighing the Bronsted acid functionalized ionic liquid, adding the weighed Bronsted acid functionalized ionic liquid into a reaction vessel, and heating the temperature of the Bronsted acid functionalized ionic liquid to a certain temperature; slowly adding sodium 4,4-diamino-1,1-dianthraquinone-3,3-disulfonate, carrying out a heated reaction for certain time with stirring, and cooling the temperature of a reacted substance to a certain temperature after the reaction ends up; dropwise adding a certain amount of organic solvent, carrying out uniform stirring, then, carrying out suction filtration, and washing the reacted substance with the solvent until the reacted substance is colorless; and subjecting a filter cake to vacuum drying, thereby obtaining the 4,4-diamino-1,1-dianthraquinone. According to the method, concentrated sulfuric acid is replaced with the Bronsted acid functionalized ionic liquid which serves as a reaction medium for producing the 4,4-diamino-1,1-dianthraquinone, no waste acid is discharged, the yield of the 4,4-diamino-1,1-dianthraquinone reaches up to 98% or more, and thus, the method is in line with general orientation of environment-friendly and cyclic development and has a broad application prospect.

Ionic liquid in the preparation of pigment red 177 method

The invention belongs to a method for preparing pigment red 177 in an ionic liquid. The method comprises the steps: mixing 4, 4'-diamino-1, 1'-dianthraquinone-3, 3'-disulfonic acid (DAS) in the ionic liquid, heating at high temperature, and carrying out desulfonation reaction; and after the reaction is ended, adding a methyl alcohol solvent into the reaction mixture to separate out the pigment red 177, filtering and drying to obtain the pigment red 177. The problem that a great deal of waste acid is discharged in the existing preparation technology of the pigment red 177 is solved; the process for preparing the pigment red 177 through carrying out desulfonation reaction on the DAS in about 70-80% of slfuric acid medium is not needed, no waste dilute sulphuric acid is discharged, and the yield of the pigment red 177 is over 95%. According to the invention, the pigment red 177 is prepared by using a technology for carrying out desulfonation reaction in the ionic liquid, so that the process is simple, the discharged waste acid is greatly reduced, and the yield is relatively high.

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.