Vat Blue 4

Iupac Name：2,17-diazaheptacyclo[16.12.0.03,16.04,13.06,11.019,28.021,26]triaconta-1(18),3(16),4(13),6,8,10,14,19(28),21,23,25,29-dodecaene-5,12,20,27-tetrone

CAS No.: 81-77-6

Molecular Weight：442.42176

Modify Date.: 2022-11-29 04:49

Introduction: Blue needles with a metallic luster or fine fluffy deep blue powder. View more+

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1. Names and Identifiers

1.1 Name: Vat Blue 4
1.2 Synonyms: 14,18-anthrazinetetrone,6,15-dihydro-9 6,15-Dihydro-5,9,14,18-anthrazinetetrone, Pigment Blue 60 6,15-dihydroanthrazine-5,9,14,18-tetrone anthraquinone blue anthraquinonedeepblue aticvatbluexrn benzadonebluers bleusolanthrene Blue 60 blueanthraquinonepigment blueo c.i.1106 e130 EINECS 201-375-5 foodblue4 indanthrene indanthrone l-blau1 Pigment Blue 60 ponsolrp vat vatblueo vatblueod

1.3 CAS No.: 81-77-6

1.4 CID: 6690

1.5 EINECS(EC#): 201-375-5

1.6 Molecular Formula: C28H14N2O4 (isomer)

1.7 Inchi: InChI=1S/C28H14N2O4/c31-25-13-5-1-3-7-15(13)27(33)21-17(25)9-11-19-23(21)29-20-12-10-18-22(24(20)30-19)28(34)16-8-4-2-6-14(16)26(18)32/h1-12,29-30H

1.8 InChkey: UHOKSCJSTAHBSO-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C4=C(C=C3)NC5=C(N4)C=CC6=C5C(=O)C7=CC=CC=C7C6=O

1.10 Isomers Smiles: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C4=C(C=C3)NC5=C(N4)C=CC6=C5C(=O)C7=CC=CC=C7C6=O

2. Properties

2.1 Density: 1.487

2.1 Melting point: 470-500℃

2.1 Boiling point: 740.2 oC at 760 mmHg

2.1 Refractive index: 1.746

2.1 Flash Point: 253.9 oC

2.1 Precise Quality: 442.09500

2.1 PSA: 99.86000

2.1 logP: 4.14060

2.1 Solubility: <0.1 g/100 mL at 21 ºC

2.2 Appearance: Vat blue 4 appears as blue needles with a metallic luster or fine fluffy deep blue powder. (NTP, 1992)

2.3 Chemical Properties: blue needles with a metallic lustre

2.4 Color/Form: BLUE POWDER|BLUE NEEDLES

2.5 pKa: -1.40±0.20(Predicted)

2.6 Water Solubility: H2O: <0.1 g/100 mL at 21 oC;SOL IN ANILINE (GREEN-BLUE)

2.7 Spectral Properties: MAX ABSORPTION (ON CELLOPHANE FILM): 278 NM
MAX ABSORPTION (ALCOHOL): 216 NM (LOG E= 4.98), 255 NM (LOG E= 4.92), 292.5 NM (LOG E= 5.17), 371 NM (LOG E= 4.21)
UV: 3-1017 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)

2.8 Stability: Incompatible with strong oxidizing agents.

2.9 StorageTemp: Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.

3. Use and Manufacturing

3.1 General Description: Blue needles with a metallic luster or fine fluffy deep blue powder.

3.2 Methods of Manufacturing: Method 1: Melting method.?Using 2-aminoanthraquinone as raw material, after melting with warm alkali and alkali, the product is refined with insurance powder solution.?Or using 2-aminoanthraquinone as the raw material, dimethyl sulfoxide as the solvent, and performing alkaline fusion reaction with potassium hydroxide, and then refining the insurance powder solution to obtain the product.?.?Add 595 kg of anhydrous mixed alkali (68% of potassium hydroxide) to the condensation pot. After heating and melting, add 131 kg of sodium acetate (98%) and 1.5 kg of oleic acid (industrial product).?Close the condensation pot and heat to 185-190°C. At the same time, drive the air with nitrogen to keep the reaction liquid under the protection of nitrogen. Add 263kg of 2-aminoanthraquinone within 30min, control the temperature not to exceed 215°C, add heat for 1h, then add 25kg sodium nitrite (98%), the control temperature should not exceed 230℃, and it should be added within 2 hours.?Continue stirring for 20 min to complete the alkali melting reaction.?Put 5000L of water in the refining pot, drive the air with nitrogen, put in the alkali molten material, and stir for 2h; cool down to about 51℃, add 110kg of safety powder, and stir slowly. When the temperature is lowered to 45℃, crystals will precipitate.?Filter, the filter cake is washed with an aqueous solution of safety powder (the washing water is made up of 20L liquid alkali, 20kg insurance powder, and 5000L water), and then washed with warm water at 45°C until the filtrate is bluish, and dried to obtain a dye leuco wet material .?Add the dye leuco body wet material to the beating machine, beat with appropriate amount of water, and pass air to oxidize at 60 ℃ for 6h, add the diffusing agent NNO 150kg for sand grinding, spray drying to obtain the finished product.?Each batch is about 138kg (100%).?Method 2: Solvent method.?Add 15L of dimethyl sulfoxide and 6.802kg of 2-aminoanthraquinone to the condensation pot, and increase the temperature to 132℃ in about 1h. After the 2-aminoanthraquinone is basically dissolved, continue to increase the temperature to 130-150℃ for 30min to make it completely dissolved .?At this time, the heating was stopped, the air was introduced, the temperature dropped to about 128°C, and 4.4 L of potassium hydroxide solution (39.8%) was added within 10 minutes.?And continue to ventilate, keep the reaction at (125±2)℃ for 4h.?Then add 20L of water, the temperature of the material drops to about 80°C and filter, wash the condensation pot with 40L of water at 50-60°C, wash the filter cake with it, and pump to dry.?Add 380L of water to the refining pot, beat the above filter cake for 1h, add 27kg of alkali (43% sodium hydroxide), heat up to 56-57℃, add 5.44kg of insurance powder (85%), keep the temperature for 20min, and then within 40min Cool to 52℃, crystallize out, filter, filter cake is washed with water at about 50℃ [410L water, 5.8kg sodium hydroxide (43%), 0.82kg insurance powder (85%) preparation], then wash with water .?Add 100L of water to the acidizing pot, add the refined filter cake, beat for 2h, add water to adjust the volume to 200L, add sulfuric acid to adjust the pH to 2-3 (approximately 12.34% sulfuric acid 10kg).?Stir for 20 minutes and filter, wash to neutrality with water, and blow dry.?The finished product is obtained by sanding.

3.3 Purification Methods: Crystallise indanthrene repeatedly from 1,2,4-trichlorobenzene to give a blue powder. It is soluble in alkali and conc H2SO4. [Weinstein & Merritt J Am Chem Soc 81 3759 1959, Beilstein 24 II 317, 24 III/IV 2193.] Vat Blue 4 Preparation Products And Raw materials Raw materials

3.4 Usage: Mainly to dye cotton.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R20/21/22

4.1 Safety Statements: 22-36/37/39

4.1 Fire Hazard: Flash point data for Vat Blue 4 are not available. Vat Blue 4 is probably combustible.

4.2 Hazard Declaration: H413

4.2 RIDADR: CB8761100

4.2 Caution Statement: P273, P501

4.2 RTECS: CB8761100

4.2 Report: ?Vat Blue 4?is Reported in EPA TSCA Inventory.

4.3 Safety: Poison by intratracheal route. When heated to decomposition it emits toxic vapors of NO_x.
Risk Statements: 20/21/22?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37/39?
S22: Do not breathe dust.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RTECS of Vat Blue 4 (CAS NO.81-77-6): CB8761100

4.4 Specification: ? Vat Blue 4 (CAS NO.81-77-6), its Synonyms are Indanthrene ; 5,9,14,18-Anthrazinetetrone, 6,15-dihydro- ; 6,15-Dihydro-5,9,14,18-anthrazinetetrone ; C.I. Pigment Blue 60 ; Anthraquinone Blue ; Anthraquinone Deep Blue ; Blue anthraquinone pigment ; Indanthren Blue ;?Indanthrene blue RS?. It is blue needles with a metallic lustre.

4.5 Toxicity: LD50 oral in rat: 2gm/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

81-77-6Total: 29 Synthesis Route

82-45-1 125 Suppliers

81-77-6 132 Suppliers

Literatures:
Kuenstl. organ. Farbstoffe , S. 594 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 218 DE161923 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 344
Yield: null

222-64-0

81-77-6 132 Suppliers

Literatures:
Chemische Berichte, , vol. 36, p. 3443,3444
Yield: null

117-79-3 72 Suppliers

81-77-6 132 Suppliers

Literatures:
US1895203 , ; DE548263 , ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 2029
Yield: null

View all

7. Precursor and Product

precursor:

60245-50-3

24044-24-4

90-13-1

82-27-9

222-64-0

117-79-3

7732-18-5

121-69-7

6370-80-5

6374-73-8

91-20-3

5702-54-5

86-57-7

3300-23-0

82-45-1

3635-29-8

100-63-0

861520-91-4

108-95-2

142-71-2

View all

product :

130-20-1

6259-70-7

8. Other Information

8.0 Storage Conditions: Method 1: Melting method.?Using 2-aminoanthraquinone as raw material, after melting with warm alkali and alkali, the product is refined with insurance powder solution.?Or using 2-aminoanthraquinone as the raw material, dimethyl sulfoxide as the solvent, and performing alkaline fusion reaction with potassium hydroxide, and then refining the insurance powder solution to obtain the product.?.?Add 595 kg of anhydrous mixed alkali (68% of potassium hydroxide) to the condensation pot. After heating and melting, add 131 kg of sodium acetate (98%) and 1.5 kg of oleic acid (industrial product).?Close the condensation pot and heat to 185-190°C. At the same time, drive the air with nitrogen to keep the reaction liquid under the protection of nitrogen. Add 263kg of 2-aminoanthraquinone within 30min, control the temperature not to exceed 215°C, add heat for 1h, then add 25kg sodium nitrite (98%), the control temperature should not exceed 230℃, and it should be added within 2 hours.?Continue stirring for 20 min to complete the alkali melting reaction.?Put 5000L of water in the refining pot, drive the air with nitrogen, put in the alkali molten material, and stir for 2h; cool down to about 51℃, add 110kg of safety powder, and stir slowly. When the temperature is lowered to 45℃, crystals will precipitate.?Filter, the filter cake is washed with an aqueous solution of safety powder (the washing water is made up of 20L liquid alkali, 20kg insurance powder, and 5000L water), and then washed with warm water at 45°C until the filtrate is bluish, and dried to obtain a dye leuco wet material .?Add the dye leuco body wet material to the beating machine, beat with appropriate amount of water, and pass air to oxidize at 60 ℃ for 6h, add the diffusing agent NNO 150kg for sand grinding, spray drying to obtain the finished product.?Each batch is about 138kg (100%).?Method 2: Solvent method.?Add 15L of dimethyl sulfoxide and 6.802kg of 2-aminoanthraquinone to the condensation pot, and increase the temperature to 132℃ in about 1h. After the 2-aminoanthraquinone is basically dissolved, continue to increase the temperature to 130-150℃ for 30min to make it completely dissolved .?At this time, the heating was stopped, the air was introduced, the temperature dropped to about 128°C, and 4.4 L of potassium hydroxide solution (39.8%) was added within 10 minutes.?And continue to ventilate, keep the reaction at (125±2)℃ for 4h.?Then add 20L of water, the temperature of the material drops to about 80°C and filter, wash the condensation pot with 40L of water at 50-60°C, wash the filter cake with it, and pump to dry.?Add 380L of water to the refining pot, beat the above filter cake for 1h, add 27kg of alkali (43% sodium hydroxide), heat up to 56-57℃, add 5.44kg of insurance powder (85%), keep the temperature for 20min, and then within 40min Cool to 52℃, crystallize out, filter, filter cake is washed with water at about 50℃ [410L water, 5.8kg sodium hydroxide (43%), 0.82kg insurance powder (85%) preparation], then wash with water .?Add 100L of water to the acidizing pot, add the refined filter cake, beat for 2h, add water to adjust the volume to 200L, add sulfuric acid to adjust the pH to 2-3 (approximately 12.34% sulfuric acid 10kg).?Stir for 20 minutes and filter, wash to neutrality with water, and blow dry.?The finished product is obtained by sanding.

8.1 Experimental Properties: DECOMPOSES @ 470-500 °C

8.2 Reactive Group: Amines, Phosphines, and Pyridines

8.3 Fire Hazards: Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

8.4 Nonfire Spill Response: SMALL SPILLS AND LEAKAGE: If you spill this chemical, dampen the solid spill material with 5% ammonium hydroxide, then transfer the dampened material to a suitable container. Use absorbent paper dampened with 5% ammonium hydroxide to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with 5% ammonium hydroxide followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)

8.5 Personal Protective Equipment: RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

8.6 First Aid: EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

8.7 Mesh Entry Terms: 6,15-dihydroanthrazine-5,9,14,18-terone

8.8 Production: 100,000 - 500,000 lb

8.9 Manufacturing Info: Paint and coating manufacturing|5,9,14,18-Anthrazinetetrone, 6,15-dihydro-: ACTIVE|VAT DYE DISCOVERED BY RENE BOHN (1901).|MOLECULE CONSISTS OF TWO ANTHRAQUINONE NUCLEI LINKED THROUGH TWO NH GROUPS. PREPN: BY FUSION OF BETA-AMINOANTHRAQUINONE WITH CAUSTIC POTASH IN PRESENCE OF POTASSIUM NITRATE.|AUTOMOTIVE PAINTS, PLASTICS, RUBBER, PRINTING INKS. MEETS ANSI Z 66.1 SPECIFICATIONS /INDANTHRENE BLUES/

8.10 Use Classification: Food Additives -> COLOUR; -> JECFA Functional Classes|Cosmetics -> Cosmetic colorant

9. Computational chemical data

Molecular Weight: 442.42176g/mol
Molecular Formula: C₂₈H₁₄N₂O₄
Compound Is Canonicalized: True
XLogP3-AA: 4.9
Exact Mass: 442.09535693
Monoisotopic Mass: 442.09535693
Complexity: 857
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 92.3
Heavy Atom Count: 34
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB7OAAAAAAAAAAAAAAAAAAAAAAAAAA8YMGDAAAAAADxVAAAHgAQAAAADAyBmAAwwILAAACIAqRSQACCAAAlAgAIiAEAdMgIYHrAlZGUIYhgkADIyccdicCeiAAAQAASACCQAASAACQAQAAAAAAAAA==