1047-16-1

Basic information

• Product Name: Quinacridone
• Synonyms: 3-b)acridine-7,14-dione,5,12-dihydro-quino(;3-b]acridine-7,14-dione,5,12-dihydro-quino[;3-b]acridine-7,14-dione,5,12-dihydro-Quino[2;5,12-dihydroquino[2,3-;5,12-dihydroquino[2,3-b]acridine-7,14-;5,12-dihydroquino[2,3-b]acridine-7,14-dione(ci73900);C.I. 46500;C.I. Pigment Violet 19
• CAS NO: 1047-16-1
• Molecular Formula: C₂₀H₁₂N₂O₂
• Molecular Weight: 312.32
• EINECS: 213-561-3
• Product Categories: Electroluminescence;Functional Materials;Highly Purified Reagents;Other Categories;Refined Products by Sublimation
• Mol File: 1047-16-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 390 °C
• Boiling Point: 568.5 °C at 760 mmHg
• Flash Point: 221.3 °C
• Appearance: red powder
• Density: 1.371 g/cm³
• Vapor Pressure: 6.14E-13mmHg at 25°C
• Refractive Index: 1.702
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.96±0.20(Predicted)
• CAS DataBase Reference: Quinacridone(CAS DataBase Reference)
• NIST Chemistry Reference: Quinacridone(1047-16-1)
• EPA Substance Registry System: Quinacridone(1047-16-1)

Safety Data

• Safety Statements: 24/25
• RTECS: VA8533500
• Hazardous Substances Data: 1047-16-1(Hazardous Substances Data)

Usage

Chemical Properties

The parent compound Pigment Violet 19 exists in three polymorphic modifications. The red gamma and violet beta forms are commercial pigments, whereas the red alpha form is metastable.

Definition

A lightfast pigment used in paints, printing inks, plastics, etc.

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE VIOLET POWDER SHADE BLUISH HEAT RESISTANCE 300 °C min LIGHT FASTNESS 7-8 ACID RESISTANCE 5 ALKALI RESISTANCE 5 FASTNESS TO BLEEDING 5 OIL ABSORPTION 40-50% SPECIFIC SURFACE 30 m 2 /g DENSITY 1.50 g/cm 3 RESIDUE ON 80 MESH 5.0% max WATER SOLUBLE 1.0% max VOLATITE 105 °C 1.0% max TINTING STRENGTH 100-105 %

TEST ITEMS

SPECIFICATION

APPEARANCE

VIOLET POWDER

SHADE

BLUISH

HEAT RESISTANCE

300 °C min

LIGHT FASTNESS

7-8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

OIL ABSORPTION

40-50%

SPECIFIC SURFACE

30 m 2 /g

DENSITY

1.50 g/cm 3

RESIDUE ON 80 MESH

5.0% max

WATER SOLUBLE

1.0% max

VOLATITE 105 °C

1.0% max

TINTING STRENGTH

100-105 %

InChI:InChI=1/C20H12N2O2/c23-19-11-5-1-3-7-15(11)21-17-10-14-18(9-13(17)19)22-16-8-4-2-6-12(16)20(14)24/h1-10H,(H,21,23)(H,22,24)

Synthetic route

2,5-di(phenylamino)-terephthalic acid (10109-95-2) → Quinacridone (1047-16-1)

Conditions	Yield
With polyphosphoric acid PPA at 125℃; for 6h; Dieckmann Condensation;	99.43%
With PPA at 20 - 130℃; for 1.5h; Product distribution / selectivity;	90%
With boric acid

5,6,12,13-tetrahydro-quino[2,3-b]acridine-7,14-dione (5862-38-4) → Quinacridone (1047-16-1)

Conditions	Yield
Stage #1: 5,6,12,13-tetrahydro-quino[2,3-b]acridine-7,14-dione With sodium hydroxide In methanol; water at 20 - 30℃; for 0.5h; Stage #2: With sulfuric acid In methanol; water for 1h; Heating / reflux; Stage #3: With sodium 3-nitrobenzenesulfonate In methanol; water for 4h; Product distribution / selectivity; Heating / reflux;	99%
Stage #1: 5,6,12,13-tetrahydro-quino[2,3-b]acridine-7,14-dione With sodium methylate In methanol at 20 - 50℃; for 0.25h; Stage #2: With sodium 3-nitrobenzenesulfonate In methanol for 4h; Product distribution / selectivity; Heating / reflux;	98%
Stage #1: 5,6,12,13-tetrahydro-quino[2,3-b]acridine-7,14-dione With polyvinyl pyrrolidone In methanol at 20 - 27℃; for 0.166667h; Stage #2: With sodium hydroxide In methanol; water at 50 - 53℃; for 0.833333h; Heating / reflux; Stage #3: With dihydrogen peroxide; anthraquinone-2,7-disulfonic acid In methanol; water for 0.166667h; Product distribution / selectivity; Heating / reflux;

2,5-dianilino-3,6-dihydroterephthalic acid diethyl ester (4898-56-0) → Quinacridone (1047-16-1)

Conditions	Yield
With diphenylether; biphenyl Erhitzen des Reaktionsprodukts mit dem Natrium-Salz der 3-Nitro-benzolsulfonsaeure in wss. NaOH und Aethylenglykol;
With diphenylether; biphenyl Erhitzen des Reaktionsprodukts mit dem Natrium-Salz der 3-Nitro-benzolsulfonsaeure in wss.-aethanol. NaOH;

C21H18N2O4 (67906-32-5) + 2,5-di(phenylamino)-terephthalic acid (10109-95-2) + 2,5-di(4'-methylphenylamino)terephthalic acid (10291-28-8) → Quinacridone (1047-16-1) + C.I. Pigment Red 122 (980-26-7) + 5,12-dihydro-2-methylquino[2,3-b]acridine-7,14-dione (10228-01-0)

Conditions	Yield
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;

6,13-dihydroquinacridone-di-sodium salt → Quinacridone (1047-16-1)

Conditions	Yield
Stage #1: 6,13-dihydroquinacridone-di-sodium salt With dihydrogen peroxide; anthraquinone-2,7-disulphonic acid disodium salt In methanol; water at 20 - 60℃; for 0.25h; Heating / reflux; Stage #2: In water

2,5-dianilinoterephthalic acid dimethyl ester (14297-60-0) → Quinacridone (1047-16-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / 3 h / 110 °C / Reflux 2: polyphosphoric acid PPA / 6 h / 125 °C View Scheme

2,5-di(phenylamino)-terephthalic acid (10109-95-2) + C22H17N3O3 → Quinacridone (1047-16-1) + C21H13N3O2

Conditions	Yield
With polyphosphoric acid at 120 - 130℃; for 2h;

p-formaldehyde + Quinacridone (1047-16-1) + 3,4,9,10-perylene tetracarboxyxlic acid diimide (81-33-4) → C66H34N6O8

Conditions	Yield
Stage #1: p-formaldehyde; 3,4,9,10-perylene tetracarboxyxlic acid diimide With polyphosporic acid at 105℃; for 1.5h; Stage #2: Quinacridone at 125℃; for 3h;	100%
Stage #1: p-formaldehyde; 3,4,9,10-perylene tetracarboxyxlic acid diimide With sulfuric acid at 45℃; for 1h; Stage #2: Quinacridone at 45℃; for 3h;	99.7%
Stage #1: p-formaldehyde; 3,4,9,10-perylene tetracarboxyxlic acid diimide With sulfuric acid; sulfur trioxide at 45℃; for 1h; Stage #2: Quinacridone at 45℃; for 3h;	89%

di-tert-butyl dicarbonate (24424-99-5) + Quinacridone (1047-16-1) → N,N-di(tert-butylcarboxyl)-trans-quinacridone

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; regioselective reaction;	99%
With dmap In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;	65.5%
With dmap In tetrahydrofuran at 20℃; for 24h;	60%
With dmap In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; Darkness;	58%
With dmap In dichloromethane at 20℃; for 48h; Inert atmosphere;	56%

Quinacridone (1047-16-1) + chloroacetyl chloride (79-04-9) → 2,9-dichloroacetylquinacridone

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 24h;	97%

1-tert-butyl-4-iodobenzene (35779-04-5) + Quinacridone (1047-16-1) → N,N'-bis(4-tert-butylphenyl)quinacridone

Conditions	Yield
With copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; potassium carbonate In N,N-dimethyl-formamide at 146℃; for 36h; Inert atmosphere;	96%

4-Iodobenzotrifluoride (455-13-0) + Quinacridone (1047-16-1) → N,N'-bis(4-trifluoromethylphenyl)quinacridone

Conditions	Yield
With copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; potassium carbonate In N,N-dimethyl-formamide at 146℃; for 36h; Inert atmosphere;	96%

Quinacridone (1047-16-1) + Methyl benzenesulfonate (80-18-2) → 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,14-dione (19205-19-7)

Conditions	Yield
With sodium hydroxide; benzyltrimethylammonium chloride In chlorobenzene at 80℃; for 7h; Product distribution; other base, other solvent, with or without phase transfer;	94%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In chlorobenzene at 80℃; for 7h;	94%

para-iodoanisole (696-62-8) + Quinacridone (1047-16-1) → 5,12-bis(4-methoxyphenyl)quinolino[2,3-b]acridine-7,14(5H,12H)-dione

Conditions	Yield
With copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; potassium carbonate In N,N-dimethyl-formamide at 146℃; for 36h; Inert atmosphere;	94%

Ethyl benzenesulfonate (515-46-8) + Quinacridone (1047-16-1) → N,N'-Diethylquinacridone (99762-78-4)

Conditions	Yield
With sodium hydroxide; cetyltrimethylammonium chloride In water; chlorobenzene at 80℃; for 10h;	92%
With sodium hydroxide; cetyltrimethylammonium chloride In water; chlorobenzene at 80℃; for 5h; Product distribution; different reactant-reagent ratios, different reaction time;	87%

Quinacridone (1047-16-1) + dimethyl sulfate (77-78-1) → 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,14-dione (19205-19-7)

Conditions	Yield
With sodium hydroxide; quaternary ammonium salt In chlorobenzene at 80℃; for 5h; Product distribution; other base, other solvent, with or without phase transfer;	92%
With sodium hydroxide; alkyl(C10-C16)-trimethylammonium chloride In chlorobenzene at 80℃; for 5h;	92%

Quinacridone (1047-16-1) + methyl iodide (74-88-4) → 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,14-dione (19205-19-7)

Conditions	Yield
With potassium hydroxide In various solvent(s) at 80℃; for 6h; Product distribution; other base, other solvent, with or without phase transfer;	92%
With potassium hydroxide In various solvent(s) at 80℃; for 6h;	92%
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In toluene for 10h; Reflux;	25%

Quinacridone (1047-16-1) + ethyl ester of p-toluenesulfonic acid (80-40-0) → N,N'-Diethylquinacridone (99762-78-4)

Conditions	Yield
With sodium hydroxide; cetyltrimethylammonium chloride In water; chlorobenzene at 80℃; for 12h;	91%

1-bromo-octane (111-83-1) + Quinacridone (1047-16-1) → 5,12-dihydroquino<2,3-b>acridine-7,14-dione

Conditions	Yield
With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran Inert atmosphere;	91%
With tetrabutylammomium bromide; caesium carbonate In dimethyl sulfoxide at 25℃; for 4h; Solvent; Reagent/catalyst;	85%
Stage #1: Quinacridone With tetrabutylammomium bromide; caesium carbonate In dimethyl sulfoxide at 20℃; for 4h; Stage #2: 1-bromo-octane In dimethyl sulfoxide for 24h;	82%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride In mineral oil; benzene at 20℃; for 174h;	64%
With tetrabutylammomium bromide; sodium hydroxide In toluene for 24h; Reflux;	24.9%

diethyl sulfate (64-67-5) + Quinacridone (1047-16-1) → N,N'-Diethylquinacridone (99762-78-4)

Conditions	Yield
With sodium hydroxide; cetyltrimethylammonium chloride In water; chlorobenzene at 80℃; for 7h;	90%

Quinacridone (1047-16-1) + ethyl iodide (75-03-6) → N,N'-Diethylquinacridone (99762-78-4)

Conditions	Yield
With sodium hydroxide; cetyltrimethylammonium chloride In water; chlorobenzene at 80℃; for 13h;	89%

1-bromo-butane (109-65-9) + Quinacridone (1047-16-1) → N,N’-dibutylquinacridone (99762-80-8)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 80℃; for 12h;	87%
Stage #1: Quinacridone With tetrabutylammomium bromide; potassium hydroxide In water; toluene at 95℃; Stage #2: 1-bromo-butane In water; toluene at 95℃; for 24h;	80%

3,5-di-tert-butylbenzyl bromide (62938-08-3) + Quinacridone (1047-16-1) → 5,12-bis-(3,5-di-tert-butyl-benzyl)-5,12-dihydro-quino[2,3-b]acridine-7,14-dione

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water; toluene for 4h; Heating;	87%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene at 80℃; for 32h;	76%

Quinacridone (1047-16-1) + benzyl chloride (100-44-7) → 5,12-Dibenzyl-5,12-dihydro-quino[2,3-b]acridine-7,14-dione (99762-81-9)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 80℃; for 11h;	85%

1-bromo dodecane (112-29-8) + Quinacridone (1047-16-1) → N,N′-didecylquinacridone

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; for 24h;	85%

Quinacridone (1047-16-1) + 1-dodecylbromide (143-15-7) → C44H60N2O2

Conditions	Yield
Stage #1: Quinacridone With tetrabutylammomium bromide; caesium carbonate In dimethyl sulfoxide at 20℃; for 4h; Stage #2: 1-dodecylbromide In dimethyl sulfoxide at 20 - 90℃; for 26h; Concentration; Reagent/catalyst;	84%
Stage #1: Quinacridone With tetrabutylammomium bromide; caesium carbonate In dimethyl sulfoxide at 30℃; for 4h; Stage #2: 1-dodecylbromide In dimethyl sulfoxide at 20 - 90℃; for 26h;	80%

Quinacridone (1047-16-1) + 1-chloro-2-(chloromethyl)benzene (611-19-8) → 5,12-Bis-(2-chloro-benzyl)-5,12-dihydro-quino[2,3-b]acridine-7,14-dione (99762-82-0)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 80℃; for 12h;	82%

Quinacridone (1047-16-1) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → 5,12-Bis-(4-chloro-benzyl)-5,12-dihydro-quino[2,3-b]acridine-7,14-dione (99762-83-1)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 80℃; for 9h;	81%

Quinacridone (1047-16-1) + 4-Methylbenzyl chloride (104-82-5) → 5,12-Bis-(4-methyl-benzyl)-5,12-dihydro-quino[2,3-b]acridine-7,14-dione (99762-84-2)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 80℃; for 10h;	80%

6-bromo-hexanoic acid ethyl ester (25542-62-5) + Quinacridone (1047-16-1) + methyl iodide (74-88-4) → ethyl 6-(12-methyl-7,14-dioxo-12,14-dihydroquinolino[2,3-b]acridin-5(7H)-yl)hexanoate

Conditions	Yield
Stage #1: Quinacridone With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 60℃; for 0.666667h; Stage #2: 6-bromo-hexanoic acid ethyl ester In dimethyl sulfoxide; N,N-dimethyl-formamide for 8h; Stage #3: methyl iodide In dimethyl sulfoxide; N,N-dimethyl-formamide	78%

Quinacridone (1047-16-1) + 1,3-bis{[3,5-bis(tert-butyl)benzyl]oxy}-5-(bromomethyl)benzene (213680-85-4) → 5,12-bis-[3,5-bis-(3,5-di-tert-butyl-benzyloxy)-benzyl]-5,12-dihydro-quino[2,3-b]acridine-7,14-dione

Conditions	Yield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene at 80℃; for 32h;	76%
With potassium hydroxide; tetrabutylammomium bromide In water; toluene for 4h; Heating;	74%

1,3-propanesultone (1120-71-4) + Ph4PCl + Quinacridone (1047-16-1) → 2C24H20P(1+)*C26H22N2O8S2(2-)

Conditions	Yield
Stage #1: 1,3-propanesultone; Quinacridone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; Stage #2: Ph4PCl In water	75%

1-iodo-butane (542-69-8) + Quinacridone (1047-16-1) → N,N’-dibutylquinacridone (99762-80-8)

Conditions	Yield
Stage #1: Quinacridone With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; for 2h; Stage #2: 1-iodo-butane In dimethyl sulfoxide at 80℃; for 6h; Inert atmosphere;	75%

Quinacridone (1047-16-1) + C98H80O24S6(6-)*6Na(1+) → 2C20H12N2O2*C98H80O24S6(6-)*6Na(1+)

Conditions	Yield
In water at 20℃; for 0.666667h; Sonication;	70%

1-Iodooctane (629-27-6) + Quinacridone (1047-16-1) → 5,12-dihydroquino<2,3-b>acridine-7,14-dione

Conditions	Yield
Stage #1: Quinacridone With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; for 2h; Stage #2: 1-Iodooctane In dimethyl sulfoxide at 80℃; for 6h; Inert atmosphere;	70%

Upstream product

• 4898-56-0 2,5-dianilino-3,6-dihydroterephthalic acid diethyl ester 
• 10109-95-2 2,5-di(phenylamino)-terephthalic acid 
• 14297-60-0 2,5-dianilinoterephthalic acid dimethyl ester 
• 5862-38-4 5,6,12,13-tetrahydro-quino[2,3-b]acridine-7,14-dione 
• 67906-32-5 C₂₁H₁₈N₂O₄ 
• 10291-28-8 2,5-di(4'-methylphenylamino)terephthalic acid 

Downstream Products

• 99762-80-8 N,N’-dibutylquinacridone 
• 1414782-64-1 2-cyano-3-(5-{9-[4-(bis(4-methoxyphenyl)amino)phenyl]-5,12-dioctyl-7,14-dioxo-5,7,12,14-tetrahydroquinolino[2,3-b]acridin-2-yl}furan-2-yl)acrylic acid 
• 1414782-63-0 2-cyano-3-(5-{9-[(E)-4-(diphenylamino)styryl]-5,12-dioctyl-7,14-dioxo-5,7,12,14-tetrahydroquinolino[2,3-b]acridin-2-yl}furan-2-yl)acrylic acid 

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Relevant articles and documents

QUINACRIDONE SOLID SOLUTION PIGMENT, PIGMENT COLORANT, INKJET INK, AND METHOD OF PRODUCING SOLID SOLUTION PIGMENT

PROBLEM TO BE SOLVED: To provide: a quinacridone solid solution pigment which has a new color tone, an excellent pigment characteristic and a novel skeleton; and a pigment colorant and an inkjet ink that employ the same. SOLUTION: A quinacridone solid solution pigment is a solid solution of a compound represented by the specified general formula (1) and a quinacridone represented by the specified general formula (2). Also provided are a method of producing the same, and a colorant and an inkjet ink that contain the solid solution pigment. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

METHOD FOR MANUFACTURING DISPERSION OF QUINOLINE DERIVATIVE

A method for manufacturing a dispersion of a quinoline derivative that is dispersed at a high concentration and has a small particle size. The method includes the steps of preparing a solution by dissolving an N-arylanthranilic acid derivative in an organosulfonic acid, heating the solution and obtaining a reaction liquid in which a quinoline derivative has been produced by a condensation ring-closing reaction, and obtaining a dispersion of the quinoline derivative by mixing the reaction liquid with an aqueous solution. The step of mixing the reaction liquid with an aqueous solution may be performed in a mixing field having a micro-channel.

PROCESS FOR THE PREPARATION OF ORGANIC PIGMENTS

The present invention relates to advantageous processes for the manufacture of organic pigments and their precursors. The invention particularly relates to reactions carried out in an "All In One Reactor" (Draiswerke GmbH, Germany), a kneader like the TurbuKneader of the same company, a paddle dryer like the Turbudry of the same company or a related system and thereby submitting the reaction mixtures to enhanced driving power as expressed by a Froude number>1, the reaction mixture being caused to react in high concentrations at elevated temperature.