Anthraquinone Chemical Properties

Melting point:

284-286 °C (lit.)

Boiling point:

379-381 °C (lit.)

Density 

1.438

vapor density 

7.16 (vs air)

vapor pressure 

1 mm Hg ( 190 °C)

refractive index 

1.5681 (estimate)

Flash point:

365 °F

storage temp. 

no restrictions.

solubility 

0.00007g/l

form 

Powder

color 

Yellow-green to khaki to tan

Water Solubility 

<0.1 g/100 mL at 23 ºC

Merck 

14,687

BRN 

390030

Stability:

Stable. Incompatible with strong oxidizing agents. Combustible.

InChIKey

RZVHIXYEVGDQDX-UHFFFAOYSA-N

LogP

3.39-3.4 at 30℃

CAS DataBase Reference

84-65-1(CAS DataBase Reference)

IARC

2B (Vol. 101) 2013

NIST Chemistry Reference

9,10-Anthraquinone(84-65-1)

EPA Substance Registry System

Anthraquinone (84-65-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43-36/37/38

Safety Statements 

36/37-37/39-26-24

RIDADR 

3077

WGK Germany 

1

RTECS 

CB4725000

Autoignition Temperature

650 °C

TSCA 

Yes

HS Code 

2914 61 00

HazardClass 

9

PackingGroup 

III

Hazardous Substances Data

84-65-1(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 5000 mg/kg

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Anthraquinone Usage And Synthesis

Chemical Properties

Anthraquinone is a combustible, light yellow to green crystalline solid. Soluble in ethanol, ether and acetone, insoluble in water. It may be prepared by reacting benzene with phthalic anhydride. The compoundis the basis of a range ofdyestuffs.

Occurrence

Anthraquinones naturally occur in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where they serve as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative effects.

Uses

Anthraquinone is used in paper industry as a catalyst to increase the pulp production yield and to improves the fiber strength through reduction reaction of cellulose to carboxylic acid. It is also used as a precursor for dye formation.

Preparation

Anthraquinone is obtained by oxidation of anthracene using sodium dichromate plus sulfuric acid, and is purified by dissolving in concentrated sulfuric acid at 130 °C and pouring into boiling water, whereupon anthraquinone separates as pure solid, and is recovered by filtration. Further purification may be accomplished by sublimation or crystallization from nitrobenzene, aniline or tetrachloroethane.

Definition

ChEBI: Anthraquinone is an anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls. It is a colorless crystalline quinone used in producing dyestuffs such as alizarin.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 1457, 1980 DOI: 10.1021/ja00524a059
The Journal of Organic Chemistry, 29, p. 987, 1964 DOI: 10.1021/jo01027a538
Tetrahedron Letters, 24, p. 5499, 1983 DOI: 10.1016/S0040-4039(00)94122-4

General Description

Anthraquinone is a polycyclic aromatic hydrocarbon derived from anthracene or phthalic anhydride. Anthraquinone is used in the manufacture of dyes, in the textile and pulp industries, and as a bird repellant.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Anthraquinone is incompatible with strong oxidizing agents.

Hazard

Possible carcinogen.

Fire Hazard

Anthraquinone is combustible.

Flammability and Explosibility

Nonflammable

Agricultural Uses

Repellent, Seed treatment: Used as a seed dressing or protectant. Banned in EU.

Trade name

(p)ANTHRAPEL®; FLIGHT CONTROL- PLUS®; HOELITE®; MORKIT®; REPELL®

Pharmacology

Anthraquinone is a secondary repellent and affects birds by causing post-ingestional distress (40). Sometimes, ingestion of anthraquinone-treated food produces vomiting, but often vomiting does not occur and the bird just sits quietly until the discomfort passes. Unlike methiocarb, anthraquinone doe not affect the bird’s nervous system and does not immobilize affected birds. Presumably, the emetic response is produced through irritation of the gut lining, but the actual mechanism is unclear. It is clear, however, that anthraquinone is not a taste repellent or contact irritant. Birds do not hesitate to eat treated food, and they exhibit no sign that treated food is unpalatable to them. The post-ingestional discomfort that results from eating anthraquinone-treated food produces a conditioned aversion to that food type. Birds need to experience the adverse consequences before learning to avoid the protected food. Thus, it is not reasonable to expect losses to cease immediately upon application of the repellent. There will be some level of loss in the crop as the depredating birds acquire the learned avoidance response.

Safety Profile

Moderately toxic by intraperitoneal route. A mild allergen. Mutation data reported. Combustible when exposed to heat or flame. To fight fire, use water, foam, CO2, water spray or mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Anthraquinone is an important starting material for vat dye manufacture. Also used in making organics; and used as a bird repellent in seeds.

Shipping

UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise anthraquinone from CHCl3 (38mL/g), *benzene, or boiling acetic acid, wash it with a little EtOH and dry it under vacuum over P2O5. [Beilstein 7 IV 2556.]

Toxicity evaluation

Anthraquinone is a stable compound that is virtually insoluble in water. It is not phytotoxic and does not inhibit germination of rice seeds or growth of sprouts. It has very low toxicity to birds and mammals, and it appears to be innocuous to insects as well. There is no known hazard to nontarget species from repellent applications of Flight Control.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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