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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.

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/ja00524a059The Journal of Organic Chemistry, 29, p. 987, 1964 DOI: 10.1021/jo01027a538Tetrahedron Letters, 24, p. 5499, 1983 DOI: 10.1016/S0040-4039(00)94122-4

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?

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.

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.