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Anthraquinone

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Anthraquinone Basic information
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. Storage temperature: 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.
  • InChIKeyRZVHIXYEVGDQDX-UHFFFAOYSA-N
  • CAS DataBase Reference84-65-1(CAS DataBase Reference)
  • IARC2B (Vol. 101) 2013
  • NIST Chemistry Reference9,10-Anthraquinone(84-65-1)
  • EPA Substance Registry SystemAnthraquinone (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 Temperature650 °C
  • TSCA Yes
  • HS Code 2914 61 00
  • HazardClass 9
  • PackingGroup III
  • Hazardous Substances Data84-65-1(Hazardous Substances Data)
  • ToxicityLD50 orally in Rabbit: > 5000 mg/kg
MSDS
Anthraquinone Usage And Synthesis
  • Chemical Propertiesdull yellow powder
  • Chemical PropertiesAnthraquinone is a combustible, light yellow to green crystalline solid.
  • Usesbird repellant, irritant
  • UsesA precursor for dye formation
  • UsesStarting material for the manufacture of dyes; bird repellent.
  • DefinitionChEBI: An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.
  • DefinitionA colorless crystalline quinone used in producing dyestuffs such as alizarin.
  • Definitionanthraquinone: A colourless crystallingquinone; m.p. 154°C. It maybe prepared by reacting benzenewith phthalic anhydride. The compoundis the basis of a range ofdyestuffs.
  • Production MethodsAnthraquinone 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.
  • 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 DescriptionYellow crystals or powder.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileAnthraquinone is incompatible with strong oxidizing agents.
  • HazardPossible carcinogen.
  • Fire HazardAnthraquinone is combustible.
  • Agricultural UsesRepellent, Seed treatment: Used as a seed dressing or protectant. Banned in EU.
  • Trade name(p)ANTHRAPEL®; FLIGHT CONTROL- PLUS®; HOELITE®; MORKIT®; REPELL®
  • PharmacologyAnthraquinone 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 ProfileModerately 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 ExposureAnthraquinone is an important starting material for vat dye manufacture. Also used in making organics; and used as a bird repellent in seeds.
  • ShippingUN3143 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 MethodsCrystallise 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 evaluationAnthraquinone 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.
  • IncompatibilitiesIncompatible 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 DisposalDissolve 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.
Anthraquinone Preparation Products And Raw materials
Anthraquinone(84-65-1)Related Product Information
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