|
| | 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) | | Fp | 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) |
| | 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. |
| | Anthraquinone Preparation Products And Raw materials |
| Raw materials | Sulfuric acid-->Benzene-->Aluminum chloride-->Phthalic anhydride-->Sodium dichromate dihydrate-->CARBON MONOXIDE-->Styrene-->Nicotinic acid-->COAL TAR-->Vanadium(V) oxide-->Anthracene-->1,2,4-Trichlorobenzene-->Aluminium silicon-->Oxyanthraquinone | | Preparation Products | Hydrogen peroxide-->1-Aminoanthraquinone-->Benzanthrone-->2-Bromoanthraquinone-->Vat Green 3-->Disperse Blue 56-->1-Chloro anthraquinone-->Anthrone-->1 5-DINITROANTHRAQUINONE 97-->Alizarin-->Ethyl Hexanoate-->Benzoic acid, 5-4-4-4-(4-amino-9,10-dihydro-9,10-dioxo-3-sulfo-1-anthracenyl)amino-2-sulfophenylamino-6-(phenylamino)-1,3,5-triazin-2-ylaminophenylazo-2-hydroxy-, trisodium salt-->1-Anthraquinonesulfonic acid-->2,6-Diaminoanthraquinone-->1,8-DINITROANTHRAQUINONE-->9,10-DIMETHYLANTHRACENE-->1 5-ANTHRAQUINONEDISULFONIC ACID-->1,5-DIAMINOANTHRAQUINONE-->2-Anthraquinonesulfonic acid-->9,10-dioxoanthracene-1,8-disulphonic acid-->2,3-DIMETHYLANTHRAQUINONE-->1,5-DICHLOROANTHRAQUINONE-->1,4,5,8-Tetrachloroanthraquinone |
|
