Anthraquinone CAS 84-65-1
Introduction：Basic information about Anthraquinone CAS 84-65-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Anthraquinone Basic information
| Product Name: | Anthraquinone |
| Synonyms: | Anthracenedione;ANTHRAQUINONE;CORBIT;CORBIT(R);GAUCHO BLE;Hoelite;AQ;Anthraquinone;9,10-Dioxoanthracene |
| CAS: | 84-65-1 |
| MF: | C14H8O2 |
| MW: | 208.21 |
| EINECS: | 201-549-0 |
| Product Categories: | Chloroanthraquine, etc.;Anthraquinones;Intermediates of Dyes and Pigments;AM to AQCarbonyl Compounds;A;Alphabetic;C13 to C14;Carbonyl Compounds;Ketones;AM to AQPesticides&Metabolites;A-BAlphabetic;Alpha sort;Others;Pesticides;Pesticides&Metabolites;84-65-1;1 |
| Mol File: | 84-65-1.mol |
Anthraquinone Chemical Properties
| Melting point | 284-286 °C (lit.) |
| Boiling point | 379-381 °C (lit.) |
| bulk density | 600kg/m3 |
| 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. |
| Major Application | food and beverages pharmaceutical |
| InChI | 1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H |
| InChIKey | RZVHIXYEVGDQDX-UHFFFAOYSA-N |
| SMILES | O=C1c2ccccc2C(=O)c3ccccc13 |
| 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 | TSCA listed |
| HS Code | 2914 61 00 |
| HazardClass | 9 |
| PackingGroup | III |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Carc. 1B Skin Sens. 1 |
| Hazardous Substances Data | 84-65-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
| Description | Anthraquinone is a combustible, light yellowto green crystalline solid. Molecular weight= 208.23;Boiling point= 380℃; Melting/Freezing point= 286℃(sublimes); Flash point= 185℃ (cc). NFPA 704 M HazardIdentification (based on NFPA-704 M Rating System):Health 0, Flammability 1, Reactivity 0. Very slightly solublein water; solubility=,13 mg/L at 22℃. |
| 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 | Non flammable |
| 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 affectsbirds by causing post-ingestional distress (40). Sometimes,ingestion of anthraquinone-treated food produces vomiting,but often vomiting does not occur and the bird just sitsquietly until the discomfort passes. Unlike methiocarb,anthraquinone doe not affect the bird’s nervous systemand does not immobilize affected birds. Presumably, theemetic response is produced through irritation of the gutlining, but the actual mechanism is unclear. It is clear,however, that anthraquinone is not a taste repellent orcontact irritant. Birds do not hesitate to eat treated food,and they exhibit no sign that treated food is unpalatableto them. The post-ingestional discomfort that results fromeating anthraquinone-treated food produces a conditionedaversion to that food type. Birds need to experience theadverse consequences before learning to avoid the protectedfood. Thus, it is not reasonable to expect losses tocease immediately upon application of the repellent. Therewill be some level of loss in the crop as the depredatingbirds acquire the learned avoidance response. |
| Safety Profile | Moderately toxic byintraperitoneal route. A mild allergen.Mutation data reported. Combustible whenexposed to heat or flame. To fight fire, usewater, foam, CO2, water spray or mist, drychemical. When heated to decomposition itemits acrid smoke and irritating fumes. |
| Toxicology | Based on present knowledge, anthraquinone, unlikethe “emodins” (hydroxyanthraquinone glycosides)from anthraquinone drugs , is biologicallycompletely “inert,” i.e., inactive, presumablyas a consequence of its insolubility inwater and lipids. There is no toxicologic information aboutanthraquinone. Even in the Toxic Substances List no LD50 is found for anthraquinone. In contrastto benzoquinone, which causes severe localirritation and is included in the list of occupationalhazards because of its damaging effect onthe cornea, a fine dust of anthraquinone to whichemulgators were added had no greater effect onthe eyes of rabbits than a talcum suspension, aswas shown in a BASF study. An MAK value of 10 mg/m3 was recommended; therefore, anthraquinone dust isconsidered the same as inert dust. |
| Synthesis | Anthraquinone is produced from anthracene,where this is available from coal tar, either by oxidationwith chromic acid in 48 % sulfuric acidor by oxidation with air in the vapor phase. Theoxidation with chromic acid is competitive, providedthat the chromium(III) sulfate lye formedcan be processed to tanning agents. Anthracenewith purity of '94 % is required for both oxidationprocesses; crude anthracene from coal tarmust be purified by recrystallization. About 85 % of world production is basedon the oxidation of anthracene. Since the mid-1970s, anthracene production has fallen continuously,creating a supply shortage. Therefore, thecomplex naphthalene process is gaining in importance.There is an adequate supply of naphthalenein coal tar. If necessary, additional naphthalenecan be isolated from the residual oils ofgasoline reforming, a process common in theUnited States. |
| Potential Exposure | Anthraquinone is an important startingmaterial for vat dye manufacture. Also used in makingorganics; and used as a bird repellent in seeds. |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions,including resuscitation mask) if breathing has stopped andCPR if heart action has stopped. Transfer promptly to amedical facility. When this chemical has been swallowed,get medical attention. Give large quantities of water andinduce vomiting. Do not make an unconscious person vomit. |
| storage | Color Code—Blue: Health Hazard/Poison: Store ina secure poison location. Prior to working with this chemicalyou should be trained on its proper handling and storage.Store in tightly closed containers in a cool, well-ventilatedarea away from oxidizers. Sources of ignition, such as smoking and open flames, are prohibited where this chemical isused, handled, or stored in a manner that could create apotential fire or explosion hazard. |
| 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 virtuallyinsoluble in water. It is not phytotoxic and does not inhibitgermination of rice seeds or growth of sprouts. It has verylow toxicity to birds and mammals, and it appears to beinnocuous to insects as well. There is no known hazardto nontarget species from repellent applications of FlightControl. |
| 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 materialwith a combustible solvent and burn in a chemical incineratorequipped with an afterburner and scrubber. All federal,state, and local environmental regulations must beobserved. |
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 |
