Anthraquinone


Anthraquinone
9,10-Anthraquinone
Identifiers
CAS number 84-65-1 YesY
ChemSpider 6522 YesY
KEGG C16207 YesY
ChEMBL CHEMBL55659 N
Jmol-3D images Image 1
Properties
Molecular formula C14H8O2
Molar mass 208.21 g mol−1
Appearance yellow solid
Density 1.308g/cm3
Melting point

286 °C

Boiling point

379.8 °C

Solubility in water Insoluble
Hazards
R-phrases R36/37/38
Flash point 185°C
Related compounds
Related compounds quinone,
anthracene
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Anthraquinone, also called anthracenedione or dioxoanthracene is an aromatic organic compound with formula C14H8O2. Several isomers are possible, each of which can be viewed as a quinone derivative. The term anthraquinone, however, almost invariably refers to one specific isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. For instance, it is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol.

Contents

Synthesis

9,10-Anthraquinone is obtained industrially by the oxidation of anthracene, a reaction that is localized at the central ring. Chromium(VI) is the typical oxidant. It is also prepared by the Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone. This reaction is useful for producing substituted anthraquinones. The Diels-Alder reaction of naphthoquinone and butadiene followed by oxidative dehydrogenation will also produce 9,10-anthraquinone. Lastly, BASF has developed a process that proceeds via the acid-catalyzed dimerization of styrene to give a 1,3-diphenylbutene, which then can be transformed to the anthaquinone.[1] It also arises via the Rickert-Alder reaction, a retro-Diels-Alder reaction.

In a classic (1905) organic reaction called the Bally-Scholl synthesis, named after Oscar Bally and Roland Scholl, anthraquinone condenses with glycerol forming benzanthrone.[2] In this reaction, the quinone is first reduced with copper metal in sulfuric acid (converting one ketone group into a methylene group) after which the glycerol is added.

Bally-Scholl Synthesis

Applications and natural occurrence

Dyestuff precursor

Synthetic dyes are often derived from 9,10-anthraquinone, such as alizarin.[3] Important derivatives are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the dinitroanthraquinone.[1] Natural pigments that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and some insects.

Selection of anthraquinone dyes. From the left: C.I.Acid Blue 43 an "acid dye" for wool (also called "Acilan Saphirol SE"), C.I. Vat Violet 1, which is applied by transfer printing using sublimation, a blue colorant commonly used in gasoline, and C.I. Disperse Red 60, a so-called vat dye.

Digester additive in papermaking

According to Dr. Bryle Kristopher Cavalencia, 9,10-Anthraquinone is used as a digester additive in production of paper pulp by alkaline processes, like the Kraft, the alkaline sulfite or the Soda-AQ processes. The anthraquinone is a redox catalyst. The reaction mechanism may involve single electron transfer (SET).[4] The antraquinone is oxidizing cellulose and thereby protecting it from alkaline degradation (peeling). The anthraquinone is reduced to 9,10-dihydroxyanthracene which then can react with lignin. The lignin is degraded and becomes more watersoluble and thereby more easy to wash away from the pulp, while the antraquinone is regenerated. This process gives an increase in yield of pulp, typically 1-3 % and a reduction in kappa number.[5]

Sodium 2-anthraquinonesulfonate (AMS) is a watersoluble anthraquinone derivative that was the first anthraquinone derivative discovered to have a catalytic effect in the alkaline pulping processes.[6]

In the production of hydrogen peroxide

A large industrial application of anthraquinones is for the production of hydrogen peroxide. 2-Ethyl-9,10-anthraquinone or a related alkyl derivatives is used, rather anthraquinone itself.[7]

Catalytic hydrogen peroxide production with the anthraquinone process

Medicine

Derivatives of 9,10-anthraquinone include many important drugs (collectively called anthracenediones). They include

Aloe emodin.svg Mitoxantrone skeletal.svg Pixantrone.svg
Aloe emodin Mitoxantrone Pixantrone

Niche uses

9,10-Anthraquinone is used as a bird repellant on seeds and as a gas generator in satellite balloons. [8]

Natural anthraquinone derivatives tend to have laxative effects. Prolonged use and abuse leads to melanosis coli.[9][10] 5 anthraquinones have been shown to inhibit the formation of Tau aggregates and dissolve paired helical filaments thought to be critical to Alzheimer's disease progression in both mouse models and in vitro testing but have not been investigated as a therapeutic agent. [11]

Other isomers

Several other isomers of anthraquinone are possible, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of comparatively minor importance. The term is also used in the more general sense of any compound that can be viewed as an anthraquinone with some hydrogen atoms replaced by other atoms or functional groups. These derivatives include substances that are technically useful or play important roles in living beings.

See also

References

  1. ^ a b Axel Vogel "Anthraquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_347
  2. ^ Macleod L.C., Allen C.F.H. (1943), "Benzathrone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0062 ; Coll. Vol. 2: 62 
  3. ^ Hans-Samuel Bien, Josef Stawitz, Klaus Wunderlich “Anthraquinone Dyes and Intermediates” Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinhem. doi:10.1002/14356007.a02_355
  4. ^ Samp, James Christian (2008). A comprehensive mechanism for anthraquinone mass transfer in alkaline pulping. Georgia Institute of Technology. p. 30. http://gradworks.umi.com/33/27/3327651.html 
  5. ^ Sturgeoff, L.G.; Pitl, Y. (1997) [1993]. Goyal, Gopal C.. ed. Low Kappa pulping without capital investment. 3–9. ISBN 0-89852-340-0 
  6. ^ "Anthraquinone/ alkali pulping. A literature review" 7 1978 http://smartech.gatech.edu/bitstream/1853/673/1/3370_001_071978.pdf 
  7. ^ Gustaaf Goor, Jürgen Glenneberg, Sylvia Jacobi "Hydrogen Peroxide" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a13_443.pub2.
  8. ^ www.americanheritage.com
  9. ^ Müller-Lissner SA (1993). "Adverse effects of laxatives: fact and fiction". Pharmacology 47 (Suppl 1): 138–45. doi:10.1159/000139853. PMID 8234421. 
  10. ^ Moriarty KJ, Silk DB (1988). "Laxative abuse". Dig Dis 6 (1): 15–29. doi:10.1159/000171181. PMID 3280173. 
  11. ^ [1].

External links


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Look at other dictionaries:

  • anthraquinone — [ ɑ̃trakinɔn ] n. f. • 1878; de anthra(cène) et quinone ♦ Chim. Produit de l oxydation de l anthracène, employé dans la fabrication de colorants. ● anthraquinone nom féminin Composé de formule C14H8O2, obtenu pour la première fois en 1835 par… …   Encyclopédie Universelle

  • Anthraquinone — An thra*qui none, n. [Anthracene + quinone.] (Chem.) A hydrocarbon, {C6H4.C2O2.C6H4}, subliming in shining yellow needles. It is obtained by oxidation of anthracene. [1913 Webster] …   The Collaborative International Dictionary of English

  • anthraquinone — [an΄thrə kwi nōn′, an΄thrəkwin′ōn΄] n. [ ANTHRA(CENE) + QUINONE] a yellow crystalline ketone, C6H4 (CO) 2C6H4, produced from anthracene by oxidation or the reaction of phthalic anhydride with benzene: it is used in the manufacture of certain dyes …   English World dictionary

  • Anthraquinone — Traduction à relire Anthraquinone → Anthraqui …   Wikipédia en Français

  • anthraquinone — /an threuh kweuh nohn , kwee nohn, kwin ohn/, n. Chem. a yellow, water insoluble, crystalline powder, C14H8O2, usually derived from anthracene or phthalic anhydride: used chiefly in the manufacture of anthraquinone dyes. [1880 85; ANTHRA(CENE) +… …   Universalium

  • anthraquinone — antrachinonas statusas T sritis chemija formulė C₆H₄(CO)₂C₆H₄ atitikmenys: angl. anthraquinone rus. антрахинон ryšiai: sinonimas – 9,10 antracendionas …   Chemijos terminų aiškinamasis žodynas

  • anthraquinone — noun Etymology: probably from French, from anthracene + quinone Date: 1869 a yellow crystalline ketone C14H8O2 often derived from anthracene and used especially in the manufacture of dyes …   New Collegiate Dictionary

  • anthraquinone — noun a) A tricyclic quinone, derived from anthracene. b) Any derivative of this parent compound, mostly natural pigments or synthetic dyes …   Wiktionary

  • anthraquinone — an·thra·qui·none .an(t) thrə kwin ōn, kwin .ōn n a yellow crystalline ketone C14H8O2 often derived from anthracene and used esp. in the manufacture of dyes * * * an·thra·quin·one (an″thrə kwinґōn) 1. the 9, 10 quinone derivative… …   Medical dictionary

  • anthraquinone — n. (Chemistry) yellow crystal like water insoluble chemical used in the manufacture of dyes …   English contemporary dictionary


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