Anthraquinone: Difference between revisions

| verifiedrevid = 322333943

| Name = 9,10-Anthraquinone

| ImageFile = Anthraquinone acsv.svg

| ImageSize = 190px

| ImageName = Skeletal formula

| ImageFile1 = Anthraquinone-3D-balls.png

| ImageSize1 = 210px

| ImageName1 = Ball-and-stick model

| IUPACName = Anthraquinone

| OtherNames = 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit

| ChemSpiderID = 6522

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = <!-- blanked - oldvalue: 55659 -->

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 84-65-1

| RTECS =

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C16207

|C=14|H=8|O=2

| Appearance = yellow solid

| Density = 1.308g/cm3

| MeltingPt = 286 °C

| BoilingPt = 379.8 °C

| MainHazards =

| FlashPt = 185°C

| RPhrases = {{R36/37/38}}

| SPhrases =

| OtherCpds = [[quinone]],</br> [[anthracene]]

'''Anthraquinone''', also called '''anthracenedione''' or '''dioxoanthracene''' is an [[aromatic hydrocarbon|aromatic]] [[organic compound]] with formula {{chem|C|14|H|8|O|2}}. 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 [[ketone|keto]] groups are located on the central ring. It is a building block of many [[dye]]s and is used in bleaching pulp for papermaking. It is a yellow highly crystalline solid, poorly [[solubility|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.

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.<ref name=Ullmann>Axel Vogel "Anthraquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a02_347}}</ref> 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 [[condensation reaction|condenses]] with [[glycerol]] forming [[benzanthrone]].<ref>{{OrgSynth | title = Benzathrone | author = Macleod L.C., Allen C.F.H. | collvol = 2 | collvolpages = 62 | year = 1943 | prep = CV2P0062}}</ref> In this reaction, the quinone is first [[organic reduction|reduced]] with [[copper]] metal in [[sulfuric acid]] (converting one [[ketone]] group into a [[methylene]] group) after which the glycerol is added.

:[[Image:Bally-SchollSynthesis.png|450px|Bally-Scholl Synthesis]]

==Applications and natural occurrence==

===Dyestuff precursor===

Synthetic dyes are often derived from 9,10-anthraquinone, such as [[alizarin]].<ref name=UllmannDye>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}}</ref> Important derivatives are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the dinitroanthraquinone.<ref name=Ullmann/> Natural [[pigment]]s that are derivatives of anthraquinone are found, inter alia, in aloe latex, [[Senna (herb)|senna]], [[rhubarb]], and [[Rhamnus purshiana|Cascara buckthorn]]), [[fungi]], [[lichen]]s, and some [[insect]]s.

[[Image:AnthDyes.png|thumb|center|750px|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.]]

According to Dr. Bryle Kristopher Cavalencia, 9,10-Anthraquinone is used as a digester additive in production of [[pulp (paper)|paper pulp]] by [[alkaline]] processes, like the [[kraft process|Kraft]], the alkaline [[sulfite process|sulfite]] or the [[soda pulping|Soda-AQ]] processes. The anthraquinone is a [[redox]] [[catalyst]]. The reaction mechanism may involve [[single electron transfer]] (SET).<ref>{{Cite document | first = James Christian | last = Samp | title = A comprehensive mechanism for anthraquinone mass transfer in alkaline pulping | year = 2008 | page = 30 | publisher = Georgia Institute of Technology | url = http://gradworks.umi.com/33/27/3327651.html | postscript = <!-- Bot inserted parameter. Either remove it; or change its value to "." for the cite to end in a ".", as necessary. -->{{inconsistent citations}} }}</ref> 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]].<ref>{{Cite book | editor = Goyal, Gopal C. |last = Sturgeoff | first = L.G. | author-link = | last2 = Pitl | first2 = Y. | author2-link = | title = Low Kappa pulping without capital investment | journal = Antraquinone Pulping. A TAPPI Press anthology of published papers, 1977-1996. | pages = 3–9 | origyear = 1993 | year = 1997 | isbn = 0-89852-340-0 | postscript = <!--None-->}}</ref>

[[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.<ref>{{cite web | url = http://smartech.gatech.edu/bitstream/1853/673/1/3370_001_071978.pdf | title= Anthraquinone/ alkali pulping. A literature review|first= |last= |author= |authorlink= |coauthors= |date=|month=7 |year=1978 |work= |publisher= |location= |page= |pages= |at= |language= |trans_title= |format= |doi= |archiveurl= |archivedate= |accessdate= |quote= |ref= |separator= |postscript= }}</ref>

===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.<ref>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}}.</ref>

:[[Image:Riedl-Pfleiderer process.png|300px|thumb|left|Catalytic hydrogen peroxide production with the anthraquinone process]]{{clear-left}}

===Medicine===

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

* [[Laxative]]s such as [[dantron]], [[emodin]], and [[aloe emodin]], and some of the [[senna glycosides]]

* [[Antimalarial]]s such as [[rufigallol]]

* [[Antineoplastic]]s used in the treatment of [[cancer]], such as [[mitoxantrone]], [[pixantrone]], and the [[anthracycline]]s.

<table border=0 cellborder=0>

<tr valign=center>

<td align=center>[[File:Aloe emodin.svg|150px]]</td>

<td align=center>[[File:Mitoxantrone skeletal.svg|180px]]</td>

<td align=center>[[File:Pixantrone.svg|180px]]</td>

<tr/>

<tr valign=top>

<td align=center>Aloe emodin</td>

<td align=center>Mitoxantrone</td>

<td align=center>Pixantrone</td>

<tr/>

</table>

===Niche uses===

9,10-Anthraquinone is used as a bird repellant on seeds and as a gas generator in satellite balloons [http://www.americanheritage.com/articles/magazine/it/2007/1/2007_1_38.shtml].

Natural anthraquinone derivatives tend to have [[laxative]] effects. Prolonged use and [[substance abuse|abuse]] leads to [[melanosis coli]].<ref>{{cite journal |author=Müller-Lissner SA |title=Adverse effects of laxatives: fact and fiction |journal=Pharmacology |volume=47 |issue=Suppl 1 |pages=138–45 |year=1993 |pmid=8234421 |doi=10.1159/000139853}}</ref><ref name="pmid3280173">{{cite journal |author=Moriarty KJ, Silk DB |title=Laxative abuse |journal=Dig Dis |volume=6 |issue=1 |pages=15–29 |year=1988 |pmid=3280173 |doi=10.1159/000171181 }}</ref> 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. <ref>[http://www.jbc.org/content/280/5/3628.full.pdf+html].</ref>

==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 group]]s. These derivatives include substances that are technically useful or play important roles in living beings.

==See also==

*[[Benzoquinone]]

*[[Naphthoquinone]]

*[[Parietin]]

* [http://www.npi.gov.au/database/substance-info/profiles/74.html National Pollutant Inventory — Polycyclic Aromatic Hydrocarbon Fact Sheet]

* [http://www.sciencedaily.com/releases/2006/08/060818014819.htm Molecules Spontaneously Form Honeycomb Network]

{{Natural phenol}}

{{Anthraquinone}}

[[ar:أنثراكينون]]

[[ca:Antraquinona]]

[[cs:Antrachinon]]

[[de:Anthrachinon]]

[[es:Antraquinona]]

[[fr:Anthraquinone]]

[[ko:안트라퀴논]]

[[it:Antrachinone]]

[[kk:Антрахинон]]

[[hu:Antrakinon]]

[[nl:Anthrachinon]]

[[ja:アントラキノン]]

[[no:Antrakinon]]

[[pl:Antrachinon]]

[[pt:Antraquinona]]

[[ru:Антрахинон]]

[[sk:Antrachinón]]

[[fi:Antrakinoni]]

[[uk:Антрахінон]]

[[zh:蒽醌]]