Anthraquinone

9,10-Anthraquinone^[1]
Names
	Preferred IUPAC name Anthracene-9,10-dione
	Other names Anthraquinone; 9,10-Anthracenedione; Anthradione; 9,10-Anthrachinon; Anthracene-9,10-quinone; 9,10-Dihydro-9,10-dioxoanthracene; Hoelite; Morkit; Corbit;
Identifiers
CAS Number	84-65-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	390030
ChEBI	CHEBI:40448 ;
ChEMBL	ChEMBL55659 ;
ChemSpider	6522 ;
ECHA InfoCard	100.001.408
EC Number	201-549-0;
Gmelin Reference	102870
KEGG	C16207 ;
PubChem CID	6780;
RTECS number	CB4725000;
UNII	030MS0JBDO;
UN number	3143
CompTox Dashboard (EPA)	DTXSID3020095 ;
	InChI InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H Key: RZVHIXYEVGDQDX-UHFFFAOYSA-N;
	SMILES O=C1c2ccccc2C(=O)c3ccccc13;
Properties
Chemical formula	C14H8O2
Molar mass	208.216 g·mol−1
Appearance	Yellow solid
Density	1.438 g/cm3
Melting point	284.8 °C (544.6 °F; 558.0 K)
Boiling point	377 °C (711 °F; 650 K)
Solubility in water	Insoluble
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	possible carcinogen
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H350
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
Flash point	185 °C (365 °F; 458 K)
Related compounds
Related compounds	quinone,; anthracene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
₁₄H
₈O
₂. Several isomers exist but these terms usually refer to 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring. It is used as a digester additive to wood pulp for papermaking. Many anthraquinone derivatives are generated by organisms or synthesised industrially for use as dyes, pharmaceuticals, and catalysts. Anthraquinone is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.

Synthesis

There are several current industrial methods to produce 9,10-anthraquinone:

The oxidation of anthracene. Chromium(VI) is the typical oxidant.
The Friedel–Crafts reaction of benzene and phthalic anhydride in presence of AlCl₃. o-Benzoylbenzoic acid is an intermediate. This reaction is useful for producing substituted anthraquinones.
The Diels-Alder reaction of naphthoquinone and butadiene followed by oxidative dehydrogenation.
The acid-catalyzed dimerization of styrene to give a 1,3-diphenylbutene, which then can be transformed to the anthraquinone.^[3] This process was pioneered by BASF.

It also arises via the Rickert–Alder reaction, a retro-Diels–Alder reaction.

Reactions

Hydrogenation gives dihydroanthraquinone (anthrahydroquinone). Reduction with copper gives anthrone.^[4] Sulfonation with oleum gives anthroquinone-1-sulfonic acid,^[5] which reacts with sodium chlorate to give 1-chloroanthraquinone.^[6]

Applications

Anthraquinone itself has few direct applications except as a precursor to some dyes. It has been used as a bird repellant on seeds, and as a gas generator in satellite balloons.^[7] It has also been mixed with lanolin and used as a wool spray to protect sheep flocks against kea attacks in New Zealand.^[8] Anthraquinone is utilized in the production of hydrogen peroxide via the Riedl–Pfleiderer process.^[9] Anthraquinone derivatives are considered more useful.

Other isomers

Several other isomers of anthraquinone exist, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of minor importance compared to 9,10-anthraquinone.

Safety

Anthraquinone has no recorded LD₅₀, probably because it is so insoluble in water.

In terms of metabolism of substituted anthraquinones, the enzyme encoded by the gene UGT1A8 has glucuronidase activity with many substrates including anthraquinones.^[10]

References

1 2 3 4 Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.28. ISBN 9781498754293.
↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 724. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
↑ Vogel, A. "Anthraquinone". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_347. ISBN 978-3-527-30673-2.
↑ Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4. doi:10.15227/orgsyn.014.0004.
↑ Scott, W. J.; Allen, C. F. H. (1938). "Potassium Anthraquinone-α-Sulfonate". Organic Syntheses. 18: 72. doi:10.15227/orgsyn.018.0072.
↑ Scott, W. J.; Allen, C. F. H. (1938). "α-Chloroanthraquinone". Organic Syntheses. 18: 15. doi:10.15227/orgsyn.018.0015.
↑ "www.americanheritage.com". Archived from the original on 2009-06-09. Retrieved 2009-09-22.
↑ Dudding, Adam (29 July 2012). "How to solve a problem like a kea". Sunday Star Times. New Zealand. Retrieved 11 November 2014.
↑ Campos-Martin, Jose M.; Blanco-Brieva, Gema; Fierro, Jose L. G. (2006). "Hydrogen Peroxide Synthesis: An Outlook beyond the Anthraquinone Process". Angewandte Chemie International Edition. 45 (42): 6962–6984. doi:10.1002/anie.200503779. PMID 17039551.
↑ Ritter, J. K.; Chen, F.; Sheen, Y. Y.; Tran, H. M.; Kimura, S.; Yeatman, M. T.; Owens, I. S. (1992). "A Novel Complex Locus UGT1 Encodes Human Bilirubin, Phenol, and other UDP-Glucuronosyltransferase Isozymes with Identical Carboxyl Termini" (PDF). Journal of Biological Chemistry. 267 (5): 3257–3261. doi:10.1016/S0021-9258(19)50724-4. PMID 1339448.

External links

[crc-1] 1 2 3 4 Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.28. ISBN 9781498754293.

[2] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 724. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[Ullmann-3] Vogel, A. "Anthraquinone". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_347. ISBN 978-3-527-30673-2.

[4] Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4. doi:10.15227/orgsyn.014.0004.

[5] Scott, W. J.; Allen, C. F. H. (1938). "Potassium Anthraquinone-α-Sulfonate". Organic Syntheses. 18: 72. doi:10.15227/orgsyn.018.0072.

[6] Scott, W. J.; Allen, C. F. H. (1938). "α-Chloroanthraquinone". Organic Syntheses. 18: 15. doi:10.15227/orgsyn.018.0015.

[7] "www.americanheritage.com". Archived from the original on 2009-06-09. Retrieved 2009-09-22.

[8] Dudding, Adam (29 July 2012). "How to solve a problem like a kea". Sunday Star Times. New Zealand. Retrieved 11 November 2014.

[9] Campos-Martin, Jose M.; Blanco-Brieva, Gema; Fierro, Jose L. G. (2006). "Hydrogen Peroxide Synthesis: An Outlook beyond the Anthraquinone Process". Angewandte Chemie International Edition. 45 (42): 6962–6984. doi:10.1002/anie.200503779. PMID 17039551.

[pmid1339448-10] Ritter, J. K.; Chen, F.; Sheen, Y. Y.; Tran, H. M.; Kimura, S.; Yeatman, M. T.; Owens, I. S. (1992). "A Novel Complex Locus UGT1 Encodes Human Bilirubin, Phenol, and other UDP-Glucuronosyltransferase Isozymes with Identical Carboxyl Termini" (PDF). Journal of Biological Chemistry. 267 (5): 3257–3261. doi:10.1016/S0021-9258(19)50724-4. PMID 1339448.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]