Anthraquinone

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9,10-Anthraquinone[1]
Names
Preferred IUPAC name
Anthracene-9,10-dione[2]
Other names
  • Anthraquinone
  • 9,10-Anthracenedione
  • Anthradione
  • 9,10-Anthrachinon
  • Anthracene-9,10-quinone
  • 9,10-Dihydro-9,10-dioxoanthracene
  • Hoelite
  • Morkit
  • Corbit
Identifiers
3D model (
JSmol
)
390030
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.001.408 Edit this at Wikidata
102870
KEGG
RTECS number
  • CB4725000
UNII
UN number 3143
  • 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
  • O=C1c2ccccc2C(=O)c3ccccc13
Properties
C14H8O2
Molar mass 208.216 g·mol−1
Appearance Yellow solid
Density 1.438 g/cm3[1]
Melting point 284.8 °C (544.6 °F; 558.0 K)[1]
Boiling point 377 °C (711 °F; 650 K)[1]
Insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 possible carcinogen
GHS labelling:
GHS08: Health hazard
Danger
H350
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).
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Anthraquinone, also called anthracenedione or dioxoanthracene, is an

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. 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:

  1. The oxidation of
    Chromium(VI)
    is the typical oxidant.
  2. The
    AlCl3
    . o-Benzoylbenzoic acid is an intermediate. This reaction is useful for producing substituted anthraquinones.
  3. The
    Diels-Alder reaction of naphthoquinone and butadiene
    followed by oxidative dehydrogenation.
  4. 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 sulfuric acid gives anthroquinone-1-sulfonic acid,[5] which reacts with sodium chlorate to give 1-chloroanthaquinone.[6]

Applications

See also: anthraquinones

Digester additive in papermaking

9,10-Anthraquinone is used as a digester additive in production of

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 anthraquinone is regenerated. This process gives an increase in yield of pulp, typically 1–3% and a reduction in kappa number.[8]

Use in flow batteries

9,10-Anthraquinone is used as an electrolyte in flow battery which can provide long term electrical storage.

Niche uses

9,10-anthraquinone is used as a bird repellant on seeds, and as a gas generator in satellite balloons.[9] It has also been mixed with lanolin and used as a wool spray to protect sheep flocks against kea attacks in New Zealand.[10]

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.

Recently, a class of anthraquinone derivates were shown to have self-healing properties when doped in PMMA matrix.[11]

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.[12]

See also

References

  1. ^
    ISBN 9781498754293
    .
  2. ISBN 978-0-85404-182-4
    .
  3. ISBN 978-3527306732
    .
  4. doi:10.15227/orgsyn.014.0004
    .
  5. doi:10.15227/orgsyn.018.0072
    .
  6. doi:10.15227/orgsyn.018.0015
    .
  7. hdl:1853/24767
    .
  8. ISBN 0-89852-340-0
    .
  9. ^ "www.americanheritage.com". Archived from the original on 2009-06-09. Retrieved 2009-09-22.
  10. ^ Dudding, Adam (29 July 2012). "How to solve a problem like a kea". Sunday Star Times. New Zealand. Retrieved 11 November 2014.
  11. S2CID 5512565
    .
  12. PMID 1339448
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Anthraquinone&oldid=1208957098"