File:Anthraquinone_acsv.svg · Wikimedia Commons · See Wikimedia Commons
anthraquinone
Sign in to saveAlso known as 9,10-quinone, anthradione, Az-Q, 9,10-anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . 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 com
Chemical data
- Formula
- C14H8O2
- Molecular weight
- 208.21 g/mol
- IUPAC name
- anthracene-9,10-dione
- SMILES
- C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3C2=O
- InChIKey
- RZVHIXYEVGDQDX-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 208.052
- Image
- Anthraquinone sample crop.jpg
Show 5 more facts
- melting point
- 286
- chemical formula
- C₁₄H₈O₂
- boiling point
- 379.8
- Commons category
- Anthraquinone
- canonical SMILES
- C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3C2=O
via Wikidata · CC0
~3 min read
Article
8 sectionsContents
- Synthesis
- Reactions
- Applications
- Other isomers
- Safety
- See also
- References
- External links
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . 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. This process was pioneered by BASF.