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Title: 2-ethylanthraquinone  
Author: World Heritage Encyclopedia
Language: English
Subject: Hydrogen peroxide
Publisher: World Heritage Encyclopedia


CAS number 84-51-5 YesY
ChemSpider 6514 YesY
EC number 201-535-4
Jmol-3D images Image 1
Molecular formula C16H12O2
Molar mass 236.27 g/mol
Appearance white to yellowish crystals or powder
Density 1.231g/cm3
Melting point

105 °C, 378 K, 221 °F

Boiling point

415.4 @ 760mmHg

S-phrases S24 S25
Flash point 155.4 °C,
 YesY (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

2-Ethylanthraquinone also called2-Ethyl-9,10-anthraquinone is an aromatic organic compound with the formula C16H12O2. The slightly yellow powder is used in the production of hydrogen peroxide (H2O2).


2-Ethylanthraquinone is prepared from the reaction of phthalic anhydride and ethylbenzene: C6H4(CO)2O + C6H5CH2CH3 → C6H4C2O2C6H3C2H5 + H2O. Both phthalic anhydride and ethylbenzene are readily available but are mainly used in the large-scale production of plastics.


Hydrogen peroxide is produced industrially by the anthraquinone process which involves using 2-alkyl-9,10-anthraquinones for hydrogenation. Many derivatives of anthraquinone are used but 2-Ethylanthraquinone is common because of its high selectivity. The hydrogenation of the unsubsituted ring can reach 90% selectivity by using 2-ethylanthraquinone. Hydrogenation follows the Riedl-Pfleiderer, or autoxidation, process:

The hydrogenation of 2-ethylanthrahydroquinone is catalyzed by palladium metal. During hydrogenation both 2-ethylanthrahydroquinone and tetrahydroanthraquinone are produced. The tetrahydro derivative of 2-alkylanthraquinone is easily hyrdrogenated but is more difficult to oxidize. This has led to a split in production methods, with current research focusing on the effectiveness of the tetrahydro system. The formation of the tetrahyrdo derivative can be suppressed through use of special catalysts, solvents, and conditions. A working solution must be able to keep the 2-ethylanthraquinone dissolved in the hyrdrogenation, oxidation, and extraction steps. Since hydroquinones dissolve better in polar solvents, and quinones dissolve better in aromatic nonpolar solvents, a solvent mixture must be used. Some suggested mixtures are polyalkylated benzenes and alkyl phosphates or tetraalkyl ureas, trimethylbenzenes and alkylcyclohexanol esters, and methylnaphthalene and nonyl alcohols.


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