Misplaced Pages

2-Ethylanthraquinone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Smokefoot (talk | contribs) at 19:36, 19 January 2014 (ref and deconstruct awkwardly written student work, still highly imperfect). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 19:36, 19 January 2014 by Smokefoot (talk | contribs) (ref and deconstruct awkwardly written student work, still highly imperfect)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
2-Ethylanthraquinone
Structural formula of 2-Ethylanthraquinone
Ball-and-stick model
Names
Other names 2-Ethyl-9,10-anthracenedione
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.396 Edit this at Wikidata
EC Number
  • 201-535-4
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H12O2/c1-2-10-7-8-13-14(9-10)16(18)12-6-4-3-5-11(12)15(13)17/h3-9H,2H2,1H3Key: SJEBAWHUJDUKQK-UHFFFAOYSA-N
  • InChI=1/C16H12O2/c1-2-10-7-8-13-14(9-10)16(18)12-6-4-3-5-11(12)15(13)17/h3-9H,2H2,1H3Key: SJEBAWHUJDUKQK-UHFFFAOYAW
SMILES
  • O=C2c1c(cccc1)C(=O)c3c2ccc(c3)CC
Properties
Chemical formula C16H12O2
Molar mass 236.27 g/mol
Appearance white to yellowish crystals or powder
Density 1.231g/cm3
Melting point 105 °C (221 °F; 378 K)
Boiling point 415.4 @ 760mmHg
Hazards
Flash point 155.4 °C (311.7 °F; 428.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

2-Ethylanthraquinone is an organic compound that is a derivtive of anthraquinone. It is pale yellow solid is used in the industrial production of hydrogen peroxide (H2O2).

Production

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, being otherwise used in the large-scale production of plastics.

Uses

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 Riedl-Pfleiderer process.
The Riedl-Pfleiderer process.


The hydrogenation of 2-ethylanthraquinone is catalyzed by palladium. Hydrogenation produces both 2-ethylanthrahydroquinone and tetrahydroanthraquinone. The tetrahydro derivative of 2-alkylanthraquinone is easily hyrdrogenated but is more difficult to oxidize. The formation of the tetrahyrdo derivative can be suppressed through the seelection of catalysts, solvents, and reaction conditions. Some suggested solvent mixtures are polyalkylated benzenes and alkyl phosphates or tetraalkyl ureas, trimethylbenzenes and alkylcyclohexanol esters, and methylnaphthalene and nonyl alcohols.

References

  1. cite encyclopedia | author = Goor, G.; Glenneberg, J.; Jacobi, S. | title = Hydrogen Peroxide | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | year = 2007 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a13_443.pub2 }}
  2. Römpp CD 2006, Georg Thieme Verlag 2006
Category: