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{{Short description|Intermediate Chemical in H2O2 Synthesis}}
{{chembox
{{Chembox
| Watchedfields = changed | Verifiedfields = changed
| verifiedrevid = 413109678 | verifiedrevid = 477213314
| Name = 2-Ethylanthraquinone | Name = 2-Ethylanthraquinone
| ImageFile = 2-Ethylanthraquinone.svg | ImageFile = 2-Ethylanthraquinone.svg
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| ImageName1 = Ball-and-stick model | ImageName1 = Ball-and-stick model
| ImageSize1 = 230px | ImageSize1 = 230px
| PIN = 2-Ethylanthracene-9,10-dione
| OtherNames = 2-Ethyl-9,10-anthracenedione | OtherNames = 2-Ethyl-9,10-anthracenedione
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6514 | ChemSpiderID = 6514
| PubChem = 6772
| UNII = 59YJ81QZKD
| 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,2H2,1H3 | 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,2H2,1H3
| InChIKey = SJEBAWHUJDUKQK-UHFFFAOYAW | InChIKey = SJEBAWHUJDUKQK-UHFFFAOYAW
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SJEBAWHUJDUKQK-UHFFFAOYSA-N | StdInChIKey = SJEBAWHUJDUKQK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|changed|??}}
| CASNo = 84-51-5 | CASNo = 84-51-5
| EINECS = 201-535-4 | EINECS = 201-535-4
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}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
⚫ | FlashPtC = 155.4
| SPhrases = {{S24}} {{S25}}
| GHSPictograms = {{GHS08}}{{GHS09}}
⚫ | FlashPtC = 155.4
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|350|373|410}}
| PPhrases = {{P-phrases|201|202|260|273|281|308+313|314|391|405|501}}
}} }}
}} }}


'''2-Ethylanthraquinone''' also called'''2-Ethyl-9,10-anthraquinone''' is an ] ] with the ] C<sub>16</sub>H<sub>12</sub>O<sub>2</sub>. The slightly yellow powder is used in the production of ] (H<sub>2</sub>O<sub>2</sub>). '''2-Ethylanthraquinone''' is an ] that is a derivative of ]. This pale yellow solid is used in the industrial production of ] (H<sub>2</sub>O<sub>2</sub>).<ref>{{cite encyclopedia |author1=Goor, G. |author2=Glenneberg, J. |author3=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 |isbn=9783527303854 }}</ref><ref>Römpp CD 2006, Georg Thieme Verlag 2006</ref>


==Production== ==Production==
2-Ethylanthraquinone is prepared from the reaction of ] and ]: C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CH<sub>3</sub> → C<sub>6</sub>H<sub>4</sub>C<sub>2</sub>O<sub>2</sub>C<sub>6</sub>H<sub>3</sub>C<sub>2</sub>H<sub>5</sub> + H<sub>2</sub>O. Both phthalic anhydride and ethylbenzene are readily available but are mainly used in the large-scale production of plastics. 2-Ethylanthraquinone is prepared from the reaction of ] and ]:
:C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + C<sub>6</sub>H<sub>5</sub>Et → C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>Et + H<sub>2</sub>O.
Both phthalic anhydride and ethylbenzene are readily available, being otherwise used in the large-scale production of plastics.


==Uses== ==Uses==
] is produced industrially by the ] 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 ], process: ] is produced industrially by the ] 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 unsubstituted ring can reach 90% selectivity by using 2-ethylanthraquinone. Hydrogenation follows the Riedl-Pfleiderer, or ], process:


]<br style="clear:left;"/> ]{{clear|left}}
The hydrogenation of ] is catalyzed by ] metal. During hydrogenation both ] and ] 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. The ] of ] is catalyzed by ]. Hydrogenation produces both 2-ethylanthrahydroquinone and tetrahydroanthraquinone. The tetrahydro derivative of 2-alkylanthraquinone is easily hydrogenated but is more difficult to oxidize. The formation of the tetrahydro derivative can be suppressed through the selection 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.
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.


==References== ==References==
<references />


{{DEFAULTSORT:Ethylanthraquinone, 2-}} {{DEFAULTSORT:Ethylanthraquinone, 2-}}

Latest revision as of 10:04, 13 January 2024

Intermediate Chemical in H2O2 Synthesis
2-Ethylanthraquinone
Structural formula of 2-Ethylanthraquinone
Ball-and-stick model
Names
Preferred IUPAC name 2-Ethylanthracene-9,10-dione
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
PubChem CID
UNII
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
GHS labelling:
Pictograms GHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H350, H373, H410
Precautionary statements P201, P202, P260, P273, P281, P308+P313, P314, P391, P405, P501
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). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Ethylanthraquinone is an organic compound that is a derivative of anthraquinone. This 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 + C6H5Et → C6H4(CO)2C6H3Et + 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 unsubstituted 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 hydrogenated but is more difficult to oxidize. The formation of the tetrahydro derivative can be suppressed through the selection 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. Goor, G.; Glenneberg, J.; Jacobi, S. (2007). "Hydrogen Peroxide". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_443.pub2. ISBN 9783527303854.
  2. Römpp CD 2006, Georg Thieme Verlag 2006
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