2-Ethylanthraquinone: Difference between revisions

2-Ethylanthraquinone
Names
	Preferred IUPAC name 2-Ethylanthracene-9,10-dione
	Other names 2-Ethyl-9,10-anthracenedione
Identifiers
CAS Number	84-51-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL42355 ;
ChemSpider	6514 ;
ECHA InfoCard	100.001.396
EC Number	201-535-4;
PubChem CID	6772;
UNII	59YJ81QZKD;
CompTox Dashboard (EPA)	DTXSID5044994 ;
	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,2H2,1H3 Key: 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,2H2,1H3 Key: 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
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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Latest revision as of 10:04, 13 January 2024

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).^[1]^[2]

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 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

^ 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.
^ Römpp CD 2006, Georg Thieme Verlag 2006

[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

[1]

[2]

@@ Line 1: / Line 1: @@
+{{Short description|Intermediate Chemical in H2O2 Synthesis}}
-{{chembox
+{{Chembox
-| Watchedfields = changed
+| Verifiedfields = changed
-| verifiedrevid = 413109678
+| verifiedrevid = 477213314
 |   Name = 2-Ethylanthraquinone
 |   ImageFile = 2-Ethylanthraquinone.svg
@@ Line 9: / Line 10: @@
 |   ImageName1 = Ball-and-stick model
 |   ImageSize1 = 230px
+|   PIN = 2-Ethylanthracene-9,10-dione
 |   OtherNames = 2-Ethyl-9,10-anthracenedione
 | Section1 = {{Chembox Identifiers
 |   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | 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
 | InChIKey = SJEBAWHUJDUKQK-UHFFFAOYAW
@@ Line 22: / Line 26: @@
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = SJEBAWHUJDUKQK-UHFFFAOYSA-N
+| CASNo_Ref = {{cascite|changed|??}}
 | CASNo = 84-51-5
 |   EINECS = 201-535-4
@@ Line 34: / Line 39: @@
   }}
 | Section7 = {{Chembox Hazards
+| FlashPtC = 155.4
-|   SPhrases = {{S24}} {{S25}}
+| GHSPictograms = {{GHS08}}{{GHS09}}
-|  FlashPt = 155.4&nbsp;°C,
+| 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 [[aromatic]] [[organic compound]] with the [[formula]] C<sub>16</sub>H<sub>12</sub>O<sub>2</sub>. The slightly yellow powder is used in the production of [[hydrogen peroxide]] (H<sub>2</sub>O<sub>2</sub>).
+'''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]] (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==
--Ethylanthraquinone is prepared from the reaction of [[phthalic anhydride]] and [[ethylbenzene]]: 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.
+-Ethylanthraquinone is prepared from the reaction of [[phthalic anhydride]] and [[ethylbenzene]]:
+: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==
-[[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:
+[[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:
-[[Image:Riedl-Pfleiderer process.svg|left|400px|The Riedl-Pfleiderer process.]]<br style="clear:left;"/>
+[[File:Riedl-Pfleiderer process.svg|left|400px|The Riedl-Pfleiderer process.]]{{clear|left}}
-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.
+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.
-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 />
 {{DEFAULTSORT:Ethylanthraquinone, 2-}}