Vanadyl acetylacetonate

Structural formula
General
Surname	Vanadyl acetylacetonate
other names	VO (acac) 2 ; Vanadium (IV) oxyacetylacetonate;
Molecular formula	C 10 H 14 O 5 V
Brief description	blue solid
External identifiers / databases
EC number	221-590-8
ECHA InfoCard	100.019.628
PubChem	11821519
Wikidata	Q4353429
properties
Molar mass	265.16 g mol −1
Physical state	firmly
density	1.4 g cm −3
Melting point	235 ° C (decomposition)
boiling point	140 ° C (13 mmHg)
solubility	practically insoluble in water; soluble in ethanol, methanol, benzene and chloroform;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vanadyl acetylacetonate is a chemical compound from the group of acetylacetonates .

Extraction and presentation

Vanadyl acetylacetonate can be obtained by reacting vanadium (V) oxide by prior reduction to oxyvanadium (IV) ions.

{\ displaystyle {\ ce {V2O5 + 2 H2SO4 + C2H5OH -> 2 VOSO4 + 3 H2O + CH3CHO}}}

{\ displaystyle {\ ce {VOSO4 + 2 C5H8O2 + Na2CO3 -> VO (C5H7O2) 2 + Na2SO4 + H2O + CO2}}}

Alternatively, the compound can be obtained by refluxing vanadium (V) oxide in a significant excess of acetylacetone for 24 hours:

{\ displaystyle {\ ce {2 V2O5 + 9C5H8O2 -> [AcAc] [] 4VO (C5H7O2) 2 + (CH3CO) 2CO + 5 H2O}}}

The compound can be purified by recrystallization . Acetone , acetylacetone or dichloromethane are suitable for this .

properties

Vanadyl acetylacetonate

Vanadyl acetylacetonate is a blue solid that is practically insoluble in water.

use

Vanadyl acetylacetonate is used as a catalyst , as a synthesis intermediate, as a paint dryer and as a pigment . It is used in organic chemistry as a reagent in the epoxidation of allyl alcohols in combination with tert-butyl hydroperoxide (TBHP).

Individual evidence

↑ ^a ^b W.LF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 1156 ( limited preview in Google Book search).
↑ ^a ^b ^c Data sheet Vanadium (IV) oxide bis (2,4-pentanedionate) from AlfaAesar, accessed on January 4, 2018 ( PDF )(JavaScript required) .
↑ ^a ^b ^c data sheet Vanadyl acetylacetonate, 99.98% trace metals basis from Sigma-Aldrich , accessed on January 4, 2018 ( PDF ).
^ ^A ^b William M. Haynes: CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 430 ( limited preview in Google Book search).
↑ Vanadium (IV) Oxy (acetylacetonate), Therald Moeller, Burl E. Bryant1, W. Conard Fernelius, Daryle H. Busch, R. Carl Stoufer and Wilmer Stratton, January 5, 2007, doi: 10.1002 / 9780470132364.ch30 .
↑ J. Derek Woollins: Inorganic Experiments . John Wiley & Sons, 2010, ISBN 978-3-527-32472-9 , pp. 142 ( limited preview in Google Book search).
↑ ^a ^b ^c Richard A. Rowe and Mark M. Jones: Vanadium (IV) oxy (acetylacetonate) [bis (2,4-pentanediono) oxovanadium (IV)] . In: Therald Moeller (Ed.): Inorganic Syntheses . tape 5 . McGraw-Hill, Inc., 1957, pp. 113-116 (English).
^ Stock, Norbert .: Synthetic Inorganic Chemistry: Basic Course. De Gruyter, Berlin 2013, ISBN 978-3-11-025875-2 .
^ Arno Behr, Peter Neubert: Applied Homogeneous Catalysis . John Wiley & Sons, 2012, ISBN 978-3-527-32641-9 , pp. 65 ( limited preview in Google Book search).
↑ Alida H Éll, Sandra Y Jonsson, Anna Börje, Hans Adolfsson, Jan-E Bäckvall: Vanadyl acetylacetonate as peroxide activator in osmium-catalyzed dihydroxylation of olefins by hydrogen peroxide. In: Tetrahedron Letters. 42, 2001, pp. 2569-2571, doi: 10.1016 / S0040-4039 (01) 00192-7 .
↑ Peter J. Harrington: Pharmaceutical Process Chemistry for Synthesis Rethinking the Routes to Scale-Up . John Wiley & Sons, 2011, ISBN 0-470-92286-9 , pp. 233 ( limited preview in Google Book search).

[W.L.F._Armarego-1] W.LF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 1156 ( limited preview in Google Book search).

[Alfa-2] Data sheet Vanadium (IV) oxide bis (2,4-pentanedionate) from AlfaAesar, accessed on January 4, 2018 ( PDF )(JavaScript required) .

[Sigma-3] ta sheet Vanadyl acetylacetonate, 99.98% trace metals basis from Sigma-Aldrich , accessed on January 4, 2018 ( PDF ).

[William_M._Haynes-4] A ^b William M. Haynes: CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 430 ( limited preview in Google Book search).

[5] Vanadium (IV) Oxy (acetylacetonate), Therald Moeller, Burl E. Bryant1, W. Conard Fernelius, Daryle H. Busch, R. Carl Stoufer and Wilmer Stratton, January 5, 2007, doi: 10.1002 / 9780470132364.ch30 .

[J._Derek_Woollins-6] J. Derek Woollins: Inorganic Experiments . John Wiley & Sons, 2010, ISBN 978-3-527-32472-9 , pp. 142 ( limited preview in Google Book search).

[IS5-7] Richard A. Rowe and Mark M. Jones: Vanadium (IV) oxy (acetylacetonate) [bis (2,4-pentanediono) oxovanadium (IV)] . In: Therald Moeller (Ed.): Inorganic Syntheses . tape 5 . McGraw-Hill, Inc., 1957, pp. 113-116 (English).

[8] Stock, Norbert .: Synthetic Inorganic Chemistry: Basic Course. De Gruyter, Berlin 2013, ISBN 978-3-11-025875-2 .

[Arno_Behr,_Peter_Neubert-9] Arno Behr, Peter Neubert: Applied Homogeneous Catalysis . John Wiley & Sons, 2012, ISBN 978-3-527-32641-9 , pp. 65 ( limited preview in Google Book search).

[DOI10.1016/S0040-4039(01)00192-7-10] Alida H Éll, Sandra Y Jonsson, Anna Börje, Hans Adolfsson, Jan-E Bäckvall: Vanadyl acetylacetonate as peroxide activator in osmium-catalyzed dihydroxylation of olefins by hydrogen peroxide. In: Tetrahedron Letters. 42, 2001, pp. 2569-2571, doi: 10.1016 / S0040-4039 (01) 00192-7 .

[Peter_J._Harrington-11] Peter J. Harrington: Pharmaceutical Process Chemistry for Synthesis Rethinking the Routes to Scale-Up . John Wiley & Sons, 2011, ISBN 0-470-92286-9 , pp. 233 ( limited preview in Google Book search).