2-decanone

Structural formula
General
Surname	2-decanone
other names	Methyl octyl ketone; Decane-2-one;
Molecular formula	C 10 H 20 O
Brief description	colorless liquid
External identifiers / databases
EC number	211-752-6
ECHA InfoCard	100.010.685
PubChem	12741
Wikidata	Q20054515
properties
Molar mass	156.27 g mol −1
Physical state	liquid
density	0.82 g cm −3
Melting point	3 ° C
boiling point	211 ° C
Vapor pressure	2 mbar (50 ° C)
solubility	practically insoluble in water; soluble in ethanol;
Refractive index	1.425 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-decanone is a chemical compound from the group of dialkyl ketones .

Occurrence

2-decanone occurs in relatively high concentrations in the resin of the East African tree Commiphora rostrata . It also occurs in rue .

Extraction and presentation

2-Decanone can be obtained by oxy-galling 1-decene with thallium (III) nitrate in methanol at 0 ° C. 1-Decene can also be converted to 2-decanone with oxygen and palladium complex catalysts by means of Wacker-Tsuji oxidation .

It can also by hydration of 2-Decin be obtained, whereby 3-decanone arises.

properties

2-decanone is a hardly flammable colorless liquid that is practically insoluble in water.

use

2-decanone is used as a fragrance.

safety instructions

The vapors of 2-decanone can form an explosive mixture with air ( flash point > 75 ° C, ignition temperature 215 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry for CAS no. 693-54-9 in the GESTIS substance database of the IFA , accessed on May 4, 2015(JavaScript required) .
↑ William M. Haynes: CRC Handbook of Chemistry and Physics, 95th Edition: . CRC Press, 2014, ISBN 978-1-4822-0868-9 , pp. 62 ( limited preview in Google Book search).
↑ Data sheet 2-Decanone, ≥98% from Sigma-Aldrich , accessed on May 4, 2015 ( PDF ).
↑ R. Hegnauer: Chemotaxonomy of plants: An overview of the distribution and the systematic importance of plant substances . Springer-Verlag, 2013, ISBN 978-3-0348-9283-4 , pp. 703 ( limited preview in Google Book search).
↑ Frank D. Gunstone, John L. Harwood, Fred B Padley: The Lipid Handbook, Second Edition: . CRC Press, 1994, ISBN 978-0-412-43320-7 , pp. 45 ( limited preview in Google Book search).
↑ Jutta Backes, Gerhard Becker, Peter Behnisch, Karl-Heinz Büchel, Jürgen Falbe, Herrmann Hagemann, Michael Hanack, Dieter Klamann, Richard P. Kreher, Christine Kropf, Dieter Lenoir, Thomas Lippert, Manfred Regitz , Ernst Schmitz : Houben-Weyl , Volume E 16c, 4th Edition Supplement: Organic N Compounds III: Nitrous / Nitric Acid Esters, Nitrenes, 3- and 4-Membered . Georg Thieme Verlag, 2014, ISBN 3-13-181924-3 , p. 45 ( limited preview in Google Book search).
↑ Ei-ichi Negishi: Handbook of Organopalladium Chemistry for Organic Synthesis, 2 Volume Set . John Wiley & Sons, 2003, ISBN 0-471-47381-2 , pp. 2156 ( limited preview in Google Book search).
↑ Jiro Tsuji, Hideo Nagashima, Hisao Nemoto: A General Synthetic Method for the Preparation of Methyl Ketones from Terminal Olefins: 2-Decanone. In: Organic Syntheses. 62, 1984, p. 9, doi : 10.15227 / orgsyn.062.0009 .
↑ Robert J. Ouellette, J. David Rawn: Principles of Organic Chemistry: . Academic Press, 2015, ISBN 0-12-802634-0 , pp. 116 ( limited preview in Google Book search).
↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition: . CRC Press, 2009, ISBN 978-1-4200-9086-4 , pp. 2069 ( limited preview in Google Book Search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry for CAS no. 693-54-9 in the GESTIS substance database of the IFA , accessed on May 4, 2015(JavaScript required) .

[William_M._Haynes-2] William M. Haynes: CRC Handbook of Chemistry and Physics, 95th Edition: . CRC Press, 2014, ISBN 978-1-4822-0868-9 , pp. 62 ( limited preview in Google Book search).

[Sigma-3] Data sheet 2-Decanone, ≥98% from Sigma-Aldrich , accessed on May 4, 2015 ( PDF ).

[R._Hegnauer-4] R. Hegnauer: Chemotaxonomy of plants: An overview of the distribution and the systematic importance of plant substances . Springer-Verlag, 2013, ISBN 978-3-0348-9283-4 , pp. 703 ( limited preview in Google Book search).

[Frank_D._Gunstone,_John_L._Harwood,_Fred_B._Padley-5] Frank D. Gunstone, John L. Harwood, Fred B Padley: The Lipid Handbook, Second Edition: . CRC Press, 1994, ISBN 978-0-412-43320-7 , pp. 45 ( limited preview in Google Book search).

[Jutta_Backes,_Gerhard_Becker,_Peter_Behnisch,_Karl-Heinz_Büchel,_Jürgen_Falbe,_Herrmann_Hagemann,_Michael_Hanack,_Dieter_Klamann,_Richard_P._Kreher,_Christine_Kropf,_Dieter_Lenoir,_Thomas_Lippert,_Manfred_Regitz,_Ernst_Schmitz-6] Jutta Backes, Gerhard Becker, Peter Behnisch, Karl-Heinz Büchel, Jürgen Falbe, Herrmann Hagemann, Michael Hanack, Dieter Klamann, Richard P. Kreher, Christine Kropf, Dieter Lenoir, Thomas Lippert, Manfred Regitz , Ernst Schmitz : Houben-Weyl , Volume E 16c, 4th Edition Supplement: Organic N Compounds III: Nitrous / Nitric Acid Esters, Nitrenes, 3- and 4-Membered . Georg Thieme Verlag, 2014, ISBN 3-13-181924-3 , p. 45 ( limited preview in Google Book search).

[Ei-ichi_Negishi-7] Ei-ichi Negishi: Handbook of Organopalladium Chemistry for Organic Synthesis, 2 Volume Set . John Wiley & Sons, 2003, ISBN 0-471-47381-2 , pp. 2156 ( limited preview in Google Book search).

[tsuji-8] Jiro Tsuji, Hideo Nagashima, Hisao Nemoto: A General Synthetic Method for the Preparation of Methyl Ketones from Terminal Olefins: 2-Decanone. In: Organic Syntheses. 62, 1984, p. 9, doi : 10.15227 / orgsyn.062.0009 .

[Robert_J._Ouellette,_J._David_Rawn-9] Robert J. Ouellette, J. David Rawn: Principles of Organic Chemistry: . Academic Press, 2015, ISBN 0-12-802634-0 , pp. 116 ( limited preview in Google Book search).

[George_A._Burdock-10] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition: . CRC Press, 2009, ISBN 978-1-4200-9086-4 , pp. 2069 ( limited preview in Google Book Search).