2-heptanone

Structural formula
General
Surname	2-heptanone
other names	Amyl methyl ketone; Methyl amyl ketone; MAK; Heptan-2-one; Methyl pentyl ketone;
Molecular formula	C 7 H 14 O
Brief description	colorless liquid with a fruity odor
External identifiers / databases
EC number	203-767-1
ECHA InfoCard	100.003.426
PubChem	8051
Wikidata	Q517266
properties
Molar mass	114.19 g mol −1
Physical state	liquid
density	0.82 g cm −3
Melting point	−35 ° C
boiling point	151 ° C
Vapor pressure	4.5 hPa (20 ° C); 6.45 hPa (30 ° C); 11.9 hPa (40 ° C); 21 hPa (50 ° C);
solubility	poorly soluble in water (4.3 g l −1 at 20 ° C)
Refractive index	1.4007 (20 ° C, 589 nm)
safety instructions
H and P phrases	H: 226-302 + 332
	P: 210
MAK	Switzerland: 50 ml m −3 or 235 mg m −3
Toxicological data	1670 mg kg −1 ( LD 50 , rat , oral ) ; 10,300 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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-Heptanone is a chemical compound from the group of ketones .

Occurrence

The typical smell of Gorgonzola is based on 2-heptanone.

2-heptanone is a rat alarm pheromone, e.g. B. the brown rat ( Rattus norvegicus ).

2-heptanone occurs naturally as a component of mold odor (e.g. also blue cheese) and blackberries. It is an alarm pheromone in rats.

Extraction and presentation

2-Heptanone can be obtained by reductive condensation of acetone with butyraldehyde in one or two steps, by a ketone decomposition of ethyl butyl acetoacetate or by hydration of 1-heptyne and 2-heptyne .

properties

2-Heptanone is a slightly volatile, colorless liquid with a fruity odor (also spicy like cinnamon) that is sparingly soluble in water.

use

2-Heptanone is used as a high boiler in coating materials. By reaction with ethylmagnesium bromide can be 3-methyl-3-octanol can be obtained.

safety instructions

The vapors of 2-heptanone can - like almost all other liquid organic substances - form an explosive mixture with air ( flash point 39.5 ° C, ignition temperature 305 ° C, lower explosion limit 1.11 vol.%, Upper explosion limit 7.9 vol .-%) form.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on 2-heptanone in the GESTIS substance database of the IFA , accessed on October 23, 2018(JavaScript required) .
↑ Data sheet 2-heptanone (PDF) from Merck , accessed on December 19, 2012.
↑ Entry on Heptan-2-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 110-43-0 or 2-heptanone ), accessed on November 2, 2015.
↑ Robert Ebermann, Ibrahim Elmadfa: Textbook food chemistry and nutrition . Springer DE, 2011, ISBN 3-7091-0210-3 , pp. 424 ( limited preview in Google Book search).
↑ Wolfgang Legrum: Fragrances, between stench and fragrance: occurrence, properties and ... Springer DE, 2011, ISBN 3-8348-1245-5 , p. 13.67 ( limited preview in Google Book Search).
^ Entry on 2-heptanone in the Hazardous Substances Data Bank , accessed December 19, 2012.
^ Sabine Krist, Gerhard Buchbauer, Carina Klausberger: Lexicon of vegetable fats and oils . Springer, 2008, ISBN 3-211-75606-X , p. 239 ( limited preview in Google Book search).
↑ Wolfgang Mücke, Christa Lemmen: Scent and smell: Effects and health significance of odorous substances . Hüthig Jehle Rehm, 2010, ISBN 3-609-16436-0 , p. 74 ( limited preview in Google Book search).
↑ Allan F. Sowinski, George M. Whitesides: SN2 displacements and reductive coupling of ketones with olefins in N, N-diethylacetamide and N-ethylpyrrolidone. In: The Journal of Organic Chemistry. 44, 1979, p. 2369, doi : 10.1021 / jo01328a008 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on 2-heptanone in the GESTIS substance database of the IFA , accessed on October 23, 2018(JavaScript required) .

[Merck-2] Data sheet 2-heptanone (PDF) from Merck , accessed on December 19, 2012.

[CLP_100.003.426-3] Entry on Heptan-2-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[4] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 110-43-0 or 2-heptanone ), accessed on November 2, 2015.

[Robert_Ebermann,_Ibrahim_Elmadfa-5] Robert Ebermann, Ibrahim Elmadfa: Textbook food chemistry and nutrition . Springer DE, 2011, ISBN 3-7091-0210-3 , pp. 424 ( limited preview in Google Book search).

[Wolfgang_Legrum-6] Wolfgang Legrum: Fragrances, between stench and fragrance: occurrence, properties and ... Springer DE, 2011, ISBN 3-8348-1245-5 , p. 13.67 ( limited preview in Google Book Search).

[HSDB-7] Entry on 2-heptanone in the Hazardous Substances Data Bank , accessed December 19, 2012.

[Sabine_Krist,_Gerhard_Buchbauer,_Carina_Klausberger-8] Sabine Krist, Gerhard Buchbauer, Carina Klausberger: Lexicon of vegetable fats and oils . Springer, 2008, ISBN 3-211-75606-X , p. 239 ( limited preview in Google Book search).

[Wolfgang_Mücke,_Christa_Lemmen-9] Wolfgang Mücke, Christa Lemmen: Scent and smell: Effects and health significance of odorous substances . Hüthig Jehle Rehm, 2010, ISBN 3-609-16436-0 , p. 74 ( limited preview in Google Book search).

[DOI10.1021/jo01328a008-10] Allan F. Sowinski, George M. Whitesides: SN2 displacements and reductive coupling of ketones with olefins in N, N-diethylacetamide and N-ethylpyrrolidone. In: The Journal of Organic Chemistry. 44, 1979, p. 2369, doi : 10.1021 / jo01328a008 .