Musk ketone

Structural formula
General
Surname	Musk ketone
other names	Ketone musk; Musk ketone; 4- tert -butyl-2,6-dimethyl-3,5-dinitroacetophenone; 1- (4- tert -butyl-2,6-dimethyl-3,5-dinitrophenyl) ethanone;
Molecular formula	C 14 H 18 N 2 O 5
Brief description	yellowish solid with a musky, powdery, animal odor
External identifiers / databases
EC number	201-328-9
ECHA InfoCard	100.001.209
PubChem	6669
Wikidata	Q1948992
properties
Molar mass	294.31 g mol −1
Physical state	firmly
density	1.29 g cm −3
Melting point	134-137 ° C
solubility	practically insoluble in water (1.9 mg l −1 )
safety instructions
H and P phrases	H: 351-410
	P: 273-281-501
Toxicological data	> 10000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Musk ketone is a chemical compound from the group of ketones and aromatic nitro compounds .

properties

Musk ketone is a yellowish solid with a musky , powdery, animal odor, which is practically insoluble in water. The scent of the artificial fragrance musk-ketone comes closest to that of natural musk. Musk ketone is easily soluble in alcohol, ether or benzene.

use

Musk ketone is used as a fragrance in cosmetics and consumer products (detergents and cleaning agents, fragrance improvers, incense sticks). In 1998, 40 tons of musk ketone were processed in Europe for this purpose.

Historical

The chemist and factory director Albert Baur had already produced nitroaromatics, possibly initially in connection with explosives research. After he noticed that the nitrated propylbenzene smelled musky, he had "patented the production of this artificial musk [...] in all countries" and marketed the product. In the course of his further research he discovered the musk ketone; he published this in 1898. The musk xylene , which has been banned in the EU since 2014 and was also used on a ton scale, was also discovered by Baur.

presentation

Musk ketone can be obtained from butyl xylene by first converting it into 4- tert- butyl-2,6-dimethyl acetophenone with acetyl chloride . The musk ketone is obtained from this by nitrating with nitric acid at 0 ° C.

safety instructions

Musk ketone is suspected to have a carcinogenic effect.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on musk ketone in the GESTIS substance database of the IFA , accessed on February 13, 2017(JavaScript required) .
↑ Entry on 4′-tert-butyl-2 ′, 6′-dimethyl-3 ′, 5′-dinitroacetophenone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can use the expand harmonized classification and labeling .
^ Edward Sagarin: The Science And Art Of Perfumery . First ed. McGraw-Hill, New York, London 1945, The Genealogy of a Formula, pp. 117 (English, online in the Internet Archive): “closest to the natural musk in its odor”
↑ ^a ^b Wolfgang Legrum: Fragrances, between stench and fragrance: Occurrence, properties and use of fragrances and their mixtures . 2., revised. and exp. Springer Fachmedien Wiesbaden, Wiesbaden 2015, ISBN 978-3-658-07309-1 , p. 166–167 , doi : 10.1007 / 978-3-658-07310-7 ( limited preview in Google book search).
↑ ^a ^b ^c Albert Baur-Thurgau: About ketone musk . In: Deutsche Chemische Gesellschaft, P. Jacobson (Hrsg.): Reports of the German chemical society . tape 31 , no. 2 . Friedländer & Sohn, Berlin May 1898, p. 1344–1349 , doi : 10.1002 / cber.18980310217 ( online at Gallica Bibliothèque nationale de France).
↑ Fact Sheet nitro musk compounds ( Memento from November 12, 2011 in the Internet Archive ). Federal Environment Agency (PDF; 40 kB).
↑ Musk ketones. In: American Chemical Society> Molecule of the Week> Molecule of the Week Archive> Archive - M> Musk ketone. American Chemical Society, May 8, 2017, accessed May 19, 2019 .
↑ Albert Baur: Studies on the artificial musk . In: Ferd. Tiemann, F. v. Dechend (Ed.): Reports of the German Chemical Society . tape 24 , no. 2 . Friedländer & Sohn, Berlin July 1891, p. 2832–2843 , doi : 10.1002 / cber.189102402106 ( wiley.com [accessed May 17, 2019]).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on musk ketone in the GESTIS substance database of the IFA , accessed on February 13, 2017(JavaScript required) .

[CLP_100.001.209-2] Entry on 4′-tert-butyl-2 ′, 6′-dimethyl-3 ′, 5′-dinitroacetophenone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can use the expand harmonized classification and labeling .

[3] Edward Sagarin: The Science And Art Of Perfumery . First ed. McGraw-Hill, New York, London 1945, The Genealogy of a Formula, pp. 117 (English, online in the Internet Archive): “closest to the natural musk in its odor”

[Legrum-4] Wolfgang Legrum: Fragrances, between stench and fragrance: Occurrence, properties and use of fragrances and their mixtures . 2., revised. and exp. Springer Fachmedien Wiesbaden, Wiesbaden 2015, ISBN 978-3-658-07309-1 , p. 166–167 , doi : 10.1007 / 978-3-658-07310-7 ( limited preview in Google book search).

[Baur1898-5] Albert Baur-Thurgau: About ketone musk . In: Deutsche Chemische Gesellschaft, P. Jacobson (Hrsg.): Reports of the German chemical society . tape 31 , no. 2 . Friedländer & Sohn, Berlin May 1898, p. 1344–1349 , doi : 10.1002 / cber.18980310217 ( online at Gallica Bibliothèque nationale de France).

[6] Fact Sheet nitro musk compounds ( Memento from November 12, 2011 in the Internet Archive ). Federal Environment Agency (PDF; 40 kB).

[7] Musk ketones. In: American Chemical Society> Molecule of the Week> Molecule of the Week Archive> Archive - M> Musk ketone. American Chemical Society, May 8, 2017, accessed May 19, 2019 .

[8] Albert Baur: Studies on the artificial musk . In: Ferd. Tiemann, F. v. Dechend (Ed.): Reports of the German Chemical Society . tape 24 , no. 2 . Friedländer & Sohn, Berlin July 1891, p. 2832–2843 , doi : 10.1002 / cber.189102402106 ( wiley.com [accessed May 17, 2019]).