Cycloheptanone

Structural formula
General
Surname	Cycloheptanone
other names	Suberone
Molecular formula	C 7 H 12 O
Brief description	flammable colorless liquid with a fruity odor
External identifiers / databases
EC number	207-937-6
ECHA InfoCard	100.007.216
PubChem	10400
Wikidata	Q413525
properties
Molar mass	112.17 g mol −1
Physical state	liquid
density	0.95 g cm −3
Melting point	−21 ° C
boiling point	179 ° C
solubility	practically insoluble in water; easily soluble in ethanol and diethyl ether ;
Refractive index	1.461 (20 ° C)
safety instructions
H and P phrases	H: 226-302-332-319
	P: 210-261-301 + 312-305 + 351 + 338
	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

Cycloheptanone is a chemical compound from the group of ketones .

Extraction and presentation

Cycloheptanone was first in 1836 by the French chemist Jean-Baptiste Boussingault starting from the calcium salt of dibasic suberic ( Calciumsuberat shown). From this he obtained calcium carbonate and cycloheptanone by heating ("dry distillation") :

{\ displaystyle \ mathrm {CaO_ {2} C (CH_ {2}) _ {6} CO_ {2} \ longrightarrow CaCO_ {3} + (CH_ {2}) _ {6} CO}}

Cycloheptanone can also be obtained by cyclization and decarboxylation of suberic acid or its esters.

The synthesis is also possible by a reaction starting from cyclohexanone with sodium ethoxide and nitromethane and a subsequent reaction with acetic acid and sodium nitrite .

It can also be obtained by ring expansion of cyclohexanone with diazomethane .

properties

Cycloheptanone is a flammable colorless liquid with a fruity odor, which is practically insoluble in water.

use

Cycloheptanone is used as an intermediate in the manufacture of other chemical compounds such as bencyclan and pimelic acid .

Biological importance

Various microorganisms , including Echinosporangium transversale , Absidia glauca and Mucor plumbeus , are able to reduce cycloheptanone to cycloheptanol .

safety instructions

The vapors of cycloheptanone can form an explosive mixture with air ( flash point 55 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on cycloheptanone in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. CRC Press, 2009, ISBN 978-1-4200-9084-0 .
↑ Data sheet cycloheptanone, 99% from Sigma-Aldrich , accessed on November 29, 2011 ( PDF ).
↑ Thorpe, TE; A dictionary of applied chemistry. 1912.
↑ ^a ^b Siegel, H .; Eggersdorfer, M. (2005), Ketones , Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi : 10.1002 / 14356007.a15_077
↑ ^a ^b Hyp J. Dauben, Jr., Howard J. Ringold, Robert H. Wade, David L. Pearson, and Arthur G. Anderson, Jr .: Cycloheptanone In: Organic Syntheses . 34, 1954, p. 19, doi : 10.15227 / orgsyn.034.0019 ; Coll. Vol. 4, 1963, p. 221 ( PDF ).
↑ Cornils, B .; Lappe, P. (2005): Dicarboxylic Acids, Aliphatic , Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi : 10.1002 / 14356007.a08_523.pub2
Jump up ↑ Lemière, GL, van De Wal, AJ, Geens, BC, Pattijn, VG, Alderweireldt, FC, Voets, JP: Reduction of cycloalkanones by several microorganisms . In: Journal of General Microbiology . 15, No. 2, 1975, pp. 1521-4028. doi : 10.1002 / jobm.19750150204 .
↑ José D. Carballeira, Emilio Álvarez, Mercedes Campillo, Leonardo Pardo, José V. Sinisterra: Diplogelasinospora grovesii IMI 171018, a new whole cell biocatalyst for the stereoselective reduction of ketones . In: Tetrahedron: Asymmetry . 15, No. 6, March 2004, pp. 951-962. doi : 10.1016 / j.tetasy.2004.01.034 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on cycloheptanone in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[CRC-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. CRC Press, 2009, ISBN 978-1-4200-9084-0 .

[Sigma-3] Data sheet cycloheptanone, 99% from Sigma-Aldrich , accessed on November 29, 2011 ( PDF ).

[4] Thorpe, TE; A dictionary of applied chemistry. 1912.

[ketones-5] Siegel, H .; Eggersdorfer, M. (2005), Ketones , Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi : 10.1002 / 14356007.a15_077

[organic_syntheses-6] Hyp J. Dauben, Jr., Howard J. Ringold, Robert H. Wade, David L. Pearson, and Arthur G. Anderson, Jr .: Cycloheptanone In: Organic Syntheses . 34, 1954, p. 19, doi : 10.15227 / orgsyn.034.0019 ; Coll. Vol. 4, 1963, p. 221 ( PDF ).

[7] Cornils, B .; Lappe, P. (2005): Dicarboxylic Acids, Aliphatic , Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi : 10.1002 / 14356007.a08_523.pub2

[Lemiere-8] Jump up ↑ Lemière, GL, van De Wal, AJ, Geens, BC, Pattijn, VG, Alderweireldt, FC, Voets, JP: Reduction of cycloalkanones by several microorganisms . In: Journal of General Microbiology . 15, No. 2, 1975, pp. 1521-4028. doi : 10.1002 / jobm.19750150204 .

[Carbelleira-9] José D. Carballeira, Emilio Álvarez, Mercedes Campillo, Leonardo Pardo, José V. Sinisterra: Diplogelasinospora grovesii IMI 171018, a new whole cell biocatalyst for the stereoselective reduction of ketones . In: Tetrahedron: Asymmetry . 15, No. 6, March 2004, pp. 951-962. doi : 10.1016 / j.tetasy.2004.01.034 .