- Cycloheptanone
-
Cycloheptanone 
CycloheptanoneOther namesSuberoneIdentifiers CAS number 502-42-1 
PubChem 10400 ChemSpider 9971 ChEMBL CHEMBL18607 Jmol-3D images Image 1 - O=C1CCCCCC1
- InChI=1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2
Key: CGZZMOTZOONQIA-UHFFFAOYSA-N
Properties Molecular formula C7H12O Molar mass 112.17 g mol−1 Appearance Colorless liquid Density 0.949 g/cm3 (20 °C)[1] Boiling point 179-181 °C[1]
Solubility in water Insoluble Hazards R-phrases R41[2] S-phrases S23 S24/25 S26 S39[2] Flash point 56 °C[2] Related compounds Related cyclic ketones Cyclohexanone, Cyclooctanone, Tropinone 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Cycloheptanone, (CH2)6CO, is a cyclic ketone also referred to as suberone. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals.
Synthesis
In 1836, French chemist Jean-Baptiste Boussingault first synthesized cycloheptanone from the calcium salt of dibasic suberic acid. The destructive distillation of calcium suberate yields calcium carbonate and suberone:[3]
- Ca(O2C(CH2)6CO2) → CaCO3 + (CH2)6CO
Cycloheptanone is still produced by the cyclization and decarboxylation of suberic acid or suberic acid esters. This reaction is typically conducted in the gas phase at 400 – 450 °C over alumina doped with zinc oxide or cerium oxide.[4]
Cycloheptanone is also produced by the reaction of cyclohexanone with sodium ethoxide and nitromethane. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to acetic acid and shaken with hydrogen gas in the presence of W-4 Raney nickel catalyst. Sodium nitrite and acetic acid are then added to give cycloheptanone.[5]
Cycloheptanone is also prepared by ring expansion of cyclohexanone with diazomethane as the methylene source.[5]
Uses and reactions
Cycloheptanone has no direct applications, but is a precursor to other compounds. Bencyclane, a spasmolytic agent and vasodilator is produced from it, for example.[4] Pimelic acid is produced by the oxidative cleavage of cycloheptanone.[6] Dicarboxylic acids such as pimelic acid are useful for the preparation of fragrances and certain polymers.[7]
Several microorganisms, including Mucor plumbeus, Mucor racemosus, and Penicillium chrysogenum, have been found to reduce cycloheptanone to cycloheptanol. These microorganisms have been investigated for use in certain stereospecific enzymatic reactions.[8]
References
- ^ a b The Merck Index, 11th Edition, 2728
- ^ a b c Cycloheptanone at Sigma-Aldrich
- ^ Thorpe, T. E.; 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. (1963), "Cycloheptanone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0221; Coll. Vol. 4: 221
- ^ Cornils, B.; Lappe, P. (2005), "Dicarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_523.pub2
- ^ Dicarboxylic Acids. http://www.cyberlipid.org/fa/acid0004.htm
- ^ Lemiere, G. L.; Alderweireldt, F. C.; Voets, J. P.; “Reduction of cycloalkanones by several microorganisms” Zeitschrift für Allg. Mikrobiologie, 1975. 15 (2), pp 89-92. DOI: 10.1002/jobm.19750150204
Categories:- Ketones
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