Cycloheptanone

Cycloheptanone
Names
IUPAC name
Cycloheptanone
Other names
Suberone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.216
Properties
C7H12O
Molar mass 112.17 g·mol−1
Appearance Colorless liquid
Density 0.949 g/cm3 (20 °C)[1]
Boiling point 179 to 181 °C (354 to 358 °F; 452 to 454 K)[1]
Insoluble
Hazards
R-phrases (outdated) R41[2]
S-phrases (outdated) S23 S24/25 S26 S39[2]
Flash point 56 °C (133 °F; 329 K)[2]
Related compounds
Cyclohexanone, Cyclooctanone, Tropinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

  1. 1 2 The Merck Index, 11th Edition, 2728
  2. 1 2 3 Cycloheptanone at Sigma-Aldrich
  3. ↑ Thorpe, T. E. (1912). A Dictionary of Applied Chemistry. LCCN 12009914.
  4. 1 2 Siegel, H.; Eggersdorfer, M., "Ketones", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a15_077
  5. 1 2 Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19. ; Collective Volume, 4, p. 221
  6. ↑ Cornils, B.; Lappe, P., "Dicarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_523.pub2
  7. ↑ "Dicarboxylic Acids". cyberlipids.org.
  8. ↑ Lemiere, G. L.; Alderweireldt, F. C.; Voets, J. P. (1975). "Reduction of cycloalkanones by several microorganisms". Zeitschrift für Allgemeine Mikrobiologie. 15 (2): 89–92. doi:10.1002/jobm.19750150204.
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