cyclohexanone

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/14 22:10:02」(JST)

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Cyclohexanone
Identifiers
CAS number	108-94-1 Y
PubChem	7967
ChemSpider	7679 Y
UNII	5QOR3YM052 Y
DrugBank	DB02060
KEGG	C00414 Y
ChEBI	CHEBI:17854 Y
ChEMBL	CHEMBL18850 Y
Jmol-3D images	Image 1
SMILES C1CCC(=O)CC1
InChI InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 Y Key: JHIVVAPYMSGYDF-UHFFFAOYSA-N Y InChI=1/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 Key: JHIVVAPYMSGYDF-UHFFFAOYAY
Properties
Molecular formula	C6H10O
Molar mass	98.15 g/mol
Appearance	Colorless liquid
Odor	peppermint or acetone-like
Density	0.9478 g/mL, liquid
Melting point	−47 °C (−53 °F; 226 K)
Boiling point	155.65 °C (312.17 °F; 428.80 K)
Solubility in water	8.6 g/100 mL (20 °C)
Solubility in all organic solvents	Miscible
Refractive index (nD)	1.447
Viscosity	2.02 cP at 25 °C
Thermochemistry
Std molar entropy So298	+229.03 J.K−1.mol−1
Std enthalpy of formation ΔfHo298	−270.7 kJ mol−1
Std enthalpy of combustion ΔcHo298	−3519.3 kJmol−1
Hazards
EU classification	Harmful (Xn)
R-phrases	R10, R20
S-phrases	(S2), S25
NFPA 704	2 1 0
Flash point	44 °C (111 °F; 317 K)
Autoignition temperature	420 °C (788 °F; 693 K)
Explosive limits	1.1-9.4%
Related compounds
Related ketones	Cyclopentanone, cycloheptanone
Related compounds	Cyclohexanol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Cyclohexanone is the organic compound with the formula (CH₂)₅CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of peardrop sweets as well as acetone. Over time, samples assume a yellow color due to oxidation. Cyclohexanone is slightly soluble in water, but miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.

Production

Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:

C₆H₁₂ + O₂ → (CH₂)₅CO + H₂O

This process co-forms cyclohexanol, and this mixture, called "KA oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C₆H₁₁O₂H. In some cases, purified cyclohexanol, obtained by hydration of cyclohexene, is the precursor. Alternatively, cyclohexanone can be produced by the partial hydrogenation of phenol:

C₆H₅OH + 2 H₂ → (CH₂)₅CO

This process can also be adjusted to favor the formation of cyclohexanol.

Laboratory methods

Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide (Jones oxidation). An alternative method utilizes the safer and more readily available oxidant sodium hypochlorite.

Uses

The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon 6. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 6,6. For this application, the KA oil (see above) is oxidized with nitric acid. The other half of the cyclohexanone supply is converted to the oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:

Safety

Like cyclohexanol, cyclohexanone is not carcinogenic and is only moderately toxic, with a TLV of 25 ppm for the vapor. It is an irritant.

A recent study of plastic tubing used in medical procedures that circulate blood outside the body suggests a link between this compound and decreased heart function, swelling, loss of taste and short term memory loss.

References

UpToDate Contents

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• 1. 成人におけるフェンシクリジン（PCP）中毒 phencyclidine pcp intoxication in adults
• 2. 小児や青年のフェンシクリジン（PCP）中毒 phencyclidine pcp intoxication in children and adolescents

English Journal

• Electrospinning of Grooved Polystyrene Fibers: Effect of Solvent Systems.

• Liu W1, Huang C, Jin X.
• Nanoscale research letters.Nanoscale Res Lett.2015 Dec;10(1):949. doi: 10.1186/s11671-015-0949-5. Epub 2015 May 27.
• Secondary surface texture is of great significance to morphological variety and further expands the application areas of electrospun nanofibers. This paper presents the possibility of directly electrospinning grooved polystyrene (PS) fibers using both single and binary solvent systems. Solvents were
• PMID 26055481

• Directed evolution of phenylacetone monooxygenase as an active catalyst for the baeyer-villiger conversion of cyclohexanone to caprolactone.

• Parra LP1,2,3, Acevedo JP1,2,4, Reetz MT5,6.
• Biotechnology and bioengineering.Biotechnol Bioeng.2015 Jul;112(7):1354-64. doi: 10.1002/bit.25564. Epub 2015 Apr 30.
• Phenylacetone monooxygenase (PAMO) is an exceptionally robust Baeyer-Villiger monooxygenase, which makes it ideal for potential industrial applications. However, its substrate scope is limited, unreactive cyclohexanone being a prominent example. Such a limitation is unfortunate, because this particu
• PMID 25675885

• Inhibition of amyloid fibril formation and cytotoxicity by a chemical analog of Curcumin as a stable inhibitor.

• Ramshini H1, Mohammad-Zadeh M2, Ebrahim-Habibi A3.
• International journal of biological macromolecules.Int J Biol Macromol.2015 Jul;78:396-404. doi: 10.1016/j.ijbiomac.2015.04.038. Epub 2015 Apr 28.
• Clinical application of curcumin for Alzheimer's disease treatment is severely limited with regard to its poor bioavailability, high rate of metabolism, and instability under neutral condition. In the current study, we designed three compounds in which the diketone moiety of curcumin was replaced by
• PMID 25931400

Japanese Journal

• Electron and Hole Transfer in Anion-Bound Chemically Amplified Resists Used in Extreme Ultraviolet Lithography

• Komuro Yoshitaka,Yamamoto Hiroki,Utsumi Yoshiyuki,Ohomori Katsumi,Kozawa Takahiro
• Applied Physics Express 6(1), 014001-014001-4, 2013-01-25
• … In this study, the reaction mechanism of an anion-bound polymer in cyclohexanone was clarified using pulse radiolysis. …
• NAID 150000106245

• 31. AM菌のストリゴラクトン受容体単離のための高活性型光親和性プローブの合成(口頭発表,植物化学調節学会第46回大会)

• 秋山 康紀,中谷 成史,林 英雄
• 植物化学調節学会研究発表記録集 (46), 47, 2011-10-03
• … 8-Desmethylsorgolactone (8-dMS) synthesized from cyclohexanone exhibited strong but slightly weaker activity than 5-deoxystrigol (5DS) (10 pg/disc vs 3 pg/disc). …
• NAID 110008902440

• Transfer hydrogenation of ketones catalyzed by PEG-armed ruthenium-microgel star polymers: microgel-core reaction space for active, versatile and recyclable catalysis

• TERASHIMA Takaya,OUCHI Makoto,ANDO Tsuyoshi,SAWAMOTO Mitsuo
• Polymer journal 43(9), 770-777, 2011-09-15
• … For example, the turnover frequency for 4-chloroacetophenone and cyclohexanone reached ~1000 h−1, and the reduction rate of cyclopentanone and 3-methyl-5-heptanone was twice as high as that of RuCl2(PPh3)3. …
• NAID 10029472379

Related Links

• Cyclohexanone - Wikipedia, the free encyclopedia

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of peardrop sweets as well as acetone.

• Cyclohexanone | C6H10O | ChemSpider

Structure, properties, spectra, suppliers and links for: Cyclohexanone, 51209-49- 5.

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