Cyclohexanone
[CAS# 108-94-1]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: Cyclohexanone
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• CAS Registry Number: 108-94-1
• EC Number: 203-631-1
• SMILES: C1CCC(=O)CC1

Properties

• Density: 0.947
• Melting point: -47 °C
• Boiling point: 155 °C
• Refractive index: 1.445-1.456
• Flash point: 46 °C
• Water solubility: 150 g/L (10 °C)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H302+H312+H315-H318-H332
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P354+P338-P317-P321-P330-P332+P317-P362+P364-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H311
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	2	H225
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Germ cell mutagenicity	Muta.	2	H341
Specific target organ toxicity - single exposure	STOT SE	2	H371
Specific target organ toxicity - single exposure	STOT SE	3	H336
Reproductive toxicity	Repr.	2	H361
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	1	H370
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 1915

Discovery and Applications

Cyclohexanone is an organic compound classified as a cyclic ketone with the molecular formula C6H10O. It is a clear, oily liquid with a distinct odor, resembling that of acetone or peppermint. The discovery of cyclohexanone dates back to the early developments in organic chemistry, where it was initially synthesized through the oxidation of cyclohexanol. As industrial processes advanced, cyclohexanone became an important intermediate in chemical manufacturing due to its versatile chemical reactivity and role in the production of various valuable materials.

One of the primary uses of cyclohexanone is in the production of nylon, a widely used synthetic polymer. Nylon is synthesized from adipic acid and hexamethylene diamine, both of which are derived from cyclohexanone. The material is essential in the manufacturing of textiles, plastics, and engineering materials. The production of cyclohexanone for nylon manufacturing represents one of the largest industrial applications of this compound, and it remains a crucial step in the global nylon supply chain.

Cyclohexanone is also widely used as a solvent in various industries. Due to its strong solvency power, it is effective in dissolving resins, polymers, and fats. This makes it a useful solvent in the paint, coating, and adhesive industries. Its ability to dissolve a wide range of materials while maintaining relatively low toxicity and high evaporation rate makes it a popular choice in formulations requiring quick drying and smooth application.

In the pharmaceutical industry, cyclohexanone serves as a building block for the synthesis of active pharmaceutical ingredients (APIs). It is often used in the preparation of drugs and fine chemicals, contributing to the development of numerous medicinal compounds. Its reactivity as a ketone allows for various transformations in organic synthesis, leading to a broad range of pharmaceutical applications.

Additionally, cyclohexanone is employed in the production of agrochemicals and other specialty chemicals. Its ability to act as a solvent and reactant in chemical processes ensures its continued demand across different sectors.

References

2008. The effect of ring size on vibrational spectroscopy and hydrogen bonding properties for the complexes between small ring carbonyl compounds with HF and HCl: Theoretical analysis. Journal of Molecular Modeling.
DOI: 10.1007/s00894-008-0359-z

2007. Ionization and Tautomerization of 2-Nitrocyclohexanone in Aqueous Solution. The Journal of Organic Chemistry.
DOI: 10.1021/jo0700629

1979. Toxicological aspects of cyclohexanone. Toxicology and Applied Pharmacology.
DOI: 10.1016/0041-008x(79)90454-x