What Is Cyclooctane?
Cyclooctane is an organic compound, a cycloalkane (alicyclic compound) with a saturated 8-membered ring structure.
Its molecular formula is C8H16 and its CAS number is 292-64-8. It has a molecular weight of 112.21, a melting point of 12-14°C, and a boiling point of 150°C. At room temperature, it is a clear colorless to brown liquid.
It has a camphor-like odor (however, its molecular structure is completely different from camphor, a component of camphor). It is soluble in ethanol and acetone, but hardly soluble in water. Its solubility in water is 7.90 mg/L. It has a density of 0.836 g/mL (20°C) and a flash point of 30°C.
Uses of Cyclooctane
Cyclooctane is mainly used as a solvent and reagent. It is also useful as a synthetic intermediate, for example, as an intermediate in the manufacture of plastics, fibers, adhesives, and coatings.
Academically, it is also a representative of saturated 8-membered ring compounds, and its stereoconformation has been extensively studied using computational chemistry techniques.
Properties of Cyclooctane
The chemistry of cyclooctane includes combustion reactions and free radical halogenation reactions, which are typical of saturated hydrocarbons. For example, cyclooctane can be aminated by using a peroxide, such as dicumyl peroxide and nitrobenzene.
Although stable under normal storage conditions, in storage it should be kept away from high temperatures, direct sunlight, heat, flames, sparks, and static electricity. Mixture with strong oxidizing agents is also strictly prohibited. Hazardous decomposition products include carbon monoxide and carbon dioxide.
Types of Cyclooctane
Cyclooctane is sold primarily as a reagent product for research and development. The volume types include 25 mL, 500 mL, and others. It is a reagent that can be handled at room temperature. However, it has a low flash point and is a compound regulated by the Fire Service Law, so it must be handled in compliance with the law.
Cyclooctane d-16, in which all hydrogen atoms are replaced with deuterium, is also available as a reagent product. This substance is used as a heavy solvent for NMR analysis. It is expensive due to the large number of deuterium atoms and is used in special cases where other solvents cannot be used.
Other Information on Cyclooctane
1. Synthesis of Cyclooctane
Cyclooctane can be synthesized by hydrogenating Cyclooctadiene to saturated hydrocarbons. Compounds such as the intermediate 1,5-cyclooctadiene are first synthesized by dimerization of butadiene using a nickel(0) complex such as bis(cyclooctadiene)nickel as a catalyst.
Cyclooctane is synthesized by hydrogenation of cyclooctadiene by catalytic reduction.
2. Conformation of Cyclooctane
Cyclooctane is a cycloalkane with a very complex stereochemistry due to the presence of several stereoconfigurations with similar energies. The conformations include boat-chair, canned, bucket, boat-boat, twisted boat-chair, and twisted chair-chair. The most stable configuration is reported to be boat-ice.
3. Regulatory Information and Precautions for Handling Cyclooctane
Cyclooctane has a low flash point of 30°C and is a highly flammable liquid and vapor.
Fire prevention includes the use of explosion-proof electrical equipment, ventilation equipment, and lighting equipment, the use of spark-proof tools, and measures to prevent electrostatic discharge. In addition, protective equipment such as protective gloves, protective clothing, protective glasses, and protective masks must be worn when handling this substance.
If it adheres to the skin, it is necessary to remove all contaminated clothing immediately and wash the skin under running water. Also, if swallowed and enters the respiratory tract, it may be life-threatening and extremely dangerous.