What Is Chlorocyclohexane?
Chlorocyclohexane is an organochlorine compound in which one hydrogen atom of cyclohexane is replaced by chlorine. Its chemical formula is C6H11Cl.
It is also called cyclohexyl chloride and exists as a liquid state with a pungent odor at room temperature.
Uses of Chlorocyclohexane
Chlorocyclohexane has various uses as an intermediate compound for agrochemical raw materials, rubber raw materials, and pharmaceuticals. The following is an example of one of these uses as a synthetic material for rubber raw materials.
Chlorocyclohexane is used to produce a substance called N-cyclohexylthiophthalimide. The phenomenon in which rubber hardens during storage or molding and becomes difficult to process is called the scorch phenomenon. N-Cyclohexylthiofthalimide acts as a scorch inhibitor in rubber processing.
Properties of Chlorocyclohexane
1. Flammability
Chlorocyclohexane is extremely flammable and is easily ignited by flame, heat or sparks. Because chlorocyclohexane contains chlorine in its composition, it can produce an irritating odor and toxic chlorine-containing gases when it burns.
Cyclocyclohexane is also highly flammable, and chlorocyclohexane, which is similar in structure to cyclohexane, is also highly flammable.
Chlorocyclohexane is less flammable than cyclohexane because of the chlorine bond. In fact, lindane, in which six of cyclohexane’s hydrogens are replaced by chlorine, is nonflammable.
2. Solubility
Chlorocyclohexane is virtually insoluble in water. Quantitative solubility is 500ml per liter of water. It is very soluble in ethanol and acetone.
3. Toxicity
Chlorocyclohexane is toxic to animals and plants, including humans. This property is used as a raw material for pesticides and insecticides.
Chlorocyclohexane is a type of organochlorine compound. Organochlorine compounds are a general term for organic compounds that contain chlorine in their molecules. Most organochlorine compounds are artificially synthesized and rarely found in nature.
Most organochlorine compounds are highly toxic, and it is said that there is no organochlorine compound that is not toxic.
The use and emission of chlorofluorocarbons (CFCs), which destroy the ozone layer, and dioxin and trihalomethane, which have attracted attention for their environmental problems, are regulated by law.
Structure of Chlorocyclohexane
1. Stereo Conformation of Chlorocyclohexane
The cyclohexane ring has a strain-free three-dimensional structure called a chair conformation. It is called chair conformation because it is shaped like a lounge chair with a backrest, a seat, and a footrest. The chair-shaped cyclohexane ring has all C-C-C bond angles of 111.5°, close to the most stable tetrahedral angle of 109.5°.
In addition to the chair configuration, the cyclohexane ring has another stereo configuration called the ship-shaped configuration. This boat-shaped configuration has no angular strain, but it does have torsional strain due to the overlapping electron orbitals of the C-H bonds between adjacent carbon atoms. Therefore, it is more unstable than the chair-shaped configuration.
2. Axial and Equatorial Bonds in Chlorocyclohexane
Chlorine attached to the cyclohexane ring can take two different positions: axial and equatorial.
The axial position is parallel to the ring axis, i.e., perpendicular to the ring, while the equatorial position is around the equator of the ring, approximately in the same plane as the ring.
The equatorial position is more stable because the chlorine at the axial position is torsionally distorted due to interference with the hydrogen at the axial position.
Other Information on Chlorocyclohexane
1. Production of Chlorocyclohexane
Chlorocyclohexane is produced by chlorination of cyclohexane or by heating cyclohexanol with hydrochloric acid.