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The Chemistry of Cyclohexylbenzene: Properties and Industrial Significance

Cyclohexylbenzene, identified by its CAS number 827-52-1, is a fascinating organic compound that holds significant importance in the chemical industry. Chemically, it is an aromatic hydrocarbon where a benzene ring is substituted with a cyclohexyl group. This structure imbues it with a unique set of properties, making it a valuable asset in various industrial applications, primarily as a high-boiling point solvent and a crucial intermediate in organic synthesis. For procurement managers and research scientists, understanding the chemistry behind cyclohexylbenzene is fundamental to its effective utilization.

The synthesis of cyclohexylbenzene typically involves the acid-catalyzed alkylation of benzene. One common method is the reaction of benzene with cyclohexene in the presence of a strong acid catalyst like sulfuric acid. This reaction proceeds efficiently, producing cyclohexylbenzene along with potentially other alkylated products depending on reaction conditions. Another route is the Friedel-Crafts alkylation of benzene with cyclohexyl chloride, catalyzed by Lewis acids such as aluminum chloride. These synthesis pathways are well-established and allow for the industrial-scale production of cyclohexylbenzene, making it readily available from manufacturers worldwide.

The utility of cyclohexylbenzene stems from its distinct properties. Its high boiling point (around 240°C) makes it suitable for processes that require elevated temperatures where lower-boiling solvents would evaporate. As a solvent, it is effective for dissolving a wide range of organic compounds, acting as a penetrant in applications like plastics and adhesives. Its chemical structure also makes it a versatile intermediate. It can be readily functionalized or used in rearrangement reactions.

Perhaps the most industrially significant transformation involving cyclohexylbenzene is its use in a process analogous to the cumene process for producing phenol. Cyclohexylbenzene is oxidized to form its hydroperoxide. This hydroperoxide then undergoes a Hock rearrangement, cleaving to yield phenol and cyclohexanone. Both phenol and cyclohexanone are vital commodity chemicals. Phenol is a key ingredient in resins, plastics, and pharmaceuticals, while cyclohexanone is a precursor to nylon. This route highlights cyclohexylbenzene's strategic importance in the production of essential industrial materials.

Beyond these applications, cyclohexylbenzene is also investigated and used in more specialized areas. It serves as an intermediate in the synthesis of materials for liquid crystal displays (LCDs) and has been explored as an additive for lithium-ion battery electrolytes to enhance safety. These emerging applications demonstrate the compound's adaptability to new technological demands.

When sourcing cyclohexylbenzene, buyers should pay close attention to its specifications, such as purity, appearance, and CAS number (827-52-1). Partnering with reputable manufacturers and suppliers ensures consistent quality and a reliable supply chain, whether for large-scale industrial use or specialized research applications. The accessibility and established manufacturing processes of cyclohexylbenzene ensure its continued relevance in the chemical industry.

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