cyclohexane

cyclohexane
Name	Cyclohexane
Formula	C6H12
Molar mass	84.16 g·mol−1
Density	0.7785 g·cm−3 (20 °C)
Melting point	6.47 °C
Boiling point	80.74 °C
CAS number	110-82-7

cyclohexane Cyclohexane is a saturated alicyclic hydrocarbon used extensively as an industrial solvent and chemical intermediate. It appears as a colorless, flammable liquid with low polarity and a characteristic odor, and it plays a central role in petrochemical refining, organic synthesis, and materials manufacture. Major chemical firms, research institutions, and government agencies have studied its conformational behavior, reactivity, and environmental fate.

Introduction

Cyclohexane occupies a prominent place in the commodity chemicals markets dominated by companies such as ExxonMobil, Shell plc, BP, TotalEnergies, and Chevron Corporation and in research programs at institutions like Massachusetts Institute of Technology, California Institute of Technology, University of Cambridge, Harvard University, and Stanford University. It is produced from feedstocks sourced by refineries and petrochemical complexes in regions overseen by organizations such as the International Energy Agency, Organisation for Economic Co-operation and Development, and national regulators including the United States Environmental Protection Agency, European Chemicals Agency, and Health and Safety Executive. Cyclohexane also figures in industrial case studies alongside molecules such as benzene, toluene, xylene, n-hexane, and cyclopentane.

Structure and Conformations

The molecular formula C6H12 describes a six-membered saturated ring; key structural analyses were advanced by scientists at Royal Society of Chemistry meetings and by investigators such as Linus Pauling and Ernest R. Becker (historical conformational work was contemporaneous with research by Dorothy Crowfoot Hodgkin and Linus Pauling-era structural chemistry). Cyclohexane adopts nonplanar conformations including the low-energy chair and higher-energy boat and twist-boat forms, concepts developed in the context of conformational analysis by researchers affiliated with University of Oxford, Yale University, Princeton University, and Columbia University. Experimental verification of ring puckering and barrier heights used spectroscopic methods refined at facilities like National Institute of Standards and Technology, European Synchrotron Radiation Facility, Brookhaven National Laboratory, and Lawrence Berkeley National Laboratory and computational studies performed using software from institutions such as IBM and Microsoft Research.

Physical and Chemical Properties

Cyclohexane exhibits characteristic thermophysical properties catalogued by National Institute of Standards and Technology and industry groups including American Chemical Society divisions and American Petroleum Institute. It is nonpolar, with limited solubility in water but good solubility in nonpolar solvents commonly used by laboratories at Max Planck Society, Scripps Research, Johns Hopkins University, and University of Tokyo. Chemical reactions of cyclohexane include free-radical halogenation studied in research programs at ETH Zurich, University of California, Berkeley, University of Illinois Urbana-Champaign, and Imperial College London; catalytic dehydrogenation to cyclohexene and benzene is developed by companies such as BASF, Dow Chemical Company, and DuPont. Its heat capacity, viscosity, and vapor pressure data inform process design in engineering groups at MIT Department of Chemical Engineering, Georgia Institute of Technology, and industrial R&D labs at Siemens and Honeywell.

Production and Synthesis

Large-scale production of cyclohexane derives from catalytic hydrogenation of benzene and fractional distillation streams in refineries operated by ExxonMobil Chemical, SABIC, LG Chem, and regional producers in the Gulf of Mexico and North Sea. Process engineering literature from American Institute of Chemical Engineers case studies and patents filed with offices such as the United States Patent and Trademark Office, European Patent Office, and Japan Patent Office document methods including hydrogenation using catalysts developed by Johnson Matthey and Umicore. Laboratory syntheses and mechanistic studies have been conducted in academic groups at University of Chicago, University of Wisconsin–Madison, Peking University, and Seoul National University, often employing transition-metal catalysis themes connected to laureates of awards like the Nobel Prize in Chemistry.

Applications and Uses

Cyclohexane serves as a precursor to adipic acid and caprolactam, linking it to global value chains involving manufacturers such as Bayer, Aditya Birla Group, DuPont, Asahi Kasei, and Mitsubishi Chemical. Those downstream products are essential for production of nylon polymers used by companies like DuPont, Rieter, Toray Industries, and Invista in textiles, automotive parts for Toyota Motor Corporation, Volkswagen, and Ford Motor Company, and industrial fibers used by 3M. Cyclohexane functions as an industrial solvent in paint and coatings sectors with producers such as AkzoNobel and PPG Industries and as a standard reference in spectroscopic laboratories at Royal Society, American Chemical Society meetings and instrument manufacturers like Agilent Technologies and Thermo Fisher Scientific. Its role in academic teaching laboratories ties to curricula from University of Oxford, University of Cambridge, and Massachusetts Institute of Technology.

Safety and Environmental Effects

Safety guidance for cyclohexane is issued by regulatory agencies such as the Occupational Safety and Health Administration, National Institute for Occupational Safety and Health, European Chemicals Agency, and Canadian Centre for Occupational Health and Safety. Fire incidents and industrial health assessments are recorded in reports by organizations like International Labour Organization and national emergency services in countries including United States, United Kingdom, Germany, Japan, and Australia. Environmental fate studies published by groups at United Nations Environment Programme, World Health Organization, and universities such as McGill University, University of British Columbia, and University of Sydney examine volatility, biodegradation, and aquatic toxicity, informing permitting by agencies such as the Environmental Protection Agency and Environment and Climate Change Canada. Risk management in supply chains draws on standards from International Organization for Standardization and industry consortia including Society of Chemical Manufacturers & Affiliates.

Category:Hydrocarbons