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| cyclopentane | |
|---|---|
| Name | Cyclopentane |
| Pin | Cyclopentane |
| Other names | Cyclopentane |
| Formula | C5H10 |
| Molar mass | 70.13 g·mol−1 |
| Density | 0.745 g·cm−3 (20 °C) |
| Melting point | −94 °C |
| Boiling point | 49 °C |
| Solubility | Insoluble in water |
cyclopentane Cyclopentane is a saturated hydrocarbon and a member of the cycloalkane family, notable for its five-membered ring and relevance in industrial chemistry, organic synthesis, and physical chemistry. It has been studied across contexts ranging from thermodynamics experiments in Niels Bohr-era physical chemistry labs to applications in refrigeration development by companies associated with DuPont and Honeywell. Its conformational behavior and reactivity have been discussed in reviews influenced by researchers affiliated with institutions such as Massachusetts Institute of Technology, University of Cambridge, and Stanford University.
The molecular structure of cyclopentane consists of a planar five-carbon ring with formula C5H10; however, low-energy conformations are nonplanar and were characterized by spectroscopists and theorists associated with Royal Society-sponsored programs and groups in laboratories at California Institute of Technology and Max Planck Society. Early X-ray and electron diffraction studies by scientists at University of Oxford and University of Paris revealed envelope and twist conformations analogous to conformational analyses developed by researchers from University of Chicago and Columbia University. Computational work using methods from teams at Los Alamos National Laboratory and Argonne National Laboratory confirmed ring puckering parameters originally proposed in seminars at Harvard University and refined with techniques from ETH Zurich. Conformational interconversion barriers were mapped using spectroscopic methods that trace back to equipment produced by firms like Agilent Technologies and Bruker.
Cyclopentane is a colorless, volatile liquid at room temperature with physical constants measured and cataloged in handbooks used at National Institute of Standards and Technology and cited by industrial databases maintained by American Chemical Society publications and Royal Society of Chemistry reference works. Its vapor pressure and critical properties were determined in studies involving researchers from Imperial College London and Princeton University, and these data are used in thermodynamic models developed at Lawrence Berkeley National Laboratory and Oak Ridge National Laboratory. Cyclopentane displays typical alkane C–H stretching in infrared spectra measured on instruments from PerkinElmer and Thermo Fisher Scientific, and its NMR chemical shifts were assigned in experiments reported in journals associated with Nature Research and Wiley-Blackwell. Physical properties such as refractive index and viscosity were tabulated in compendia edited by panels convened at World Health Organization-affiliated conferences.
Industrial production of cyclopentane has historically involved catalytic processes and cracking schemes developed by petrochemical companies like ExxonMobil, Shell plc, and BP. Laboratory syntheses drawing on methodologies from organic chemists at Scripps Research and Yale University include hydrogenation of cyclopentene and ring-closing routes refined by research groups at University of California, Berkeley and Johns Hopkins University. Catalysts employed in production-scale and bench-scale reactions derive from studies sponsored by agencies such as United States Department of Energy and European Commission, with metal catalysts and zeolites characterized in facilities at Fritz Haber Institute and Brookhaven National Laboratory. Process engineering to separate and purify cyclopentane has been advanced in collaboration with companies like ABB and Siemens AG.
Cyclopentane undergoes typical saturated hydrocarbon reactions; radical halogenation, dehydrogenation, and cracking pathways have been explored in mechanistic studies from groups at University of Michigan and McGill University. Dehydrogenation to cyclopentene and aromatization to cyclopentadiene derivatives has been catalyzed by transition metals studied at ETH Zurich and University of Tokyo. Oxidative and photochemical transformation studies reported in journals published by American Chemical Society and Royal Society illuminate reaction kinetics and intermediate species, with mechanistic proposals debated at conferences organized by Gordon Research Conferences and American Institute of Chemical Engineers. Reaction conditions, radical chain mechanisms, and catalyst lifetimes were probed using spectrometers and reactors developed by Shimadzu and Toshiba research groups.
Cyclopentane is used as a blowing agent and foam propellant in insulation materials produced by companies such as BASF, Dow Chemical Company, and Armacell and adopted in energy-efficiency programs promoted by agencies including International Energy Agency and United Nations Environment Programme. It has been implemented as a refrigerant alternative in systems designed by firms like Carrier Global Corporation and Daikin Industries following phase-down policies influenced by treaties such as the Montreal Protocol and regulations drafted by the European Union. In organic synthesis, cyclopentane serves as a solvent and substrate in methodologies developed at Roche and Pfizer research labs. Academic use in teaching laboratories at institutions like Brown University and University of Toronto illustrates ring-conformational principles discussed in textbooks from publishers such as Oxford University Press and Cambridge University Press.
Safety data and handling guidelines for cyclopentane are provided by regulatory agencies and standards bodies including Occupational Safety and Health Administration, European Chemicals Agency, and National Fire Protection Association. It is highly flammable, with fire safety practices promoted by organizations like Underwriters Laboratories and National Fire Protection Association used in facilities operated by General Electric and Siemens AG. Industrial hygiene, exposure limits, and spill response procedures have been developed in collaboration with Centers for Disease Control and Prevention and implemented in plants managed by Chevron and TotalEnergies. Storage and transport follow classification and placarding rules influenced by the International Maritime Organization and Department of Transportation.
Category:Hydrocarbons