| | Methylcyclopentane Basic information |
| | Methylcyclopentane Chemical Properties |
| Melting point | -142.4 °C | | Boiling point | 72 °C(lit.) | | density | 0.749 g/mL at 25 °C(lit.) | | vapor pressure | 232.8 mm Hg ( 37.7 °C) | | refractive index | n20/D 1.409(lit.) | | Fp | −11 °F | | storage temp. | Store below +30°C. | | solubility | In methanol, g/L: 380 at 5 °C, 415 at 10 °C, 500 at 15 °C, 595 at 20 °C, 740 at 25 °C, 1,100 at 30
°C. Miscible at higher temperatures (Kiser et al., 1961). | | form | Adhering Crystals | | color | White | | Odor | Like gasoline. | | Odor Threshold | 1.7ppm | | explosive limit | 8.35% | | Water Solubility | 41.8mg/L(25 ºC) | | BRN | 1900214 | | Henry's Law Constant | 0.362 atm?m3/mol at 25 °C (Hine and Mookerjee, 1975) | | LogP | 3.37 at 20℃ | | CAS DataBase Reference | 96-37-7(CAS DataBase Reference) | | EPA Substance Registry System | Methylcyclopentane (96-37-7) |
| | Methylcyclopentane Usage And Synthesis |
| Chemical Properties | Methylcyclopentane is a colorless, flammable liquid with a sweet gasoline-like odor. An odor threshold concentration of 1.7 ppmv was reported by Nagata and Takeuchi (1990). Soluble in ether, miscible with alcohol and benzene, insoluble in water. | | Uses | Methylcyclopentane is used as an extractive solvent, an azeotropic distillation agent, and in organic synthesis. [Hawley] | | Uses | Methylcyclopentane can undergo ring opening or ring enlargement to yield various hydrocarbons including branched and unbranched hexanes, cyclohexane and benzene. | | Definition | ChEBI: Methylcyclopentane is a cycloalkane that is cyclopentane substituted by a single methyl group. It has a role as a human metabolite and a plant metabolite. It is a cycloalkane and a volatile organic compound. It derives from a hydride of a cyclopentane. | | Preparation | Methylcyclopentane mainly exists in industrial hexane, accounting for about 5%. However, because its boiling point is close to that of n-hexane (68.74°C), it is difficult to completely separate it by general rectification methods. Therefore, methylcyclopentane with a purity of more than 99% can be obtained by azeotropic distillation with methanol. | | General Description | Methylcyclopentane appears as a colorless liquid. Insoluble in water and less dense than water. Flash point near 20 °F. Very dangerous fire risk. Vapors may be narcotic and irritating. Used to make other chemicals. | | Air & Water Reactions | Highly flammable. Insoluble in water. | | Reactivity Profile | Methylcyclopentane can react vigorously with oxidizers. (NTP, 1992). | | Hazard | Flammable, dangerous fire and explosionrisk. May be irritant and narcotic. | | Health Hazard | Inhalation causes dizziness, nausea, and vomiting; concentrated vapor may cause unconsciousness and collapse. Liquid causes irritation of eyes and mild irritation of skin if allowed to remain. Ingestion causes irritation of stomach. Aspiration causes severe lung irritation, rapidly developing pulmonary edema, and central nervous system excitement followed by depression. | | Fire Hazard | Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. | | Safety Profile | Mildly toxic by
inhalation. Probably irritating and narcotic
in high concentration. Very dangerous fire
hazard when exposed to heat, flame, or
oxidizers. Can react vigorously with
oxidizing materials. To fight fire, use foam,
CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. | | Synthesis | Methylcyclopentane, occurs in various petroleums.It is readily formed by the isomerization of cyclohexane with aluminum chloride.Hydrogen and Ni at 460℃ also convert cyclohexane to methylcyclopentane. It is more readily oxidized than cyclopentane, presumably because of the tertiary H. Heating with dil. nitric acid replaces this H by a nitro group. | | Potential Exposure | This material is used as a solvent;
as a fuel; and in chemical synthesis. | | Source | A constituent in gasoline. Harley et al. (2000) analyzed the headspace vapors of three
grades of unleaded gasoline where ethanol was added to replace methyl tert-butyl ether. The
gasoline vapor concentrations of methylcyclopentane in the headspace were 2.7 wt % for regular
grade, 2.6 wt % for mid-grade, and 2.6 wt % for premium grade.
California Phase II reformulated gasoline contained methylcyclopentane at a concentration of
26.2 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without
catalytic converters were 4.32 and 604 mg/km, respectively (Schauer et al., 2002). | | Environmental fate | Photolytic. A photooxidation rate constant of 7.0 x 10-12 cm3/molecule?sec was reported for the
reaction of methylcyclopentane and OH radicals in the atmosphere (Atkinson, 1990).
Chemical/Physical. Complete combustion in air produces carbon dioxide and water vapor.
Methylcyclopentane will not hydrolyze because it does not contain a hydrolyzable functional
group.
At elevated temperatures, rupture of the ring occurs and 1-propene is produced in a 40% yield.
Other products include hydrogen and cyclic mono- and diolefins (Rice and Murphy, 1942). | | Solubility in water | In methanol, g/L: 380 at 5 °C, 415 at 10 °C, 500 at 15 °C, 595 at 20 °C, 740 at 25 °C, 1,100 at 30
°C. Miscible at higher temperatures (Kiser et al., 1961). | | Shipping | UN2298 Methyl cyclo pentane, Hazard Class: 3;
Labels: 3-Flammable liquid | | Purification Methods | Purification procedures include passage through columns of silica gel (prepared by heating in nitrogen to 350o prior to use) and activated basic alumina, distillation from sodium-potassium alloy, and azeotropic distillation with MeOH, followed by washing out the methanol with water, drying and distilling. It can be stored with CaH2 or sodium. [Vogel J Chem Soc 1331 1938, Beilstein 5 III 55, 5 IV 84.] | | Incompatibilities | Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. | | Waste Disposal | Dissolve or mix the
material with a combustible solvent and burn in a chemical
incinerator equipped with an afterburner and scrubber.
All federal, state, and local environmental regulations
must be observed. |
| | Methylcyclopentane Preparation Products And Raw materials |
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