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Chemical compound From Wikipedia, the free encyclopedia
Methylcyclohexane (cyclohexylmethane) is an organic compound with the molecular formula is CH3C6H11. Classified as saturated hydrocarbon, it is a colourless liquid with a faint odor. Methylcyclohexane is used as a solvent. It is mainly converted in naphtha reformers to toluene.[4] Methylcyclohexane is also used in some correction fluids (such as White-Out) as a solvent.
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Names | |||
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Preferred IUPAC name
Methylcyclohexane | |||
Other names
Hexahydrotoluene Cyclohexylmethane Toluene hexahydride | |||
Identifiers | |||
3D model (JSmol) |
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ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.003.296 | ||
PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C7H14 | |||
Molar mass | 98.189 g·mol−1 | ||
Appearance | Colourless liquid | ||
Odor | faint, benzene-like[1] | ||
Density | 0.77 g/cm3 | ||
Melting point | −126.3 °C (−195.3 °F; 146.8 K) | ||
Boiling point | 101 °C (214 °F; 374 K) | ||
0.014 g/L at 25 °C[2] | |||
Vapor pressure | 37 mmHg (20°C)[1] 49.3 hPa at 20.0 °C | ||
-78.91·10−6 cm3/mol | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards |
severe fire hazard | ||
GHS labelling: | |||
Danger | |||
H225, H302, H304, H315, H336, H410[2] | |||
P210, P235, P301+P310, P331, P370+P378, P403[2] | |||
NFPA 704 (fire diamond) | |||
Flash point | −4 °C (25 °F; 269 K)[2] Closed cup | ||
283 °C (541 °F; 556 K)[2] | |||
Explosive limits | 1.2%-6.7%[1][2] | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
2250 mg/kg (mouse, oral)[3] | ||
LC50 (median concentration) |
10172 ppm (mouse, 2 hr) 10,000-12,500 ppm (mouse, 2 hr) 15227 ppm (rabbit, 1 hr)[3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 500 ppm (2000 mg/m3)[1] | ||
REL (Recommended) |
TWA 400 ppm (1600 mg/m3)[1] | ||
IDLH (Immediate danger) |
1200 ppm[1] | ||
Safety data sheet (SDS) | [2] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It can be also produced by hydrogenation of toluene:
Methylcyclohexane, as a component of a mixture, is usually dehydrogenated to toluene, which increases the octane rating of gasoline.[4]
It is also one of a host of substances in jet fuel surrogate blends, e.g., for Jet A fuel.[6][7]
Methylcyclohexane is used as an organic solvent, with properties similar to related saturated hydrocarbons such as heptane.[8] It is also a solvent in many types of correction fluids.
Methylcyclohexane is a monosubstituted cyclohexane because it has one branching via the attachment of one methyl group on one carbon of the cyclohexane ring. Like all cyclohexanes, it can interconvert rapidly between two chair conformers. The lowest energy form of this monosubstituted methylcyclohexane occurs when the methyl group occupies an equatorial rather than an axial position. This equilibrium is embodied in the concept of A value. In the axial position, the methyl group experiences steric crowding (steric strain) because of the presence of axial hydrogen atoms on the same side of the ring (known as the 1,3-diaxial interactions). There are two such interactions, with each pairwise methyl/hydrogen combination contributing approximately 7.61 kJ/mol of strain energy. The equatorial conformation experiences no such interaction, and so it is the energetically favored conformation.
Methylcyclohexane is flammable.
Furthermore, it is considered "very toxic to aquatic life".[9] Note, while methylcyclohexane is a substructure of 4-methylcyclohexanemethanol (MCHM), it is distinct in its physical, chemical, and biological (ecologic, metabolic, and toxicologic) properties.[10]
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