4-methylcyclohexanemethanol
methanol_200.svg) |
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| Names | |
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IUPAC name
(4-Methylcyclohexyl)methanol
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Other names
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| Identifiers | |
| 34885-03-5 | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 105625 |
| ECHA InfoCard | 100.131.091 |
| PubChem | 118193 |
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| Properties | |
| C8H16O | |
| Molar mass | 128.22 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | mint-like, licorice-like (trans) |
| Density | 0.9074 g/cm3 |
| Boiling point | 202 °C (396 °F; 475 K) |
| low | |
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Refractive index (nD)
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1.4617 |
| Hazards | |
| R-phrases | R36/37/38 |
| S-phrases | S26, S36/37/39 |
| Flash point | 80 °C (176 °F; 353 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.
It is a colourless oil with a faint mint-like alcohol odor. The trans isomer has a particularly low odor threshold (~7 ppb in water) and a more licorice-like quality which is not associated with the less detectable cis isomer. Like other 8-carbon alcohols, such as 1-octanol, this compound is only slightly soluble in water but highly soluble in many organic solvents. The solubility of 1-octanol in water is 2.3 grams per liter.
It was first prepared in 1908 by Bouveault–Blanc reduction of a methylcyclohexanecarboxylate ester.
It is also produced as a byproduct (ca. 1%) in the production of cyclohexanedimethanol, a commodity chemical, during hydrogenation of dimethyl terephthalate.
It has been patented for use in air fresheners.
U.S. Patent 4915825 describes a froth flotation process for cleaning coal where a mixture of 95% MCHM, 4% water, and 0.1% 4-methylcyclohexanemethanol monoether (such as 4-(methoxymethyl)cyclohexanemethanol) is used as a frothing agent, and finely divided coal particles adhere to air bubbles induced into the agent which rise to the surface. Other cyclohexane-based alcohols can also be used. MCHM has the advantage of being less toxic than previous frothing agents containing 2-ethylhexanol. The original patent owners let the patent expire after eight years for failure to pay maintenance fees.
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