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Sat Jan 11, 2014, 07:58 PM


(I love the fact that this thing is not really water soluble, they don't know (or care) what prolonged exposure does, and they are making air fresheners and soap with it)

Molar mass 128.21 g mol−1
Appearance Colourless oil
Density 0.884 g/cm3
Boiling point 192 C; 378 F; 465 K
Solubility in water low

4-Methylcyclohexanemethanol, or more appropriately 4-methylcyclohexylmethanol, is an organic compound with the formula CH3C6H10CH2OH. Classified as an alcohol, it exists as two isomers with similar properties. It is a colourless oil with a faint mint-like odor of licorice. Like other octanols,
********THE COMPOUND IS ONLY SLIGHTLY SOLUBLE IN WATERr****** but highly soluble in many organic solvents.

Synthesis and production

It was first prepared by Bouveault-Blanc reduction of the corresponding methylcyclohexanecarboxylate ester.

It is produced as a byproduct (ca. 1%) from the production of cyclohexanedimethanol, which is obtained by hydrogenation of dimethylterephthalate, a commodity chemical.

C6H4(CO2CH3)2 + 8 H2 → CH3C6H10CH2OH + 2 CH3OH + 3 H2O


MCHM has been produced and used as "a solvent for cellulose esters and cellulose ethers and for lacquers resins, oils, and waxes, an antioxidant for lubricants, and a blending agent for special textile soaps." ********It has been patented as an air freshener.*******

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 monoesters, monoaldehydes, and cyclohexane alcohols can also be used. MCHM has the advantage of being less toxic than previous frothing agents containing 2-ethylhexanol. However, its owners let the patent expire after 8 years for failure to pay maintenance fees.
Health and safety

Routes of exposure to MCHM include inhalation, dermal contact, and ingestion. According to the Hazardous Substances Data Bank of the U.S. National Library of Medicine Toxicology Data Network (Toxnet), exposure to MCHM vapors, particularly prolonged exposure and exposure at excessive concentrations, can produce irritation to eyes, skin, upper respiratory tract, and mucous membranes; skin rash, and headache. "High exposures from skin contact or inhalation may cause damage to the heart, liver, kidneys, and lungs, and may result in death."

It has been reported that it can be dangerous in high concentrations. In lower concentrations it can cause irritation to the skin, eyes, and throat, as well as drowsiness, breathing problems, and dizziness. Swallowed it can cause nausea. If breathed into lungs it may cause pneumonia.

Prolonged exposure effects are not clear

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Arrow 9 replies Author Time Post
Reply 4-Methylcyclohexanemethanol (Original post)
niyad Jan 2014 OP
grantcart Jan 2014 #1
niyad Jan 2014 #2
grantcart Jan 2014 #3
niyad Jan 2014 #4
Cirque du So-What Jan 2014 #5
reACTIONary Jan 2014 #6
chemhavsoln Jan 2014 #7
Katashi_itto Jan 2014 #8
niyad Jan 2014 #9

Response to niyad (Original post)

Sat Jan 11, 2014, 08:13 PM

1. Is this going to be on the mid-term?

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Response to grantcart (Reply #3)

Sat Jan 11, 2014, 08:21 PM

4. it will be open book

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Response to grantcart (Reply #1)

Sat Jan 11, 2014, 09:04 PM

5. My mid-terms are long behind me

and, although I took two semesters of organic chemistry back in the day, now I don't know my azo- from a haloethane in the ground.

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Response to niyad (Original post)

Thu Jan 16, 2014, 11:36 PM

7. umm, minor point

Very good general info,(too bad the news doesn't tell enough re soaps and air fresheners)
But the chem synthesis is not correct, the reduction on the diester only makes 1 mole of water, not 3.

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Response to Katashi_itto (Reply #8)

Fri Jan 17, 2014, 12:21 AM

9. the chemical that leaked into the elk river in west virginia that left over 300,000 without water.

the plant that had not been inspected since 1991.

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