Talk:4-Methylcyclohexanemethanol

Carboxylic Acid
Do people think it requires a reference to say that 4-methylcyclohexanecarboxylic acid is the corresponding carboxylic acid to 4-methylcyclohexane methanol? I would normally be wary of putting even something that obvious in, but it seems like making the connection to the naphthenic acids is important, given how much research there is on them. I've put it in there for now, but I thought I'd solicit some feedback. Tarchon (talk) 03:47, 22 January 2014 (UTC)

Naval Laboratory
Where is the citation for the Naval lab stating 0.057 ppm is the acceptable level? — Preceding unsigned comment added by 173.81.120.38 (talk) 21:25, 16 January 2014 (UTC)

Not Chiral
There is an error in the first paragraph. This molecule is not chiral and has no chiral centers. It does have two diastereomeric forms -- cis and trans. — Preceding unsigned comment added by 76.167.63.65 (talk) 20:42, 11 January 2014 (UTC)

I would not regard it as an example of a compound which has two diastereomeric forms, I have looked and I can not see any chrial centres in the molecule. However it will have a cis and trans isomers.Dr Mark Foreman (talk) 06:31, 18 January 2014 (UTC)

I have made a drawing of the chair forms of the two isomers



Could someone please help me by adding the picture to the article, I do not know quite how to do it.Dr Mark Foreman (talk) 08:26, 18 January 2014 (UTC)

Solubility in water = "low"? This concerns me.
I have not waded through all the INFOBOX references, so I haven't yet figured out yet where the reference to "low" solubility comes from or what "low solubility" actually means. The Material Safety Data Sheets (MSDSs) I've seen so far state "Unavailable" for water solubility (this is usually found in the Physical Properties section of the MSDS, usually Section_9, sometimes Section_3 or on rare occasion elsewhere).

Water solubility will provide an idea of just how quickly this compound disperses and transports in surface and underground flowing water. [And relatedly, it would also be good to see if there exist any partition coefficient data for this compound, which is always worth a look when determining how to remediate contaminated water and/or soil. If I find anything I'll be back.]

While I doubt this stuff is nearly as water-soluble and environmentally dispersible as the infamous MTBE, it is an oxygenated aliphatic compound (like MTBE). Such oxygenation can increase water solubility considerably relative to a compound's non-oxygenated aliphatic analog. Since a lot more folks are going to be visiting this page while the West Virginia chemical spill is in the news, I am concerned that they not be misled by non-quantified and undefined statements regarding compound properties that are very critical where environmental contamination is concerned.

Unless and until specific water solubility data becomes available, I would urge that "low" be replaced by "unavailable" or "unknown" (or similar) for the Solubility in Water listing in the Infobox. Sharl928 (talk) 21:12, 11 January 2014 (UTC)Sharl928
 * Good point, but for readers less knowledgeable than you, low seems better than unavailable. Its an octanol, which has been studied throughly, and can reasonably be expected to have comparable solubility. --Smokefoot (talk) 21:17, 11 January 2014 (UTC)
 * As I suspect others have noted, the 93rd edition of the CRC Handbook p. 3-366, available via Google Books (My own 54th edition fails to include the compound) lists no solubility information:
 * No.: 7148
 * Name: 4, Methylcyclohexanemethanol
 * Synonym: [n/a]
 * Mol. Form.: C8H16O
 * CAS-RN: 34885-03-5 [Chemical Abstracts Service Registry Number]
 * MolWt: 128.212
 * Physical Form: [n/a]
 * mp degC: [n/a]
 * bp degC: 75[superscript:]?? [where "??" looks like "25" or "2.5"]
 * den g*cm^-3: 0.9074(note ??)
 * n(D): 1.4617(note ??) [refractive index; Na line D illuminant]
 * Solubility: [n/a]
 * Anonymous Solon 178.67.35.229 ("Lazy to look for it...") or some other person has apparently substituted a bp of 202 degrees C for the 75 degrees C listed in the 93rd CRCH. Perhaps the cited article on the subject of a related but (I presume) different compound, Dihydro-p-tolualdehyde, contains a more authoritative value. It's hidden behind a paywall and the five pages can't be viewed for less than USD30. All other characteristics listed in the CRCH agree with the current infobox, as may be seen. Rt3368 (talk) 12:37, 16 January 2014 (UTC)


 * I kind of agree with him. "note 15" is probably important because that BP probably isn't 75 C at STP. hexahydro-p-tolualdehyde is the aldehyde analog of MCHM, but not sure how dihydro relates. Back in the day, they used to like to name alicyclics as hydrogenated aromatics. MCHM could be called hexahydro-p-tolyl carbinol but it didn't seem like a synonym worth adding. Under that name the BP is given as 197 deg. (presumably C) http://books.google.com/books?id=LNEfAQAAMAAJ&lpg=PA108&ots=t8sGJgo03m&dq=hexahydro%20tolyl%20alcohol&pg=PA108#v=onepage&q=hexahydro%20tolyl%20alcohol&f=falseTarchon (talk) 08:49, 20 January 2014 (UTC)


 * I fear I may have misrepresented the 93rd edition. When I wrote "75(note 15)" above, I should have written "75([superscript:]??" where "??" looks like "25" or "2.5" in GBooks' representation. When I looked at this entry on p. 3-366 before, it looked like "15". Also, on "Explanation of Table" p. 3-2, I read
 * "The data in the table have many sources, including both the primary literature and evaluated compilations. The Handbook of Data on Organic Compounds, Third edition (Ref. 7) and the Combined Chemical Dictionary (Ref. 8) were important sources. Other useful sources of physical property data on organic compounds are listed in Refs. 9-19.  The values in the table for the normal boiling point and the melting point that are accompanied with uncertainties (in parenthesis) have been critically evaluated using the NIST ThermoData Engine (TDE, Ref. 20), designed to implement the dynamic data evaluation concept (Refs. 21-24).  This concept requires large electronic databases capable of storing essentially all relevant data known to date with detailed descriptions of metadata and uncertainties.  The combination of these electronic databases with expert-system software, designed to automatically generate recommended property values based on available experimental and predicted data, leads to the ability to produce critically evaluated data dynamically, 'to order.' The uncertainties listed are combined expanded uncertainties (level of confidence, approximately 95 %) representing the most comprehensive measure of the overall data reliability (Refs. 25-28)."
 * So this suggests that some temperature values in the table are automatically derived but as I say, the "25" or "2.5" is a raised, reduced-sized font, not parenthesized. So the superscript may well refer to alternate sample pressure - I can't find whatever it references. I apologize if this dwells on this source too much; I think the consensus here that the bp is significantly higher than 75'C is dispositive. Rt3368 (talk) 06:47, 30 January 2014 (UTC)

If it is not very water soluble and it is lighter than water would it not be safe to infer that it would not likely enter the potable water system as their inlets are well below the surface? Additionally, the closely related chemicals have very low toxicity in mice so... Finally, why not just boil the tap water or use activated charcoal (Brita, etc.) filters? — Preceding unsigned comment added by 180.94.74.46 (talk) 08:56, 13 January 2014 (UTC)
 * Indeed. Jeff McIntyre, president of West Virginia American Water Company has been quoted saying
 * "I wish I could speak to that with some authority. This is a highly soluble compound . . . The information I have is, 'I don't believe.' It's an opinion, and it's the best I can offer." (emphasis added)
 * So, this means absolutely nothing. Rt3368 (talk) 12:37, 16 January 2014 (UTC)
 * The boiling point above is almost certainly for reduced pressure, not 1 atm. The value in this article looks fine.  This compound is an octanol, isomers of which are expected to have very similar boiling points.  Solubility of n-octanol in water is 2.3 g/L.  Even if the solubility varies by a factor of 2, it reveals that water can readily wash our MCHM from a water system. --Smokefoot (talk) 14:00, 16 January 2014 (UTC)

I would agree that it's highly soluble in, say, ethanol, but in water, no way. Neither cyclohexanemethanol (http://www.chemicaldictionary.org/dic/C/Cyclohexanemethanol_1171.html) nor dimethylcyclohexanemethanol is especially water soluble, so the likelihood that MCMH would be seems rather small. "Slightly soluble in water" seems believable. While it is oxygenated, it's carrying around a pretty big non-polar rear end. Data sheets differ on whether CHM is insoluble in water or "slightly soluble" and it's not going to get any more water soluble with a methyl group. Tarchon (talk) 07:11, 20 January 2014 (UTC)

2-ethyl hexanol (which is close to MCHM in mass and branching but without the ring closure) at 68 F has a solubility of 0.07 lbs per 100 lbs of water (http://cameochemicals.noaa.gov/chris/EHX.pdf), which comes out to about 3 g/l, pretty close to the 1-octanol value, so it's pretty likely to be in the range of a few to several g per liter. That falls squarely in "slightly soluble" by Sigma Aldrich's definition. Thus I would say that we have no reason to doubt a claim for "slightly soluble". Tarchon (talk) 18:30, 21 January 2014 (UTC)

Errors
Other errors included in the Health and Safety section which references [4] on the reference list. The toxicology data network product referenced is for METHYLCYCLOHEXANOL which has a completely different CAS#...it's not the same chemical. misinformation here! For a correct SDS on this chemical go to: http://mediad.publicbroadcasting.net/p/wvpn/files/201401/MSDS-MCHM_I140109214955.pdf 64.135.237.40 (talk) 22:09, 11 January 2014 (UTC)64.135.237.40 (talk) 22:14, 11 January 2014 (UTC)
 * The compound can be assigned a variety of names. I'm afraid the MSDS you've linked to is for a mixture of 7 different chemicals and is 8 years old. Not exactly definitive data. Project Osprey (talk) 01:41, 12 January 2014 (UTC)

....Yep, that MSDS certainly does not cover the high-purity compound - here is a link (.pdf, 3pp) to TCI America's MSDS for >98% purity compound - but I'll wager that link supplied above to Eastman Chemical's MSDS comes a lot closer to what was actually used to wash that coal. High-purity chemicals usually come with a high price tag, affordable (in small quantities) for research laboratories or high-value product manufacturing (e.g., pharmaceuticals, microelectronics) - where the cost can be passed on to the customer. No company like (heh) Freedom Industries - even if on its best behavior - is going to pay for high-purity chemicals for large scale cleaning of low-cost solid-phase commodity fuels, at least not if it wants to stay in business. --Sharl928 (talk) 03:56, 12 January 2014 (UTC)Sharl928
 * Adding to the previous, current news reports - see references in the Wikipedia entry for the 2014 Elk River chemical spill - are now quoting sources that it was "crude MCHM" that was released. Those same news sources also note that compositional details on this material are not currently available to the public, beyond the presumption that the material is mostly 4-methylcyclohexanemethanol (MCHM), but also containing a number of other so far unidentified chemical compounds. --Sharl928 (talk) 08:14, 12 January 2014 (UTC)Sharl928

If the structure shown is correct, the molecular weight is correct but the composition should be C8H16O and not C8H14O2. — Preceding unsigned comment added by 71.185.39.250 (talk) 16:50, 12 January 2014 (UTC)

Boiling point
Lazy to look for it and don't know how to edit but 75'C is impossible for such compound. 178.67.35.229 (talk) 08:54, 12 January 2014 (UTC)

MSDS
here is a link to the actual MSDS for this chemical http://mediad.publicbroadcasting.net/p/wvpn/files/201401/MSDS-MCHM_I140109214955.pdf 64.135.237.40 (talk) 14:57, 12 January 2014 (UTC)

5,000 or 7500 gallons
i thought 7500 gallons are now thought to have spilled. — Preceding unsigned comment added by Patbahn (talk • contribs) 17:54, 12 January 2014 (UTC)

More detail on use in cleaning coal
From a source interviewed for a National Geographic news report on the 2014 Elk River chemical spill - described as a consultant at a major mining industry firm (and who requested anonymity for the interview) - it is estimated that crude MCHM is used in about 20-25% of coal processing plants in West Virginia, where it is destined to become the "coking coal" used for metallurgical production. [This kind of coal is not used as fuel for electrical plants. That is "steam coal", which is said in that article to be the primary use for coal.] The consultant said that crude MCHM took the place of "diesel" (presumably diesel fuel) as a froth flotation cleaning agent some years ago, since diesel posed problems in complying with air emission regulations. --Sharl928 (talk) 21:52, 12 January 2014 (UTC)Sharl928
 * Minor tweaks made to entry above - internal link to 'diesel fuel' added, quote marks removed from cleaning (deemed not necessary, and might have been construed as sarcastic, which was not the intent). --Sharl928 (talk) 03:12, 13 January 2014 (UTC)Sharl928