The 4-methylcyclohexane methanol spill in West Virginia (Coal cleaning chemical)

4-methylcyclohexane methanol is a chemical used to clean coal before it is burned. As you know a region of southern West Virginia where upwards of 100,000 people live has been affected by a spill of this chemical; the water supply in this area has been made unavailable for human use. A 48,000 gallon storage tank for 4-methylcyclohexane methanol has been leaking the chemical into the Elk River, which is part of the municipal water supply in the area.

Apparently there isn’t a lot known about this particular chemical. It’s chemical name is scary looking, and resembles the names of other better known chemicals that are really toxic. But it is also a form of alcohol. How bad can that be?

I wonder if the various chemistry experts out there could comment on this chemical.

Given the nature of the molecule, is it likely to be toxic? To bio-accumulate? To evaporate over time, or not? Even though there is apparently no way to clean the water of this chemical in place would that be something that could be easily implemented?

Is this region of West Virginia now uninhabitable for the next few decades or is this chemical going to degrade and/or disperse to a harmless level in a few weeks?

Any ideas?

Sources of information:



Debora Blum


Salon: Little is known

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64 thoughts on “The 4-methylcyclohexane methanol spill in West Virginia (Coal cleaning chemical)

  1. Herbal infusion bagger, that’s not the same compound. I know, I know, Wikipedia got it wrong, too, and so did the media. Probably not much to worry about the actual compound either (couldn’t find its MSDS that easily, oddly), but still.

  2. News reports (CBS network radio) say it’s a “skin irritant.” From that we can safely guess it’s also a gastrointestinal irritant and a nasty eye irritant. There are other chemicals that were once thought of primarily as irritants in public health terms, but were subsequently found to be carcinogens, so although reasoning-by-analogy is bad methodology (frequently used by overt quacks, see also Orac’s blog), this is one of those cases where erring on the side of caution has no downside.

    If this had been a nuclear plant accident, the media would turn it into a super-duper spectacle complete with a hefty helping of cry-porn. As it is, coal burning “only” kills in the range of 20,000 – 24,000 people per year in the USA (respiratory illnesses downwind of coal plants) and helps destroy the biosphere.

    Realistically, everyone can benefit from keeping a supply of what we in California call “earthquake water.” Every region of the country is subject to some type of risk to water supply, so it’s prudent no matter where you are. Two gallons per person per day = the absolute minimum for drinking, cooking, and hand washing. Better, five gallons per person per day so you can take a sponge bath every couple of days. Search online for details about safe water storage.

  3. Sorry it has taken me a while, I have been busy with work stuff.

    This stuff is used as a reagent for froth flotation of coal. Coal is hydrophobic, many of the minerals in coal (clay, shale) are hydrophilic. When you bubble air through a mixture of particles with different degrees of hydrophilic/hydrophobic balance, the hydrophobic particles tend to stick to the air bubbles (because that minimizes the energy of the bubble film. This is the same reason that soap helps to remove dirt. Soap is a salt of a carboxylic acid, it has a polar tail that attaches to water and a non-polar tail that attaches to things hydrophobic (like coal, oil or greasy dirt).

    As far as this specific compound goes, at high levels anything is toxic. There was so much of it that it was floating on top of the river. It is soluble in water, about what you would expect for an 8-carbon alcohol. It is all unsaturated (which makes it less toxic), but it does have a ring (which makes it more toxic).

    It probably will degrade, but it is now winter, so any degradation will be slow, and will need:
    1. The right bacteria, this is not something that all bacteria could metabolize.
    2. Other nutrients: nitrogen, phosphorous, iron, and trace minerals
    3. Oxygen (this is probably the most important)
    4. Surfaces for bacteria to live on

    There are reports that it is rapidly metabolized by adapted sewage sludge. Sewage sludge does have all of the things that bacteria need, other nutrients, oxygen and surface. Those things are not available in a river.

    The stuff is pretty soluble, and the MSDS says that it is not expected to adhere to sediments, which I concur with. It floats, so it won’t seep down into the ground and down into immovable deposits the way that PCBs did in the Hudson river.

    It will likely kill any animal or vegetable life it comes in contact with. Once it is diluted enough bacteria will metabolize it. It is winter now, so that will greatly delay biodegradation. The cold likely reduces toxicity some (but also reduces ability of organisms to respond to toxicity effects). You also can’t tell if plants have been killed until spring.

    There likely won’t be long term effects, other than the bankruptcy of the company that did this and any associated suppliers or users that can be tagged with liability (and I hope better regulations and better enforcement). The damages are in the billions already.

    It is likely that this is a result of negligence, which means officers and directors may be liable (criminally and civilly) too for improper supervision and insufficient funding of necessary procedures.

    There won’t be enough money to compensate everyone, just like the Texas explosion. This is what a no-regulation mindset produces; owners of businesses gambling with the public’s health and safety. If nothing happens they are happy to privatize the savings, if something does happen they expect the government to bail everyone out.

  4. If all you have is a material safety data sheet to guide your research into the proper use of this chemical, the toxicity of this chemical long term, or issues that could arise from its improper use, God help us all.
    The only good arising from an MSDS sheet is to give regulators and Inspectors a warm fuzzy feeling. I can’t imagine a bunch of guys at the water treatment plant looking to an MSDS sheet for guidance. I’d be VERY impressed if they even could find one, let alone a specific one. You would find out more about this stuff with a dixie cup, a q tip, and a match.

  5. My brief research shows that 4-methylcyclohexane is also 1,2,3,6-Tratrahydrotoluene and both are “little known or studied.” How is it that West Virginia would permit a “little known or studied” chemical to be stored in tanks that could leak into the water supply of its citizens? How can we explain such negligence?

  6. “Herbal infusion bagger, that’s not the same compound.”

    Note that info methylcyclohexanol is a mixture of the 2,3, and 4 isomers. Also, each of those in turn will have cis-, trans- isomers. If there was a really nasty isomer in there, it would drive the toxicity results for the mixture. The physiochemistry (volatility, bioaccumulation) aren’t going to vary much by isomer – the alcohol group is driving much of the physical properties.

    Note that as it will be relatively water-soluble, it will probably blow through carbon filters pretty quickly.

    This Eastman MSDS has more tox information than the other:

    2,000 mg/kg/day is a pretty high LD50.

    “It probably will degrade, but it is now winter, so any degradation will be slow, and will need:
    The right bacteria, this is not something that all bacteria could metabolize.”

    Beg to differ – there was a big change in how we treated hydrocarbon fuel tank spills in the 1990s because of the realization of how ubiquitous hydrocarbon-degrading bacteria were. There’s not a weird ether bond or suchlike to retract degradation. However, volatization is going to be the major fate for this compound rather than degradation – it’s Henry’s law constant (or at least that for the 2,3,4-isomer mixture) is pretty high. And 7,500 gallon is a relatively small spill.

  7. Here we have another sensationalized news story and people over re-acting before they truly understand anything. We put more dangerous chemicals into our bodies everyday and yet no one reacts like this. Look at what marijuana does to the brain and yet how many pot heads are going to claim that this company has somehow harmed them. I would like to see the true water test results from the average home tap. The before and after dates of course. Our food supply has many chemicals in it that are really bad for us and no one is complaining. Ethanol is a poison to the human body and yet how many continue to swallow the stuff each day. Same stuff that goes in your gas tank goes into your body and we are going to complain about a small chemical spill. What are water filters for? I have have several and they work great. This spill like others will be used to destroy jobs and continue the downfall of the country. Really a sad time for America due to ignorance and laziness.

  8. Storing mammoth amounts of chemicals just upstream of water intake for 300,000 people has to be a crime, even if it was legal.

  9. I had another thought about this situation. With all of the mountain spring water in the region, Why are they using a river or a lake for drinking water? Those folks around mount. Fuji use spring water even though there are lakes in the region. Water companies should also be prepared and spend some of their huge profits to have emergency filters in place. This is America, Isn’t it? We have lost our edge and have become foolish. Our Nation used to be ahead of the game some years ago. And yes the Company should have been inspecting the tank more often, This is just my point. We used to be industrious and now for some reason have become the laughing stock of the world. and yet nobody seems to truly care. We do not need a ton of regulations to go forward, we just need Common Sense. Does anyone know what has happened to COMMON SENSE. It seems to be an endangered species these days. I often wonder why I gave the years of my life to serve a Nation that wants to become the Communist states of America. I am sure everyone affected will want a ton of money claiming how psychologically this has damaged them as well as all of the claims of physical problems that will somehow be blamed on the chemical spill. It is really easy to boil water before you drink it. I have done before and it works great. We have become a MOB in this country in which the media helps fan the flames. Just like our modern day election system.

  10. @Herbal Infusion Bagger

    “Note that info methylcyclohexanol is a mixture of the 2,3, and 4 isomers”

    But none of those isomers are the chemical that was spilled. Methylcyclohexanol is not methylcyclohexane methanol. There’s a difference of a carbon and two hydrogens.


    “My brief research shows that 4-methylcyclohexane is also 1,2,3,6-Tratrahydrotoluene”

    I think you meant 1,2,3,6-tetrahydrotoluene, but that is not the compound that spilled.

    1,2,3,6-tetrahydrotoluene is also known as 4-methylcyclohexene, but it is not the same as 4-methylcyclohexane methanol.


    I hate to discourage people from sleuthing, but it’s important that you get the chemical right first. Methylcyclohexanol and 4-methylcyclohexane methanol may only differ by a carbon and two hydrogens, but that’s all that separates water from methanol.

  11. I’ll also note that I think Deborah Blum’s (quoted in the Mother Jones article that Greg Laden linked to) may be incorrectly assuming that it’s a mixture of methylcyclohexane and methanol. At least, that’s what her comments suggest to me.

  12. @Michael Koronka

    Boiling water doesn’t remove chemicals, it would be useless in this case. Filters also aren’t magical. Of course the area treats its water, but we don’t live in a magical world where an “emergency filter” is available that can remove any unanticipated toxin.

  13. And…what about all the animal life that must live in the Elk River and downstream from heron/ospreys to fish to otters to beavers to the entire food chain starting with insect larva? What will be the short and long-term affect of this complex chemical on these populations? We can expect the fish, at least, to enter the human food chain at some point between the spill and the Gulf of Mexico.

  14. re the confusions above(#2 for example) is it too much to ask to use the IUPAC name ((4-methylcyclohexYL)methanol)?

    after all systematic names are there to get rid of ambiguity….

  15. Michael @18: There are several reasons why Charleston might not source their water from mountain springs:

    1. Not all mountain springs produce drinkable water. Some have naturally occurring compounds which make the water undrinkable (the existence of a town called White Sulphur Springs implies this is true of at least some springs in WV). Others may have become contaminated because of the operations of Big Coal, which is dominant non-government employer in the region.

    2. Charleston is in a river valley, so there may not be mountain springs close enough at hand.

    3. Charleston is a sizable city by WV standards (e.g., it’s the state capital), so one or a few springs would probably not be enough. You’d need a river source for a population that large. Also, being far enough downstream of contamination sources reduces their effect. Admittedly, letting a chemical company build a plant just upriver of your water intake is almost certainly a Bad Idea.

    As for filters: Of course they have them (all municipal water systems are supposed to). Filters are useful for getting rid of sediment, suspended particles, and some inorganic compounds. They do not help when you are dealing with a water-soluble organic compound, as in this case, unless they are specifically designed for the compound in question (unlikely to be true with a compound as obscure as this one was).

  16. West Virginia is coal country, and ground water in coal country tends to have higher levels of phenolic compounds like resorcinol.

  17. “But none of those isomers are the chemical that was spilled. Methylcyclohexanol is not methylcyclohexane methanol.”

    Ah crap. What you get for reading too fast.

    I’ve found (estimated) property data here:

    Henry’s law is 4-8 x 10^-6 atm-m3/mole, so still should volatilize pretty readily – it’s about the same range as ethanol.

    Octanol-water partition coefficient is modest (Kow = 2.55), so only slight bioaccumulation potential.

  18. “Water companies should also be prepared and spend some of their huge profits to have emergency filters in place.”

    A filtration plant for a modest-sized city can easily run into the a few billion dollars, and hence you don’t add unit operations to that plant just for the hell of it. Also, this isn’t a compound that easily is removed by filters – it’s too soluble in water. Air stripping would be the way to get rid of it.

    “As for filters: Of course they have them (all municipal water systems are supposed to). ”

    No. You have to disinfect water if you’re serving more than 25 households, but you don’t have to filter if it’s not needed to meet drinking water standards. But most sand filters will take out particulates and some colloidal material, not water-soluble contaminants.

  19. “Storing mammoth amounts of chemicals just upstream of water intake for 300,000 people has to be a crime, even if it was legal.”

    It’s not mammoth amounts of chemicals. This is a 40-ton spill from a 160 ton tank. A typical chemical plant might process dozens of kilotonnes of chemicals a year, with an inventory of a couple of thousand tonnes of chemicals onsite. And most chemical plants are close to waterways because need for access to cooling water.

    This was a mom-and-pop operation.

  20. It is really funny that so many people who do not know the difference between a lump of coal and a hornet nest are commenting on chemicals they can not even spell correctly.
    Please have the facts in front of you before commenting. If you do not have the facts, get them first, then comment. This whole thing is the result of incompetence by people in the water company and also the chemical company, but trying to talk it resolved by ignorance will not solve anything.

  21. The previous comment by DDBR is not an officially approved comment about commenting. Feel free to comment jibberish.

    But yes, the point of this post was to get information out there on the table, and there is some. The fact that some may be muddled simply proves the point: Expertise is needed.

  22. Greg: “Feel free to comment jibberish.”

    That sounds like my cue.

    Anyone know (or know how to find out) how many chemical storage facilities sit overlooking streams or other drinking water sources in WV, or in the state or locality of interest to them?

  23. Have you been to West Virginia?

    I’ve not in a long time, but chemicalish industrial facilities are all over the place there. And, there is not one square foot in the state that is not overlooking a stream or river.

  24. Greg,

    I have visited a few times; it’s a beautiful state.

    I was hoping to tap the collective consciousness to get a sense of the scope of potential similar ‘events’, coming soon to an aquafer near you (me, all of us).

  25. “I was hoping to tap the collective consciousness to get a sense of the scope of potential similar ‘events’, coming soon to an aquafer near you (me, all of us).”

    To be honest, this feels like a throwback event – this is the kind of spill you’d see back in the 1970s, back in the days when HP or Fairchild would dig up their underground tanks and find them riddled with holes.

    I’d thought regulatory requirements for secondary containment – berms, double-walled tanks, double-walled pipes – had made spills like this if not a thing of the past, at least pretty infrequent . We’ll have to wait until the incident investigation to find what regulations the owners wiped their ass with and what safety systems got overridden. Or whether they were exempt (because of small volumes) from standards for secondary containment.

    But, while this trashed the water supply of a large number of people temporarily, 40 tons is not that much inventory of chemicals – it could have been much worse. If this had been a chlorinated DNAPL (dense non-aqueous phase liquid), you’d be looking at dredging the stream bed to get rid of the gross contamination and months to years of remediation.

  26. H.I.B,

    “We’ll have to wait until the incident investigation to find what regulations the owners wiped their ass with and what safety systems got overridden. Or whether they were exempt (because of small volumes) from standards for secondary containment.”

    The good folks at MSNBC reported yesterday that chemical storage facilities are not subject to inspections *at all* in WV, only chemical production facilities. If that’s accurate, then no amount of regulatory requirements are worth the paper their written on, since no one will be inspected until after the leak is discovered.

  27. Question about filters, understanding that this chemical is water soluble and may blow through carbon filters, what about reverse osmosis systems? Will the membrane remove this chemical adequately?

  28. “:To be honest, this feels like a throwback event – this is the kind of spill you’d see back in the 1970s, ”

    Have you ever been to West Virginia? 🙂

  29. I am a victim of the WV chemical spill and after reading some of the comments I will simply say this… Come to WV and live it before you speak. Try living with no useable water, not being able to take a hot shower, having to use bottled water for EVERYTHING, and living with the uncertainty that you will ever have CLEAN water again. Lastly, we need HELP, not speculation.

  30. Mike – RO filtering can remove pretty much everything, including dissolved minerals. However, I’ve no idea what this stuff will do to an RO filtration system… For all I know, it might dissolve the membrane.

  31. I’m less confident than others that efforts to filter contaminants, or prevent them from entering the water supply in first place, are as effective as they need to be.

    Some findings from a study by the Environmental Working Group (EWG):

    “EWG assembled an unprecedented database of 20 million drinking water quality tests performed by water utilities since 2004. It reveals a total of 316 contaminants in water supplied to 256 million Americans in 48,000 communities in 45 states. Among the contaminants were 202 chemicals that are not subject to any government regulation or safety standards for drinking water. The U.S. Environmental Protection Agency (EPA) has set enforceable drinking water safety standards for only 114 of the 316 substances detected (EPA 2009b)…

    EWG obtained tap water testing data from state water offices, which had collected the results from the utilities in order to enforce state and federal water quality standards. EPA does not maintain its own comprehensive national drinking water quality database. The agency sets safety standards for contaminants based on limited test data gathered from select, representative states and water suppliers. EWG was unable to obtain water test results in electronic form from five states and the District of Columbia. EWG will provide its database upon request to the EPA and state authorities.
    The water contamination revealed by EWG’s database underestimates the scope of the problem. For 37 percent (17,840) of the 47,677 water systems analyzed by EWG, states’ databases contained no records of testing for any unregulated contaminants. EPA’s own limited surveillance programs have required testing for just a fraction of the hundreds of unregulated drinking water pollutants identified in peer-reviewed studies.
    EPA has set maximum allowable levels in drinking water for 114 pollutants reported in EWG’s database. In addition, the government has issued health guidelines for 90 of the 202 unregulated contaminants to provide advice for utilities and consumers. Our analysis found that 87 regulated and 49 unregulated chemicals were detected at least once at levels above these voluntary guidelines. A total of 252 million Americans were supplied at one time or another with water containing contaminants at concentrations above the recommended safety guidelines…

    Since 1996, EPA has reviewed data on toxicity and water pollution for 138 chemicals, but in every case it declined to set a safety standard. EWG’s database analysis showed that collectively these chemicals pollute drinking water for more than 111 million Americans.”

    As the commenter from Charleston WV, who is going without tap water for an indefinite period, so poignantly expressed, this is not some intellectual exercise, people are suffering.

    When it comes to water pollution, like air pollution, my impression is that is a fair degree of overconfidence in the technology, processes and standards used to limit contamination.

    Here is the technical data from the CDC’s most recent survey of chemicals found in blood an urine samples for the US population:

    It is 700 pages, and incredibly detailed (best read by or with the assistance of a chemist, biochemist or biologist), with scrupulous citations.

    The spill in WV is one event– horrendous for the people living through it– but in some sense it represents simply an isolated example of what is the rule, not the exception.

  32. Here’s the link to the CDC’s full report on chemical exposures, inadvertently omitted in the previous post:

    Much as I have doubts about current efforts to prevent and limit water contamination though technology (e.g., filtration), I think the assumption that bioremediation is effective at reducing toxicity (dilution, degradation of chemicals by bacteria and archaea, etc.) needs further scrutiny. It may be comforting to think ‘natural processes’ will remit the effects of chemical contaminants, and certainly anyone who earns a living in an industry where chemicals are used in large quantities will want to believe the ultimate effects of environmental exposure will be minimal.

    However, we need to not view the potential for bioremediation in idealized terms (i.e., the rate at which a specific quantity of one compound ‘should be’ degraded and/or diluted in a pristine environment). There are no pristine environments; estimates how long a contaminant will persist at a harmful level seem to be based on woefully inadequate models:

    The inherent biases in environmental research and their effects on public policy.
    Futures 34 (2002) 621–633
    Michael H. Huesemann
    Paci?c Northwest National Laboratory, Marine Science Laboratory, Sequim, WA 98382, USA

    “Bioremediation- the removal of contaminants via microbial degradation—emerged as one of the most preferred clean-up technologies, primarily because of its relative cost-effectiveness, and general public acceptance [23]. Despite these advantages, it was found that bioremediation had several serious limitations. First, it soon became evident that bioremediation could not meet some of the stringent cleanup criteria for soils that had been contaminated for long periods of time. In these aged soils, many of the strongly sorbed contaminants were found to be unavailable to degradative microorganism. It logically followed that, due to these bioavailability limitations, many aged soils cannot be treated successfully using cost-effective bioremediation. Instead, a more expensive treatment technology may be required to meet soil cleanup standards. Second, in the case of aquifers contaminated with soluble petroleum hydrocarbons such as carcinogenic benzene, it was found that active in situ bioremediation, i.e., the engineered addition of oxygen and nutrients to groundwater would be highly effective but grossly cost prohibitive in view of the several hundred thousand leaking underground storage tank sites in the US.” (pg. 625)

    Please note the last clause of the last sentence of that excerpt: “several hundred thousand leaking underground storage tank sites in the US”.

    I’m guessing there is a similar, if not greater, number, of above-ground storage sites in the US, and in equally suspect condition.

    Any suggestion that events like in WV are unusual, or that such spills pose little hazard in the aggregate, over the long-term, doesn’t pass the straight-face test. Big spills and slow seepage into aquifers are occurring essentially everywhere in the US (and pretty much the world), on a daily basis. The contaminants are accumulating much faster than any natural process can degrade them, and they are found in the blood of every man, woman and child walking the earth. I encourage folks to be less sanguine about this than many seem to be (pun sort of intended.)

    The questions I have for the more medically inclined biologists– are there synergistic and interaction effects from a stew of appx. 200 non-naturallt occurring compounds present in the cells of a living human (that is, are the harmful effects amplified by the combination, rather than considering them in isolation, since they are all present simultaneously in our body)?; does chronic exposure to the chemical stew impair our bodies ability to deal with the toxic effects of new exposures,? does chronic exposure to the chemical stew increase the likelihood that genetic function is altered/disrupted, even at levels considered ‘not harmful’?

    Any suggestion that those questions have been satisfactorily studied, and ‘all is well’, nothing to see here, move along, also wouldn’t pass the straight face test.

  33. “Question about filters, understanding that this chemical is water soluble and may blow through carbon filters, what about reverse osmosis systems? Will the membrane remove this chemical adequately?”

    Depends on the pore size of the RO filter and the material of the filter.. You’d have to get data specific to this compound, and as the struggle to get data in this thread shows, such data doesn’t exist.

  34. “In these aged soils, many of the strongly sorbed contaminants were found to be unavailable to degradative microorganism. It logically followed that, due to these bioavailability limitations, many aged soils cannot be treated successfully using cost-effective bioremediation.”

    Think about the logic in this passage (which doesn’t cite the source for the limits of bioremediation). If something’s too bound to the clay or humic fraction, to be bioavailable to microbes, *it’s not bioavailable to higher animals*. You might. One of the treatment options for soil contamination is immobilization. This is natural immobilization.

    It’s not relevant in this case, because of the solubility of the contaminant – it’s soluble, and it’s bioavailable.

  35. “I think the assumption that bioremediation is effective at reducing toxicity (dilution, degradation of chemicals by bacteria and archaea, etc.) needs further scrutiny.”

    The elemental composition of a compound and its structure make a difference to the ease of biodegradation. Chlorinated dioxins are a concern because they (1) bioaccummulate because they’re lipid-soluble, and (2) have chlorine-carbon bonds for which relatively few microbes have the enzymes to degrade (although there are some that can degrade chlorine-carbon bonds). Polyaromatic hydrocarbons have multiple aromatic rings, and have low solubility in water, so they persist and can bioaccumulate.

    This compound is an alcohol with moderate water solubility and no unusual bonds. There’s nothing in the structure that would indicate it would be recalitrant to biodegradation.

  36. Response to Dunc and Herbal on RO systems, I’ve spent the rest of the day looking into the question and have pretty much come up with the same conclusion. It’s fair to say that a good system should remove the compound, but with such limited information and no availability of specific testing on this compound and RO membranes it’s better to err on the side of caution and turn off the RO system in order to protect it. We are suggesting people turn off the supply to their home systems, when the water restrictions are lifted they should change their filters and sanitize the system, and flush the storage tank out several times. I would also dump any ice cubes out for several cycles if the RO system is connected to the ice maker. Just to be safe.

  37. I am very surprised that 4 methylcyclohexane has such a woefully inadequate MSDS profile when it is so widely used. According to what I just looked at, there is no toxicological data.It would appear to me that any company using this chemical would contract to conduct basic studies to protect themselves and others from accidental exposures like this West Virginia incident. That is blatently Iirresponsible.

  38. H.I.B.: “If something’s too bound to the clay or humic fraction, to be bioavailable to microbes, *it’s not bioavailable to higher animals*. You might. One of the treatment options for soil contamination is immobilization. This is natural immobilization.”

    Unless something were to disturb the soil, like, erosion, a bulldozer, drilling a well, or if leaching were to occur. Which is what actually happens. ‘Natural immobilzation’ involves the hope that the sediments lay undisturbed. This has not been borne out by the real world experience of, I dunno, every Superfund site ever identified. So, for example:

    “Chemicals with a combination of persistent, bioaccumulative, and toxic (PBT) properties are of particular concern because, once released to the environment, they can travel far from their source, remain in the environment for long periods of time, are toxic, and increase in concentration up the food chain. Some well-known PBT chemicals include dioxins and furans, lead, mercury, PCBs and hexachlorobenzene…
    Mixtures of chemicals can have different health and environmental effects from the effects of individual chemicals. Some mixtures can have effects that are greater than an individual chemical effect. In one study, a PCB compound (PCB153) given alone did not result in liver damage in rats, but when given with dioxin as a mixture produced 400 times the effect of the dioxin (2,3,7,8-tetrachlorodibenzo-p-dioxin [TCDD]) alone (van Birgelen et al. 1996). Alternatively, chemical mixtures can have competing effects, reducing the total chemical effects.
    This observation of differing health effects of chemical
    mixtures poses real difficulties for toxicity testing and regulatory efforts, which often rely on chemical-by-chemical testing. This approach does not reflect the reality for children, who are exposed to a mixture of chemicals throughout their day. Our understanding of the effects of long-term, multiple, simultaneous, multi-generational exposures to low-level chemicals is just beginning.”

    That’s sort of what I meant by not relying on idealized models of looking at chemical effects in isolation, in pristine conditions (like ‘undistrubed soil’) , simply because we hope toxics are rendered harmless by natural processes.

  39. Walter, do pay attention. 4-methylcyclohexane is not the relevant compound (and, in fact, does not even exist as such. Methylcyclohexane does).

  40. A fuller picture, to hopefully diminish reliance on simplistic, idealized models of sorption and biodegradation of contaminants (let’s call that the wishful thinking, I really want to be believe that chemicals are rendered quickly harmless model), rather than persisting in the environment for decades, cycling through the ecosystem and in fact becoming more harmful and abundant in our water and food supplies over time (let’s call that the ‘what happens in reality’ model):

    “Solid wastes deposited in terrestrial environments are subject to leaching by surface and ground waters. Leachates may then be transported to other surface waters and drinking water aquifers through hydrologic transport. Leachates also interact with natural organic matter, clays, and microorganisms in soils and sediments. These interactions may render chemical constituents in leachates more or less mobile, possibly change chemical and physical forms, and alter their biological activity. Oceanic waste disposal practices result in migration through diffusion and ocean currents. Surface area-to-volume ratios play a major role in the initial distributions of chemicals in the aquatic environment. Sediments serve as major sources and sinks of chemical contaminants. Food chain transport in both aquatic and terrestrial environments results in the movement of hazardous chemicals from lower to higher positions in the food web. Bioconcentration is observed in both terrestrial and aquatic food chains with certain elements and synthetic organics. Bioconcentration factors tend to be higher for synthetic organics, and higher in aquatic than in terrestrial systems. Biodilution is not atypical in terrestrial environments. Synergistic and antagonistic actions are common occurrences among chemical contaminants and can be particularly important toxicity considerations in aquatic environments receiving runoff from several terrestrial sources.”

    full text here:

    note the following:

    “Leached materials from above ground disposal can percolate through soil horizons and into ground water. These materials as well as chemicals leached from subsurface burials can lead to possible contamination of drinking water aquifers or, through lateral movement of ground water, to contamination of surface waters. Sorption and desorption processes between the trace contaminants and the organic and mineral phases of the soil are usually strong and can prevent, or at least retard, movement of contaminants by groundwater. On the other hand, some chemical forms of trace substances are repelled from the soil phases and may move readily with water… Some contaminants present in wastes may interact with the soil exchange complex and become more or less soluble than one would expect. (pg. 297)

    “Soils tend to be the sink for most chemical contaminants released released to terrestrial environments. In addition to water relations and sorption-desorption phenomena discussed earlier, microbial interactions and root uptake play major roles in transport and distribution of chemicals in terrestrial systems. Microbes can operate in both aerobic and anaerobic environments and have profound effects on chemical mobility. From the soil-soil-water continuum, plants may accumulate chemicals through root uptake, a process of both active and passive nature. ” (pg 301)

    “Elimination of chemicals through the various tissues of consumers proceeds at various rates and results in the release of the chemical into the digestive or urinary tract to be released from the consumer through egestion. Consumers may die or they may be consumed by subsequent steps in the food chain. Compounding this simplified of a food chain are the biotransformations that may occur, changing the structure and biological activity of the chemicals, and the question of direct uptake from surrounding air (inhalation) and water (gill and epidermal absorption). (pg. 301)

    Also see:

    “An important criterion for evaluating the significance and risks of PCDD/Fs and other POPs at contaminated sites is their present or future potential for mobility. This, in turn, determines to a large degree their propensity for off-site transport and environmental accessibility. The detailed evaluation of contaminated site cases reveals different site-specific factors, which influence the varied pathways through which poor water-soluble POPs can be mobilised. Co-contaminants with greater water solubility are also typically present at such sites. Hence, pumping of groundwater (pump and treat) is often required in addition to attempting to physically secure a site. At an increasing number of contaminated sites, securing measures are failing after relatively short time spans compared to the time horizon, which applies to persistent organic pollutant contamination.”

  41. Herbal #45 I’m not buying that. I’m sure you are right that this is a major effect, but I can imagine ways compounds could re enter a state of viability or creep into animal diets. Eg via dirt or dust on food, or changes in soil ph or mechanical effects.

  42. Remediation might have concern for the possible cross contamination principle:
    ” How the compounded substance reacts (or not) when combined with one or more multiple contaminates” so you may be “filtering” something completely foreign to your MSDS call outs.
    Now imagine the chemicals Not accounted for which daily seep (or pour) into the biosphere. Sure the soil may neutralize this stuff over time, the bacteria are surely available (when the temp is over 41 degrees), the water may mitigate some of the stuff (read spread over long distance and into underground aquifers, out of sight, out of jurisdiction).
    The lady in W.V. got it very right … these people need immediate relief. That pretty much is not going to happen.
    Two weeks of foot dragging for investigation, Two months of backlash for legal and court rulings (that would be vapor fast) and half baked solutions (dragging a cotton filter over the water, etc.) and at least one year of mobil transport. NOW you are dealing with the junk leftover (attaches to what, when, where and how) THAT is what you will eventually be cleaning up. Now, what drinking water and bathing? Knowing absolutely nothing about this stuff and banking on previous remediation for toxic wastes including nuclear sludge – making a Multiple Dimensional Pass would at least make this water workable. 1.) Humates and Truck In Soil stage one, 2.) Ultrasonic cavitation and carbon filters stage two, 3.) Settling and aeration tanks evaluation measurements stage three, 4.) maybe ready to start process over again.
    I would home brew my own process before trusting authority on this cleanup or any other for that matter. (Humate, soil, Filter, repeat, – Lather, Rinse, Repeat) then have the water TESTED before bathing much less drinking.
    Not much time for bacteria, or affordable Cavitation devices for much more firepower.

    Oh yeah, I see Joe and Shelley are deeply disappointed and Dr. K of the CDC will defend its honor to the death … LET THEM DRINK THIS STUFF then tell us how “Disappointed” they are in their multi million dollar homes and jobs.

    Maybe the authorities can at least TEST for free.

    I have seen cardboard boxes of radiated waste buried in open / barely covered trenches at Maxey Flats – Morehead, KY. This is just about oversight … NO SIGHT AT ALL.

    I either drink water that is R.O. triple filters or Berkey Gravity Filter water (NEVER LEXINGTON water from tap … NEVER)
    and now maybe people can see why.

  43. How many thousands (millions?) of gallons of this chemical are produced annually? After cleaning coal does it all end up washing down rivers?

  44. “Herbal #45 I’m not buying that. I’m sure you are right that this is a major effect, but I can imagine ways compounds could re enter a state of viability or creep into animal diets. Eg via dirt or dust on food,”

    Dirt or dust on food isn’t going to make a difference to whether the compound is too strongly sorbed to the matrix to be bioavailable. Stomach pH might make a difference.

    However, EPA detection protocols are pretty aggressive, particularly for leachates (e.g. agitation in citric or acetic acid for 3-5 days, IIRC) followed by GC-MS; you also have the problem that GC-MS will detect based on fragments of molecules, and may not perceive degradation of the compounds caused by sorption to the soil matrix. So again, it’s not the necessarily the case that if something is bound to the soil matrix that it’s readily bioavailable. The risk doesn’t go up or down because our detection technology gets better.

  45. Please note in your calculations that the 4-MCHM is only one ingredient of the
    CRUDE MCHM (Product ID # P1871700) that was spilled.

    I think it is also important to note that it is incompatible with strong oxidizing agents.

    Until WVAW discloses what they treated the water with, we don’t know what is in our chemical cocktail that WVAW has repeatedly told its customers is “safe” to consume and have in their household plumbing.

    (Data from MSDS)

    4-methylcyclohexanemethanol (CAS Reg No.34885-03-5)

    4-(methoxymethyl)cyclohexanemethanol (CAS Reg No.98955-27-2)

    water (CAS Reg No.7732-18-5)

    methyl 4-methylcyclohexanecarboxylate (CAS Reg No.51181-40-9)

    dimethyl l,4-cyclohexanedicarboxylate (CAS Reg No. 94-60-0)

    methanol (CAS Reg No. 67-56-‘ 1)

    (CAS Reg No. 05-08-8)

    *Here is the source 2005 MSDS:

  46. “Also see:

    Phillydoug, that paper is talking about low-solubility, low-mobility chlorinated compounds, and mentions one of the conditions for their mobilization is the presence of DNAPLs.

    This is not a DNAPL. This is not a chlorinated compound. This is not a compound that bioaccumulates. Cutting-and-pasting fate-and-transport papers for chemically unrelated families of compounds isn’t relevant here.

  47. Analyzing it chemical, the effects of heavier alcohols depends on what the liver converts it to. It generally goes to aldehyde, and then acid. Methanol goes to formic acid, which is quite toxic; ethanol to acetic acid (the acid in vinegar), which is why heavy drinkers smell sour.

    Presumably, the liver’s first pas would convert to the aldehyde, 4-methylcyclohexane methanal, which I am unsure about (formaldehyde is a known carcinogen, but this would have a short half-life in the body). The it would be converted into 4-methylcyclohexane formic acid — again, the formic acid part could be toxic but I don’t know about the entire molecule. The hydrocarbon part should not be dangerous in moderate quantities.

  48. Greg,

    It’s easy for things to fade in the background when so much awful stuff is happening in the world, but the slow poisoning of our friends in West Virginia continues, and will be continuing for decades to come:

    “West Virginia inspectors have discovered 600 more above-ground chemical storage tanks located near public drinking-water supplies, pushing their current inventory to more than 1,600 such tanks, according to data made public Thursday.
    The Department of Environmental Protection for the first time released lists of storage tanks that could be subject to new rules if lawmakers pass legislation drawn up in response to the January chemical leak on the Elk River.”

    “A new report from the West Virginia Rivers Coalition and the consulting firm Downstream Strategies identifies more potential threats of contamination to the Elk River, the drinking water supply for 300,000 state residents.

    The report, based on new information from state regulators, lists 63 potential pollution threats, more than the 52 that were contained in a decade-old report published by the state Department of Health and Human Resources.

    Forty commercial, 17 industrial and five municipal facilities — everything from above-ground storage tanks to wells producing natural gas — are on the list of “potential significant contamination sources,” or PSCSs.”

    “The chemical spill in January that contaminated drinking water for 300,000 West Virginians around Charleston has brought national attention to issues of water safety. But many rural West Virginians outside the reach of the spill have been living without tap water for drinking for months — or even years…

    Between 2,000 and 3,000 people in McDowell County itself do not have access to clean tap water or suitable well water, she said.

    “I’m 54 years old and, as long as I can remember, people have collected water from a spring or old mine source up on U.S. Route 54 in Maybeury. Any time of day you can see trucks loading their tanks,” she said. Road-side collection sites are often a single PVC pipe jutting out from an embankment.”

    Just to be clear, this is how we all allow our fellow Americans to live.

    The cynical side of me predicts that some well-informed chemist with experience in the industry will again make the claim that any individual spill, like the one at Elk River, will pose only minimal threats to humans (and wildlife, and the environment), because natural degradation and sequestration processes will make it so. Precisely the kind of magical thinking (the textbook says that this chemical, in isolation, will be confined in sediment, and so no combination of factors, or slow accretion of multiple toxics over decades, need to factored into the analysis) that has brought West Virginia to where it is today.

    Maybe industry affiliated chemists need to reflect a bit more on the admonition of Upton Sinclair:

    “It’s hard to make a man understand when his livelihood depends upon him not understanding”.

    My income isn’t tied to chemical industry profits; maybe that’s why this circumstance seems so despicable to me.

  49. Alan: “Have you tried activated-carbon filters?”

    I use them for my drinking water at home.

    How is that a response to the poisoning of the waters of West Virginia, for decades, harming millions of people, simply for the sake of profit?

    Even if carbon activated filters made drinking water from Elk River 100% of the time (feel free to go there to try that experiment yourself, and also explain why such filters aren’t simply installed in the homes of every West Virginian– hint: because it won’t actually fix the problem), how exactly would that address the environmental effects, agriculture, fishing? (hint– it doesn’t).

    And even if remediation efforts would remove all toxics from the soil and ground water (they’ve been trying for about forty years, and also doing some magical thinking hoping the toxics will simply evaporate; hint: they don’t), even if all our wishes came true and all these pollutants simply vanished– still, how would it it make it ok to dump the poisonous slop into the water and soil in the first place, simply because it’s profitable? Study any logic? Ever? How about moral philosophy?

    You may also consider reading up on the accumulation of industrial chemicals in soil and water (hint: places get designated Superfund sites for a reason), and many areas (including one not far from where I live) are simply closed off to the public, because the technology and methods to remediate some of the pollutants doesn’t yet exist.

    In particular, read up on the effect of industrial pollutants on ecosystems, and human health (q.v. the links I posted at comments #49 and #51).

    After you actually read the research, get back to me, and help me better understand your views of the situation in West Virginia, why thousands of people have no drinking water sources, and why you think carbon activated filters sounds like a plausible response to you.

    If you are serious about looking at the research, I’m happy to discuss it further with you.

    1. Thank you for your reply. We use reverse osmosis for drinking water, but that’s only a small part of the total use of water. I have read somewhere that some industrial pollutants have altered the genital structures in some newborn babies (e.g., XY get female genitals). I expect the situation (water pollution) — and everything else — will get worse before they get better.

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