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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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January 30, 2014

The West Virginia Formaldehyde Claim Is Nonsense

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Posted by Derek

This morning I heard reports of formaldehyde being found in Charleston, West Virginia water samples as a result of the recent chemical spill there. My first thought, as a chemist, was "You know, that doesn't make any sense". A closer look confirmed that view, and led me to even more dubious things about this news story. Read on - there's some chemistry for a few paragraphs, and then near the end we get to the eyebrow-raising stuff.
4-MCHM.png
The compound that spilled was (4-methylcyclohexane)methanol, abbreviated as 4-MCHM. That's its structure over there.

For the nonchemists in the audience, here's a chance to show how chemical nomenclature works. Those lines represent bonds between atoms, and if the atom isn't labeled with its own letter, it's a carbon (this compound has one one labeled atom, that O for oxygen). These sorts of carbons take four bonds each, and that means that there are a number of hydrogens bonded to them that aren't shown. You'd add one, two, or three hydrogens as needed to each to take each one up to four bonds.

The six-membered ring in the middle is "cyclohexane" in organic chemistry lingo. You'll note two things coming off it, at opposite ends of the ring. The small branch is a methyl group (one carbon), and the other one is a methyl group subsituted with an alcohol (OH). The one-carbon alcohol compound (CH3OH) is methanol, and the rules of chemical naming say that the "methanol-like" part of this structure takes priority, so it's named as a methanol molecule with a ring stuck to its carbon. And that ring has another methyl group, which means that its position needs to be specified. The ring carbon that has the "methanol" gets numbered as #1 (priority again), so the one with the methyl group, counting over, is #4. So this compound's full name is (4-methylcyclohexane)methanol.

I went into that naming detail because it turns out to be important. This spill, needless to say, was a terrible thing that never should have happened. Dumping a huge load of industrial solvent into a river is a crime in both the legal and moral senses of the word. Early indications are that negligence had a role in the accident, which I can easily believe, and if so, I hope that those responsible are prosecuted, both for justice to be served and as a warning to others. Handling industrial chemicals involves a great deal of responsibility, and as a working chemist it pisses me off to see people doing it so poorly. But this accident, like any news story involving any sort of chemistry, also manages to show how little anyone outside the field understands anything about chemicals at all.

I say that because among the many lawsuits being filed, there are some that show (thanks, Chemjobber!) that the lawyers appear to believe that the chemical spill was a mixture of 4-methylcyclohexane and methanol. Not so. This is a misreading of the name, a mistake that a non-chemist might make because the rest of the English language doesn't usually build up nouns the way organic chemistry does. Chemical nomenclature is way too logical and cut-and-dried to be anything like a natural language; you really can draw a complex compound's structure just by reading its name closely enough. This error is a little like deciding that a hairdryer must be a device made partly out of hair.

I'm not exaggerating. The court filing, by the law firm of Thompson and Barney, says explicitly:

30. The combination chemical 4-MCHM is artificially created by combining methylclyclohexane (sic) with methanol.

31. Two component parts of 4-MCHM are methylcyclohexane and methanol which are both known dangerous and toxic chemicals that can cause latent dread disease such as cancer.

Sure thing, guys, just like the two component parts of dogwood trees are dogs and wood. Chemically, this makes no sense whatsoever. Now, it's reasonable to ask if 4-MCHM can chemically degrade to methanol and 4-methylcyclohexane. Without going into too much detail, the answer is "No". You don't get to break carbon-carbon bonds that way, not without a lot of energy. If you ran the chemical (at high temperature) through some sort of catalytic cracking reactor at an oil refinery, you might be able to get something like that to happen (although I'd expect other things as well, probably all at the same time), but otherwise, no. For the same sorts of reasons, you're not going to be able to get formaldehyde out of this compound, either, not without similar conditions. Air and sunlight and water aren't going to do it, and if bacteria and fungi metabolize it, I'd expect things like (4-methylcyclohexane)carboxaldehyde and (4-methylcyclohexane)carboxylic acid, among others. I would not expect them to break off that single-carbon alcohol as formaldehyde.
MeOH%20rxn.png
So where does all this talk of formaldehyde come from? Well, one way that formaldehyde shows up is from oxidation of methanol, as shown in that reaction (this time I've drawn in all the hydrogens). This is, in fact, one of the reasons that methanol is toxic. In the body, it gets oxidized to formaldehyde, and that gets oxidized right away to formic acid, which shuts down an important enzyme. Exposure to formaldehyde itself is a different problem. It's so reactive that most cancers associated with exposure to it are in the upper respiratory tract; it doesn't get any further.

As that methanol oxidation reaction pathway shows, the body actually has ways of dealing with formaldehyde exposure, up to a point. In fact, it's found at low levels (around 20 to 30 nanograms/milliliter) in things like tomatoes and oranges, so we can assume that these exposure levels are easily handled. I am not aware of any environmental regulations on human exposure to orange juice or freshly cut tomatoes. So how much formaldehyde did Dr. Scott Simonton find in his Charleston water sample? Just over 30 nanograms per milliliter. Slightly above the tomato-juice level (27 ng/mL). For reference, the lowest amount that can be detected is about 6 ng/mL. Update: and the amount of formaldehyde in normal human blood is about 1 microgram/mL, which is over thirty times the levels that Simonton says he found in his water samples. This is produced by normal human metabolism (enzymatic removal of methyl groups and other reactions). Everyone has it. And another update: the amount of formaldehyde in normal human saliva can easily be one thousand times that in Simonton's water samples, especially in people who smoke or have cavities. If you went thousands of miles away from this chemical spill, found an untouched wilderness and had one of its natives spit in a collection vial, you'd find a higher concentration of formaldehyde.

But Simonton is a West Virginia water quality official, is he not? Well, not in this capacity. As this story shows, he is being paid in this matter by the law firm of Thompson and Barney to do water analysis. Yes, that's the same law firm that thinks that 4-MCHM is a mixture with methanol in it. And the water sample that he obtained was from the Vandalia Grille in Charleston, the owners of which are defendants in that Thompson and Barney lawsuit that Chemjobber found.

So let me state my opinion: this is a load of crap. The amounts of formaldehyde that Dr. Simonton states he found are within the range of ozonated drinking water as it is, and just above those of fresh tomato juice. These are levels that have never been shown to be harmful in humans. His statements about cancer and other harm coming to West Virginia residents seem to me to be irresponsible fear-mongering. The sort of irresponsible fear-mongering that someone might do if they're being paid by lawyers who don't understand any chemistry and are interested in whipping up as much panic as they can. Just my freely offered opinions. Do your own research and see what you think.

Update: I see that actual West Virginia public health officials agree.

Another update: I've had people point out that the mixture that spilled may have contained up to 1% methanol. But see this comment for why this probably doesn't have any bearing on the formaldehyde issue. Update, Jan 31: Here's the MSDS for the "crude MHCM" that was spilled. The other main constituent (4-methoxymethylcyclohexane)methanol is also unlikely to produce formaldehyde, for the same reasons given above. The fact remains that the levels reported (and sensationalized) by Dr. Simonton are negligible by any standard.

Comments (111) + TrackBacks (0) | Category: Chemical News | Current Events | Press Coverage | Toxicology


COMMENTS

1. annonie on January 30, 2014 10:15 AM writes...

Said from the viewpoint of a chemist.

Actually, formation of methanol or formaldehyde or formic acid plus methyl benzene is not all that unreasonable, which could be done by micro-organisms.

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2. Puff the Mutant Dragon on January 30, 2014 10:20 AM writes...

I blogged about the West Virginia spill too, lol. The accident has wrought havoc with the water supply and caused a lot of people a lot of grief, but...there's no sense in spreading panic by making it sound like it's worse than it really is. It's kind of appalling that a scientist (Scott Simonton) would help promote this kind of nonsense.

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3. Wheels17 on January 30, 2014 10:21 AM writes...

My favorite example for non-chemists is the chemical that you have in your kitchen composed of a metal that burns and explodes when dropped in water, and a poison gas used in WW I.

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4. Chemjobber on January 30, 2014 10:24 AM writes...

Thanks for the links, Derek! I note that it was not me that found the lawsuit, but a reader of mine (and a chemist) who is sipping sub-ppb levels of MCHM in their water.

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5. SP on January 30, 2014 10:28 AM writes...

I wouldn't be surprised if there were other chemicals beside MCHM in the leaking tank that were not properly disclosed/reported- the company responsible seems to have been a shell expressly created for the purpose of shielding other real companies from liability, so they're not really motivated to spend much time being careful. But the reported level of formaldehyde doesn't support the argument that any formaldehyde precursors were there.

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6. Curious Wavefunction on January 30, 2014 10:31 AM writes...

Nice takedown. Not to mention that formaldehyde is naturally produced in the human body as the breakdown product of many enzyme demethylations. And it's even released by some antibiotic drugs like ampicillin prodrugs. The dose does make the poison. But none of thus will convince alarmist chemophobes.

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7. See Arr Oh on January 30, 2014 10:35 AM writes...

I've been trying all morning to retrosynthetically (take the molecule apart, backwards) disconnect MCHM to produce formaldehyde and "cyclohexyl anion," or some equivalent. I just don't see a feasible way, short of invoking some high-energy radical.

Anyone else?

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8. BG on January 30, 2014 10:36 AM writes...

What were these guys using 4-MCHM for? Only TCI sells it, and it's fairly expensive (5g = $105)

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9. db on January 30, 2014 10:48 AM writes...

8: don't know what specifically they used it for, but the company, Freedom Industries, sells (makes?) polymers and polymer blends for, somewhat ironically, industrial wastewater treatment.

A former employer of mine bought their polymers for sludge thickening operations and scrubber liquor clarification.

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10. Pig Farmer on January 30, 2014 10:55 AM writes...

Absolutely spot on, Derek. I'm the chemist who sent the lawsuit to Chemjobber a couple of weeks ago. I'm not drinking the water yet, not because I'm afraid of any possible toxicity, but I just don't like the taste of MCHM, and it has a very low odor threshold (0.5 ppb). You're absolutely right that this is written purely for the lawyers benefit, and is sloppy journalism and irresponsible scaremongering of the sort you always see when chemicals make the headlines. I also agree that the head honchos at Freedom Industries need to do some serious jail time over this, since it seems obvious to me that this is a case of criminal negligence. Fortunately Freedom Industries has been ordered to dismantle their facility on the Elk River, commencing no later than 3/15/14. Good riddance to them. I do, however, feel sorry for the workers who will lose their jobs over this. Meanwhile the President of this lousy outfit continues to live it up at his Marco Island mansion.

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11. Pig Farmer on January 30, 2014 11:00 AM writes...

http://en.wikipedia.org/wiki/2014_Elk_River_chemical_spill
MCHM is a foaming agent used to clean up coal.

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12. Anonymous on January 30, 2014 11:03 AM writes...

They use it to "clean" coal, I think specifically to separate out really small particles.

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13. Philip on January 30, 2014 11:09 AM writes...

"And the water sample that he obtained was from the Vandalia Grille in Charleston, the owners of which are defendants in that Thompson and Barney lawsuit that Chemjobber found."

I think you mean plaintiffs, not defendants. If I am wrong, please delete this post. If I am correct, please edit the story and delete this post.

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14. Bob Sacamano on January 30, 2014 11:11 AM writes...

David Zucchino wrote an interesting piece about this in the LA Times today (link in handle). It includes this gem about the other chemical (a polyglycol ether) involved in the spill:

"Then the chemical company responsible for the spill belatedly admitted a second, equally unpronounceable chemical containing ether also had been dumped into the water."

And now we have diethyl ether coming out of the taps. Remarkable.

The LAT is scrambling to correct the formaldehyde nonsense, but the ether reference remains.

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15. BG on January 30, 2014 11:12 AM writes...

Thanks 9 and 11.

7: You could do an elimination to make the the exocyclic alkene, ozonolyze and DMS quench to make formaldehyde and the cyclohexanone. Then do a Wolff-Kishner reduction on the ketone to the alkane.

You could go directly to the methylcyclohexane by oxidizing the alcohol to the aldehyde then doing a rhodium catalyzed decarbonylation- but I don't know of any ways to reduce the CO to formaldehyde.

Or as you pointed out you could invoke high energy radical intermediates: Blast the stuff with gamma radiation and pray that the correct bonds break and the correct bonds form in the resultant chaos.

Obviously none of these processes are happening in the river.

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16. cirby on January 30, 2014 11:13 AM writes...

Considering that the lethal dose of MCHM in rats is pretty high (825 mg/kg), and you can taste the stuff at fractional parts per billion...

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17. Hap on January 30, 2014 11:14 AM writes...

I can see P450 oxidizing next to the alcohol on the cyclohexane, but even then it probably wouldn't fragment to formaldehyde and 4-methylcyclohexanone. If you oxidized 1-HO-4-CHM to the aldehyde, retro-Claisen might get you formate and 4-methylcyclohexanone. Fragmentation conditions to give you formaldehyde would probably give you formate and/or methanol by Cannizzaro reaction or formic acid/CO2 by oxidation.

When someone can make lots of money (or thinks they can) by not knowing something, this is what happens.

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18. NoDrugsNoJobs on January 30, 2014 11:18 AM writes...

Perhpas more relevant to what levels of formaldehyde are problematic, normal human plasma levels of formaldehyde are around 2.6 uG/mL; actually fairly high when you consider that the half life in plasma is about 1-2 minutes! This is a pretty high background (baseline) level, particularly on a molar basis. Drugs that have the ability to oxidize a methyl (phenol methyl ethers) or hydrolyze a methanol (methyl esters)will also generate formaldehyde and formic acid (formate). This is generally not an issue in view of the high daily endogeneous production and metabolism of formaldehyde. Its most troubling effects tend to be site specific (inhalation, skin contact) where a localized concentration might be higher and pass the tolerability thresholds.

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19. Curt F. on January 30, 2014 11:19 AM writes...

Can someone explain (using either IUPAC nomenclature or even historical arguments) why methylcyclohexanemethanol ever came to be a commonly used name for the chemical? Wouldn't either 1-hydroxymethyl,4-methylcyclohexane or (4-methylcyclohexyl)methanol be much better names than methylcyclohexanemethanol?

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20. See Arr Oh on January 30, 2014 11:22 AM writes...

@BG, @Hap - Yeah, those all seem viable to me. As Hap points out, most oxidative fragmentation or rearrangment conditions give formate, which (thankfully) won't raise an environmental ruckus.

But BG has the truth of it: None of these potential reactions happens in water at 20 deg C, even when invoking microorganisms.

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21. JS on January 30, 2014 11:22 AM writes...

For what it's worth, the spill is generally said to be of "crude 4-MCHM". And according to the Eastman Chemicals SDS, that is a mixture of a number of related compounds, plus 4-10% water and 1% methanol. (SDS is linked in name.)

I totally agree with Derek's post; I'm just trying to put a little more information out there.

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22. qvxb on January 30, 2014 11:23 AM writes...

1 ng/mL = 1 µg/L = 1 ppb = 0.001 mg/L = 0.001 ppm

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23. Gene on January 30, 2014 11:25 AM writes...

Understanding chemistry? I had zero chemistry in grade/high school. That paragraph on nomenclature is more formal training than I've ever had.

I only understand most of this stuff because I'm a computer science guy, and it's got the same sort of formal logic to a lot of it, plus there's Google now.

However I don't understand the lawyers, as their chemistry errors could be a way for the opposition to win, since their lawsuit is wrong on facts. They need to be up on this.

These guys look like the sort that would fall for the dihydrogen monoxide bit in a heartbeat.

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24. oldnuke on January 30, 2014 11:37 AM writes...

No doubt the formaldehyde in the water supply is from a V-8 juice spill a few years ago.

I wonder how many WVa teachers are capable of explaining why this is junk "science"?

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25. PPedroso on January 30, 2014 11:38 AM writes...

Love these type of posts! Thanks Derek!

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26. Chemjobber on January 30, 2014 11:39 AM writes...

Worth noting (link in my handle) that there is 1% of methanol in crude MCHM, according to Eastman. So it's not especially surprising that formaldehyde might be detected in the water? (dunno how fast air oxidation of MeOH to formaldehyde happens... not very, I'd assume.)

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27. Anon8 on January 30, 2014 12:06 PM writes...

Derek: You go at length to describe the chemistry, nomenclature and other sane logic that we the chemists fully agree but at the end of the day the jury that gets hired to settle on these and other issues will not be the chemists! They will be not included in the jury pool by systematic elimination by the lawyers in a pre-trial move. Not long back we had one of those safety meeting for the chemists, the OSHA regulation etc. Guess what, the guy who preached (the do’s and do not) was not even a chemist, but was a lawyer. I reached the conclusion that we the chemists will never win. When you are going to litigate an issue that is full of emotions, the rationality takes the backseat

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28. Hap on January 30, 2014 12:07 PM writes...

21: It's probably (although I don't know how they made it) a Diels-Alder/reduction product from isoprene and acrolein, so probably parent aldehyde might (probably not) be around and D-A regioisomers in addition to diastereomers of 4-MCHM. (I'm assuming the reactants were distilled off, probably before reduction.) There could be aromatized product (3/4-methylbenzaldehyde) present as well. (The benzaldehydes would probably go to benzoic acids under ambient conditions, which aren't going anywhere I think.)

None of these, though, have a really good path to generating formaldehyde under ambient conditions. The 1% MeOH could easily generate formaldehyde through biological oxidation but probably can't generate it at a very high concentration (air oxidation, as Chemjobber noted, probably is glacial).

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29. Pig Farmer on January 30, 2014 12:17 PM writes...

http://en.wikipedia.org/wiki/4-Methylcyclohexanemethanol
MCHM is a by-product from hydrogenation of dimethyl terephthalate

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30. Hasufin on January 30, 2014 12:21 PM writes...

Thank you so much for the clear explanation of how the chemical is named and represented. I only wish my chemistry textbooks had been so straightforward. I'm going to have to bookmark this post, so I can consult it when I want to make sense of some chemical name.

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31. JM on January 30, 2014 12:33 PM writes...

"Sure thing, guys, just like the two component parts of dogwood trees are dogs and wood"

You sir, are a genius

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32. MGlass on January 30, 2014 12:42 PM writes...

Well, chemistry folk, we could really use your expertise on this issue and appreciate you sharing your knowledge. However, before you form your opinions and present them publicly, I suggest you pay attention to what was actually reported as spilled from the Freedom Site. The spilled material consisted MOSTLY of a product called Crude MCHM. This includes MCHM as well as a 1% concentration of methanol. At a minimum, 10,000-gallons of Crude MCHM was released.
As working chemists, you should have to spend little time in locating the Safety Data Sheet for Crude MCHM from Eastman Chemical, which presents the component concentrations.
Again, if you have any informed insight to share, we in WV really appreciate the help.

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33. Nate on January 30, 2014 1:02 PM writes...

If it helps nail a highly negligent company (or shell company) to the wall them I'm all for the fear mongering. They are spinning it that a lot of methanol is in the water, the coal people are claiming MCHM is near harmless and this is not a big deal. It's a propaganda fight and I hope the people win

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34. newnickname on January 30, 2014 1:07 PM writes...

There's some info at ToxNet. Too much to cut and paste, so I'll pick and choose:

Environmental Fate/Exposure Summary:
Methylcyclohexanol's production and use as a solvent for cellulose esters and ethers and for lacquers resins, oils, and waxes, an antioxidant for lubricants, and a blending agent for special textile soaps and detergents may result in its release to the environment through various waste streams. Methylcyclohexanol is a commercial mixture that contains isomers of 2-, 3-, and 4-methylcyclohexanol, which are expected to behave in a similar manner in the environment.

4-Methylcyclohexanol degraded 94.0% during a 5-day screening test using an acclimated sewage inoculum.

Environmental Biodegradation:
AEROBIC: Methylcyclohexanol is a commercial mixture that contains isomers of 2-, 3-, and 4-methylcyclohexanol, which are expected to have behave in a similar manner in the environment(SRC). 4-Methylcyclohexanol degraded 94.0% based on COD removal in a 5-day screening test using an acclimated activated sludge inoculum(1).
[(1) Pitter P; Water Res 10: 231-5 (1976)]


toxnet.nlm.nih.gov /cgi-bin/sis/search /a?dbs+hsdb:@term+@DOCNO+2910

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35. Curt F. on January 30, 2014 1:17 PM writes...

@35. newnickname. "4-methylcyclohexanol" is a different compound. It has no CH2 group between the OH and the cyclohexane ring.

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36. Pig Farmer on January 30, 2014 1:31 PM writes...

I don't think Derek or anyone else here is trying to make light of this case of criminal negligence. I live in Charleston, WV, and believe me, I am mad as hell about what happened. I want those guys to do jail time. But it doesn't help anyone to make overblown statments about the toxicity of MCHM, or the risk of cancer from the levels of formaldehyde in the water that we are seeing. I am using the water for showering and washing clothes and dishes as normal. I'm not drinking it because it still tastes of industrial solvent, which I don't like. But I am not worried that I'm going to be poisoned or die of cancer down the line because of this. Am I 100% certain of this? Of course not. But I place the risk of death from this chemical way below the risk of, say, being killed in a car accident on the way to work.
To repeat. There is no excuse for what happened, Freedom Industries have lost their right to operate in the area, and the owners should be prosecuted for criminal negligence. But lets not let our justified anger with the owners of this outfit cloud our judgement as to the risks associated with these chemicals. Logic has to be brought to bear on this issue, and that is what Derek is doing here.

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37. Anonymous on January 30, 2014 1:31 PM writes...

@14 miralax is made of polyethylene glycol. you have to chug down quite a bit of the stuff for it to achieve the desired effect. i wonder if whatever polyglycol ether was spilled would be any more dangerous (i would naively assume not)

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38. Anonymous on January 30, 2014 1:41 PM writes...

"just like the two compon