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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 22, 2013

Pick Your Stench

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Posted by Derek

OK, folks, time to choose: would you rather be downwind of an industrial-scale spill of butyl mercaptan (which started in Rouen and is already being smelled in London), or. . .would you rather deal with a twenty-seven tons of burning goat cheese in Norway?

Tough call. I think, though, that I might go with the devil I know, which means the mercaptan. I've never encountered a Goat Cheese Inferno, and I live in fear of discovering even more revolting odors than I've already experienced. Good luck to the Norwegians, I say.

Update: for the curious, natural gas odorant mixes are usually t-butylthiol and isopropyl thiol, with perhaps some other lovelies (dimethyl sulfide) thrown in for that special je ne sais quoi. Although across northern France today, I'll bet they can tell you quoi for sure at the moment.

Comments (35) + TrackBacks (0) | Category: Current Events


COMMENTS

1. Chemist For Life on January 22, 2013 1:11 PM writes...

You can't 'bleat' a good goat cheese fire.

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2. LeeH on January 22, 2013 1:26 PM writes...

Goat cheese inferno fondue is my favorite.

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3. jtd7 on January 22, 2013 1:29 PM writes...

I saw Goat Cheese Inferno open for the Flaming Lips.

No, wait, it was the other way around.

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4. DannoH on January 22, 2013 1:43 PM writes...

Ill take the butyl mercaptan spill anyday! My olfactory receptors were burnt out on a large bolus dose of lovely organic thiols years ago. All things being equal (smell wise) I will take skunk over nasty-ass cheese anyday.

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5. Bear on January 22, 2013 1:48 PM writes...

Either one has to be better than being downwind of Congress.

(How the hell does 27 tons of cheese catch fire in the back of a truck?)

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6. cynical1 on January 22, 2013 1:51 PM writes...

Actually, to the best of my knowledge, methane thiol, not butyl mercaptan, is added to natural gas so you can smell it. Butyl mercaptan is a liquid at room temperature. The link just calls it mercaptan. And since I've had the unfortunate pleasure of working with it on a kilo scale in a pilot plant, I'll take the burning cheese even though I don't know what that smells like.

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7. luysii on January 22, 2013 1:57 PM writes...

My senior thesis involved intramolecular hydrogen bonding of various side chains to the pi electron cloud of benzene (this was 1959 remember). Naturally the thiols had to be studied, e.g. benzene-butyl-SH vs. n-Bu-SH, to look at the infrared SH stretching region of both. I saved the n-BuSH for last, but there were even worse smelling thirds (particularly nPr-SH, and EtSH) -- probably because they were more volatile.

People used to look at their shoes to see if they'd stepped in something when I'd walk into the dining room of my eating club.

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8. nitrosonium on January 22, 2013 2:19 PM writes...

my thesis work involved studying the kinetics and thermodynamics of nitrosonium (NO+) transfer from electron deficient C-nitroso compounds to primary, secondary and tertiary thiols. I actually love the smell of thiols!!! not kidding. i am sick. i know. perhaps 14 yrs in the basement lab have not helped.

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9. RB Woodweird on January 22, 2013 3:00 PM writes...

Someone in a biology lab at Boston University back in the late 70s or so, before the reconstruction of the sewer into separate septic/rainwater lines, poured a liter of butanethiol down the drain during a lab clean up. The smell traveled down from the Comm Ave campus to the Charles via the Muddy River. Boston Gas was inundated with phone calls about a huge gas leak.

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10. FredB on January 22, 2013 3:09 PM writes...

Caramelized goat cheese. That stuff sounds like it's one step and an oxidizer away from being rocket fuel.

Yet another Norwegian delicacy. I can imagine long arctic winter nights with nothing better to do than dream up something to top lutefisk.

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11. nitrosonium on January 22, 2013 3:26 PM writes...

hey RB i have a related tale....even using the properly vented fume hoods, our work with thiols once caused an evacuation of the adjacent physics bldg because of a suspected gas leak. before we started using bleach buckets in the hoods, the maintenance guys frequently came into our lab looking for the gas leak....despite the fact that we had no gas lines in our lab!!

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12. CMCguy on January 22, 2013 3:47 PM writes...

I am with #4 DannoH as too lost long ago a refined sense of smell from exposure to various SH compounds so typically after initial brief whiff does not bother me much (not sure if we have the four-legged or two-legged grow-ops skunks around but occasionally do encounter foul odors). Further assume the cheese smell is likely from multiple molecules and thus more likely to get hit with something that does trigger a gag reflect.

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13. Mezzosoprano de Paris on January 22, 2013 4:15 PM writes...

I live on the western periphery of Paris and didn't smell a thing this morning until I watched the 8 a.m. news on tv and the first sentence was to reassure Parisians that the odor did not come from a noxious gas. Of course, we thought of what the Japanese heard about Fukushima...

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14. James on January 22, 2013 4:51 PM writes...

I live in Southern England. Something was definitely in the air this afternoon...

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15. cynical1 on January 22, 2013 5:20 PM writes...

According to the Financial Times:


High quality global journalism requires investment. Please share this article with others using the link below, do not cut & paste the article. See our Ts&Cs and Copyright Policy for more detail. Email ftsales.support@ft.com to buy additional rights. http://www.ft.com/cms/s/0/26211f9c-64af-11e2-934b-00144feab49a.html#ixzz2IkHmHsCt

"Lubrizol France, which makes additives for industrial lubricants and paint, said the gas was mercaptan, also known as methanethiol, a colourless additive used in natural gas because its sulphurous smell enables gas leaks to be detected.
Pierre-Jean Payrouse, internal operations director, said the company was battling to plug the leak, as the cloud spread over 350km but said it might take until the evening. The cause of the leak was still unknown."

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16. partial agonist on January 22, 2013 5:35 PM writes...

For the mercaptans I can arm myself with bleach or hydrogen peroxide and begin to deal with it.

Flaming goat cheese is more "the devil I don't know" so I guess I'd avoid it.

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17. Paul on January 22, 2013 5:52 PM writes...

Liquefied methane has been looked as a fuel for rocket engines. However, in testing, they discovered it clogged up cooling passages very quickly. On examination, it was found that the passages, which were made of copper for high thermal conductivity, were reacting with sulfur impurities to make copper sulfide.

As a result, the methane will either have to be highly purified (to maybe .1 ppm sulfur), or the cooling channels plated with an unreactive layer (gold, for example).

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18. hibob on January 22, 2013 7:00 PM writes...

Having considerable experience with both (so long as putting goat cheese and pine nuts under a broiler counts), I'll take flaming cheese anyday. Even if it does smell foul, the smell will rapidly dissipate. If it is butyl mercaptan that stench will hang around for quite a while and stick to everything that's downwind in Rouen, Including people. People will know you've been there until you've taken a shower and changed clothes.

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19. lechat on January 22, 2013 7:23 PM writes...

so what actually is the substance???

"mercaptan" is what someone told someone and what the newspapers are telling me, but that's hardly specific. I can't smell it from here.

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20. souls_at_zero on January 22, 2013 7:45 PM writes...

I'd take the goat cheese. It's not too 'cheesey' tasting, and I suspect its combustion odours would be more on the burned sugar side of the smell-spectrum. Maybe I'll go home and burn some tonight to confirm my suspicions.

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21. ColumnSympathiser on January 23, 2013 12:40 AM writes...

I must admit my disappointment that no one mentions the acrylate family of compounds in these "Nastiest Smelling Compounds" comments sections. I did some chemistry late last year that involved ethyl acrylate.

Ugh.

I think the smell of super glue will make me nauseous for the rest of my life.

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22. anonymous on January 23, 2013 7:13 AM writes...

Spent a month or so making a large series of an alkyl thio substituted analogs of a metabolite. Can assure you that a single shower didn't eliminate the stench of some of those suckers....

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23. Morten G on January 23, 2013 8:17 AM writes...

It's made from cow's milk - sorry. And it's not actually a cheese since it's made without rennet.

http://en.wikipedia.org/wiki/Brunost

Arctic dairy is a complicated subject though. Icelandic skyr is actually a cheese even though it tastes and acts like a yoghurt.

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24. Curious Wavefunction on January 23, 2013 8:20 AM writes...

Conversation between Linus Pauling and Matt Meselson

LP: Well, Matt, you know about tellurium, the group VI element below selenium in the periodic chart of the elements?
Me: Uh, yes. Sulfur, selenium, tellurium ...
LP: I know that you know how bad hydrogen sulfide smells. Have you ever smelled hydrogen selenide?
Me: No, I never have.
LP: Well, it smells much worse than hydrogen sulfide.
Me: I see.
LP: Now, Matt, Hydrogen telluride smells as much worse than hydrogen selenide as hydrogen selenide does compared to hydrogen sulfide.
Me: Ahh ...
LP: In fact, Matt, some chemists were not careful when working with tellurium compounds, and they acquired a condition known as "tellurium breath." As a result, they have become isolated from society. Some have even committed suicide.
Me: Oh.
LP: But Matt, I'm sure that you would be careful. Why don't you think it over and let me know if you would like to work on the structure of some tellurium compounds?

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25. Dave on January 23, 2013 8:28 AM writes...

One wonders if Polonium-breath would be even worse? Oh, wait, it's radioactive, so you'd be dead...

Dave

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26. KissTheChemist on January 23, 2013 8:41 AM writes...

I live in the suburbs of Paris (south) and we woke up to a gas leak kind of smell even though the plant in Rouen is about 80 miles away. I can't imagine what that smells like close up. Probably end up glad to smell 27 tons of burning goat's cheese just for a change! Bleeorg!

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27. Harry on January 23, 2013 8:45 AM writes...

Long ago I was involved in a spill of butyl mercaptan from a badly corroded drum that was still about 1/3 full. It was being moved across the plant for transfer to a new drum when the (badly dry rotted) pallet collapsed and the drum fell to the ground.

It was a nice fall day, about 60F, and the wind was kicking along about 40 mph. I got the job of supervising the cleanup. While we were in the midst of it, the air pollution control people showed up in response to our notification. They declined the opportunity to supervise the cleanup from close up, got back in their vehicle and left.

After a couple applications of 20% NaOH and 10% H2O2, we had it taken care of.

I found out later that the local gas companies had reports of natural gas leaks from as far away as 45 miles downwind.

I'll save the story of the 300 gallon methyl mercaptan spill for another time....

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28. Doug Steinman on January 23, 2013 11:29 AM writes...

The worst thing that I ever had to deal with, smell-wise is butyric acid.

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29. milkshaken on January 23, 2013 4:44 PM writes...

given the many fish-derived delicacies of Scandinavian cousines, I would wager it takes a lot to sicken Norwegians

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30. Flatland on January 23, 2013 6:50 PM writes...

This reminds me of a discussion I had with a colleague over some beers:

Which would smell worse, 4-mercaptobutyric acid or 3-mercaptopropionic acid (vapor pressure differences aside)? Does size play a role (would the 3-mercapto have that special 'butylness' or would the 4 be a 'better' match?

Which part would win out, the vomit smell, the burning skunk smell, or would it be something new and horrible in its own right?

Literature offers few answers, but google does turn up a references to the 3-mercapto being "Death in a RB flask. Vomit inducing if it escapes (and never comes out of your hair for weeks)"

These are the deep questions that we wish we knew/are afraid of/morbidly curious about the answers.

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31. anon on January 23, 2013 11:54 PM writes...

I've heard that Barry Sharpless was always fond of going around the lab and smelling people's compounds. That could explain some eccentricities.

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32. RB Woodweird on January 24, 2013 8:38 AM writes...

anon sez: "I've heard that Barry Sharpless was always fond of going around the lab and smelling people's compounds."

Freshman organic chem, early 70s. Sharpless is telling us about how he passed a lab practical to get into grad school at Stanford by burning an unknown and identifying it as a sugar by its smell. He says that he "used to go around smelling everything" - to which some half-awake wag behind me makes a quiet comment about bicycle seats not being safe on campus anymore.

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33. nitrosonium on January 24, 2013 10:28 AM writes...

lab practical to get IN to grad school??

i would never have been able to obtain a PhD back in the olden days of oranic chemistry!!

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34. norsci on January 24, 2013 9:26 PM writes...

Just to clarify: The goat cheese we're talking about is not like the molded, old, sock-smelling, aged crap they eat down in France (I guess they're handling the mercaptan just fine), it's something quite different called brunost (http://en.wikipedia.org/wiki/Brunost). Brunost is actually very sweet and has a taste remniscient of caramel. Try it if you get the chance!

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35. CFM on February 5, 2013 6:27 PM writes...

Being Norwegian and familiar with the exact kind of cheese involved, I'd say the cheese fire is the obvious lesser of two evils here. No rennet, no mold, and thus none of the typical "smelly cheese" aromas. I would imagine the fire smelling more like burning fudge than anything normally cheese-related.

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