Hacker News new | past | comments | ask | show | jobs | submit login
Things I Won't Work With: Thioacetone (2009) (science.org)
164 points by chris_overseas on Feb 25, 2023 | hide | past | favorite | 75 comments



A YouTuber went to the trouble of making it. https://youtu.be/LmAG8-V_WQY

He ends up doing the final step of the process on an uninhabited island in the middle of a lake for safety.


He seemed to not react too much to the smell. With all the other crazy stuff he does, he must be seriously desensitized to strong smells if that’s even possible…


In the article: “The odours defied the expected effects of dilution since workers in the laboratory did not find the odours intolerable.”


I think that bit is saying the chemists who synthesized the compound were desensitized to it, it’s right after a passage where they were ostracized and sprayed with deodorant at a restaurant during lunch


Full quote, which seems to say it defies the expected effects of dilution _because_ the chemists weren't bothered by it when they were right next to it, but when they were many yards away they could.

"The odours defied the expected effects of dilution since workers in the laboratory did not find the odours intolerable ... and genuinely denied responsibility since they were working in closed systems. To convince them otherwise, they were dispersed with other observers around the laboratory, at distances up to a quarter of a mile, and one drop of either acetone gem-dithiol or the mother liquors from crude trithioacetone crystallisations were placed on a watch glass in a fume cupboard. The odour was detected downwind in seconds."

In other words, the smell intensity increases with dilution, _not_ decreases. We must protect this data from the homeopaths.


Hydrogen sulfide rapidly desensitized the nose, it wouldn't be surprising for other sulfur compounds to do the same.


I don't think so. In NileRed's video it was clear that dilution made the odor worse than bring right next to it, which otherwise invoked a "chemical"-ey smell rather than a putrid trash+sewage smell.


I've never smelled this chemical, but I wonder if it's a little bit like skunk spray smell?

There's a saying! "Skunks don't have the WORST smell, just the MOST smell"

It's not the worst smell in the world. I would say it's not even remotely as unpleasant as summertime "dumpster soup", sewage, or whatever. But man, skunk smell is just so intense and overwhelming.


> “Skunks don't have the WORST smell, just the MOST smell"

I did my coding bootcamp in downtown Chicago, near the Merch Mart, and (at least back in 2013) there was a chocolate factory not too far away. I remember walking to class and being almost overpowered by the smell. For awhile it turned me off of chocolate entirely, and I normally have a pretty strong sweet tooth.

I remember feeling so sorry for the people who had to work there, day after day.


> I remember feeling so sorry for the people who had to work there, day after day.

As a kid one of the tours we did was a chocolate factory. When the person leading the tour told us the employee told us workers were allowed to take as much chocolate as they wanted we were super jealous.

At the end of the tour, there was a buffet of chocolate snacks nobody wanted to touch (though we were allowed to and did bring bags of products home), the person told us that after a day of working at the factory, most workers have no taste for chocolate snacks whatsoever, and those which do will generally fuck up, binge, get an indigestion, and at best be a lot more reasonable (at worse stop eating chocolate if it was bad enough). Without the allure of the forbidden fruit (sneaking snacks out), chocolate is definitely overpowering enough that it's a turn-off.


>> chocolate factory

Soup factories are notorious for smells. A single pot of cooking food generally smells good, but layer up a dozen different soup flavors and in total it smells like rot.


I live in 3 blocks from a chocolate factory, and don't find it disturbing. Rather nice. The first time I felt it at a marketplace nearby, and thought someone was making some hot chocolate stuff, and even wanted to take a look what it was, but couldn't find. Sometimes it gives a mild chocolate smell around, nothing more.


When my dog got sprayed by a skunk, it smelled overwhelmingly like a combination of burning rubber and rotten motor oil. Neither of these brands of smells is the worst I’ve ever encountered from a pure quality standpoint, but yes, it felt like it completely coated your nasal and throat passages. You choke on it.


Oh, dogs and smells, this makes me remember my poodle who, as every dog, would routinely look for stinky stuff to lay in. Once he found a dead cat -- it was rather nasty to wash him in the bath after that. Another time he was running around and found a rot fish thrown away near a trash tank -- this was the smelliest washing ever. Had to wash him twice with soap, then with shampoo. Another time, in winter, there was parking area covered with hard snow, compacted by car tires. And he laid and started rolling on a seemingly featureless spot. It turned out, some diesel fuel had been spilled there.


Yes your last sentence all the way


Yeah his nose doesn't feel anything anymore. But the cameraman had a rough time in that island.


covid related loss of smell perhaps?


Loss of smell due directly inhaling ammonia


You think the chemists were time travelers?


The video was made in December 2022.

But still, the covid hypothesis seems extremely farfetched. Desensitization from exposure I could believe.


Oops, thought GP's reply was to another comment.


And of course, since selenium compounds are said to smell even worse...

https://www.youtube.com/watch?v=031vrZAMEHU


I did some lab work on selenium a long while back.

The worst was when a reaction overheated and the chemicals decomposed.

The smell was truly revolting. It reminded me of skunk, burnt rubber tires and sewer.


Selenium stinks alright


The moment I saw that I knew I had to reproduce that. Turns out you can just buy all the required stuff.


Ugh okay I’m gonna try to buy some from him and see what it smells like.


Lol I knew before clicking it would be NileRed.


I didn't really like chemistry in school, but NileRed makes me wish it was different. Great guy!


Awesome. Although it's a pretty small lake. In the video he shows a map and mentions there were some houses 200m downwind.


If you're interested in other terrifying compounds be sure to read 'Ignition'.[0]

My footnote is for a scan of the original printing but I believe the book has have recently been reprinted in multiple formats. Regardless of the format you choose, it's a hell of a read.

[0] https://library.sciencemadness.org/library/books/ignition.pd...


I've tried to read it, and while I can see it's an entertaining read, at the same time it reads like a long string of chemical compounds and formulas being read. I'd only recommend it if you have a better grasp of and interest in chemistry than I have.


From my recollection (I haven't re-read it recently), it's pretty easy to skip the raw chem stuff if you're not interested.

Though that may be a skill I acquired from my youth misspent reading Alexandre Dumas and Jules Vernes (as writers of serials, padding chapters was a very common occurrence which makes for frustrating reads when you hit 5 pages of fishes in 20000 leagues under, the ability to quickly skim and skip is necessary to reach the end).


I agree. I muddled through it because the non-technical 25% made it worthwhile and the writing was very nice.


If this is your first time reading one of these, Derek Lowe’s “things I won’t work with” series is a great way to spend a Saturday afternoon.


FOOF is my favorite. Come for an analysis of Streng's papers and stay for Satan's kimchee.


I first read https://www.science.org/content/blog-post/sand-won-t-save-yo... so I will always have a soft spot for it.

"[...] it can potentially go on to “burn” things that you would normally consider already burnt to hell and gone, and a practical consequence of that is that it’ll start roaring reactions with things like bricks and asbestos tile."


If you keep researching, it’s a fun rabbit hole of the Internet to go down. The Material Safety Data Sheet from one of the few(!) manufacturers is… something else.

The MSDS warnings for ClF3 read like the State Department travel advisory warnings for Bhakmut.


That was my introduction to the series, too - certainly a classic! (I have a vague recollection that it was linked to from DansData at some point, but couldn't swear to it.)


At seven hundred freaking degrees, fluorine starts to dissociate into monoatomic radicals, thereby losing its gentle and forgiving nature.

Referring to fluorine’s “gentle and forgiving nature” got a good laugh out of my wife, who has a chemistry degree. It also got me a good education about just how gross elemental fluorine is.



Love his writing so much. Always entertaining and informative.

> This stuff was first prepared in Germany in 1932 by Ruff and Menzel, who must have been likely lads indeed, because it's not like people didn't respect fluorine back then.


F is for Flags, they be of red.



Thank you for this link! Always wanted to read the whole collection.


Anyone thinking this might have potential as an unconventional weapon might find it interesting to read Neal Stephenson's Zodiac. The protagonist, a chemist-turned-environmental-activist, makes some Putrescine (a similarly stinky substance) for self defence.


Putrescine and cadaverine actually smell just like... Semen. Gross, overwhelming splooge. But not particularly incapacitating or vomit-inducing, looks like Neal didn't do his research.

Bradford pears also smell similar, though tending a bit more fishy.

(Grad school, a project next door involved making a whole library of polyamine derived chemical probes, so we got basically all the flavor notes of semen in succession. The lols outweighed the unpleasantness.)


How are smells transferred and detected far away after a few seconds when the air is not moving that fast?


They aren't. The air is moving that fast.


A quarter mile in seconds? That’s brisk!

More likely, I guess, that the distance was up to a quarter mile and the time was as low as seconds, but for different observers at different distances.


The velocity of an average air molecule at normal atmospheric pressure is about 1000 mph, so yes - brisk indeed. Of course the mean free path is only a few dozen nanometers, so it'll take about 10^10 collisions before a molecule reaches that far - but they started with "a drop", or something like 10^21 molecules, so statistically there's plenty of opportunity for a few "lucky" molecules to make it - and it's so stinky that we can detect it even in those absurdly low concentrations.


Thanks for the answer, what terms should I be googling to get more info?


Is this the stuff they use in legal pepperspray alternatives (in places where pepperspray is not legal)?


Not that I'm aware of.

It would be classed the same as pepper spray in the UK (a "noxious chemical").

The skunk lock and similar products that use a malodorous chemical are illegal in the UK for this reason.

There are "self defense sprays" sold in the UK and some other countries that just contain a dye, no irritant or malodorous substance, but even those are legally questionable at best - just there's been no case law yet that I'm aware of.


That all seems a bit excessive doesn't it? Does that mean you can't carry a pocket knife either? I would be lost without my Leatherman or at least a swiss army knife.


Yes, it is excessive.

The UK is highly restrictive, in so many ways.

As for knives in the UK: so long as the blades under 3 inches long, and it is a non locking folding knife, it is legal to carry in public (with some exceptions).

Any knife longer than 3 inches, or any knife with a locking blade, cannot be carried unless you have a good reason (eg: going to/from work, etc).

You likely will have to argue this reason in court if the police officer is a cunt, and most of them are cunts when it comes to having common sense around blades.

Fixed blade knifes of any length require a "good reason" to carry.

A lot of coppers in the UK are ignorant as fuck too, and will confiscate your folding, non locking, sub-3 inch Swiss army knife requiring you to jump through burning hoops, wade through an ocean of piss, and sacrifice a virgin goat at midsummar to get it back.


At the other end of the spectrum my kid can walk around with a machete and be perfectly legal, but her school library can't have V for vendetta. Is there anywhere that doesn't nanny about access to ideas or "weapons" (I'd rather use an umbrella as a weapon than a Leatherman if it came to it).


I have no idea if anywhere exists that doesn't have some nanny state bullshit going on.


In defence of the police officers, you are probably dealing with similar level of anxiety as soldiers. I imagine a high number of them have had to deal with a knife incident and just because you’ve got a taser, some training and some backup doesn’t necessarily mean it’s going to end well for you. There are quite a few reports of people (especially large blokes like rugby players) who can shrug off a taser and go on a rampage. It famously took 20 police officers to arrest Eddie Hall and that was before he became a professional strongman.

I’ve heard the expression “don’t go into a knife fight and expect to come out uncut”. As in, even if you win, there’s a high likelihood you’re going to have slash wounds on some part of your body somewhere. Yes a bit of common sense should be in order but I can also understand why they want to be very strict about these things. Having to deal with a knife fight and the aftermath probably isn’t a great day at work.


> cannot be carried unless you have a good reason (eg: going to/from work, etc).

Sounds like you can easily get around any problems by just saying you are heading for work.


The problem is, if the officer doesn't believe your reason is good enough, you end up having to go to court over it - which is expensive, and you may well lose and catch a custodial sentence.

I can't really overstate how ridiculous the UK's laws around knives are.

Even tradesmen with glaringly obviously valid reasons to carry knives are recommended to lock them securely in a toolbox while not at the jobsite to avoid prosecution.


Perhaps wrap it in gift-paper then :)


Most likely not.


More likely to be methyl mercaptan as that is frequently used as an odorant and is available from chemical suppliers.


For a not-all-that-fun time, go to eBay and search on that.

there was one answer, and it was for a prank device to detect that.

Plus I got a box inviting me to select the vehicle type this was for. I took one, and got a lot of miscellaneous stuff having nothing to do with thioacetone.


(2009)


Relevant? Not sure noses have evolved much in 14 years :)


Speak for yourself. I’ve had two kids in that time.


It's required for submissions older than the current year. It's not in the guidelines as far as I know, but people will complain (rightly in most cases) and the headline will magically change to include it.


My impression is people complain only if it's news that ages, this isn't.

---

"Romani Invadest Albion!"

> Please add 40BC to the title

^^ like that


I saw the submission before the year was added, I was excited that it might be a new post by the author.


How many Romans?


Sounds like a possible weapon. Not fatal or toxic but certain to temporarily disable troups downwind.


Aaand you’ve just hit the problem with chemical weapons.

Wind shifts.

Before you know it your own troops are vomiting and choking on their uvulas.


I'm a little disappointed by this article. After all, I'm sure the author knows that anything that stinks with sulfur can be made stinkier by substituting selenium! Selenoacetone is worse than thioacetone!

https://www.youtube.com/watch?v=031vrZAMEHU


PSYOPS potential?




Guidelines | FAQ | Lists | API | Security | Legal | Apply to YC | Contact

Search: