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Things I Won't Work With: Dioxygen Difluoride (corante.com)
257 points by hythloday on April 14, 2013 | hide | past | favorite | 59 comments



Actually I worked as a synthetic organic chemist in a previous life and I was always much more afraid of the chronic systemic poisons than the things that blew up. It's one thing to have something go boom in your fume hood and quite another to get a drop of something on your glove that you don't even notice and then later that week all your hair starts falling out and everything tastes like metal. Organo-selenium, tin and tellurium compounds are particularly nasty.

I'm much happier now with nothing more serious than RSI to worry about.


I used to be a Chemical Engineer. Though I loved the field and science, my job in College as at a uranium processing plant really encouraged me to find work in something else. There were countless really dangerous things, like the hydrofluoric acid they used to eventually fluorinate the uranium.

We'd carry gas masks with us constantly. I had to wear an acid proof suit in 105 degree heat. Geiger counter checks in and out the door.

I ended up breaking my ankle playing basketball and was forced to stay in a trailer so that my cast wouldn't get contaminated with uranium. Since I couldn't do my regular engineering stuff, I had to program stuff on computers the rest of the summer. Much better :) Changed my life forever.


Chem Eng is one of the harder degrees to actually get, and as fun as computers are, I sometimes contemplate going back and getting the Chem Eng degree (I did Comp Eng/Chemistry double) to play with big chemistry.


Yeah, it was insanely tough. Countless all nighters, and impossible problems. What I'm really thankful for is how much pursuing the degree taught me about grit and perseverance to study and overcome problems.


a drop of something on your glove that you don't even notice and then later that week all your hair starts falling out

Anyone who doubts this can happen should read about Karen Wetterhahn [1], who was killed in 1996 by a couple of drops of dimethylmercury that went through her glove. Another nasty chemical to avoid.

[1]http://en.m.wikipedia.org/wiki/Karen_Wetterhahn


Organometallic reagents like dimethyl mercury have their own entry in the same series of blog posts as the OP, cf. http://pipeline.corante.com/archives/2009/10/23/things_i_won...


Why do some dimethyl compounds penetrate the skin so easily? Dimethylsulfoxide (DMSO) will even carry various other compounds into the body as well.


DMSO ((CH3)2SO) is a polar aprotic molecule, which means it's neutral _and_ polar. It's easier for a small, neutral polar molecule like DMSO to pass through the phospholipid bilayer of your cells than it is for acetate (CH3COO-).

The "dimethyl" is not what it's important.


My O-Chem teacher had told my about how people who would dissolve hash oil into DMSO to get it across the skin quickly. Usually on their heads.


That's terrifying...


I never made it beyond a college lab, but one of the things that worried me most (and that, more generally, continues to worry me in life) was a screw-up or deliberate maliciousness on the part of others in the workspace.

I recall one time happening to see two other students applying solutions to the faucets handles of one of the lab desk sinks after a lab, because they thought it would be a funny prank upon whoever next used that sink.

Other times, stuff gets spilled by people who don't know better, don't understand the resulting risk, and/or just don't care enough to "do the right thing". And so inadequate cleanup leaves traces for others to stumble through, likely with know knowledge of the problem.

In my subsequent life, outside of a lab, I've repeatedly encountered significant health risks created by as well as ignored and/or abandoned by people who "don't know" or "don't care".

In broader life, buildings are full of lead, asbestos, and everything else, and putative penalties aside, it's basically "buyer beware" as far as inheriting someone else's problem (inheriting to your own personal liability and financial risk, not to mention possible health risks).

As much as "stuff I won't work with", I've developed an attitude of "people I won't work with".


The stuff you really have to worry about is the stuff you don't know is toxic.

There is a chemical compound called MPTP. It's directly toxic to dopamine neurons. They only discovered it when an underground chemist accidentally made it when try to synthesize a synthetic heroin (for lack of a better term).

I remember a chemist on the East Coast went back and looked at the structure and realized the stuff he had be working on had that active core. He had worked on it for 5+ years.

The problem is, you don't get symptoms of Parkinson's unless you've lost close to 80% of your neurons. I'm sure that East Coast chemist is dam near guaranteed to get Parkinson's at an early age.


It's true. If you're doing research you're probably working with compounds nobody's ever made before so you can't be sure what their biological properties are. You can often make an educated guess by looking at the structure but you can never be sure.


I was also a synthetic organic chemist (but then dropped out of grad school and used my student loan to teach myself to program). The worst thing was you couldn't control what your lab mates were doing and releasing into the air. And you had no idea if what you were breathing in was something horrible and toxic. God I'm glad I got out of that life. Leaving chemistry for programming was the greatest decision of my life.


They didn't work in fume hoods?


They did, but fume hoods never contain everything. Also, people are quite often transferring stuff from hoods to rotary evaporators, etc.


I count three comments on this page (so far) from ex-chemists who are glad to have that world behind them. I never knew it was so dangerous!


Selection bias. The ones still doing chemistry and not code (i.e. Most of them) aren't on HN but working at a place with a decent safety culture.


Haha.. chemical engineer here... and my work is computational. Although I have used HF to prepare wafers before.


Or they work with stuff that's neither explosive nor poisonous.


Yes. My computer has never been unsafe or exploded. Minor fires, electric shocks and toxic smoke yes, and worst of all, cuts from the case while trying to connect cables or replace fans.


Perhaps but the main thing was that within 15 minutes of a story hitting HN three people had mentioned the same reasons for leaving.


Do you understand what 'selection bias' means?


Yes, re-read my original comment: do you really think I am drawing a conclusion about an entire field from three anecdotes on HN, or that maybe the "dangerous" comment was me being light hearted? I just thought it was odd that in such a short space the same thing was cited multiple times, nothing more.


Always worth a reread for the combination of gripping content with good writing. Just to pick another one in this series: http://pipeline.corante.com/archives/2008/02/26/sand_wont_sa... (about stuff that will burn sand (not: burn _in_ sand)


"...every-man-for-himself exotherm..."

Excellent, absolute hoot. I've only had to use hydroflouric acid once (leather apron, double gloves, goggles, fan on) and that was enough...


So it's a no on preparing some in your pressure cooker?

http://what-if.xkcd.com/40/


I'm fairly confident that comic is the reason this thread's article is getting a bunch of attention now.


I'd never before seen the xkcd what-if site. Totally engrossing.


Here is the last discussion on this post, 3 years ago. There may be relevant comments there: https://news.ycombinator.com/item?id=1148425

(although it looks as though the link has changed to the main archive on this site, but all the comments and post title refer to this article. Odd.)


I loved this quote from http://pipeline.corante.com/archives/2011/11/11/things_i_won...

Synthesizing polynitro compounds is no chocolate fondue party, either: if you picture a bunch of guys wheeling around drums of fuming nitric acid while singing the Anvil Chorus from Il Trovatore, you're not that far off the mark. You really have to beat the crap out of a molecule to get that many nitro groups on it, which means prolonged heating of things that you'd really rather not heat up at all.


Derek Lowe has real high class humor. I always end up knowing new things while laughing like a maniac. It just makes things a little awkward at office though. I always had to keep watching over my shoulder just so that no one would notice that I was reading things which can blow up with explosive power which will make TNT feel like baby powder and laughing like a maniac :)


http://pipeline.corante.com/archives/things_i_wont_work_with...

The other articles in that category are mostly equally exciting.


So much stuff like this in Chemistry. It's why I gave up on my Chemistry career and went into programming. When computers blow up, they don't destroy the building or make you change color.


I've often wondered about the correlation. I went pretty far with chemistry in school, seemed oddly good at it, but fell back on programming.


Unless you are programming drones with missiles.


Then it's supposed to blow up.


It's many days since I laughed so much. Especially "If the paper weren't laid out in complete grammatical sentences and published in JACS, you'd swear it was the work of a violent lunatic."


I passed this link to my dad, who actually spent a good chunk of his professional career working with fluorine compounds. His comment: "The guy is just chicken -- or ill-equipped for fluorine work."


Seriously considered naming my band "Satan's Kimchi"


that's what a top poster on the article's comments said


So this is like 10x worse than plain Fluorine [1], which is already evil?

[1] http://www.youtube.com/watch?v=vtWp45Eewtw


And this is why I'm happy to be working on computers now, and not in a wet lab. And I never even had to work with any of the scary stuff...


After reading about the risk in the work of a chemist , i wonder: what prevents automation for safety becoming common place?


Production can be (and often is) heavily automated, research is not. Just like any other field, it doesn't make sense to design robots to do a task requiring high precision that might only need to be preformed a few times. Thats what lab assistants are for.


Does anyone have a link to the original paper that doesn't require me to pay $38?


Not necessarily for this specific paper, but in general if you want a paywall protected paper, check your local public library's website. Most offer proxy database access.


I've got access - I've e-mailed you a copy.


Did anyone else find this article to be meandering waffle that has no bearing to anything else on HN? I fear the airplane toilet incident has inspired a host of chemists to start posting on hacker news, creating a subculture.

And yes, I'm totally expecting someone to point to the HN posting guidelines that state that anything that may be of interest to geeks is appropriate...


I won't point you to the HN posting guidelines since you obviously know where to find them but with 11 karma I think you should work a bit harder to show by example rather than by voicing your dissent what you feel HN should be like.


To be fair, the comment was downvoted, which I accept, but if you disagree with something it's perfectly valid to voice that disagreement. If Karma is a measure of the validity of an opinion, HN becomes a meritocracy.


Here's the deal. You don't have to agree with the community that this is proper for this community. However, you also don't have to participate. You could just as easily not read the article and move on. Or upon discovering you don't think it's a good article, stop reading in the middle and move on. The time spent on complaining could be put to better use, like advancing the state of text mining systems and creating yourself an automatic curator that finds you only articles you like.

I for one like that these articles get through. This particular one won't get me into chemistry, but it was a fun read, and now I know something I didn't know before. But there are other articles that have been "tangential" that opened new doors for me. Sometimes I don't know there is something out there, and others tell me about it, e.g. through this site. That is useful to me. Pure pull is not the way to expand my knowledge.

And if you're doubtful about how tangential information can be door opening... here is a story about this week: I am currently ramping up on a research project about clock synchronization and security for it. A lot of synchronization systems rely on GPS and this is shown to be spoofable, so we're examining security for those clocks, particularly in geographically dispersed systems. Some guy I was chatting with at happy hour does research in remote sensing in the ionosphere, and was telling me about certain characteristics that the ionosphere imparts to signals from satellites. I had no idea of this, but together we worked out an interesting collaboration on a "tangential" bit of work - using the electron density on the transmission path to help authenticate signals. Probably it's good that I did curiosity and learning about off-topic stuff, rather than say "ooh, cool, I'm do some security stuff" and move on.


> If Karma is a measure of the validity of an opinion, HN becomes a meritocracy.

Karma is a measure of time expended.


HN is a bit of a meritocracy. Since you get down-voting power when you hit 500 points (or was it 600)?


500.


Voicing disagreement that a particular submission does not belong on the site is boring. It adds no value, and becomes noise. In this case, we care more about the general discussion than an individual's desire to voice disagreement.


lets discuss ember data issues again. this time we'll have a breakthrough.


Oooh! Or "growth hacking" for consumer startups! That's fertile, unexploited territory.


No, no one else did.




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