Org Prep Daily

August 5, 2008

The scent of tramp

Filed under: lab destruction — milkshake @ 1:47 pm

The grumpy old man from the preceding story (who fired me for stinking up his lab) had himself an accident in his younger years. Here is the story as told and re-told over the years:

The guy was making ethylthioester of acetic acid. While he was working up the reaction mixture and doing the extraction with ether he ineptly released the sep funnel stopcock and the over-pressure sputtered some of the mix on him with a good aim – all over his face and forehead.

So the guy immediately proceeded to wash himself with bleach and soap and alcohol but it hardly helped.  A good thing he was wearing his old working clothes with acid-eaten holes, too (but it must have made him look more like a bum rather than a young faculty). The mishap occured later in the morning on a warm day in May. There is a public bath place with the Olympic-sized swimming pool and sauna located just two tram stops away from the campus – and our guy was a frequent visitor there and he got the brilliant idea that he should go there at once and have a dip to wash off that reek in a pool of chlorinated water.

As soon as he got on a tram all fellow passengers re-positioned themselves towards the opposite end of the tram.  A little boy riding there with his mom said in a sorrowful voice: “Ma – I think this scarry man just pooped himself”.  Few faces lit up. The mom answered, stern and loud – for the benefit of everyone on the tram :”No, Johny, this man did not poop himself. He just needs soap and water – lots of soap, and lots of water.”

Our guy promptly got off at the next stop; he finished the rest on foot. The cashier and the locker room lady gave him strange looks but otherwise the place was almost deserted – it was a business day and morning time. So our guy showered himself and then was swimming back and forth, many laps in that giant pool but the stink was still with him. “No use to swim in the cold water – but volatile organics azeotrop with steam”, he though. He headed to sauna.

It was still early in the day and he had the whole sauna to himself; he was sitting there relaxed and for the first time he felt like the stink was gradually weakening until he could smell it no more. Next, the door opened and another nude dude with a towel sat on a bench across the room. He was apparently some sort of hyperactive fellow – instead of leaning back the new guy kept looking left and right. He got up and looked under the bench, then he walked across the sauna room, looked under other benches too and inspected every corner. Finally he said, perplexed: “It beats me – the shit gotta be here somewhere!”


  1. I’m stunned that the bleach didn’t work. It’s like meeting a grizzly bear and learning it’s going to laugh at your shotgun.

    Comment by Klug — August 5, 2008 @ 1:59 pm

  2. That’s a tough one…unlike phosphines (or thiols, for that matter) that can be oxidized with bleach to something less stinky, mercaptoacetic acid…I’m not quite sure how it would react with hypochlorite.

    So what did the poor soul end up doing to rid his strong cologne?

    Comment by SciChick — August 5, 2008 @ 6:31 pm

  3. I don’t know – I heard hints that the swimming pool stink story did not end there in the sauna but it had a hillarious continuation – which I was not told because I was a freshman, and the details were very inapropriate. Maybe it is not true – one hears all sorts of gossip. I could ask my former phosphine project advisor about the whole story – he is now here in US also. (In fact he inherited my bench and hood at my first employer in Arizona after I left; we missed each other there by few weeks and we never got to work together again – which is probably a lucky coincidence for the company because it stil exists today, and it had never burned down inspite of my alarming lab techniques.)

    Comment by milkshake — August 5, 2008 @ 6:53 pm

  4. If bleach doesn’t work, what next? 10% H2O2?

    Comment by Klug — August 5, 2008 @ 7:06 pm

  5. milkshake another great tale- not sure I can write as still laughing hard. I may have sudden outburst next time I visit a sauna.

    Having had to deal with a dog who got the worse from skunk encounters(2x in 6 month span) we learned a couple things: Do not try to wash off with water, especially soap and water as just will set the smell for days. We did come across the following recipe for deskunker that is effective if used within a hour or so;
    1 quart of 3% hydrogen peroxide
    1/4 cup of baking soda
    1 teaspoon of liquid dish soap

    On large scale typical to use a NaOH/Bleach scubber to capture mercaptains however would not advise for skin.

    Comment by CMC guy — August 5, 2008 @ 11:06 pm

  6. I had a similar experience- reacting hydrazine with S- methyl thiourea …..without an inkling about the resulting stink of mercaptan…..the reaction was continued for 4 hrs without much supervision and ended up in the serious search for a dead rat on the premises……no one knew the cause…..and I certainly didnt enlighten anyone….

    Comment by Megdeg — August 6, 2008 @ 12:41 am

  7. Those who use DMSO as a magic solvent for esterifying hindered alcohols with acid chlorides rediscover the Swern oxidation. It is not a subtle thing.

    Diddling with thiols can often be tamed by using the disulfide instead and reductively cleaving at point of use.

    Sulfur stench should give way to hypochlorite, potassium peroxymonosulfate (e.g., Oxone), or percarbonate as Oxy-Boost, OxyClean…

    Peroxides benefit from transition metal (tungstate is nice, and nephrotoxic) catalysis. Tomato paste mostly neutralizes skunk by thiol addition to conjugated olefins (greatly aided by sunlight!). Adding a shot of Dawn dishwashing liquid is beneficial.

    Comment by Uncle Al — August 6, 2008 @ 1:10 pm

  8. The gem dimethyl derivative of this thioacetic acid ester is described in the literature as an ‘evil smelling liquid’. & it is but not so bad if you keep it cold & bleach everything you use in the hood. The guys at Toronto said they almost got in trouble with the Canadian EPA for making that 20 g of it for us.

    Comment by jc — August 6, 2008 @ 1:47 pm

  9. jc – thank you for reminding me a of story that happened at my first employer in Arizona – I just wrote it up as the next post.

    Comment by milkshake — August 6, 2008 @ 4:40 pm

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