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Poll: worst stench
Mercaptoethanol --- 7 (21.88%)
Butyric acid --- 7 (21.88%)
Other --- 18 (56.25%)

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[*] posted on 9-4-2008 at 12:40
worst stench


I would like to know which compound has the worst smell.
I was doubting between the following.
If you know a compound that smells far more then the ones listed below please let me know.
Preferably a smell that lasts really long.
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[*] posted on 9-4-2008 at 12:46


According to the Guiness book of records, ethanethiol (ethyl mercaptan) is the smelliest substance in existence. I am happy not to have smelled this substance, and to quote the book: "It has an ooze like a mixture of rotten cabbage, garlic, onion, burnt toast and sewer- gas. "

In my personal experience, Hydrogen Sulfide is the worst of the ones I have smelled.




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[*] posted on 9-4-2008 at 12:55


I have heard the hydrogen sulfide has the lowest scent threshhold.



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[*] posted on 9-4-2008 at 12:55


http://www.sciencemadness.org/talk/viewthread.php?tid=1216&a...

happy wafting!

O3




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[*] posted on 9-4-2008 at 14:01


Pyridine is the worst stuff I have ever had the pleasure of sniffing.



Not all chemicals are bad. Without chemicals such as hydrogen and oxygen, for example, there would be no way to make water, a vital ingredient in beer.
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[*] posted on 9-4-2008 at 15:48


Some time ago I was heavy into esters. I bought some butyric acid to experiment with and when I opened it my rather sensitive stomach kicked in..... I eventually made the ester and I lost a few lbs in the process.

Joe
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[*] posted on 9-4-2008 at 19:58


I had spilled the butyric acid in the stockroom where I worked and cleaned it up. I hitchhiked home; got a ride. The guy didn't kick me out or even say anything until I told him what had happened. He said he was glad it wasn't he. I guess he had worried about that and was relieved to know. There's a suite of mercaptans that come out of paper mills that I find intolerable; particularly if the trees are pines. It feels like an allergy or chemical sensitivity of some kind.



[Edited on 9-4-2008 by chemrox]




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[*] posted on 9-4-2008 at 21:13


What about H2Se, CH3CH2SeH, and other selenomercaptans? I am sure that they would be even smellier than the corresponding sulfur compounds, and more poisonous.

Butyric acid? Do you mean the n-isomer? I wonder if substituted butyric acids, or the other isomers, could be even worse. And what about thiobutyric acid?
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[*] posted on 9-4-2008 at 22:28


Supposedly, 3-methylbutylaldehyde smells like cheese, but I can't find much on it. The other day, a student in lab was messing with something quite cheesy. I think an intermediate was something like, umm 3-nitro-phthalazide might be possibly the right name, in any case I recall it was nitrophthalic acid condensed with hydrazine (which is then similar to the phthalimide I cooked up a few weeks ago).

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[*] posted on 10-4-2008 at 09:50


Of several thiols I have known and loved (MeSH, EtSH, PrSH, AllSH, t-BuSH, PhCH2SH, PhCH2CH2SH, HOCH2CH2SH, HSCH2CH2SH, PhSH and 4-MeOPhSH), phenethyl mercaptan was by far the worst smelling one. After it got absorbed, say, by a piece of a polyethylene tubing, the stench may remain there for years.
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[*] posted on 10-4-2008 at 10:06


Some organic amines are pretty repulsive, trimethylamine, cadaverine etc....


edited to add the Some bit, not all organic amines smell bad.



[Edited on 10-4-2008 by YT2095]




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[*] posted on 10-4-2008 at 11:35


I never found butyric acid to smell that bad. It's bad but the smell is so strong that it just starts to get an acetic acid type "feeling" to it. Like the horrible smell subsides and it it just smells "chemically".

I don't know what ethanethiol smells like so...

Niether for me... NO2 is the worst IMO.




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[*] posted on 10-4-2008 at 12:45


Quote:
Originally posted by 12AX7
Supposedly, 3-methylbutylaldehyde smells like cheese, but I can't find much on it. The other day, a student in lab was messing with something quite cheesy. I think an intermediate was something like, umm 3-nitro-phthalazide might be possibly the right name, in any case I recall it was nitrophthalic acid condensed with hydrazine (which is then similar to the phthalimide I cooked up a few weeks ago).

Tim


He'd be making luminol unless I'm mistaken. You then reduce the nitro group to an amine and you're done. This is a synthesis I've been wanting to do.

H2S doesn't really bother me, even though I'm aware of its potency...Neither does ammonia. I've never had a jar of butyric acid in front of me, but I have waded through ginko fruit for the edible nuts contained in them. The fruit have lot of butyric and caproic acid and rather enjoyed the smell. I relate it to cheese, not vomit. My roomate was going to throw up standing 10 feet away...

[Edited on 4-10-08 by UnintentionalChaos]




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[*] posted on 10-4-2008 at 12:52


Quote:
Originally posted by MagicJigPipe

Niether for me... NO2 is the worst IMO.


This may sound strange to a lot of people, but I find the smell of NO2 kind of sweet...:P




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[*] posted on 10-4-2008 at 16:43


Quote:
Originally posted by UnintentionalChaos
I've never had a jar of butyric acid in front of me, but I have waded through ginko fruit for the edible nuts contained in them. The fruit have lot of butyric and caproic acid and rather enjoyed the smell. I relate it to cheese, not vomit. My roomate was going to throw up standing 10 feet away...


Omg. I find gingko nuts REVOLTING. The street next to me is lined with gingko trees and it always smells like vomit. If I want to eat gingko nuts, I just buy them pre-packaged and smell-free at the store :D

Br2 is disgusting too. It smells like rotting sewage mixed with metal and chlorine (*barf*). I nearly threw up when I caught a whiff of an unexpected cloud :(



[Edited on 4/11/2008 by Saerynide]




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[*] posted on 10-4-2008 at 17:15


Quote:

This may sound strange to a lot of people, but I find the smell of NO2 kind of sweet...:P


I certainly don't find it sweet but I kind of like the smell in low concentrations...

I hate sulfur dioxide when inhaled but like the aroma I also hate chlorine. Like the smell of dextrin, xylene, mononitroxylene acetone etc and "metallic odors"

Mononitroxylene smells so good I want to drink a whole bottle of it I tasted it once it tastes minty with a twinge of alcohol and something else (spicy?)

[Edited on 10-4-2008 by crazyboy]




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[*] posted on 11-4-2008 at 00:05


Vitus says:

Quote:
Originally posted by Vitus_Verdegast
I have it on good authority that 1,3,5-tris(isopropyl)hexahydro-1,3,5-triazine, the condensation product of formaldehyde and isopropylamine, smells exactly like human semen.

I can easily imagine the possibilities of a combination of an aqueous suspension of the former, some microcrystalline cellulose, a 10 liter bucket and a certain local embassy building.. :D


I've got paraformaldehyde; all I'll need now is the amine... :D

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[*] posted on 11-4-2008 at 04:48


Quote:
25.0 ml (294 mmol) of isopropylamine was dissolved in 75 ml of toluene. 28.6 g (352 mmol) of 37percent aqueous formaldehyde solution was added thereto under ice-cooling. After stirring at room temperature for 20 hrs, the reaction solution was washed twice with 125 ml of water. The solution was dried over anhydrous magnesium sulfate, and concentrated under reduce pressure to give 18.87 g. (88.43 mmol) of. 1,3,5-triisopropylhexahydro-1,3,5-triazine as colorless liquid.

This seems like a bad yield.
I also found another article with a 66% yield.
This is the one below
Quote:
General Procedure of 1,3,5-tris-alkylhexahydrotriazine synthesis. The tris-alkyltriazines were prepared by
treatment of the alkylamines with 37% aqueous solution of formaldehyde in a I:1.3 ratio, by 12 h at 0°C 3. The
mixture reaction was extracted with CHzCI2 and the organic layer was separated, dried over NaOH, and
concentrated under vacuum. ( 1:1 ).
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[*] posted on 11-4-2008 at 07:01


I was working with some pentanol once. I thought it would be fine but it stank a bit like sick (a bit like butanoic acid).. Could it have oxidised in part to pentanoic acid? Would this have made that customary sickly smell?


I also hate pyridine!

[Edited on by DrP]
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[*] posted on 11-4-2008 at 12:50


"Could it have oxidised in part to pentanoic acid?"

Most certainly. It's supposed to smell like dirty socks. Gross!




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[*] posted on 11-4-2008 at 12:54


Kumada couplings with thiophenes produce some kind of black, nearly insoluble goo which has an absolutely repulsive smell. It'll persist for days on end and must be destroyed with bleach or permanganate.



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[*] posted on 11-4-2008 at 13:21


I just received some pyridine, which I ordered a week ago. It has a bad smell, but it is not as outrageous as some people describe. There are many other things, which I find more repulsive.

Strangely, the smell of Cl2, Br2, NH3, SO2, NOCl and NO2 is not bad to me, as long as they are not pungent. Some people say that Br2 has a horrible smell. To me, this smell is neutral (but very distinct and I can smell it exceptionally well). Strangely, almost all simple inorganic compounds which are very smelly, I do not really dislike. I think, the worst of the simple inorganic common smells is H2S, but even that is not so bad to me, that it makes me feel sick.

The smells, which I really dislike are CS2 (after some time, when it is exposed to air and humidity for some time) and some organic compounds (e.g. acetone, to which sulphur and NaOH is added). The smell of aniline, mixed with CHCl3 and NaOH also is very repulsive.

One compound, which makes me upset very much is HN3 (fast heartbeat, feeling of fear). Unfortunately, I cannot smell HCN and that is very dangerous. So, I do not do experiments with cyanides, or with reactions, where cyanides could be formed, at least not in more than 10's of mg quantities.




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[*] posted on 12-4-2008 at 10:48


Referring to the stench of mercaptans from paper processing, I don't know how many of the active ingredients were mercaptans, but when we drove past a paper mill in Sweden years ago, the stench shook even an old lab-hound like myself. Our sons were small at the time and burst into tears in sheer rage at the asault. I assume it used the sulphite process in use, but certainly the smell suggested mercaptans rather than oxidised sulphur.

For my money mercaptans are not too bad, in that one quickly adapts to them. I made some in my student days (extra-curricularly) and was left in doubt whether they were bad at all. I made a few kinds, mainly butyl and allyl, to see which smelt worst, and the butyl smelt not much worse than scorched rubber, so I asked a woman to comment on the smell of an empty test tube in which I had had a few drops. She practically did a back somersault and later told me that she could not get the smell out of her nostrils till she woke up next day. Honestly, I had had no such intention!

Anyway, methane thiol is a component of sea smell, so, between that and my experience with other thiols, I am mildly sceptical about the ethanethiol record. H2S is hardly worth consideration as a pong. One gets used to it in no time.

The reason for messing with butyl was that the received wisdom was that butyl mercaptan was skunk smell. However, I have learned since that this is not strictly correct. Skunk smell contains a cocktail of components, not all of them produced directly by the skunk. The rest are microbial metabolites, so that the results are not particularly constant. Thereby hangs another tale, but of more relevance to biologists than chemists.

Allyl mercaptan was worse, with a nasty garlicky smell, but that too I rapidly became used to, so much so that when I added a few drops of peroxide to see whether that would give me the dithioether, the smell of garlick nearly knocked me over, smelling worse than the mercaptan imo at the time.

Oh yes, these oily substances do have the habit of diffusing into rubber and the like, as Caribou mentioned. Some of my product impregnated a rubber bung. I had occasion to bore a hole through it about a year later, not having had anything to do with mercaptans in between, and when I extracted the cork bore, I was shocked at the stench!

Saerynide might like to reflect that the name Bromine comes from Greek for “stench”.

Apparently a particularly persistent smell is trichloroanisole. If I have this right (never played with it myself) there have been warnings published against preparing the substance, since one cannot get the smell out of the lab for months. Skatole and related indole derivaties also are particularly offensive, smelling of ordure, and some of them are persistent.. Any students reading this, be warned! It would be a good way of ruining your career, not only as a student, to cause a snafu with such materials.

Some smells are less intense than others, but more revolting in higher concentrations: organic isocyanides are one example. Pyridine is another.

Use your good sense and never play around with such materials in more than semi-micro quantities!

Cheers,

JG
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[*] posted on 13-4-2008 at 00:27


The triazine referred to above is an intermediate in the synthesis of N-methylisopropylamine from Rhodium:
http://www.erowid.org/archive/rhodium/chemistry/isopropylmet...




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[*] posted on 13-4-2008 at 19:13


I kind of agree with woelen that the inorganic compounds don't really have too nasty of a smell to me. They smell bad, but they smell "I'm going to throw up" bad. It's the organic ones that really get me. Amyl Alcohol, Methyl Mercaptan, and putrecine are three that literally make me sick.

Nitroglycerin is kind of nasty to me only because of the massive headache I know I'll have after getting a whiff of it. So it's more of an association stench than an actual stench.




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