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DNA
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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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ScienceGeek
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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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chemkid
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I have heard the hydrogen sulfide has the lowest scent threshhold.
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Ozone
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http://www.sciencemadness.org/talk/viewthread.php?tid=1216&a...
happy wafting!
O3
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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evil_lurker
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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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joeflsts
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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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chemrox
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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]
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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JohnWW
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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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12AX7
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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
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caribou
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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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YT2095
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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]
\"In a world full of wonders mankind has managed to invent boredom\" - Death
Twinkies don\'t have a shelf life. They have a half-life! -Caine (a friend of mine)
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MagicJigPipe
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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.
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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UnintentionalChaos
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| 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]
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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ScienceGeek
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| 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...
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Saerynide
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| 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...
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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 
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]
"Microsoft reserves the right at all times to monitor communications on the Service and disclose any information Microsoft deems necessary to...
satisfy any applicable law, regulation or legal process"
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crazyboy
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| Quote: |
This may sound strange to a lot of people, but I find the smell of NO2 kind of sweet... |
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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sparkgap
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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.. |
I've got paraformaldehyde; all I'll need now is the amine...
sparky (^_^)
"What's UTFSE? I keep hearing about it, but I can't be arsed to search for the answer..."
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DNA
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| 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.
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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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DrP
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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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MagicJigPipe
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"Could it have oxidised in part to pentanoic acid?"
Most certainly. It's supposed to smell like dirty socks. Gross!
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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vulture
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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.
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
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woelen
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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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JeanGeilland
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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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garage chemist
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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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Jdurg
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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.
\"A real fart is beefy, has a density greater than or equal to the air surrounding it, consists of the unmistakable scent of broccoli, and usually
requires wiping afterwards.\"
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