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Author: Subject: Formamide
itchyfruit
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[*] posted on 22-6-2009 at 11:51
Formamide


Is their any interesting stuff that this stuff can be used for (i do realise it's quite toxic) i just happen to have a big bottle of it that i acquired some time ago when i was trying to find a rubber solvent.
Just some idea on what it's normally used for would be a good start!!
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[*] posted on 22-6-2009 at 12:01


The only interesting use i can think of is decomposition to HCN and water vapour. Even with this yields are low (a lot goes to CO + NH3)

Edited for sp.

[Edited on 22-6-2009 by Saber]
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pHzero
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[*] posted on 22-6-2009 at 12:40


Quote: Originally posted by itchyfruit  
Is their any interesting stuff that this stuff can be used for (i do realise it's quite toxic) i just happen to have a big bottle of it that i acquired some time ago when i was trying to find a rubber solvent.
Just some idea on what it's normally used for would be a good start!!


It'll react with an alkali to form a cyanide salt, but only try that if you're sure you know what you're doing with cyanides and have appropriate safety procedures in place to handle them.
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itchyfruit
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[*] posted on 22-6-2009 at 12:58


I don't have the faintest idea how to handle or know what to do with a cyanide salt. Is that all it's used for? i was hoping it would turn bright blue or something :(
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pHzero
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[*] posted on 22-6-2009 at 13:04


Quote: Originally posted by itchyfruit  
I don't have the faintest idea how to handle or know what to do with a cyanide salt. Is that all it's used for? i was hoping it would turn bright blue or something :(

Aha, the name does suggest that, doesnt it? Actually thats where the name "cyanide" came from - ferric ferricyanide (prussian blue) is a deep blue pigment, used in blueprints.
But nah, cyanide salts are generally colourless, and extremely toxic - the nazi party used hydrogen cyanide (made by acidifying potassium cyanide) in gas chambers. Cyanides are one of only two chemicals I know of which can dissolve gold, the other being aqua regia. It isn't corrosive though - you could stick your finger in a solution of cyanide and it wouldnt burn it away or anything but I expect it'd sting if you got it on a cut. (You would probably die of cyanide poisoning less than an hour later though, its readily absorbed by skin contact)
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pHzero
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[*] posted on 22-6-2009 at 13:13


Oh here's another thing you can do with your formamide: add dilute H2SO4 to it, and you get formic acid and ammonium sulfate
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[*] posted on 22-6-2009 at 13:14


Quote: Originally posted by pHzero  
Quote: Originally posted by itchyfruit  
I don't have the faintest idea how to handle or know what to do with a cyanide salt. Is that all it's used for? i was hoping it would turn bright blue or something :(

Aha, the name does suggest that, doesnt it? Actually thats where the name "cyanide" came from - ferric ferricyanide (prussian blue) is a deep blue pigment, used in blueprints.
But nah, cyanide salts are generally colourless, and extremely toxic - the nazi party used hydrogen cyanide (made by acidifying potassium cyanide) in gas chambers. Cyanides are one of only two chemicals I know of which can dissolve gold, the other being aqua regia. It isn't corrosive though - you could stick your finger in a solution of cyanide and it wouldnt burn it away or anything but I expect it'd sting if you got it on a cut. (You would probably die of cyanide poisoning less than an hour later though, its readily absorbed by skin contact)


Aqua regia isn't a chemical :p

Halogens happily attack gold, especially in aqueous solution.
Thiosulfate (I think) will also attack gold like cyanide in the presence of oxygen, owing to the formation of soluble gold thiosulfato complexes.




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pHzero
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[*] posted on 22-6-2009 at 13:18


Quote: Originally posted by UnintentionalChaos  


Aqua regia isn't a chemical :p

Point taken. It's a mixture, but you can think of it as the chemical nitrosyl chloride, since thats the corrosive part of it, isnt it?

Quote:
Halogens happily attack gold, especially in aqueous solution.
Thiosulfate (I think) will also attack gold like cyanide in the presence of oxygen, owing to the formation of soluble gold thiosulfato complexes.

Ah right, never knew that. I thought you could only make gold halides from nitrosyl halide. Well, you learn something new every day :)


[Edited on 22-6-2009 by pHzero]
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UnintentionalChaos
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[*] posted on 22-6-2009 at 13:26


Quote: Originally posted by pHzero  
Quote: Originally posted by UnintentionalChaos  


Aqua regia isn't a chemical :p

Point taken. It's a mixture, but you can think of it as the chemical nitrosyl chloride, since thats the corrosive part of it, isnt it?

Quote:
Halogens happily attack gold, especially in aqueous solution.
Thiosulfate (I think) will also attack gold like cyanide in the presence of oxygen, owing to the formation of soluble gold thiosulfato complexes.

Ah right, never knew that. I thought you could only make gold halides from nitrosyl halide. Well, you learn something new every day :)


[Edited on 22-6-2009 by pHzero]


I believe that NOCl is a byproduct of the reaction mixture, which generates, among other things, chlorine gas. It's rather messy, but I believe that a large part of it is tandem oxidation and complexing by nitrate and chloride respectively.

If anyone would know, it's fleaker.




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'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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[*] posted on 22-6-2009 at 13:32


Quote: Originally posted by pHzero  
Oh here's another thing you can do with your formamide: add dilute H2SO4 to it, and you get formic acid and ammonium sulfate


This sounds interesting (as i happen to have quite an excess of h2so4 aswell) and no ammonium sulphate of formic acid!! is it possible to separate them? formic acid = ant sting/kettle descaler am i correct?I haven't got a barny about ammonium sulphate thou:)
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setback
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[*] posted on 22-6-2009 at 13:38


Cyanide forums a soluble complex with gold, there's some controversy concerning it's use. It's better than mercury though.

You also do not want to allow a solution of cyanide to become acidic. It will form deadly HCN gas.

[Edited on 22-6-2009 by setback]
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Lambda-Eyde
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[*] posted on 22-6-2009 at 13:38


Distillation, perhaps?

Watch out with that H2SO4. Sulfuric acid and formic acid react to give carbon monoxide, which is highly toxic and undetectable.
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pHzero
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[*] posted on 22-6-2009 at 13:39


Quote: Originally posted by itchyfruit  
Quote: Originally posted by pHzero  
Oh here's another thing you can do with your formamide: add dilute H2SO4 to it, and you get formic acid and ammonium sulfate


This sounds interesting (as i happen to have quite an excess of h2so4 aswell) and no ammonium sulphate of formic acid!! is it possible to separate them? formic acid = ant sting/kettle descaler am i correct?I haven't got a barny about ammonium sulphate thou:)

Yep, thats true
Got a distillation still? You can boil off the formic acid, leaving behind the ammonium sulfate.
I dont know what you can use formic acid for though, other than making carbon monoxide. I wouldnt recommend descaling your kettle with it, since its one of the metabolites of methanol (black market adulterated alcohol) which turns you blind: use vinegar or citric acid instead :D
You can use the ammonium sulfate to make ammonia by reacting it with sodium/potassium hydroxide, I think (be careful working with NH3, NaOH or KOH though, they're rather corrosive)
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[*] posted on 22-6-2009 at 13:48


Itchy, please do not mix sulfuric acid and formamide.....you seriously risk killing yourself and anyone near with carbon monoxide....:o


And possibly cyanide gas as well! :o

[Edited on 6-22-2009 by Eclectic]
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pHzero
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[*] posted on 22-6-2009 at 13:53


Quote: Originally posted by Eclectic  
Itchy, please do not mix sulfuric acid and formamide.....you seriously risk killing yourself and anyone near with carbon monoxide....:o


And possibly cyanide gas as well! :o

[Edited on 6-22-2009 by Eclectic]


It wouldnt make HCN with dilute acid would it? At low concentrations, surely the acidic properties would be favoured over the dehydrating properties?
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[*] posted on 22-6-2009 at 13:59


Quote: Originally posted by pHzero  
Quote: Originally posted by itchyfruit  
Is their any interesting stuff that this stuff can be used for (i do realise it's quite toxic) i just happen to have a big bottle of it that i acquired some time ago when i was trying to find a rubber solvent.
Just some idea on what it's normally used for would be a good start!!


It'll react with an alkali to form a cyanide salt, but only try that if you're sure you know what you're doing with cyanides and have appropriate safety procedures in place to handle them.


You make me laugh pHzero. Its like the blind leading the blind. And whats wrong with using formic acid to descale the kettle? You know you're supposed to rinse it out afterwards with water right...
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[*] posted on 22-6-2009 at 14:05


DJF90 you seem to be constantly at pHzero's throat, regardless of what he asks!
Now, when the health and wellbeing of him and people around him are at risk, I see your point. However, here he was just asking a perfectly viable scientific question about dehydrating properties of acids vs. their concentrations. Even if it's a stupid question, at least say so, and give the correct answer.
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pHzero
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[*] posted on 22-6-2009 at 14:06


Quote: Originally posted by DJF90  
Quote: Originally posted by pHzero  
Quote: Originally posted by itchyfruit  
Is their any interesting stuff that this stuff can be used for (i do realise it's quite toxic) i just happen to have a big bottle of it that i acquired some time ago when i was trying to find a rubber solvent.
Just some idea on what it's normally used for would be a good start!!


It'll react with an alkali to form a cyanide salt, but only try that if you're sure you know what you're doing with cyanides and have appropriate safety procedures in place to handle them.


You make me laugh pHzero. Its like the blind leading the blind. And whats wrong with using formic acid to descale the kettle? You know you're supposed to rinse it out afterwards with water right...


Oh for christs sake, are you going to criticise absolutely everything I say/do? You'd flame me if I didnt talk about h&s and now you're complaining that I did. You've made a meaningless reply contributing nothing to this thread. Just grow up.
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itchyfruit
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[*] posted on 22-6-2009 at 14:14


I think i'll wait till i get my new fume cupboard (the one i made is pretty rubbish and noisy)
I'm sure i came across de scaler that had formic acid in it i can't remember the name but it had a orange plastic bottle. Am i right about the ant sting thou or did i just daydream that one? :D
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pHzero
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[*] posted on 22-6-2009 at 14:15


Quote: Originally posted by itchyfruit  
I think i'll wait till i get my new fume cupboard (the one i made is pretty rubbish and noisy)
I'm sure i came across de scaler that had formic acid in it i can't remember the name but it had a orange plastic bottle. Am i right about the ant sting thou or did i just daydream that one? :D


Yeah, that's correct, its found in nettle and ant stings (hence the name "fomic" from "formicos" or something, the greek word for ant)
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[*] posted on 22-6-2009 at 15:08


I do not know the full extent of your chemical abilitys itchyfruit but Formamide can be used in the Leuckart reaction as a means to aminate a carbonyl compound and convert it to the amine. I realise this may be above what you wanted to do with it but Im suprised that it has not been mentioned in this threed yet. Im sure there are people around who would gladly give you compansation to take that bottle off your hands.

Seeing as the main compounds that can be directly made on accident are all highly toxic I think trying to find a buyer would be your best use of this chemical mentioned yet.





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[*] posted on 22-6-2009 at 16:37


We were pretty sure someone would suggest a Leuckart and offer to take that formamide off his hands. Just to Feed your brain.:P
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[*] posted on 22-6-2009 at 16:57


Amides generally require much harsher reaction conditions to hydrolyse in comparison to esters. I very much doubt dilute H2SO4 will do it. There shouldnt be a problem using a concentrated NaOH solution, yielding HCO2Na and ammonia. MSDS says:

Quote:

Teratogen - may cause reproductive abnormalities. This chemical has caused foetal abnormalities and embryonic death in laboratory animals. Possible carcinogen. Irritant. May cause severe burns and blistering which may not be immediately evident or painful.


I dont see how a leuckart reaction with an AMIDE can work - the nitrogen atom is not nucleophilic enough to form the intermediate iminium ion, with a carbonyl compound. What you need for the leuckart reaction is (an excess of) ammonium formate, or an amine with formic acid or its salts.

After searching carefully It appears formamide can be used in the leuckart reaction, but it looks as if additional formic acid is required, presumably to cause hydrolysis to ammonium formate in situ.



[Edited on 23-6-2009 by DJF90]
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Sedit
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[*] posted on 22-6-2009 at 17:18


Heres a nice reference paper for you DJF90.

Attachment: leuckart.pdf (710kB)
This file has been downloaded 947 times






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[*] posted on 22-6-2009 at 17:31


DJF90, according to the literature the Leuckart goes with formamide and the ketone that Sedit and his buddies discuss over at psychonaut.com

Seems like way too many threads devolve to cookery, which is of little interest to us amateur chemists.
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