Sciencemadness Discussion Board

Formamide

itchyfruit - 22-6-2009 at 11:51

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!!

Saber - 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]

pHzero - 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.

itchyfruit - 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 :(

pHzero - 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)

pHzero - 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

UnintentionalChaos - 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.

pHzero - 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]

UnintentionalChaos - 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.

itchyfruit - 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:)

setback - 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]

Lambda-Eyde - 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.

pHzero - 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)

Eclectic - 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]

pHzero - 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?

DJF90 - 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...

1281371269 - 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.

pHzero - 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.

itchyfruit - 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

pHzero - 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)

Sedit - 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.

entropy51 - 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

DJF90 - 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]

Sedit - 22-6-2009 at 17:18

Heres a nice reference paper for you DJF90.

Attachment: leuckart.pdf (710kB)
This file has been downloaded 916 times

entropy51 - 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.

Sedit - 22-6-2009 at 17:41

No cookery, although it does appear that we are being over run by those wanting to be the first to cry foul. The fellow just asked of a use for Formamide and not all amination results in psychoactive compounds. I feel this is a way better use of the compound then attempting to generate Carbon Monoxide, formic acid, and HCN combined because all of those can be generated thru other means where as if one has Formamide they can directly influence a carbonyl compound.

LMAO if you think the fellows over at psyconaut talk about the Leuckart all the time your highly mistaken as this one goes right over most of there heads.


[Edited on 23-6-2009 by Sedit]

zed - 22-6-2009 at 21:48

As I recall, Formamide is much more expensive than either Ammonium Formate or its parent...Formic Acid. I don't recall any specific restrictions on selling Formamide. Though I haven't checked.

Perhaps you should sell it and purchase something more useful.

itchyfruit - 23-6-2009 at 10:54

WOW, it seems as thou i've started a bit of an argument 'sorry'
Having looked up Leuckart reaction it would appear formamide has some rather dubious uses which would then leave me with a bit of a dilemma with regards to selling it as i would have no idea what that person would use it for (don't get me wrong each to their own) but i wouldn't want the boys in blue banging on my door accusing me of supplying something dodgy. That said as far as i'm aware it's not restricted and compared to some chemicals not particularly expensive so i doubt anyone would really need what i have.
However i did find out that it is used in DNA/RNA to isolate strands or something, i haven't advanced to this yet but i'll probably save at least some for when i do. As for the rest i may try and swap it for something i'd have more use for.
All though i like the idea of making some HCN i have no real use for it (and certainly no gold to dissolve) and your right i would most likely end up poisoning my self or some other poor bugger!!

But glad i asked i have certainly learnt some interesting stuff
THANKS :D

entropy51 - 23-6-2009 at 12:17

Formamide is listed on the DEA Special Surveillance List:

http://www.deadiversion.usdoj.gov/chem_prog/advisories/surve...

"The Comprehensive Methamphetamine Control Act of 1996 makes it illegal for any person to distribute a "laboratory supply," which is defined in the final rule as a "listed chemical or any chemical substance, or item on a special surveillance list published by the Attorney General, which contains chemicals, products, materials or equipment used in the manufacture of controlled substances and listed chemicals"

Obviously specific to the United States, or persons shipping thereto.

itchyfruit - 23-6-2009 at 12:26

Quote: Originally posted by entropy51  
Formamide is listed on the DEA Special Surveillance List:

http://www.deadiversion.usdoj.gov/chem_prog/advisories/surve...

"The Comprehensive Methamphetamine Control Act of 1996 makes it illegal for any person to distribute a "laboratory supply," which is defined in the final rule as a "listed chemical or any chemical substance, or item on a special surveillance list published by the Attorney General, which contains chemicals, products, materials or equipment used in the manufacture of controlled substances and listed chemicals"

Obviously specific to the United States, or persons shipping thereto.


Does this apply to england to ?

itchyfruit - 23-6-2009 at 13:04

Sorry didn't notice that bit :)

entropy51 - 23-6-2009 at 14:39

If you use the search function at the top of the page with "kno3.com" you will find the threads that discuss the arrest of British citizens arrested for shipping to the US.

setback - 23-6-2009 at 14:55

Quote: Originally posted by entropy51  
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.


Don't really know what your problem is, no one said anything about cookery. Also, who is "we"? You said "we".

entropy51 - 23-6-2009 at 15:01

Us amateur chemists who are not interested in cookery. We who don't post on psychonauts.com about naughty ketones. We.:P

Sedit - 23-6-2009 at 15:37

For someone so against something you seem to know alot about the place:D. Naughty is in the eye of the beholder.

entropy51 - 23-6-2009 at 16:01

Well dude, when you immediately suggested a Leuckart for formamide I opened the trusty old Google and searched for [Sedit, Leuckart] and it popped right up!

In a long life in chemistry I've yet to see Leuckart applied to anything except naughty ketones, although I'm sure it's good for other stuff. Just sayin'.

I'm against things that have made it nearly impossible to legally be an amateur chemist. And don't think this forum ain't watched. There are plenty of GS-13's out there who want to be GS-14's and they only get promoted when they bust somebody. They can do the same Google search that I did.

itchyfruit - 23-6-2009 at 16:04

Quote: Originally posted by entropy51  
If you use the search function at the top of the page with "kno3.com" you will find the threads that discuss the arrest of British citizens arrested for shipping to the US.


interesting(not because i was going to send formamide to the US because i wouldn't) but because by strange coincidence i've spent most of the day making enquires about having some chemicals shipped from the US to here, it's an S1 poison and apparently it's ok to ship up to 450g.
I realise this is a bit of topic i just thought it was an interesting point.
However if anyone knows otherwise please let me know ;)

Sedit - 23-6-2009 at 16:35

"In a long life in chemistry I've yet to see Leuckart applied to anything except naughty ketones, although I'm sure it's good for other stuff. Just sayin'."

Its possibly you have never seen other uses for it because your putting "Sedit" before "Leuckart" in the search engine. You may have much better success just typing in "Leuckart reaction" and "uses".

It has its uses in the synthesis of Isopropyl amine from acetone which I have heard tell of on this forum and many other amines that one may find a need for. It is a useful aminating reagent because most methods for aminating carbonyl compounds involves the use of very toxic mercury or harder to get and work with reagents.

Not to turn this into one of those threeds that won't die but just food for thought... who made the chemicals illegal the few that used them for no good or the folks that think along the lines of yourself in that things like Red P, iodine, and formamide ect... must have no other use then to make drugs because drugmakers use them?

entropy51 - 23-6-2009 at 17:10

I think I'd use reductive amination to prepare isopropylamine from acetone.

My statement that "I've yet to see Leuckart applied to anything except naughty ketones" was based on industry experience in organic synthesis, not Googling.

The named chemicals are illegal because they have been repeatedly found in takedowns of clandestine labs, not because "folks that think along the lines" of myself have dirty minds. I'm sorry that they're denied to everyone because of the selfish and callous acts of the cooks, but that's the cooks' fault, not mine.

All in all just not a good subject of discussion for a forum devoted to amateur science. And this is not really a good place to advertise your website that is at odds with the legal pursuit of amateur science.

Sedit - 23-6-2009 at 17:32

My website is a library of chemistry text that I have gathered thru out the years and compiled into a website soon to be searchable...

Show me, please, how it is related to drug cooking and I will with ease show you how you are highly mistaken. You seem to highly have the wrong idea of who I am and assumptions are just that someone assuming something without total knowlage of the situation.
The reactions existed long before some of the substances they produce where no longer legel. Did you even look at my site before making your assumptions?

You are correct it is not a good discussion for an amateur forum so why people such as yourself insist on bringing it up every chance that they get unprovoked is beyond me. This discussion has been had here time and time again every time someone mentions a reaction that is popular in the underground. Maybe its because folks want to use it as a launching platform for them to spout there beliefs or cover up there true intent, I just dont know.

Point being im done with this conversation because theres no use in rationalizing with those that already have been brainwashed to believe one way or another but the fact still stands as per my original reason for bringing up this topic or the Leuckart before my mention of it was so rudely swept under the rug due to your paranoia, the Leuckart is a fine reaction to aminate ketones for someone that wants to avoid the use of toxic compounds.

Good day to you sir and perhaps open your mind a little bit here and there.

entropy51 - 23-6-2009 at 17:58

No hard feelings, Sedit. I was just a little concerned when you said "Im sure there are people around who would gladly give you compansation to take that bottle off your hands."

Since you were talking about formamide, listed on the DEA's Special Surveillance List, it sounded as if you were maybe crossing a legal line that could bring unwanted LE attention to the forum.

I thought it best to bring it to your attention why this might be a bad idea.

I'll drop it too.

Sedit - 23-6-2009 at 18:17

No nothing like that I was just suggesting along the lines of what zed already stated about selling it and finding something more useful to ones self. I have formic acid and to synthesis formamide or ammonia formate for the Leuckart would be a walk in the park.

As you stated no hard feelings.

setback - 23-6-2009 at 19:21

Please don't assume you speak for everyone entropy, not exactly an endearing trait there. There was nothing to suggest cookery whatsoever. If this guy was using drug terms like freebase, "swim", etc. that would be one thing. Let's not be so presumptive.

DJF90 - 24-6-2009 at 13:18

Additionally the Leuckart reaction is a reductive amination reaction. The iminium intermediate is formed from nucleophilic addition-elimination at the carbonyl, which is then reduced to the amine by the formate ion. If I were to make isopropylamine, the Leuckart reaction would be my method of choice, purely because its so simple! Just add acetone and excess ammonium formate to a flask and reflux. A cosolvent maybe required (I'm thinking IPA). I actually intend on doing this at some point to make diisopropylamine, and then metallating to form the useful base LDA.

entropy51 - 24-6-2009 at 14:31

Let us know how it goes, DJF90. Some people have had trouble duplicating the yields found in the literature, and others have found a tendency to go to tar and complex mixtures of products. One group I worked in had found borohydride reductions of nitriles to be much more reliable than the Leuckart. I hope the isopropyl goes better for you!

[Edited on 24-6-2009 by entropy51]

DJF90 - 24-6-2009 at 16:15

It should go fine. The key to the leuckart is to use excess ammonium formate, just like you would use excess ammonia with alkyl halides to obtain the primary amines. For the diisopropylamine, I think I will use a leuckart reaction to make the isopropylamine, and then I'm not really sure what to do from there. I'll figure it out when I finally get round to thinking about it. Have alot more to experiment with first, but nothing can be done until I've sorted my finances out (got glassware, mantles, rotovap and balance, just need to sort out a cooling system for condensors (figured it out but money is the issue) and clampstands) so I can get my lab set up and operational. Chemicals need to be purchased also :(

Sedit - 24-6-2009 at 16:19

Be sure to figure a camera in also:D.

Perhaps start a nice picture tutorial as I will follow along with you also since I have intrest in making Isopropylamine also for some experiments of mine.

entropy51 - 24-6-2009 at 17:14

One route to diisopropylamine is to react isopropylamine with isopropyl bromide:



Attachment: alkyl amine preps.pdf (1.2MB)
This file has been downloaded 870 times

ot... isopropylamine

Paddywhacker - 24-6-2009 at 17:18

There is a commercial weedkiller preparation sold in NZ .. "G360 Commercial weedkiller - Westminster Garden Products - that is 360 g/litre Glyphosate as the isopropylamine salt. It shouldn't be too difficult to separate it out if needed.

entropy51 - 24-6-2009 at 17:37

Quote: Originally posted by Paddywhacker  
There is a commercial weedkiller preparation sold in NZ .. "G360 Commercial weedkiller - Westminster Garden Products - that is 360 g/litre Glyphosate as the isopropylamine salt. It shouldn't be too difficult to separate it out if needed.


That's what they said about hydrolyzing DEET to get diethylamine. There's a long convoluted thread on it, but I'm not sure that anyone really suceeded.

Sedit - 24-6-2009 at 17:51

I feel the extraction of a very many substances people say are over the counter always seem to turn into an expensive and highly uneconomical(not to mention not as much fun:P) way to aquire many chemicals. If given the choice I would synthesis this thru the Leuckart well before attempting to extract it. The few things that are worth the extra money and time to extract are useful damn near impossible to aquire things like red Phosphorus from matchbooks. And even then only for catalytical work for things such as MeI synthesis and the likes because using it in a reaction where it is consumed means you have to go thru all that crap again.

[Edited on 25-6-2009 by Sedit]

jamit - 31-10-2015 at 09:31

Anyone interested in buying some formamide? I been given several 500ml bottles and I don't have any use for it as I don't know what I can use it for.
And this thread hasn't shed much light on its usage.
And since it produces carbon monoxide with addition of acid I want to be sure if I'm going to use it for some experiment.

Anyone suggest some other experiments? Does it have a place in a home lab?
Lastly why is it listed as a restricted/ watched chemical?

[Edited on 31-10-2015 by jamit]