Sciencemadness Discussion Board

Nitroguanidine from agmatine sulfate.

Hunterman2244 - 27-4-2019 at 18:18

I have a source for agmatine sulfate, and was looking for a route to nitroguanadine. I have wanted to make some nitroguanidine for a while, and agmatine sulfate seems it should be a simple starting material. Any literature or obvious path?

Boffis - 28-4-2019 at 02:54

I had never heard of agmatine before but looking up the structure I think you are in for a hard time. There is no readily hydrolysable bridge between the aminobutane group and the guanidine. Any attempt to break up this molecule will most likely yield 1,4-diaminobutane (a very smelly compound), the guanidine moiety being totalled distroyed.

Hunterman2244 - 30-4-2019 at 08:17

Quote: Originally posted by Boffis  
I had never heard of agmatine before but looking up the structure I think you are in for a hard time. There is no readily hydrolysable bridge between the aminobutane group and the guanidine. Any attempt to break up this molecule will most likely yield 1,4-diaminobutane (a very smelly compound), the guanidine moiety being totalled distroyed.
Oh, alright. I thought it would be a bit of an issue, but wanted to be sure.

Boffis - 1-5-2019 at 10:06

The best source of guanidine nitrate for nitroguanidine production is the low temperature fusion of ammonium nitrate and dicyandiamide. The latter can be prepared from garden-grade calcium cyanamide such as "Perlka" cyanamide. The yield is not great but if you can get it ground to a fine powder you need only water and a little sulphuric acid so its a cheap reaction.

Alkoholvergiftung - 1-5-2019 at 10:31

I find the Methode saver of heating Dicyandiamid with sulfuric Acid. You get Guanidinsulfate. Or you trate Dicyandiamid with HCL and HNO3 You get Guanidinnitrate.

TGSpecialist1 - 1-5-2019 at 17:22

We also made guanidine from urea and sulfamic acid on this forum: http://www.sciencemadness.org/talk/viewthread.php?tid=8911

The links to images still work.

And also from urea, ammonium nitrate and silica cat litter: https://www.youtube.com/watch?v=QK_zsRBlkt0


[Edited on 2-5-2019 by TGSpecialist1]

Boffis - 3-5-2019 at 02:10

@Alkoholvergiftung. The advantage of the dicyanamide-ammonium nitrate fusion is that the yield is high (80-85%) and theoretically you get 2 moles of guanidine per mole of dicyandiamide while with the hydrolysis reaction you can only get 1:1 yield at best and the availability of dicyandiamide is usually the limiting commodity. The main disadvantage of this method it that it needs to be carried out in small batches as, alledgedly, scale up sometimes leads to deflagration though I haven't had this problem.