Sciencemadness Discussion Board

Interesting Betaine Compounds

man_from_mystery_babylon - 21-7-2005 at 04:40

In case anyone is interested I thought I would mention that in Federoff Vol. 1, I came across mention of explosive compounds made from betaine and an oxyacid; e.g., nitric, chloric, perchloric, and picric. There is even a dichromate and permanganate compound.

There are also two related patents: GB191405736 and GB191405737.

Betaine is available quite inexpensively in powdered form as a dietary supplement. (It is a good methyl donor and possibly good for people taking high doses of niacin to raise their HDL cholesterol for example).

man_from_mystery_babylon - 28-7-2005 at 03:20

I take betaine as a nutritional supplement.
It is available as straight betaine (aka trimethylglycine or TMG) in powdered form.

I have also seen betaine.HCL for sale in stores that sell nutritional products.

I think it is interesting because it appears that you can make Betaine.HNO3, HClO4, etc., with dilute acids.

Unfortunately, other than what's in the the patents, I can't find any more information about the properties of these compounds.

Very interesting ,

Rosco Bodine - 28-7-2005 at 09:12

Very interesting indeed , not only
for the energetic salts , but also for
the use of betaine as a stabilizer .

Betaine is also called TMG ,
( trimethyl glycine )

Attached are the two patents as one file .

Attachment: GB191405736 and GB191405737 Betaine related.pdf (203kB)
This file has been downloaded 979 times

man_from_mystery_babylon - 31-7-2005 at 10:49

Thanks for posting the patents as pdf files, Rosco.

BTW, if you come across any other info on these compounds, either in the literature or by way of experiment, please post it here if possible. Thanks.

Rosco Bodine - 31-7-2005 at 12:28

The use of betaine as a stabilizer for
nitromannite , inositol hexanitrate ,
erythritol tetranitrate , and other nitrated polyols , particularly for their melt eutectics
with PETN is a definite interest . Also the
nitrated cellulosic materials including
cyclodextrin , hemicellulose , inulin , resistant maltodextrin , microcrystalline cellulose , and even potato nitrostarch ,
would be candidates for a betaine stabilizer . Perhaps even methylglucoside tetranitrate , polydextrose , and even the nitrosugars would also benefit in their stability from use of betaine . From the
patent decription it would seem to be an ideal stabilizer , and cheaply available as a nutritional supplement item . You could spend two or three years with experiments related to the potential usefulness of betaine , and it is something pretty obscure in the literature . Really this is good find , even if there was only the value as a stabilizer to be investigated .

As a bonus of course are the energetic salts , and their possible use alone or as
eutectics , and/or detonation catalysts ,
especially the chromate and permanganate salts . The perchlorate salt could be interesting also , alone or
in combination with other perchlorates like
guandine and urea and methylamine perchlorate , or ammonium perchlorate .

Depending on the solubility of the betaine perchlorate , it might be gotten simply by dissolving betaine in warm ammonium perchlorate solution , perhaps adding HNO3 or HCl . There would also seem to be possible double salts . You could really
fill up a notebook with betaine experiments and likely find some interesting results along the way .

[Edited on 31-7-2005 by Rosco Bodine]

Choline and derivatives

chemoleo - 22-9-2005 at 17:12

On a slight but yet related off-topic note -
choline can be purchased from various health food places. It's structure is

and thus very similar to betaine, which is

Here, however, not only will it form salts, but also it can potentially form i.e. the nitric acid esters!

One question is of course whether the quaternary nitrogen is affected, i.e. whether trimethylamine nitrate and ethanol nitrate will be produced. Anyone knows more how quaternary and substituted N behaves with strong acid?

If it would work as I hope, not only would you have the nitrate salt but the nitric acid ester at the same time, similiar to the nitrate salt of ethanolamine nitrate (which is not so much of great use).

Any thoughts?

Rosco Bodine - 3-3-2007 at 16:09

Yes indeed , very interesting possibility for choline .

PATR describes energetic salts whose properties as explosives were not tested or reported in any detail .
See Vol.3 , page C 274

Choline forms a perchlorate salt , mp 273C


The perchlorate salt on being heated in water bath with 65% HNO3 does form a nitratoperchlorate mp 186C ,
sl sol water , explodes strongly when heated above mp .


This compound is also called nitrocholine perchlorate .

Hofmann , K.A. and Hobold , K. , Ber. chem. Ges. 44 , 1766 (1911)

Choline similarly forms a salt with picric acid , yellow needles , mp 249C explosive properties reported .

The picrate could be extremely interesting if upon heating
with conc. HNO3 it would similarly form a nitratopicrate ,
as this may not only have interesting properties itself ,
but could also potentially form metallic salts having initiating properties .

The nitratoperchlorate could also possibly form explosive
metallic salts .

Some very interesting experiments could be devised for
these obscure and totally unknown possible compounds .

Congratulations on thinking outside the box ....
this is very intriguing .

The possibility of a choline permanganate or chromate ,
with and without subsequent nitration to a nitratocompound also would seem possible and
worth experimentation .

Extreme conditions would not be required for the
syntheses of these choline compounds but their
potential energy is very high .

[Edited on 4-3-2007 by Rosco Bodine]