Dear Saba, there are reports in the chemical literature that ethylene glycol can react with 2 equivalents of primary amines R-NH2 under formation of oxalamides, (R)NH-C=O)-C(=O)-NH(R). It has been reported in the paper cited below that the reaction is catalyzed by a homogeneous ruthenium catalyst:

Synthesis of oxalamides by acceptorless dehydrogenative coupling of ethylene glycol and amines and the reverse hydrogenation catalyzed by ruthenium

Article Synthesis of oxalamides by acceptorless dehydrogenative coup...

This interesting article is freely available as public full text on RG.

I assume that you had no such catalyst present in your reaction system. However, chances are that a metallic component in the inner surface of your autoclave acted as catalyst. Thus I think that reaction of ethylene glycol with an amine could have taken place in your case. Did you observe any solid product?

Good luck with your work and best wishes, Frank Edelmann

Thanks for your answer. My amine is N,N,N-Trimethyladamantan-1-aminium hydroxide and it is important to me to know that is a reaction occur or not, because it damages my synthesized membrane and if I can be sure about that, I can prove my project, but I don't know how I prove it.

Dear Saba,

thanks for your kind response and explanation. In that case the literature reference which I mentioned in my first answer does not apply because you don't have a primary amine. In order ro rule out a solvent effect you can perhaps run the reaction in a different solvent. Moreover, in order to exclude any metal catalysis, you could try a Teflon-lined autoclave.

The components of my solution is aluminnium, sodium hydroxide, silsium,N,N,N-Trimethyladamantan-1-aminium hydroxide, and choline chloride which is unstable in high temperature and divided to another amine and ethylene glycol, and I put my solution first in a Teflon then in an auto clave. I'm so confused in this way. And I can't found the problem, then I thought the probability of a reaction between amine and ethylene glycol.

Hello Saba, many thanks for the explanation. This is quite a complicated reaction mixture which makes me wonder what your original goals was. Did you follow a literature preparation? Moreover, it would be interesting to know what mdae you worry that something went wrong.

Hello Mr. Frank my major goal is synthesizing a zeolitic membrane to gas sepration, and now I couldn't get the appropriate flux, and I think about the probability of this reaction in my solution and now I don't know how can I prove that or how can I make sure that this reaction happens or not which may guide my research in other.

Dear Saba, for some very useful general information about zeolite membranes for gas separation please have a look at the following book chapter:

Design and Evaluation of Gas Transport through a Zeolite Membrane on an Alumina Support

Chapter Design and Evaluation of Gas Transport through a Zeolite Mem...

The best thing about this article is that it is freely available as public full text on RG, so that you can download it as pdf file. The use of N,N,N-trimethyladamantan-1-ammonium hydroxide is described in the following potentially useful article:

Preparation of steam-stable high-silica CHA (SSZ-13) membranes for CO2/CH4 and C2H4/C2H6 separation

Article Preparation of steam-stable high-silica CHA (SSZ-13) membran...

This article has not yet been posted as public full text, but two of the authors have RG profiles. This means that you can contact them directly via RG and request the full text of the paper.

With best wishes, Frank Edelmann

Thanks alot for your kind response.

Sure, I request for both of them.