I have been using trimethylamine to functionalize graphene oxide membrane and PPO, but I can't see the reaction of amine halide on the graphene oxide surface.
Your question is vague. Do you mean halide, acid halide?
Generally, acide halide easily reacts with amines.
Although, reaction between carboxilic acid and amines needs catalyst such as EDC/NHS or DCC
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_%28Organic_Chemistry%29/Carboxylic_Acids/Reactivity_of_Carboxylic_Acids/Conversion_of_Carboxylic_acids_to_amides_using_DCC_as_an_activating_agent
https://www.google.com/url?sa=t&source=web&rct=j&url=https://www.researchgate.net/figure/EDC-NHS-chemistry-EDC-reacts-with-a-carboxylic-acid-group-on-FEP-sheet-indicated-by_fig1_40731516/amp&ved=2ahUKEwjokZullovlAhVNUxoKHQ15BEUQFjALegQIARAB&usg=AOvVaw3YsemqwkTdTxuKF8G2tWfe&cf=1
First, do you maybe mean: ammonium halides such as ammonium chloride? The question is sadly not precise.
Second, how to you see (analyzed) the succes of the reaction?
Hello, thanks for answering .
It would be a tertiary ammonium halide attacking a carboxyl. My doubt is in the reaction mechanism, because it is a bulky group and not as reactive as a tertiary amine, I have difficulty finding the mechanism.
Dear Jaqueline, one of the best way for reaction between carboxylic acid and amine is
Carboxylic acid + thionyl chloride
Then
Acid chloride + amine
However, I've observed reaction between carboxylic acid and amine at high temperature without solvent and catalyst (MWCNT-COOH + tetraethylenepentamine)
Also, there is an article similar to your work:
https://doi.org/10.1039/C2JM34355J
You can evaluate the reaction by FTIR.
decrease or disappearance of -OH stretching peak at 3000-3500 cm-1, C=O peak shift (around 1650-1750 cm-1) and appearance of new peak attributed to the C-N-C can be helpful.
Good luck.
Actually, you asked about the surface of graphene oxide. In my opinion it will not work since on the surface, there are just epoxides and hydroxyl groups and their eventually their corresponding sulfate ester. I guess you plan to open the epoxides and not to react with carboxyl/carbonyl groups at the edges.
I would estimate that it will not work since - you already said - streric hindrance. It will be likely, that the bound proton in ammonium halide will open the epoxide and another water molecule will be attached instead.
Anyhow, amination was investigated quite well here:
Article Chemical reactivity of graphene oxide towards amines elucida...
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