In synthesis octanoyl-cysteine surfactant, octanoyl chloride is added dropwise to the solution of cysteine dissolved in water. To synthesis surfactant, cysteine should alkylised from N side, but octanoyl chloride is hydrolysed by water and eventually has less bonding affinity to cysteine. So any advice on using another solvent for cysteine (polar aprotic ones, I reckon!) would be appreciated.
Hello Mojtaba,
I also work on the synthesis of amino acid based surfactants and for the synthesis of N-acyl surfactants (the type of surfactant you are trying to synthesize) I normally use THF as solvent in the presence of TEA and catalytic amount of DMAP. The reaction normally takes place under refluxing THF for 18 hours.
Nausheen
Dear Nausheen
Thanks on this. Could you please share more details on the synthesis process (e.g., ratio of solvents, concentrations, additives, operation pH and etc) - a published work might be more helpful.
Thanks
Dear Mojtaba,
You can refer to one of our published paper. Please find the link below.
Article Synthesis, physicochemical, and biological activities of nov...
Hope it helps.
Thanks Nausheen on this. I followed the method for the synthesis of cysteine-octanoyl surfactant, but there is not aminolysis reaction happening because cysteine shows very low solubility in THF/TEA solution!
Have you carried out the experiment as per the paper and have you done the work-up and characterisation?
Yes, I did but couldn't see white solid. It seems there is no reaction happening between cysteine and octanoyl chloride.
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