[bharathi]

Hi all,
I have observed a typical behaviour while hydrolysing a compound.
3-chloropropyl amine HCl is hydrolysed with caustic and extracted into an organic solvent. WHile distilling out the solvent to isolate the base, towards the end of distillation the residue turned to a thick plastic like mass and bumped out.
Does 3-chloropropyl amine polymerise ?.If so, what is the onset temperature for this phenomenon to occur.
please help me out.

Regards,
Bharathi

[plu]

Does 3-chloropropyl amine polymerise ?

I believe it does.  The amine group will react via S_N2 with the chloro group to form a step-growth polymer.  I am not sure of the onset temperature though.  Which solvent were you using?

[bharathi]

This was observed in several solvents like dimethylsulfoxide, dichloromethane, toluene, etheral solvent, etc.  However ,in dichloromethane , this behaviour is observed readily.

Regards,
Bharathi

[plu]

Yes, these solvents would have all promoted the polymerization process.  What are you trying to do with your experiment, may I ask?

[bharathi]

In this expt, I am trying to react 3-chloropropyl amine  and not the hydrochloride with another reagent B to form a condensation product. But in the process, I observe the instability of 3-chloropropyl amine before it can react with B. How can this be taken care of??

Regds/Bharathi