[lapo3399]

Hi,

I am wondering whether the following drawing I made accurately represents the mechanism of the acid-catalyzed hydrolysis of polyethylene terephthalate. I am unsure as to whether both the ester bonds should break (as I have shown below), although I believe this is the case. Also, please notify me of any structural errors or errors in nomenclature/drawing/balancing (e.g. the final hydronium, which I assumed was 2H3O+ because of the 2 extra hydrogens leaving the terephthalic [sic] acid). Any other help would also be appreciated. (Click to make larger...)



Thanks!

[Dan]

The only problem I have with is is the simultaneous protonation of oxygen. I think it's more likely that it occurs one at a time, but this will depend on the strength and concentration of the acid. Other than that, looks ok to me.

[lapo3399]

Thank you for your *delete me* 

[HP]

PTFE is a polymer with high crystalinity %, so hydrolysis mechanism of the ester groups is possible slightly only at the amorphous regions (lamelas) of the polymer chains. Quite a slow reaction i think...