Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide

Nica, Simona; Ionescu, Sorana; Hanganu, Anamaria; Duldner, Monica; Iancu, Stela; Sarbu, Andrei; Filip, Petru; Bartha, Emeric

Simona Nica, Sorana Ionescu, Anamaria Hanganu, Monica Duldner, Stela Iancu, Andrei Sarbu, Petru Filip, Emeric Bartha

Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide

Abstract:

Glycolysis of PET waste with isosorbide, a biomass derived diol, was catalyzed by commercially available 1,5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) at temperature up to 190°C when low molecular weight oligomer containing at least one equivalent of isosorbide was obtained. The structural assignment of the oligomer product was established by NMR spectroscopy showing predominantly end-chain bonded isosorbide with exo/endo ratio of 55/45. Mechanistic considerations of the transesterification reaction of isosorbide with dimethylterephthalate (DMT) as model reaction revealed that the hydrogen bonding interaction of TBD with this diol is the favored mechanism pathway. This was established by corroborating solution NMR spectroscopy studies with DFT calculations at B3LYP level where it was observed that isosorbide is hydrogen bonded to TBD through both endo and exo hydroxyl groups. On the other hand, the TBD catalyst reacts with dimethylterephthalate at low temperature forming a stable, easy to handle covalently bonded adduct.

Keywords:
PET waste; isosorbide; organocatalysis; transesterification

Issue: 2018, Volume 69, Issue 6

Pages: 1319-1326

Publication date: 2018/7/15

https://doi.org/10.37358/RC.18.6.6318

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
NICA, S., IONESCU, S., HANGANU, A., DULDNER, M., IANCU, S., SARBU, A., FILIP, P., BARTHA, E., Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide, Rev. Chim., 69(6), 2018, 1319-1326.

Vancouver
Nica S, Ionescu S, Hanganu A, Duldner M, Iancu S, Sarbu A, Filip P, Bartha E. Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide. Rev. Chim.[internet]. 2018 Jun;69(6):1319-1326. Available from: https://doi.org/10.37358/RC.18.6.6318

APA 6th edition
Nica, S., Ionescu, S., Hanganu, A., Duldner, M., Iancu, S., Sarbu, A., Filip, P. & Bartha, E. (2018). Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide. Revista de Chimie, 69(6), 1319-1326. https://doi.org/10.37358/RC.18.6.6318

Harvard
Nica, S., Ionescu, S., Hanganu, A., Duldner, M., Iancu, S., Sarbu, A., Filip, P., Bartha, E. (2018). 'Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide', Revista de Chimie, 69(6), pp. 1319-1326. https://doi.org/10.37358/RC.18.6.6318

IEEE
S. Nica, S. Ionescu, A. Hanganu, M. Duldner, S. Iancu, A. Sarbu, P. Filip, E. Bartha, "Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide". Revista de Chimie, vol. 69, no. 6, pp. 1319-1326, 2018. [online]. https://doi.org/10.37358/RC.18.6.6318

Text
Simona Nica, Sorana Ionescu, Anamaria Hanganu, Monica Duldner, Stela Iancu, Andrei Sarbu, Petru Filip, Emeric Bartha,
Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide,
Revista de Chimie,
Volume 69, Issue 6,
2018,
Pages 1319-1326,
ISSN 2668-8212,
https://doi.org/10.37358/RC.18.6.6318.
(https://revistadechimie.ro/Articles.asp?ID=6318)
Keywords: PET waste; isosorbide; organocatalysis; transesterification

RIS
TY - JOUR
T1 - Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide
A1 - Nica, Simona
A2 - Ionescu, Sorana
A3 - Hanganu, Anamaria
A4 - Duldner, Monica
A5 - Iancu, Stela
A6 - Sarbu, Andrei
A7 - Filip, Petru
A8 - Bartha, Emeric
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2018
VL - 69
IS - 6
SP - 1319
EP - 1326
UR - https://doi.org/10.37358/RC.18.6.6318
KW - PET waste; isosorbide; organocatalysis; transesterification
ER -

BibTex
@article{RevCh2018P1319,
author = {Nica Simona and Ionescu Sorana and Hanganu Anamaria and Duldner Monica and Iancu Stela and Sarbu Andrei and Filip Petru and Bartha Emeric},
title = {Mechanistic Investigations of the Organocatalytic Depolymerization of PET Waste with Isosorbide},
journal = {Revista de Chimie},
volume = {69},
number = {6},
pages = {1319-1326},
year = {2018},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.18.6.6318},
url = {https://revistadechimie.ro/Articles.asp?ID=6318}
}

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