New Kids in Lactide Polymerization: Highly Active and Robust Iron Guanidine Complexes as Superior Catalysts

R.D. Rittinghaus; P.M. Schafer; P. Albrecht; C. Conrads; A. Hoffmann; N.N. Ksiazkiewicz; O. Bienemann; A. Pich; S. Herres-Pawlis

doi:10.1002/cssc.201900481

New Kids in Lactide Polymerization: Highly Active and Robust Iron Guanidine Complexes as Superior Catalysts

R.D. Rittinghaus, P.M. Schafer, P. Albrecht, C. Conrads, A. Hoffmann, N.N. Ksiazkiewicz, O. Bienemann, A. Pich, S. Herres-Pawlis^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Polylactide is a biodegradable versatile material based on annually renewable resources and thus CO2-neutral in its lifecycle. Until now, tin(II)octanoate [Sn(Oct(2))] was used as catalyst for the industrial ring-opening polymerization of lactide in spite of its cytotoxicity. On the way towards a sustainable catalyst, three iron(II) hybrid guanidine complexes were investigated concerning their molecular structure and applied to the ring-opening polymerization of lactide. The complexes could polymerize unpurified technical-grade rac-lactide as well as recrystallized l-lactide to long-chain polylactide in bulk with monomer/initiator ratios of more than 5000:1 in a controlled manner following the coordination-insertion mechanism. For the first time, a biocompatible complex has surpassed Sn(Oct)(2) in its polymerization activity under industrially relevant conditions.

Original language	English
Pages (from-to)	2161-2165
Number of pages	5
Journal	Chemsuschem
Volume	12
Issue number	10
DOIs	https://doi.org/10.1002/cssc.201900481
Publication status	Published - 21 May 2019

Keywords

bioplastics
degradation
guanidines
iron
lactide
ligands
magnesium
mechanism
polyesters
polylactide
ring-opening polymerization
zinc-complexes
POLYESTERS
MECHANISM
ZINC-COMPLEXES
POLYLACTIDE
MAGNESIUM
LIGANDS
DEGRADATION
RING-OPENING POLYMERIZATION

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10.1002/cssc.201900481

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@article{ec883f72cc3f4d1690bbcc9e6dc99e4a,

title = "New Kids in Lactide Polymerization: Highly Active and Robust Iron Guanidine Complexes as Superior Catalysts",

abstract = "Polylactide is a biodegradable versatile material based on annually renewable resources and thus CO2-neutral in its lifecycle. Until now, tin(II)octanoate [Sn(Oct(2))] was used as catalyst for the industrial ring-opening polymerization of lactide in spite of its cytotoxicity. On the way towards a sustainable catalyst, three iron(II) hybrid guanidine complexes were investigated concerning their molecular structure and applied to the ring-opening polymerization of lactide. The complexes could polymerize unpurified technical-grade rac-lactide as well as recrystallized l-lactide to long-chain polylactide in bulk with monomer/initiator ratios of more than 5000:1 in a controlled manner following the coordination-insertion mechanism. For the first time, a biocompatible complex has surpassed Sn(Oct)(2) in its polymerization activity under industrially relevant conditions.",

keywords = "bioplastics, degradation, guanidines, iron, lactide, ligands, magnesium, mechanism, polyesters, polylactide, ring-opening polymerization, zinc-complexes, POLYESTERS, MECHANISM, ZINC-COMPLEXES, POLYLACTIDE, MAGNESIUM, LIGANDS, DEGRADATION, RING-OPENING POLYMERIZATION",

author = "R.D. Rittinghaus and P.M. Schafer and P. Albrecht and C. Conrads and A. Hoffmann and N.N. Ksiazkiewicz and O. Bienemann and A. Pich and S. Herres-Pawlis",

note = "Funding Information: R.D.R. thanks the DBU (Deutsche Bundesstiftung Umwelt) for funding. P.M.S. thanks the Hanns-Seidel-Foundation (fellowship) for funding (Bundesministerium f{\"u}r Bildung und Forschung). Furthermore, the authors acknowledge the funding by the Deutsche Forschungsgemeinschaft in the framework of the SFB985 and thank Total Corbion for lactide donations and B. Jansen for TGA measurements as well as Dr. R. Vinokur for DSC and TGA measurements. Calculation time from the OCuLUS Cluster at the PC2 Paderborn is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = may,

day = "21",

doi = "10.1002/cssc.201900481",

language = "English",

volume = "12",

pages = "2161--2165",

journal = "Chemsuschem",

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TY - JOUR

T1 - New Kids in Lactide Polymerization: Highly Active and Robust Iron Guanidine Complexes as Superior Catalysts

AU - Rittinghaus, R.D.

AU - Schafer, P.M.

AU - Albrecht, P.

AU - Conrads, C.

AU - Hoffmann, A.

AU - Ksiazkiewicz, N.N.

AU - Bienemann, O.

AU - Pich, A.

AU - Herres-Pawlis, S.

N1 - Funding Information: R.D.R. thanks the DBU (Deutsche Bundesstiftung Umwelt) for funding. P.M.S. thanks the Hanns-Seidel-Foundation (fellowship) for funding (Bundesministerium für Bildung und Forschung). Furthermore, the authors acknowledge the funding by the Deutsche Forschungsgemeinschaft in the framework of the SFB985 and thank Total Corbion for lactide donations and B. Jansen for TGA measurements as well as Dr. R. Vinokur for DSC and TGA measurements. Calculation time from the OCuLUS Cluster at the PC2 Paderborn is gratefully acknowledged. Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/5/21

Y1 - 2019/5/21

N2 - Polylactide is a biodegradable versatile material based on annually renewable resources and thus CO2-neutral in its lifecycle. Until now, tin(II)octanoate [Sn(Oct(2))] was used as catalyst for the industrial ring-opening polymerization of lactide in spite of its cytotoxicity. On the way towards a sustainable catalyst, three iron(II) hybrid guanidine complexes were investigated concerning their molecular structure and applied to the ring-opening polymerization of lactide. The complexes could polymerize unpurified technical-grade rac-lactide as well as recrystallized l-lactide to long-chain polylactide in bulk with monomer/initiator ratios of more than 5000:1 in a controlled manner following the coordination-insertion mechanism. For the first time, a biocompatible complex has surpassed Sn(Oct)(2) in its polymerization activity under industrially relevant conditions.

AB - Polylactide is a biodegradable versatile material based on annually renewable resources and thus CO2-neutral in its lifecycle. Until now, tin(II)octanoate [Sn(Oct(2))] was used as catalyst for the industrial ring-opening polymerization of lactide in spite of its cytotoxicity. On the way towards a sustainable catalyst, three iron(II) hybrid guanidine complexes were investigated concerning their molecular structure and applied to the ring-opening polymerization of lactide. The complexes could polymerize unpurified technical-grade rac-lactide as well as recrystallized l-lactide to long-chain polylactide in bulk with monomer/initiator ratios of more than 5000:1 in a controlled manner following the coordination-insertion mechanism. For the first time, a biocompatible complex has surpassed Sn(Oct)(2) in its polymerization activity under industrially relevant conditions.

KW - bioplastics

KW - degradation

KW - guanidines

KW - iron

KW - lactide

KW - ligands

KW - magnesium

KW - mechanism

KW - polyesters

KW - polylactide

KW - ring-opening polymerization

KW - zinc-complexes

KW - POLYESTERS

KW - MECHANISM

KW - ZINC-COMPLEXES

KW - POLYLACTIDE

KW - MAGNESIUM

KW - LIGANDS

KW - DEGRADATION

KW - RING-OPENING POLYMERIZATION

U2 - 10.1002/cssc.201900481

DO - 10.1002/cssc.201900481

M3 - Article

SN - 1864-5631

VL - 12

SP - 2161

EP - 2165

JO - Chemsuschem

JF - Chemsuschem

IS - 10

ER -