Journal ArticleDOI
Guanidine and Amidine Organocatalysts for Ring-Opening Polymerization of Cyclic Esters
Bas G. G. Lohmeijer,Russell C. Pratt,Frank A. Leibfarth,John W. Logan,David A. Long,Andrew P. Dove,Fredrik Nederberg,Jeongsoo Choi,Charles G. Wade,Robert M. Waymouth,James L. Hedrick +10 more
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TLDR
In this article, the ring-opening polymerization (ROP) of cyclic esters such as lactide (LA), δ-valerolactone (VL), and e-caprolactone(CL) was achieved.Abstract:
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), N-methyl-TBD (MTBD), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are effective organocatalysts for the ring-opening polymerization (ROP) of cyclic esters such as lactide (LA), δ-valerolactone (VL), and e-caprolactone (CL). TBD is shown to polymerize LA, VL, and CL in a fast and controlled manner, whereas MTBD and DBU polymerized LA and addition of a thiourea cocatalyst led to the ROP of VL and CL being achieved. Each of the catalysts produced polymers displaying high end group fidelity, good correlation between theoretical and observed molecular weight, and linear relationships between conversion and molecular weight. The enhanced activity of TBD relative to MTBD and DBU is attributed to its bifunctionality, enabling the simultaneous activation of both the cyclic ester monomer and the alcohol group of the initiator/propagating species. Temperature-dependent NMR studies generated individual association constants for MTBD with benzyl alcohol and thiourea with VL. ...read more
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1,1,3,3-Tetramethylguanidine-Promoted Ring-Opening Polymerization of N-Butyl N-Carboxyanhydride Using Alcohol Initiators
TL;DR: In this article, N-Butyl N-carboxyanhydride (Bu-NCA) was polymerized in THF to produce poly(N-butylglycine) using benzyl alcohol initiator and 1,1,3,3-tetramethylguanidine (TMG) promoter.
Journal ArticleDOI
Expanding Plastics Recycling Technologies: Chemical Aspects, Technology Status and Challenges
Houqian Li,Horacio A. Aguirre-Villegas,R D Allen,Xiang-Fei Bai,Craig H. Benson,Gregg T. Beckham,Sabrina L. Bradshaw,Jessica L. Brown,Robert H. Brown,Victor S. Cecon,Julia B. Curley,Greg Curtzwiler,Son Ui Dong,Soumika Gaddameedi,John E. Estela-García,Ive Hermans,Min Soo Kim,Jiabi Ma,Lesli O. Mark,Manos Mavrikakis,Olumide O. Olafasakin,Tim A. Osswald,Konstantinos G. Papanikolaou,Hari Radhakrishnan,Marco A. Sanchez-Castillo,Kevin Sanchez-Rivera,Khairun Nafiz Tumu,Reid C. Van Lehn,Keith Vorst,Mark M. Wright,Jiayang Wu,Victor M. Zavala,Panzheng Zhou,George W. Huber +33 more
TL;DR: Less than 10% of the plastics generated globally are recycled, while the rest are incinerated, accumulated in landfills, or leach into the environment as discussed by the authors , while new technologies are emerging to chemically recycle them.
Journal ArticleDOI
Dual Catalysis Based on N-Heterocyclic Olefins for the Copolymerization of Lactones: High Performance and Tunable Selectivity
Stefan Naumann,Dongren Wang +1 more
TL;DR: In this paper, the cooperative interaction of four structurally different N-heterocyclic olefins (NHOs) with a range of simple metal halides as Lewis acidic cocatalysts is employed for the homo-and copolymerization of e-caprolactone (CL) and δ-valerolactone(VL).
Journal ArticleDOI
Synergistic Empirical and Theoretical Study on the Stereoselective Mechanism for the Aluminum Salalen Complex Mediated Polymerization of rac-Lactide
Ines dos Santos Vieira,Emma L. Whitelaw,Matthew D. Jones,Sonja Herres-Pawlis,Sonja Herres-Pawlis +4 more
TL;DR: The chiral stationary phase for high-performance liquid chromatography showed good chiral recognition ability towards various racemates, including polymethine and cadmium arsenide.
Journal ArticleDOI
Organocatalytic copolymerization of mixed type monomers
TL;DR: In this paper, a mini-review on pathways to construct copolymer chain structures by organocatalytic Copolymerization of mixed type monomers (comonomers bearing different polymerizing moieties) is presented.
References
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Journal ArticleDOI
Controlled ring-opening polymerization of lactide and glycolide.
TL;DR: This work focuses on the characterization of the phytochemical components of Lactide ROP and their role in the regulation of cell reprograming.
Journal ArticleDOI
Polymerization of Lactide with Zinc and Magnesium β-Diiminate Complexes: Stereocontrol and Mechanism
Bradley M. Chamberlain,Ming Cheng,David Roger Moore,Tina M. Ovitt,Emil B. Lobkovsky,Geoffrey W. Coates +5 more
TL;DR: The substituents on the beta-diiminate ligand exert a significant influence upon the course of the polymerizations, affecting both the degree of stereoselectivity and the rate of polymerization.
Journal ArticleDOI
A review of biodegradable polymers: uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies
TL;DR: A review of the uses of biodegradable polymers in terms of their relevance within current plastic waste management of packaging materials, biomedical applications and other uses is presented in this paper.
Journal ArticleDOI
Extension of the self-consistent spectrophotometric basicity scale in acetonitrile to a full span of 28 pKa units: unification of different basicity scales.
Ivari Kaljurand,Agnes Kütt,Lilli Sooväli,Toomas Rodima,Vahur Mäemets,and Ivo Leito,Ilmar A. Koppel +6 more
TL;DR: The earlier compiled self-consistent spectrophotometric basicity scale in acetonitrile (AN) was expanded to range from 3.8 to 32.0 pK(a) units, that is 28 orders of magnitude, and 54 new relative basicity measurements were carried out and 37 new compounds were introduced to the scale.
Journal ArticleDOI
Stereochemistry of Lactide Polymerization with Chiral Catalysts: New Opportunities for Stereocontrol Using Polymer Exchange Mechanisms
Tina M. Ovitt,Geoffrey W. Coates +1 more
TL;DR: A polymer exchange mechanism is proposed to account for the PLA microstructures resulting from rac-4, which polymerizes meso-lactide to syndiotactic poly(lactic acid) (PLA) and heterotactic and isotactic stereoblock PLA, respectively.