Facile synthesis of poly(trimethylene carbonate) by alkali metal carboxylate-catalyzed ring-opening polymerization

Kaoru Takojima; Tatsuya Saito; Cedric Vevert; Viko Ladelta; Panagiotis Bilalis; Jun Watanabe; Shintaro Hatanaka; Takashi Konno; Takuya Yamamoto; Kenji Tajima; Nikos Hadjichristidis; Takuya Isono; Toshifumi Satoh

doi:10.1038/s41428-019-0264-6

Facile synthesis of poly(trimethylene carbonate) by alkali metal carboxylate-catalyzed ring-opening polymerization

Kaoru Takojima, Tatsuya Saito, Cedric Vevert, Viko Ladelta, Panagiotis Bilalis, Jun Watanabe, Shintaro Hatanaka, Takashi Konno, Takuya Yamamoto, Kenji Tajima, Nikos Hadjichristidis, Takuya Isono, Toshifumi Satoh

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15 Scopus citations

Abstract

Alkali metal carboxylates, including sodium acetate, sodium benzoate, and sodium sorbate, which are all readily available and widely used as food additives, were found to promote the ring-opening polymerization (ROP) of trimethylene carbonate (TMC) to produce poly(trimethylene carbonate) (PTMC). The sodium acetate-catalyzed ROP of TMC proceeded in the presence of an alcohol initiator under solvent-free conditions at 70 °C, even at very low catalyst loadings of 0.01–0.0001 mol%. The controlled nature of this ROP system enabled the synthesis of PTMCs with predicted molecular weights ranging from 2400 to 11 700 g mol−1 and narrow dispersities (~1.23). Importantly, ROP is initiated by an alcohol initiator, allowing PTMC production with desired functional groups, such as azido, alkyne, and methacrylate groups, at the α-chain end. Furthermore, the poly(L-lactic acid)-b-PTMC-b-poly(L-lactic acid) triblock copolymer, a biodegradable thermoplastic elastomer, was successfully synthesized in one pot via the sodium acetate-catalyzed ring-opening block copolymerization of TMC and L-lactide with a 1,3-propanediol initiator.

Original language	English (US)
Pages (from-to)	103-110
Number of pages	8
Journal	Polymer Journal
Volume	52
Issue number	1
DOIs	https://doi.org/10.1038/s41428-019-0264-6
State	Published - Sep 24 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was financially supported by the JSPS KAKENHI (Grant Number JP18H04639) (Hybrid Catalysis for Enabling Molecular Synthesis on Demand), Frontier Chemistry Center (Hokkaido University), Inamori Foundation, and Grant-in-Aid for JSPS Research Fellows. TS gratefully acknowledges the JSPS Fellowship for Young Scientists. VL, PB, and NH gratefully acknowledge the support of King Abdullah University of Science and Technology.

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Takojima, K., Saito, T., Vevert, C., Ladelta, V., Bilalis, P., Watanabe, J., Hatanaka, S., Konno, T., Yamamoto, T., Tajima, K., Hadjichristidis, N., Isono, T., & Satoh, T. (2019). Facile synthesis of poly(trimethylene carbonate) by alkali metal carboxylate-catalyzed ring-opening polymerization. Polymer Journal, 52(1), 103-110. https://doi.org/10.1038/s41428-019-0264-6

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title = "Facile synthesis of poly(trimethylene carbonate) by alkali metal carboxylate-catalyzed ring-opening polymerization",

abstract = "Alkali metal carboxylates, including sodium acetate, sodium benzoate, and sodium sorbate, which are all readily available and widely used as food additives, were found to promote the ring-opening polymerization (ROP) of trimethylene carbonate (TMC) to produce poly(trimethylene carbonate) (PTMC). The sodium acetate-catalyzed ROP of TMC proceeded in the presence of an alcohol initiator under solvent-free conditions at 70 °C, even at very low catalyst loadings of 0.01–0.0001 mol%. The controlled nature of this ROP system enabled the synthesis of PTMCs with predicted molecular weights ranging from 2400 to 11 700 g mol−1 and narrow dispersities (~1.23). Importantly, ROP is initiated by an alcohol initiator, allowing PTMC production with desired functional groups, such as azido, alkyne, and methacrylate groups, at the α-chain end. Furthermore, the poly(L-lactic acid)-b-PTMC-b-poly(L-lactic acid) triblock copolymer, a biodegradable thermoplastic elastomer, was successfully synthesized in one pot via the sodium acetate-catalyzed ring-opening block copolymerization of TMC and L-lactide with a 1,3-propanediol initiator.",

author = "Kaoru Takojima and Tatsuya Saito and Cedric Vevert and Viko Ladelta and Panagiotis Bilalis and Jun Watanabe and Shintaro Hatanaka and Takashi Konno and Takuya Yamamoto and Kenji Tajima and Nikos Hadjichristidis and Takuya Isono and Toshifumi Satoh",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by the JSPS KAKENHI (Grant Number JP18H04639) (Hybrid Catalysis for Enabling Molecular Synthesis on Demand), Frontier Chemistry Center (Hokkaido University), Inamori Foundation, and Grant-in-Aid for JSPS Research Fellows. TS gratefully acknowledges the JSPS Fellowship for Young Scientists. VL, PB, and NH gratefully acknowledge the support of King Abdullah University of Science and Technology.",

year = "2019",

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doi = "10.1038/s41428-019-0264-6",

language = "English (US)",

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T1 - Facile synthesis of poly(trimethylene carbonate) by alkali metal carboxylate-catalyzed ring-opening polymerization

AU - Takojima, Kaoru

AU - Saito, Tatsuya

AU - Vevert, Cedric

AU - Ladelta, Viko

AU - Bilalis, Panagiotis

AU - Watanabe, Jun

AU - Hatanaka, Shintaro

AU - Konno, Takashi

AU - Yamamoto, Takuya

AU - Tajima, Kenji

AU - Hadjichristidis, Nikos

AU - Isono, Takuya

AU - Satoh, Toshifumi

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by the JSPS KAKENHI (Grant Number JP18H04639) (Hybrid Catalysis for Enabling Molecular Synthesis on Demand), Frontier Chemistry Center (Hokkaido University), Inamori Foundation, and Grant-in-Aid for JSPS Research Fellows. TS gratefully acknowledges the JSPS Fellowship for Young Scientists. VL, PB, and NH gratefully acknowledge the support of King Abdullah University of Science and Technology.

PY - 2019/9/24

Y1 - 2019/9/24

N2 - Alkali metal carboxylates, including sodium acetate, sodium benzoate, and sodium sorbate, which are all readily available and widely used as food additives, were found to promote the ring-opening polymerization (ROP) of trimethylene carbonate (TMC) to produce poly(trimethylene carbonate) (PTMC). The sodium acetate-catalyzed ROP of TMC proceeded in the presence of an alcohol initiator under solvent-free conditions at 70 °C, even at very low catalyst loadings of 0.01–0.0001 mol%. The controlled nature of this ROP system enabled the synthesis of PTMCs with predicted molecular weights ranging from 2400 to 11 700 g mol−1 and narrow dispersities (~1.23). Importantly, ROP is initiated by an alcohol initiator, allowing PTMC production with desired functional groups, such as azido, alkyne, and methacrylate groups, at the α-chain end. Furthermore, the poly(L-lactic acid)-b-PTMC-b-poly(L-lactic acid) triblock copolymer, a biodegradable thermoplastic elastomer, was successfully synthesized in one pot via the sodium acetate-catalyzed ring-opening block copolymerization of TMC and L-lactide with a 1,3-propanediol initiator.

AB - Alkali metal carboxylates, including sodium acetate, sodium benzoate, and sodium sorbate, which are all readily available and widely used as food additives, were found to promote the ring-opening polymerization (ROP) of trimethylene carbonate (TMC) to produce poly(trimethylene carbonate) (PTMC). The sodium acetate-catalyzed ROP of TMC proceeded in the presence of an alcohol initiator under solvent-free conditions at 70 °C, even at very low catalyst loadings of 0.01–0.0001 mol%. The controlled nature of this ROP system enabled the synthesis of PTMCs with predicted molecular weights ranging from 2400 to 11 700 g mol−1 and narrow dispersities (~1.23). Importantly, ROP is initiated by an alcohol initiator, allowing PTMC production with desired functional groups, such as azido, alkyne, and methacrylate groups, at the α-chain end. Furthermore, the poly(L-lactic acid)-b-PTMC-b-poly(L-lactic acid) triblock copolymer, a biodegradable thermoplastic elastomer, was successfully synthesized in one pot via the sodium acetate-catalyzed ring-opening block copolymerization of TMC and L-lactide with a 1,3-propanediol initiator.

UR - http://hdl.handle.net/10754/656920

UR - http://www.nature.com/articles/s41428-019-0264-6

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U2 - 10.1038/s41428-019-0264-6

DO - 10.1038/s41428-019-0264-6

M3 - Article

SN - 0032-3896

VL - 52

SP - 103

EP - 110

JO - Polymer Journal

JF - Polymer Journal

IS - 1

ER -

Facile synthesis of poly(trimethylene carbonate) by alkali metal carboxylate-catalyzed ring-opening polymerization

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