Rapid Ring-Opening Metathesis Polymerization of Monomers Obtained from Biomass-Derived Furfuryl Amines and Maleic Anhydride

Anna Blanpain; James H. Clark; Thomas J. Farmer; Yuanlong Guo; Ian D.V. Ingram; John E. Kendrick; Stefan B. Lawrenson; Michael North; George Rodgers; Adrian C. Whitwood

doi:10.1002/cssc.201900748

Rapid Ring-Opening Metathesis Polymerization of Monomers Obtained from Biomass-Derived Furfuryl Amines and Maleic Anhydride

Anna Blanpain, James H. Clark, Thomas J. Farmer, Yuanlong Guo, Ian D.V. Ingram, John E. Kendrick, Stefan B. Lawrenson, Michael North^*, George Rodgers, Adrian C. Whitwood

^*Corresponding author for this work

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

Abstract

Well-controlled and extremely rapid ring-opening metathesis polymerization of unusual oxanorbornene lactam esters by Grubbs third-generation catalyst is used to prepare a range of bio-based homo- and copolymers. Bio-derived oxanorbornene lactam monomers were prepared at room temperature from maleic anhydride and secondary furfuryl amines by using a 100 % atom economical, tandem Diels–Alder lactamization reaction, followed by esterification. Several of the resulting homo- and copolymers show good control over polymer molecular weight and have narrow molecular weight distributions.

Original language	English
Pages (from-to)	2393-2401
Number of pages	9
Journal	ChemSusChem
Volume	12
Issue number	11
Early online date	17 May 2019
DOIs	https://doi.org/10.1002/cssc.201900748
Publication status	Published - 11 Jun 2019

Bibliographical note

© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

Keywords

biomass
homogeneous catalysis
metathesis
polymerization
sustainable polymers

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10.1002/cssc.201900748

manuscript
© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.
Accepted author manuscript, 1.08 MB

Cite this

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title = "Rapid Ring-Opening Metathesis Polymerization of Monomers Obtained from Biomass-Derived Furfuryl Amines and Maleic Anhydride",

abstract = "Well-controlled and extremely rapid ring-opening metathesis polymerization of unusual oxanorbornene lactam esters by Grubbs third-generation catalyst is used to prepare a range of bio-based homo- and copolymers. Bio-derived oxanorbornene lactam monomers were prepared at room temperature from maleic anhydride and secondary furfuryl amines by using a 100 % atom economical, tandem Diels–Alder lactamization reaction, followed by esterification. Several of the resulting homo- and copolymers show good control over polymer molecular weight and have narrow molecular weight distributions.",

keywords = "biomass, homogeneous catalysis, metathesis, polymerization, sustainable polymers",

author = "Anna Blanpain and Clark, {James H.} and Farmer, {Thomas J.} and Yuanlong Guo and Ingram, {Ian D.V.} and Kendrick, {John E.} and Lawrenson, {Stefan B.} and Michael North and George Rodgers and Whitwood, {Adrian C.}",

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year = "2019",

month = jun,

day = "11",

doi = "10.1002/cssc.201900748",

language = "English",

volume = "12",

pages = "2393--2401",

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AU - Blanpain, Anna

AU - Clark, James H.

AU - Farmer, Thomas J.

AU - Guo, Yuanlong

AU - Ingram, Ian D.V.

AU - Kendrick, John E.

AU - Lawrenson, Stefan B.

AU - North, Michael

AU - Rodgers, George

AU - Whitwood, Adrian C.

N1 - © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2019/6/11

Y1 - 2019/6/11

N2 - Well-controlled and extremely rapid ring-opening metathesis polymerization of unusual oxanorbornene lactam esters by Grubbs third-generation catalyst is used to prepare a range of bio-based homo- and copolymers. Bio-derived oxanorbornene lactam monomers were prepared at room temperature from maleic anhydride and secondary furfuryl amines by using a 100 % atom economical, tandem Diels–Alder lactamization reaction, followed by esterification. Several of the resulting homo- and copolymers show good control over polymer molecular weight and have narrow molecular weight distributions.

AB - Well-controlled and extremely rapid ring-opening metathesis polymerization of unusual oxanorbornene lactam esters by Grubbs third-generation catalyst is used to prepare a range of bio-based homo- and copolymers. Bio-derived oxanorbornene lactam monomers were prepared at room temperature from maleic anhydride and secondary furfuryl amines by using a 100 % atom economical, tandem Diels–Alder lactamization reaction, followed by esterification. Several of the resulting homo- and copolymers show good control over polymer molecular weight and have narrow molecular weight distributions.

KW - biomass

KW - homogeneous catalysis

KW - metathesis

KW - polymerization

KW - sustainable polymers

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SN - 1864-5631

VL - 12

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JO - ChemSusChem

JF - ChemSusChem

IS - 11

ER -

Rapid Ring-Opening Metathesis Polymerization of Monomers Obtained from Biomass-Derived Furfuryl Amines and Maleic Anhydride

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Data supporting rapid ring-opening metathesis polymerization of monomers obtained from biomass derived furfuryl amines and maleic anhydride

Cite this

Rapid Ring-Opening Metathesis Polymerization of Monomers Obtained from Biomass-Derived Furfuryl Amines and Maleic Anhydride

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Datasets

Data supporting rapid ring-opening metathesis polymerization of monomers obtained from biomass derived furfuryl amines and maleic anhydride

Cite this