Green Chemistry

, volume 23 , issue 12 , pages 4355-4364

Synthesis of performance-advantaged polyurethanes and polyesters from biomass-derived monomers by aldol-condensation of 5-hydroxymethyl furfural and hydrogenation

Hochan Chang ^{1, 2, 3, 4, 5}

Elise B. Gilcher ^{1, 6}

George A. Huber ^{1, 2, 3, 4, 5}

James Dumesic ^{1, 2, 3, 4, 5, 6, 7}

Hide authors affiliations Show authors affiliations: 7 affiliations

Department of Chemical and Biological Engineering, University of Wisconsin–Madison, Madison, WI, USA |

Department of Chemical and Biological Engineering

University of Wisconsin–Madison |

⁴

Madison |

⁵

Usa |

⁶

DOE Great Lakes Bioenergy Research Center, University of Wisconsin–Madison, Madison, WI, USA |

⁷

DOE Great Lakes Bioenergy Research Center

Publication type: Journal Article

Publication date: 2021-04-24

Royal Society of Chemistry (RSC)

Green Chemistry

scimago Q1

wos Q1

SJR: 1.928

CiteScore: 16.1

Impact factor: 9.2

ISSN: 14639262, 14639270

DOI: 10.1039/d1gc00899d

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PubMed ID: 36275196

Environmental Chemistry

Pollution

Abstract

Functional polyurethanes and polyesters with tunable properties were synthesized from biomass-derived 5-hydroxymethyl furfural (HMF)-Acetone-HMF (HAH) monomers. HAH can be selectively hydrogenated over Cu and Ru catalysts to produce partially-hydrogenated (PHAH) and fully-hydrogenated (FHAH). The HAH units in these polymers improve the thermal stability and stiffness of the polymers compared to polyurethanes produced with ethylene glycol. Polyurethanes produced from PHAH provide diene binding sites for electron deficient C=C double bonds, such as in maleimide compounds, that can participate in Diels-Alder reactions. Such sites can function to create crosslinking by Diels-Alder coupling with bismaleimides and can be used to impart functionality to PHAH (giving rise to anti-microbial activity or controlled drug delivery). The symmetric triol structure of FHAH leads to energy-dissipating rubbers with branched structures. Accordingly, the properties of these biomass-derived polymers can be tuned by controlling the blending ratio of HAH-derived monomers or the degree of Diels-Alder reaction. The polyester produced from HAH can be used in packaging applications.

Found

1 citation

Karlinskii Bogdan

PhD in Chemistry

17 publications, 237 citations, 82 reviews

h-index: 9

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Tula State University

1 citation

Galkin Konstantin

🥼 🤝

PhD in Chemistry, associate professor

30 publications, 1 320 citations, 4 reviews

h-index: 16

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

Moscow Polytechnic University

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Chang H. et al. Synthesis of performance-advantaged polyurethanes and polyesters from biomass-derived monomers by aldol-condensation of 5-hydroxymethyl furfural and hydrogenation // Green Chemistry. 2021. Vol. 23. No. 12. pp. 4355-4364.

GOST all authors (up to 50) Copy

Chang H., Gilcher E. B., Huber G. A., Dumesic J. Synthesis of performance-advantaged polyurethanes and polyesters from biomass-derived monomers by aldol-condensation of 5-hydroxymethyl furfural and hydrogenation // Green Chemistry. 2021. Vol. 23. No. 12. pp. 4355-4364.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/d1gc00899d

UR - https://xlink.rsc.org/?DOI=D1GC00899D

TI - Synthesis of performance-advantaged polyurethanes and polyesters from biomass-derived monomers by aldol-condensation of 5-hydroxymethyl furfural and hydrogenation

T2 - Green Chemistry

AU - Chang, Hochan

AU - Gilcher, Elise B.

AU - Huber, George A.

AU - Dumesic, James

PY - 2021

DA - 2021/04/24

PB - Royal Society of Chemistry (RSC)

SP - 4355-4364

IS - 12

VL - 23

PMID - 36275196

SN - 1463-9262

SN - 1463-9270

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2021_Chang,

author = {Hochan Chang and Elise B. Gilcher and George A. Huber and James Dumesic},

title = {Synthesis of performance-advantaged polyurethanes and polyesters from biomass-derived monomers by aldol-condensation of 5-hydroxymethyl furfural and hydrogenation},

journal = {Green Chemistry},

year = {2021},

volume = {23},

publisher = {Royal Society of Chemistry (RSC)},

month = {apr},

url = {https://xlink.rsc.org/?DOI=D1GC00899D},

number = {12},

pages = {4355--4364},

doi = {10.1039/d1gc00899d}

}

MLA

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MLA Copy

Chang, Hochan, et al. “Synthesis of performance-advantaged polyurethanes and polyesters from biomass-derived monomers by aldol-condensation of 5-hydroxymethyl furfural and hydrogenation.” Green Chemistry, vol. 23, no. 12, Apr. 2021, pp. 4355-4364. https://xlink.rsc.org/?DOI=D1GC00899D.

Publisher

Royal Society of Chemistry (RSC)

Journal

Green Chemistry

scimago Q1

wos Q1

SJR

1.928

CiteScore

16.1

Impact factor

9.2

ISSN

14639262 (Print)

14639270 (Electronic)

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