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Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust

[Image: see text] Poly(ethylene terephthalate) polyester represents the most common class of thermoplastic polymers widely used in the textile, bottling, and packaging industries. Terephthalic acid and ethylene glycol, both of petrochemical origin, are polymerized to yield the polyester. However, an...

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Autores principales: Pedersen, Simon S., Batista, Gabriel M. F., Henriksen, Martin L., Hammershøj, Hans Christian D., Hopmann, Kathrin H., Skrydstrup, Troels
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10131214/
https://www.ncbi.nlm.nih.gov/pubmed/37124285
http://dx.doi.org/10.1021/jacsau.3c00092
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author Pedersen, Simon S.
Batista, Gabriel M. F.
Henriksen, Martin L.
Hammershøj, Hans Christian D.
Hopmann, Kathrin H.
Skrydstrup, Troels
author_facet Pedersen, Simon S.
Batista, Gabriel M. F.
Henriksen, Martin L.
Hammershøj, Hans Christian D.
Hopmann, Kathrin H.
Skrydstrup, Troels
author_sort Pedersen, Simon S.
collection PubMed
description [Image: see text] Poly(ethylene terephthalate) polyester represents the most common class of thermoplastic polymers widely used in the textile, bottling, and packaging industries. Terephthalic acid and ethylene glycol, both of petrochemical origin, are polymerized to yield the polyester. However, an earlier report suggests that polymerization of methoxyterephthalic acid with ethylene glycol provides a methoxy-polyester with similar properties. Currently, there are no established biobased synthetic routes toward the methoxyterephthalic acid monomer. Here, we show a viable route to the dicarboxylic acid from various tree species involving three catalytic steps. We demonstrate that sawdust can be converted to valuable aryl nitrile intermediates through hydrogenolysis, followed by an efficient fluorosulfation–catalytic cyanation sequence (>90%) and then converted to methoxyterephthalic acid by hydrolysis and oxidation. A preliminary polymerization result indicates a methoxy-polyester with acceptable thermal properties.
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spelling pubmed-101312142023-04-27 Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust Pedersen, Simon S. Batista, Gabriel M. F. Henriksen, Martin L. Hammershøj, Hans Christian D. Hopmann, Kathrin H. Skrydstrup, Troels JACS Au [Image: see text] Poly(ethylene terephthalate) polyester represents the most common class of thermoplastic polymers widely used in the textile, bottling, and packaging industries. Terephthalic acid and ethylene glycol, both of petrochemical origin, are polymerized to yield the polyester. However, an earlier report suggests that polymerization of methoxyterephthalic acid with ethylene glycol provides a methoxy-polyester with similar properties. Currently, there are no established biobased synthetic routes toward the methoxyterephthalic acid monomer. Here, we show a viable route to the dicarboxylic acid from various tree species involving three catalytic steps. We demonstrate that sawdust can be converted to valuable aryl nitrile intermediates through hydrogenolysis, followed by an efficient fluorosulfation–catalytic cyanation sequence (>90%) and then converted to methoxyterephthalic acid by hydrolysis and oxidation. A preliminary polymerization result indicates a methoxy-polyester with acceptable thermal properties. American Chemical Society 2023-04-10 /pmc/articles/PMC10131214/ /pubmed/37124285 http://dx.doi.org/10.1021/jacsau.3c00092 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Pedersen, Simon S.
Batista, Gabriel M. F.
Henriksen, Martin L.
Hammershøj, Hans Christian D.
Hopmann, Kathrin H.
Skrydstrup, Troels
Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust
title Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust
title_full Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust
title_fullStr Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust
title_full_unstemmed Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust
title_short Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust
title_sort lignocellulose conversion via catalytic transformations yields methoxyterephthalic acid directly from sawdust
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10131214/
https://www.ncbi.nlm.nih.gov/pubmed/37124285
http://dx.doi.org/10.1021/jacsau.3c00092
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