Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization
International audience A novel method for synthesizing biobased diamide tetraol derivatives through mechanochemical processes is presented in this study. The key component used in the synthesis is (S)-gamma-hydroxymethyl-gamma-butyrolactone (2H-HBO), a cellulose-based lactone derived from levoglucos...
Published in: | Green Chemistry |
---|---|
Main Authors: | , , , , |
Other Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
HAL CCSD
2023
|
Subjects: | |
Online Access: | https://hal.science/hal-04360086 https://doi.org/10.1039/d3gc02823b |
id |
ftagroparistech:oai:HAL:hal-04360086v1 |
---|---|
record_format |
openpolar |
spelling |
ftagroparistech:oai:HAL:hal-04360086v1 2024-06-09T07:38:43+00:00 Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization Herrlé, Chloé Fadlallah, Sami Toumieux, Sylvestre Wadouachi, Anne Allais, Florent Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UR UPJV 7378 (LG2A) Université de Picardie Jules Verne (UPJV) Agro-Biotechnologies Industrielles (ABI) AgroParisTech 2023-10 https://hal.science/hal-04360086 https://doi.org/10.1039/d3gc02823b en eng HAL CCSD Royal Society of Chemistry info:eu-repo/semantics/altIdentifier/doi/10.1039/d3gc02823b hal-04360086 https://hal.science/hal-04360086 doi:10.1039/d3gc02823b ISSN: 1463-9262 EISSN: 1463-9270 Green Chemistry https://hal.science/hal-04360086 Green Chemistry, 2023, ⟨10.1039/d3gc02823b⟩ Polyether Polyols [CHIM]Chemical Sciences info:eu-repo/semantics/article Journal articles 2023 ftagroparistech https://doi.org/10.1039/d3gc02823b 2024-05-16T11:05:43Z International audience A novel method for synthesizing biobased diamide tetraol derivatives through mechanochemical processes is presented in this study. The key component used in the synthesis is (S)-gamma-hydroxymethyl-gamma-butyrolactone (2H-HBO), a cellulose-based lactone derived from levoglucosenone, combined with various linear diamines. The use of planetary ball milling in the presence of a small excess of diamine was found to be crucial for achieving complete conversion of 2H-HBO and the selective formation of diamide tetraol derivatives. The optimized parameters established for the reaction of 2H-HBO using diaminohexane were applied to biobased, non-toxic, and biodegradable diamines such as spermidine, spermine, and 4,9-dioxa-dodecanediamine. This resulted in high conversions and good yields of diamide tetraol derivatives. The scalability of the process was demonstrated by transposing the reaction from 100 mg to 2 g, with improved conversions obtained at a larger scale. The greenness of the procedure was assessed using the E-factor and EcoScale, showing low waste generation and acceptable to excellent reaction conditions. In addition, enzymatic polymerization of diamide tetraol derivatives using CAL-B (Candida antarctica lipase B) as a biocatalyst was explored. Successful polymerization of monomers obtained from hexamethylene diamine and 4,9-dioxa-dodecandiamine was achieved, providing insights into the effect of enzyme loading and monomer ratios on the molecular weight of the resulting polymers. Despite challenges with certain monomers containing amine groups, this work offers a promising approach for producing multifunctional biobased polymers.Biobased poly(ester-amide)s were synthesized from cellulose-derived levoglucosenone using mechanochemistry and enzymatic polymerization. Article in Journal/Newspaper Antarc* Antarctica AgroParisTech: HAL (Institut des sciences et industries du vivant et de l'environnement) Green Chemistry |
institution |
Open Polar |
collection |
AgroParisTech: HAL (Institut des sciences et industries du vivant et de l'environnement) |
op_collection_id |
ftagroparistech |
language |
English |
topic |
Polyether Polyols [CHIM]Chemical Sciences |
spellingShingle |
Polyether Polyols [CHIM]Chemical Sciences Herrlé, Chloé Fadlallah, Sami Toumieux, Sylvestre Wadouachi, Anne Allais, Florent Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization |
topic_facet |
Polyether Polyols [CHIM]Chemical Sciences |
description |
International audience A novel method for synthesizing biobased diamide tetraol derivatives through mechanochemical processes is presented in this study. The key component used in the synthesis is (S)-gamma-hydroxymethyl-gamma-butyrolactone (2H-HBO), a cellulose-based lactone derived from levoglucosenone, combined with various linear diamines. The use of planetary ball milling in the presence of a small excess of diamine was found to be crucial for achieving complete conversion of 2H-HBO and the selective formation of diamide tetraol derivatives. The optimized parameters established for the reaction of 2H-HBO using diaminohexane were applied to biobased, non-toxic, and biodegradable diamines such as spermidine, spermine, and 4,9-dioxa-dodecanediamine. This resulted in high conversions and good yields of diamide tetraol derivatives. The scalability of the process was demonstrated by transposing the reaction from 100 mg to 2 g, with improved conversions obtained at a larger scale. The greenness of the procedure was assessed using the E-factor and EcoScale, showing low waste generation and acceptable to excellent reaction conditions. In addition, enzymatic polymerization of diamide tetraol derivatives using CAL-B (Candida antarctica lipase B) as a biocatalyst was explored. Successful polymerization of monomers obtained from hexamethylene diamine and 4,9-dioxa-dodecandiamine was achieved, providing insights into the effect of enzyme loading and monomer ratios on the molecular weight of the resulting polymers. Despite challenges with certain monomers containing amine groups, this work offers a promising approach for producing multifunctional biobased polymers.Biobased poly(ester-amide)s were synthesized from cellulose-derived levoglucosenone using mechanochemistry and enzymatic polymerization. |
author2 |
Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UR UPJV 7378 (LG2A) Université de Picardie Jules Verne (UPJV) Agro-Biotechnologies Industrielles (ABI) AgroParisTech |
format |
Article in Journal/Newspaper |
author |
Herrlé, Chloé Fadlallah, Sami Toumieux, Sylvestre Wadouachi, Anne Allais, Florent |
author_facet |
Herrlé, Chloé Fadlallah, Sami Toumieux, Sylvestre Wadouachi, Anne Allais, Florent |
author_sort |
Herrlé, Chloé |
title |
Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization |
title_short |
Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization |
title_full |
Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization |
title_fullStr |
Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization |
title_full_unstemmed |
Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization |
title_sort |
sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization |
publisher |
HAL CCSD |
publishDate |
2023 |
url |
https://hal.science/hal-04360086 https://doi.org/10.1039/d3gc02823b |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 1463-9262 EISSN: 1463-9270 Green Chemistry https://hal.science/hal-04360086 Green Chemistry, 2023, ⟨10.1039/d3gc02823b⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1039/d3gc02823b hal-04360086 https://hal.science/hal-04360086 doi:10.1039/d3gc02823b |
op_doi |
https://doi.org/10.1039/d3gc02823b |
container_title |
Green Chemistry |
_version_ |
1801374931558072320 |