Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties
2,5-Furandicarboxylic acid (FDCA)-based semi-aromatic polyamides are novel biobased alternatives to petrol-based semi-aromatic polyamides (polyphthalamides), that have a broad commercial interest as engineering thermoplastics and high performance materials. In this study, a series of FDCA-based semi...
Published in: | RSC Advances |
---|---|
Main Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2016
|
Subjects: | |
Online Access: | https://hdl.handle.net/11370/440ee0fe-571c-4c15-a971-a6d4b542b48d https://research.rug.nl/en/publications/440ee0fe-571c-4c15-a971-a6d4b542b48d https://doi.org/10.1039/c6ra14585j https://pure.rug.nl/ws/files/49615010/Enzymatic_synthesis_of_2_5_furandicarboxylic_acid_based.pdf |
id |
ftunigroningenpu:oai:pure.rug.nl:publications/440ee0fe-571c-4c15-a971-a6d4b542b48d |
---|---|
record_format |
openpolar |
spelling |
ftunigroningenpu:oai:pure.rug.nl:publications/440ee0fe-571c-4c15-a971-a6d4b542b48d 2024-06-02T07:55:58+00:00 Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties Jiang, Yi Maniar, Dina Woortman, Albert J. J. Loos, Katja 2016 application/pdf https://hdl.handle.net/11370/440ee0fe-571c-4c15-a971-a6d4b542b48d https://research.rug.nl/en/publications/440ee0fe-571c-4c15-a971-a6d4b542b48d https://doi.org/10.1039/c6ra14585j https://pure.rug.nl/ws/files/49615010/Enzymatic_synthesis_of_2_5_furandicarboxylic_acid_based.pdf eng eng https://research.rug.nl/en/publications/440ee0fe-571c-4c15-a971-a6d4b542b48d info:eu-repo/semantics/openAccess Jiang , Y , Maniar , D , Woortman , A J J & Loos , K 2016 , ' Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides : enzymatic polymerization kinetics, effect of diamine chain length and thermal properties ' , RSC Advances , vol. 6 , 67941 , pp. 67941-67953 . https://doi.org/10.1039/c6ra14585j LIPASE-CATALYZED SYNTHESIS RENEWABLE RESOURCES FURAN-2,5-DICARBOXYLIC ACID ALIPHATIC POLYESTERS BUILDING-BLOCK DICARBONSAUREN POLYMERS MONOMERS AMINES UNITS article 2016 ftunigroningenpu https://doi.org/10.1039/c6ra14585j 2024-05-07T19:52:44Z 2,5-Furandicarboxylic acid (FDCA)-based semi-aromatic polyamides are novel biobased alternatives to petrol-based semi-aromatic polyamides (polyphthalamides), that have a broad commercial interest as engineering thermoplastics and high performance materials. In this study, a series of FDCA-based semi-aromatic polyamides is successfully produced via Novozym (R) 435 (N435, an immobilized form of Candida antarctica lipase b (CALB))-catalyzed polycondensation of (potentially) biobased dimethyl 2,5-furandicarboxylate and aliphatic diamines differing in chain length (C4-C12), using a one-stage method at 90 degrees C in toluene. The obtained polyamides reach high weight-average molecular weights ranging from 15 800 to 48 300 g mol(-1); and N435 shows the highest selectivity towards 1,8-octanediame (C8). MALDI-ToF MS analysis indicates that no byproducts are formed during the enzymatic polymerization. Study of the kinetics of the enzymatic polymerization suggests that phase separation of FDCA-based oligoamides/polyamides takes place in the early stage of polymerization, and the isolated products undergo an enzyme-catalyzed solid-state polymerization. However, the isolation yields of the purified products from the enzymatic polymerizations are less than similar to 50% due to the production of a large amount of low molecular weight products that are washed away during the purification steps. Furthermore, the thermal properties of the enzymatic FDCA-based semi-aromatic polyamides are carefully investigated, and compared to those of the FDCA-based and petrol-based counterparts produced via conventional synthesis techniques as reported in literature. Article in Journal/Newspaper Antarc* Antarctica University of Groningen research database RSC Advances 6 72 67941 67953 |
institution |
Open Polar |
collection |
University of Groningen research database |
op_collection_id |
ftunigroningenpu |
language |
English |
topic |
LIPASE-CATALYZED SYNTHESIS RENEWABLE RESOURCES FURAN-2,5-DICARBOXYLIC ACID ALIPHATIC POLYESTERS BUILDING-BLOCK DICARBONSAUREN POLYMERS MONOMERS AMINES UNITS |
spellingShingle |
LIPASE-CATALYZED SYNTHESIS RENEWABLE RESOURCES FURAN-2,5-DICARBOXYLIC ACID ALIPHATIC POLYESTERS BUILDING-BLOCK DICARBONSAUREN POLYMERS MONOMERS AMINES UNITS Jiang, Yi Maniar, Dina Woortman, Albert J. J. Loos, Katja Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties |
topic_facet |
LIPASE-CATALYZED SYNTHESIS RENEWABLE RESOURCES FURAN-2,5-DICARBOXYLIC ACID ALIPHATIC POLYESTERS BUILDING-BLOCK DICARBONSAUREN POLYMERS MONOMERS AMINES UNITS |
description |
2,5-Furandicarboxylic acid (FDCA)-based semi-aromatic polyamides are novel biobased alternatives to petrol-based semi-aromatic polyamides (polyphthalamides), that have a broad commercial interest as engineering thermoplastics and high performance materials. In this study, a series of FDCA-based semi-aromatic polyamides is successfully produced via Novozym (R) 435 (N435, an immobilized form of Candida antarctica lipase b (CALB))-catalyzed polycondensation of (potentially) biobased dimethyl 2,5-furandicarboxylate and aliphatic diamines differing in chain length (C4-C12), using a one-stage method at 90 degrees C in toluene. The obtained polyamides reach high weight-average molecular weights ranging from 15 800 to 48 300 g mol(-1); and N435 shows the highest selectivity towards 1,8-octanediame (C8). MALDI-ToF MS analysis indicates that no byproducts are formed during the enzymatic polymerization. Study of the kinetics of the enzymatic polymerization suggests that phase separation of FDCA-based oligoamides/polyamides takes place in the early stage of polymerization, and the isolated products undergo an enzyme-catalyzed solid-state polymerization. However, the isolation yields of the purified products from the enzymatic polymerizations are less than similar to 50% due to the production of a large amount of low molecular weight products that are washed away during the purification steps. Furthermore, the thermal properties of the enzymatic FDCA-based semi-aromatic polyamides are carefully investigated, and compared to those of the FDCA-based and petrol-based counterparts produced via conventional synthesis techniques as reported in literature. |
format |
Article in Journal/Newspaper |
author |
Jiang, Yi Maniar, Dina Woortman, Albert J. J. Loos, Katja |
author_facet |
Jiang, Yi Maniar, Dina Woortman, Albert J. J. Loos, Katja |
author_sort |
Jiang, Yi |
title |
Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties |
title_short |
Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties |
title_full |
Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties |
title_fullStr |
Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties |
title_full_unstemmed |
Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties |
title_sort |
enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides:enzymatic polymerization kinetics, effect of diamine chain length and thermal properties |
publishDate |
2016 |
url |
https://hdl.handle.net/11370/440ee0fe-571c-4c15-a971-a6d4b542b48d https://research.rug.nl/en/publications/440ee0fe-571c-4c15-a971-a6d4b542b48d https://doi.org/10.1039/c6ra14585j https://pure.rug.nl/ws/files/49615010/Enzymatic_synthesis_of_2_5_furandicarboxylic_acid_based.pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Jiang , Y , Maniar , D , Woortman , A J J & Loos , K 2016 , ' Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides : enzymatic polymerization kinetics, effect of diamine chain length and thermal properties ' , RSC Advances , vol. 6 , 67941 , pp. 67941-67953 . https://doi.org/10.1039/c6ra14585j |
op_relation |
https://research.rug.nl/en/publications/440ee0fe-571c-4c15-a971-a6d4b542b48d |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1039/c6ra14585j |
container_title |
RSC Advances |
container_volume |
6 |
container_issue |
72 |
container_start_page |
67941 |
op_container_end_page |
67953 |
_version_ |
1800752386235432960 |