TY - JOUR
T1 - Production of 2,5‐furandicarboxylic acid methyl esters from pectin‐based aldaric acid
T2 - From laboratory to bench scale
AU - Van strien, Nicolaas
AU - Niskanen, Jukka
AU - Berghuis, Anneloes
AU - Pöhler, Holger
AU - Rautiainen, Sari
PY - 2024/1/8
Y1 - 2024/1/8
N2 - 2,5-furandicarboxylic acid (FDCA) is one of the most attractive emerging renewable monomers, which has gained interest especially in polyester applications, such as the production of polyethylene furanoate (PEF). Recently, the attention has shifted towards FDCA esters due to their better solubility as well as the easier purification and polymerisation compared to FDCA. In our previous work, we reported the synthesis of FDCA butyl esters by dehydration of aldaric acids as stable intermediates. Here, we present the synthesis of FDCA methyl esters in high yields from pectin-based galactaric acid using a solid acid catalyst. The process enables high substrate concentrations (up to 20 wt%) giving up to 50 mol% FDCA methyl esters with total furancarboxylates yields of up to 90 mol%. The synthesis was successfully scaled up from gram-scale to kilogram-scale in batch reactors showing the feasibility of the process. The stability of the catalyst was tested in re-use experiments. Purification of the crude product by vacuum distillation and precipitation gave furan-2,5-dimethylcarboxylate with a 98% purity.
AB - 2,5-furandicarboxylic acid (FDCA) is one of the most attractive emerging renewable monomers, which has gained interest especially in polyester applications, such as the production of polyethylene furanoate (PEF). Recently, the attention has shifted towards FDCA esters due to their better solubility as well as the easier purification and polymerisation compared to FDCA. In our previous work, we reported the synthesis of FDCA butyl esters by dehydration of aldaric acids as stable intermediates. Here, we present the synthesis of FDCA methyl esters in high yields from pectin-based galactaric acid using a solid acid catalyst. The process enables high substrate concentrations (up to 20 wt%) giving up to 50 mol% FDCA methyl esters with total furancarboxylates yields of up to 90 mol%. The synthesis was successfully scaled up from gram-scale to kilogram-scale in batch reactors showing the feasibility of the process. The stability of the catalyst was tested in re-use experiments. Purification of the crude product by vacuum distillation and precipitation gave furan-2,5-dimethylcarboxylate with a 98% purity.
KW - renewable resources
KW - heterogeneous catalysis
KW - furanoics
KW - scale-up
KW - green chemistry
UR - http://www.scopus.com/inward/record.url?scp=85173455203&partnerID=8YFLogxK
U2 - 10.1002/cssc.202300732
DO - 10.1002/cssc.202300732
M3 - Article
SN - 1864-5631
VL - 17
JO - ChemSusChem
JF - ChemSusChem
IS - 1
M1 - e202300732
ER -