Conditions to Control Furan Ring Opening during Furfuryl Alcohol Polymerization

The chemistry of biomass-derived furans is particularly sensitive to ring openings. These side reactions occur during furfuryl alcohol polymerization. In this work, the furan ring-opening was controlled by changing polymerization conditions, such as varying the type of acidic initiator or the water...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 27; no. 10; p. 3212
Main Authors: Quinquet, Lucie, Delliere, Pierre, Guigo, Nathanael
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 17.05.2022
MDPI
Subjects:
Acids
Alcohol
biobased poly(furfuryl alcohol)
Cellulose
Chemical Sciences
degree of open structures
Esters
Furans - chemistry
Investigations
Iodine
Lignin
Phenols
Polymerization
ring-opening
Spectroscopy, Fourier Transform Infrared
Water
ring-opening
biobased poly(furfuryl alcohol)
degree of open structures
ISSN:1420-3049, 1420-3049
Online Access:Get full text
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Summary:The chemistry of biomass-derived furans is particularly sensitive to ring openings. These side reactions occur during furfuryl alcohol polymerization. In this work, the furan ring-opening was controlled by changing polymerization conditions, such as varying the type of acidic initiator or the water content. The degree of open structures (DOS) was determined by quantifying the formed carbonyl species by means of quantitative 19F NMR and potentiometric titration. The progress of polymerization and ring opening were monitored by DSC and FT-IR spectroscopy. The presence of additional water is more determining on ring opening than the nature of the acidic initiator. Qualitative structural assessment by means of 13C NMR and FT-IR shows that, depending on the employed conditions, poly(furfuryl alcohol) samples can be classified in two groups. Indeed, either more ester or more ketone side groups are formed as a result of side ring opening reactions. The absence of additional water during FA polymerization preferentially leads to opened structures in the PFA bearing more ester moieties.
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These authors contributed equally to this work.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27103212