Enzymatic Synthesis of Biobased Polyesters Using 2,5-Bis(hydroxymethyl)furan as the Building Block

Jiao, Yi; Woortman, Albert J. J.; Ekenstein, G.O.R. Alberda van; Petrović, Dejan M.; Loos, Katja

doi:10.1021/bm500340w

Cited by 161 publications

(165 citation statements)

References 57 publications

Supporting

Mentioning

161

Contrasting

Order By: Relevance

“…9 Recent advances 17,18 in synthetic routes applied to furan polyesters allows previewing the use of more ecofriendly synthetic approaches, making use of milder conditions (in terms of temperature and catalyst). Indeed the studies published by Loos et al, 17 in 2014, and Boeriu et al 18 in 2015 reported the use of Candida antarctica lipase B and mild reaction temperatures (80 or 40 o C respectively). However, this enzymatic approach is still limited by the long reaction time involved (24-72 h), and by the low M n of the ensuing products (around 2,000 g mol -1 or less).…”

Section: Poly(ethylene 25-furandicarboxylate)mentioning

confidence: 99%

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

et al. 2015

View full text Add to dashboard Cite

Motivated by a general concern on sustainability and environmental issues, a sparkling search for renewable-based polymers has grown exponentially in recent years. This search definitely spotlighted polyesters derived from 2,5-furandicarboxylic acid, among other polymers, as some of the most promising, especially due to the resemblance of this renewable monomer to the well-known petroleum-based terephthalic acid, as well as for the possibility of preparing innovative materials. The huge number of recent papers and patents about this family of polymers explore aspects such diverse as synthesis with other renewable-based monomers, leading to the preparation of materials with enhanced thermo-mechanical, biodegradability and liquid crystalline properties, among other features. Additional aspects pursued in such studies are innovation in the synthetic approaches or its optimisation; and also the development of applications for everyday-life objects like for example packaging materials, especially bottles, textiles, coating, toners, among many other uses. Despite this intense activity little has been reviewed recently about this unique family of polyesters, or derived polymers, as the only reviews on the subject date-back from the last century. In this perspective, the present appraisal aims at contributing to fulfil this literature gap, covering recent aspects related with challenges of developing polyesters, polyamides, or other polymers from 2,5-furandicarboxylic acid and their precursors. Emphasis is placed on monomer synthesis, polymerisation reactions, catalysts and applications.A tribute to 2,5-furandicarboxylic acid excellency and the myriad of novel polyesters, but also polyamides, among other polycondensates, is comprehensively done.

show abstract

Section: Poly(ethylene 25-furandicarboxylate)mentioning

confidence: 99%

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

et al. 2015

View full text Add to dashboard Cite

show abstract

“…However, the previous studies reported by our laboratory confirmed that esters were hydrolyzed by N435 during the enzymatic polymerization of polyamides, 44 and no acid end groups were present in the oligoamides/furan-based polyesters after purification. [42][43][44] In addition, acid end groups were clearly present in PA8F which was purified in the absence of formic acid (see Figure S8 in Supporting Inforamtion).…”

Section: Instrumental Methodsmentioning

confidence: 99%

Enzymatic Polymerization of Furan-2,5-Dicarboxylic Acid-Based Furanic-Aliphatic Polyamides as Sustainable Alternatives to Polyphthalamides

Jiao¹,

Maniar²,

Woortman³

et al. 2015

Biomacromolecules

Self Cite

114

124

View full text Add to dashboard Cite

Furan-2,5-dicarboxylic acid (FDCA)-based furanic-aliphatic polyamides can be used as promising sustainable alternatives to polyphthalamides (semiaromatic polyamides) and be applied as high performance materials with great commercial interest. In this study, poly(octamethylene furanamide) (PA8F), an analog to poly(octamethylene terephthalamide) (PA8T), is successfully produced via Novozym 435 (N435)-catalyzed polymerization, using a one-stage method in toluene and a temperature-varied two-stage method in diphenyl ether, respectively. The enzymatic polymerization results in PA8F with high weight-average molecular weight (M̅(w)) up to 54000 g/mol. Studies on the one-stage enzymatic polymerization in toluene indicate that the molecular weights of PA8F increase significantly with the concentration of N435; with an optimal reaction temperature of 90 °C. The temperature-varied, two-stage enzymatic polymerization in diphenyl ether yields PA8F with higher molecular weights, as compared to the one-stage procedure, at higher reaction temperatures. MALDI-ToF MS analysis suggests that eight end groups are present in the obtained PA8F: ester/amine, ester/ester, amine/amine, acid/amine, ester/acid, acid/acid, ester/amide, and no end groups (cyclic). Compared to PA8T, the obtained PA8F possesses a similar Tg and similar crystal structures, a comparable Td, but a lower Tm.

show abstract

“…36 The use of the furandiol BHMF has been the object of the preparation of aliphatic polyesters through enzymatic catalysis. 37 Some research has recently been published dealing with furan polyesteramides. Triki et al 38 prepared amorphous polyesteramides by the melt copolycondensation of FDCA with hexamethylenediamine and ethylene glycol, giving materials with T g values increasing with increasing amide content.…”

Section: Polycondensation Systemsmentioning

confidence: 99%

Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides

et al. 2015

View full text Add to dashboard Cite

show abstract

Enzymatic Synthesis of Biobased Polyesters Using 2,5-Bis(hydroxymethyl)furan as the Building Block

Cited by 161 publications

References 57 publications

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

Enzymatic Polymerization of Furan-2,5-Dicarboxylic Acid-Based Furanic-Aliphatic Polyamides as Sustainable Alternatives to Polyphthalamides

Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides

Contact Info

Product

Resources

About