Browse
Submit Data
Databases
API
Help

Dataset Information

19 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Furan-Based Copolyesters from Renewable Resources: Enzymatic Synthesis and Properties.

ABSTRACT: Enzymatic polymerization provides an excellent opportunity for the conversion of renewable resources into polymeric materials in an effective and sustainable manner. A series of furan-based copolyesters was synthesized with Mw? up to 35?kg?mol^-1 , by using Novozyme 435 as a biocatalyst and dimethyl 2,5-furandicarboxylate (DMFDCA), 2,5-bis(hydroxymethyl)furan (BHMF), aliphatic linear diols, and diacid ethyl esters as monomers. The synthetic mechanism was evaluated by the variation of aliphatic linear monomers and their feed compositions. Interestingly, there was a significant decrease in the molecular weight if the aliphatic monomers were changed from diols to diacid ethyl esters. The obtained copolyesters were thoroughly characterized and compared with their polyester analogs. These findings provide a closer insight into the application of enzymatic polymerization techniques in designing sustainable high-performance polymers.

SUBMITTER: Maniar D

PROVIDER: S-EPMC6563708 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Furan-Based Copolyesters from Renewable Resources: Enzymatic Synthesis and Properties.

Maniar Dina D Jiang Yi Y Woortman Albert J J AJJ van Dijken Jur J Loos Katja K

ChemSusChem 20190128 5

Enzymatic polymerization provides an excellent opportunity for the conversion of renewable resources into polymeric materials in an effective and sustainable manner. A series of furan-based copolyesters was synthesized with Mw‾ up to 35 kg mol<sup>-1</sup> , by using Novozyme 435 as a biocatalyst and dimethyl 2,5-furandicarboxylate (DMFDCA), 2,5-bis(hydroxymethyl)furan (BHMF), aliphatic linear diols, and diacid ethyl esters as monomers. The synthetic mechanism was evaluated by the variation of a ...[more]

PMID: 30637973

Similar Datasets

Synthesis and Enzymatic Degradation of Sustainable Levoglucosenone-Derived Copolyesters with Renewable Citronellol Side Chains.

Project description:Recently, a renewable five-membered lactone containing citronellol (HBO-citro) was synthesized from levoglucosenone (LGO). A one-pot two-step pathway was then developed to produce a mixture of 5- and 6-membered Lactol-citro molecules (5ML and 6ML, respectively) from HBO-citro. Proton nuclear magnetic resonance (1H NMR) of a mixture of 5ML and 6ML at varying temperatures showed that the chemical shifts of the hydroxyls, as well as the 5ML:6ML ratio, are temperature-dependent. Indeed, a high temperature, such as 65 °C, led to an up-field shielding of the hydroxyl protons as well as a drop in the 5ML:6ML ratio. The monomers 5ML and 6ML were then engaged in polycondensation reactions involving diacyl chlorides. Renewable copolyesters with low glass transition temperatures (as low as -67 °C) and cross-linked citronellol chains were prepared. The polymers were then hydrolyzed using a commercial lipase from Thermomyces lanuginosus (Lipopan® 50 BG). A higher degradation rate was found for the polymers prepared using Lactol-citro molecules, compared to those obtained by the polycondensation reactions of diacyl chlorides with Triol-citro-a monomer recently obtained by the selective reduction of HBO-citro.

| S-EPMC9146931 | biostudies-literature

Poly(butylene succinate-co-ε-caprolactone) Copolyesters: Enzymatic Synthesis in Bulk and Thermal Properties.

Project description:This work explores for the first time the enzymatic synthesis of poly(butylene-co-ε-caprolactone) (PBSCL) copolyesters in bulk using commercially available monomers (dimethyl succinate (DMS), 1,4-butanediol (BD), and ε-caprolactone (CL)). A preliminary kinetic study was carried out which demonstrated the higher reactivity of DMS over CL in the condensation/ring opening polymerization reaction, catalyzed by Candida antarctica lipase B. PBSCL copolyesters were obtained with high molecular weights and a random microstructure, as determined by 13C NMR. They were thermally stable up to 300 °C, with thermal stability increasing with the content of CL in the copolyester. All of them were semicrystalline, with melting temperatures and enthalpies decreasing up to the eutectic point observed at intermediate compositions, and glass transition temperatures decreasing with the content of CL in the copolyester. The use of CALB provided copolyesters free from toxic metallic catalyst, which is very useful if the polymer is intended to be used for biomedical applications.

| S-EPMC8401440 | biostudies-literature

Tandem synthesis of alternating polyesters from renewable resources.

Project description:The vast majority of commodity materials are obtained from petrochemical feedstocks. These resources will plausibly be depleted within the next 100 years, and the peak in global oil production is estimated to occur within the next few decades. In this regard, biomass represents an abundant carbon-neutral renewable resource for the production of polymers. Here we report a new strategy, based on tandem catalysis, to obtain renewable materials. Commercially available complexes are found to be efficient catalysts for alternating polyesters from the cyclization of dicarboxylic acids followed by alternating copolymerization of the resulting anhydrides with epoxides. This operationally simple method is an attractive strategy for the production of new biodegradable polyesters.

| S-EPMC3247812 | biostudies-other

Synthesis, Structure, Crystallization and Mechanical Properties of Isodimorphic PBS-ran-PCL Copolyesters.

Project description:Isodimorphic behavior is determined by partial inclusion of comonomer segments within the crystalline structure and arises from the comparatively similar repeating chain units of the parental homopolymers. Isodimorphic random copolymers are able to crystallize irrespective of their composition and exhibit a pseudo-eutectic behavior when their melting point values are plotted as a function of comonomer content. At the pseudo-eutectic point or region, two crystalline phases can coexist. On the right-hand and the left-hand side of the pseudo-eutectic point or region, only one single crystalline phase can form which is very similar to the crystalline structures of the parent homopolymers. This article aims to study the synthesis method, structure, crystallization behavior and mechanical properties of isodimorphic random PBS-ran-PCL copolyesters. Moreover, this study provides a comprehensive analysis of our main recent results on PBS-ran-PCL random copolyesters with three different molecular weights. The results show that the comonomer composition and crystallization conditions are the major factors responsible for the crystalline morphology, crystallization kinetics and mechanical performance of isodimorphic random copolyesters. Our studies demonstrate that in the pseudo-eutectic region, where both crystalline phases can coexist, the crystallization conditions determine the crystalline phase or phases of the copolymer. The relationships between the comonomer composition and mechanical properties are also addressed in this work.

| S-EPMC8309441 | biostudies-literature

Partially Renewable Poly(butylene 2,5-furandicarboxylate-co-isophthalate) Copolyesters Obtained by ROP.

Project description:Cyclic butylene furandicarboxylate (c(BF)n) and butylene isophthalate (c(BI)n) oligomers obtained by high dilution condensation reaction were polymerized in bulk at 200 °C with Sn(Oct)₂ catalyst via ring opening polymerization to give homopolyesters and copolyesters (coPBFxIy) with weight average molar masses in the 60,000⁻70,000 g·mol-1 range and dispersities between 1.3 and 1.9. The composition of the copolyesters as determined by NMR was practically the same as that of the feed, and they all showed an almost random microstructure. The copolyesters were thermally stable up to 300 °C and crystalline for all compositions, and have Tg in the 40⁻20 °C range with values decreasing almost linearly with their content in isophthalate units in the copolyester. Both melting temperature and enthalpy of the copolyesters decreased as the content in butylene isophthalate units increased up to a composition 30/70 (BF/BI), at which the triclinic crystal phase made exclusively of butylene furanoate units changed to the crystal structure of PBI. The partial replacement of furanoate by isophthalate units decreased substantially the crystallizability of PBF.

| S-EPMC6415514 | biostudies-literature

Supramolecular Gel Formation Based on Glycolipids Derived from Renewable Resources.

Project description:The potential applications of self-assembled supramolecular gels based on natural molecules encouraged the researchers to develop a versatile synthetic method for their structural analogues. Herein, we report a facile synthesis of glycolipid from renewable resources, cashew nut shell liquid,d and d-glucose in good yield. Gelation behavior of these glycolipids were studied in a wide range of solvents and oils. To our delight, compound 5b formed a hydrogel with Critical gelator concentration (CGC) of 0.29% w/v. Morphological analysis of the hydrogel depicts the formation of twisted fibers with an entangled network. Formation of a twisted fibrous structure was further identified by CD spectral studies with respect to temperature. The molecular self-assembly assisted by hydrogen bonding, hydrophobic, and ??? stacking interactions were identified by X-ray diffraction (XRD) and FTIR studies. Rheological analysis depicted the mechanical strength and stability of the hydrogel, which is crucial in predicting the practical applications of supramolecular soft materials.

| S-EPMC6318777 | biostudies-literature

Ester Oils Prepared from Fully Renewable Resources and Their Lubricant Base Oil Properties.

Project description:The work reports on the physicochemical and tribological properties of gallate ester oils prepared from fully renewable resources, such as gallic acid and fatty acids. The ester structures were identified by proton nuclear magnetic resonance spectroscopy (1H NMR), carbon nuclear magnetic resonance spectroscopy (13C NMR) and high-resolution mass spectra (HRMS) data. The density at 20 °C (d 20), kinematic viscosity (KV), viscosity index (VI), pour point (PP), flash point (FP), thermal and oxidative stabilities, friction-reducing and antiwear properties of gallate ester oils were evaluated. The tribological properties of gallate ester oils as lubricants for steel, copper, and aluminum tribo-pairs can be compared with those of the commercially available lubricating oil tris(2-ethylhexyl) trimellitate (Phe-3Ci8), but their viscosity-temperature characteristics, thermal and oxidative stabilities are better than those of Phe-3Ci8. More importantly, they have much higher biodegradabilities than Phe-3Ci8. The study of the lubrication mechanism shows that the physical and/or chemical adsorption film formed by gallate ester molecules between friction pairs is the key factor for them to obtain friction-reducing and antiwear properties.

| S-EPMC8246460 | biostudies-literature

Microwave-Assisted Syntheses in Recyclable Ionic Liquids: Photoresists Based on Renewable Resources.

Project description:The copoly(2-oxazoline) pNonOx80 -stat-pDc(=) Ox20 can be synthesized from the cationic ring-opening copolymerization of 2-nonyl-2-oxazoline NonOx and 2-dec-9'-enyl-2-oxazoline Dc(=) Ox in the ionic liquid n-hexyl methylimidazolium tetrafluoroborate under microwave irradiation in 250 g/batch quantities. The polymer precipitates upon cooling, enabling easy recovery of the polymer and the ionic liquid. Both monomers can be obtained from fatty acids from renewable resources. pNonOx80 -stat-pDc(=) Ox20 can be used as polymer in a photoresist (resolution of 1 μm) based on UV-induced thiol-ene reactions.

| S-EPMC4641455 | biostudies-literature

Bio-based Aromatic Copolyesters: Influence of Chemical Microstructures on Thermal and Crystalline Properties.

Project description:Aromatic copolyesters, derived from bio-based nipagin and eugenol, were synthesized with renewable 1,6-hexandiol as the spacer. Number-average, weight-average molecular weights (Mn, Mw), and polydispersity (D) values were determined by size exclusion chromatography (SEC). Chemical structures were confirmed by 1H NMR and 13C NMR spectroscopies. Chemical microstructure analysis suggested that the nipagin and eugenol-derived units were inserted into polymer chains in an arbitrary manner. Due to the short chain of 1,6-hexanediol, the splitting of magnetically different methylene carbons, adjacent to the alcohol-oxygens, proved to be more sensitive towards sequence distributions, at the dyed level, than those from 1,10-decanediol. Thermal gravimetric analysis (TGA) demonstrated that these polyester materials have excellent thermal stability (> 360 °C), regardless of the content of eugenol-derived composition incorporated. Differential scanning calorimetric (DSC) and wide-angle X-ray diffraction (WXRD) experiments revealed the semicrystalline nature for this kind of copolyesters. The crystallinities gradually decreased with the increase of eugenol-derived composition. Thermal and crystalline properties were well discussed from the microscopic perspective. The point of this work lies in establishing guidance for future design and modification of high-performance polymer materials from the microscopic perspective.

| S-EPMC7240576 | biostudies-literature

Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans.

Project description:An important advance in fluid surface control was the amphiphilic surfactant composed of coupled molecular structures (i.e., hydrophilic and hydrophobic) to reduce surface tension between two distinct fluid phases. However, implementation of simple surfactants has been hindered by the broad range of applications in water containing alkaline earth metals (i.e., hard water), which disrupt surfactant function and require extensive use of undesirable and expensive chelating additives. Here we show that sugar-derived furans can be linked with triglyceride-derived fatty acid chains via Friedel-Crafts acylation within single layer (SPP) zeolite catalysts. These alkylfuran surfactants independently suppress the effects of hard water while simultaneously permitting broad tunability of size, structure, and function, which can be optimized for superior capability for forming micelles and solubilizing in water.

| S-EPMC5126714 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data