Synthesis and characterization of a renewable polyester containing oxabicyclic dicarboxylate derived from furfural

Tachibana, Yuya; Yamahata, Masayuki; Kasuya, Ken-ichi

doi:10.1039/c3gc36938b

Cited by 28 publications

(40 citation statements)

References 40 publications

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“…been synthesized from furfural, [10] 1-butanol, [33] and 5-hydrofurfural. Although commercially available MA is most often petroleum-derived, MA has Scheme 1.…”

Section: Synthesis Of Polyestersmentioning

confidence: 99%

“…Synthesis of bicyclic anhydride monomers (BCA1 and BCA2) using i) solvent-free reaction at RT and ii) H 2 with Pd/C in ethyl acetate at RT. been synthesized from furfural, [10] 1-butanol, [33] and 5-hydrofurfural. [34] Conducting the polymerizations in two stages provided homogeneous melt conditions which favored esterification and minimized sublimation of BCA1 and BCA2.…”

Section: Synthesis Of Polyestersmentioning

confidence: 99%

“…For instance, the primary alcohols on 1,3-propandediol (PDO) [10] and 1,4-butanediol (BDO) would be expected to be more reactive than the secondary hydroxyl groups on isosorbide. For instance, the primary alcohols on 1,3-propandediol (PDO) [10] and 1,4-butanediol (BDO) would be expected to be more reactive than the secondary hydroxyl groups on isosorbide.…”

Section: Introductionmentioning

confidence: 99%

“…Categorizing renewable polyols according to their flexibility, structure (cyclic versus acyclic), functionality (f n ), and type of hydroxyl group (i.e., primary, secondary) provides a convenient method for predicting reactivity, branching, and crosslinking. For instance, the primary alcohols on 1,3-propandediol (PDO) [10] and 1,4-butanediol (BDO) would be expected to be more reactive than the secondary hydroxyl groups on isosorbide. [11] Compared to diols, larger f n values have been achieved with glycerol (f n = 3), [12] soybean oil (SBO) derivatives (f n > 4), [13] soy-castor oil, [14] algal oil, [15] carvone derivatives (f n % 4-5), [16] sorbitol (f n = 6), [17] and sucrose esters (f n = 8).…”

Section: Introductionmentioning

confidence: 99%

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Diglycerol‐Based Polyesters: Melt Polymerization with Hydrophobic Anhydrides

et al. 2014

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The melt polymerization of diglycerol with bicyclic anhydride monomers derived from a naturally occurring monoterpene provides an avenue for polyesters with a high degree of sustainability. The hydrophobic anhydrides are synthesized at ambient temperature via a solvent-free Diels-Alder reaction of α-phellandrene with maleic anhydride. Subsequent melt polymerizations with tetra-functional diglycerol are effective under a range of [diglycerol]/[anhydride] ratios. The hydrophobicity of α-phellandrene directly impacts the swelling behavior of the resulting polyesters. The low E factors (<2), large amount of bio-based content (>75%), ambient temperature monomer synthesis, and polymer degradability represent key factors in the design of these sustainable polyesters.

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“…been synthesized from furfural, [10] 1-butanol, [33] and 5-hydrofurfural. Although commercially available MA is most often petroleum-derived, MA has Scheme 1.…”

Section: Synthesis Of Polyestersmentioning

confidence: 99%

Section: Synthesis Of Polyestersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Diglycerol‐Based Polyesters: Melt Polymerization with Hydrophobic Anhydrides

et al. 2014

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“…In addition to repeating unit modification reactions, cross-metathesis reactions are also used for end-capping of polymers [16]. Recently, greener approaches have been developed for polyester synthesis utilizing furfural [17] and epoxides [18].…”

Section: Introductionmentioning

confidence: 99%

Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions

Öztürk

2018

HJBC

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B u çalışmada doymamış fonksiyonel poliester türevleri 5-norbornen-2,3-dikarboksilik anhidrit ve 1,6-hekzandiol bileşiklerinin polikondenzasyon tepkimeleri ile elde edilmiştir. Fonksiyonel doymamış poliesterler metil akrilat kullanılarak halka açılma/çapraz metatez tepkimeleri ile modifiye edilmiştir. Poliesterlerin çözünürlük ve hidrofobik/hidrofilik karakterleri halka açılma/çapraz metatez tepkimeleri ile alil son grubuna sahip poli(etilenglikol) bileşikleri entegre edilerek değiştirilmiştir. Doymamış poliesterlerdeki norbornen grubu sayesinde jel benzeri malzemeler, Grubbs birinci, üçüncü ve Hoveyda-Grubbs ikinci nesil katalizörleri varlığında halka açılım metatez polimerizasyon tepkimeleri ile ana poliester zinciri üzerinde yan poli(norbornen) zincirlerinin oluşumu ile elde edilmiştir. Anahtar Kelimeler Halka açılım/çapraz metatez, poliester, rutenyum, polikondenzasyon.

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Lignocellulose Fractionation Using Recyclable Phosphoric Acid: Lignin, Cellulose, and Furfural Production

Weidener

Leitner

Marı́a³

et al. 2020

ChemSusChem

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The conversion of lignocellulose into its building blocks and their further transformation into valuable platform chemicals (e. g., furfural) are key technologies to move towards the use of renewable resources. This paper explored the disentanglement of lignocellulose into hemicellulose‐derived sugars, cellulose, and lignin in a biphasic solvent system (water/2‐methyltetrahydrofuran) using phosphoric acid as recyclable catalyst. Integrated with the biomass fractionation, in a second step hemicellulose‐derived sugars (mainly xylose) were converted to furfural, which was in situ extracted into 2‐methyltetrahydrofuran with high selectivity (70 %) and yield (56 wt %). To further increase the economic feasibility of the process, a downstream and recycling strategy enabled recovery of phosphoric acid without loss of process efficiency over four consecutive cycles. This outlines a more efficient and sustainable use of phosphoric acid as catalyst, as its inherent costs can be significantly lowered.

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Synthesis and characterization of a renewable polyester containing oxabicyclic dicarboxylate derived from furfural

Cited by 28 publications

References 40 publications

Diglycerol‐Based Polyesters: Melt Polymerization with Hydrophobic Anhydrides

Diglycerol‐Based Polyesters: Melt Polymerization with Hydrophobic Anhydrides

Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions

Lignocellulose Fractionation Using Recyclable Phosphoric Acid: Lignin, Cellulose, and Furfural Production

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