Synthesis, Life Cycle Assessment, and Polymerization of a Vanillin-Based Spirocyclic Diol toward Polyesters with Increased Glass-Transition Temperature

Mankar, Smita V.; Gonzalez, Nelly Garcia; Warlin, Niklas; Valsange, Nitin G.; Rehnberg, Nicola; Lundmark, Stefan; Jannasch, Patric; Zhang, Baozhong

doi:10.1021/acssuschemeng.9b04930

Cited by 66 publications

(66 citation statements)

References 80 publications

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“…The T g and M n of PBSFs compared with poly(1,4‐cyclohexanedimethylene furandicarboxylate) (PCF), 69 PEF, 20,31,66,67,69,70 PPF, 26,28,31 poly(isosorbide cyclohexane dicarboxylate) (PCI), 46 poly(butylene 2,4:3,5‐Di‐O‐methylene‐D‐mannitol terephthalate) (PBManxT), 50 poly(ethylene‐1,4‐cyclohexyldimethylene‐isosorbide terephthalate) (PEICT), 71 poly(isoidide‐2,5‐bismethylene terephthalate) (PXIIT), 72 PHVT, 73 poly(ethylene 1,4‐cyclohexanedione glycerol diketal 2,5‐furandicarboxylate) (PCHDF) 74 [Color figure can be viewed at wileyonlinelibrary.com]…”

Section: Resultsmentioning

confidence: 99%

Completely amorphous high thermal resistant copolyesters from bio‐based 2,5‐furandicarboxylic acid

Shen

Wang

et al. 2021

J of Applied Polymer Sci

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Polyesters from renewable resources with glass transition temperature (T g) higher than 100 C are crucial in broadening their application range. In this work, a series of high molecular weight copolyesters, poly(butylene bis [4-(2-hydroxyethoxy) phenyl] sulfone 2,5-furandicarboxylate) (PBSF), was synthesized from bis[4-(2-hydroxyethoxy) phenyl] sulfone (BHEPS), bio-based 1,4-butanediol (BDO), and 2,5-furandicarboxylic acid (FDCA) via transesterification. Nuclear magnetic resonance spectroscopy (1 H-NMR and 13 C-NMR) was used to confirm their chemical structures, composition, and sequence distribution. Characterizations demonstrated that with the increasing content of BHEPS unit, T g of synthesized polyesters was increased from 38.2 C for PBF to 122 C for PBSF-95, in which the content of BHEPS unit was 95%. However, the weight average molecular weight (M w) of PBSF was dramatically decreased after the addition of BHEPS, from 95,300 g/mol for PBF to only 9600 g/mol for PBSF-95, which was too low for practical application. Taking molecular weight, T g , and mechanical properties into account, PBSF-65 was considered to be a promising polyester with M w of 28,500 g/mol, T g of 104.7 C, tensile strength of 82 MPa, and elongation-at-break of 98%. Besides, it was a completely amorphous polyester with a transmittance of 89.9% by cutoff at 700 nm. Summarily, PBSF-65 showed great potential to be used as raw material for the manufacture of baby bottles, children's toys, kitchen appliances, and beverage packaging, especially in the case when high transparency and heat resistance are required.

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Section: Resultsmentioning

confidence: 99%

Completely amorphous high thermal resistant copolyesters from bio‐based 2,5‐furandicarboxylic acid

Shen

Wang

et al. 2021

J of Applied Polymer Sci

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“…In another piece of work, Mankar et al synthesized a spiro-diol by acetal formation in a reaction of pentaerythritol with two equivalents of vanillin. 25 Incorporation of this rigid spiro-cyclic diol in copolyesters produced from 1,6-hexanediol and dimethyl terephthalate resulted in improved T g and thermal stability. 25 Hence, this gave materials similar to Akestra™, a commercial fossil-based high-performance polyester produced from a spiro-diol, ethylene glycol and terephthalic acid.…”

Section: Introductionmentioning

confidence: 99%

“…25 Incorporation of this rigid spiro-cyclic diol in copolyesters produced from 1,6-hexanediol and dimethyl terephthalate resulted in improved T g and thermal stability. 25 Hence, this gave materials similar to Akestra™, a commercial fossil-based high-performance polyester produced from a spiro-diol, ethylene glycol and terephthalic acid. 26 Using a similar strategy, Warlin and coworkers reported the synthesis of a rigid spirodiol from pentaerythritol and two equivalents of fructosebased 5-hydroxymethylfurfural.…”

Section: Introductionmentioning

confidence: 99%

Rigid biobased polycarbonates with good processability based on a spirocyclic diol derived from citric acid

et al. 2020

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“…It has been reported that 2,2′-bifuran-5,5′-dicarboxylic acid (BFDCA) can be used as a precursor for novel bio-based polyamides and polyesters [40][41][42]. Derived from furfural, BFDCA is a C10 biheteroaryl monomer useful in the synthesis of new polymers [43][44][45][46].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of amides and esters containing furan rings under microwave-assisted conditions

2021

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In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO− or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl)furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5-dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furandicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.

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Synthesis, Life Cycle Assessment, and Polymerization of a Vanillin-Based Spirocyclic Diol toward Polyesters with Increased Glass-Transition Temperature

Cited by 66 publications

References 80 publications

Completely amorphous high thermal resistant copolyesters from bio‐based 2,5‐furandicarboxylic acid

Completely amorphous high thermal resistant copolyesters from bio‐based 2,5‐furandicarboxylic acid

Rigid biobased polycarbonates with good processability based on a spirocyclic diol derived from citric acid

Synthesis of amides and esters containing furan rings under microwave-assisted conditions

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