Vanillin derived a carbonate dialdehyde and a carbonate diol: novel platform monomers for sustainable polymers synthesis

Bai, De; Chen, Qin; Chai, Yang; Ren, Tianhua; Huang, Caijuan; Ingram, Ian D. V.; North, Michael; Zheng, Qiang; Xie, Haibo

doi:10.1039/c8ra07185c

Cited by 20 publications

(26 citation statements)

References 59 publications

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“…Because of its phenolic −OH and aldehyde functional groups (Scheme 3), vanillin becomes a platform for the synthesis of various bio‐based polymers such as epoxy, polyester, PU, and BPHU via their epoxy, allyl, amine, carboxylic acid, and cyclic carbonate functionalization. A recent study reported carbonated vanillin monomers such as bis(4‐formyl‐2‐methoxyphenyl) carbonate (BFMC) and bis(4‐(hydroxymethyl)‐2‐methoxyphenyl) carbonate (BHMC) and their BPHU synthesis [16a] . As they are formed, polymers exhibit different material properties concerning their functionalization.…”

Section: Bio‐based Cyclic Carbonate Precursorsmentioning

confidence: 99%

“…The easier functionalization of vanillin enables the authors to achieve maximum yields after respective recrystallization using dichloromethane/hexane of BFMC and their NaBH 4 based reduction [16a] . Also, glycidylation, carbonation, allylation, alcoholization, amination, carboxylic acid functionalization of vanillin have also been reported for promising polymer synthesis [16b] …”

Section: Bio‐based Cyclic Carbonate Precursorsmentioning

confidence: 99%

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Bio‐based Poly(hydroxy urethane)s: Synthesis and Pre/Post‐Functionalization

Haniffa

Munawar

Ching

et al. 2021

Chemistry An Asian Journal

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New and emerging demand for polyurethane (PU) continues to rise over the years. The harmful isocyanate binding agents and their integrated PU products are at the height of environmental concerns, in particular PU (macro and micro) pollution and their degradation problems. Nonisocyanate poly(hydroxy urethane)s (NIPUs) are sustainable and green alternatives to conventional PUs. Since the introduction of NIPU in 1957, the market value of NIPU and its hybridized materials has increased exponentially in 2019 and is expected to continue to rise in the coming years. The secondary hydroxyl groups of these NIPU's urethane moiety have revolutionized them by allowing for adequate pre/post functionalization. This minireview highlights different strategies and advances in pre/post-functionalization used in biobased NIPU. We have performed a comprehensive evaluation of the development of new ideas in this field to achieve more efficient synthetic biobased hybridized NIPU processes through selective and kinetic understanding.

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Section: Bio‐based Cyclic Carbonate Precursorsmentioning

confidence: 99%

Section: Bio‐based Cyclic Carbonate Precursorsmentioning

confidence: 99%

Bio‐based Poly(hydroxy urethane)s: Synthesis and Pre/Post‐Functionalization

Haniffa

Munawar

Ching

et al. 2021

Chemistry An Asian Journal

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“…With the vanillin-based diol monomer in hand, we prepared polyesters and polyurethanes with diacyl chlorides and diisocyanatos, respectively according to the literature methods [20,39]. A series of polyesters were obtained via direct acylation between HMEO and acyl chlorides including oxalyl chloride (OC), succinyl chloride (SC) [40], terephthaloyl chloride (TC) [41] and 2,5-furandicarbonyl dichloride (FC) [42,43].…”

Section: Structural Analysis Of Pesmentioning

confidence: 99%

“…Meylemans et al hydrogenated vanillin to prepare 2-methoxy-4-methylphenol, which was condensed with an aldehyde under acid catalysis to give a substitute of bisphenol A, with potential utility in epoxy resins and polyurethanes [19]. Bai et al used vanillin and triphosgene to prepare a dialdehyde monomer having a carbonate structure, which can be reduced to the corresponding diol, offering great opportunities to prepare novel polyesters and polyurethanes incorporating a carbonate moiety in the main chain [20]. Zhu et al prepared a bisphenol structure via a one-pot method using vanillin, diamine and diethyl phosphite, which was then reacted with epichlorohydrin to synthesize a novel bio-based epoxy resin with excellent flame retardancy, as well as good thermal and mechanical properties [21].…”

Section: Introductionmentioning

confidence: 99%

Sustainable Aromatic Aliphatic Polyesters and Polyurethanes Prepared from Vanillin-Derived Diols via Green Catalysis

et al. 2020

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The design and preparation of polymers by using biobased chemicals is regarded as an important strategy towards a sustainable polymer chemistry. Herein, two aromatic diols, 4-(hydroxymethyl)-2-methoxyphenol and 2-(4-(hydroxymethyl)-2-methoxyphenoxy)ethanol, have been prepared in good yields through the direct reduction of vanillin and hydroxyethylated vanillin (4-(2-hydroxyethoxy)-3-methoxybenzaldehyde) using NaBH4, respectively. The diols were submitted to traditional polycondensation and polyaddition with acyl chlorides and diisocyanatos, and serials of new polyesters and polyurethanes were prepared in high yields with moderate molecular weight ranging from 17,000 to 40,000 g mol−1. Their structures were characterized by 1H NMR, 13C NMR and FTIR, and their thermal properties were studied by TGA and differential scanning calorimetry (DSC), indicating that the as-prepared polyesters and polyurethanes have Tg in the range of 16.2 to 81.2 °C and 11.6 to 80.4 °C, respectively.

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“…S and G‐type lignin degradation fragments include small phenol compounds such as vanillin and syringic acid (SA). Many studies have focused on vanillin as platform chemical for synthesizing bio‐based aromatic polymers . Fache et al extensively reviewed different functionalization strategies to create different monomers for polycondenzation and radical polymerization.…”

Section: Introductionmentioning

confidence: 99%

Linear Bio‐Based Water Soluble Aromatic Polymers from Syringic Acid, S Type Degradation Fragment from Lignin

Longe

Garnier

Saito

2020

Journal of Polymer Science

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Degradation products of lignin, a widely available biopolymer, represent the most abundant feedstock for aromatics in nature. In this work, we focused on syringic acid, derived from lignin S‐type monolignol, to synthesize different monomers for radical polymerization. The resulting polymers have molecular weight spanning over a wide range, which depends on the monomer, with up to Mn = 1,100,000 g.mol−1 and Đ = 3.0. The novel polymers exhibit a thermal stability higher than 350°C and differentiated glass transition temperatures, ranging from 105 to 120°C. One of the monomers synthesized with a free carboxyl group was able to polymerize in water—instead of organic solvent—and resulted in a water soluble polymer. Monomers from syringic acid offer a unique bio‐based alternative to oil‐based polystyrene in industry for a wider range of application. © 2020 Wiley Periodicals, Inc. J. Polym. Sci. 2020, 58, 540–547

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Vanillin derived a carbonate dialdehyde and a carbonate diol: novel platform monomers for sustainable polymers synthesis

Abstract: Novel classes of lignin-derived poly(carbonate ester)s, poly(carbonate ester)s pending amide moiety oligomers, and poly(carbonate urethane)s have been designed and synthesized.

Cited by 20 publications

References 59 publications

Bio‐based Poly(hydroxy urethane)s: Synthesis and Pre/Post‐Functionalization

Bio‐based Poly(hydroxy urethane)s: Synthesis and Pre/Post‐Functionalization

Sustainable Aromatic Aliphatic Polyesters and Polyurethanes Prepared from Vanillin-Derived Diols via Green Catalysis

Linear Bio‐Based Water Soluble Aromatic Polymers from Syringic Acid, S Type Degradation Fragment from Lignin

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