Catechol production from lignin by Al-doped mesoporous silica catalytic cracking

Jeenpadiphat, Sirima; Mongkolpichayarak, Isara; Tungasmita, Duangamol Nuntasri

doi:10.1016/j.jaap.2016.08.011

Cited by 17 publications

(7 citation statements)

References 29 publications

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“…Nevertheless, to the best of our knowledge, there are still no reports in the scientific literature on the synthesis of bis-benzoxazines starting from catechol ( CT ). Chemically described as 1,2-dihydroxybenzene, CT is a renewable raw material that can be obtained from lignin by different chemical processes. − Recent results published by Dumas and co-workers, addressing the synthesis of bis-benzoxazines based on resorcinol and hydroquinone, indicate catechol as a promising alternative renewable starting material for the synthesis of high-performance polymers.…”

Section: Introductionmentioning

confidence: 99%

Development of Fully Biobased High-Performance Bis-Benzoxazine under Environmentally Friendly Conditions

Kotzebue

Oliveira

Silva

et al. 2018

ACS Sustainable Chem. Eng.

117

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Environmental concerns are driving scientists in a quest for more sustainable products and processes. In the development of bis-benzoxazines, a novel class of thermosetting resins, which are receiving considerable attention from academia and industry, bisphenol A (BPA) and toxic solvents are still drawbacks that need to be overcome. Renewable feedstocks, neoteric solvents, and energy-efficient heating sources are sophisticated alternative solutions to the current traditional methodologies. In the current study, an eco-friendly approach to a fully biobased thermosetting resin from lignocellulose-derived products is reported. Catechol and furfurylamine are successfully fused into bis-benzoxazines in only a few minutes under microwave irradiation in the presence of poly(ethylene glycol) as solvent. The workup procedure requires minimum amounts of methanol for complete purification of the product in good yields, which is characterized by Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), and 1 H and 13 C nuclear magnetic resonance spectroscopy (NMR). As used in the development of high-performance polymers, novel copolymerized polybenzoxazines are evaluated by thermogravimetric analysis (TGA) and dynamic mechanical analysis (DMA).

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Section: Introductionmentioning

confidence: 99%

Development of Fully Biobased High-Performance Bis-Benzoxazine under Environmentally Friendly Conditions

Kotzebue

Oliveira

Silva

et al. 2018

ACS Sustainable Chem. Eng.

117

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“…As inspired by these phenomena, we reported herein a route to synthesize liquid lignin-containing epoxy prepolymers (Figure ). First, lignin was phenolated by catechol, a renewable building block that is available from lignin through demethylation of lignin-derived guaiacol or by lignin pyrolysis. − Compared to phenol, catechol is more reactive for phenolation and has increased number of hydroxyl group and phenolic para/ortho site for condensation . Second, phenolated lignin was condensed with salicyl alcohol (SA, a renewable compound that can be derived from willow bark) to yield lignin-incorporated novolac oligomers (PL-SA), with PL content could reach up to 40 wt %.…”

Section: Introductionmentioning

confidence: 99%

Formaldehyde-Free Method for Incorporating Lignin into Epoxy Thermosets

Zhao

Huang

Whelton

et al. 2018

ACS Sustainable Chem. Eng.

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A series of liquid and curable lignin-containing epoxy prepolymers were prepared for making renewable epoxy thermosets. First, lignin was modified to phenolated lignin (PL) in a solvent-free reaction. PL was subsequently co-oligomerized with salicyl alcohol (SA) in water without the use of formaldehyde to obtain fully bio-based polyphenols (PL-SA). Glycidylation of lignin-based polyphenols yielded exclusively liquid epoxy prepolymers without production of solid co-products. The liquid epoxy prepolymers (with lignin content up to 21 wt %) were curable with amine hardener (diethylenetriamine) to generate homogeneous thermosets, which required no epoxy co-prepolymer. The structural evolution from starting monomers to epoxy thermosets was followed by nuclear magnetic resonance and Fourier transform infrared spectroscopy. Compared to common syntheses in which lignin is glycidylated prior to being blended with epoxy co-prepolymers, the herein reported methodology conferred networks with increased α-relaxation temperature (106–114 vs 96 °C), storage modulus (1843–2151 vs 1828 MPa), cross-link density (8.2–16.0 vs 5.4 mmol/cm3) and tensile properties (stress of 66.9–68.1 vs 28.7 MPa, and strain of 3.3–3.7 vs 1.4%). Moreover, bio-based thermosets exhibited comparable or superior thermomechanical properties to conventional bisphenol A (BPA)-based counterpart. By producing liquid-phase lignin-containing epoxy prepolymers, this study provides a formaldehyde-free method for incorporating lignin into epoxy thermosets without the need for additional co-prepolymers.

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“…Me γ-valerolactone from levulinic acid through catalytic hydrogenation (>99%), [118] lignocellulose [119] P O H O furfural pentose-containing biomass like corn cobs, sugar cane residues, [97,109,111,120] wood hydrosylates [121] S O Me 2-methyltetrahydrofuran hydrogenation of furfural [122] P O OH Me caproic acid wv, [65] fractionation of coconut oil [69] S HO OH OH OH OH OH sorbitol hydrogenation of glucose [75] , from cellulose (up to 85%) [31,75] S HO OH OH OH OH OH mannitol juice of manna-ash (Fraxinus ornus l.), olive trees/leaves, [123][124] catalytic hydrogenation of glucosefructose mixtures or cellulose (up to 85%) [75] P OH OH catechol dry distillation of Acacia catechu, [125] lignin [126][127] P OH phenol lignin depol., [128] pine wood lignin (9.6 mol%) [129] P OH HO resorcinol wood tar [130] S OH OH HO phloroglucinol from phloretin [131] (apple tree leaves, manchurian apricot) [132][133] Compound Natural source…”

Section: P O Omentioning

confidence: 99%