Vanillin-derived epoxy monomer for synthesis of bio-based epoxy thermosets: effect of functionality on thermal, mechanical, chemical and structural properties

Mogheiseh, Mohsen; Karimian, Ramin; Khoshsefat, Mostafa

doi:10.1007/s11696-020-01164-8

Cited by 8 publications

(5 citation statements)

References 35 publications

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“…1 ). The interest in VA comes from its use as intermediate in the synthesis of bioactive compounds, such as capsaicinoids (Sudhakar Johnson et al ., 1996 ; Anderson et al ., 2014 ; Arce‐Rodríguez and Ochoa‐Alejo, 2019 ), and as a precursor for the production of polyepoxides (Fache et al ., 2015 ; Mogheiseh et al ., 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Metabolic engineering of Pseudomonas putida for production of vanillylamine from lignin‐derived substrates

Manfrão-Netto

Lund

Muratovska

et al. 2021

Microbial Biotechnology

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Summary Whole‐cell bioconversion of technical lignins using Pseudomonas putida strains overexpressing amine transaminases (ATAs) has the potential to become an eco‐efficient route to produce phenolic amines. Here, a novel cell growth‐based screening method to evaluate the in vivo activity of recombinant ATAs towards vanillylamine in P. putida KT2440 was developed. It allowed the identification of the native enzyme Pp‐SpuC‐II and ATA from Chromobacterium violaceum (Cv‐ATA) as highly active towards vanillylamine in vivo. Overexpression of Pp‐SpuC‐II and Cv‐ATA in the strain GN442ΔPP_2426, previously engineered for reduced vanillin assimilation, resulted in 94‐ and 92‐fold increased specific transaminase activity, respectively. Whole‐cell bioconversion of vanillin yielded 0.70 ± 0.20 mM and 0.92 ± 0.30 mM vanillylamine, for Pp‐SpuC‐II and Cv‐ATA, respectively. Still, amine production was limited by a substantial re‐assimilation of the product and formation of the by‐products vanillic acid and vanillyl alcohol. Concomitant overexpression of Cv‐ATA and alanine dehydrogenase from Bacillus subtilis increased the production of vanillylamine with ammonium as the only nitrogen source and a reduction in the amount of amine product re‐assimilation. Identification and deletion of additional native genes encoding oxidoreductases acting on vanillin are crucial engineering targets for further improvement.

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Section: Introductionmentioning

confidence: 99%

Metabolic engineering of Pseudomonas putida for production of vanillylamine from lignin‐derived substrates

Manfrão-Netto

Lund

Muratovska

et al. 2021

Microbial Biotechnology

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“…It is significant to synthesize biobased epoxy resins with excellent mechanical characteristics and high T g for the rapidly growing microelectronics and electronics applications. Figure compares the mechanical strength and T g of the cured DGEEA/DDM developed in this work with the previously reported biobased epoxy thermosets. ,,− It can be seen that the cured DGEEA/DDM product exhibits a T g value of 220 °C and a tensile strength of 75.8 MPa, located at the top right corner. The mechanical strength and T g of the cured DGEEA/DDM are higher than those of most of the previously reported biobased epoxy thermosets, manifesting superior thermomechanical properties of the cured DGEEA/DDM owing to the unique structure of EA.…”

Section: Resultsmentioning

confidence: 65%

Phosphorus-Free Ellagic Acid-Derived Epoxy Thermosets with Intrinsic Antiflammability and High Glass Transition Temperature

Nabipour

Qiu

Wang

et al. 2021

ACS Sustainable Chem. Eng.

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Because fossil-based resources are constantly declining, it has become a crucial issue in both academic and industrial fields to develop biobased polymers from renewable resources. Despite excellent comprehensive properties, diglycidyl ether of bisphenol A (DGEBA)type epoxy resin suffers from nonrenewability and flammability. To overcome these shortcomings, a biobased epoxy monomer (DGEEA) derived from ellagic acid (EA) was successfully synthesized and well characterized in this study. The DGEEA monomer was cured by 4,4′diaminodiphenylmethane (DDM) to obtain a biobased epoxy thermoset, with DGEBA cured by DDM as a control sample. The cured DGEEA/DDM product showed a high glass transition temperature of 220 °C, a high tensile strength of 75.8 MPa, and a high Young's modulus of 2.7 GPa, which outperformed the conventional petroleumbased DGEBA/DDM system. Compared with the cured DGEBA/DDM system, the cured DGEEA/DDM product also exhibited an excellent intrinsic antiflammability in terms of the significantly decreased peak heat release rate (77.7 W/g versus 513.9 W/g) and the notably improved limiting oxygen index (40.0% versus 23.0%). Furthermore, the cured DGEEA/DDM product could self-extinct in the UL-94 vertical burning test (corresponding to the V-0 classification), while the cured DGEBA/DDM system burnt out eventually (no classification). The current study provides a prospective path for synthesizing biobased resin with abundant aromatic structures and makes a contribution to the generation of biobased fire-safe epoxy thermosets with exceptional comprehensive properties.

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“…Figure 15 -Synthesis of DGEBPO and DGEBP from vanillin, according to Mogheiseh et al 83 Shibata and Ohkita synthesized a divanillin-based monomer by an aldol condensation between two equivalents of vanillin and cyclopentanone (Figure 15), and used phenolic hardeners in order to generate epoxy-phenol thermosets. 84 More recently, Mogheiseh et al used this divanillin-based monomer, and synthesized a slightly modified epoxy-phenol.…”

Section: Cyclopentanone Bisvanillinmentioning

confidence: 99%

“…84 More recently, Mogheiseh et al used this divanillin-based monomer, and synthesized a slightly modified epoxy-phenol. 83 They formed an oxime by the reaction of the ketone with hydroxylamine. The compound containing two vanillin moieties and the oxime could be glycidylated, adding three glycidylether moieties.…”

Section: Cyclopentanone Bisvanillinmentioning

confidence: 99%

Bio-sourced alternatives to diglycidyl ether of bisphenol A in epoxy–amine thermosets

2024

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Since 1940s, bisphenol A (BPA) has been used in plastic industry reaching production of 10 million tons in 2022. More than 30 % of the produced BPA is used in the production of epoxy resins. Decades of research has now provided enough evidence that (BPA) has endocrine disrupting activity. Hence, it is an urgent matter to replace the use of BPA in production of epoxy resins. In the past years, considerable effort have been put into finding alternatives to the toxic BPA. However, the diglycidylether bisphenol A (DGEBA) does not only exhibits high polymerization reactivity, but the presence of aromatic rings confers interesting thermos-mechanical resistance to epoxy networks therefrom. Hence, this properties are also expected from potential alternatives to BPA. In this review, first the elements leading to toxicity of BPA is explained and then a thorough account of possible bio-sourced aromatic alternatives to BPA are gathered. The reported synthetic routes to each of these alternatives and their toxicity are described. Also, their use in synthesis of epoxy resins and how the new alternatives influence the mechanical properties are discussed. This is a concise summary of the structure-property and structure-toxicity relationship for possible bio-sourced substitutes of BPA in synthesis of epoxy resins.

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Vanillin-derived epoxy monomer for synthesis of bio-based epoxy thermosets: effect of functionality on thermal, mechanical, chemical and structural properties

Cited by 8 publications

References 35 publications

Metabolic engineering of Pseudomonas putida for production of vanillylamine from lignin‐derived substrates

Metabolic engineering of Pseudomonas putida for production of vanillylamine from lignin‐derived substrates

Phosphorus-Free Ellagic Acid-Derived Epoxy Thermosets with Intrinsic Antiflammability and High Glass Transition Temperature

Bio-sourced alternatives to diglycidyl ether of bisphenol A in epoxy–amine thermosets

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