Oxidative cleavage of C–C double bond in cinnamic acids with hydrogen peroxide catalysed by vanadium(<scp>v</scp>) oxide

Horvat, Monika; Iskra, Jernej

doi:10.1039/d1gc04416h

Cited by 4 publications

(3 citation statements)

References 51 publications

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“…To confirm that the aldehyde is intermediate, the product distribution at different conversion levels was monitored as shown in Figure 7. It was shown that the dimer of sinapic acid and syringaldehyde are intermediates, and this is in line with reported results [30] . The reaction pathway is shown in Figure S2.…”

Section: Resultssupporting

confidence: 91%

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Synthesis of 2,6‐Dimethoxy‐p‐aminophenol from Hardwood Lignin

Bai

Zhu

et al. 2023

ChemSusChem

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Although the multiple functional groups in biomass offer notable chances for producing high‐value chemicals, most of the current studies focused on the (deep) defunctionalization of biomass and its derivates. Herein, we present a catalytic approach to valorize birch wood lignin with maintaining the methoxy and hydroxy groups in the final product (i.e. 2,6‐dimethoxy‐p‐aminophenol), which has applications in different sectors such as pharmaceuticals. The proved approach involves four steps with a high yield (21.3wt% on the basis of used lignin) to 2,6‐dimethoxy‐p‐aminophenol. The native lignin in birch wood was first converted using alkaline aerobic oxidation in the presence of copper ions toward high‐yield syringaldehyde, which was then selectively oxidized toward 2,6‐dimethoxy‐1,4‐benzoquinone using H2O2 and V2O5. Oximation of 2,6‐dimethoxy‐1,4‐benzoquinone can selectively form 2,6‐dimethoxy‐1,4‐benzoquinone‐4‐oxime, which can be quantitatively hydrogenated toward 2,6‐dimethoxy‐p‐aminophenol. This work highlights the unique potential of biomass and its derivates for the sustainable production of high‐value products with exploring the value of inherent functional groups.

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Section: Resultssupporting

confidence: 91%

“…It was shown that the dimer of sinapic acid and syringaldehyde are intermediates, and this is in line with reported results. [30] The reaction pathway is shown in Figure S2.…”

Section: Wet Oxidation Of Birch Wood Toward Syringaldehydementioning

confidence: 99%

Synthesis of 2,6‐Dimethoxy‐p‐aminophenol from Hardwood Lignin

Bai

Zhu

et al. 2023

ChemSusChem

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“…Photochemical reactions embedded into polymers have been widely utilized to control the chemical and physical properties of functional materials in modern fields such as medicine, energy, computing, information, and communication. − Trans -cinnamic acid as a biobased resource that exists in plant cell walls as an intermediate metabolite in the biosynthetic pathway of lignin is capable of undergoing photoreversible dimerization. − Upon irradiation with ultraviolet (UV) light of wavelength (λ) > 280 nm, it undergoes [2 + 2] photocycloaddition to form a cyclobutane adduct. , The so-obtained cyclobutane dimer is reported to give photosensitivity with photocleavage at λ < 280 nm. − In nature, the ozonosphere blocks the UV light with λ < 290 nm. Therefore, the cyclobutane structure can be employed to control the degradation of epoxy resins to extend the applicability in functional fields while maintaining the stability of resins during handling, storage, and normal use. − …”

Section: Introductionmentioning

confidence: 99%

Biobased Epoxy Resin with Inherently Deep-UV Photodegradability for a Positive Photoresist and Anticounterfeiting

Jin

Dai

Zhao

et al. 2023

ACS Appl. Polym. Mater.

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Biobased epoxy resins have received widespread attention due to their substitution for petroleum-based ones in conventional fields but are rarely reported in functional materials. Herein, a biobased epoxy resin with inherently deep-UV photodegradability was reported. The strategy was based on the [2 + 2] photocycloaddition of trans-cinnamic acid, a renewable resource, to generate a cyclobutane structure in the backbone, which was cleaved upon <280 nm light irradiation. The as-prepared epoxy resin showed high thermal stability and good thermomechanical properties. Meanwhile, owing to the ozonosphere blocking the UV light with a wavelength of <290 nm, the stability of this epoxy resin was guaranteed under a normal environment. When exposed to deep-UV light irradiation, degradation occurred. The degradation mechanism study demonstrated that molecular packing (crystalline/amorphism) was important in determining its degradability. Based on its photoresponsive features, the feasibility of this epoxy resin in the fields of a positive photoresist and anticounterfeiting was well explored. This work provides an attractive strategy for developing biobased epoxy resins to expand their potential application fields.

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