Oxidative cleavage of C–C double bond in cinnamic acids with hydrogen peroxide catalysed by vanadium(V) oxide

Horvat, Monika (avtor), Iskra, Jernej (avtor)

We have developed a cheap, green, mild and environmentally friendly method for the selective cleavage of carbon–carbon double bonds with a 30% aqueous solution of hydrogen peroxide as the oxidant and vanadium(V) oxide as the catalyst. The selectivity of the oxidative cleavage of cinnamic acid derivatives 1 depends on the substituents and the solvent used (DME – MeOCH$_2$CH$_2$OMe, TFE – 2,2,2-trifluoroethanol or MeCN). In DME, p-hydroxy derivatives were selectively converted to benzaldehyde derivatives 2, in TFE, oxidative cleavage led to the formation of benzoquinone derivatives 4, while in MeCN, cinnamic acid derivatives were selectively converted to benzoic acid derivatives 3. Ferulic acid 1a was quantitatively and selectively converted to vanillin 2a in a 91% isolated yield on a gram scale. Dimeric difurandione 1a’ was isolated as an intermediate, which was confirmed by in situ ATR-IR spectroscopy, while the formation of diols or epoxides was not observed. The analogous styrene derivative, 4-vinylguaiacol 1e was also selectively converted to either vanillin 2a or 2-methoxyquinone 4a in a high yield. The green metric for the conversion of ferulic acid to vanillin by different methods was calculated and compared to our method, and showed that our method has better environmental parameters.

• Jezik: Angleški jezik
• Ključne besede: lignocellulosic biomass, oxidation, lignin, ferulic acid, vanillin, hydrogen peroxide
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2022
• Št. strani: Str. 2073-2081
• Številčenje: Vol. 24, iss. 5
• PID: 20.500.12556/RUL-141871
• UDK: 547.5:542.943'7
• ISSN pri članku: 1463-9262
• DOI: 10.1039/D1GC04416H
• COBISS.SI-ID: 97890051
• Datum objave v RUL: 10.10.2022

Gradivo je del revije

• Naslov: Green chemistry
• Skrajšan naslov: Green chem.
• Založnik: Royal Society of Chemistry
• ISSN: 1463-9262
• COBISS.SI-ID: 24129285

Licence

• Licenca: CC BY-NC 3.0, Creative Commons Priznanje avtorstva-Nekomercialno 3.0 Nedoločena
• Povezava: https://creativecommons.org/licenses/by-nc/3.0/deed.sl
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Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: lignocelulozna biomasa, oksidacija, lignin, ferulna kislina, vanilin, vodikov peroksid

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0134
• Naslov: Kemija za trajnostni razvoj

• Financer: EC - European Commission
• Program financ.: European Regional Development Fund, Urban Innovative Actions
• Akronim: APPLAUSE