Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal Oxides
Furfural (FF) is a strategic product for the development of highly valued chemicals from biomass. The oxidation product of FF, furoic acid (FA), is an important precursor for the synthesis of green esters, such as methyl furoate. Taking into account issues with the direct furfural oxidation, furfura...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-04-01
|
| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/10/4/430 |
| _version_ | 1797570564658823168 |
|---|---|
| author | Camila P. Ferraz Adriano H. Braga Mohamed Nawfal Ghazzal Michał Zieliński Mariusz Pietrowski Ivaldo Itabaiana Franck Dumeignil Liane M. Rossi Robert Wojcieszak |
| author_facet | Camila P. Ferraz Adriano H. Braga Mohamed Nawfal Ghazzal Michał Zieliński Mariusz Pietrowski Ivaldo Itabaiana Franck Dumeignil Liane M. Rossi Robert Wojcieszak |
| author_sort | Camila P. Ferraz |
| collection | DOAJ |
| description | Furfural (FF) is a strategic product for the development of highly valued chemicals from biomass. The oxidation product of FF, furoic acid (FA), is an important precursor for the synthesis of green esters, such as methyl furoate. Taking into account issues with the direct furfural oxidation, furfural derivatives, such as alkyl furoates, can be easily prepared <i>via</i> oxidative esterification. Here, Au nanoparticles that were immobilized on alkaline-earth metal oxide supports were studied for the oxidative esterification of furfural while using alcohol as both reactant and solvent. The formation of esters is favored by the presence of basic sites on catalyst surface, resulting in high selectivity, preventing the formation of the acetal as a by-product. The Au/MgO sample provided up to 95% methyl furoate (MF) yield, a fast reaction rate, and high performance for furfural:Au molar ratios between 50 and 300. Furthermore, this catalyst was stable during reuse, since both the selectivity and the activity were maintained after four cycles. Oxidative esterification products were achieved in the presence of other alcohols, leading to the formation of esters of up to C<sub>5</sub> (isopentyl furoate) with high selectivity (>99%). Linear and branched esters were formed, but the long-chain linear alcohols resulted in higher yields, such as <i>n</i>-butyl furoate in 94% yield. |
| first_indexed | 2024-03-10T20:27:18Z |
| format | Article |
| id | doaj.art-984dd164e6a84fad95aed4efa6c3bd97 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T20:27:18Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-984dd164e6a84fad95aed4efa6c3bd972023-11-19T21:41:32ZengMDPI AGCatalysts2073-43442020-04-0110443010.3390/catal10040430Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal OxidesCamila P. Ferraz0Adriano H. Braga1Mohamed Nawfal Ghazzal2Michał Zieliński3Mariusz Pietrowski4Ivaldo Itabaiana5Franck Dumeignil6Liane M. Rossi7Robert Wojcieszak8Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, BrazilDepartamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, BrazilInstitut de Chimie Physique, Université Paris-Saclay, UMR 8000 CNRS, 91405 Orsay, FranceFaculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandFaculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandUniv. Lille, CNRS, Centrale Lille, Univ. Artois, UMR 8181—UCCS—Unité de Catalyse et Chimie du Solide, F-59000 Lille, FranceUniv. Lille, CNRS, Centrale Lille, Univ. Artois, UMR 8181—UCCS—Unité de Catalyse et Chimie du Solide, F-59000 Lille, FranceDepartamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508-000, BrazilUniv. Lille, CNRS, Centrale Lille, Univ. Artois, UMR 8181—UCCS—Unité de Catalyse et Chimie du Solide, F-59000 Lille, FranceFurfural (FF) is a strategic product for the development of highly valued chemicals from biomass. The oxidation product of FF, furoic acid (FA), is an important precursor for the synthesis of green esters, such as methyl furoate. Taking into account issues with the direct furfural oxidation, furfural derivatives, such as alkyl furoates, can be easily prepared <i>via</i> oxidative esterification. Here, Au nanoparticles that were immobilized on alkaline-earth metal oxide supports were studied for the oxidative esterification of furfural while using alcohol as both reactant and solvent. The formation of esters is favored by the presence of basic sites on catalyst surface, resulting in high selectivity, preventing the formation of the acetal as a by-product. The Au/MgO sample provided up to 95% methyl furoate (MF) yield, a fast reaction rate, and high performance for furfural:Au molar ratios between 50 and 300. Furthermore, this catalyst was stable during reuse, since both the selectivity and the activity were maintained after four cycles. Oxidative esterification products were achieved in the presence of other alcohols, leading to the formation of esters of up to C<sub>5</sub> (isopentyl furoate) with high selectivity (>99%). Linear and branched esters were formed, but the long-chain linear alcohols resulted in higher yields, such as <i>n</i>-butyl furoate in 94% yield.https://www.mdpi.com/2073-4344/10/4/430gold nanoparticlesesterificationgreen oxidationmethyl furoatebiomass |
| spellingShingle | Camila P. Ferraz Adriano H. Braga Mohamed Nawfal Ghazzal Michał Zieliński Mariusz Pietrowski Ivaldo Itabaiana Franck Dumeignil Liane M. Rossi Robert Wojcieszak Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal Oxides Catalysts gold nanoparticles esterification green oxidation methyl furoate biomass |
| title | Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal Oxides |
| title_full | Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal Oxides |
| title_fullStr | Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal Oxides |
| title_full_unstemmed | Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal Oxides |
| title_short | Efficient Oxidative Esterification of Furfural Using Au Nanoparticles Supported on Group 2 Alkaline Earth Metal Oxides |
| title_sort | efficient oxidative esterification of furfural using au nanoparticles supported on group 2 alkaline earth metal oxides |
| topic | gold nanoparticles esterification green oxidation methyl furoate biomass |
| url | https://www.mdpi.com/2073-4344/10/4/430 |
| work_keys_str_mv | AT camilapferraz efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT adrianohbraga efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT mohamednawfalghazzal efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT michałzielinski efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT mariuszpietrowski efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT ivaldoitabaiana efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT franckdumeignil efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT lianemrossi efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides AT robertwojcieszak efficientoxidativeesterificationoffurfuralusingaunanoparticlessupportedongroup2alkalineearthmetaloxides |