One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate
Conversion of unsaturated fatty acids, FAMEs or triglycerides into the corresponding cyclic organic carbonates involves two reaction steps—double-bond epoxidation and CO<sub>2</sub> insertion into the epoxide—that are generally conducted separately. We describe an assisted-tandem catalyt...
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| Format: | Article |
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MDPI AG
2021-12-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/11/12/1477 |
| _version_ | 1797506020214308864 |
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| author | Roberto Calmanti Nicola Sargentoni Maurizio Selva Alvise Perosa |
| author_facet | Roberto Calmanti Nicola Sargentoni Maurizio Selva Alvise Perosa |
| author_sort | Roberto Calmanti |
| collection | DOAJ |
| description | Conversion of unsaturated fatty acids, FAMEs or triglycerides into the corresponding cyclic organic carbonates involves two reaction steps—double-bond epoxidation and CO<sub>2</sub> insertion into the epoxide—that are generally conducted separately. We describe an assisted-tandem catalytic protocol able to carry out carbonation of unsaturated methyl oleate in one-pot without isolating the epoxide intermediate. Methyl oleate carbonate was obtained in 99% yield and high retention of <i>cis</i>-configuration starting from methyl oleate using hydrogen peroxide and CO<sub>2</sub> as green reagents, in a biphasic system and in the presence of an ammonium tungstate ionic liquid catalyst with KBr as co-catalyst. |
| first_indexed | 2024-03-10T04:26:39Z |
| format | Article |
| id | doaj.art-4883abac8d5c45429da7328018accb74 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T04:26:39Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-4883abac8d5c45429da7328018accb742023-11-23T07:34:12ZengMDPI AGCatalysts2073-43442021-12-011112147710.3390/catal11121477One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic CarbonateRoberto Calmanti0Nicola Sargentoni1Maurizio Selva2Alvise Perosa3Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30172 Venezia Mestre, ItalyDipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30172 Venezia Mestre, ItalyDipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30172 Venezia Mestre, ItalyDipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30172 Venezia Mestre, ItalyConversion of unsaturated fatty acids, FAMEs or triglycerides into the corresponding cyclic organic carbonates involves two reaction steps—double-bond epoxidation and CO<sub>2</sub> insertion into the epoxide—that are generally conducted separately. We describe an assisted-tandem catalytic protocol able to carry out carbonation of unsaturated methyl oleate in one-pot without isolating the epoxide intermediate. Methyl oleate carbonate was obtained in 99% yield and high retention of <i>cis</i>-configuration starting from methyl oleate using hydrogen peroxide and CO<sub>2</sub> as green reagents, in a biphasic system and in the presence of an ammonium tungstate ionic liquid catalyst with KBr as co-catalyst.https://www.mdpi.com/2073-4344/11/12/1477direct oxidative carboxylationtandem catalysiscyclic organic carbonatestungstate ionic liquids |
| spellingShingle | Roberto Calmanti Nicola Sargentoni Maurizio Selva Alvise Perosa One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate Catalysts direct oxidative carboxylation tandem catalysis cyclic organic carbonates tungstate ionic liquids |
| title | One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate |
| title_full | One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate |
| title_fullStr | One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate |
| title_full_unstemmed | One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate |
| title_short | One-Pot Tandem Catalytic Epoxidation—CO<sub>2</sub> Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate |
| title_sort | one pot tandem catalytic epoxidation co sub 2 sub insertion of monounsaturated methyl oleate to the corresponding cyclic organic carbonate |
| topic | direct oxidative carboxylation tandem catalysis cyclic organic carbonates tungstate ionic liquids |
| url | https://www.mdpi.com/2073-4344/11/12/1477 |
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