Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence
Vegetable oils are bio−based and sustainable starting materials that can be used to develop chemicals for industrial processes. In this study, the functionalization of three vegetable oils (grape, hemp, and linseed) with maleic anhydride was carried out either by conventional heating or microwave ac...
| Main Authors: | , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-11-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/23/8142 |
| _version_ | 1827642907142651904 |
|---|---|
| author | Francesco Lanero Bianca Maria Bresolin Anna Scettri Marco Nogarole Elisabetta Schievano Stefano Mammi Giacomo Saielli Alessia Famengo Alessandra Semenzato Giovanni Tafuro Paolo Sgarbossa Roberta Bertani |
| author_facet | Francesco Lanero Bianca Maria Bresolin Anna Scettri Marco Nogarole Elisabetta Schievano Stefano Mammi Giacomo Saielli Alessia Famengo Alessandra Semenzato Giovanni Tafuro Paolo Sgarbossa Roberta Bertani |
| author_sort | Francesco Lanero |
| collection | DOAJ |
| description | Vegetable oils are bio−based and sustainable starting materials that can be used to develop chemicals for industrial processes. In this study, the functionalization of three vegetable oils (grape, hemp, and linseed) with maleic anhydride was carried out either by conventional heating or microwave activation to obtain products that, after further reactions, can enhance the water dispersion of oils for industrial applications. To identify the most abundant derivatives formed, trans-3-octene, methyl oleate, and ethyl linoleate were reacted as reference systems. A detailed NMR study, supported by computational evidence, allowed for the identification of the species formed in the reaction of trans-3-octene with maleic anhydride. The signals in the <sup>1</sup>H NMR spectra of the alkenyl succinic anhydride (ASA) moieties bound to the organic chains were clearly identified. The reactions achieved by conventional heating were carried out for 5 h at 200 °C, resulting in similar or lower amounts of ASA units/g of oil with respect to the reactions performed by microwave activation, which, however, induced a higher viscosity of the samples. |
| first_indexed | 2024-03-09T17:40:31Z |
| format | Article |
| id | doaj.art-3af618b885c64adea66591819331fd3d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T17:40:31Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3af618b885c64adea66591819331fd3d2023-11-24T11:37:18ZengMDPI AGMolecules1420-30492022-11-012723814210.3390/molecules27238142Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR EvidenceFrancesco Lanero0Bianca Maria Bresolin1Anna Scettri2Marco Nogarole3Elisabetta Schievano4Stefano Mammi5Giacomo Saielli6Alessia Famengo7Alessandra Semenzato8Giovanni Tafuro9Paolo Sgarbossa10Roberta Bertani11Dipartimento di Ingegneria Industriale, Università di Padova, Via Marzolo 9, 35131 Padova, ItalyDipartimento di Ingegneria Industriale, Università di Padova, Via Marzolo 9, 35131 Padova, ItalyDipartimento di Ingegneria Industriale, Università di Padova, Via Marzolo 9, 35131 Padova, ItalyStazione Sperimentale per L’industria Delle Pelli e Delle Materie Concianti s.r.l., Organismo di Ricerca Nazionale delle CCIAA di Napoli, Pisa e Vicenza, Via Achille Papa 28, 36071 Arzignano, ItalyDipartimento di Scienze Chimiche, Università di Padova, Via Marzolo 1, 35131 Padova, ItalyDipartimento di Scienze Chimiche, Università di Padova, Via Marzolo 1, 35131 Padova, ItalyDipartimento di Scienze Chimiche, Università di Padova, Via Marzolo 1, 35131 Padova, ItalyCNR—Institute of Condensed Matter Chemistry and Technologies for Energy, C.so Stati Uniti 4, 35127 Padova, ItalyDepartment of Pharmaceutical and Pharmacological Sciences, University of Padova, Via Marzolo 5, 35131 Padova, ItalyUnired Srl, Via Niccolò Tommaseo 69, 35131 Padova, ItalyDipartimento di Ingegneria Industriale, Università di Padova, Via Marzolo 9, 35131 Padova, ItalyDipartimento di Ingegneria Industriale, Università di Padova, Via Marzolo 9, 35131 Padova, ItalyVegetable oils are bio−based and sustainable starting materials that can be used to develop chemicals for industrial processes. In this study, the functionalization of three vegetable oils (grape, hemp, and linseed) with maleic anhydride was carried out either by conventional heating or microwave activation to obtain products that, after further reactions, can enhance the water dispersion of oils for industrial applications. To identify the most abundant derivatives formed, trans-3-octene, methyl oleate, and ethyl linoleate were reacted as reference systems. A detailed NMR study, supported by computational evidence, allowed for the identification of the species formed in the reaction of trans-3-octene with maleic anhydride. The signals in the <sup>1</sup>H NMR spectra of the alkenyl succinic anhydride (ASA) moieties bound to the organic chains were clearly identified. The reactions achieved by conventional heating were carried out for 5 h at 200 °C, resulting in similar or lower amounts of ASA units/g of oil with respect to the reactions performed by microwave activation, which, however, induced a higher viscosity of the samples.https://www.mdpi.com/1420-3049/27/23/8142vegetable oilmaleic anhydrideAlder reactionene reaction2D COSY, HSQC, HMBC and 1D CSSF-TOCSY NMR experiments |
| spellingShingle | Francesco Lanero Bianca Maria Bresolin Anna Scettri Marco Nogarole Elisabetta Schievano Stefano Mammi Giacomo Saielli Alessia Famengo Alessandra Semenzato Giovanni Tafuro Paolo Sgarbossa Roberta Bertani Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence Molecules vegetable oil maleic anhydride Alder reaction ene reaction 2D COSY, HSQC, HMBC and 1D CSSF-TOCSY NMR experiments |
| title | Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence |
| title_full | Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence |
| title_fullStr | Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence |
| title_full_unstemmed | Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence |
| title_short | Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence |
| title_sort | activation of vegetable oils by reaction with maleic anhydride as a renewable source in chemical processes new experimental and computational nmr evidence |
| topic | vegetable oil maleic anhydride Alder reaction ene reaction 2D COSY, HSQC, HMBC and 1D CSSF-TOCSY NMR experiments |
| url | https://www.mdpi.com/1420-3049/27/23/8142 |
| work_keys_str_mv | AT francescolanero activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT biancamariabresolin activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT annascettri activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT marconogarole activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT elisabettaschievano activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT stefanomammi activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT giacomosaielli activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT alessiafamengo activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT alessandrasemenzato activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT giovannitafuro activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT paolosgarbossa activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence AT robertabertani activationofvegetableoilsbyreactionwithmaleicanhydrideasarenewablesourceinchemicalprocessesnewexperimentalandcomputationalnmrevidence |