Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101
© 2018 American Chemical Society. Industrial synthesis of succinic acid relies on hydrocarbon oxidation or biomass fermentation routes that suffer from energy-costly separation processes. Here we demonstrate an alternate route to succinic anhydrides via β-lactone carbonylation by heterogeneous bimet...
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| Format: | Article |
| Language: | English |
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American Chemical Society (ACS)
2021
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| Online Access: | https://hdl.handle.net/1721.1/135796 |
| _version_ | 1826191968047202304 |
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| author | Park, Hoyoung D Dincă, Mircea Román-Leshkov, Yuriy |
| author2 | Massachusetts Institute of Technology. Department of Chemical Engineering |
| author_facet | Massachusetts Institute of Technology. Department of Chemical Engineering Park, Hoyoung D Dincă, Mircea Román-Leshkov, Yuriy |
| author_sort | Park, Hoyoung D |
| collection | MIT |
| description | © 2018 American Chemical Society. Industrial synthesis of succinic acid relies on hydrocarbon oxidation or biomass fermentation routes that suffer from energy-costly separation processes. Here we demonstrate an alternate route to succinic anhydrides via β-lactone carbonylation by heterogeneous bimetallic ion-pair catalysis in Co(CO)4--incorporated Cr-MIL-101 (Co(CO)4Cr-MIL-101, Cr-MIL-101 = Cr3O(BDC)3F, H2BDC = 1,4-benzenedicarboxylic acid). Postsynthetically introduced Co(CO)4- facilitates CO insertion to β-lactone substrates activated by the Lewis acidic Cr(III) centers of the metal-organic framework (MOF), leading to catalytic carbonylation with activity and selectivity profiles that compare favorably to those reported for homogeneous ion-pair catalysts. Moreover, the heterogeneous nature of the MOF catalyst enables continuous production of succinic anhydride through a packed bed reactor, with room temperature β-propiolactone carbonylation activity of 1300 molAnhydride·molCo-1 over 6 h on stream. Simple evaporation of the fully converted product stream yields the desired anhydride as isolated solids, highlighting the unique processing advantages conferred by this first example of heterogeneous β-lactone carbonylation pathway. |
| first_indexed | 2024-09-23T09:04:08Z |
| format | Article |
| id | mit-1721.1/135796 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T09:04:08Z |
| publishDate | 2021 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1357962023-02-17T20:24:56Z Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101 Park, Hoyoung D Dincă, Mircea Román-Leshkov, Yuriy Massachusetts Institute of Technology. Department of Chemical Engineering Massachusetts Institute of Technology. Department of Chemistry © 2018 American Chemical Society. Industrial synthesis of succinic acid relies on hydrocarbon oxidation or biomass fermentation routes that suffer from energy-costly separation processes. Here we demonstrate an alternate route to succinic anhydrides via β-lactone carbonylation by heterogeneous bimetallic ion-pair catalysis in Co(CO)4--incorporated Cr-MIL-101 (Co(CO)4Cr-MIL-101, Cr-MIL-101 = Cr3O(BDC)3F, H2BDC = 1,4-benzenedicarboxylic acid). Postsynthetically introduced Co(CO)4- facilitates CO insertion to β-lactone substrates activated by the Lewis acidic Cr(III) centers of the metal-organic framework (MOF), leading to catalytic carbonylation with activity and selectivity profiles that compare favorably to those reported for homogeneous ion-pair catalysts. Moreover, the heterogeneous nature of the MOF catalyst enables continuous production of succinic anhydride through a packed bed reactor, with room temperature β-propiolactone carbonylation activity of 1300 molAnhydride·molCo-1 over 6 h on stream. Simple evaporation of the fully converted product stream yields the desired anhydride as isolated solids, highlighting the unique processing advantages conferred by this first example of heterogeneous β-lactone carbonylation pathway. 2021-10-27T20:29:20Z 2021-10-27T20:29:20Z 2018 2019-09-10T18:32:05Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/135796 en 10.1021/JACS.8B05948 Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) MIT web domain |
| spellingShingle | Park, Hoyoung D Dincă, Mircea Román-Leshkov, Yuriy Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101 |
| title | Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101 |
| title_full | Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101 |
| title_fullStr | Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101 |
| title_full_unstemmed | Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101 |
| title_short | Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO) 4 ⊂Cr-MIL-101 |
| title_sort | continuous flow production of succinic anhydrides via catalytic β lactone carbonylation by co co 4 ⊂cr mil 101 |
| url | https://hdl.handle.net/1721.1/135796 |
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