Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cation
The coupling reaction of carbon dioxide (CO2) and epoxides is one of the most efficient pathways to achieve the carbon balance. However, to accomplish it under the mild conditions, especially under the atmospheric pressure, is still a perplexing problem. Three novel ionic liquids (ILs), [DMAPBrPC][T...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2023-09-01
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| Series: | Green Chemical Engineering |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666952822000504 |
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| author | Zhengkun Zhang Jinya Li Guanyao Yu Chao Zeng Menglong Wang Susu Huang Li Wang Jinglai Zhang |
| author_facet | Zhengkun Zhang Jinya Li Guanyao Yu Chao Zeng Menglong Wang Susu Huang Li Wang Jinglai Zhang |
| author_sort | Zhengkun Zhang |
| collection | DOAJ |
| description | The coupling reaction of carbon dioxide (CO2) and epoxides is one of the most efficient pathways to achieve the carbon balance. However, to accomplish it under the mild conditions, especially under the atmospheric pressure, is still a perplexing problem. Three novel ionic liquids (ILs), [DMAPBrPC][TMGH], [DMAPBrPC][DBUH], and [DMAPBrPC][BTMA], are designed and synthesized. All of them display the excellent catalytic activity for the title reaction achieving the yield over 96.6% under the atmospheric CO2 pressure at 60 °C. Interestingly, [DMAPBrPC][BTMA] with the inert hydrogen atom in cation exhibits the superior catalytic activity as compared to other two ILs with the protic hydrogen atom in cation along with the same anion. The active hydrogen atom in [DMAPBrPC][TMGH] and [DMAPBrPC][DBUH] would impede the –COO− group to absorb CO2, which is an unfavorable item for the reaction. Moreover, the strong hydrogen bond in [DMAPBrPC][TMGH] and [DMAPBrPC][DBUH] would lessen the nucleophilic ability of Br− anion resulting in the inferior catalytic performance, which is further confirmed by the density functional theory (DFT) calculations. The cation without the active hydrogen atom could also be employed to design the ILs with the excellent catalytic feature when it is combined with the suitable anion. |
| first_indexed | 2024-03-12T01:56:27Z |
| format | Article |
| id | doaj.art-b5d0de2155cf4d9ebb0c0d810b7a5297 |
| institution | Directory Open Access Journal |
| issn | 2666-9528 |
| language | English |
| last_indexed | 2024-03-12T01:56:27Z |
| publishDate | 2023-09-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Chemical Engineering |
| spelling | doaj.art-b5d0de2155cf4d9ebb0c0d810b7a52972023-09-08T04:34:06ZengKeAi Communications Co. Ltd.Green Chemical Engineering2666-95282023-09-0143285293Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cationZhengkun Zhang0Jinya Li1Guanyao Yu2Chao Zeng3Menglong Wang4Susu Huang5Li Wang6Jinglai Zhang7Henan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, ChinaHenan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, ChinaHenan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, ChinaHenan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, ChinaHenan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, ChinaHenan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, ChinaHenan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, China; Corresponding author.Henan Province Engineering Research Center of Green Anticorrosion Technology for Magnesium Alloys, Henan University, Kaifeng, 475004, China; Henan Engineering Research Center of Corrosion and Protection for Magnesium Alloys, Henan University, Kaifeng, 475004, China; College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, China; Corresponding author.The coupling reaction of carbon dioxide (CO2) and epoxides is one of the most efficient pathways to achieve the carbon balance. However, to accomplish it under the mild conditions, especially under the atmospheric pressure, is still a perplexing problem. Three novel ionic liquids (ILs), [DMAPBrPC][TMGH], [DMAPBrPC][DBUH], and [DMAPBrPC][BTMA], are designed and synthesized. All of them display the excellent catalytic activity for the title reaction achieving the yield over 96.6% under the atmospheric CO2 pressure at 60 °C. Interestingly, [DMAPBrPC][BTMA] with the inert hydrogen atom in cation exhibits the superior catalytic activity as compared to other two ILs with the protic hydrogen atom in cation along with the same anion. The active hydrogen atom in [DMAPBrPC][TMGH] and [DMAPBrPC][DBUH] would impede the –COO− group to absorb CO2, which is an unfavorable item for the reaction. Moreover, the strong hydrogen bond in [DMAPBrPC][TMGH] and [DMAPBrPC][DBUH] would lessen the nucleophilic ability of Br− anion resulting in the inferior catalytic performance, which is further confirmed by the density functional theory (DFT) calculations. The cation without the active hydrogen atom could also be employed to design the ILs with the excellent catalytic feature when it is combined with the suitable anion.http://www.sciencedirect.com/science/article/pii/S2666952822000504Carbon dioxideDMAP-based ionic liquidsInert hydrogen atomDFT calculationsAtmospheric pressure |
| spellingShingle | Zhengkun Zhang Jinya Li Guanyao Yu Chao Zeng Menglong Wang Susu Huang Li Wang Jinglai Zhang Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cation Green Chemical Engineering Carbon dioxide DMAP-based ionic liquids Inert hydrogen atom DFT calculations Atmospheric pressure |
| title | Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cation |
| title_full | Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cation |
| title_fullStr | Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cation |
| title_full_unstemmed | Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cation |
| title_short | Efficient synthesis of cyclic carbonates under atmospheric CO2 by DMAP-based ionic liquids: the difference of inert hydrogen atom and active hydrogen atom in cation |
| title_sort | efficient synthesis of cyclic carbonates under atmospheric co2 by dmap based ionic liquids the difference of inert hydrogen atom and active hydrogen atom in cation |
| topic | Carbon dioxide DMAP-based ionic liquids Inert hydrogen atom DFT calculations Atmospheric pressure |
| url | http://www.sciencedirect.com/science/article/pii/S2666952822000504 |
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