Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability

Abstract This study investigates the repurposing of asphaltene, a petroleum waste product, as a catalyst for organic reactions. Sulfonated asphaltene was synthesized and evaluated for its efficacy in catalyzing the Mannich reaction, displaying notable diastereoselectivity and operating effectively u...

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Main Authors: Navid Habibnejad, Najmedin Azizi, Mohsen Hajibeygi
Format: Article
Language:English
Published: Nature Portfolio 2024-12-01
Series:Scientific Reports
Subjects:
Online Access:https://doi.org/10.1038/s41598-024-80297-2
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author Navid Habibnejad
Najmedin Azizi
Mohsen Hajibeygi
author_facet Navid Habibnejad
Najmedin Azizi
Mohsen Hajibeygi
author_sort Navid Habibnejad
collection DOAJ
description Abstract This study investigates the repurposing of asphaltene, a petroleum waste product, as a catalyst for organic reactions. Sulfonated asphaltene was synthesized and evaluated for its efficacy in catalyzing the Mannich reaction, displaying notable diastereoselectivity and operating effectively under mild conditions. Characterization of the catalyst’s chemical composition, structure, and thermal stability was conducted using FT-IR, TGA, XRD, CHN, BET-BJH, SEM, and EDS analyses. Employing the sulfonated asphaltene catalyst in a one-pot multi-component reaction to generate β-amino carbonyl derivatives in ethanol resulted in high product yields after 4–7 h. Notably, the catalyst exhibited recyclability, demonstrating reusability for at least 10 reaction cycles.
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spelling doaj.art-037128dd97c44b59bedeb812e780cb002024-12-29T12:17:29ZengNature PortfolioScientific Reports2045-23222024-12-0114111710.1038/s41598-024-80297-2Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclabilityNavid Habibnejad0Najmedin Azizi1Mohsen Hajibeygi2Chemistry and Chemical Engineering Research Center of IranChemistry and Chemical Engineering Research Center of IranDepartment of Organic and Polymer Chemistry, Faculty of Chemistry, Kharazmi UniversityAbstract This study investigates the repurposing of asphaltene, a petroleum waste product, as a catalyst for organic reactions. Sulfonated asphaltene was synthesized and evaluated for its efficacy in catalyzing the Mannich reaction, displaying notable diastereoselectivity and operating effectively under mild conditions. Characterization of the catalyst’s chemical composition, structure, and thermal stability was conducted using FT-IR, TGA, XRD, CHN, BET-BJH, SEM, and EDS analyses. Employing the sulfonated asphaltene catalyst in a one-pot multi-component reaction to generate β-amino carbonyl derivatives in ethanol resulted in high product yields after 4–7 h. Notably, the catalyst exhibited recyclability, demonstrating reusability for at least 10 reaction cycles.https://doi.org/10.1038/s41598-024-80297-2Sulfonated asphalteneMannich reactionGreen chemistryPetroleum waste
spellingShingle Navid Habibnejad
Najmedin Azizi
Mohsen Hajibeygi
Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability
Scientific Reports
Sulfonated asphaltene
Mannich reaction
Green chemistry
Petroleum waste
title Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability
title_full Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability
title_fullStr Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability
title_full_unstemmed Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability
title_short Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability
title_sort sulfonated asphaltene as a highly efficient catalyst for the mannich reaction with excellent diastereoselectivity and recyclability
topic Sulfonated asphaltene
Mannich reaction
Green chemistry
Petroleum waste
url https://doi.org/10.1038/s41598-024-80297-2
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AT najmedinazizi sulfonatedasphalteneasahighlyefficientcatalystforthemannichreactionwithexcellentdiastereoselectivityandrecyclability
AT mohsenhajibeygi sulfonatedasphalteneasahighlyefficientcatalystforthemannichreactionwithexcellentdiastereoselectivityandrecyclability