Efficient and scalable synthesis of bis(indolyl)methanes via functionalized asphaltene

• A novel reusable catalytic system comprising asphaltene sulfonic acid decorated with L-proline was successfully synthesized and characterized. • Detailed spectroscopic analysis confirmed the structure and composition of the prepared functionalized asphaltene catalyst. • The catalytic efficacy of Asph-SO3H@pro was investigated for the green synthesis of bis(indolyl)methane derivatives. • The protocol offers several advantages, including waste utilization as a novel catalyst, low catalyst loadings, and the ability to achieve moderate to excellent yields. • The functionalized asphaltene catalyst demonstrated remarkable recyclability, maintaining its activity for six consecutive cycles without significant loss. Asphaltenes are the heaviest and most aromatic fractions of crude oil and bitumen, typically regarded as low-value by-products in the petroleum industry. Due to their complex polyaromatic structure, abundance of heteroatoms, and surface-active functional groups, asphaltenes offer significant potential as low-cost precursors for functional materials and heterogeneous catalysts. Herein, a novel reusable catalytic system comprising asphaltene sulfonic acid (Asph-SO 3 H) decorated with L-proline (Asph-SO 3 H@pro) has been successfully synthesized and characterized. Detailed spectroscopic analysis confirmed the structure and composition of the prepared asphaltene. The catalytic efficacy of Asph-SO 3 H@pro was investigated for synthesizing bis(indolyl)methane derivatives. The protocol offers several advantages, including waste utilization as a novel catalyst, operation under room-temperature conditions, low catalyst loadings, and the ability to achieve moderate to excellent yields. Notably, the catalyst demonstrated remarkable recyclability and maintained its activity for six consecutive cycles without significant loss. This sustainable catalytic system presents a valuable contribution to the field of organic synthesis, offering an efficient, and environmentally friendly approach for the synthesis of bis(indolyl)methane derivatives.

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Publication Details

Journal
Results in Engineering
Published
2026-01-02
DOI
https://doi.org/10.1016/j.rineng.2026.108962
Primary Topic
Synthesis of Indole Derivatives
Type
article
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article

Efficient and scalable synthesis of bis(indolyl)methanes via functionalized asphaltene

Navid Habibnejad, Najmedin Azizi, Mohsen Hajibeygi
Results in Engineering
Synthesis of Indole Derivatives
article

Efficient and scalable synthesis of bis(indolyl)methanes via functionalized asphaltene

Navid Habibnejad, Najmedin Azizi, Mohsen Hajibeygi
article en

Abstract

• A novel reusable catalytic system comprising asphaltene sulfonic acid decorated with L-proline was successfully synthesized and characterized. • Detailed spectroscopic analysis confirmed the structure and composition of the prepared functionalized asphaltene catalyst. • The catalytic efficacy of Asph-SO3H@pro was investigated for the green synthesis of bis(indolyl)methane derivatives. • The protocol offers several advantages, including waste utilization as a novel catalyst, low catalyst loadings, and the ability to achieve moderate to excellent yields. • The functionalized asphaltene catalyst demonstrated remarkable recyclability, maintaining its activity for six consecutive cycles without significant loss. Asphaltenes are the heaviest and most aromatic fractions of crude oil and bitumen, typically regarded as low-value by-products in the petroleum industry. Due to their complex polyaromatic structure, abundance of heteroatoms, and surface-active functional groups, asphaltenes offer significant potential as low-cost precursors for functional materials and heterogeneous catalysts. Herein, a novel reusable catalytic system comprising asphaltene sulfonic acid (Asph-SO 3 H) decorated with L-proline (Asph-SO 3 H@pro) has been successfully synthesized and characterized. Detailed spectroscopic analysis confirmed the structure and composition of the prepared asphaltene. The catalytic efficacy of Asph-SO 3 H@pro was investigated for synthesizing bis(indolyl)methane derivatives. The protocol offers several advantages, including waste utilization as a novel catalyst, operation under room-temperature conditions, low catalyst loadings, and the ability to achieve moderate to excellent yields. Notably, the catalyst demonstrated remarkable recyclability and maintained its activity for six consecutive cycles without significant loss. This sustainable catalytic system presents a valuable contribution to the field of organic synthesis, offering an efficient, and environmentally friendly approach for the synthesis of bis(indolyl)methane derivatives.

Results in EngineeringVol. 29
Kharazmi University (IR), Chemistry and Chemical Engineering Research Center of Iran (IR)
Responsible consumption and production
Openalex Percentile: Top 99%
Synthesis of Indole Derivatives
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