Adipic acid synthesis from bio-derived 2-furoic acid by reduction-carbonylation

Adipic acid (ADA) serves as a crucial monomer for the manufacturing of nylon and polyurethanes. However, current production methods are based on petrochemical feedstocks and pose significant environmental concerns. Consequently, the development of an innovative catalytic system for producing ADA from renewable biomass-derived feedstocks is of significant importance. Herein, we report a novel one-pot, two-step process for the highly efficient synthesis of ADA from the biomass derivative 2-furoic acid via hydrogenative carbonylation. In the first step, 2-furoic acid is selectively reduced to 2-tetrahydrofuroic acid using a Rh catalyst with acetic acid (AcOH) and water (H 2 O) as solvents. Subsequently, within the same catalytic system, the addition of I 2 as a promoter enables the further conversion of 2-tetrahydrofuroic acid to ADA through a highly selective carbonylation reaction under CO and H 2 atmospheres. This one-pot, two-step process achieved an ADA yield of 91.4 % from 2-furoic acid. Mechanistic studies revealed that 5-iodopentanoic acid is the key intermediate in the carbonylation process. In summary, this research introduces an innovative and environmentally friendly approach for synthesizing ADA from biomass-derived 2-furoic acid, offering great potential for industrial application. • Adipic acid can be obtained from 2-tetrahydrofuroic acid by carbonylation with high selectivity. • 5-Iodopentanoic acid was the key intermediate during the carbonylation reaction. • A process was developed to synthesis adipic acid from 2-furoic acid in one-pot two-step strategy.

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Publication Details

Journal
Green Carbon
Published
2025-04-06
DOI
https://doi.org/10.1016/j.greenca.2025.02.008
Citations
4
Primary Topic
Catalysis for Biomass Conversion
Type
article
Field-Weighted Citation Impact
2.70

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article

Adipic acid synthesis from bio-derived 2-furoic acid by reduction-carbonylation

Weiran Yang, Shaofei Shen, Changpo Ma, Xiaoxuan Zhang et al.
4 citations
Green Carbon
Catalysis for Biomass Conversion
2.70
article

Adipic acid synthesis from bio-derived 2-furoic acid by reduction-carbonylation

Weiran Yang, Shaofei Shen, Changpo Ma, Xiaoxuan Zhang, Tiange Zhao, Yunpu Wang, Lingzhao Kong
article en
4 citations

Abstract

Adipic acid (ADA) serves as a crucial monomer for the manufacturing of nylon and polyurethanes. However, current production methods are based on petrochemical feedstocks and pose significant environmental concerns. Consequently, the development of an innovative catalytic system for producing ADA from renewable biomass-derived feedstocks is of significant importance. Herein, we report a novel one-pot, two-step process for the highly efficient synthesis of ADA from the biomass derivative 2-furoic acid via hydrogenative carbonylation. In the first step, 2-furoic acid is selectively reduced to 2-tetrahydrofuroic acid using a Rh catalyst with acetic acid (AcOH) and water (H 2 O) as solvents. Subsequently, within the same catalytic system, the addition of I 2 as a promoter enables the further conversion of 2-tetrahydrofuroic acid to ADA through a highly selective carbonylation reaction under CO and H 2 atmospheres. This one-pot, two-step process achieved an ADA yield of 91.4 % from 2-furoic acid. Mechanistic studies revealed that 5-iodopentanoic acid is the key intermediate in the carbonylation process. In summary, this research introduces an innovative and environmentally friendly approach for synthesizing ADA from biomass-derived 2-furoic acid, offering great potential for industrial application. • Adipic acid can be obtained from 2-tetrahydrofuroic acid by carbonylation with high selectivity. • 5-Iodopentanoic acid was the key intermediate during the carbonylation reaction. • A process was developed to synthesis adipic acid from 2-furoic acid in one-pot two-step strategy.

Green CarbonVol. 3(3)
Nanchang University (CN), Suzhou University of Science and Technology (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 11%
Catalysis for Biomass Conversion
2.70
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