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核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2025

胺功能化磁性间苯二酚甲醛作为一种用于Knoevenagel缩合反应的绿色可重复使用纳米催化剂。

Amine functionalized magnetic resorcinol formaldehyde as a green and reusable nanocatalyst for the Knoevenagel condensation.

作者信息

Dehghani Paria, Elhamifar Dawood, Kargar Shiva

机构信息

Department of Chemistry, Yasouj University, Yasouj, 75918-74831, Iran.

出版信息

Sci Rep. 2025 Jan 22;15(1):2873. doi: 10.1038/s41598-025-85921-3.


DOI:10.1038/s41598-025-85921-3
PMID:39843497
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11754879/
Abstract

Herein, a novel amine-functionalized magnetic resorcinol-formaldehyde with a core-shell structure (FeO@RF/Pr-NH) is prepared through the chemical immobilization of (3-aminopropyl)trimethoxysilane over FeO@RF composite. Characterization through FT-IR, EDX, PXRD, and TGA confirmed successful surface modification while preserving the crystalline structure of FeO. The VSM analysis demonstrated excellent superparamagnetic properties, and SEM and TEM images revealed spherical particles for the designed nanocatalyst. The FeO@RF/Pr-NH nanocomposite was employed as a robust nanocatalyst to promote the Knoevenagel condensation of benzaldehydes with ethyl cyanoacetate and malononitrile, resulting in the formation of substituted olefins. Various aromatic aldehydes were used as substrates in the presence of 0.01 g of FeO@RF/Pr-NH, achieving high to excellent yields (87-97%) within short reaction times (10-50 min) in EtOH at 60 °C. The high performance of FeO@RF/Pr-NH is attributed to the hydrophobic nature of RF shell, which facilitates the accumulation of organic precursors around the catalytic active sites and enhances product yields. The designed magnetic catalyst could retain its high efficiency for at least ten runs. The metal-free, low-cost, and environmentally friendly attributes of the FeO@RF/Pr-NH catalyst make it a promising alternative to traditional metal-based catalysts.

摘要

在此,通过将(3-氨丙基)三甲氧基硅烷化学固定在FeO@RF复合材料上,制备了一种具有核壳结构的新型胺官能化磁性间苯二酚-甲醛(FeO@RF/Pr-NH)。通过傅里叶变换红外光谱(FT-IR)、能谱分析(EDX)、粉末X射线衍射(PXRD)和热重分析(TGA)进行的表征证实了表面改性成功,同时保留了FeO的晶体结构。振动样品磁强计(VSM)分析表明其具有优异的超顺磁性能,扫描电子显微镜(SEM)和透射电子显微镜(TEM)图像显示所设计的纳米催化剂为球形颗粒。FeO@RF/Pr-NH纳米复合材料被用作一种强大的纳米催化剂,以促进苯甲醛与氰基乙酸乙酯和丙二腈的Knoevenagel缩合反应,从而形成取代烯烃。在0.01 g FeO@RF/Pr-NH存在下,使用各种芳香醛作为底物,在60℃的乙醇中,在短反应时间(10 - 50分钟)内可获得高至优异的产率(87 - 97%)。FeO@RF/Pr-NH的高性能归因于RF壳层的疏水性,这有利于有机前体在催化活性位点周围的积累并提高产物产率。所设计的磁性催化剂至少可以保持十次运行的高效率。FeO@RF/Pr-NH催化剂的无金属、低成本和环境友好特性使其成为传统金属基催化剂的有前途的替代品。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/0fe6b6a7cb31/41598_2025_85921_Fig12_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/373d703f8bd8/41598_2025_85921_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/e381f9f303ea/41598_2025_85921_Fig2_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/aedbf0a93789/41598_2025_85921_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/02020a744ab2/41598_2025_85921_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/f07f55a83f79/41598_2025_85921_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/709aa43d4f07/41598_2025_85921_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/a16581ba974c/41598_2025_85921_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/e5126e52b7cb/41598_2025_85921_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/b1085232f804/41598_2025_85921_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/107eea3182b3/41598_2025_85921_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/0fe6b6a7cb31/41598_2025_85921_Fig12_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/373d703f8bd8/41598_2025_85921_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/e381f9f303ea/41598_2025_85921_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/b081b5e9fe1c/41598_2025_85921_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/aedbf0a93789/41598_2025_85921_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/02020a744ab2/41598_2025_85921_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/f07f55a83f79/41598_2025_85921_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/709aa43d4f07/41598_2025_85921_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/a16581ba974c/41598_2025_85921_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/e5126e52b7cb/41598_2025_85921_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/b1085232f804/41598_2025_85921_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/107eea3182b3/41598_2025_85921_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dfa/11754879/0fe6b6a7cb31/41598_2025_85921_Fig12_HTML.jpg

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[3]
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本文引用的文献

[1]
FeO@SiO@CSHVO as a novel recyclable heterogeneous catalyst with core-shell structure for oxidation of sulfides.

Sci Rep. 2024-4-8

[2]
New insight into highly efficient CSA@g-CN for photocatalytic oxidation of benzyl alcohol and thioanisole: NAEDS as a promoter of photoactivity under blue LED irradiation.

Photochem Photobiol. 2024

[3]
Nitrogen-Enriched Biguanidine-Functionalized Cobalt Ferrite Nanoparticles as a Heterogeneous Base Catalyst for Knoevenagel Condensation under Solvent-Free Conditions.

ACS Org Inorg Au. 2023-6-23

[4]
Amine-rich Nickel(II)-Xerogel as a Highly Active Bifunctional Metallo-organo Catalyst for Aqueous Knoevenagel Condensation and Solvent-free CO Cycloaddition.

Inorg Chem. 2023-9-18

[5]
Magnetite-supported montmorillonite (K) (nanocat-Fe-Si-K): an efficient green catalyst for multicomponent synthesis of amidoalkyl naphthol.

RSC Adv. 2023-6-6

[6]
Transition Metal Phosphide Nanoarchitectonics for Versatile Organic Catalysis.

Small. 2023-3

[7]
Magnetically Recoverable Silica-Decorated Ferromagnetic-Nanoceria Nanocatalysts and Their Use with - and -Butyloxycarbonylation Reaction via Solvent-Free Condition.

ACS Omega. 2022-7-7

[8]
Silica sulfuric acid coated on SnFeO MNPs: synthesis, characterization and catalytic applications in the synthesis of polyhydroquinolines.

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[9]
Overview on magnetically recyclable ferrite nanoparticles: synthesis and their applications in coupling and multicomponent reactions.

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[10]
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