Heterogeneous/Homogeneous Catalysis in Organic Synthesis – Recent Advances

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (10 June 2022) | Viewed by 23112

Special Issue Editors


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Guest Editor
Silesian University of Technology, Faculty of Chemistry, Department of Chemical Organic Technology and Petrochemistry, 44-100 Gliwice, Poland
Interests: development of heterogeneous catalysis for fine chemicals synthesis; organocatalysis; phase transfer catalysis; reactions involving CO2; green chemistry

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Guest Editor
Silesian University of Technology, Faculty of Chemistry, Department of Chemical Organic Technology and Petrochemistry, 44-100 Gliwice, Poland
Interests: heterogeneous and homogenous catalysis; designing of new methods of organic compounds synthesis; synthesis, characterization and application of ionic liquids; green chemistry

Special Issue Information

Dear Colleagues,

Catalysis is a fascinating phenomenon not only in natural processes but also in chemical ones. About 90% of the chemical industry technologies involve catalysts. The importance of catalysis also highlights the fact that one of the principles of green chemistry is devoted exclusively to this issue. Catalysis is a powerful tool in designing of sustainable, energy- and material-efficient and clean technologies

Important problems facing catalyst designers include understanding the factors affecting the activity of homogenous and heterogeneous catalysts, as well as developing catalysts with readily available active centers for reactants and stable under the process conditions.

Currently, the key challenge for the organic synthesis is the development of new catalysts that characterize both high activity and selectivity, and would ensure their easy separation from the reaction mixture. The removal of the catalyst after reaction is usually cost-intensive and energy-consuming. Therefore, two-way actions are being taken:

  1. improvement of existing separation techniques and introduction of new, more energy-saving techniques
  2. the use of heterogeneous catalysts. Such catalysts create the possibility of their effective recycling. Moreover, they can be used in flow reactors.

This Special Issue aims to collect both original research articles and reviews focusing, though not exclusively, on:

  • The application of heterogeneous and homogenous catalysis in organic synthesis;
  • Synthesis and characterization of new catalysts;
  • Designing of new methods of catalytic synthesis of organic compounds, meeting the requirements of sustainable development and principles of green chemistry.
  • Designing of immobilized catalyst on solid carriers such as polymers, carbon nanomaterials, silica, hybrid supports and others;

Dr. Agnieszka Siewniak
Prof. Dr. Anna Chrobok
Guest Editors

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Keywords

  • heterogeneous catalysis
  • heterogeneous catalysts
  • homogenous catalysis
  • homogenous catalyst
  • immobilized catalysts
  • supported catalysts
  • catalytic processes
  • design of catalysts
  • organic synthesis
  • fine chemicals synthesis
  • green chemistry

 

Published Papers (6 papers)

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Research

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14 pages, 4028 KiB  
Article
Catalytic Oxidation of Phosphine by Aqueous Copper–Ammonia Complexes
by Akbope K. Borangazieva, Yerzhan A. Boleubayev, Zhuldyz U. Ibraimova, Sholpan S. Itkulova and Gulshara S. Polimbetova
Catalysts 2023, 13(2), 271; https://doi.org/10.3390/catal13020271 - 25 Jan 2023
Viewed by 1427
Abstract
The furnace gas resulting from the electrothermal production of yellow phosphorus contains up to 95% CO, 2% O2, 2% H2, and 0.3–4.0% impurities, including phosphine (PH3), yellow phosphorus (P4), and hydrogen sulphide (H2S), [...] Read more.
The furnace gas resulting from the electrothermal production of yellow phosphorus contains up to 95% CO, 2% O2, 2% H2, and 0.3–4.0% impurities, including phosphine (PH3), yellow phosphorus (P4), and hydrogen sulphide (H2S), which are characterized by flammability, explosion hazardousness, corrosiveness, and high toxicity. The presence of toxic impurities does not allow the use of waste gases from phosphorus production, which are mainly composed of valuable carbon monoxide, as chemical raw materials and/or process fuel. The authors propose a method for the purification of furnace gas from the main toxic component, phosphine, by its oxidisation using aqueous copper–ammonia complexes as a catalyst. This approach allows the cleaning process to be conducted under mild conditions. The degree of purification of the model furnace gas from P components is 90–99%, depending on the process conditions. Full article
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13 pages, 3425 KiB  
Article
Effect of Binding Modules Fused to Cutinase on the Enzymatic Synthesis of Polyesters
by Valerio Ferrario, Anamaria Todea, Lisa Wolansky, Nicola Piovesan, Alice Guarneri, Doris Ribitsch, Georg M. Guebitz, Lucia Gardossi and Alessandro Pellis
Catalysts 2022, 12(3), 303; https://doi.org/10.3390/catal12030303 - 07 Mar 2022
Cited by 3 | Viewed by 2103
Abstract
In relation to the development of environmentally-friendly processing technologies for the continuously growing market of plastics, enzymes play an important role as green and sustainable biocatalysts. The present study reports the use of heterogeneous immobilized biocatalysts in solvent-free systems for the synthesis of [...] Read more.
In relation to the development of environmentally-friendly processing technologies for the continuously growing market of plastics, enzymes play an important role as green and sustainable biocatalysts. The present study reports the use of heterogeneous immobilized biocatalysts in solvent-free systems for the synthesis of aliphatic oligoesters with Mws and monomer conversions up to 1500 Da and 74%, respectively. To improve the accessibility of hydrophilic and hydrophobic substrates to the surface of the biocatalyst and improve the reaction kinetic and the chain elongation, two different binding modules were fused on the surface of cutinase 1 from Thermobifida cellulosilytica. The fusion enzymes were successfully immobilized (>99% of bound protein) via covalent bonding onto epoxy-activated beads. To the best of our knowledge, this is the first example where fused enzymes are used to catalyze transesterification reactions for polymer synthesis purposes. Full article
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16 pages, 1936 KiB  
Article
Chiral Quaternary Ammoniums Derived from Dehydroabietylamine: Synthesis and Application to Alkynylation of Isatin Derivatives Catalyzed by Silver
by Guanyu Jiang, Xinduo Sun, Fanrui Zhou, Kun Liang and Qian Chen
Catalysts 2021, 11(12), 1479; https://doi.org/10.3390/catal11121479 - 03 Dec 2021
Cited by 3 | Viewed by 2488
Abstract
Abietic acid and its derivatives have broadly been used in fine chemicals and are renewable resources. Its inherent chiral rigid tricyclic phenanthrene skeleton is unique. Its utilities in asymmetric catalysis remain to be explored. A series new amide-type chiral quaternary ammoniums bearing dehydroabietylamine [...] Read more.
Abietic acid and its derivatives have broadly been used in fine chemicals and are renewable resources. Its inherent chiral rigid tricyclic phenanthrene skeleton is unique. Its utilities in asymmetric catalysis remain to be explored. A series new amide-type chiral quaternary ammoniums bearing dehydroabietylamine were designed, and prepared by two convenient steps. Acylation of dehydroabietylamine with bromoacetyl chloride afforded amide holding bromoacetyl group in higher yields using triethyl amine as base. Subsequent quaternization reaction gave the desired amide-type chiral quaternary ammoniums. The new chiral quaternary ammoniums can be used as phase-transfer catalyst (PTC) for the transition metal-catalysed alkynylation of isatin derivatives. Full article
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17 pages, 8361 KiB  
Article
Poly(imidazolium) Carbosilane Dendrimers: Synthesis, Catalytic Activity in Redox Esterification of α,β-Unsaturated Aldehydes and Recycling via Organic Solvent Nanofiltration
by Alena Krupková, Klára Kubátová, Lucie Červenková Šťastná, Petra Cuřínová, Monika Müllerová, Jindřich Karban, Jan Čermák and Tomáš Strašák
Catalysts 2021, 11(11), 1317; https://doi.org/10.3390/catal11111317 - 29 Oct 2021
Cited by 4 | Viewed by 1619
Abstract
Three series of poly(ionic) carbosilane dendrimers peripherally functionalized with imidazolium groups substituted on N-3 with methyl, isopropyl and 2,6-diisopropylphenyl (Dipp) were prepared up to the 3rd generation together with model monovalent imidazolium iodides and used as N-heterocyclic carbene (NHC) precursors. Catalytic activity of [...] Read more.
Three series of poly(ionic) carbosilane dendrimers peripherally functionalized with imidazolium groups substituted on N-3 with methyl, isopropyl and 2,6-diisopropylphenyl (Dipp) were prepared up to the 3rd generation together with model monovalent imidazolium iodides and used as N-heterocyclic carbene (NHC) precursors. Catalytic activity of model and dendritic NHCs generated in situ by deprotonation with DBU was tested in redox esterification of α,β-unsaturated aldehydes and the influence of substitution, dendrimer generation, temperature and substrate structure on the reaction outcome was evaluated. Dipp substituted NHCs showed high activity and selectivity in the reaction with primary alcohols. Effectiveness of organic solvent nanofiltration for the recycling of dendritic NHCs was demonstrated on the 1st generation Dipp substituted catalyst in model redox esterification of cinnamaldehyde with benzyl alcohol. A marked increase in both activity and selectivity in the first four reaction runs was observed and this improved performance was preserved in the following catalytic cycles. Full article
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17 pages, 4177 KiB  
Article
Structural Requirements for Chemoselective Ammonolysis of Ethylene Glycol to Ethanolamine over Supported Cobalt Catalysts
by Xianchi Lei, Guoding Gu, Yafei Hu, Haoshang Wang, Zhaoxia Zhang and Shuai Wang
Catalysts 2021, 11(6), 736; https://doi.org/10.3390/catal11060736 - 15 Jun 2021
Cited by 4 | Viewed by 5723
Abstract
Ethylene glycol is regarded as a promising C2 platform molecule due to the fast development of its production from sustainable biomass. This study inquired the structural requirements of Co-based catalysts for the liquid-phase ammonolysis of ethylene glycol to value-added ethanolamine. We showed [...] Read more.
Ethylene glycol is regarded as a promising C2 platform molecule due to the fast development of its production from sustainable biomass. This study inquired the structural requirements of Co-based catalysts for the liquid-phase ammonolysis of ethylene glycol to value-added ethanolamine. We showed that the rate and selectivity of ethylene glycol ammonolysis on γ-Al2O3-supported Co catalysts were strongly affected by the metal particle size within the range of 2–10 nm, among which Co nanoparticles of ~4 nm exhibited both the highest ethanolamine selectivity and the highest ammonolysis rate based on the total Co content. Doping of a moderate amount of Ag further promoted the catalytic activity without affecting the selectivity. Combined kinetic and infrared spectroscopic assessments unveiled that the addition of Ag significantly destabilized the adsorbed NH3 on the Co surface, which would otherwise be strongly bound to the active sites and inhibit the rate-determining dehydrogenation step of ethylene glycol. Full article
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Review

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29 pages, 4836 KiB  
Review
Recent Advances in Homogeneous/Heterogeneous Catalytic Hydrogenation and Dehydrogenation for Potential Liquid Organic Hydrogen Carrier (LOHC) Systems
by Jun-Young Cho, Hahyeon Kim, Jeong-Eun Oh and Boyoung Y. Park
Catalysts 2021, 11(12), 1497; https://doi.org/10.3390/catal11121497 - 09 Dec 2021
Cited by 37 | Viewed by 7382
Abstract
Here, we review liquid organic hydrogen carriers (LOHCs) as a potential solution to the global warming problem due to the increased use of fossil fuels. Recently, hydrogen molecules have attracted attention as a sustainable energy carrier from renewable energy-rich regions to energy-deficient regions. [...] Read more.
Here, we review liquid organic hydrogen carriers (LOHCs) as a potential solution to the global warming problem due to the increased use of fossil fuels. Recently, hydrogen molecules have attracted attention as a sustainable energy carrier from renewable energy-rich regions to energy-deficient regions. The LOHC system is one a particularly promising hydrogen storage system in the “hydrogen economy”, and efficient hydrogen mass production that generates only benign byproducts can be applied in the industry. Therefore, this article presents hydrogenation and dehydrogenation, using homogeneous or heterogeneous catalysts, for several types of LOHCs, including formic acid/formaldehyde/ammonia, homocyclic compounds, nitrogen- and oxygen-containing compounds. In addition, it introduces LOHC system reactor types. Full article
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