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17 pages, 8583 KiB

Open AccessArticle

Fabricated Gamma-Alumina-Supported Zinc Ferrite Catalyst for Solvent-Free Aerobic Oxidation of Cyclic Ethers to Lactones

by Naaser A. Y. Abduh, Abdullah A. Al-Kahtani, Mabrook S. Amer, Tahani Saad Algarni and Abdel-Basit Al-Odayni

Molecules 2023, 28(20), 7192; https://doi.org/10.3390/molecules28207192 - 20 Oct 2023

Cited by 1 | Viewed by 1407

Abstract

The aim of this work was to fabricate a new heterogeneous catalyst as zinc ferrite (ZF) supported on gamma-alumina (γ-Al₂O₃) for the conversion of cyclic ethers to the corresponding, more valuable lactones, using a solvent-free method and O₂ [...] Read more.

The aim of this work was to fabricate a new heterogeneous catalyst as zinc ferrite (ZF) supported on gamma-alumina (γ-Al₂O₃) for the conversion of cyclic ethers to the corresponding, more valuable lactones, using a solvent-free method and O₂ as an oxidant. Hence, the ZF@γ-Al₂O₃ catalyst was prepared using a deposition–coprecipitation method, then characterized using TEM, SEM, EDS, TGA, FTIR, XRD, ICP, XPS, and BET surface area, and further applied for aerobic oxidation of cyclic ethers. The structural analysis indicated spherical, uniform ZF particles of 24 nm dispersed on the alumina support. Importantly, the incorporation of ZF into the support influenced its texture, i.e., the surface area and pore size were reduced while the pore diameter was increased. The product identification indicated lactone compound as the major product for saturated cyclic ether oxidation. For THF as a model reaction, it was found that the supported catalyst was 3.2 times more potent towards the oxidation of cyclic ethers than the unsupported one. Furthermore, the low reactivity of the six-membered ethers can be tackled by optimizing the oxidant pressure and the reaction time. In the case of unsaturated ethers, deep oxidation and polymerization reactions were competitive oxidations. Furthermore, it was found that the supported catalyst maintained good stability and catalytic activity, even after four cycles. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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11 pages, 10614 KiB

Open AccessArticle

A Sustainable Green Enzymatic Method for Amide Bond Formation

by György Orsy, Sayeh Shahmohammadi and Enikő Forró

Molecules 2023, 28(15), 5706; https://doi.org/10.3390/molecules28155706 - 28 Jul 2023

Viewed by 1994

Abstract

A sustainable enzymatic strategy for the preparation of amides by using Candida antarctica lipase B as the biocatalyst and cyclopentyl methyl ether as a green and safe solvent was devised. The method is simple and efficient and it produces amides with excellent conversions [...] Read more.

A sustainable enzymatic strategy for the preparation of amides by using Candida antarctica lipase B as the biocatalyst and cyclopentyl methyl ether as a green and safe solvent was devised. The method is simple and efficient and it produces amides with excellent conversions and yields without the need for intensive purification steps. The scope of the reaction was extended to the preparation of 28 diverse amides using four different free carboxylic acids and seven primary and secondary amines, including cyclic amines. This enzymatic methodology has the potential to become a green and industrially reliable process for direct amide synthesis. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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11 pages, 2370 KiB

Open AccessArticle

Application of Chitosan/Poly(vinyl alcohol) Stabilized Copper Film Materials for the Borylation of α, β-Unsaturated Ketones, Morita-Baylis-Hillman Alcohols and Esters in Aqueous Phase

by Bojie Li, Wu Wen, Wei Wen, Haifeng Guo, Chengpeng Fu, Yaoyao Zhang and Lei Zhu

Molecules 2023, 28(14), 5609; https://doi.org/10.3390/molecules28145609 - 24 Jul 2023

Cited by 1 | Viewed by 1354

Abstract

A chitosan/poly(vinyl alcohol)-stabilized copper nanoparticle (CP@Cu NPs) was used as a heterogeneous catalyst for the borylation of α, β-unsaturated ketones, MBH alcohols, and MBH esters in mild conditions. This catalyst not only demonstrated remarkable efficiency in synthesizing organoboron compounds but also still maintained [...] Read more.

A chitosan/poly(vinyl alcohol)-stabilized copper nanoparticle (CP@Cu NPs) was used as a heterogeneous catalyst for the borylation of α, β-unsaturated ketones, MBH alcohols, and MBH esters in mild conditions. This catalyst not only demonstrated remarkable efficiency in synthesizing organoboron compounds but also still maintained excellent reactivity and stability even after seven recycled uses of the catalyst. This methodology provides a gentle and efficient approach to synthesize the organoboron compounds by efficiently constructing carbon–boron bonds. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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13 pages, 4132 KiB

Open AccessArticle

Highly Efficient Selective Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol over CoRe/TiO₂ Catalyst

by Mengting Chen, Yun Wang, Limin Jiang, Yuran Cheng, Yingxin Liu and Zuojun Wei

Molecules 2023, 28(8), 3336; https://doi.org/10.3390/molecules28083336 - 10 Apr 2023

Cited by 4 | Viewed by 2282

Abstract

Allylic alcohols typically produced through selective hydrogenation of α,β-unsaturated aldehydes are important intermediates in fine chemical industry, but it is still a challenge to achieve its high selectivity transformation. Herein, we report a series of TiO₂-supported CoRe bimetallic [...] Read more.

Allylic alcohols typically produced through selective hydrogenation of α,β-unsaturated aldehydes are important intermediates in fine chemical industry, but it is still a challenge to achieve its high selectivity transformation. Herein, we report a series of TiO₂-supported CoRe bimetallic catalysts for the selective hydrogenation of cinnamaldehyde (CAL) to cinnamyl alcohol (COL) using formic acid (FA) as a hydrogen donor. The resultant catalyst with the optimized Co/Re ratio of 1:1 can achieve an exceptional COL selectivity of 89% with a CAL conversion of 99% under mild conditions of 140 °C for 4 h, and the catalyst can be reused four times without loss of activity. Meanwhile, the Co₁Re₁/TiO₂/FA system was efficient for the selective hydrogenation of various α,β-unsaturated aldehydes to the corresponding α,β-unsaturated alcohols. The presence of ReO_x on the Co₁Re₁/TiO₂ catalyst surface was advantageous to the adsorption of C=O, and the ultrafine Co nanoparticles provided abundant hydrogenation active sites for the selective hydrogenation. Moreover, FA as a hydrogen donor improved the selectivity to α,β-unsaturated alcohols. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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15 pages, 6810 KiB

Open AccessArticle

Mesoporous Polymeric Ionic Liquid via Confined Polymerization for Laccase Immobilization towards Efficient Degradation of Phenolic Pollutants

by Yu Liang, Xinyan Chen, Jianli Zeng, Junqing Ye, Bin He, Wenjin Li and Jian Sun

Molecules 2023, 28(6), 2569; https://doi.org/10.3390/molecules28062569 - 12 Mar 2023

Cited by 3 | Viewed by 1985

Abstract

Laccase immobilization is a promising method that can be used for the recyclable treatment of refractory phenolic pollutants (e.g., chlorophenols) under mild conditions, but the method is still hindered by the trade-off limits of supports in terms of their high specific surface area [...] Read more.

Laccase immobilization is a promising method that can be used for the recyclable treatment of refractory phenolic pollutants (e.g., chlorophenols) under mild conditions, but the method is still hindered by the trade-off limits of supports in terms of their high specific surface area and rich functional groups. Herein, confined polymerization was applied to create abundant amino-functionalized polymeric ionic liquids (PILs) featuring a highly specific surface area and mesoporous structure for chemically immobilizing laccase. Benefiting from this strategy, the specific surface area of the as-synthesized PILs was significantly increased by 60-fold, from 5 to 302 m²/g. Further, a maximum activity recovery of 82% towards laccase was recorded. The tolerance and circulation of the immobilized laccase under harsh operating conditions were significantly improved, and the immobilized laccase retained more than 84% of its initial activity after 15 days. After 10 cycles, the immobilized laccase was still able to maintain 80% of its activity. Compared with the free laccase, the immobilized laccase exhibited enhanced stability in the biodegradation of 2,4-dichlorophenol (2,4-DCP), recording around 80% (seven cycles) efficiency. It is proposed that the synergistic effect between PILs and laccase plays an important role in the enhancement of stability and activity in phenolic pollutant degradation. This work provides a strategy for the development of synthetic methods for PILs and the improvement of immobilized laccase stability. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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15 pages, 1936 KiB

Open AccessArticle

Boron Lewis Acid Catalysis Enables the Direct Cyanation of Benzyl Alcohols by Means of Isonitrile as Cyanide Source

by Tong-Tong Xu, Jin-Lan Zhou, Guang-Yuan Cong, Jiang-Yi-Hui Sheng, Shi-Qi Wang, Yating Ma and Jian-Jun Feng

Molecules 2023, 28(5), 2174; https://doi.org/10.3390/molecules28052174 - 26 Feb 2023

Cited by 4 | Viewed by 3245

Abstract

The development of an efficient and straightforward method for cyanation of alcohols is of great value. However, the cyanation of alcohols always requires toxic cyanide sources. Herein, an unprecedented synthetic application of an isonitrile as a safer cyanide source in B(C₆F [...] Read more.

The development of an efficient and straightforward method for cyanation of alcohols is of great value. However, the cyanation of alcohols always requires toxic cyanide sources. Herein, an unprecedented synthetic application of an isonitrile as a safer cyanide source in B(C₆F₅)₃-catalyzed direct cyanation of alcohols is reported. With this approach, a wide range of valuable α-aryl nitriles was synthesized in good to excellent yields (up to 98%). The reaction can be scaled up and the practicability of this approach is further manifested in the synthesis of an anti-inflammatory drug, naproxen. Moreover, experimental studies were performed to illustrate the reaction mechanism. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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13 pages, 7008 KiB

Open AccessArticle

Theoretical Study on the Copper-Catalyzed ortho-Selective C-H Functionalization of Naphthols with α-Phenyl-α-Diazoesters

by Xiaoli Zhu, Xunshen Liu, Fei Xia and Lu Liu

Molecules 2023, 28(4), 1767; https://doi.org/10.3390/molecules28041767 - 13 Feb 2023

Cited by 3 | Viewed by 1943

Abstract

The aromatic C(sp²)-H functionalization of unprotected naphthols with α-phenyl-α-diazoesters under mild conditions catalyzed by CuCl and CuCl₂ exhibits high efficiency and unique ortho-selectivity. In this study, the combination of density functional theory (DFT) calculations and experiments [...] Read more.

The aromatic C(sp²)-H functionalization of unprotected naphthols with α-phenyl-α-diazoesters under mild conditions catalyzed by CuCl and CuCl₂ exhibits high efficiency and unique ortho-selectivity. In this study, the combination of density functional theory (DFT) calculations and experiments is employed to investigate the mechanism of C-H functionalization, which reveals the fundamental origin of the site-selectivity. It explains that CuCl-catalyzed ortho-selective C-H functionlization is due to the bimetallic carbene, which differs from the reaction catalyzed by CuCl₂ via monometallic carbene. The results demonstrate the function of favourable H-bond interactions on the site- and chemo-selectivity of reaction through stabilizing the rate-determining transition states in proton (1,3)-migration. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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15 pages, 3330 KiB

Open AccessArticle

Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

by Nuray Uzunlu, Péter Pongrácz, László Kollár and Attila Takács

Molecules 2023, 28(1), 442; https://doi.org/10.3390/molecules28010442 - 3 Jan 2023

Cited by 5 | Viewed by 2151

Abstract

In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that [...] Read more.

In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that the XantPhos ligand had a great influence on conversion (98%) and chemoselectivity (100% carboxamide), compared with the monodentate PPh₃. Following this study, the optimized conditions were used to extend the scope of substrates with nineteen candidates (various para-, ortho-, and meta-substituted iodobenzene derivatives and iodo-heteroarenes), as well as eight different amine nucleophiles. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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20 pages, 3775 KiB

Open AccessArticle

In Situ-Generated, Dispersed Cu Catalysts for the Catalytic Hydrogenolysis of Glycerol

by Iuliana Porukova, Vadim Samoilov, Dzhamalutdin Ramazanov, Mariia Kniazeva and Anton Maximov

Molecules 2022, 27(24), 8778; https://doi.org/10.3390/molecules27248778 - 11 Dec 2022

Viewed by 1880

Abstract

The present study is dedicated to the experimental verification of a concept for the hydrogenolysis of glycerol over in situ-generated Cu dispersed particles (Cu-DP). The Cu-DP were generated by in situ reduction of a precursor salt (Cu(OAc)₂, CuSO₄, CuCl [...] Read more.

The present study is dedicated to the experimental verification of a concept for the hydrogenolysis of glycerol over in situ-generated Cu dispersed particles (Cu-DP). The Cu-DP were generated by in situ reduction of a precursor salt (Cu(OAc)₂, CuSO₄, CuCl₂) in the presence of KOH and were active in glycerol conversion under hydrogen (T = 200–220 °C, p(H₂) = 1–4 MPa), where 1,2-propylene glycol (PG) and lactic acid (LA) were detected to be the main products. The influence of the reaction conditions (temperature, hydrogen pressure, reaction time, catalyst-to-feed ratio and the KOH/Cu ratio) on the yields of the products is described. It was shown that the selectivity between the PG and LA could be tuned by changing p(H₂) or by the KOH amount, i.e., higher yields of LA corresponded to lower p(H₂) and higher alkalinity of the reaction media. The activity of the in situ-generated Cu-DP was found to be comparable to that of an industrial Cu-Cr₂O₃ catalyst. The Cu-DP catalysts were characterized by XRD, XPS, HRTEM and SEM. During the reaction, the catalyst evolved by the sintering and recrystallization of the separate Cu-DP; the crystallite sizes after 1 and 15 h reaction times amounted to 35 and 49 nm, respectively. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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17 pages, 4784 KiB

Open AccessArticle

TiO₂ Catalyzed Dihydroxyacetone (DHA) Conversion in Water: Evidence That This Model Reaction Probes Basicity in Addition to Acidity

by Insaf Abdouli, Frederic Dappozze, Marion Eternot, Chantal Guillard and Nadine Essayem

Molecules 2022, 27(23), 8172; https://doi.org/10.3390/molecules27238172 - 24 Nov 2022

Cited by 5 | Viewed by 1966

Abstract

In this paper, evidence is provided that the model reaction of aqueous dihydroxyacetone (DHA) conversion is as sensitive to the TiO₂ catalysts’ basicity as to their acidity. Two parallel pathways transformed DHA: while the pathway catalyzed by Lewis acid sites gave pyruvaldehyde [...] Read more.

In this paper, evidence is provided that the model reaction of aqueous dihydroxyacetone (DHA) conversion is as sensitive to the TiO₂ catalysts’ basicity as to their acidity. Two parallel pathways transformed DHA: while the pathway catalyzed by Lewis acid sites gave pyruvaldehyde (PA) and lactic acid (LA), the base-catalyzed route afforded fructose. This is demonstrated on a series of six commercial TiO₂ samples and further confirmed by using two reference catalysts: niobic acid (NbOH), an acid catalyst, and a hydrotalcite (MgAlO), a basic catalyst. The original acid-base properties of the six commercial TiO₂ with variable structure and texture were investigated first by conventional methods in gas phase (FTIR or microcalorimetry of pyridine, NH₃ and CO₂ adsorption). A linear relationship between the initial rates of DHA condensation into hexoses and the total basic sites densities is highlighted accounting for the water tolerance of the TiO₂ basic sites whatever their strength. Rutile TiO₂ samples were the most basic ones. Besides, only the strongest TiO₂ Lewis acid sites were shown to be water tolerant and efficient for PA and LA formation. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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12 pages, 2837 KiB

Open AccessArticle

Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches

by Xiao-Yu Miao, Yong-Ji Hu, Fu-Rao Liu, Yuan-Yuan Sun, Die Sun, An-Xin Wu and Yan-Ping Zhu

Molecules 2022, 27(19), 6381; https://doi.org/10.3390/molecules27196381 - 27 Sep 2022

Cited by 6 | Viewed by 2203

Abstract

A cascade 6-endo-dig cyclization reaction was developed for the switchable synthesis of halogen and non-halogen-functionalized pyrazolo[3,4-b]pyridines from 5-aminopyrazoles and alkynyl aldehydes via C≡C bond activation with silver, iodine, or NBS. In addition to its wide substrate scope, the reaction showed good [...] Read more.

A cascade 6-endo-dig cyclization reaction was developed for the switchable synthesis of halogen and non-halogen-functionalized pyrazolo[3,4-b]pyridines from 5-aminopyrazoles and alkynyl aldehydes via C≡C bond activation with silver, iodine, or NBS. In addition to its wide substrate scope, the reaction showed good functional group tolerance as well as excellent regional selectivity. This new protocol manipulated three natural products, and the arylation, alkynylation, alkenylation, and selenization of iodine-functionalized products. These reactions demonstrated the potential applications of this new method. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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14 pages, 3023 KiB

Open AccessArticle

Homocouplings of Sodium Arenesulfinates: Selective Access to Symmetric Diaryl Sulfides and Diaryl Disulfides

by Xin-Zhang Yu, Wen-Long Wei, Yu-Lan Niu, Xing Li, Ming Wang and Wen-Chao Gao

Molecules 2022, 27(19), 6232; https://doi.org/10.3390/molecules27196232 - 22 Sep 2022

Cited by 7 | Viewed by 2227

Abstract

Symmetrical diaryl sulfides and diaryl disulfides have been efficiently and selectively constructed via the homocoupling of sodium arenesulfinates. The selectivity of products relied on the different reaction systems: symmetrical diaryl sulfides were predominately obtained under the Pd(OAc)₂ catalysis, whereas symmetrical diaryl sulfides [...] Read more.

Symmetrical diaryl sulfides and diaryl disulfides have been efficiently and selectively constructed via the homocoupling of sodium arenesulfinates. The selectivity of products relied on the different reaction systems: symmetrical diaryl sulfides were predominately obtained under the Pd(OAc)₂ catalysis, whereas symmetrical diaryl sulfides were exclusively yielded in the presence of the reductive Fe/HCl system. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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Review

Jump to: Research

26 pages, 1578 KiB

Open AccessReview

Comparsion of Catalyst Effectiveness in Different Chemical Depolymerization Methods of Poly(ethylene terephthalate)

by Marcin Muszyński, Janusz Nowicki, Mateusz Zygadło and Gabiela Dudek

Molecules 2023, 28(17), 6385; https://doi.org/10.3390/molecules28176385 - 31 Aug 2023

Cited by 7 | Viewed by 4759

Abstract

This paper presents an overview of the chemical recycling methods of polyethylene terephthalate (PET) described in the scientific literature in recent years. The review focused on methods of chemical recycling of PET including hydrolysis and broadly understood alcoholysis of polymer ester bonds including [...] Read more.

This paper presents an overview of the chemical recycling methods of polyethylene terephthalate (PET) described in the scientific literature in recent years. The review focused on methods of chemical recycling of PET including hydrolysis and broadly understood alcoholysis of polymer ester bonds including methanolysis, ethanolysis, glycolysis and reactions with higher alcohols. The depolymerization methods used in the literature are described, with particular emphasis on the use of homogeneous and heterogeneous catalysts and ionic liquids, as well as auxiliary substances such as solvents and cosolvents. Important process parameters such as temperature, reaction time, and pressure are compared. Detailed experimental results are presented focusing on reaction yields to allow for easy comparison of applied catalysts and for determination of the most favorable reaction conditions and methods. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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13 pages, 1539 KiB

Open AccessReview

Research Progress on Propylene Preparation by Propane Dehydrogenation

by Cheng Zuo and Qian Su

Molecules 2023, 28(8), 3594; https://doi.org/10.3390/molecules28083594 - 20 Apr 2023

Cited by 17 | Viewed by 5302

Abstract

At present, the production of propylene falls short of the demand, and, as the global economy grows, the demand for propylene is anticipated to increase even further. As such, there is an urgent requirement to identify a novel method for producing propylene that [...] Read more.

At present, the production of propylene falls short of the demand, and, as the global economy grows, the demand for propylene is anticipated to increase even further. As such, there is an urgent requirement to identify a novel method for producing propylene that is both practical and reliable. The primary approaches for preparing propylene are anaerobic and oxidative dehydrogenation, both of which present issues that are challenging to overcome. In contrast, chemical looping oxidative dehydrogenation circumvents the limitations of the aforementioned methods, and the performance of the oxygen carrier cycle in this method is superior and meets the criteria for industrialization. Consequently, there is considerable potential for the development of propylene production by means of chemical looping oxidative dehydrogenation. This paper provides a review of the catalysts and oxygen carriers employed in anaerobic dehydrogenation, oxidative dehydrogenation, and chemical looping oxidative dehydrogenation. Additionally, it outlines current directions and future opportunities for the advancement of oxygen carriers. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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31 pages, 5555 KiB

Open AccessReview

Silica-Based Supported Ionic Liquid-like Phases as Heterogeneous Catalysts

by Anna Wolny and Anna Chrobok

Molecules 2022, 27(18), 5900; https://doi.org/10.3390/molecules27185900 - 11 Sep 2022

Cited by 34 | Viewed by 4299

Abstract

Supported ionic liquid phases offer several advantages related with catalysis. Immobilization of ionic liquid on the solid support provides catalytic activity or efficient matrix for active phases, as enzymes or metal compounds. Ionic liquid can be physically adsorbed on the carrier (supported ionic [...] Read more.

Supported ionic liquid phases offer several advantages related with catalysis. Immobilization of ionic liquid on the solid support provides catalytic activity or efficient matrix for active phases, as enzymes or metal compounds. Ionic liquid can be physically adsorbed on the carrier (supported ionic liquid phase) or chemically grafted to the material surface (supported ionic liquid-like phase). The use of supported ionic liquid phases improves mass transport, reduces ionic amount in the process and, most importantly, enables effortless catalyst separation and recycling. Moreover, chemical modification of the surface material with ionic liquid prevents its leaching, enhancing length of catalyst life. Silica-based materials have become an effective and powerful matrix for supported ionic liquid-like phase due to its cost-efficiency, presence of hydroxyl groups on the surface enabling its functionalization, and specific material properties, such as the size and shapes of the pores. For these reasons, supported ionic liquid-like phase silica-based materials are successfully used in the organic catalysis. Full article

(This article belongs to the Special Issue Catalysis for Green Chemistry)

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