Esterification, transesterification and hydrogenation reactions of polyunsaturated compounds catalyzed by a recyclable polymer supported palladium catalyst

Dell’Anna, Maria Michela; Capodiferro, Vito Filippo; Mali, Matilda; Mastrorilli, Piero

doi:10.1016/j.jorganchem.2016.06.001

Cited by 21 publications

(14 citation statements)

References 41 publications

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“…Petroleum ether/EtOAc = 10/1. 1 Methyl 3-phenylpropanoate (2o): 48 Light yellow oil; yield: 96% (204.7 mg). Eluent: petroleum ether/ EtOAc = 10/1.…”

Section: Methodsmentioning

confidence: 99%

PCl₃-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

Zhou

et al. 2021

Journal of Chemical Research

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A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

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“…Petroleum ether/EtOAc = 10/1. 1 Methyl 3-phenylpropanoate (2o): 48 Light yellow oil; yield: 96% (204.7 mg). Eluent: petroleum ether/ EtOAc = 10/1.…”

Section: Methodsmentioning

confidence: 99%

PCl₃-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

Zhou

et al. 2021

Journal of Chemical Research

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“…For this reason, developing convenient and effective procedures for converting WCO into a valuable biofuel is still a challenging goal. Recently, we scrutinized new catalytic systems based on polymer-supported palladium (Pd-pol) and nickel (Ni-pol) nanoparticles in the hydrogenation [25,26] and catalytic transfer hydrogenation [27,28] of several substrates under sustainable conditions, even in aqueous media [29]. Both catalysts were obtained through the co-polymerization of the metal containing monomer M(AAEMA) 2 (M = Pd, Ni; AEEMA − = deprotonated form of 2-(acetoacetoxy)ethyl methacrylate)) with co-monomers (ethyl methacrylate for Pd and N,N-dimethylacrilamide for Ni) and cross-linkers (ethylene glycol dimethacrylate for Pd and N,N'-methylene bis-acrylamide for Ni), followed by reduction.…”

Section: Catalystsmentioning

confidence: 99%

Partial Hydrogenation of Soybean and Waste Cooking Oil Biodiesel over Recyclable-Polymer-Supported Pd and Ni Nanoparticles

et al. 2022

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Biodiesel obtained through the transesterification in methanol of vegetable oils, such as soybean oil (SO) and waste cooking oil (WCO), cannot be used as a biofuel for automotive applications due to the presence of polyunsaturated fatty esters, which have a detrimental effect on oxidation stability (OS). A method of upgrading this material is the catalytic partial hydrogenation of the fatty acid methyl ester (FAME) mixture. The target molecule of the partial hydrogenation reaction is monounsaturated methyl oleate (C18:1), which represents a good compromise between OS and the cold filter plugging point (CFPP) value, which becomes too high if the biodiesel consists of unsaturated fatty esters only. In the present work, polymer-supported palladium (Pd-pol) and nickel (Ni-pol) nanoparticles were separately tested as catalysts for upgrading SO and WCO biodiesels under mild conditions (room temperature for Pd-pol and T = 100 °C for Ni-pol) using dihydrogen (p = 10 bar) as the reductant. Both catalysts were obtained through co-polymerization of the metal containing monomer M(AAEMA)2 (M = Pd, Ni; AEEMA− = deprotonated form of 2-(acetoacetoxy)ethyl methacrylate)) with co-monomers (ethyl methacrylate for Pd and N,N-dimethylacrilamide for Ni) and cross-linkers (ethylene glycol dimethacrylate for Pd and N,N’-methylene bis-acrylamide for Ni), followed by reduction. The Pd-pol system became very active in the hydrogenation of C=C double bonds, but poorly selective towards the desirable C18:1 product. The Ni-pol catalyst was less active than Pd-pol, but very selective towards the mono-unsaturated product. Recyclability tests demonstrated that the Ni-based system retained its activity and selectivity with both the SO and WCO substrates for at least five subsequent runs, thus representing an opportunity for waste biomass valorization.

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“…Pd-pol also proved to accelerate other kinds of chemical reactions such as reductions, oxidations and esterification. [ 54 , 55 , 56 , 57 , 58 , 59 ] However, the Pd-pol catalysed reductive amination was successful in one step by using aliphatic aldehydes only. In fact, when benzaldehydes were employed, the one-pot reaction was carried out in three steps to avoid benzyl alcohol formation ( Scheme 11 ).…”

Section: Metal-catalyzed One-pot Reductive Amination Reactionmentioning

confidence: 99%

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

et al. 2021

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Recently, N-substituted anilines have been the object of increasing research interest in the field of organic chemistry due to their role as key intermediates for the synthesis of important compounds such as polymers, dyes, drugs, agrochemicals and pharmaceutical products. Among the various methods reported in literature for the formation of C–N bonds to access secondary anilines, the one-pot reductive amination of aldehydes with nitroarenes is the most interesting procedure, because it allows to obtain diverse N-substituted aryl amines by simple reduction of nitro compounds followed by condensation with aldehydes and subsequent reduction of the imine intermediates. These kinds of tandem reactions are generally catalyzed by transition metal-based catalysts, mainly potentially reusable metal nanoparticles. The rapid growth in the last years in the field of metal-based heterogeneous catalysts for the one-pot reductive amination of aldehydes with nitroarenes demands for a review on the state of the art with a special emphasis on the different kinds of metals used as catalysts and their recyclability features.

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Esterification, transesterification and hydrogenation reactions of polyunsaturated compounds catalyzed by a recyclable polymer supported palladium catalyst

Cited by 21 publications

References 41 publications

PCl₃-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

PCl₃-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

Partial Hydrogenation of Soybean and Waste Cooking Oil Biodiesel over Recyclable-Polymer-Supported Pd and Ni Nanoparticles

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

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Esterification, transesterification and hydrogenation reactions of polyunsaturated compounds catalyzed by a recyclable polymer supported palladium catalyst

Cited by 21 publications

References 41 publications

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

Partial Hydrogenation of Soybean and Waste Cooking Oil Biodiesel over Recyclable-Polymer-Supported Pd and Ni Nanoparticles

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

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PCl₃-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

PCl₃-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation