Mechanistic elucidation of monoalkyltin(<scp>iv</scp>)-catalyzed esterification

Wolzak, Lukas A.; Hermans, Jan; Vries, F. de; Berg, Keimpe J. van den; Reek, Joost N. H.; Tromp, Moniek; Korstanje, Ties J.

doi:10.1039/d1cy00184a

Cited by 7 publications

(7 citation statements)

References 32 publications

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“…In any case, these structures demonstrate that (salen)Fe(III) complexes have two mutually cis coordination sites available during catalytic reactions. This might be relevant to (trans)esterification catalysis, since it has been argued that the role of the acidic catalyst in such reactions goes beyond that of simple Lewis acid and may involve more than a single carboxylate [50,51].…”

Section: Resultsmentioning

confidence: 99%

Parts-Per-Million (Salen)Fe(III) Homogeneous Catalysts for the Production of Biodiesel from Waste Cooking Oils

et al. 2022

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This work describes the application of a library of iron(III)-salen catalysts in the production of biodiesel from vegetable oils. The conversion of neutral soybean oil is complete within two hours at 160–180 °C with low catalyst loading (0.10 mol%). A comparative screening reveals that the catalysts containing acetate as a fifth ligand are the most performing, and these have been conveniently used to convert acidic and waste cooking oils (WCO). WCOs were used as received without further purification to produce biodiesel in high yield (85–90%) under optimized conditions (2 h at 180 °C, catalyst loading 0.1 mol%, oil to alcohol molar ratio 1:20). The iron content in the lipophilic and hydrophilic phases of the crude mixture was investigated and the residual concentration in biodiesel was found to be in the order of 10–14 ppm, comparable to that contained in biodiesels from other sources. Graphical Abstract

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Section: Resultsmentioning

confidence: 99%

Parts-Per-Million (Salen)Fe(III) Homogeneous Catalysts for the Production of Biodiesel from Waste Cooking Oils

et al. 2022

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“…3 Organotin(IV) compounds have therefore been employed as industrial catalysts for esterification, polyvinyl chloride (PVC) stabilization, and polyurethane formation, 4 and their use as catalyst continues to appear in the literature. [5][6][7][8][9][10][11] The carboxamide [-C(O)NH-] group is an important component for construction of ligand frameworks, and among them, pyridine-2,6-dicarboxamide fragments are remarkable in coordination chemistry. The dianionic tridentate donor set (N py , N À , N À ) can form metal complexes by generating two five-membered chelate rings between N py and σ-donating N amide groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characterization of diorganotin(IV) complexes with a tridentate N‐heterocyclic podand ligand and investigation of their catalytic activity in Baeyer–Villiger oxidation of cyclic ketones to lactones

Basu Baul,

Khatiwara,

Addepalli

et al. 2023

Applied Organom Chemis

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Diorganotin(IV) complexes of composition [Me2SnL] (1), [n‐Bu2SnL] (2), and [Bz2SnL] (3) were synthesized by reacting the N2,N6‐di(pyridin‐2‐yl)pyridine‐2,6‐dicarboxamide pro‐ligand (H2L, where H2 denotes the two acidic protons) with Me2SnO, n‐Bu2SnO, and Bz2SnO, respectively, in refluxing toluene. The amide ligand leads to highly stable diorganotin(IV) complexes via the dianionic tridentate donor set (Npy, N−, N−) with pendent pyridine arms, and the coordination domain is completed by the respective two alkyl ligands. Solution‐state structures of the compounds 1–3 were studied by 1H, 13C, and 119Sn nuclear magnetic resonance (NMR) spectroscopy, revealing that the complexes adopt a five‐coordinate structure in non‐coordinating solvent. Additionally, homogenity and purity of the bulk materials of 1–3 were judged using the high‐resolution mass spectrometry in acetonitrile solution. The molecular and crystal structures of 1·0.5C6H6, 2, and 3 in the solid phase were established by single‐crystal X‐ray diffraction analysis. For all three compounds, the core defined by the rigid tridentate pyridine dicarboxamide ligand and the Sn‐coordinating C atoms adopts nearly C2v symmetry and thus matches none of the most popular geometries for five‐coordinated species, namely square‐pyramidal or trigonal‐bipyramidal coordination. Thermogravimetric analysis (TGA) was performed to probe the thermal stabilities of 1–3. The results serve as a basis for designing highly efficient diorganotin(IV) mimics for catalytic applications. Catalytic studies of ε‐caprolactone formation via Baeyer–Villiger oxidation of cyclohexanone with aqueous H2O2 were performed under microwave (MW) irradiation. The consequences of several reaction parameters like catalyst quantity, time, temperature, and solvent were studied.

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“…This approach will allow to get the commercially valuable esters in an efficient, sustainable and economical way [23,24]. Despite the esterification of acids can be viewed as an amortized reaction with little room for improvement, new catalysts have appeared in the last years that point towards new directions [25][26][27][28][29][30]. Solid catalysts allow to perform the esterification reaction on fixed-bed reactors, which offer numerous advantages over the batch reactors used so far.…”

Section: Introductionmentioning

confidence: 99%

Solid–catalyzed esterification reaction of long–chain acids and alcohols in fixed–bed reactors at pilot plant scale

Martínez–Castelló¹,

Tejeda–Serrano

Nowacka

et al. 2022

Chemical Engineering and Processing - Process Intensification

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Mechanistic elucidation of monoalkyltin(iv)-catalyzed esterification

Abstract: Monoalkyltin(IV) complexes are well‐known catalysts for esterification reactions and polyester formation, yet the mode of operation of these Lewis acidic complexes is still unknown. Here, we report on mechanistic studies...

Cited by 7 publications

References 32 publications

Parts-Per-Million (Salen)Fe(III) Homogeneous Catalysts for the Production of Biodiesel from Waste Cooking Oils

Parts-Per-Million (Salen)Fe(III) Homogeneous Catalysts for the Production of Biodiesel from Waste Cooking Oils

Synthesis and structural characterization of diorganotin(IV) complexes with a tridentate N‐heterocyclic podand ligand and investigation of their catalytic activity in Baeyer–Villiger oxidation of cyclic ketones to lactones

Solid–catalyzed esterification reaction of long–chain acids and alcohols in fixed–bed reactors at pilot plant scale

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