Influence of coordinating groups of organotin compounds on the Fries rearrangement of diphenyl carbonate

Liu, Tao; Yuan, Xiaoxue; Zhang, Gang; Zeng, Yi; Chen, Tong; Wang, Gongying

doi:10.1039/c9ra05390e

Cited by 6 publications

(5 citation statements)

References 32 publications

(21 reference statements)

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“…On the other hand, a homogeneous catalyst has higher activity and selectivity, which is closer to industrial application. Among the homogeneous catalysts such as organic titanium compounds [14][15][16], organotin compounds [17], and samarium diiodide [18], titanium alkoxides show high activity for this reaction. However, most titanium alkoxides are sensi-tive to water and easily deactivated by hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

Stable Organic Titanium Catalysts and Reactive Distillation Used for the Transesterification of Dimethyl Carbonate with Phenol

Shen

et al. 2020

Chem Eng & Technol

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The transesterification of dimethyl carbonate with phenol to methyl phenyl carbonate (MPC) was investigated on novel catalysts such as titanium diisopropoxide bis(ethyl acetoacetate) and titanium dibutoxide bis(ethyl acetoacetate) in a closed batch reactor at 185-206°C under high pressure. The produced methanol could be removed efficiently by reactive distillation in order to overcome the equilibrium. The prepared catalysts have higher resistance to water than titanium alkoxides. Phenol conversion as high as 86.4 % with an MPC selectivity of 99.4 % was achieved under optimal reaction conditions within 9 h. Most of the catalytic activity was retained after repeated use for ten times.

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Section: Introductionmentioning

confidence: 99%

Stable Organic Titanium Catalysts and Reactive Distillation Used for the Transesterification of Dimethyl Carbonate with Phenol

Shen

et al. 2020

Chem Eng & Technol

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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%

“…Organotin(IV) compounds as catalyst have also reached distinct statures due to, in a great extent, absence of side reactions, good efficiency even under mild conditions, and encouraging toxicological and environmental properties 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 5–11 …”

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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“…In order to solve this problem, atomically precise tin-oxo clusters (TOCs) have emerged, and a few organotin clusters have been con-structed through the hydrolysis and condensation of alkyltin precursors [6][7][8][9][10]. As the cluster states of tin oxide, TOCs not only enrich the members of Sn-O materials, but also provide good opportunity for in-depth understanding of their structure-function relationships [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Non-alkyl tin-oxo clusters as new-type patterning materials for nanolithography

Wang

Zhang

2021

Sci. China Chem.

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Nanolithography plays crucial roles in the miniaturization of dense integrated circuit, which extremely depends on innovative resist materials. Recently, metal-containing resists have been explored due to their higher short-wavelength photon absorption than traditional polymer resists. Herein, for the first time, the patterning performance of non-alkyl tin-oxo clusters has been evaluated. Meanwhile, the influence of structural characteristics on resolution and sensitivity has been investigated. To evaluate the surface ligand effect, three non-alkyl Sn 10 -oxo clusters with the same core were functionalized with pyrazole, 3-methylpyrazole and 4-methylpyrazole, respectively. Furthermore, another Sn 14 -oxo cluster with similar core configuration was also prepared using 4-methylpyrazole ligand to study the influence of Sn nuclearity. Spin-coating method was then applied to fabricate thin films of these non-alkyl tin-oxo clusters on Si substrate, which showed various thicknesses and roughnesses. More interestingly, electron beam lithography (EBL) patterning studies indicated that for the same Sn 10 core, the 4-methylpyrazoledecorated clusters showed the best performance. As for the different cluster cores with the same 4-methylpyrazole ligand, the patterns of Sn 10 with the higher ligand:Sn ratio are also better than those of Sn 14 . Finally, distinguishable 50 nm resolution was achieved by 4-methylpyrazole-decorated Sn 10 at expose energy of 100 μC/cm 2 which can be significantly improved by increasing expose energy to 1,000 μC/cm 2 as confirmed by atomic force microscopy (AFM) images. This work not only opens the nanolithography applications of non-alkyl tin-oxo clusters, but also provides an effective structural methodology for improving their patterning performance in future.

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Influence of coordinating groups of organotin compounds on the Fries rearrangement of diphenyl carbonate

Abstract: In this paper, the Fries rearrangement of diphenyl carbonate (DPC) catalyzed by organotin compounds with different coordination groups was studied for the first time.

Cited by 6 publications

References 32 publications

Stable Organic Titanium Catalysts and Reactive Distillation Used for the Transesterification of Dimethyl Carbonate with Phenol

Stable Organic Titanium Catalysts and Reactive Distillation Used for the Transesterification of Dimethyl Carbonate with Phenol

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

Non-alkyl tin-oxo clusters as new-type patterning materials for nanolithography

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