5606103 Organotin catalyzed transesterification

Trapasso, L. E.; Meisel, P; Meisel, Lee B; Chwang, W. K.

doi:10.1016/s1381-1169(98)80103-9

Cited by 4 publications

(4 citation statements)

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“…(Trans)esterifications are widely applied in industry, e.g., in the synthesis of aspirin (acetylsalicylic acid), fatty acid esters, , polyesters, – and macrolides . More specifically, polylactones and polylactides are multipurpose, biocompatible, and biodegradable polyesters, used in biomedical and pharmaceutical applications. – …”

Section: Introductionmentioning

confidence: 99%

Undecyltin Trichloride Grafted onto Cross-Linked Polystyrene: An Efficient Catalyst for Ring-Opening Polymerization of ϵ-Caprolactone

et al. 2008

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The activity, recyclability, and chemical stability as a catalyst of undecyltin trichloride grafted to crosslinked polystyrene, [P-H] (1-t) [P-(CH 2 ) 11 -SnCl 3 ] t , with [P-H] the monomeric unit of the nonfunctionalized polymer and t the organotin-functionalized monomer fraction, are assessed in the ring-opening polymerization (ROP) of -caprolactone. Quantitative conversion is obtained within 2 h under conditions in which conversion is by far incomplete for two other organotin grafts, [P-H] (1-t) [P-(CH 2 ) 11 -SnBuCl 2 ] t and [P-H] (1-t) {[P-(CH 2 ) 11 -SnBuCl] 2 O} t/2 . Even after 15 min of reaction, conversions of at least 70% are achieved for the grafted tin trichloride. The catalytic reactions of the grafted undecyltin trichloride, more particularly its chemical integrity and recycling ability, are monitored, in situ, at the solid-liquid interface, using high-resolution magic angle spinning (HR-MAS) 1 H and 119 Sn NMR. Residual tin contents in the reaction products were assessed by inductively coupled plasma/atomic emission spectroscopy (ICP/AES). The polydispersity index of the synthesized poly( -caprolactone), investigated with size exclusion chromatography, is closer to unity than for grafted tin dichloride catalysts.

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Section: Introductionmentioning

confidence: 99%

Undecyltin Trichloride Grafted onto Cross-Linked Polystyrene: An Efficient Catalyst for Ring-Opening Polymerization of ϵ-Caprolactone

et al. 2008

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“…5 Despite their versatility, actual applications of these products are hampered by their toxicity, since they are often difficult to remove completely from the reaction mixture, especially when the process is conducted on an industrial scale. 6 This leads to organotin contamination of the final product and to inconvenient losses of catalyst. In order to overcome these drawbacks, the organotin moiety can be grafted onto an insoluble polymeric support, allowing the catalyst to be recovered by simple filtration and easily recycled after reaction.…”

Section: Introductionmentioning

confidence: 99%

Cross-linked resins functionalized with triorganotin carboxylates: synthesis, characterization and preliminary catalytic screening in transesterification

Angiolini¹,

Caretti²,

Mazzocchetti³

et al. 2005

Appl. Organometal. Chem.

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Cross-linked polymers containing triorganotin carboxylate functionalities were synthesized from ionic exchange resins bearing carboxylic groups. The organic tin substituents selected were methyl and butyl in order to ensure different accessibility at the metal centre. The functionalization degree depends on the different substituents and strongly affects the thermal stability of the final product. Catalytic screenings were performed in order to assess the activity of the above resins in transesterification reactions, using ethyl acetate as a substrate, together with differently hindered alcohols. The results obtained point to a negligible role of the bulkiness of tin substituents with a small contribution of the metal atom Lewis acidity in the conversion of the primary alcohol, whereas with secondary and tertiary alcohols the steric hindrance of the reagent strongly affects the conversion of the reacting alcohol. The transesterification process takes place at the liquid-solid interface, so that the catalyst grafted to an insoluble solid support can be completely removed by simple filtration.

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“…In the literature, it is reported that basic catalysts such as alkali metals, alkaline earth metals and their oxides, hydrides, and amides, as well as basic metal oxides revealed high catalytic activity in the melt process [8][9][10] . Furthermore, a variety of patents claimed the use of organometal compounds 8 , especially organotin compounds 11 . Some experiments have shown that organotin compounds have lower catalytic activity than alkaline-earth metals (100-200 times lower), although utilizing it did not lead to drastic discolouration effects, which could be one of their advantages in industrial applications 12 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Epoxidation of cis‐Enriched New Polycarbonates Catalyzed by Efficient Organotin Compound

Massoudi

Ramazanian

Vahedi

et al. 2011

Journal of Chemistry

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Presence of active functional groups on polymer chain is a suitable aspect of polymer structure which allows performing next favourite reactions on polymer molecule. In this research a novel aromatic derivative ofcis-but-2-endiol was synthesized as monomer. The synthesized monomer was polymerized using diphenyl carbonate and 1,4-butandiol as second and third monomer along with organotin catalyst. Polymerization reaction performed by using melt-phase transesterification process to produce a new terpolymer of polycarbonate. During the reaction the double bonds are preserved on polymer chain and epoxidized bym-chloroperbenzoic acid (MCBPA) in good yield to demonstrate the reactivity and possibility of performing further reactions on double bonds of polymer.

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5606103 Organotin catalyzed transesterification

Cited by 4 publications

References 0 publications

Undecyltin Trichloride Grafted onto Cross-Linked Polystyrene: An Efficient Catalyst for Ring-Opening Polymerization of ϵ-Caprolactone

Undecyltin Trichloride Grafted onto Cross-Linked Polystyrene: An Efficient Catalyst for Ring-Opening Polymerization of ϵ-Caprolactone

Cross-linked resins functionalized with triorganotin carboxylates: synthesis, characterization and preliminary catalytic screening in transesterification

Synthesis, Characterization and Epoxidation of cis‐Enriched New Polycarbonates Catalyzed by Efficient Organotin Compound

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