Polylactones, 52. Tin Carboxylates as Initiators ofɛ-Caprolactone

Kricheldorf, Hans R.; Stricker, Andrea; Langanke, Dennis

doi:10.1002/1521-3935(20011001)202:15<2963::aid-macp2963>3.0.co;2-c

Cited by 38 publications

(25 citation statements)

References 13 publications

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“…The central tin atom remains five-coordinated having distorted trigonal bipyramidal geometry. The Sn1-O1 (2.237(5) A), Sn1-O3 (2.163(5) A) and (6) (16), C1-Sn1-C10 169.6(2), O1-Sn1-C1 91.19 (18), O1-Sn1-C10 98.90 (17), O4-Sn1-C1 84.4(2), O2-Sn1-C10 93.52 (17). Sn1-O5 (2.092(4) A) interatomic distances are within the range of SneO distances of previously discussed 2 (Sn1-O1 2.187(3) A), 3 (Sn1-O1 2.114(3) A and Sn1-O3 2.108(3) A) or in already published zwitterionic stannate L CN (n-Bu) 2 SnOC(O)CF 3 $CF 3 COOH [15] (Sn1-O1 2.232(2) A and Sn1-O3 2.334(2) A).…”

Section: Hydrolysis Of Instable Diorganotin(iv) Bis(trifluoroacetates)mentioning

confidence: 99%

“…7). There is a difference between the OeC interatomic distances in bridging (nearly symmetric O2-C19 1.253(4) A and O3-C19 1.240(4) A; symmetric O4-C21 1.251(4) A and O5-C21 1.251(4) A) and (6), Sn1-O4 2.256(4), Sn2-O1 2.134(4), Sn2-O5 2.327(4), Sn2-O6 2.170(5), Sn2-O7 3.545(5), Sn1-N1 2.425(6), Sn2-N2 2.465(5), Sn1-C1 2.120(6), Sn2-C20 2.126(6), Sn1-C10 2.123(6), Sn2-C29 2.115(6), O2-C16 1.255 (7), O3-C16 1.199(10), O4-C18 1.247(8), O5-C18 1.224 (7), O6-C35 1.120(10), O7-C35 1.233(9), Sn1-O1-Sn2 142.27 (18), O1-Sn1-N1 167.76 (17), O1-Sn2-N2 174.02 (17), O2-Sn1-O4 177.15 (13), O5-Sn2-O6 166.38 (18), C1-Sn1-C10 164.0(2), C20-Sn2-C29 159.8(2), N1-Sn1-C1 76.0(2), N2-Sn2-C20 76.1(2). H-bonding (visualized by dashed line): O1-O3 2.727 (7), O1-H1.O3 147.4. monodentate (O6-C23 1.268(4) A and O7-C23 1.212(5) A; O8-C25 1.270(5) A and O9-C25 1.213(5) A) trifluoroacetate substituents.…”

Section: Instability Of Cn-chelated Tin(iv) Tris(trifluoroacetate)mentioning

confidence: 99%

“…These two compounds (L NCN Sn(H 2 O)(OC(O)CF 3 ) 3 and presumably the ionic [L NCN Ph 2 Sn] þ [CF 3 COO]ˉwere prepared and structurally characterized recently [16]. Other known organotin(IV) trifluoroacetates are used in glycosidation of sugar peracetates [17], as initiators of the ringopening polymerization of 3-caprolactone [18], as precursors for AP CVD of fluorine-doped SnO 2 thin films [19] and are investigated as potential metal-based antitumor drugs [20], too.…”

Section: Introductionmentioning

confidence: 99%

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C,N-chelated organotin(IV) trifluoroacetates. Instability of the mono- and diorganotin(IV) derivatives.

Švec

Padělková

Růžička

et al. 2011

Journal of Organometallic Chemistry

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Section: Hydrolysis Of Instable Diorganotin(iv) Bis(trifluoroacetates)mentioning

confidence: 99%

Section: Instability Of Cn-chelated Tin(iv) Tris(trifluoroacetate)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

C,N-chelated organotin(IV) trifluoroacetates. Instability of the mono- and diorganotin(IV) derivatives.

Švec

Padělková

Růžička

et al. 2011

Journal of Organometallic Chemistry

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“…1D), the presence of a second series of oligomers, likewise, spaced by m/z 114 (i.e., m/z 1051.6 and 1165.6) and separated from the homolog peaks of the main series by m/z 104. It was attributed to PCL (Table 1) formally corresponding to a loss of the diethylenglycol unit from PCLD polymer and they were identified as PCL cyclic oligomers [21][22][23][24], previously reported as a possible degradation pathway of PCL (Fig. 1) [25].…”

Section: Maldi Mass Spectra Of Polymer Sectionsmentioning

confidence: 84%

Using MALDI-TOF MS imaging and LC-HRMS for the investigation of the degradation of polycaprolactone diol exposed to different wastewater treatments

et al. 2017

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Polymers are used in high amounts in a wide range of applications from biomedicine to industry. Because of the growing awareness of the increasing amounts of plastic wastes in the aquatic environment during recent years, the evaluation of their biodegradability deserves special attention. In the past, most efforts were dedicated to studying the biodegradation of polyesters in soil and compost, while very little research has been conducted on their fate in wastewater. Here, we assessed the ability of bacterial communities residing in the aerobic and denitrification tank from a wastewater treatment plant (WWTP) to degrade the polymeric ester polycaprolactone diol (PCLD; average molecular weight of 1250 Da). Following the incubation of the solid polymer in WWTP tanks, matrixassisted laser desorption/ionization-mass spectrometry imaging (MALDI-MSI) was used to provide evidence for hydrolytic reactions and to study differences in the spatial degradation on the PCLD surface. It was demonstrated that regardless of the wastewater type, the chemical structure on the PCLD surface underwent modifications after 7 days of exposure.Apart from the parent PCLD peak series in MALDI-MSI mass spectra, the presence of a second oligomer series with mass peaks spaced by m/z 114 (as in PCLD) was observed. It was proposed to correspond to polycaprolactone (PCL) originating from the hydrolytic cleavage of the diethylene glycol from PCLD. Their ion masses were detected at m/z 104 below the PCLD peaks and their structures were proposed as PCL cyclized oligomers. Differences in the spatial distribution of low MW ions (<800) between the aerobic and denitrifying exposed samples in MALDI MSI were also noticeable. While the ions at m/z 221.1, 247.1 and 449.2 predominated in the aerobic exposed sample, those at m/z 475.5 and 677.4 were characteristic of the denitrifying one. The MALDI-MSI measurements in the low mass range were complemented with LC-HRMS analysis to determine plausible structures of the major degradation products. Ten transformation products (TPs) were detected in the denitrifying wastewater experiment, five of them were the result of ester hydrolysis forming caprolactone oligomers (TPs 220, 334, 448, 562, and 676) while the other series corresponded to formation of PCL chain with a terminal diethylene glycol, likewise formed by ester hydrolysis (TPs 246, 360, 474, 588, and 702).

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“…Among these polyesters, poly(ε-caprolactone) (PCL), poly(lactide) (PLA), poly(glycolic acid) (PGA), and their copolymers are especially fascinating because of their potential applications as biomedical materials [2][3][4]. The ringopening polymerization (ROP) of lactides, and lactones is gaining increasing importance again as a major synthetic method after the discovery of organometallic compounds, such as oxides, carboxylates, and alkoxides, as a starting material for the synthesis of polyesters [5].…”

Section: Introductionmentioning

confidence: 99%

Octa-armed star-shaped poly(ε-caprolactone)s with a phthalocyanine core by ring-opening polymerization: Synthesis and characterization

Bílgín

Yağcı

2014

European Polymer Journal

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Polylactones, 52. Tin Carboxylates as Initiators ofɛ-Caprolactone

Cited by 38 publications

References 13 publications

C,N-chelated organotin(IV) trifluoroacetates. Instability of the mono- and diorganotin(IV) derivatives.

C,N-chelated organotin(IV) trifluoroacetates. Instability of the mono- and diorganotin(IV) derivatives.

Using MALDI-TOF MS imaging and LC-HRMS for the investigation of the degradation of polycaprolactone diol exposed to different wastewater treatments

Octa-armed star-shaped poly(ε-caprolactone)s with a phthalocyanine core by ring-opening polymerization: Synthesis and characterization

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