Synthesis of biodegradable polycarbonate by alternating copolymerization of carbon dioxide and propylene oxide using a cobalt/Schiff base catalyst

Li, Hongchun; Niu, Yongsheng

doi:10.1016/j.reactfunctpolym.2010.11.026

Cited by 18 publications

(4 citation statements)

References 33 publications

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“…The possibility to synthesize well-defined polyether- block -poly(ester- alt -sulfide) was also demonstrated. In addition, the polymerizability of γ-substituted thiobutyrolactone was shown by preliminary experiments, which paves the way to a multitude of combinations between epoxides and γ-thiobutyrolactones considering the rich chemistry of both families of monomers. , The properties of this attractive class of functional, (bio)degradable, and ROS-sensitive alternating copolymers are currently under investigation.…”

Section: Discussionmentioning

confidence: 98%

“…Indeed, copolymer properties are dominated not only by comonomer composition but also their sequence distribution. A perfectly alternating structure can magnify the properties of the copolymer, e.g., as separation membranes or solubilities and thermal properties, or biodegradability . In 1998, Nishikubo and colleagues reported the alternating copolymerization of γ-thiobutyrolactone with oxiranes catalyzed by quaternary onium salts, affording poly(thioether- alt -ester)s with high dispersities ( Đ ) and low molar-mass control .…”

Section: Introductionmentioning

confidence: 99%

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Functional Poly(ester-alt-sulfide)s Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization of Oxiranes and γ-Thiobutyrolactones

et al. 2020

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The copolymerization of tert-butyl glycidyl ether (tBuGE), allyl glycidyl ether (AGE), ethoxyethyl glycidyl ether (EEGE) and 1,2-epoxybutane (BO) with γ-thiobutyrolactone was investigated using benzyl alcohol–phosphazene bases as initiating systems. The prepared copolymers display perfect (poly(ester-alt-sulfide)) alternating structures for all epoxide monomers as evidenced by 1H, 13C, and 2D NMR and MALDI–TOF mass spectrometry. A marked influence of the reaction temperature on the occurrence of transesterification side reactions has been evidenced. In particular, at elevated temperature, transesterification reactions led to the formation of alternating macrocycles. The choice of the phosphazene base (tBuP4, tBuP2, or tBuP1) has a strong impact on the system reactivity and on the control of the polymerization. The use of tBuP1 led to very slow polymerization rates. The polymerization is much faster in the presence of tBuP2 even at low temperature. The use of tBuP4 shows an intermediate polymerization rate and enabled a good polymerization control at moderate temperatures. Finally, the synthesis of well-defined polyether-block-poly(ester-alt-sulfide) and the polymerization of a challenging substituted γ-thiolactone were proven to be feasible.

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Section: Discussionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Functional Poly(ester-alt-sulfide)s Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization of Oxiranes and γ-Thiobutyrolactones

et al. 2020

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“…Also the terpolymerization with cyclic acid anhydrides is feasible. [157] Fundamentally, one differentiates between two distinct catalyst classes: in case of cobalt(III)-catalysts, [158][159][160][161] chromium(III)-salen and -salan complexes, [116,163] aluminum(III)-salen complexes [164] or Lewis acidic compounds [117,162] such as zinc glutarate, [165,166] zinc diiminate -ethylsulfinate [167] or rare-earth complexes [168] as catalysts, polyalkylenecarbonates with alternating repetition units are obtained; in contrast, if one uses double metal cyanide (DMC) catalysts, one acquires polyalkylenecarbonates, in which ether units occur besides the carbonate linkages. While alternating polypropylenecarbonate is on the market, the production of non-alternating polypropylenecarbonate is currently being commercialized.…”

Section: Productionmentioning

confidence: 99%

Chemical Technologies for Exploiting and Recycling Carbon Dioxideinto the Value Chain

et al. 2011

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While experts in various fields discuss the potential of carbon capture and storage (CCS) technologies, the utilization of carbon dioxide as chemical feedstock is also attracting renewed and rapidly growing interest. These approaches do not compete; rather, they are complementary: CCS aims to capture and store huge quantities of carbon dioxide, while the chemical exploitation of carbon dioxide aims to generate value and develop better and more-efficient processes from a limited part of the waste stream. Provided that the overall carbon footprint for the carbon dioxide-based process chain is competitive with conventional chemical production and that the reaction with the carbon dioxide molecule is enabled by the use of appropriate catalysts, carbon dioxide can be a promising carbon source with practically unlimited availability for a range of industrially relevant products. In addition, it can be used as a versatile processing fluid based on its remarkable physicochemical properties.

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“…Despite its contribution in global warming, CO 2 is an economical C1 resource with the advantages such as abundance, renewability and nontoxicity [1]. CO 2 has already been used in some industrial production processings including the productions of salicylic acid, urea and various carbonates [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polycarbonates by Copolymerization of Carbon Dioxide and Cyclohexene Oxide Using Schiff Base Complex as Catalyst

2015

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A novel Schiff base complex BCED-Zn has been found to be an effective catalyst for copolymerization of CO 2 and cyclohexene oxide to afford alternating copolymer poly(cyclohexenylene carbonate) (PCHC), and the turnover number was up to 421.1 at 110 • C and 4 MPa CO 2 pressure for 24 h. The influence of the reaction conditions such as reaction time, reaction temperature and CO 2 pressure was discussed and optimized. The thermal stability of PCHC was measured by thermogravimetric analysis, indicating that the 5 % weight loss temperature was about 232 • C and the maximum weight loss temperature was around 256 • C.

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Synthesis of biodegradable polycarbonate by alternating copolymerization of carbon dioxide and propylene oxide using a cobalt/Schiff base catalyst

Cited by 18 publications

References 33 publications

Functional Poly(ester-alt-sulfide)s Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization of Oxiranes and γ-Thiobutyrolactones

Functional Poly(ester-alt-sulfide)s Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization of Oxiranes and γ-Thiobutyrolactones

Chemical Technologies for Exploiting and Recycling Carbon Dioxideinto the Value Chain

Synthesis of Polycarbonates by Copolymerization of Carbon Dioxide and Cyclohexene Oxide Using Schiff Base Complex as Catalyst

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