Alternating ring-opening copolymerization of cyclohexene oxide with phthalic anhydride catalyzed by iron(III) salen complexes

Mundil, Robert; Hošťálek, Z.; Šeděnková, Ivana; Merna, Jan

doi:10.1007/s13233-015-3022-4

Cited by 43 publications

(60 citation statements)

References 24 publications

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“…The asymmetric and symmetric stretching vibrations of the C O C group are attributed to the bands at 1257 and 1066 cm −1 , respectively. 13 The bands corresponding to ester carbonyl as well as symmetric and symmetric C O C groups are also identified in the FTIR spectra of PE-H and PE-X. This indicated that the main structure of PE was retained in the PE-H and PE-X derivatives.…”

Section: Resultsmentioning

confidence: 83%

“…The FTIR spectrum of the PE confirmed the presence of an ester linkage by the appearance of symmetric stretching vibration of the ester carbonyl (CO) group at 1720 cm −1 (Figure ). The asymmetric and symmetric stretching vibrations of the COC group are attributed to the bands at 1257 and 1066 cm −1 , respectively . The bands corresponding to ester carbonyl as well as symmetric and symmetric COC groups are also identified in the FTIR spectra of PE‐H and PE‐X.…”

Section: Resultsmentioning

confidence: 90%

“…In particular, salen metal catalysts have been tested in the presence of auxiliary catalysts for their ability to promote the ROCOP of epoxides and anhydrides. Examples of salen metal complexes tested in this way have included zinc, magnesium, chromium, cobalt, manganese, iron, aluminum, and nickel complexes . These catalysts have yielded significantly higher activity in the presence of nucleophilic cocatalysts such as bis(triphenylphosphine)iminium salts ([PPN]X), 4‐(dimethylamino)pyridine (DMAP), phosphines, and ammonium salts.…”

Section: Introductionmentioning

confidence: 99%

“…Examples of salen metal complexes tested in this way have included zinc, magnesium, chromium, cobalt, manganese, iron, aluminum, and nickel complexes. [8][9][10][11][12][13][14] These catalysts have yielded significantly higher activity in the presence of nucleophilic cocatalysts such as bis(triphenylphosphine)iminium salts ([PPN]X), 4-(dimethylamino)pyridine (DMAP), phosphines, and ammonium salts. The ROCOP of cyclohexene oxide (CHO) with succinic anhydride (SA), phthalic anhydride (PA), and cyclopropane-1,2-dicarboxylic acid anhydride using different salen metal complexes such as those of Al, Cr, and Co, along with several cocatalysts including bis(triphenylphosphine) iminium chloride (PPNCl) and DMAP were conducted by Duchateau and coworkers.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of high molecular weight aromatic polyesters via integrated alternating ring‐opening copolymerization and chain extension methods

Cheng

Rabnawaz

Khan

et al. 2018

J of Applied Polymer Sci

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Due to their good mechanical properties, high molecular weight polyesters (PEs) are highly desirable for a wide range of applications especially in the packaging industry. However, the synthesis of high molecular weight polymers by energy efficient methods is difficult. In this study, a series of semi‐aromatic PEs were synthesized via the alternating ring‐opening copolymerization (ROCOP) of phthalic anhydride (PA) and cyclohexene oxide (CHO) using a salen chromium(III) complex as a catalyst and 4‐(dimethylamino)pyridine as a cocatalyst. By varying the molar ratios between CHO and PA, PEs of different molecular weights were obtained. Hexamethylene diisocyanate was used as a chain extender that further increased the molecular weights of these PEs. These chain extended aromatic polyesters (PE‐Xs) showed significant improvement in the glass transition temperature (Tg) values. Thus, integration of ROCOP with the chain extension method can be used as an effective strategy to prepare high molecular weight PEs with improved thermal stabilities and enhanced mechanical properties. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47200.

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Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of high molecular weight aromatic polyesters via integrated alternating ring‐opening copolymerization and chain extension methods

Cheng

Rabnawaz

Khan

et al. 2018

J of Applied Polymer Sci

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“…In recent years, mononuclear asymmetric catalysts have become a focus for catalytic ring‐opening polymerization for the formation of completely alternating polyesters. Mundil et al . synthesized three iron(III) Salen complexes and successfully used them as catalysts together with bis(triphenylphosphine)imide chloride (PPNCl) for the ROCOP of epoxycyclohexane (CHO) and phthalic anhydride (PA).…”

Section: Introductionmentioning

confidence: 99%

Ring‐opening copolymerization of epoxycyclohexane and phthalic anhydride catalyzed by the asymmetric Salen‐CrCl complex

Shi

Wen

et al. 2020

Polymer International

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A new metallic chromium complex with asymmetric salen ligand and ancillary chloride group (complex 1) has been synthesized and applied as co-catalytic system with bis(triphenylphosphine)iminium chloride (PPNCl) for the polymerization of epoxycyclohexane (CHO) and phthalic anhydride (PA). The catalyst loading, polymerization temperature, reaction time and type of cocatalyst were varied in order to explore the influences on the catalytic activity of 1. It was found that 1 exhibited relatively good activity in the catalytic copolymerization of PA and CHO to form the product with more than 90% ester linkage content under mild conditions after the addition of the PPNCl co-catalyst. This was in sharp contrast to the dinuclear [ONSO]CrCl analogue, where the resulting polymer with more than 97% ether units was achieved under identical conditions. According to the kinetic data, the apparent activation energy of CHO ring-opening copolymerization was 9.0 kJ mol −1 . A reasonable polymerization mechanism was proposed based on the interaction between the single-metal two-component catalyst system and the monomer.

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Bimetallic Chromium Catalysts with Chain Transfer Agents: A Route to Isotactic Poly(propylene oxide)s with Narrow Dispersities

2018

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Bimetallic chromium catalysts are investigated for the enantioselective polymerization of propylene oxide.T he catalyst is composed of two salen chromiumspecies linked by an alkylchain, the length of which significantly impacts the rate of polymerization. While the use of achloride initiator on the catalyst resulted in bimodal molecular weight distributions, switching to at rifluoroacetate initiating group and adding ad iol chain transfer agent afforded polymers of controllable molecular weight with low, unimodal dispersities.

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Alternating ring-opening copolymerization of cyclohexene oxide with phthalic anhydride catalyzed by iron(III) salen complexes

Cited by 43 publications

References 24 publications

Synthesis of high molecular weight aromatic polyesters via integrated alternating ring‐opening copolymerization and chain extension methods

Synthesis of high molecular weight aromatic polyesters via integrated alternating ring‐opening copolymerization and chain extension methods

Ring‐opening copolymerization of epoxycyclohexane and phthalic anhydride catalyzed by the asymmetric Salen‐CrCl complex

Bimetallic Chromium Catalysts with Chain Transfer Agents: A Route to Isotactic Poly(propylene oxide)s with Narrow Dispersities

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