Polymerisationsenthalpie der ringöffnenden polymerisation von cyclopenten (CPE) zu trans‐polypentenamer (TPR)

Kranz, Von Dietmar; Beck, Manfred

doi:10.1002/apmc.1972.050270102

Cited by 18 publications

(3 citation statements)

References 7 publications

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“…À4.5 kcal mol À1 was reported for polypentenamers containing 65% trans double bonds. 5 Similar data were reported later by Lebedev. 6 The thermodynamic study using WCl 6 /Al(C 2 H 5 )Cl 2 catalysts revealed that the cyclopentene conversion does not depend on the catalyst activity but the reaction temperature.…”

Section: Introductionsupporting

confidence: 83%

Ruthenium catalyzed equilibrium ring-opening metathesis polymerization of cyclopentene

2013

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Polypentenamer was synthetized by equilibrium ring-opening metathesis polymerization (ROMP) using well-defined ruthenium catalyst systems. It was found that the equilibrium time is influenced by the catalyst loading or the catalyst activity, however as expected, the overall cyclopentene conversion is determined only by the applied reaction temperature. Equilibrium of the growing chain and monomer was observed and the activation enthalpy and entropy were determined as: DH ¼ À5.6 kcal mol À1 ;. So far these values are the lowest which are reported for cyclopentene polymerization catalyst systems. This unique feature of the equilibrium polymerization opens a way for the synthesis of durable, environmentally friendly elastomers where tires can be not only synthetized but also readily recycled by the same transition metal catalyst system.

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Section: Introductionsupporting

confidence: 83%

Ruthenium catalyzed equilibrium ring-opening metathesis polymerization of cyclopentene

2013

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“…Considering the similar ring strain energies of CPD and CP , it was assumed that these two compounds should maintain similar thermodynamic properties in ROMP/ROCM reactions (Table ) ,. As expected for an equilibrium polymerization (e. g. ROMP of CP) using either Grubbs or WCl 6 /Al(C 2 H 5 )Cl 2 catalysts, the monomer equilibrium concentration is not affected by the catalyst activity but the reaction temperature ,…”

Section: Introductionsupporting

confidence: 58%

One‐pot Synthesis of 1,3‐Butadiene and 1,6‐Hexanediol Derivatives from Cyclopentadiene (CPD) via Tandem Olefin Metathesis Reactions

et al. 2018

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A novel tandem reaction of cyclopentadiene leading to high value linear chemicals via ruthenium catalyzed ring opening cross metathesis (ROCM), followed by cross metathesis (CM) is reported. The ROCM of cyclopentadiene (CPD) with ethylene using commercially available 2 nd gen. Grubbs metathesis catalysts (1-G2) gives 1,3-butadiene (BD) and 1,4-pentadiene (2) (and 1,4-cyclohexadiene (3)) with reasonable yields (up to 24 % (BD) and 67 % (2 + 3) at 73% CPD conversion) at 1-5 mol % catalyst loading in toluene solution (5 V% CPD, 10 bar, RT) in an equilibrium reaction. The ROCM of CPD with cis-butene diol diacetate (4) using 1.00 -0.05 mol % of 3 rd gen. Grubbs (1-G3) or 2 nd gen. Hoveyda-Grubbs (1-HG2) catalysts loading gives hexa-2,4-diene-1,6-diyl diacetate (5), which is a precursor of 1,6hexanediol (an intermediate in polyurethane, polyester and polyol synthesis) and hepta-2,5-diene-1,7-diyl diacetate (6) in good yield (up to 68 % or TON: 1180). Thus, convenient and selective synthetic procedures are revealed by ROCM of CPD with ethylene and 4 leading to BD and 1,6-hexanediol precursor, respectively, as key components of commercial intermediates of high-performance materials.

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“…Interestingly, polymerization to cis-polypentenamers had the smallest enthalpy change (∼−3.2 kcal mol −1 ), while the enthalpy changes of polymerization to 100% and 65% transpolypentenamer were found to be ∼−4.2 and ∼−4.5 kcal mol −1 , respectively (Table 1). 54 This difference in the enthalpy change of polymerization could be attributed to the relatively higher stability of the trans-alkene compared to its cis counterpart. The mechanism of depolymerization of polypentenamers was investigated by Korshak et al 55 and Badamshina et al 56 via the study of molecular weight and molecular weight distribution profiles over the course of depolymerization and will be discussed in Section 5.…”

Section: Depolymerizable Romp Polymersmentioning

confidence: 99%

Deconstruction of Polymers through Olefin Metathesis

Sathe,

Yoon,

Wang

et al. 2024

Chem. Rev.

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The consumption of synthetic polymers has ballooned; so has the amount of postconsumer waste generated. The current polymer economy, however, is largely linear with most of the post-consumer waste being either landfilled or incinerated. The lack of recycling, together with the sizable carbon footprint of the polymer industry, has led to major negative environmental impacts. Over the past few years, chemical recycling technologies have gained significant traction as a possible technological route to tackle these challenges. In this regard, olefin metathesis, with its versatility and ease of operation, has emerged as an attractive tool. Here, we discuss the developments in olefin-metathesis-based chemical recycling technologies, including the development of new materials and the application of olefin metathesis to the recycling of commercial materials. We delve into structure−reactivity relationships in the context of polymerization−depolymerization behavior, how experimental conditions influence deconstruction outcomes, and the reaction pathways underlying these approaches. We also look at the current hurdles in adopting these technologies and relevant future directions for the field.

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Polymerisationsenthalpie der ringöffnenden polymerisation von cyclopenten (CPE) zu trans‐polypentenamer (TPR)

Cited by 18 publications

References 7 publications

Ruthenium catalyzed equilibrium ring-opening metathesis polymerization of cyclopentene

Ruthenium catalyzed equilibrium ring-opening metathesis polymerization of cyclopentene

One‐pot Synthesis of 1,3‐Butadiene and 1,6‐Hexanediol Derivatives from Cyclopentadiene (CPD) via Tandem Olefin Metathesis Reactions

Deconstruction of Polymers through Olefin Metathesis

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