Selectively catalytic hydrogenation of nitrile-butadiene rubber using Grubbs II catalyst

Ai, Chunjin; Gong, Guangbi; Zhao, Xutao; Liu, Peng

doi:10.1007/s13233-017-5058-0

Cited by 20 publications

(11 citation statements)

References 21 publications

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“…The hydrogenation of natural rubber and cis -1,4-polyisoprene has been reported by using a Ru-based catalyst (Ru(CHACH(Ph))Cl(CO)(PCy 3 ) 2 ). , In addition, a Grubbs catalyst was reported for the hydrogenation of −CC– bonds of a nitrile-butadiene rubber . In the present work, a first generation Grubbs catalyst was used for the hydrogenation experiments of the IP-GMA copolymers in order to investigate preliminary conditions for the hydrogenation of IP-GMA copolymers, and verify the performance of the catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…9,10 In addition, a Grubbs catalyst was reported for the hydrogenation of −C C− bonds of a nitrile-butadiene rubber. 25 In the present work, a first generation Grubbs catalyst was used for the hydrogenation experiments of the IP-GMA copolymers in order to investigate preliminary conditions for the hydrogenation of IP-GMA copolymers, and verify the performance of the catalyst. Hydrogenation of IP-GMA copolymers obtained by RAFT could be a challenge since the polar groups present in the GMA moiety and the trithiocarbonate functionality of the RAFT agent, both present in the copolymer chains, could deactivate the Grubbs catalyst.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Semiautomated Parallel RAFT Copolymerization of Isoprene with Glycidyl Methacrylate

et al. 2019

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Copolymerization of isoprene (IP) with glycidyl methacrylate (GMA) was performed under RAFT (reversible addition−fragmentation chain-transfer) polymerization conditions in a platform for high-output experimentation. Covering the range between 1 and 0.2 molar fraction of IP in the feed, four sets of reactions were carried out at 10, 15, 20, and 30 h at 115 °C. The kinetic data obtained were used to estimate the reactivity ratios using a nonlinear least-squares approach (NLLS). Reactivity ratios r GMA = 0.61 and r IP = 0.74 indicate that both monomers tend to crosspropagate in agreement with known literature values. Concerning the RAFT study, relatively good control and livingness of the copolymerization was observed except for the experiment in which IP represents 20 mol % in the feed. 1 H NMR characterization confirmed the presence of both monomers in the final copolymer, particularly the presence of the epoxy ring of GMA which is susceptible to post polymerization reactions. Finally, preliminary results on the hydrogenation of various polymers are discussed.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Semiautomated Parallel RAFT Copolymerization of Isoprene with Glycidyl Methacrylate

et al. 2019

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“…Olefin metathesis is an attractive route to depolymerization of unsaturated rubbers, critically enabled by the nuanced chain microstructure (1,4‐ and 1,2‐addition products) characteristic of polydienes. [ 45–64 ] Adjacent double bonds in side‐ and main‐chain configurations are ring‐closed by Ru carbenes (Grubbs’ catalysts) to cyclopentene and cyclohexene species with concomitant cleavage of the polymer chain. [ 48,57,64 ] The further realization that cyclopentene, functionalized cyclopentenes, and other five‐membered alkene rings can be ring‐opened through judicious selection of reaction conditions has spawned recent development of polypentenamer elastomers and related materials, including networks with continuous recyclability through sequential ring‐opening and ring‐closing metathesis.…”

Section: Methodsmentioning

confidence: 99%

Selectively Depolymerizable Polyurethanes from Unsaturated Polyols Cleavable by Olefin Metathesis

Jones

Staiger

Powers

et al. 2020

Macromol. Rapid Commun.

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This communication describes a novel series of linear and crosslinked polyurethanes (PUs) and their selective depolymerization under mild conditions. Two unique polyols are synthesized bearing unsaturated units in a configuration designed to favor ring‐closing metathesis (RCM) to five‐ and six‐membered cycloalkenes. These polyols are co‐polymerized with toluene diisocyanate to generate linear PUs and trifunctional hexamethylene‐ and diphenylmethane‐based isocyanates to generate crosslinked PUs. The polyol design is such that the RCM reaction cleaves the backbone of the polymer chain. Upon exposure to dilute solutions of Grubbs’ catalyst under ambient conditions, the PUs are rapidly depolymerized to low molecular weight, soluble products bearing vinyl and cycloalkene functionalities. These functionalities enable further re‐polymerization by traditional strategies for polymerization of double bonds. It is anticipated that this general approach can be expanded to develop a range of chemically recyclable condensation polymers that are readily depolymerized by orthogonal metathesis chemistry.

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“…Based on a kinetic analysis of the hydrogenation process via a homogeneous catalytic route, Ai et al found that a hydrogenation degree of 75 mol% was achieved with 6 mg Grubbs II catalyst at 3 h in 100 mL toluene solution of 1.0 g NBR under 725 psi hydrogen (H 2 ) pressure and at 55 • C [8]. In the case of heterogeneous catalysis [9][10][11][12], silica and carbon nanotubes were introduced as catalyst carriers for hydrogenation reaction.…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation of Carboxyl Nitrile Butadiene Rubber Latex Using a Ruthenium-Based Catalyst

Liu

Zhou

et al. 2022

Catalysts

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Hydrogenated carboxyl nitrile rubber (HXNBR) is endowed with superior mechanical performance and heat–oxygen aging resistance via emulsion hydrogenation of its precursor, i.e., carboxyl nitrile rubber (XNBR). Herein, a ruthenium-based catalyst was prepared to achieve the direct catalytic hydrogenation of XNBR latex. The effects of a series of hydrogenation conditions, such as catalyst dosage, solid content and reaction temperature, as well as the hydrogen pressure, on the hydrogenation reaction were investigated in detail. We found that the hydrogenation rate fell upon increasing the solid content of the XNBR latex, with an XNBR conversion rate of 95.01 mol% in 7 h with 11.25 wt% solid content. As the reaction temperature was increased, the hydrogenation rate first increased and then decreased. The fastest reaction hydrogenation rate was reached at 140 °C, with an XNBR conversion of 95.10 mol% in 5 h. The hydrogenation rate was positively related with the hydrogen pressure employed in the reactor. In view of the safety and cost, a pressure rate of 1300 psi was considered optimal. Similarly, the hydrogenation rate can also be enhanced by adding more catalyst. When 0.05 wt% catalyst was added, the fastest hydrogenation rate was achieved. In summary, the following optimum hydrogenation conditions were determined by using a synthesized ruthenium-based catalyst: 11.25 wt% solid content of XNBR latex, 140 °C of reaction temperature, 1300 psi of hydrogen pressure and 0.05 wt% catalyst. The vulcanization, mechanical performance, aging resistance and oil resistance of the produced HXNBR under the above reaction conditions were systematically investigated.

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Selectively catalytic hydrogenation of nitrile-butadiene rubber using Grubbs II catalyst

Cited by 20 publications

References 21 publications

Semiautomated Parallel RAFT Copolymerization of Isoprene with Glycidyl Methacrylate

Semiautomated Parallel RAFT Copolymerization of Isoprene with Glycidyl Methacrylate

Selectively Depolymerizable Polyurethanes from Unsaturated Polyols Cleavable by Olefin Metathesis

Hydrogenation of Carboxyl Nitrile Butadiene Rubber Latex Using a Ruthenium-Based Catalyst

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