Metal-free transesterification catalyzed by tetramethylammonium methyl carbonate

Hatano, Manabu; Tabata, Yuji; Yoshida, Yurika; Toh, Kohei; Yamashita, Kenji; Ogura, Yoshihiro; Ishihara, Kazuaki

doi:10.1039/c7gc03858e

Cited by 34 publications

(25 citation statements)

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“…Examples of organocatalysis applied to polymer degradation has recently been reviewed; 50 specific examples of organocatalytic polyester degradation include TBD (for PLA and PET) 41,45,51,52 and DMAP (for PLA), 53 and ionic liquids (for PLA and PET). 40,[54][55][56] Herein, we report the use of a simple onium transesterification catalyst, first reported for monomeric substrates by Ishihara et al, 57 57 The synthesis of this catalyst (Fig. 1) was also scaled up from the reported method.…”

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confidence: 99%

“…With the addition of alcohol, the carbonate anion is replaced by an alkoxide which can then perform transesterification with the assistance of the methyl hydrogen atoms acting as Brønsted acids to activate the carbonyl group (Scheme S1 †). 57 The ability of these hydrogen atoms to hydrogen bond has previously been demonstrated, and is achieved through delocalisation of the positive charge. [58][59][60] For PLA, degradation was initially performed at 50°C in line with previous studies, 46,61 using 4 wt% of 1 (2.0 mol% with respect to ester linkages; Table 1, entry 1).…”

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Organocatalysis for versatile polymer degradation

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Organocatalysis for versatile polymer degradation

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“…In addition to that, the combination of a Ti(O i -Pr) 4 -catalysed polycarbonate vitrimer matrix and natural cellulose has been proven appealing for novel green composites [ 78 ]. As a side note, Hatano and coworkers recently endeavoured to introduce a metal-free transesterification catalyst based on tetramethylammonium methyl carbonate [ 79 ].…”

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confidence: 99%

The Impact of Vitrimers on the Industry of the Future: Chemistry, Properties and Sustainable Forward-Looking Applications

2020

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Thermosets are known to be very reliable polymeric materials for high-performance and light-weight applications, due to their retained dimensional stability, chemical inertia and rigidity over a broad range of temperatures. However, once fully cured, they cannot be easily reshaped or reprocessed, thus leaving still unsolved the issues of recycling and the lack of technological flexibility. Vitrimers, introduced by Leibler et al. in 2011, are a valiant step in the direction of bridging the chasm between thermoplastics and thermosets. Owing to their dynamic covalent networks, they can retain mechanical stability and solvent resistance, but can also flow on demand upon heating. More generally, the family of Covalent Adaptable Networks (CANs) is gleaming with astounding potential, thanks to the huge variety of chemistries that may enable bond exchange. Arising from this signature feature, intriguing properties such as self-healing, recyclability and weldability may expand the horizons for thermosets in terms of improved life-span, sustainability and overall enhanced functionality and versatility. In this review, we present a comprehensive overview of the most promising studies featuring CANs and vitrimers specifically, with particular regard for their industrial applications. Investigations into composites and sustainable vitrimers from epoxy-based and elastomeric networks are covered in detail.

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“… [11] However, the two factors of (1) equilibrium nature and reversibility of the reaction and (2) the low reactivity of the ester functional group, are two limiting factors for achieving the desired selectivity/efficiency for this reaction. [ 13 , 14 ]…”

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Metal‐ and Solvent‐Free Transesterification and Aldol Condensation Reactions by a Homogenous Recyclable Basic Ionic Liquid Based on the 1,3,5‐Triazine Framework

Ren

Kazemnejadi

2021

ChemistryOpen

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A new recyclable basic ionic liquid was introduced as an efficient catalyst for aldol condensation and transesterification reactions under environmentally friendly conditions. The catalyst was prepared based on methyl imidazolium moieties bearing hydroxide counter anions via the Hofmann elimination on a 1,3,5‐triazine framework. The ionic liquid with two functionalities including anion stabilizer and high basicity, was used as an efficient catalyst for aldol condensation as well as transesterification reaction of a variety of alkyl benzoates. All reactions were performed in the absence of any external reagent, co‐catalyst, or solvent, in line with environmental protection. The kinetics isotope effect (KIE) was conducted for the transesterification reaction to elucidate the mechanism and rate determining step (RDS). It worth noted that, the homogeneous catalyst could be recycled from the reaction mixture and reused for several consecutive runs with insignificant drop of basicity and conversion.

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Metal-free transesterification catalyzed by tetramethylammonium methyl carbonate

Abstract: A metal-free [Me4N]+[OCO2Me]− catalyst is effective for the chemoselective, scalable, and reusable transesterification of chelating substrates in common organic solvents.

Cited by 34 publications

References 112 publications

Organocatalysis for versatile polymer degradation

Organocatalysis for versatile polymer degradation

The Impact of Vitrimers on the Industry of the Future: Chemistry, Properties and Sustainable Forward-Looking Applications

Metal‐ and Solvent‐Free Transesterification and Aldol Condensation Reactions by a Homogenous Recyclable Basic Ionic Liquid Based on the 1,3,5‐Triazine Framework

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