Synthesis of polyacrylates from limonene by catalytic oxidation and multi-component reaction

Czapiewski, Marc von; Gugau, Katharina; Todorović, Lazar; Meier, Michael A. R.

doi:10.1016/j.eurpolymj.2016.08.034

Cited by 12 publications

(13 citation statements)

References 22 publications

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“…In this respect, we investigated isocyanide-based multicomponent reactions (MCRs), among which the Passerini three-component reaction and Ugi four-component reaction (Ugi-4CR) , are particularly interesting in polymer science due to their versatility. − For instance, the direct synthesis of polyamides and polyesteramides was achieved via the Ugi reaction. More recently, isocyanide-based MCRs were used for a variety of applications in polymer science ranging from monomer synthesis − to postpolymerization modification. ,− …”

Section: Introductionmentioning

confidence: 99%

Direct Catalytic Route to Biomass-Derived 2,5-Furandicarboxylic Acid and Its Use as Monomer in a Multicomponent Polymerization

Schade

Dannecker²,

Kalz

et al. 2019

ACS Omega

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Efficient synthesis of valuable platform chemicals from renewable feedstock is a challenging, yet essential strategy for developing technologies that are both economical and sustainable. In the present study, we investigated the synthesis of 2,5-furandicarboxylic acid (FDCA) in a two-step catalytic process starting from sucrose as largely available biomass feedstock. In the first step, 5-(hydroxymethyl)furfural (HMF) was synthesized by hydrolysis and dehydration of sucrose using sulfuric acid in a continuous reactor in 34% yield. In a second step, the resulting reaction solution was directly oxidized to FDCA without further purification over a Au/ZrO2 catalyst with 84% yield (87% selectivity, batch process), corresponding to 29% overall yield with respect to sucrose. This two-step process could afford the production of pure FDCA after the respective extraction/crystallization despite the impure intermediate HMF solution. To demonstrate the direct application of the biomass-derived FDCA as monomer, the isolated product was used for Ugi-multicomponent polymerizations, establishing a new application possibility for FDCA. In the future, this efficient two-step process strategy toward FDCA should be extended to further renewable feedstock.

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Section: Introductionmentioning

confidence: 99%

Direct Catalytic Route to Biomass-Derived 2,5-Furandicarboxylic Acid and Its Use as Monomer in a Multicomponent Polymerization

Schade

Dannecker²,

Kalz

et al. 2019

ACS Omega

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“…Moreover, the development of efficient techniques in the areas of controlled/living polymerization and effective functional‐group modification within the last few years has received renewed attention, because they offer enormous new possibilities and potency for the utilization of terpenes and terpenoids. To obtain sustainable monomers and polymers with highly developed architectures and excellent properties, the utilization of terpene as a renewable material has been comprehensively investigated and many environmentally benign methods and/or highly efficient reactions have been reported …”

Section: Terpenes As Promising Renewable Platform Chemicalsmentioning

confidence: 99%

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Firdaus

2017

Asian J Org Chem

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This Focus Review highlights the application of thiol-ene (click) chemistry to the productiono fadiverse range of materials that are derived from terpenes. To present an overview concerning the potencyo ft erpenes as renewable resources, recent advances in their developmentb y using synthetic organic chemistry are initially discussed. In addition, the use of thiol-enec hemistry as an efficient approach and versatile tool for noncatalytic carbonÀheteroatom bond formation is briefly presented, including mecha-nistic and kinetic aspects, as well as some structuralc onsiderations,t hat is, the influenceo ft he thiol and olefin structures, which should be well-thought-out before applying such chemistry.T his discussiona lso coversh ow an initiator works and its effect on the reactionr ate. Moreover,t he utilization of thiol-ene reactions for the synthesis of terpenebased valuable platform chemicals, monomers, and polymers, includingr ecent examples that demonstrate its broad utility,a re highlighted.[a] Dr.M.F irdaus Scheme11. Terpene-basedp olythioethers thatwere prepared by thiol-ene photopolymerization. [100] Scheme12. Preparation of cross-linkedthin films that were derived from limonene and their possible addition type. [101] Asian

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“…[35] As the molecular diversity of the samples is easily reached through different combinations of reactants, series of vinylic monomers have been synthesized by different groups. [36][37][38][39][40][41][42] Especially the Passerini three-component reaction (P-3CR) using (meth)acrylic acid provided (meth)acrylate monomers in a versatile fashion. The P-3CR was discovered in 1921 by Mario Passerini and involves the reaction of a carboxylic acid, a ketone or aldehyde, and an isocyanide to form 𝛼-acyloxycarboxamides.…”

Section: Introductionmentioning

confidence: 99%

Microgel Preparation by Miniemulsion Polymerization of Passerini Multicomponent Reaction Derived Acrylate Monomers

Windbiel

Llevot

2021

Macro Chemistry & Physics

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Three acrylate monomers featuring different side-groups are synthesized in yields up to 94% in a one-pot procedure using the versatile Passerini-three-component reaction. The procedure for their miniemulsion polymerization into polymeric particles with tunable sizes is established. Ethylene glycol dimethacrylate is introduced as comonomer to induce crosslinking and enable the production of microgels. Besides the shelf life of the miniemulsions, the dependence of the particle size on the concentration of the surfactant (sodium dodecyl sulfate) and the crosslinker, as well as the sonication amplitude and time, is investigated. The particle size of the collapsed microgels range from 21 to 91 nm. The swelling of the microgels in organic solvents is studied.

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Synthesis of polyacrylates from limonene by catalytic oxidation and multi-component reaction

Cited by 12 publications

References 22 publications

Direct Catalytic Route to Biomass-Derived 2,5-Furandicarboxylic Acid and Its Use as Monomer in a Multicomponent Polymerization

Direct Catalytic Route to Biomass-Derived 2,5-Furandicarboxylic Acid and Its Use as Monomer in a Multicomponent Polymerization

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Microgel Preparation by Miniemulsion Polymerization of Passerini Multicomponent Reaction Derived Acrylate Monomers

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