A coating from nature

Hermens, Johannes G. H.; Freese, Thomas; Berg, Keimpe J. van den; Gemert, Rogier van; Feringa, Ben L.

doi:10.1126/sciadv.abe0026

Cited by 60 publications

(93 citation statements)

References 52 publications

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“…Scalable setups have been designed with energy-efficient lamps (LED). [16] Safer solvents and auxiliaries In the synthesist owards maleic anhydride and acrylic acid, methanol, acetonitrile, water and THF are used. These solvents are ranked high in terms of environmentally safe solvents.…”

Section: Atom Economymentioning

confidence: 99%

Highly Efficient Biobased Synthesis of Acrylic Acid

2021

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Petrochemical based polymers,p aints and coatings are cornerstones of modern industry but our future sustainable society demands greener processes and renewable feedstock materials.Achallenge is to access platform monomers from biomass resources while integrating the principles of green chemistry in their chemical synthesis.W ep resent as ynthesis route starting from biomass-derived furfural towards the commonly used monomers maleic anhydride and acrylic acid, implementing environmentally benign photooxygenation, aerobic oxidation and ethenolysis reactions.Maleic anhydride and acrylic acid, transformed into sodium acrylate,w ere isolated in yields of 85 %( 2s teps) and 81 %( 4s teps), respectively.With minimal waste and high atom efficiency,this biobased route provides av iable alternative to access key monomers.

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Section: Atom Economymentioning

confidence: 99%

Highly Efficient Biobased Synthesis of Acrylic Acid

2021

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“…Typically, photooxidation reactions, especially when performed on a larger scale, are limited by physical factors, such as light penetration and mass transfer of oxygen into the solution [22] . Previously, we have shown the upscaling of the photooxidation of furfural to hydroxybutenolide by developing a photo flow reactor for continuous production and a rotary photoreactor for larger batch processes [16] . The rotary photoreactor, modelled after Poliakoff and George, [23] is a versatile setup that allows for fast conversion.…”

Section: Resultsmentioning

confidence: 99%

“…Optimal light penetration is achieved due to the thin film that is created by rotation of the reaction flask containing a small volume with a high concentration of furfural. Concurrently, having an oxygen atmosphere applied simply with an O 2 filled balloon results in excellent mass transfer into the solution which allows a fast conversion of 10 mmol (1 g) furfural in 20 min [16, 23] . The photooxidation reaction was carried out under optimized conditions in methanol (MeOH) using methylene blue as photosensitizer [16] .…”

Section: Resultsmentioning

confidence: 99%

“…Focusing on the monomer formation, we recently showed the synthesis and application of alkoxybutenolides as acrylate alternatives in the formation of biobased polymers and coatings [16] . As part of our program on clean photocatalytic oxidation, the platform chemical furfural is photooxygenated using singlet oxygen to yield hydroxybutenolide quantitatively (Schemes 2 and 3).…”

Section: Introductionmentioning

confidence: 99%

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Highly Efficient Biobased Synthesis of Acrylic Acid

2021

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Petrochemical based polymers, paints and coatings are cornerstones of modern industry but our future sustainable society demands greener processes and renewable feedstock materials. A challenge is to access platform monomers from biomass resources while integrating the principles of green chemistry in their chemical synthesis. We present a synthesis route starting from biomass‐derived furfural towards the commonly used monomers maleic anhydride and acrylic acid, implementing environmentally benign photooxygenation, aerobic oxidation and ethenolysis reactions. Maleic anhydride and acrylic acid, transformed into sodium acrylate, were isolated in yields of 85 % (2 steps) and 81 % (4 steps), respectively. With minimal waste and high atom efficiency, this biobased route provides a viable alternative to access key monomers.

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“… 11 One potent strategy that potentially tackles the above-mentioned points consists of divergent generation of biobased polymers harboring difference in structure, but with chemical and physical properties similar to currently industrially implemented synthetic polymers. 9 , 12 …”

Section: Introductionmentioning

confidence: 99%

Pinene-Based Oxidative Synthetic Toolbox for Scalable Polyester Synthesis

Stamm

Öhlin

Mosbech

et al. 2021

JACS Au

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Generation of renewable polymers is a long-standing goal toward reaching a more sustainable society, but building blocks in biomass can be incompatible with desired polymerization type, hampering the full implementation potential of biomaterials. Herein, we show how conceptually simple oxidative transformations can be used to unlock the inherent reactivity of terpene synthons in generating polyesters by two different mechanisms starting from the same α-pinene substrate. In the first pathway, α-pinene was oxidized into the bicyclic verbanone-based lactone and subsequently polymerized into star-shaped polymers via ring-opening polymerization, resulting in a biobased semicrystalline polyester with tunable glass transition and melting temperatures. In a second pathway, polyesters were synthesized via polycondensation, utilizing the diol 1-(1′-hydroxyethyl)-3-(2′-hydroxy-ethyl)-2,2-dimethylcyclobutane (HHDC) synthesized by oxidative cleavage of the double bond of α-pinene, together with unsaturated biobased diesters such as dimethyl maleate (DMM) and dimethyl itaconate (DMI). The resulting families of terpene-based polyesters were thereafter successfully cross-linked by either transetherification, utilizing the terminal hydroxyl groups of the synthesized verbanone-based materials, or by UV irradiation, utilizing the unsaturation provided by the DMM or DMI moieties within the HHDC-based copolymers. This work highlights the potential to apply an oxidative toolbox to valorize inert terpene metabolites enabling generation of biosourced polyesters and coatings thereof by complementary mechanisms.

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A coating from nature

Cited by 60 publications

References 52 publications

Highly Efficient Biobased Synthesis of Acrylic Acid

Highly Efficient Biobased Synthesis of Acrylic Acid

Highly Efficient Biobased Synthesis of Acrylic Acid

Pinene-Based Oxidative Synthetic Toolbox for Scalable Polyester Synthesis

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