Preparation of bio-based styrene alternatives and their free radical polymerization

Schijndel, Jack van; Molendijk, Dennis; Beurden, Koen van; Canalle, Luiz Alberto; Noël, Timothy; Meuldijk, J.

doi:10.1016/j.eurpolymj.2020.109534

Cited by 37 publications

(46 citation statements)

References 36 publications

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“…There are numerous examples of these intermediate structures which are produced on a larger scale. Some of these are furan-based monomers, biobased styrene monomers, bifunctional monomers for biobased chemically recyclable polyesters and acrylates (11)(12)(13)(14). Molecules synthesized by the Knoevenagel reaction directly used in products are also widespread.…”

Section: Introductionmentioning

confidence: 99%

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

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110

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The formation of carbon-carbon bonds is a quest that has required a lot of research throughout the last 125 years of history of chemistry. The creation of these bonds is key to producing a wide variety of advanced products with great societal importance. In the past, the Knoevenagel reaction entailed a big part of these reactions. All the Knoevenagel reactions are performed with nitrogen-based catalysts, categorized as tertiary amines, secondary amines, primary amines, and ammonium salts. These catalysts operate through different reaction paths, with very deviant intermediates concerning each category. Subsequently, these intermediates create new research opportunities considering their catalytic activity. Some remarks are made in the context of green chemistry, with quantitative analysis using e-factor calculations. In this perspective, the importance of Knoevenagel chemistry exemplified, which is repeatedly overlooked throughout history.

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Section: Introductionmentioning

confidence: 99%

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

Self Cite

110

View full text Add to dashboard Cite

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“…Although this is an advantage, one must ensure that no other compound present in the wastewater co‐precipitates. Finally, solvent‐free Knoevenagel‐Doebner reaction can be performed using acetic acid/sodium acetate or ammonium bicarbonate [39,42,43] . Viscosity can be an important drawback for the scale‐up of these procedures.…”

Section: Discussionmentioning

confidence: 99%

“…Finally, solvent-free Knoevenagel-Doebner reaction can be performed using acetic acid/sodium acetate or ammonium bicarbonate. [39,42,43] Viscosity can be an important drawback for the scale-up of these procedures. After completion, in the case of acetic acid/sodium acetate, the mixture needs to be diluted in a mixture of ethanol and acetic acid, before washing with cold ethanol and recrystallization.…”

Section: Discussionmentioning

confidence: 99%

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Accessing p‐Hydroxycinnamic Acids: Chemical Synthesis, Biomass Recovery, or Engineered Microbial Production?

et al. 2020

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p-Hydroxycinnamic acids (i. e., p-coumaric, ferulic, sinapic, and caffeic acids) are phenolic compounds involved in the biosynthesis pathway of lignin. These naturally occurring molecules not only exhibit numerous attractive properties, such as antioxidant, anti-UV, and anticancer activities, but they also have been used as building blocks for the synthesis of tailored monomers and functional additives for the food/feed, cosmetic, and plastics sectors. Despite their numerous high value-added applications, the sourcing of p-hydroxycinnamic acids is not ensured at the industrial scale except for ferulic acid, and their production cost remains too high for commodity applications. These compounds can be either chemically synthesized or extracted from lignocellulosic biomass, and recently their production through bioconversion emerged. Herein the different strategies described in the literature to produce these valuable molecules are discussed.

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“…Sinapic, ferulic and p -coumaric acid were prepared in moderate to high yields from 3,5-dimethoxy-4-hydroxy-, 3-methoxy-4-hydroxy- and 4-hydroxy-benzaldehydes, respectively; however, with higher temperatures (i.e., 140 °C), second decarboxylation usually occurred [ 61 ]. Recently, van Schijndel and coauthors published a similar procedure at 90 °C that led to aforementioned HCAs in excellent yields ( Figure 3 ) [ 62 ]. Furthermore, to limit the decarboxylation of the resulting HCAs, another approach employing microwave irradiation was presented in the literature.…”

Section: Synthesis and Properties Of Natural And Synthetic Hydroxymentioning

confidence: 99%

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

et al. 2020

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This review presents the main properties of hydroxycinnamic acid (HCA) derivatives and their potential application as agents for the prevention and treatment of neurodegenerative diseases. It is partially focused on the successful use of these compounds as inhibitors of amyloidogenic transformation of proteins. Firstly, the prerequisites for the emergence of interest in HCA derivatives, including natural compounds, are described. A separate section is devoted to synthesis and properties of HCA derivatives. Then, the results of molecular modeling of HCA derivatives with prion protein as well as with α-synuclein fibrils are summarized, followed by detailed analysis of the experiments on the effect of natural and synthetic HCA derivatives, as well as structurally similar phenylacetic and benzoic acid derivatives, on the pathological transformation of prion protein and α-synuclein. The ability of HCA derivatives to prevent amyloid transformation of some amyloidogenic proteins, and their presence not only in food products but also as natural metabolites in human blood and tissues, makes them promising for the prevention and treatment of neurodegenerative diseases of amyloid nature.

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Preparation of bio-based styrene alternatives and their free radical polymerization

Cited by 37 publications

References 36 publications

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Accessing p‐Hydroxycinnamic Acids: Chemical Synthesis, Biomass Recovery, or Engineered Microbial Production?

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

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