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Design of a green chemoenzymatic cascade for scalable synthesis of bio-based styrene alternatives

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Design of a green chemoenzymatic cascade for scalable synthesis of bio-based styrene alternatives. / Petermeier, Philipp; Bittner, Jan Philipp; Müller, Simon et al.

In: Green Chemistry, Vol. 24, No. 18, 09.2022, p. 6889-6899.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Vancouver

Petermeier P, Bittner JP, Müller S, Byström E, Kara S. Design of a green chemoenzymatic cascade for scalable synthesis of bio-based styrene alternatives. Green Chemistry. 2022 Sep;24(18):6889-6899. Epub 2022 Aug. doi: 10.1039/d2gc01629j

Author

Petermeier, Philipp ; Bittner, Jan Philipp ; Müller, Simon et al. / Design of a green chemoenzymatic cascade for scalable synthesis of bio-based styrene alternatives. In: Green Chemistry. 2022 ; Vol. 24, No. 18. pp. 6889-6899.

Bibtex

@article{1d8bf55add8041b5a2acc19e8f2ad986,

title = "Design of a green chemoenzymatic cascade for scalable synthesis of bio-based styrene alternatives",

abstract = "As renewable lignin building blocks, hydroxystyrenes are particularly appealing as either a replacement or addition to styrene-based polymer chemistry. These monomers are obtained by decarboxylation of phenolic acids and often subjected to chemical modifications of their phenolic hydroxy groups to improve polymerization behaviour. Despite efforts, a simple, scalable, and purely (chemo)catalytic synthesis of acetylated hydroxystyrenes remains elusive. We thus propose a custom-made chemoenzymatic route that utilizes a phenolic acid decarboxylase (PAD). Our process development strategy encompasses a computational solvent assessment informing about solubilities and viable reactor operation modes, experimental solvent screening, cascade engineering, heterogenization of biocatalyst, tailoring of acetylation conditions, and reaction upscale in a rotating bed reactor. By this means, we established a clean one-pot two-step process that uses the renewable solvent CPME, bio-based phenolic acid educts and reusable immobilised PAD. The overall chemoenzymatic reaction cascade was demonstrated on a 1 L scale to yield 18.3 g 4-acetoxy-3-methoxystyrene in 96% isolated yield.",

keywords = "CATECHOL, CHEMISTRY, CINNAMIC-ACIDS, DECARBOXYLATION, LIQUID-LIQUID EQUILIBRIA, PLUS WATER, POLYMERIZATION, POLYMERS, SOLUBILITY, SOLVENTS",

author = "Philipp Petermeier and Bittner, {Jan Philipp} and Simon M{\"u}ller and Emil Bystr{\"o}m and Selin Kara",

year = "2022",

month = sep,

doi = "10.1039/d2gc01629j",

language = "English",

volume = "24",

pages = "6889--6899",

journal = "Green Chemistry",

issn = "1463-9262",

publisher = "Royal Society of Chemistry",

number = "18",

}

RIS

TY - JOUR

T1 - Design of a green chemoenzymatic cascade for scalable synthesis of bio-based styrene alternatives

AU - Petermeier, Philipp

AU - Bittner, Jan Philipp

AU - Müller, Simon

AU - Byström, Emil

AU - Kara, Selin

PY - 2022/9

Y1 - 2022/9

N2 - As renewable lignin building blocks, hydroxystyrenes are particularly appealing as either a replacement or addition to styrene-based polymer chemistry. These monomers are obtained by decarboxylation of phenolic acids and often subjected to chemical modifications of their phenolic hydroxy groups to improve polymerization behaviour. Despite efforts, a simple, scalable, and purely (chemo)catalytic synthesis of acetylated hydroxystyrenes remains elusive. We thus propose a custom-made chemoenzymatic route that utilizes a phenolic acid decarboxylase (PAD). Our process development strategy encompasses a computational solvent assessment informing about solubilities and viable reactor operation modes, experimental solvent screening, cascade engineering, heterogenization of biocatalyst, tailoring of acetylation conditions, and reaction upscale in a rotating bed reactor. By this means, we established a clean one-pot two-step process that uses the renewable solvent CPME, bio-based phenolic acid educts and reusable immobilised PAD. The overall chemoenzymatic reaction cascade was demonstrated on a 1 L scale to yield 18.3 g 4-acetoxy-3-methoxystyrene in 96% isolated yield.

AB - As renewable lignin building blocks, hydroxystyrenes are particularly appealing as either a replacement or addition to styrene-based polymer chemistry. These monomers are obtained by decarboxylation of phenolic acids and often subjected to chemical modifications of their phenolic hydroxy groups to improve polymerization behaviour. Despite efforts, a simple, scalable, and purely (chemo)catalytic synthesis of acetylated hydroxystyrenes remains elusive. We thus propose a custom-made chemoenzymatic route that utilizes a phenolic acid decarboxylase (PAD). Our process development strategy encompasses a computational solvent assessment informing about solubilities and viable reactor operation modes, experimental solvent screening, cascade engineering, heterogenization of biocatalyst, tailoring of acetylation conditions, and reaction upscale in a rotating bed reactor. By this means, we established a clean one-pot two-step process that uses the renewable solvent CPME, bio-based phenolic acid educts and reusable immobilised PAD. The overall chemoenzymatic reaction cascade was demonstrated on a 1 L scale to yield 18.3 g 4-acetoxy-3-methoxystyrene in 96% isolated yield.

KW - CATECHOL

KW - CHEMISTRY

KW - CINNAMIC-ACIDS

KW - DECARBOXYLATION

KW - LIQUID-LIQUID EQUILIBRIA

KW - PLUS WATER

KW - POLYMERIZATION

KW - POLYMERS

KW - SOLUBILITY

KW - SOLVENTS

UR - http://www.scopus.com/inward/record.url?scp=85135712834&partnerID=8YFLogxK

U2 - 10.1039/d2gc01629j

DO - 10.1039/d2gc01629j

M3 - Journal article

VL - 24

SP - 6889

EP - 6899

JO - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

IS - 18

ER -