Microbial itaconic acid bioproduction towards sustainable development: Insights, challenges, and prospects

Diankristanti, Priskila Adjani; Ng, I-Son

doi:10.1016/j.biortech.2023.129280

Cited by 10 publications

(8 citation statements)

References 101 publications

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“…With maleic anhydride, the product was isolated together with a small side product resulting from a decarboxylation [10d] during the methyl esterification. Itaconic acid is produced on a large commercial scale by fermentation [17] and appears on the list of platform molecules from the U.S. Department of Energy [18] . Thus, the coupling into ketone 11 presents an interesting carbon‐carbon bond formation between two widely available bio‐derived substrates.…”

Section: Resultsmentioning

confidence: 99%

Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins

Nielsen,

El‐Chami,

de Lichtenberg

et al. 2024

Eur J Org Chem

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Furfural is produced on a large commercial scale from lignocellulose and can be used for the preparation of several industrial chemicals with four to five carbon atoms. Further functionalization of furfural by C–H activation, however, is less widely developed. In the present work, tetrabutylammonium decatungstate is investigated as an inexpensive photocatalyst for activating the aldehyde C–H bond and mediate a coupling between furfural and electron‐deficient olefins. The results show that furfural can be successfully added to benzylidene malononitriles, acrylates, itaconic anhydride, maleic anhydride, 2‐vinylpyridine and phenyl vinyl sulfone to generate the corresponding furanyl ketones in moderate‐to‐good yields. The electronic properties of the electron‐deficient olefins are instrumental for achieving a favorable reaction with furfural. The findings show how photocatalysis can be used to form new carbon‐carbon bonds from a platform molecule, which in this way can be converted into a number of more advanced structures.

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Section: Resultsmentioning

confidence: 99%

Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins

Nielsen,

El‐Chami,

de Lichtenberg

et al. 2024

Eur J Org Chem

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“…This transformation constitutes an interesting carbonÀ carbon bond formation between two compounds, which both appear on the list of platform molecules from the U.S. Department of Energy. [16] Itaconic acid is produced on large commercial scale by fermentation [17] and has previously been subjected to a photocatalytic coupling to isopropanol and cyclohexanol with benzophenone as the photosensitizer, [18] but no reaction with glycerol has been described before.…”

Section: Resultsmentioning

confidence: 99%

Photocatalyzed Carbon−Carbon Bond Formation Between Glycerol and Electron‐Deficient Olefins

El‐Chami,

Madsen

2023

ChemCatChem

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Glycerol is produced in large quantities as a co‐product in the manufacturing of biodiesel and has received relatively little attention as a substrate for carbon‐carbon bond‐forming reactions. In this work, the photocatalyzed reaction between glycerol and electron‐deficient olefins is investigated to regioselectively insert an alkyl group at C2 in the triol. The results show that the transformation is highly dependent on the nature of the photocatalyst and the olefin. In the presence of an iridium catalyst and quinuclidine, glycerol can be coupled at C2 with sterically unhindered acrylates. In the presence of tetrabutylammonium decatungstate, glycerol can be reacted with fumaronitrile, N‐methyl maleimide, methyl acrylate and itaconic anhydride where the latter two substrates require the additional presence of potassium persulfate as an oxidant. These findings give rise to several new carbon‐carbon bond‐forming reactions with glycerol that allow the triol to be converted into more elaborate structures.

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“…Several fundamental properties, such as cross-link performance, amorphous nature or minimal crystallization, low glass transition temperature, and highefficiency reinforced by fillers are crucial factors in determining whether a polymer can be used as an elastomer. To achieve the desired characteristics, we employed four biobased monomers in large-scale production�dimethyl furandicarboxylate, dimethyl succinate, 25 dimethyl itaconate 26 and 1,5-pentandiol 27 �to construct a hybrid biobased copolyester elastomer called poly(1,5-pentylene succinate-co-itaconate-co-furanoate) (PPeSIFs) esters via simple transesterification and polycondensation methods. These monomers were combined not only to reduce the macromolecule chain geometrical regularity so as to suppress crystallization but also to establish a linear macromolecular structure to maintain the required elasticity and processability.…”

Section: ■ Introductionmentioning

confidence: 99%

Design and Characterization of High Gas Barrier and Fully Biobased Poly(1,5-pentylene succinate-co-itaconate-co-furanoate) Elastomers

Lin,

Li,

et al. 2024

ACS Sustainable Chem. Eng.

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Biomass feedstock is an accessible alternative to finite fossil chemical resources for fabricating durable and high-performance polymers. In this study, fully biobased poly(1,5-pentylene succinate-co-itaconate-co-furanoate) (PPeSIFs) copolyesters were synthesized by using transesterification and melt polycondensation methods from dimethyl furandicarboxylate, dimethyl succinate, dimethyl itaconate, and 1,5pentanediol. Dimethyl itaconate was incorporated to provide the cross-linkable reaction sites. Four kinds of monomers were employed to regulate the glass transition temperature and suppress crystallization. Silica/PPeSIF nanocomposites exhibited good mechanical properties, such as an ultimate tensile strength of 17.2 MPa and an elongation at break of 253%. This elastomer displayed outstanding gas barrier properties comparable to those of butyl rubber, with an O 2 permeability 13 times lower than that of natural rubber. Positron annihilation lifetime spectroscopy tests demonstrated that furan moieties significantly reduced the free volume of PPeSIFs. This work provides a promising route for preparing a biobased elastomer with intrinsic high gas barrier properties.

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Microbial itaconic acid bioproduction towards sustainable development: Insights, challenges, and prospects

Cited by 10 publications

References 101 publications

Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins

Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins

Photocatalyzed Carbon−Carbon Bond Formation Between Glycerol and Electron‐Deficient Olefins

Design and Characterization of High Gas Barrier and Fully Biobased Poly(1,5-pentylene succinate-co-itaconate-co-furanoate) Elastomers

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