- Molecular properties of 2-pyrone-4,6-dicarboxylic acid (PDC) as a stable metabolic intermediate of lignin isolated by fractional precipitation with na+ Ion
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A chemically stable metabolic intermediate of lignin, 2-pyrone-4,6- dicarboxylic acid (PDC), was isolated, and the molecular properties were comprehensively investigated by using thermal analysis, optical spectroscopy, potentiometric titration, and X-ray crystallography. UV absorption spectra of PDC did not show any solvent effects, whereas the fluorescence spectra displayed distinct solvatochromism. Despite the fairly good planarity of the PDC geometry, dual fluorescence was observed in some small donor number solvents. The emission behaviors are thought to be due to the significant twist between the pyrone ring and carboxylate substituents, found in the X-ray crystal structures of the Na+ complex. The crystal structure also showed the intermolecular, centrosymmetric short hydrogen bonding of the carboxylate moieties with an O...H...O distance of 0.2452 nm, which made it possible to assign the pKa values to the molecular structure. PDC was thermally stable and could be sublimed even at atmospheric pressure, offering the preparation possibility of ultra-thin films by vapor-deposition techniques. The fact that the chemically and thermally stable compound possessing many attractive functions, such as unique emission, facile sublimation, and strong acidity, resulting in exceptionally short intermolecular contacts, can be obtained from biomass on a large quantity will lead to establishment of carbon neutral system in future industry.
- Michinobu, Tsuyoshi,Bito, Masami,Yamada, Yoshiko,Katayama, Yoshihiro,Noguchi, Keiichi,Masai, Eiji,Nakamura, Masaya,Ohara, Seiji,Shigehara, Kiyotaka
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- LARGE-SCALE PURIFICATION OF 2-PYRONE-4,6-DICARBOXYLIC ACID
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To provide an industrial purification method of PDC obtained by fermentative production. A method of purifying 2-pyrone-4,6-dicarboxylic acid which comprises including a salt of monovalent to tetravalent cations in a fermentation liquid containing microbially-produced 2-pyrone-4,6-dicarboxylic acid; and a method of purifying 2-pyrone-4,6-dicarboxylic acid which method comprises extracting 2-pyrone-4,6-dicarboxylic acid from a fermentation liquid containing microbially-produced 2-pyrone-4,6-dicarboxylic acid without forming 2-pyrone-4,6-dicarboxylate.
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Page/Page column 4
(2012/01/13)
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- Organogels of lignin-derived stable metabolic intermediate, 2-pyrone-4,6-dicarboxylic acid (PDC), Bearing cholesteryl groups
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The organogelation behavior of a lignin-derived stable metabolic intermediate bearing two cholesteryl groups was examined for the first time, and it was found that the carbamate spacers possessing a hydrogen-bonding ability are essential for gelation of aliphatic or aromatic organic solvents.
- Michinobu, Tsuyoshi,Hiraki, Kenta,Fujii, Nozomu,Shikinaka, Kazuhiro,Katayama, Yoshihiro,Masai, Eiji,Nakamura, Masaya,Otsuka, Yuichiro,Ohara, Seiji,Shigehara, Kiyotaka
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supporting information; experimental part
p. 400 - 401
(2010/07/10)
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- A novel biomass-based polymer prepared from lignin-derived stable metabolic intermediate by copper(I)-catalyzed azide-alkyne click reaction
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The CuI-catalyzed, but ligand-free azide-alkyne cycloaddition reaction was applied to the polymerization of the newly synthesized diethynyl-functionalized 2-pyrone monomer originally isolated from lignin via metabolic pathway. The polymerization was monitored by GPC and IR spectra and the resulting high molecular weight polymer was unambiguously characterized by 1H NMR, thermal analysis, and optical absorption and emission spectra. Copyright
- Michinobu, Tsuyoshi,Inazawa, Yasunori,Hiraki, Kenta,Katayama, Yoshihiro,Masai, Eiji,Nakamura, Masaya,Ohara, Seiji,Shigehara, Kiyotaka
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p. 154 - 155
(2008/09/18)
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