Dehydration of erythritol in high-temperature carbonated water

Published on Oct 1, 2019in Molecular Catalysis5.062
· DOI :10.1016/J.MCAT.2019.110519
Kenkichi Taniguchi2
Estimated H-index: 2
(Iwate University),
Hidetaka Nanao18
Estimated H-index: 18
(Iwate University)
+ 2 AuthorsMasayuki Shirai29
Estimated H-index: 29
(AIST: National Institute of Advanced Industrial Science and Technology)
Sources
Abstract
Abstract Intramolecular dehydration of erythritol to 1,4-anhydroerythritol proceeded in liquid water at 573 K. The initial formation rate and final yield of 1,4-anhydroerythritol were 0.50 mmol h−1 and 71%, respectively. Addition of carbon dioxide up to the pressure of 17.7 and 24.8 MPa to water solvent at 573 K, the initial product formation rates dramatically increased to 1.45 and 2.10 mmol h−1, respectively; however, the final yields were almost the same as 73 and 71%, respectively. These results showed that the protons derived from carbonic acid catalyzed the intramolecular dehydration and the concentration of proton increased with an increase in the carbon dioxide pressure introduced.
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The intramolecular dehydration of biomass-derived sugar alcohols D-sorbitol, D-mannitol, galactitol, xylitol, ribitol, L-arabitol, erythritol, L-threitol, and DL-threitol was investigated in high-temperature water at 523–573 K without the addition of any acid catalysts. D-Sorbitol and D-mannitol were dehydrated into isosorbide and isomannide, respectively, as dianhydrohexitol products. Galactitol was dehydrated into anhydrogalactitols; however, the anhydrogalactitols could not be dehydrated into...
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The hydroxyl group of enantioenriched benzyl, propargyl, allyl, and alkyl alcohols has been intramolecularly displaced by uncharged O-, N-, and S-centered nucleophiles to yield enantioenriched tetrahydrofuran, pyrrolidine, and tetrahydrothiophene derivatives with phosphinic acid catalysis. The five-membered heterocyclic products are generated in good to excellent yields, with high degree of chirality transfer, and water as the only side-product. Racemization experiments show that phosphinic acid...
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Heterogeneous ReOx–Pd/CeO2 catalyst showed excellent performance for simultaneous hydrodeoxygenation of vicinal OH groups. High yield (>99 %), turnover frequency (300 h−1), and turnover number (10 000) are achieved in the reaction of 1,4-anhydroerythritol to tetrahydrofuran. This catalyst can be applied to sugar alcohols, and mono-alcohols and diols are obtained in high yields (≥85 %) from substrates with even and odd numbers of OH groups, respectively. The high catalytic performance of ReOx–Pd/...
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