Recycling preparation of high-purity tagatose from galactose using one-pot boronate affinity adsorbent-based adsorption-Assisted isomerization and simultaneous purification

Wang, Zihao; Wang, Mingming; Lyu, Xiaomei; Wang, Caiyun; Tong, Yanjun; Xiao, Hua; Yang, Ruijin

doi:10.1016/j.cej.2022.137089

Cited by 9 publications

(19 citation statements)

References 37 publications

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“…Noteworthily, the in situ removal of Tag suppressed not only the destruction processes, but also 3epimerization of Tag into Sorb: the yield of Sorb decreased from 14% without adsorption to 5% in the presence of the phenylboronate-functionalized polymer. 71 5.2. Organic Solvents.…”

Section: Catalysis By Soluble Basesmentioning

confidence: 99%

“…Tag was recognized as Generally Recognized as Safe (GRAS) by U.S. Food and Drug Administration. The 2016 global artificial sweetener market estimated to be USD 3.2 billion highlighting a high demand for the economic production of rare sugars, such as Tag. , Base-catalyzed isomerization of Gal to Tag via 1,2-enediolate also results in a minor production of a rare aldose d -talose (Tal) (Figure ). In the presence of bases, Tag undergoes 3-epimerization to produce d -sorbose (Sorb).…”

Section: Base-catalyzed Interconversions Of Saccharidesmentioning

confidence: 99%

“…Selectivity–conversion plots for formation of Tag (left) and Sorb (right) via isomerization of Gal catalyzed by phosphate buffer at pH 7.5 at 80–110 °C, Mg–Al hydrotalcite at 80–100 °C, Mg/SiO 2 at 110 °C, arginine at at 120 °C, phosphate buffer at pH 7.0 at 140 °C, NaH 2 PO 4 +NaOH at pH 12.0, MgO at 90–110 °C, and calcined Mg–Al hydrotalcite at 110 °C …”

Section: Base-catalyzed Interconversions Of Saccharidesmentioning

confidence: 99%

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Toward Understanding Base-Catalyzed Isomerization of Saccharides

Delidovich

2023

ACS Catal.

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This Perspective addresses recent advances in isomerization of aldoses into ketoses catalyzed by bases. In recent years, catalytic activity of a number of bases was reported, but the structure–performance correlations are typically missing or remain poorly understood. In this Perspective, the reaction mechanism and kinetics of the base-catalyzed isomerization are discussed. An overview of products obtained via base-catalyzed transformations of d-glucose (Glc), d-lactose (Lac), d-galactose (Gal), and aldopentoses d-ribose (Rib), d-arabinose (Ara), d-xylose (Xyl), and d-lyxose (Lyx) is provided. Side reactions that occur under base conditions are summarized. Catalysis by soluble metal hydroxides and general bases is considered. Moreover, structure–selectivity relationships observed for soluble bases as well as methods for stabilization of ketoses via complexation are discussed. Influences of organic (co-)solvents on reaction kinetics and acceleration of the reaction rate in aqueous phase in the presence of soluble salts–also referred to as salt effect–are addressed. Next, solid bases applied as catalysts for isomerization are considered with a focus on contributions of homogeneous and heterogeneous catalysis into the isomerization processes. The applicability of a filtration test and a contact test as tools to estimate impact of leached species onto catalysis is critically discussed.

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Section: Catalysis By Soluble Basesmentioning

confidence: 99%

Section: Base-catalyzed Interconversions Of Saccharidesmentioning

confidence: 99%

Section: Base-catalyzed Interconversions Of Saccharidesmentioning

confidence: 99%

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Toward Understanding Base-Catalyzed Isomerization of Saccharides

Delidovich

2023

ACS Catal.

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“…Consequently, these could increase the adsorption and regeneration capacity of adsorbents. 9,10 For example, Liu 11 et al prepared a hydrophilic boronic acid-affinity imprinted hydrogel sorbent that could capture and separate LTL with high selectivity. Further, the adsorption capacity was only reduced by 6.24% after 5 cycles.…”

Section: Introductionmentioning

confidence: 99%

“…Consequently, these could increase the adsorption and regeneration capacity of adsorbents. 9,10 For example, Liu 11 et al…”

Section: Introductionmentioning

confidence: 99%

A boronate-affinity magnetic molecularly imprinted polymer for luteolin recognition

et al. 2023

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Production of Tagatose from Galactose with CaO at Room Temperature

Zhao,

Cruz,

Shi

et al. 2024

ChemCatChem

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This study investigates the efficacy of Sn‐β zeolite, triethylamine, and CaO in the isomerization of galactose to tagatose. At temperatures over 80 °C, all three reagents exhibited low tagatose yield (< 20%). Notably, at 100 °C and a CaO/galactose molar ratio of 1/5, a galactose conversion of 64% was achieved with a tagatose selectivity of 17%. The tagatose selectivity decreased over time at this temperature. However, at room temperature, a tagatose selectivity of 56% and 73% with a CaO to galactose molar ratio of 1/1 and 2/1 respectively was obtained with a 100% galactose conversion after 40 min of reaction. The galactose conversion had a linear relationship with the molar ratio of CaO/galactose at room temperature. This indicates that CaO functions as a stoichiometric reagent rather than a catalyst. A yellowish gel‐like complex formed when the CaO/galactose molar ratios exceeded 1/2. It is noteworthy that these phenomena were not observed with MgO. In addition, low isomerization conversion from glucose to fructose was observed with CaO.

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Recycling preparation of high-purity tagatose from galactose using one-pot boronate affinity adsorbent-based adsorption-Assisted isomerization and simultaneous purification

Cited by 9 publications

References 37 publications

Toward Understanding Base-Catalyzed Isomerization of Saccharides

Toward Understanding Base-Catalyzed Isomerization of Saccharides

A boronate-affinity magnetic molecularly imprinted polymer for luteolin recognition

Production of Tagatose from Galactose with CaO at Room Temperature

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