Nanoencapsulation of Binary Sugar Alcohols at Neutral pH Conditions

Mo, Songping; Shan, Shaofei; Li, He; Jia, Lisi; Chen, Ying

doi:10.1007/s10876-022-02223-8

Cited by 7 publications

(2 citation statements)

References 34 publications

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“…Additionally, we shed light on the thermal instability of sugar alcohols with melting points exceeding 240 °C, underscoring the inherent challenges associated with utilizing organic compounds as PCMs when facing this temperature window. Since high thermal stability is one of the most important physical properties for a material considered as a PCM, decomposition at temperatures close to the melting point is an undesirable characteristic for further application, despite efforts in the development of encapsulation techniques for natural sugar alcohols ,, to overcome thermal stability issues.…”

Section: Resultsmentioning

confidence: 99%

Indium-Mediated Acyloxyallylation-Based Synthesis of Galacto-Configured Higher-Carbon Sugar Alcohols as Potential Phase Change Materials

Biedermann,

Schnizer,

Lager

et al. 2024

J. Org. Chem.

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Sugar alcohols fulfilling specific structural requirements are a substance class with great potential as organic phase change materials (PCMs). Within this work, we demonstrate the indium-mediated acyloxyallylation (IMA) as a useful strategy for the synthesis of higher-carbon sugar alcohols of the galacto-family featuring all hydroxyl groups in a 1,3-anti-relationship with three major synthetic achievements: first, the dihydroxylation of the IMA-derived allylic sugar derivates was systematically studied in terms of diastereoselectivity, revealing a high degree of substrate control toward anti-addition. Second, we demonstrated the use of a "double Mitsunobu" reaction, inverting the stereochemistry of terminal diols. Third, the IMA toolbox was expanded to accomplish the synthesis of derivatives with up to 10 carbon atoms from particularly unreactive aldoses. Thermal investigations of all synthesized sugar alcohols, including examples with exclusive 1,3-anti-and suboptimal 1,3-syn-relationships as well as even and odd numbers of carbon atoms, were performed. We observed clear trends in melting points and thermal storage densities and discovered limitations of organic substances in this class with melting points above 240 °C as PCMs in terms of thermal stability. With our study, we provide insights into the dependence of thermal properties on structural features, thus contributing to further understanding of organic PCMs for thermal energy storage applications.

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Section: Resultsmentioning

confidence: 99%

Indium-Mediated Acyloxyallylation-Based Synthesis of Galacto-Configured Higher-Carbon Sugar Alcohols as Potential Phase Change Materials

Biedermann,

Schnizer,

Lager

et al. 2024

J. Org. Chem.

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“…Therefore, it can be potentially used as a medium-temperature PCM for solar heat storage. One drawback, however, is the leakage problem, which might cause serious damage through device failure and contamination in realistic applications [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Spent Yeast-Derived 3D Porous Carbon Skeleton as Low-Cost D-Mannitol Supporting Material for Medium Temperature Thermal Energy Storage

Zhu

et al. 2023

Materials

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Shape-stable phase change materials (ss-PCMs) are extensively applied in renewable energy storage. The core for realizing high latent heat and good thermal stability of ss-PCMs is the designation of suitable supporting skeletons that can effectively preserve the PCMs from leaking out. In this study, ss-PCMs impregnated by D-mannitol were prepared using a waste yeast-derived carbon (YC) as the support material. YC possesses a large surface area (669.90 m2/g), which can provide sufficient phase transition space and nucleation sites for D-mannitol. The results indicated that a reduced supercooling of 44.76 °C for YC/D-mannitol ss-PCMs can be realized. The ss-PCMs also exhibited good cycling stability, with latent heat loss rates of 4.00% and 2.15% after 200 thermal cycles. We further demonstrate that YC provides restricted space for mannitol to inhibit the supercooling mechanism. The YC/D-mannitol ss-PCMs exhibited great promise for solar heat storage and industrial waste heat recovery in the medium temperature domain.

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The synthesis of higher-carbon sugar alcohols via indium-mediated acyloxyallylation as potential phase change materials

Draskovits,

Biedermann,

Mihovilovic

et al. 2023

Monatsh Chem

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In recent years, sugar alcohols have gained significant attention as organic phase change materials (PCMs) for thermal energy storage due to their comparably high thermal storage densities up to 350 J/g. In a computational study, outstandingly high values of up to ~ 450500 J/g have been postulated for specific higher-carbon sugar alcohols. These optimized structures feature an even number of carbon atoms in the backbone and a stereochemical configuration in which all hydroxyl groups are in an 1,3-anti-relationship, as found in the natural hexitol d-mannitol. However, these manno-configured higher-carbon sugar alcohols have not been experimentally investigated as PCMs yet and described synthetic routes are elaborate multiple steps syntheses. Therefore, we aimed to synthesize sugar alcohols of the manno-series with a concise synthetic protocol based on the indium-mediated acyloxyallylation (IMA) of aldoses. En route the C2-epimers were easily accessible, namely gluco-configured sugar alcohols, bearing one set of hydroxyl groups in a suboptimal 1,3-syn-realtionship. The synthesized compounds were found to possess thermal properties consistent with the predicted values, and the “perfect” higher-carbon sugar alcohol with eight carbon atoms was found to have indeed an outstanding high latent heat of fusion of ~ 380 J/g with a melting point of 260 °C. Graphical abstract

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Nanoencapsulation of Binary Sugar Alcohols at Neutral pH Conditions

Cited by 7 publications

References 34 publications

Indium-Mediated Acyloxyallylation-Based Synthesis of Galacto-Configured Higher-Carbon Sugar Alcohols as Potential Phase Change Materials

Indium-Mediated Acyloxyallylation-Based Synthesis of Galacto-Configured Higher-Carbon Sugar Alcohols as Potential Phase Change Materials

Spent Yeast-Derived 3D Porous Carbon Skeleton as Low-Cost D-Mannitol Supporting Material for Medium Temperature Thermal Energy Storage

The synthesis of higher-carbon sugar alcohols via indium-mediated acyloxyallylation as potential phase change materials

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