13039-42-4Relevant articles and documents
Self-organizing properties of monosubstituted sucrose fatty acid esters: The effects of chain length and unsaturation
Molinier, Valerie,Kouwer, Paul J. J.,Fitremann, Juliette,Bouchu, Alain,Mackenzie, Grahame,Queneau, Yves,Goodby, John W.
, p. 3547 - 3557 (2006)
Three families of mono-substituted sucrose fatty acid esters were prepared by enzymatic and classical synthetic procedures, and their self-assembly and self-organizational properties were investigated by thermal polarised light microscopy, differential scanning calorimetry and X-ray diffraction. The properties were evaluated as a function of the fatty acid chain length. For the lower homologues of the series columnar liquid-crystalline stacking structures were found, whereas for the higher homologues, lamellar phases predominated. A model for the columnar stacking arrangement, consisting of a unique arrangement of the molecules which could lead to the creation of multiple internal ion channels between the hydrophobic interior and the hydrophilic exterior of the columns, is suggested.
Efficient Solvent-Free Synthesis of Sucrose Esters via Sand-Milling Pretreatment on Solid–Liquid Mixtures
Chen, Jiazhi,Li, Yuan,Chen, Xiaotian,Mai, Yuliang,Gao, Minjie,Zhang, Junjie,Wang, Xi
, (2019)
A general and efficient method, involving sand-milling pretreatment and base-catalyzed transesterification of sucrose and fatty acid methyl ester (FAME), was presented for the solvent-free synthesis of sucrose esters. A metastable homogeneous paste with a solid particle size of 13 μm (D50) was obtained by milling at 1000 rpm for 1 h. This reaction mixture generated a total SE yield of 88.2% with a methyl stearate (MS) conversion of 91.4% using K2CO3 as a catalyst at 135?°C for 3 h at a stirring rate of 500 rpm, while those without milling (D50, 153 μm) yielded a total sucrose fatty acid esters (SE) of 49.3% with a MS conversion of 83.1% under the same reaction conditions. The reaction kinetics revealed that the reaction mixture with milling pretreatment displays a shorter induction time and a faster reaction rate for the formation of SE. The promotion of the solvent-free synthesis of SE in the current study could be attributed to the reduction of solid particle sizes and the increased compatibility of solid–liquid phases. We believe that this strategy could be used as a general way for strengthening other heterogeneous reactions in the organic synthesis.
Regioselective formation of 6-O-acylsucroses and 6,3′-di-O-acylsucroses via the stannylene acetal method
Wang, Qinghui,Zhang, Shufen,Yang, Jinzong
, p. 2657 - 2663 (2008/09/17)
Regioselective formation of 6-O-acylsucroses and 6,3′-di-O-acylsucroses in one pot with good yields was achieved for the first time by a typical acylation method of sucrose via its dibutylstannylene acetal. Pure monoesters at OH-6 and diesters at OH-6,3′ obtained by these procedures were readily isolated by simple column chromatography, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. Explanations for the regioselectivities observed during this stannylene acetal-mediated reaction were also proposed based on the structures of the stannylene acetal in solution and the intramolecular migration of stannylenes.
