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Synthesis and property of alkyl dioxyethyl α-D-xyloside.
Journal of Molecular Liquids ( IF 6 ) Pub Date : 2020-07-08 , DOI: 10.1016/j.molliq.2020.113770
Xiubing Wu 1 , Na Kuang 1 , Langqiu Chen 1 , Yulin Fan 1 , Fang Fu 1 , Jiping Li 1 , Jing Zhang 1
Affiliation  

Due to the inherent defects of the long alkyl chain in the related hydrophilicity and water solubility, alkyl α-D-xylosides (7) had hardly the practical application as sugar-based surfactants and should be reconstructed to obtain alkyl dioxyethyl α-D-xylosides (5) with dioxyethylene fragment (−(OCH2CH2)2-)) as the hydrophilic spacer to increase the related TPSA value. With D-xylose as the raw material, 1,2-cis alkyl dioxyethyl α-D-xylosides (5a-5f, n = 6–12) were stereoselectively synthesized. Their physicochemical properties including water solubility, surface tension, foamability, emulsification, thermotropic liquid crystal, and hygroscopicity had been investigated. Their water solubility was found to decrease gradually whereas their calculated HLB numbers were 14.72 → 11.67 (n = 6 → 12) with increasing alkyl chain length (n). Dodecyl dioxyethyl α-D-xyloside (5f) had not water solubility because the HLB number was low. Furthermore, their CMC values decreased with increasing the alkyl chain length, and the CMC value of decyl dioxyethyl α-D-xyloside (5e) was as low as 9.21 × 10−5 mol·L−1. Octyl dioxyethyl α-D-xyloside (5c) had the lowest surface tension (27.25 mN·m−1) at the CMC. Both of nonyl and decyl dioxyethyl α-D-xylosides (5d & 5e) possessed good foaming power and foam stability. Decyl dioxyethyl α-D-xyloside (5e) had the strongest emulsifying property either in the toluene/water system or in the octane/water system. Nonyl dioxyethyl α-D-xylosides (5d) had the most stylish SA texture. Hexyl dioxyethyl α-D-xyloside (5a) possessed the strongest hygroscopicity. Therefore, the alkyl dioxyethyl α-D-xylosides as a class of novel sugar-based surfactants will be widely considered as promising candidates for various practical applications.



中文翻译:

烷基二氧乙基α-D-木糖苷的合成及性质。

由于长烷基链在亲水性和水溶性方面的固有缺陷,烷基α - D-木糖苷( 7 )作为糖基表面活性剂几乎没有实际应用,需要进行改造以获得烷基二氧乙基α - D-木糖苷( 5 )以二氧乙烯片段(-(OCH 2 CH 2 ) 2 -))作为亲水间隔基以增加相关的TPSA值。以D-木糖为原料,立体选择性合成了1,2-顺式烷基二氧乙基α - D-木糖苷(5a-5f ,n=6-12)。研究了它们的物理化学性质,包括水溶性、表面张力、发泡性、乳化性、热致液晶性和吸湿性。随着烷基链长度 (n)的增加,它们的水溶性逐渐降低,而计算出的HLB值为 14.72 → 11.67 (n = 6 → 12)。十二烷基二氧乙基α - D-木糖苷( 5f )由于HLB值低而不具有水溶性。此外,它们的CMC值随着烷基链长度的增加而降低,其中癸基二氧乙基α - D-木糖苷( 5e )的CMC值低至9.21×10 -5  mol·L -1。辛基二氧乙基α - D-木糖苷( 5c )在CMC处具有最低的表面张力(27.25 mN·m -1 ) 。壬基和癸基二氧乙基α - D-木糖苷( 5d5e )均具有良好的发泡力和泡沫稳定性。癸基二氧乙基α - D-木糖苷( 5e )无论在甲苯/水体系还是在辛烷/水体系中均具有最强的乳化性能。壬基二氧乙基α - D-木糖苷(5d)具有最时尚的SA质地。己基二氧乙基α - D-木糖苷( 5a )具有最强的吸湿性。因此,烷基二氧乙基α - D-木糖苷作为一类新型糖基表面活性剂将被广泛认为是各种实际应用的有希望的候选者。

更新日期:2020-07-17
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