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An eco-compatible pathway to new hydrotropes from tetraols
Green Chemistry ( IF 9.8 ) Pub Date : 2018-01-09 00:00:00 , DOI: 10.1039/c7gc02990j
Aurélien Herbinski 1, 2, 3, 4, 5 , Estelle Métay 1, 2, 3, 4, 5 , Eric Da Silva 1, 2, 3, 4, 5 , Estelle Illous 3, 6, 7, 8, 9 , Jean-Marie Aubry 3, 6, 7, 8, 9 , Marc Lemaire 1, 2, 3, 4, 5
Affiliation  

New hydrotropes such as mono-ethers of tetraols were synthesized using an eco-friendly methodology. The mono-ethers, with chain lengths between 5 and 12 carbons, were obtained via a two-step synthesis: acetalisation and hydrogenolysis. Acetalisation, with the corresponding aldehyde, gave rise to 69% to 91% isolated yields of erythritol acetals, and 63% to 79% yields of pentaerythritol acetals. Hydrogenolysis of these acetals was performed resulting in good yields of erythritol (72% to 86%) and pentaerythritol (78% to 83%) derivatives. The physico-chemical analysis of these ethers was realized using DSC and TGA analysis to determine the melting and boiling point. The solubility of the ethers decreased from the alkyl chain of above 6 carbons, with higher hydrophilicity for an erythritol polar head. Salt-tolerance of the polyol ethers showed insensitivity of C5-O- and C6-O-erythritol toward NaCl. C6-O-erythritol and C5-O-pentaerythritol demonstrated better solubilizing properties of Dispers Red 13 compared to conventional hydrotropes. Aqueous self-aggregation was observed at a lower concentration of Cx-O-pentaerythritol compared to Cx-O-erythritol.

中文翻译:

从四元醇到新的水溶助剂的生态兼容途径

使用生态友好的方法合成了新的水溶助长剂,例如四醇的单醚。通过以下方法获得链长在5到12个碳之间的单醚两步合成:乙缩醛化和氢解。与相应的醛缩醛缩醛化,季戊四醇缩醛的分离产率为69%至91%,季戊四醇缩醛的分离产率为63%至79%。对这些乙缩醛进行氢解,得到了赤藓糖醇(72%至86%)和季戊四醇(78%至83%)衍生物的良好收率。使用DSC和TGA分析来确定熔点和沸点,从而对这些醚进行了理化分析。醚的溶解度从高于6个碳的烷基链开始降低,对赤藓糖醇极性头具有更高的亲水性。所述多元醇醚的耐盐性表明的C不敏感性5 - ö -和C 6 - ø -赤朝向NaCl中。C 6- ø -赤和C 5 - ø -季戊四醇证明更好增DISPERS红13的特性相比于常规水溶助长剂。中C的浓度较低,观察到水自聚集X - ø -季戊四醇与C X - Ò -赤。
更新日期:2018-03-20
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