Resin Swelling in Mixed Solvents Analysed using Hansen Solubility Parameter Space

被引:32
|
作者
Ran, Yanrui [1 ]
Byrne, Fergal [1 ]
Ingram, Ian D., V [1 ]
North, Michael [1 ]
机构
[1] Univ York, Green Chem Ctr Excellence, Dept Chem, Heslington YO10 5DD, England
关键词
binary mixture; green chemistry; Hansen solubility parameters; resin-swelling; solid-phase peptide synthesis; solvents; PHASE PEPTIDE-SYNTHESIS; DIHYDROLEVOGLUCOSENONE CYRENE; N-BUTYLPYRROLIDINONE; PROPYLENE CARBONATE; ALTERNATIVE SOLVENT; ALDOL REACTIONS; DMF; PERSPECTIVE; SCAFFOLDS; CHEMISTRY;
D O I
10.1002/chem.201900228
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The swelling of resins (Merrifield and HypoGel 200) in mixtures of two solvents was generally found not to vary linearly with the relative amount of each solvent in the mixture. Hansen solubility parameter (HSP) space could be used to define high, medium and low swelling regions for each resin. The variation of resin swelling with binary solvent composition could then be explained based on the HSP parameters of the two solvents and the way in which the line connecting the points corresponding to the two pure solvents bisected the swelling region for the resin. The applica- bility of the methodology was demonstrated by showing that an appropriate mixture of two green solvents was more effective for solid- phase peptide synthesis on Merrifield resin than use of either individual solvent and could completely replace the use of traditional polar aprotic and chlorinated solvents for this application. It was also shown that the high resin swelling area of Merrifield resin can be used to predict mixtures of green solvents that will dissolve linear, unfunctionalised polystyrene.
引用
收藏
页码:4951 / 4964
页数:14
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