Enantiomer separation on novel cellulose derivatives bearing regioselective phenylcarbamate groups. Issue 2 (19th November 2020)

• Record Type: Journal Article
• Authors: Tang, Shouwan; Wang, Fang; Yan, Zhenzhong; Huang, Ling
• Is Part Of: Journal of separation science. Volume 44:Issue 2(2021)
• Page Start: 489
• Page End: 496
• Publication Date: 2020-11-19
• Subjects: cellulose derivatives -- chiral separation -- chiral stationary phases -- high‐performance liquid chromatography -- polysaccharide; Separation (Technology) -- Periodicals; Chromatographic analysis -- Periodicals; 543.089
• DOI: 10.1002/jssc.202000912
• Languages: English
• ISSNs: 1615-9306

Abstract

Abstract: Four novel regioselectively carbamoylated cellulose derivatives with two types of substituents, one being a 3‐chloro‐4‐methylphenylcarbamate group and the other being a phenylcarbamate, a 3, 5‐dichlorophenylcarbamate or a 4‐methylphenylcarbamate group, at the 2‐, 3‐positions and 6‐position were synthesized and utilized as chiral stationary phases in high‐performance liquid chromatography. The obtained derivatives exhibited characteristic chiral recognition abilities which were significantly affected by the nature and arrangement of the groups at the 2‐, 3‐positions and 6‐position. Compared with cellulose tris(3‐chloro‐4‐methylphenylcarbamate) and Chiralcel OD columns, several racemates were better resolved on these new phases. With all six racemates resolved on cellulose 2, 3‐bis(4‐methylphenylcarbamate)‐6‐(3‐chloro‐4‐methylphenylcarbamate), it appears to be a potential useful chiral stationary phase in the future. Also, the influence of mobile phase on chiral recognition was investigated. Better resolutions were generally obtained with decreased amount of 2‐propanol with a mixture of hexane/2‐propanol as the mobile phase. Moreover, when ethanol was used instead of 2‐propanol as the mobile phase modifier, poorer enantioseparations were often achieved.