Study On Synthesis And Chromatographic Separation Of Monochlorotriazinyl-β-Cyclodextrins

Monochlorotriazinyl-β-cyclodextrin (MCT-β-CD) is one of the first reactive cyclodextrin derivative manufactured on an industrial scale. It has a monochlorotriazinyl group as a reactive anchor well known from many reactive dyes, this derivative is able to form stable covalent bonds with nucleophilic groups by a condensation reaction, and therefore it can transfer the cyclodextrin properties to the treated materials permanently. In this paper, MCT-β-CDs were synthesized by cyanuric chloride andβ-cyclodextrin in alkali solution. The reaction synthesis process was investigated. The range of average subsituted degrees was from 0.849 to 3.803 providing quality criterions for industrial application. Otherwise, prepared chromatography separation method was used to get different substituted degrees monochlorotriazinyl-β-cyclodextrin.The influences of different conditions such as the reaction volume, the reaction time and the molar ratio of raw material on the average substituted degrees and content of MCT-β-CD were studied in this paper. The results showed that: 1) the substituted degrees decreased with increasing the reaction volume. Meanwhile the yield of monochlorotriazinyl-β-cyclodextrin increased firstly and then reduced, it was about 80mL when the yield arrived at the largest value. The contents of different substituted degrees MCT-β-CD of three productions were: the mono-substituted was the most, the di-substituted was the next and tri-substituted was the least. 2) the most compatible reaction time was 48h, as the average substituted degree was highest around this time. The yield would go up with time increased same as the di-substituted, but the mono- turned to be declined. 3) With the mass of cyanuric chloride increased, the average substituted degrees also increased. When the molar ratio of cyanuric chloride toβ-cyclodextrin was above 9:1, the yield of production became to slow down. The contents of compounds with different substituted degree distributed symmetrically and altered with the addition of cyanuric chloride. 4) Orthogonal condition experiments demonstrated that the quality of the production was influenced mostly by the reaction volume and molar ratio of raw material.The effective developed solution was chosen out through thin layer chromatography. It was 1-propanol- 2-propanol–water -ammonia (3:3:3:1, V/V). Two monochlorotriazinyl-β-cyclodextrins with different substituted degrees and positions which were derived by silica column chromatography were proved to be mono-6-O- monochlorotriazinyl-β-cyclodextrin, di-6-O-monochlorotriazinyl-β-cyclodextrin by means of UV, IR, DSC, ESI-MS, 1H NMR, 13C NMR.