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Solvent‐free synthesis of 6‐deoxy‐6‐(ω‐aminoalkyl)amino cellulose
Author(s) -
Heinze Thomas,
Pfeifer Annett,
Koschella Andreas,
Schaller Jens,
Meister Frank
Publication year - 2016
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.43987
Subject(s) - diamine , chemistry , amine gas treating , solvent , cellulose , reagent , ethylene diamine , polymer chemistry , organic chemistry , tosyl , acetone , ethylene , imine , tris , nuclear chemistry , catalysis , biochemistry
Cellulose p ‐toluenesulfonic acid esters (TosCell) with degree of substitution (DS Tos ) between 0.8 and 1.4 were converted with ethylene diamine or tris (2‐aminoethyl)amine. In contrast to procedures published, the conversion was carried out without any solvent, i.e., the reagent (amines) was used as reaction medium yielding readily soluble products. Moreover, the absence of an additional solvent makes the recycling of both not‐consumed amine and precipitant easy. Recycling experiments proofed the possibility of reusing the isolated ethylene diamine. The DS of 6‐deoxy‐6‐(ω‐aminoalkyl)amino groups is between 0.71 and 0.93, which is in accordance with the functionalization pattern of tosyl cellulose and the ability of amines to displace primary tosylate moieties only. Attention must be paid to the precipitant used for the workup procedure; 13 C NMR measurements revealed a formation of imine structures in case of precipitation with acetone. Precipitation in 2‐propanol did not lead to any side product. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133 , 43987.