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Trimethylsilylation of Polygalacturonic Acid
Author(s) -
Würfel Hendryk,
Kayser Marvin,
Heinze Thomas
Publication year - 2019
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201900002
Subject(s) - chemistry , moiety , reagent , silylation , trimethylsilyl chloride , polymer chemistry , polymer , imidazole , chloride , formamide , organic chemistry , trimethylsilyl , carboxylic acid , catalysis
The trimethylsilylation of polygalacturonic acid is investigated in formamide as reaction medium at elevated temperature employing 1,1,1,3,3,3‐hexamethyldisilazan (HMDS) or trimethylsilyl chloride (TMSCl) in combination with imidazole. The products obtained are characterized by size exclusion chromatography, NMR‐, and IR spectroscopy. Regarding the degree of substitution (DS), HMDS is a more reactive silylation reagent compared to TMSCl/imidazole. Products with DS values of 0.6 are obtained with TMSCl while HMDS yields products with DS of up to 1.8. Nevertheless, both reagents lead to the formation of side products. In the case of HMDS, formation of amid moiety occurs, which renders the carboxylic acid at the polymer backbone inaccessible for further transformations. Cross‐linking of polymer chains occurs applying TMSCl, which influences the molecular masses of the products obtained.