Synthesis of sulfated alginate from its tributylammonium salt: Comparing the sulfating agents H2SO4-DCC and SO3·py

Abstract

Direct comparison of the sulfating agents H2SO4-DCC and SO3·py for the synthesis of sulfated alginate (S-Alg) as well as detailed characterisation of the products that form is lacking. This study involving three researchers used the tributylammonium salt of alginate (T-Alg) as a common substrate for the sulfation reactions. It was found that the use of H2SO4-DCC resulted in poor control of the degree of sulfation (DS) and that the S-Alg polymers contained nitrogen (determined by elemental analysis) as a result of formation of an unwanted N-acylurea adduct. Additionally, a large reduction in chain length was confirmed. In contrast, the use of SO3·py gave reasonable control over DS, resulted in high yields, showed no contamination and no clear change in chain length. Detailed characterisation of such S-Alg polymers by 1H NMR, 13C NMR and 1H,13C-HSQC NMR confirmed sulfation at C2 and C3 with a preference for C2.