Synthesis of alkylated potato starch derivatives and their potential in the aqueous solubilization of benzo[a]pyrene

► Modified potato starch was synthesized by alkylation. ► The chemical structural characteristics were investigated by NMR and FTIR. ► The ether modified starches present a higher aqueous solubility. ► The alkyl succinic anhydrides starches present high capacity to desorb benzo[a]pyrene. For the dev...

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Bibliographic Details
Published in:Carbohydrate polymers 2013-03, Vol.93 (1), p.184-190
Main Authors: Rosu, Ana-Maria, Rafin, Catherine, Surpateanu, Gheorghe, Brabie, Gheorghe, Miron, Doru Neculai, Veignie, Etienne
Format: Article
Language:English
Subjects:
Alkanesulfonates - chemistry
Alkylating Agents - chemistry
Alkylation
alkylation agents
Amphiphile
Applied sciences
Benzo(a)pyrene - chemistry
Benzo[a]pyrene
biobased products
Esterification
Ether - chemistry
Etherification
Exact sciences and technology
Fourier transform infrared spectroscopy
Life Sciences
Magnetic Resonance Spectroscopy
modified starch
Molecular Structure
Natural polymers
nuclear magnetic resonance spectroscopy
Physicochemistry of polymers
pollutants
Potato starch
Solanum tuberosum - chemistry
Solubility
solubilization
Spectroscopy, Fourier Transform Infrared
Starch - analogs & derivatives
Starch - chemistry
Starch and polysaccharides
Surface-Active Agents - chemistry
surfactants
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Summary:► Modified potato starch was synthesized by alkylation. ► The chemical structural characteristics were investigated by NMR and FTIR. ► The ether modified starches present a higher aqueous solubility. ► The alkyl succinic anhydrides starches present high capacity to desorb benzo[a]pyrene. For the development of renewable bioproducts able to solubilize organic persistent pollutant such as benzo[a]pyrene (BaP), modified potato starch was synthesized by alkylation. The addition of alkyl chains was performed with three different alkylation agents: epoxyalkane, alkenyl succinic anhydride and 1,4-butane sultone. Twelve alkylated starches were obtained with different molar substitutions (MS) and various alkyl chain lengths (to three carbons up to sixteen). The chemical structural characteristics were investigated by methods of 1H NMR and FTIR. In comparison with the native starch, the ether modified starches showed in general an enhancement of their aqueous solubility whereas the ester modified starches stimulated the BaP aqueous solubilization. Indeed, the compounds P6 and P12, which increased 40-fold the BaP aqueous concentration, present high surfactant properties.
ISSN:0144-8617
1879-1344
DOI:10.1016/j.carbpol.2012.06.062