title: Synthesis of modified potato starches for aqueous solubilization of benzo[a]pyrene.
abstract: For soil rehabilitation, the surfactant-enhanced remediation has emerged as a promising technology. For this purpose, starch derivatives were difunctionalized by 1,4-butane sultone (BS) and 2-octen-1-ylsuccinic anhydride (OSA). Eight distinct products were obtained under different synthesis conditions. The chemical structural characteristics were investigated by (1)H NMR spectroscopy. The compounds were evaluated for their apparent aqueous solubility and their ability to increase the solubility of a hydrophobic pollutant such as benzo[a]pyrene (BaP), used as a polycyclic aromatic hydrocarbon model. In comparison with native starch, the best obtained compound increased starch apparent aqueous solubility by a factor of 10 (up to 3.50g/L) and also stimulated 77-fold BaP aqueous solubilization (up to 232.97μg/L) underlining its very high surfactant property. In this study, the right balance between hydrophobic character (octenyl succinate group (OS) grafted) of starch derivatives and starch apparent aqueous solubility (BS grafted) was highlighted.
authors.affiliation: ULCO, Université du Littoral Côte d'Opale, Unité de Chimie Environnementale et Interactions sur le Vivant, Dunkerque 59140, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Delsarte
authors.affiliation: ULCO, Université du Littoral Côte d'Opale, Unité de Chimie Environnementale et Interactions sur le Vivant, Dunkerque 59140, France.
authors.forename: Pierre-Edouard
authors.initials: PE
authors.lastname: Danjou
authors.affiliation: ULCO, Université du Littoral Côte d'Opale, Unité de Chimie Environnementale et Interactions sur le Vivant, Dunkerque 59140, France.
authors.forename: Etienne
authors.initials: E
authors.lastname: Veignie
authors.affiliation: ULCO, Université du Littoral Côte d'Opale, Unité de Chimie Environnementale et Interactions sur le Vivant, Dunkerque 59140, France. Electronic address: rafin@univ-littoral.fr.
authors.forename: Catherine
authors.initials: C
authors.lastname: Rafin
mesh_terms: D000476:Alkanesulfonates / Q000138:chemical synthesis* / Q000737:chemistry; D001564:Benzo(a)pyrene / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D007202:Indicators and Reagents; D066244:Proton Magnetic Resonance Spectroscopy; D011198:Solanum tuberosum / Q000737:chemistry*; D012995:Solubility; D013213:Starch / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013387:Succinic Anhydrides / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000620795:2-octen-1-ylsuccinic anhydride; D000476:Alkanesulfonates; D007202:Indicators and Reagents; D013387:Succinic Anhydrides; D013501:Surface-Active Agents; C000335:butanesultone; D001564:Benzo(a)pyrene; D013213:Starch
keywords: 1,4-Butane sultone (PubChem CID: 15411); 2-Octen-1-ylsuccinic anhydride (PuBChem CID: 5362689); Alkylation; Benzo[a]pyrene; Benzo[a]pyrene (PubChem CID: 2336); Deuterium oxide (PubChem CID: 24602); Dichloromethane (PubChem CID: 6344); Dimethyl sulfoxide (PubChem CID: 679); Potato starch; Potato starch (PubChem SID: 135306210); Sodium hydroxide (PubChem CID: 14798); Surfactant