title: Study on the thermal degradation of 3-MCPD esters in model systems simulating deodorization of vegetable oils.
abstract: The establishment of effective strategies for the mitigation of 3-MCPD esters in refined vegetable oils is restricted by limited knowledge of their mechanisms of formation and decomposition. In order to gain better understanding on the thermal stability of these compounds, a model system for mimicking oil refining conditions was developed. Pure 3-MCPD esters (3-MCPD dipalmitate and 3-MCPD dilaurate) were subjected to thermal treatment (180-260°C) and the degradation products where monitored over time (0-24h). After 24h of treatment, both 3-MCPD esters showed a significant degradation (ranging from 30% to 70%), correlating with the temperature applied. The degradation pathway, similar for both compounds, was found to involve isomerisation (very rapid, equilibrium was reached within 2h at 260°C), dechlorination and deacylation reactions. The higher relative abundance of non-chlorinated compounds, namely acylglycerols, in the first stages of the treatment suggested that dechlorination is preferred over deacylation with the conditions applied in this study.
authors.affiliation: Unilever R&D Vlaardingen, Vlaardingen, The Netherlands; Technical University of Berlin, Berlin, Germany.
authors.forename: Alessia
authors.initials: A
authors.lastname: Ermacora
authors.affiliation: Unilever R&D Vlaardingen, Vlaardingen, The Netherlands. Electronic address: karel.hrncirik@unilever.com.
authors.forename: Karel
authors.initials: K
authors.lastname: Hrncirik
mesh_terms: D004952:Esters / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry; D005990:Glycerol / Q000031:analogs & derivatives* / Q000737:chemistry; D006358:Hot Temperature; D007700:Kinetics; D009812:Odorants / Q000032:analysis*; D000073878:Palm Oil; D010938:Plant Oils / Q000737:chemistry*; D000517:alpha-Chlorohydrin
chemical_list: D004952:Esters; D005227:Fatty Acids; D010938:Plant Oils; D000073878:Palm Oil; D000517:alpha-Chlorohydrin; D005990:Glycerol
keywords: 1,2-dilauroyl-3-chloropropane; 1,2-dipalmitoyl-3-chloropropane; 2-MCPD ester; 3-MCPD; 3-MCPD ester; Degradation; LL-3-MCPD; Model system; Oil refining; P-MAG; PP-3-MCPD; PP-DAG; PPP-TAG; Thermal stability; glycerol dipalmitate; glycerol monopalmitate; glycerol tripalmitate