Hou-Chin stream, Love river, and Chien-Chen river, the three main rivers in Kaohsiung city, flow through the populous residential and industrial areas. A large portion of sewage from domestic and industrial sources are discharged into these rivers, then the Love river and Chien-Chen river pour into the harbor area. In order to understand the pollution of alkylphenol polyethoxylates in these areas, water and sediment samples in Hou-Chin stream, Love river, Chien-Chen river and harbor area in Kaohsiung city were collected and the contents of alkylphenol and corresponding polyethoxylates were analyzed in this study. LC/MS/MS was used as the analytical instrument which is relatively time-saving in comparison with other instruments. It is also more convenient due to the facts that no derivation or colorization are needed in sample pretreatment. The detection limit can reach to 0.03 ng/ml and recovery can be around 83.6~91.6%. It can analyze alkylphenols combinded with long ethoxylate chain with improved sensitivity and selectivity. In the four sampling areas, the concentration of NPs in water were between 7.4~241.8ng/ml, and OPs were between 0.66~64.2ng/ml. The most contaminated water samples were found at Chih-Ping Bridge on the mainstream of Love river and Pau-Chu-Kou Dam Station and Min-Tsu Bridge on the tributary of Love river where the concentrations of NPs were greater than 200ng/ml, OPs were greater than 30ng/ml. We found that the main pollution sources were from Lung-Hsin Bridge, Tzu-Yu Bridge, Lung -Hua Bridge, and Pau-Chu-Kou Dam Station. The pollution sources of the Chien-Chen river were mainly from Chung-An Bridge and Chen-Chuan Bridge. Concentration of NPs in upper sediments were between 633.1~2113.8ng/g, OPs were between 50.3~287.9ng/g. The highest concentration of NPs was at Ho-Ti Bridge on the mainstream of Love river, and the lowest concentration of NPs was at Chung-An Bridge on Chien-Chen river. The highest concentration of OPs was at Chen-Chuan Bridge in Chien-Chen river, and the lowest concentration of OPs was Min-Tsu Bridge on the tributary of Love river. The concentration of NPs in deeper sediments were between 523.9~1919.5ng/g, OPs were between 39.9~322.0ng/g. The highest concentration of NPs was at Chung-Hua Bridge on the tributary of Lover river, and the lowest concentration of NPs was at Chung-An Bridge on Chien-Chen river. The highest concentration of OPs was at Chi-Chin Fishing Port, and the lowest concentration of OPs was at Min-Tsu Bridge on the tributary of Love river. The salinity of water samples and the total organic carbon in sediment sample will influence the distribution coefficient of alkylphenol polyethoxylates with different length of ethoxylate chains, their distribution coefficients were between 0.48~2.67. In comparison with foreign studies, the concentrations of alkylphenol polyethoxylates of water and sediments amples in this study were between the highest and lowest values reported. However, the observed concentrations of alkylphenols in these study areas were higher then other rivers in Taiwan. These values were higher than the Probable No Effect Concentrations ( PNEC) of NP risk assessed by European Union. It can be concluded that the pollution of alkylphenol polyethoxylates of water and sediment is getting more serious in Hou-Chin stream, Love river, Chien-Chen river and harbor area in Kaohsiung city.

A LC-MS/MS method for the analysis of alkylphenol polyethoxylates in environmental waters was developed in this study. Preatment procedures including liquid-liquid extraction and solid phase extraction were compared, it¡¦s concluded that solid phase extraction is the more suitable way due to higher recovery and better stability for the analytical results. The recovery of nonylphenol polyethoxylate and octylphenol polyethoxylate were 62.3-110.7 % and 64.9-112.0 %, limit of detection were 17.60-174.9 ng/L and 7.40-53.56 ng/L. Enviromental water samples were collected from eight sampling sites along Love River in Kaohsiung City to investigate the contents of alkylphenol polyethoxylates. The highest concentration of total alkylphenol polyethoxylates was observed at Ming-Cheng Bridge which located at the upstream of Love River. For all of the analyzed compounds, the concentration of octylphenol tetraethoxylate (40.46 £gg/L) was the highest in all of the sampling sites. It¡¦s also noticed the concentration of octylphenol polyethoxylate (20.11 £gg/L) was higher than that of nonylphenol polyehtoxylate (128.04 £gg/L).

In April and June 2012, environmental water samples were collected from fourteen sampling sites in Hengchun peninsula to investigate the contents of alkylphenol polyethoxylates. A solid phase extraction combined with LC-MS/MS method for the analysis of alkylphenol polyethoxylates in environmental waters was developed in this study. The mobile phase used methanol gradient elution with deionized water. The recovery of nonylphenol polyethoxylate and octylphenol polyethoxylate were 68~94 % and 65~93 %, limit of detection were 1.89~54.20 ng/L and 0.44~39.31 ng/L, limit of quantitative were 6.29~181 ng/L and 1.48~131 ng/L. The SsuChung river contents of NPEO and OPEO were 15.64~36.29 £gg/L and 3.14~7.37 £gg/L. The Paoli river contents of NPEO and OPEO were 16.65~76.41 £gg/L and 5.66~18.80 £gg/L. The Hou Bay contents of NPEO and OPEO were 34.79~66.72 £gg/L and 7.77~19.03 £gg/L. The Shihniou river contents of NPEO and OPEO were 26.67 £gg/L and 6.68 £gg/L. The Wanli Tong, Baisha, Houbi Lake, South Bay, Caesar and Siangjiao Bay contents of NPEO and OPEO were 14.17~48.82 £gg/L and 3.88~14.79 £gg/L. The dry season concentration contents of alkylphenol polyethoxylates were high than the wet season. The concentration of nonylphenol polyethoxylate was higher than that of octylphenol polyehtoxylate.

La thèse s'intéresse à la présence et au devenir de sept alkylphénols et du bisphénol A (BPA) dans un bassin versant dont une partie est très urbanisée et l'autre fait l'objet d'une exploitation agricole intense : le bassin de la Seine, dans sa zone centrale (région Île-de-France). Elle est organisée autour de quatre approches. Dans une première approche les sources urbaines ont été caractérisées. Pour cela, les rejets des 5 plus grandes stations d'épuration (STEP) de la région Île-de-France (IDF), les rejets urbains de temps de pluie (RUTP), les eaux de ruissellement urbain en réseaux séparatifs et les retombées atmosphériques ont été analysés. Cette étude a révélé que le BPA était majoritairement présent dans les sources de temps de pluie (RUTP + eau de ruissellement) tandis que l'acide nonylphénoxy acétique (NP1EC), un précurseur du 4-nonylphénol (4-NP), est dominant dans les rejets de STEP. Le 4-NP a, lui, été retrouvé dans toutes les sources étudiées à des concentrations avoisinant la centaine de nanogrammes par litre (ng.l-1), témoignant de sa forte dissémination dans l'environnement urbain. Dans un second temps, l'imprégnation du milieu a été considérée au niveau des eaux de surface et des sols, à deux échelles d'observation. La première échelle est le bassin de l'Orgeval, caractéristique d'un petit bassin amont, tandis que la seconde échelle intègre l'ensemble de la région IDF et l'agglomération parisienne. Ces deux échelles ont permis de mettre en évidence une dissémination importante du 4-NP à l'ensemble des matrices naturelles du bassin de la Seine. A l'échelle de l'IDF, l'influence de l'agglomération parisienne a été démontrée sur les concentrations de NP1EC et BPA dans la Seine. Puis, la biodégradabilité des composés nonylphénoliques dans la Seine a été déterminée par une approche innovante. Les constantes de biodégradabilité ont été déterminées directement dans la Seine à l'aide du modèle ProSe (développé par le Centre de Géosciences, Ecole des Mines ParisTech) et de campagnes de prélèvement spécifiques sur le fleuve (suivi d'une masse d'eau). Les constantes de biodégradation simulées dans la Seine présentent de très fortes variabilités en fonction des conditions hydrauliques et climatiques. Après un épisode de bloom algal, les constantes de biodégradation des composés nonylphénoliques se sont avérées être 10 à 35 fois supérieures à celles retrouvées en conditions classiquement rencontrées en Seine. Enfin, les flux d'alkylphénols et de BPA exportés par la Seine ont été comparés aux flux émis par les sources urbaines au niveau annuel. A l'échelle de l'année (2010), les flux de 4-NP et de BPA émis par l'ensemble des sources urbaines considérées ne sont pas prédominants devant les flux exportés par la Seine à l'aval de l'agglomération parisienne. Ce résultat vient une fois de plus confirmer la dissémination importante du 4-NP et du BPA dans toute la région IDF en raison de leur forte utilisation depuis les années 1960. Il soulève également plusieurs questions concernant les sources actuelles des flux retrouvés et la contamination des zones amont du bassin de la Seine. Cette thèse a été effectuée dans le cadre des programmes PIREN-Seine et OPUR (Observatoire des Polluants URbains) / This thesis focuses on occurrence and fate of seven alkylphenols and bisphenol A (BPA) on a basin divided into a heavily urbanized part and a second part which underscore intense agricultural activities : the Seine River basin (Île-de-France Region). This study was divided into four different approaches. The first approach consists in studying the contamination of urban sources. To this end, the effluents of the five biggest wastewater treatment plants (WWTP) of the IDF Region, combined sewer overflows (CSO), urban runoff and total atmospheric fallouts were considered. This study highlight that BPA mainly occurs in wet-weather urban sources (CSO and urban runoff) while WWTP effluents are dominated by the nonylphenoxy acetic acid (NP1EC) which is a 4 nonylphenol (4 NP) precursor. The 4-NP was found in all investigated urban sources at level close to a hundred of nanogram per liter (ng.l-1). The second approach focuses on the assessment of contamination of natural matrices such as receiving surface water and soils at different scales. The first scale is the study of the Orgeval River basin which is representative of basins unpolluted by urban activities, while the second scale accounts the entire IDF region including the Parisian Metropolitan area. These two scales revealed the large spread of 4-NP to all investigated natural matrices within the Seine River basin. At the scale of the IDF Region, the influence of the Parisian Metropolitan Area was demonstrated on NP1EC and BPA concentrations within the Seine River. On a third step, the biodegradability of nonylphenolic compounds was investigated according to an innovative approach. The biodegradation rates were determined directly within the Seine River according to the ProSe model (Centre de Géoscience, école des Mines ParisTech) and specific sampling campaigns performed on the Seine River. The biodegradation rates found during this study disclosed high variabilities according to biological conditions of the Seine River. Actually, after an algal bloom, the biodegradation rates were found between 10 and 35 times higher than those established under common biological conditions. At last, the fluxes exported by the Seine River, at annually scale, were compared to those emitted by all investigated urban sources. At the scale of year 2010, fluxes of 4-NP and BPA emitted by all investigated urban sources are not predominant compared with those exported by the Seine River at the outlet of the Parisian Metropolitan Area. This result confirms the large spread of 4-NP and BPA at the scale of the entire IDF Region likely due to their important uses since the 1960's. This result also raises some questions about the origins of such fluxes found in Seine River and about the contamination of the upstream part.This thesis was performed within the framework of the PIREN-Seine and OPUR (Observatoire des Polluants URbains) research programs

My graduate work focused on the syntheses and pharmacology of species-selective aryl methylcarbamate acetylcholinesterase inhibitors to combat the malaria-transmitting mosquito, Anopheles gambiae. We identified six novel carbamates that demonstrated levels of target selectivity exceeding our project milestone of 100-fold. Among the C2-substituted phenylcarbamates examined (class II), 2'-(2- ethylbutoxy)phenyl N-methylcarbamate (9bd*) was extraordinarily selective (570-fold ± 72). The high level of selectivity observed for many of the class II carbamates was attributed to a helical displacement within the active site of An. gambiae acetylcholinesterase, able to accommodate carbamates with larger C2-substituted secondary β-branching side chains. Conversely, this type of side chain forms unfavorable interactions within the active site of human acetylcholinesterase. The C3-substituted carbamates (class I), such as terbam (9c), were less selective than many of the class II carbamates; however, class I carbamates related to terbam (9c) were highly toxic to An. gambiae. In particular, the contact toxicity measured for 9c (LC₅₀ = 0.037 mg/mL) was equal to the commonly used agricultural insecticide, propoxur (9a, LC₅₀ = 0.037 mg/mL). In total, seventy aryl carbamates were screened for their inhibition potency and contact toxicity towards An. gambiae. The common final step in all of these syntheses was the carbamoylation of a phenol, which normally proceeded in a 70 to 90% yield. Thirty seven novel carbamates are reported out of the seventy two prepared. Although sixteen of the phenols were commercially available, the others were prepared with known and adapted synthetic methodologies. The emerging structure-activity relationships led us to focus on the synthesis of 3-tert-alkylphenols (Class I) and 2-alkoxy or 2-alkylthio-substituted phenols (Class II). Three methods particularly stand out: First, we applied the methods of Tanaka to prepare 3-tert-alkylphenols wherein a methyl group was replaced by a trifluoromethyl group. Second, we adapted the methods of Tanaka to prepare 3-tert-alkylphenols that lack fluorine substitution. This method is competitive with the little known method of Reetz to convert aryl ketones to the corresponding 1,1-dimethylalkyl group and allows one to access electron rich tert-alkyl-substituted aromatics that are not accessible by the Friedel-Crafts alkylation (Friedel-Crafts restricted). Third, we found a convenient and high-yielding method for selective S-alkylation of 2-mercaptophenol. In addition to the synthesis of carbamates, the preparation of one hundred three intermediates, phenols, and electron rich tert-alkyl arenes are reported. / Ph. D.

Le milieu aquatique est le réceptacle ultime de la pollution environnementale. De nombreux micropolluants y sont présents et montrent des effets toxiques envers les systèmes aquatiques. La Directive Cadre Eau (DCE) a comme objectif la restauration du bon état écologique et chimique des milieux aquatiques d’ici 2015. Pour cela, elle impose des Normes de Qualités Environnementales (NQE) faibles et une surveillance accrue des masses d’eau. Au-delà des micropolluants réglementés, certains dits « émergents » ont été détectés à de faibles concentrations (ng.L-1) dans les systèmes aquatiques. Sous ce terme, sont regroupés les composés pharmaceutiques, certains pesticides, les hormones, etc. L’ensemble de ces micropolluants sont introduits dans l’environnement par plusieurs sources : dépôts atmosphériques, lessivage des sols, lixiviation et rejets industriels et/ou domestiques. Ces travaux de thèse ont porté plus précisément sur les alkylphénols, présents sur la liste des contaminants prioritaires dangereux de la DCE, leurs dérivés éthoxylés, le bisphénol A et les composés pharmaceutiques. Dans un premier temps, une attention particulière a été portée à l’analyse de ces composés. Les méthodes analytiques de chromatographie liquide couplée à la spectrométrie de masse simple (LC-MS) et en tandem (LC-MS/MS) pour les alkylphénols ont été optimisées en améliorant les contrôles qualités et en portant une attention particulière à l’extraction des composés sensibles aux contaminations extérieures (manipulateur, ambiance, etc.). Pour pallier aux problèmes liés à la contamination des échantillons par ces composés lors de l’extraction, la microextraction sur phase solide (SPME) et une méthode d’analyse par chromatographie en phase gazeuse couplée à la spectrométrie de masse simple (GC-MS) ont été dévelopées. Dans un second temps, le devenir et le comportement des alkylphénols, de leurs dérivés éthoxylés et des composés pharmaceutiques dans les stations d’épuration (STEP), sources d’introduction dans les systèmes aquatiques avérées, ont été étudiés. Cette étude a permis de mettre en évidence que les concentrations diminuent au cours des traitements dans les STEP pour tous les composés étudiés sauf pour l’acide alkylphénoxy acétique (NP1EC) qui est formé au cours des traitements secondaires ; la carbamazépine et dans une moindre mesure le diclofénac restent stables. Seuls les traitements tertiaires permettent une élimination significative de ces composés. La présence à plus de 50% des alkylphénols et de leurs dérivés éthoxylés dans la phase particulaire entraînent une adsorption non négligeable de ces composés dans les boues. Dans le but d’améliorer le suivi environnemental, les POCISTM standard (« Polar Organic chemical Integrative SamplersTM ») de configuration « pharmaceutiques » ont été développés lors d’expérimentations menées en laboratoire pour l’échantillonnage des alkylphénols, de leurs dérivés éthoxylés, du bisphénol A et des composés pharmaceutiques. Les alkylphénols et leurs dérivés éthoxylés sont accumulés avec un temps de latence dans les POCISTM standard montrant l’influence de la membrane sur le transfert de masse de ces composés. Les POCISTM standards ont été optimisés en changeant la nature des membranes pour l’échantillonnage des alkylphénols et de leurs dérivés éthoxylés. Ces nouveaux outils sont nommés POCISTM-like. Les POCISTM-Nylon 0,1 µm et 30 µm sont les POCISTM-like montrant un fort pouvoir concentrateur des alkylphénols, de leurs dérivés éthoxylés et du Bisphénol A tout en éliminant le temps de latence observé dans leur accumulation dans les POCISTM standards. Ces POCISTM-like ont par la suite été validés en mésocosmes puis dans le milieu naturel afin de mettre en évidence leur caractère intégratif, permettant ainsi de s’affranchir de l’effet matriciel et de détecter certains composés à des concentrations inférieures aux limites de quantification. / The aquatic environment is the ultimate receptacle of environmental pollution. Many micro-pollutants are present and show toxic effects to aquatic systems (bioaccumulation in tissues, inhibition of growth, endocrine dysfunction, etc.). The Water Framework Directive (WFD) aims to restore the good ecological and chemical quality of aquatic environments by 2015. For this, it imposes low Environmental quality standards (EQS) and increased monitoring of water bodies. Beyond regulated micro-pollutants, some "emerging" have been detected at low concentrations (ng L-1) in aquatic systems. Under this term are grouped pharmaceutical compounds, some pesticides, hormones, etc. All of these micro-pollutants are introduced into the environment through several sources: atmospheric deposition, soil leaching and industrial or domestic discharges.This work is specifically focused on alkylphenols, present on the list of priority hazardous compounds in the WFD, their ethoxylated derivatives, bisphenol A and pharmaceutical compounds. As a first step, particular attention was paid to the analysis of these compounds. Analytical methods of liquid chromatography coupled to mass spectrometry (LC / MS) and tandem mass spectrometry (LC-MS/MS) for alkylphenols were optimized by improving quality controls and paying attention to the extraction of sensitive compounds toward contamination (manipulator, atmosphere, etc.). To overcome the problems associated with sample contamination by these compounds during the extraction, solid phase microextraction (SPME) and a method of analysis by gas chromatography coupled to mass spectrometry (GC-MS) was developed. In a second step, the fate and behavior of alkylphenols, their ethoxylated derivatives and pharmaceutical compounds in sewage treatment plants (WWTPs), sources of introduction into aquatic systems proved, were studied. This study has allowed showing the decrease of concentrations during treatment in WWTPs for all compounds studied except for alkylphenoxy acetic acid (NP1EC) which is formed during secondary treatment, carbamazepine, and to a lesser extent diclofenac remain stable. Only tertiary treatments allow significant removal of these compounds. The presence of more than 50% of alkylphenols and ethoxylated derivatives in the particulate phase lead to significant adsorption of these compounds into sludges. In order to improve environmental monitoring, during experiments conducted in the laboratory POCISTM standard (Polar Organic Chemical Integrative Samplers), "pharmaceuticals" configuration, have been developed for sampling alkylphenols, their ethoxylated derivates, bisphenol A and pharmaceutical compounds. Alkylphenols and their ethoxylated derivatives are accumulated with a lag phase in standard POCISTM showing the influence of the membrane on the mass transfer of these compounds. The standard POCISTM were optimized by changing the nature of the membranes for sampling alkylphenols and their ethoxylated derivatives. These new tools are named POCISTM-like. The POCISTM-Nylon 0.1 µm and 30 µm are POCISTM-like showing a strong power concentrator for alkylphénols, their ethoxylated derivatives and BPA while eliminating the lag phase observed in standard POCISTM. These POCISTM-like were subsequently validated in mesocosms and in the environment in order to highlight their integrative nature, allowing to overcome the matrix effect and to detect some compounds at concentrations below the limits of quantification.

Les alkylphénol-polyéthoxylés et les substances pharmaceutiques appartiennent à la classe des contaminants émergents qui sont depuis peu étudiés dans les milieux naturels. Ces composés d’usage très répandu (aussi bien en termes d’applications qu’en termes de quantité) sont introduits dans le milieu aquatique, via les stations d’épuration, principalement et sont susceptibles d’engendrer des effets toxiques sur les organismes vivants dans ces milieux. La première partie de ce travail de thèse a consisté en le développement et la validation de différentes méthodologies d’échantillonnage (ponctuel et intégratif (POCIS)), de différents protocoles d’extraction (SPE, extraction assistée par micro-ondes) et d’analyse (CL/SM, CL/SM/SM), nécessaires pour un dosage fiable des alkylphénol-polyéthoxylés et des substances pharmaceutiques dans les différents compartiments des systèmes aquatiques (phases dissoute, particulaire et sédimentaire, organismes biologiques). Ensuite, un bilan de la contamination de différents systèmes aquatiques (le bassin de d’estuaire de Seine, la Garonne et la Gironde, la baie de la Vilaine, la baie de l’Authie, l’Adour, la rade de Marseille) a été dressé. Une contamination généralisée par ces composés a été mise en évidence pour l’ensemble des sites étudiés. Les concentrations mesurées apparaissent extrêmement variables selon la classe de molécule considérée, les sites et le temps avec des concentrations comprises entre le ng.l-1 et la dizaine de µg.l-1 pour les phases dissoutes et de la dizaine de ng.g-1 et la dizaine de µg.g-1 pour les phases solides (plusieurs centaines de µg.g-1 dans les boues d’épuration). Ces études ont également permis de documenter la présence et le devenir des molécules ciblées dans les stations d’épuration et ont permis d’en évaluer l’efficacité quant l’abattement des substances incriminées. Enfin, ces travaux ont également permis de mettre en évidence des phénomènes de partition entre les phases dissoutes et les phases solides ainsi que des phénomènes de transferts vers les organismes du milieu. / Alkylphenol-polyethoxylates and pharmaceutical substances belong to the class of the emerging contaminants which have been recently studied in natural environments. These compounds of very widespread use (in terms of applications as well as in terms of quantity) are introduced into the aquatic environment, via the wastewater treatment plants, mainly, and are likely to generate toxic effects on the living organisms in these systems. The first part of this work consisted in the development and validation of various methodologies of sampling (grab sampling and integrative sampling (POCIS)), of various protocols of extraction (SPE, microwaves assisted extraction) and of analysis (LC/MS, LC/MS/MS), necessary for a reliable quantification of alkylphenol-polyethoxylates and pharmaceutical substances in the various compartments of aquatic systems (phases dissolved, particulate and sedimentary, biological organisms). Then, an assessment of the contamination of numerous aquatic systems (the catchment area of the Seine estuary, the Garonne and the Gironde, the bay of Vilaine, the bay of Authie, the Adour, the Mediterranean coast of Marseilles) was undertaken. A generalized contamination by these compounds was highlighted for all the studied sites. The measured concentrations appear to be extremely variable according to the class of molecule considered, the sites and time with concentrations ranging from the ng.l-1 to tens of µg.l-1 for the dissolved phases and from tens of ng.g-1 to tens of µg.g-1 for the solid phases (several hundreds of µg.g-1 in the clarification sludge). These studies also made it possible to document the presence and the fate of these molecules in the French wastewater treatment plant and made it possible to evaluate their effectiveness to remove the studied compounds. Lastly, this work also made it possible to highlight phenomena of partition between the dissolved phases and the solid phases as well as phenomena of transfers through the biological organisms.

Cette étude s’attache à la caractérisation physico-chimique des contaminants des emballages alimentaires organiques, précisément les phtalates et les alkylphénols, en terme de solubilité aqueuse, coefficient de partage octanol-eau et pression de vapeur. Cette caractérisation se situe dans le cadre des règlementations REACH concernant l’identification des substances chimiques toxiques. Les mesures expérimentales de solubilité aqueuse sont effectuées par la méthode dynamique de saturation dans un intervalle de température [298.15-328.15K], celles du coefficient de partage octanol-eau avec la méthode « shake-flask » à 298.15. Les mesures de pression de vapeur sont réalisées avec la méthode dynamique de saturation dans un intervalle de température [313.15-423.15K] et validées avec la méthode statique. A partir de ces mesures, les coefficients de partage air-eau et octanol-air sont déterminés. En addition des mesures expérimentales, une prédiction de ces propriétés est effectuée avec les modèles thermodynamiques : UNIFAC originale, UNIQUAC, NRTL et COSMO-sac-dsp. A l’issue de ces résultats, une évaluation quantitative et qualitative de chacun des modèles est effectuée. Cette évaluation facilitera l’optimisation des paramètres de chacun des modèles des deux familles dans le but de créer un modèle de prédiction du phénomène de migration de l’emballage vers l’aliment / The aim of this study is the physical-chemical characterization of the organic food packaging contaminants, particularly phthalates and alkyl phenols, in terms of aqueous solubility, octanol-water partition coefficient and vapor pressure. This characterization falls within the scope of REACH regulations for the identification of chemical substances. The aqueous solubility measurements are performed using the dynamic saturation method in a temperature range of [298.15 – 328.15K], those of octanol-water partition coefficient with the “shake-flask” method at 298.15K. The vapor pressure measurements are carried out with the “dynamic saturation method” in a temperature range between 313.15 and 423.15K, and validated with the static method. These measurements are used in the determination of air-water and octnol-air partition coefficients. Beside experimental measurements, these poperties are predicted using thermodynamic models: UNIFAC originale, UNIQUAC, NRTL and COSMO-sac-dsp. A qualitative and quantitative evaluation is performed for each model. This evaluation will facilitate the optimization of the models’ parameters concerning phthalates and alkyl phenols in order to generate a model for the contaminants migration process