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The Removal of Chlorophenoxy Herbicides from Drinking Water by Activated Carbon Adsorption and Liquid Core Microcapsule Perstraction

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The Removal of Chlorophenoxy Herbicides from Drinking Water by Activated Carbon Adsorption and Liquid Core Microcapsule Perstraction The Removal of Chlorophenoxy Herbicides from Drinking Water by Activated Carbon Adsorption and Liquid Core Microcapsule Perstraction Nora Engels BSc. Chemical and Pharmaceutical Sciences Student ID: 53306348 For the award of Master of Science to the Dublin City University Faculty of Science, School of Biotechnology Supervisors: Prof. Marison, Dr. Tobin, Dr. Morrissey and Dr. Nolan Submitted: January 2012 One volume Declaration I hereby certify that this material, which I now submit for assessment on the programme of study leading to the award of Master of Science is entirely my own work, that I have exercised reasonable care to ensure that the work is original, and does not to the best of my knowledge breach any law of copyright, and has not been taken from the work of others save and to the extent that such work has been cited and acknowledged within the text of my work. Signed: Student ID: 53306348 Date: Contents Abstract 9 Acknowledgments 10 List of Tables 11 List of Figures 14 Nomenclature 19 List of Equations 23 1 Introduction to pesticides, their application and detection in drinking water 24 1.1 Introduction . 25 1.2 Pesticides . 25 1.2.1 Historical background . 25 1.2.2 Overview of pesticide characterisation and classification . 27 1.2.3 Global usage statistics . 29 1.2.4 Effect on health . 32 1.3 Pesticide detection in drinking water . 33 1.3.1 Fate of pesticides in the environment . 33 1.3.2 Safeguards and standards . 34 1.3.2.1 Drinking Water Standard . 34 1.3.2.2 Integrated Pest Management . 35 1.3.3 Persistence and detection in drinking water . 36 3 1.4 Activated Carbon . 37 1.4.1 Preparation of activated carbon . 38 1.4.1.1 Physical activation . 38 1.4.1.2 Chemical activation . 39 1.4.2 Liquid phase application . 40 1.4.3 Adsorption isotherms for single component systems . 41 1.5 Liquid-core microcapsules . 43 1.5.1 Inner core materials . 44 1.5.2 Shell materials . 44 1.5.3 Production of microcapsules . 44 1.6 Project proposal . 48 1.7 Project strategy . 49 2 The development and validation of a rapid high performance liquid chro- matography (HPLC) detection method for MCPA, 2,4-D and dichlorprop chlorophenoxy herbicides 51 2.1 Introduction . 52 2.2 Materials and methods . 52 2.2.1 Reagents and preparation of standards . 52 2.2.2 High performance liquid chromatography . 53 2.2.2.1 Gradient multicomponent analysis . 53 2.2.2.2 Isocratic single component analysis . 54 2.2.3 Validation procedure and criteria . 55 2.2.3.1 Precision . 55 2.2.3.2 Accuracy . 55 2.2.3.3 Limit of Detection (LOD) . 55 2.2.3.4 Limit of quantitation (LOQ) . 56 2.2.3.5 Linearity and range . 56 2.2.3.6 Capacity factor . 56 4 2.2.3.7 Tailing factor . 56 2.2.3.8 Theoretical plates . 57 2.3 Results and discussion . 57 2.3.1 UV-Visible profiles and wavelength selection for HPLC . 57 2.3.2 Method development . 57 2.3.2.1 Gradient method development for multicomponent analysis 57 2.3.2.2 Isocratic method development for single component anal- ysis . 59 2.3.3 Injection volume response . 61 2.3.4 Validation . 61 2.4 Conclusion . 64 3 Removal of chlorophenoxy herbicides from water using activated carbon types typically used in the drinking water treatment process: Comparing the activated carbon and the effect of pH 65 3.1 Introduction . 66 3.2 Materials and methods . 66 3.2.1 Chemicals . 66 3.2.2 Activated carbons . 67 3.2.3 Experimental . 69 3.2.4 Detection method . 69 3.2.5 Data analysis . 69 3.3 Results and discussion . 70 3.3.1 Initial pH experiments . 70 3.3.2 Equilibrium modelling . 72 3.3.3 Effect of solution pH on herbicide adsorption . 79 3.4 Conclusions . 81 4 Studying the effect and interference of humic acid addition on the activated carbon adsorption process 82 5 4.1 Introduction . 83 4.2 Materials and methods . 84 4.2.1 Chemicals . 84 4.2.2 Activated carbons . 84 4.2.3 Experimental . 85 4.2.3.1 Humic acid adsorption to activated carbon . 85 4.2.3.2 Herbicide adsorption in the presence of humic acid . 85 4.2.3.3 Adsorption experiments with activated carbon pre-loaded with humic acid . 85 4.2.4 Detection methods . 86 4.2.4.1 High performance liquid chromatography . 86 4.2.4.2 UV-Visible spectroscopy . 86 4.2.4.3 Fluorescence spectroscopy . 86 4.2.5 Data analysis . 86 4.2.5.1 Activated carbon equilibrium concentrations . 86 4.2.5.2 Differential UV-Visible spectroscopy . 87 4.2.5.3 Stern-Volmer relationship . 87 4.2.5.4 Perrin model . 87 4.3 Results and discussion . 88 4.3.1 Humic acid adsorption to activated carbon . 88 4.3.2 Competitive adsorption behaviour . 88 4.3.3 Herbicide adsorption to humic acid pre-loaded activated carbon . 90 4.3.4 Interaction between herbicides and humic acid . 91 4.3.4.1 UV-Visible spectroscopic analysis . 91 4.3.4.2 Fluorescence spectroscopy . 92 4.4 Conclusions and future work . 108 5 Removal of chlorophenoxy herbicides from water: Using liquid core micro capsules as a comparison to activated carbon adsorption 110 6 5.1 Introduction . 111 5.2 Materials and methods . 111 5.2.1 Chemicals . 111 5.2.2 Experimental . 112 5.2.3 Preparation of liquid core microcapsules . 112 5.2.4 Measurement of capsule size distribution . 114 5.2.4.1 Liquid-liquid extraction . 114 5.2.4.2 Capsular perstraction . 114 5.2.4.3 Herbicide removal by activated carbon adsorption . 116 5.2.4.4 Activated carbon equilibrium studies . 117 5.2.5 Detection method . 117 5.2.6 Determination of mass transfer . 117 5.3 Results and discussion . 118 5.3.1 Solvent selection . 118 5.3.1.1 Capsular perstraction of herbicides using dibutyl seba- cate liquid-core microcapsules . 118 5.3.1.2 Liquid-core microcapsule perstraction compared to acti- vated carbon adsorption . 120 5.3.2 Solvent screening . 121 5.3.3 Octanol liquid core microcapsules . 122 5.3.4 Castor oil liquid core microcapsules . 124 5.4 Conclusions and future work . 126 6 Final discussion, conclusions and future work 128 6.1 HPLC method . 129 6.2 Removal of chlorophenoxy herbicides by activated carbon adsorption . 129 6.3 The interaction between humic acid, activated carbon and chlorophenoxy herbicides . 130 7 6.4 Chlorophenoxy herbicide remediation by liquid-core microcapsule perstrac- tion . 130 6.5 Comparing activated carbon adsorption to liquid-core microcapsule per- straction . 131 References 133 Appendix: 147 A Equations used for HPLC validation 148 B Supplementary data for Chapter 3 151 8 Abstract Drinking water quality reports have highlighted a persistent trend in pesticide detection in the Republic of Ireland. One of the main concerns of the drinking water industry is that consistent pesticide removal rates do not occur despite the existence of activated carbon (AC) treatment regimes in most plants. The present work examines the removal of three chlorophenoxy herbicides (MCPA, 2,4-D and dichlorprop) from aqueous solutions by AC adsorption and a novel liquid-core microcapsule perstraction system. Herbicide adsorption to three ACs used in the drinking water industry was dependant on the pH of the water. As pH increased, adsorption decreased. Herbicide adsorption to AC was further decreased when humic acid (HA) was added to the contacting system. HA uptake by AC was mini- mal, possibly due to the large molecular weight associated with HA. Herbicide adsorption to AC was hindered by the presence of HA in the sample solutions and by HA pre-saturated to the AC. The possible interaction between herbicides and HA was investigated by UV- Visible and fluorescence spectroscopy to evaluate any potential interactions occurring dur- ing site competition. Weak spectral changes were observed and the florescence intensity was quenched by HA addition, suggesting that some form of interaction occurs. Capsular perstraction of MCPA, 2,4-D and dichlorprop by dibutyl sebacate liquid-core microcapsules (LCMs) was demonstrated. The use of LCMs results in between 9 and 18 % of the herbi- cides being extracted within 60 minutes of capsule addition. The quantity of LCMs added was equal to 1 g of oil core and could be increased to achieve higher levels of extraction. The results were compared to adsorption by 1 g of activated carbon (AquaSorb 2000) over the same time period of 100 minutes. Although the remediation of herbicides was more effective, AC equilibrium had not been reached after 100 minutes. The results demonstrate the time efficiency incurred by using LCMs.
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