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Copyright © 2010. Nova Science Publishers, Incorporated. All rights reserved. Bisphenol A and Phthalates: Uses, Health Effects and Environmental Risks : Uses, Health Effects and Environmental Risks, Nova Science Publishers,

Copyright © 2010. Nova Science Publishers, Incorporated. All rights reserved. Bisphenol A and Phthalates: Uses, Health Effects and Environmental Risks : Uses, Health Effects and Environmental Risks, Nova Science Publishers,

CHEMICAL ENGINEERING METHODS AND TECHNOLOGY

BISPHENOL A AND PHTHALATES

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USES, HEALTH EFFECTS AND ENVIRONMENTAL RISKS

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Bisphenol A and Phthalates: Uses, Health Effects and Environmental Risks : Uses, Health Effects and Environmental Risks, Nova Science

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Bisphenol A and Phthalates: Uses, Health Effects and Environmental Risks : Uses, Health Effects and Environmental Risks, Nova Science

CHEMICAL ENGINEERING METHODS AND TECHNOLOGY

BISPHENOL A AND PHTHALATES USES, HEALTH EFFECTS AND ENVIRONMENTAL RISKS

Copyright © 2010. Nova Science Publishers, Incorporated. All rights reserved.

BRADLEY C. VAUGHN EDITOR

Nova Science Publishers, Inc. New York

Bisphenol A and Phthalates: Uses, Health Effects and Environmental Risks : Uses, Health Effects and Environmental Risks, Nova Science

Copyright © 2010 by Nova Science Publishers, Inc. All rights reserved. No part of this book may be reproduced, stored in a retrieval system or transmitted in any form or by any means: electronic, electrostatic, magnetic, tape, mechanical photocopying, recording or otherwise without the written permission of the Publisher. For permission to use material from this book please contact us: Telephone 631-231-7269; Fax 631-231-8175 Web Site: http://www.novapublishers.com

NOTICE TO THE READER The Publisher has taken reasonable care in the preparation of this book, but makes no expressed or implied warranty of any kind and assumes no responsibility for any errors or omissions. No liability is assumed for incidental or consequential damages in connection with or arising out of information contained in this book. The Publisher shall not be liable for any special, consequential, or exemplary damages resulting, in whole or in part, from the readers’ use of, or reliance upon, this material.

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Independent verification should be sought for any data, advice or recommendations contained in this book. In addition, no responsibility is assumed by the publisher for any injury and/or damage to persons or property arising from any methods, products, instructions, ideas or otherwise contained in this publication. This publication is designed to provide accurate and authoritative information with regard to the subject matter covered herein. It is sold with the clear understanding that the Publisher is not engaged in rendering legal or any other professional services. If legal or any other expert assistance is required, the services of a competent person should be sought. FROM A DECLARATION OF PARTICIPANTS JOINTLY ADOPTED BY A COMMITTEE OF THE AMERICAN BAR ASSOCIATION AND A COMMITTEE OF PUBLISHERS. LIBRARY OF CONGRESS CATALOGING-IN-PUBLICATION DATA Bisphenol A and phthalates : uses, health effects and environmental risks / Editor, Bradley C. Vaughn. p. cm. ISBN H%RRN 1. Bisphenol A--Toxicology. 2. Bisphenol A--Environmental aspects. 3. Phthalate esters--Toxicology. 4. Phthalate esters--Environmental aspects. I. Vaughn, Bradley C. RA1242.P58B57 2009 615.9'51--dc22 2010002298

Published by Nova Science Publishers, Inc. † New York

Bisphenol A and Phthalates: Uses, Health Effects and Environmental Risks : Uses, Health Effects and Environmental Risks, Nova Science

CONTENTS Preface Chapter 1

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Chapter 2

Chapter 3

Chapter 4

vii Review on Analytical Methods for the Determination of Regulated Phthalates Considering as Priority Substances by European and American Regulations in the Environment Jean-Baptiste Baugros, Cécile Cren-Olivé and Marie-Florence Grenier-Loustalot Analytical Methods for Phthalates Determination in Biological and Environmental Samples: A Review P. Bermejo Barrera, M. C. Barciela Alonso, C. Pérez Feás, E. Peña Vázquez and P. Herbello Hermelo Preparation and Characterization of Phthalated Hemicelluloses and Cellulose Derivatives Chuan-Fu Liu, Feng Peng, Jun-Li Ren, Feng Xu and Run-Cang Sun Bisphenol A: Uses, Health Effects and Environmental Risks S. K. Nataraj and T. M. Aminabhavi

1

29

59

85

Chapter 5

Viscosity Reduction of Polycarbonates Supakanok Thongyai

109

Chapter 6

Phthalates: Identification, Properties and Health Effects Se-Kwon Kim and Yong Li

135

Chapter 7

Bisphenol A Based Polybenzoxazine and Its Tailored Systems K.S. Santhosh Kumar and C.P. Reghunadhan Nair

155

DEHP-Induced Reproductive and Developmental Toxicity and PPAR Yuki Ito, Yumi Hayashi and Tamie Nakajima

173

Chapter 8

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vi

Contents

Chapter 9

Pitfalls in the Analysis of Bisphenol A: Sources and Solutions H. Gallart-Ayala, E. Moyano and M. T. Galceran

185

Chapter 10

Polymeric Particles for the Removal of Endocrine Disruptors Changsheng Zhao, Kaiguang Yang, Zongbin Liu, Jin Chang and Norio Nishi

197

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Index

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203

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PREFACE Bisphenol A is a difunctional building block of several important plastics and plastic additives. Suspected of being hazardous to humans since the 1930s, concerns about the use of bisphenol A in consumer products were regularly reported in the news media in 2008 after several governments issued reports questioning its safety, causing some retailers to remove products made of it from their shelves. Additionally, phthalates, are esters of phthalic acid and are mainly used as plasticizers (substances added to plastics to increase their flexibility, transparency, durability, and longevity). They are primarily used to soften polyvinyl chloride. This book examines both bisphenol A and phthalates discussing and presenting numerous topical and related data on these compounds and their uses, health effects and environmental risks. Chapter 1 - Phthalates are organic compounds which are produced every year in millions of tons in the whole world. Precisely, phthalates esters are used as additives for plastic materials in widespread applications. Due to their extremely diverse uses, they became ubiquitous chemicals in today’s environment contaminating parts all the way to groundwaters or mineral waters and sediments. Face to their strong environmental impact and their large diffusion, European Commission and Environmental Protection Agency of United States have established regulations to limit the human exposure. Di-ethylhexyl phthalate, di isodecyl phthalate and di isononylphthalate are strongly monitored because they are the three most used of the phthalates esters compounds. All this chemicals induce endocrine disrupting effects as well as BisPhenol A (BPA) which is another Endocrine Disrupting Compound (EDC) employed to make polycarbonate or epoxy resins often blended with phthalates. In consequence, many products can contain DEHP, DMP, DBP and BPA which may pose a significant health risk for population by contamination of the environment. Thus, analytical methods have been developed and several applied to real samples allowing the detection and quantification of phthalates esters and BPA in aqueous and solid environmental parts. Chapter 2 - This chapter summarizes and discusses the analytical methods and techniques described in the literature for phthalate determination in different matrix samples (water, soil, sediments, sludge, air and biological samples). Different sample treatments, extraction and preconcentration steps, such as liquid-liquid extraction (LLE), solid phase extraction (SPE), solid phase microextraction (SPME), stir bar sportive extraction (SBSE) and solid/liquid extraction (SLE) have been evaluated. Separation techniques such as gas chromatography (GC) or high performance liquid chromatography (HPLC) coupled with different detectors have been compared in terms of detection limits and practical applications.

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viii

Bradley C. Vaughn

Chapter 3 - Phthaloylation of hemicelluloses with phthaloyl dichloride and cellulose with phthalic anhydride is an efficient way to improve their lipophilicity and hydrophilicity, respectively. In addition, the phthaloylation of hemicelluloses and cellulose is a key precursor to prepare polysaccharide derivatives by regioselective and quantitative chemical modification. In this review, rapid phthaloylation of wheat straw hemicelluloses with phthaloyl dichloride (PdC) in N,N-dimethylformamide/lithium chloride (DMF/LiCl) system by microwave irradiation was introduced. The effect of the molar ratios of xylose units in hemicelluloses to phthaloyl dichloride on the degree of substitution was investigated. In addition, homogeneous modification of cellulose with phthalic anhydride in roomtemperature ionic liquid 1-allyl-3-methylinidazolium chloride and 1-butyl-3methylinidazolium chloride was reported. The results showed the degree of substitution (0.10-2.54) increased with the increment of reaction temperature, reaction time, and the molar ratio of phthalic anhydride/anhydroglucose units in cellulose under the conditions given. The products were characterized by FT-IR and solid-state CP/MAS 13C NMR spectroscopy, and the results showed that the phthalation reaction at C-6, C-2, and C-3 positions of the cellulose all occurred. Furthermore, it was found that the crystallinity of the cellulose was completely disrupted and the native cellulosic polymer was degraded in the ionic liquid under the conditions used. Similarly, it should be noted that microwave irradiation did result in more degradation of the macromolecular hemicelluloses than conventional heating technique under the conditions given. Chapter 4 - Bisphenol-A (BPA) is the molecular building block for important industrial chemicals, polycarbonate plastics and epoxy resins, which are used in a wide variety of applications. For instance, polycarbonate is used in eyeglass lenses, medical equipment, water bottles, digital media like CDs/DVDs, cell phones, consumer electronics, computers, electrical equipment, household appliances, safety shields, construction glazing, sports safety equipment, and automobiles. Among the many uses of epoxy resins, industrial floorings, adhesives, industrial protective coatings, powder coatings, automotive primers, can coatings and printed circuit boards are quite popular. Bisphenol-A is a synthetic chemical originally developed as a synthetic estrogen. It is now one of the highest volume chemicals produced in the World with over six billion pounds manufactured every year Chapter 5 - Normally, the melt viscosity of polycarbonate can be reduced, according to the blending conditions, with a lower melt viscosity polymer such as ABS or polyolefins and the reduction in blend melt viscosity is compensated with the reduction in tensile strength of the blends. However, there are three more distinct methods of reducing the melt viscosity of polycarbonate than the normal blending with lower melt viscosity polymers. The first method is to incorporate a low molar mass liquid crystal as small as 1%w to polycarbonate, which reduced the melt viscosity of the polycarbonate down approximately 10 times that from pure polycarbonate. Nuclear Reaction Analysis (NRA) proved the more mobile polycarbonate molecules when added 1%wt low molar mass liquid crystal. The second method is to incorporate as little as 2%wt of the high molar mass liquid crystal that has the melting temperature of the polycarbonate lie within the window of anisotropic phases, which reduced the melt viscosity of the polycarbonate approximately 5 times. The last method utilized the transesterification reaction of polycarbonate with ester of various sizes ranging from small molecule of diallyl orthopathalate to large molecule of thermotropic liquid crystal polyester. The reduction of the melt viscosity depended on the extent of the transesterification reaction conditions, and the amount of ester added, which were in the range of 1 to 100 times when

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Preface

ix

added the ester up to 80%wt. The melt viscosity of the liquid crystal blend of polycarbonate can also be reduced by added an appropriate amount of nanosilica to the blend. The lower melt viscosity of polycarbonate enables the process of the small sophisticate mould especially injection molding. Chapter 6 - Derivatives of phthalates are increasingly becoming the focus of researchers, owing to the variety of interesting activities and mechanisms that have been recently reported. In particular, reports of new phthalate derivatives with novel bioactivities as well as action mechanisms at molecular and cell levels, which are published frequently in recent years, have already attracted a great deal of attention in a great many research fields. This encouraged us to systematically review the latest achievements in this field for an investigation of phthalate derivatives, in terms of its chemistry, bioactivities, and future prospects. Accordingly, these types of derivatives should be given fair evaluation for their possible medical and environmental applications and controls in the future. Chapter 7 - Polybenzoxazines have emerged as a new generation phenolic resin and have attracted great interest because of their attractive characteristics, such as low water absorption, high modulii, good flame retardance, high glass transition temperature and low moisture absorption. This polymer opens up new vista in the field of addition curable thermosetting resins. Together with the structure modification by designing new benzoxazine monomers, there are many other approaches also reported for improving the performance of polybenzoxazines such as polymer blends, copolymers, alloys and nanocomposites. Despite the fact that several polybenzoxazines from various monomers with additional polymerisable moieties and with different backbone structures have emerged, the polybenzoxazine that dominates the literature hitherto is the bisphenol A- based one. The bisphenol A based polymer exhibits tremendous thermal and mechanical features and good thermal properties and it is presented as a reference material in all other investigations. Accordingly, this traditional polybenzoxazine deserves a special attention and hence a comprehensive survey of its chemistry and application is warranted. In this chapter, the characteristics of bisphenol A based polybenzoxazine and its various tailored polymeric systems are described. Chapter 8 - Di(2-ethylhexyl)phthalate (DEHP) is the phthalate most widely used as a plasticizer of polyvinyl chloride products. DEHP is metabolized by lipase to a monoester, mono(2-ethylhexyl) phthalate, which transactivates peroxisome proliferator-activated receptor α (PPARα), exerting both physiological and toxicological responses to reproductive organs and some others such as the liver and kidneys. The literature on the reproductive and developmental toxicities of DEHP is reviewed here in relation to PPARα. Several studies in rodents have shown that DEHP induces testicular or ovary damage, a decrease of litter size and an increase of fetal mortality, which may, in part, be associated with the functional activation of PPARα by the monoester. Several epidemiological studies have suggested possible relationships between DEHP exposure and reproductive or developmental toxicity in humans, though their relevance to PPARα is unknown. Chapter 9 - Due to the widespread use and manufacture of polycarbonate plastics and epoxy resins, Bisphenol A (BPA) (2,2-bis[4-hydroxyphenyl] propane) is frequently found at low concentration levels in environment matrices such as water, river sediments and sewage sludge. Analysis of this compound requires extensive sample treatment, filtration, extraction, pre-concentration and clean-up. Subsequently, highly efficient separation techniques, such as gas chromatography (GC) and liquid chromatography (LC), mainly coupled to mass

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Bradley C. Vaughn

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spectrometry (MS), are generally used for its identification and quantification. In this paper the key problems encountered in the analysis of BPA, the symptoms and remedies are discussed. Accurate determination of BPA at ultra-low concentrations is frequently hindered by many factors mainly attributable to its ubiquity, such as contamination from glassware, syringes, and other materials. Furthermore, water purification systems may contaminate with BPA the purified water. In addition, problems arising from the instrumental analysis when using liquid chromatography and gas chromatography coupled to mass spectrometry (LC-MS and GC-MS) mainly related to derivatization in GC-MS, to low ionization efficiency and ion suppression effects in LC-MS and to fragmentation in tandem mass spectrometry (MS/MS) are also discussed. Chapter 10 - Polymeric porous particles are prepared using a phase transition technique from polysulfone and polyethersulfone. The particles are different from the common microspheres and particles; in this case, the particle size ranges from about 1 mm to about 2.5 mm, with a skin layer, under which is a finger-like structure. In addition, the particles have a very large porosity, which induces a high specific surface area for binding endocrine disruptors. The endocrine disruptors having high octanol-water distribution coefficients could bind to the polysulfone particles by hydrophobic interaction. DNA-modified particles could more effectively remove environmental hormone with a planar structure. Molecular imprinting particles have specific sites, which allow the specific recognition to endocrine disruptors.

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In: Bisphenol A and Phthalates: Uses, Health Effects… ISBN: 978-1-60741-701-9 Editor: Bradley C. Vaughn © 2010 Nova Science Publishers, Inc.

Chapter 1

REVIEW ON ANALYTICAL METHODS FOR THE DETERMINATION OF REGULATED PHTHALATES CONSIDERING AS PRIORITY SUBSTANCES BY EUROPEAN AND AMERICAN REGULATIONS IN THE ENVIRONMENT Jean-Baptiste Baugros 1, Cécile Cren-Olivé 1,2 and Marie-Florence Grenier-Loustalot 1

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1

Service Central d’Analyse du CNRS USR 059, Chemin du, Canal, 69360 Solaize, France 2 Laboratoire de Chimiométrie UMR 5180 43 Bd du 11, novembre 1918, Bat. 308 D, 69622 Villeurbanne, France

ABSTRACT Phthalates are organic compounds which are produced every year in millions of tons in the whole world. Precisely, phthalates esters are used as additives for plastic materials in widespread applications. Due to their extremely diverse uses, they became ubiquitous chemicals in today’s environment contaminating groundwaters or mineral waters and sediments. Face to their strong environmental impact and their large diffusion, European Commission and Environmental Protection Agency of United States have established regulations to limit the human exposure. Di-ethylhexyl phthalate, di isodecyl phthalate and di isononylphthalate are strongly monitored because they are the three most used of the phthalates esters compounds. All this chemicals induce endocrine disrupting effects as well as BisPhenol A (BPA) which is another Endocrine Disrupting Compound (EDC) employed to make polycarbonate or epoxy resins often blended with phthalates. In consequence, many products can contain DEHP, DMP, DBP and BPA which may pose a significant health risk for population by contamination of the environment. Thus, analytical methods have been developed and several applied to real samples allowing the detection and quantification of phthalates esters and BPA in aqueous and solid environmental parts.

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2

Jean-Baptiste Baugros, Cécile Cren-Olivé and Marie-Florence Grenier-Loustalot In this chapter, we propose firstly to present the properties and the environmental fate of the most used phthalates molecules and BPA. A special part on substitution of phthalates to other chemicals like alkyl citrates, adipate or cyclohexane di-carboxylates, isosorbide diesters or trialkyl trimellitates is included to anticipate the future limitations of phthalates. Then, we take an overview of the most recently analytical methods about phthalates and BPA. Finally, we summarize the concentrations noticed by analysts in various environmental parts in the entire world. Comparison of real levels with toxic limits will let us to position the pollution problem and the human health exposure.

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INTRODUCTION Phthalates are synthetic chemicals that are ubiquitous in our society since they are used in several household and industrial manufactured products. They can be included in food/beverages coatings, children’s plastic toys, personal care products, medical tubing, cosmetics or lubricants, paints and formulation of pesticides. They play a role of plasticizers, softeners and stabilizers in plastics or emollients and humectants in liquid formulations or antifoaming in aerosols. In 2003, more than 4.6 millions of tons were produced in the world [1]. Di-2-ethylhexyl phthalate is the most used about twenty commercial phthalates esters, representing more than 50% of the whole amount. The four other widely used phthalates are di isodecyl phthalate, di isononylphthalate, di butylphthalate and benzyl butyl phthalate. Bisphenol A is another high-production industrial chemical used to manufacture polycarbonate plastics and epoxy resins in combination with phthalates. All this chemicals are suspected to mimic hormones and therefore interfere with the endocrine system communication of many organisms [2-6]. Because of their widespread use and high-production volumes, concentrations in various environmental parts have been reported [7-26], reflecting a constant and diffuse release into waters, soils or air. They are discharged into the environment throughout the cycle of their production, use and disposal. Their environmental fate received increasing attention because of potential health effects in animals and humans. Several studies [3, 5, 8, 12, 15, 21, 27] suggested that they may bioaccumulate in aquatic organisms and degrade from diesters into phthalic acid. Even if the degradation occurs in few days, the constant and large exposure induces chronic toxicity. In addition, phthalates and bisphenol A are taken up into the food chain by meat, fish or dairy products which are contaminated by their migration from plastic containers and wraps. Consequently, European and American agencies have decided to include phthalates and bisphenol A in their priority products list [28-31]. Particularly, phthalates have been forbidden in plastic baby’s toys and bottles by European Union (EU) [32]. In order to anticipate the future forbidden use of phthalates, industrial have evaluated substitute products like adipates or trialkyl trimellitates, citrates, cyclohexane di-carboxylates or isosorbide diester compounds. In order to give accurate answers to government regulations and to scientific studies like ecotoxicology and environmental assessment, analytical methods need to be evaluated [33]. The scientists have given a focus on the development of environmental analysis of endocrine disrupting compounds (EDCs) like phthalates and bisphenol A at very low levels in waters, soils or air. Phthalates and bisphenol A have been extensively studied and they still attract the attention of analysts. As chromatography coupled to mass spectrometry begins to be popular

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Review on Analytical Methods for the Determination of Regulated Phthalates …

3

and according to the sensibility that environmental regulations requires it is the most appropriate analytical technique to detect and quantify them [33]. Thus, the levels detected in waters for a single phthalate were in the range of 0.1 to 100 μg.L-1 [15], 0.05 to 480 μg.g-1 [15] in sediments/sludge and 11 to 4300 ng.m-3 in indoor air [34]. This concentrations need to be linked with the toxicity of each plasticizers, and even if phthalates exhibit low acute toxicity with lethal dose 50 values (LD50) of 1-30 g.kg-1, short or long-term studies show adverse effects in liver, kidney, thyroid gland and tissues [5]. This review on phthalates and bisphenol A in the environment is composed of three parts. Firstly, we will present their properties and the new regulations about them, followed by their environmental fate and various pathways of their degradation. Complementary description will be given on substitute molecules. Then, we will focus on new and high performance analytical methodologies developed to detect and quantify phthalates and bisphenol A. Finally, we will give a summary of results obtained for real environmental samples which we will discuss with the toxic levels.

I. PROPERTIES, REGULATION AND SUBSTITUTE CHEMICALS FOR PHTHALATES

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The physicochemical properties of phthalates make of them environmental contaminants. Consequently, regulations have been edited and industrials are looking for substitute products. Except the negative side induces by their environmental ubiquity and their extremely diverse and widespread applications, the positive side is that the transformation and the degradation of phthalates can particularly occur in aqueous and air parts.

I.1. Properties - Phthalates – Bisphenol A The world phthalates production is estimated at 4 300 000 tons each year [27]. They are principally used as plasticizer to increase the flexibility and the workability of high molecular weight polymers. 90% of the production is applied for these characteristics. Their low melting point and high boiling point make of them also very useful as heat-transfer fluids and carriers. Phthalate proportion can attain up to 50% of the total weight. To be effective and useful in polymer, it must contain two types of structural parts, polar and apolar. The proportion of each part induces various physicochemical properties and in consequence their environmental fate. In addition, their chemical structure makes them hormone-like chemicals provoking endocrine disrupting effects. The structure of phthalate esters comprises an aromatic ring with two aliphatic side chains. More than 60 phthalates exists, but only 20 are industrially use. The polar part consists of the carbonyl group of carboxylic ester function and, to a lesser extent, of the aromatic ring. The non polar part is constituted by the aliphatic side chain of the ester (figure 1).

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4

Jean-Baptiste Baugros, Cécile Cren-Olivé and Marie-Florence Grenier-Loustalot

O O

R1

O R2 O

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Figure 1. Basic structure of phthalates. Phthalates esters are not chemically bond to the polymer matrix, majority of covalent bonds are formed and make the migration possible to the surface of the material [35]. Peijnenburg noticed that their migration capacity from the plastic matter varies in an inverse way to their molecular weight [27]. Even if this process occurs at very low rate, European and American concerns have risen on possible human health risks, particularly on children. Phthalates properties depend on the alkyl chain length. The water solubility, between 4200 to a value 1000 ng.m-3 quantified in apartments and homes [26, 35, 82, 83]. R O

OH

OH

O

O

O

O

O

O

O R of Basic structure phthalates

CO2

O OH

H2O

OH O

Mineralization

OH

R

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Figure 7. Global degradation pathway of phthalates in the environment [12, 17, 99]. The more critical point is that total concentrations of DEP, DBP, DEHP and BBP ranged from