DOCSLIB.ORG

Does External Exposure of Glycidol-Related Chemicals

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Does External Exposure of Glycidol-Related Chemicals toxics Communication Does External Exposure of Glycidol-Related Chemicals Influence the Forming of the Hemoglobin Adduct, N-(2,3-dihydroxypropyl)valine, as a Biomarker of Internal Exposure to Glycidol? Yuko Shimamura 1, Ryo Inagaki 1, Hiroshi Honda 2 and Shuichi Masuda 1,* 1 School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan; [email protected] (Y.S.); [email protected] (R.I.) 2 KAO Corporation, R&D Safety Science Research, 2606 Akabane, Ichikai-Machi, Haga-Gun, Tochigi 321-3497, Japan; [email protected] * Correspondence: [email protected]; Tel.: +81-54-264-5528 Received: 2 November 2020; Accepted: 11 December 2020; Published: 13 December 2020 Abstract: Glycidyl fatty acid esters (GE) are constituents of edible oils and fats, and are converted into glycidol, a genotoxic substance, in vivo. N-(2,3-dihydroxypropyl)valine (diHOPrVal), a hemoglobin adduct of glycidol, is used as a biomarker of glycidol and GE exposure. However, high background levels of diHOPrVal are not explained by daily dietary exposure to glycidol and GE. In the present study, several glycidol-related chemicals (glycidol, ( )-3-chloro-1,2-propanediol, glycidyl oleate, ± epichlorohydrin, propylene oxide, 1-bromopropane, allyl alcohol, fructose, and glyceraldehyde) that might be precursors of diHOPrVal, were administered to mice, and diHOPrVal formation from each substance was examined with LC-MS/MS. DiHOPrVal was detected in animals treated with glycidol and glycidyl oleate but not in mice treated with other chemicals (3-MCPD, epichlorohydrin, propylene oxide, 1-bromopropane, allyl alcohol, fructose, and glyceraldehyde). The amount of diHOPrVal per administered dose produced from other chemicals was negligible compared to the amounts associated with dietary glycidol and GE. The present study provides important knowledge for exploring other sources for internal exposure to glycidol. Keywords: glycidol; glycidyl fatty acid esters; Hb adduct; N-(2.3-dihydroxypropyl)valine 1. Introduction Glycidyl fatty acid esters (GE) are process contaminants, formed in a deodorization process under high-temperature conditions during the production of edible oils. Diacylglycerol oil was found to contain GE at considerably higher levels than other commercial edible oils. GEs were also formed in heat treatment of saltwater fish, meat patties, etc., especially at high temperature using a charcoal grill [1,2]. Furthermore, the formation of GE can occur in all refined edible oils and processed foods made using these oils [3,4], infant formula [5], baby foods [6], etc. GE are degraded in vivo by lipase to produce glycidol (2,3-epoxy-1-propanol), a reactive epoxide. Glycidol is a confirmed rodent carcinogen in a National Toxicology Program (NTP) study [7]. The genotoxicity is well characterized in vitro [8,9] and in vivo [10]. Human exposure is a concern because glycidol would be produced from dietary GE. Hemoglobin adducts are used as biomarkers for evaluating long-term exposure to various reactive chemicals. N-(2,3-dihydroxypropyl)valine (diHOPrVal) is a hemoglobin adduct of glycidol and is used as a marker for internal exposure to glycidol [11–14]. A total of eleven healthy participants consumed a daily portion of about 36 g of commercially available palm fat (8.7 mg glycidol/kg) over Toxics 2020, 8, 119; doi:10.3390/toxics8040119 www.mdpi.com/journal/toxics Toxics 2020, 8, x FOR PEER REVIEW 2 of 9 Toxics 2020, 8, 119 2 of 9 consumed a daily portion of about 36 g of commercially available palm fat (8.7 mg glycidol/kg) over 4 weeks. The mean daily glycidol exposure, as estimated from the adduct levels of the participants 4before weeks. the The intervention mean daily period glycidol (background exposure, levels as estimated of diHOPrVal), from the was adduct 0.94 levels µg/kg of body the participantsweight [15]. beforeAdditionally, the intervention diHOPrVal period levels (background were used levelsto estimate of diHOPrVal), a continuous was exposure 0.94 µg/kg of body1.4 μg/kg/day weight [15 of]. Additionally,glycidol in 50 diHOPrValchildren aged levels approximately were used to12 estimate years old a [16]. continuous These values exposure are ofsignificantly 1.4 µg/kg/ dayhigher of glycidolthan the in European 50 children Food aged Safety approximately Authority 12estimates years old of [ 16intake]. These for valuesadults areand significantly children. One higher possible than thereason European for this Food discrepancy Safety Authority is exposure estimates to other of chemicals intake for that adults form and diHOPrVal. children. One possible reason for thisTheoretically, discrepancy diHOPrVal is exposure might to other originate chemicals from that other form precu diHOPrVal.rsors (Figure 1). One possibility is the foodTheoretically, contaminant diHOPrVal 3-monochloropropane might originate from-1,2-diol other (3 precursors-MCPD), which (Figure often1). One forms possibility in foods is the in foodparallel contaminant with glycidol 3-monochloropropane-1,2-diol [17]. GE are also formed from (3-MCPD), 3-MCPD which esters often in neutral, forms acidic, in foods and in parallelalkaline withmedia glycidol [18]. Furthermore, [17]. GE are also ally formedl alcohol from can 3-MCPD theoretically esters in be neutral, converted acidic, to and diHOPrVal, alkaline media and [18the]. Furthermore,glyceraldehyde allyl hemoglobin alcohol can adduct theoretically might be be converted converted to to diHOPrVal diHOPrVal, under and reducing the glyceraldehyde conditions hemoglobin[19]. Hondaadduct et al. mightreported be converteda positive to correlation diHOPrVal between under reducing intake conditionsof one food [19 ].item Honda (western et al. reportedconfection a positiveery) and correlation diHOPrVal between levels among intake ofthe one 70 foodfood item items (western and 97 confectionery)nutrients in a andfood diHOPrVal frequency levelsquestionnaire among the[12], 70 although food items Aasa and et al. 97 did nutrients not confirm in a foodthe importance frequency of questionnaire sweets intake [12 [16].], although Fructose Aasain western et al. did confectionery not confirm theis importancemetabolized of to sweets glyceraldehyde intake [16]. Fructose[20]. Occupational in western confectioneryexposure to isepichlorohydrin metabolized to may glyceraldehyde also result in [ 20diHOPrVal]. Occupational [21]. Ishidao exposure et al. to reported epichlorohydrin glycidol in may urine also samples result inof diHOPrValrats that were [21]. exposed Ishidao to et al.1-bromopropane reported glycidol and inassumed urine samples that propylene of rats that oxide were is exposeda possible to 1-bromopropaneintermediate between and assumed 1-bromopropane that propylene and oxideglycidol is a possible[22]. diHOPrVal intermediate levels between in smokers 1-bromopropane are higher andthan glycidol those in [ 22non].- diHOPrValsmokers [23]. levels On inthe smokers other hand, are higher Eckert than et al. those and inAndreoli non-smokers et al. reported [23]. On that the otherlevels hand, of 2,3- Eckertdihydroxypropyl et al. and Andreoli mercapturic et al. acid, reported a urinary that biomarker levels of 2,3-dihydroxypropyl of glycidol, were correlated mercapturic with acid,urinary a urinary creatinine biomarker but not with of glycidol, smoking were status correlated [24,25]. It with is possible urinary that creatinine chemicals but other not with than smoking glycidol statusmight [24affect,25]. Itthe is possibleformation that of chemicals diHOPrVal. other Although than glycidol several might studies affect the discussed formation other of diHOPrVal. possible Althoughprecursors several of glycidol, studies experimental discussed other verification possible has precursors not been of provided. glycidol, experimentalThe aim of this verification study was has to notexamine been provided.whether Theexternal aim of exposure this study to was glycidol to examine-related whether chemicals external (3 exposure-MCPD, toepichlorohydrin, glycidol-related chemicalspropylene (3-MCPD, oxide, 1-bromopropane, epichlorohydrin, allyl propylene alcohol, oxide, fructose, 1-bromopropane, and glyceraldehyde) allyl alcohol, affect fructose,s levels and of glyceraldehyde)diHOPrVal in vivo affects using levels mice of diHOPrVal. In addition,in vivoadductsusing of mice. epichlorohydrin In addition,adducts and glyceraldehyde of epichlorohydrin were andevaluated. glyceraldehyde were evaluated. FigureFigure 1.1. Examples of possible precursors toto NN-(2,3-dihydroxypropyl)valine-(2,3-dihydroxypropyl)valine cf.cf. [[1616,19].,19]. 2. Materials and Methods 2. Materials and Methods 2.1. Chemicals 2.1. Chemicals Fluorescein isothiocyanate (FITC), glycidol, ( )-3-chloro-1,2-propanediol (3-MCPD) (purity 98.0%), ± and glycidylFluorescein oleate isothiocyanate (purity 98.0%) were(FITC), obtained glycidol, from (±) Sigma-Aldrich-3-chloro-1,2-propanediol (St Louis, MO). (3 Epichlorohydrin,-MCPD) (purity propylene98.0%), and oxide, glycidyl 1-bromopropane, oleate (purity allyl 98.0%) alcohol, were D(-)-fructose, obtained andfrom DL-glyceraldehyde Sigma-Aldrich (St were Louis, obtained MO). Epichlorohydrin, propylene oxide, 1-bromopropane, allyl alcohol, D(-)-13fructose, and DL- from FUJIFILM Wako Pure Chemical Industries Ltd. (Osaka, Japan). L-Valine-( C5) (purity 98.0%) glyceraldehyde were obtained from FUJIFILM Wako Pure Chemical Industries13 Ltd. (Osaka, Japan). used for the synthesis of the internal standard N-(2,3-dihydroxypropyl)-( C5)valine,
Load more

Recommended publications
  • The Utilization of Ti-SBA-15 Catalyst in the Epoxidation of Allylic Alcohols
    Reac Kinet Mech Cat (2012) 105:451–468 DOI 10.1007/s11144-011-0405-1 The utilization of Ti-SBA-15 catalyst in the epoxidation of allylic alcohols Agnieszka Wro´blewska • Edyta Makuch Received: 17 August 2011 / Accepted: 16 November 2011 / Published online: 2 December 2011 Ó The Author(s) 2011. This article is published with open access at Springerlink.com Abstract Ti-SBA-15, one of the latest titanium silicalite catalysts, has been pre- pared according to the literature by the direct hydrothermal synthesis using Pluronic 123 as structure-directing agent. The characterization of the catalyst was performed by means of the following methods: XRD, IR, UV–Vis, X-ray microanalysis and SEM. The catalytic properties of the Ti-SBA-15 catalyst have been tested in the epoxidation of allyl alcohol, methallyl alcohol, crotyl alcohol and 1-butene-3-ol with hydrogen peroxide. The process has been described by the following main functions: the selectivity to epoxide compound in relation to allylic compound consumed and the conversion of allylic compound. Keywords Ti-SBA-15 Á Allylic compounds Á Epoxide compounds Á Liquid-phase epoxidation Á Hydrogen peroxide Mathematics Subject Classification (2000) 32 Á 46 Á 92 JEL Classification I23 Á L65 Introduction Zeolites with titanium atoms in the structure have wide applications in oxidation processes (especially in epoxidation processes) which are carried out in the presence of hydrogen peroxide (oxidizing agent). To the group of these zeolites belong TS-1 and TS-2 catalysts—the first titanium silicalite catalysts [1, 2]. TS-1 and TS-2 are microporous materials with relatively small pore size (about 0.5 nm), which limits A.
    [Show full text]
  • A New Approach to Prepare Polyethylene Glycol Allyl Glycidyl Ether
    E3S Web of Conferences 267, 02004 (2021) https://doi.org/10.1051/e3sconf/202126702004 ICESCE 2021 A new approach to prepare Polyethylene Glycol Allyl Glycidyl Ether Huizhen Wang1*, Ruiyang Xie1, Mingjun Chen1*, Weihao Deng1, Kaixin Zhang2, Jiaqin Liu1 1School of Science, Xihua University, Chengdu 610039, China; 2Chengdu Jingyiqiang Environmental Protection Technology Co., Ltd. Abstract. The polyethylene glycol allyl glycidyl ether (PGAGE) is an important intermediate for preparing silicone softener that can be synthesized from allyl alcohol polyoxyethylene ether and epichlorohydrin (ECH). The performance parameters including the concentration of ECH, initial boron trifluoride diethyl etherate (BFEE) as well as CaCl2 quality were investigated respectively. The optimum process parameters which can get high capping and low by-product rate are as follows: the ECH concentration is 2.0 M, the initial BFEE concentration is 1.65mM, and the CaCl2 dosage is 1.65g/L. Under these conditions, the maximal yield can be improved to 91.36%, the percent of capping rate is higher than 98.16%, the residual concentration of F- is only 0.63 mg/L. concentrated basic solution, in which the total yield was between 90%~91% by Matsuoka et al. [10] also use the 1 Introduction two-step reaction to synthesize AGE based on the reaction Polyethylene glycol allyl glycidyl ether (PGAGE) and the of allyl alcohol with ECH using BFEE as the catalyst. allyl polyoxyethylene ether (APEG), tethering with both Their results demonstrated that the yield reaches 82% alkene and epoxy groups, are widely used as fabric under the following condition: n (ECH) : n (allyl alcohol): finishing agent [1-2] , reactive diluent [3] , cross-linking (catalysis) = 1: (1~3) : (0.01~0.002).
    [Show full text]
  • A New Coupling Process for Synthesis of Epichlorohydrin from Dichloropropanols
    2nd International Conference on Machinery, Materials Engineering, Chemical Engineering and Biotechnology (MMECEB 2015) A new coupling process for synthesis of epichlorohydrin from dichloropropanols Dawei Wu, Sumin Zhou* School of Chemical Engineering, Huaiyin Institute of Technology, Huaian 223005, China [email protected] Keywords: dichloropropanol, epichlorohydrin, tubular reactor, wiped film evaporation. Abstract. As an important material used in the production of epoxy resins, epichlorohydrin is usually derived from the saponification and cyclization of dichloropropanol in a tower reacting system. In order to reduce energy consumption and wastewater discharge, a new process of tubular reactor coupled with wiped film evaporation was adopt to produce epichlorohydrin. The effects of different technological parameters on the yield of the coupling process were investigated, such as reactants' molar ratio, reaction & evaporation temperature, residence time and so on. Results indicated that the use of coupling process will significantly reduce the material consumption and shorter the reaction time. This coupling process provided a useful suggestion for the design of the industrial plants. 1. Introduction Epichlorohydyin（ECH）, also known as 1-chloro-2, 3-epoxy propane, is an important chemical material, mainly used to synthesizing epoxy resin, chlorohydrins rubber, pesticide, plasticizer and so on [1]. The main method to produce ECH is high-temperature chlorination of propylene [2]. With the fast-development of biodiesel production, the use of glycerol for producing ECH [3-4] is going to mature and has become an important industrial technological process [5]. Although the difference raw materials were used, the processes also consist of two reaction steps as well. First step is the saponification and cyclization of dichloropropanol (DCP) to produce ECH.
    [Show full text]
  • Optimization of the Synthesis of Glycerol Derived Monoethers from Glycidol by Means of Heterogeneous Acid Catalysis
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Repositorio Universidad de Zaragoza molecules Article Optimization of the Synthesis of Glycerol Derived Monoethers from Glycidol by Means of Heterogeneous Acid Catalysis Elisabet Pires 1,2,* , José Ignacio García 1, Alejandro Leal-Duaso 1, José Antonio Mayoral 1,2, José Ignacio García-Peiro 2 and David Velázquez 2 1 Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-University of Zaragoza-Calle Pedro Cerbuna, 12, E-50009 Zaragoza, Spain; [email protected] (J.I.G.); [email protected] (A.L.-D.); [email protected] (J.A.M.) 2 Departmento de Química Orgánica, Facultad de Ciencias, University of Zaragoza, Calle Pedro Cerbuna, 12, E-50009 Zaragoza, Spain; [email protected] (J.I.G.-P.); [email protected] (D.V.) * Correspondence: [email protected]; Tel.: +34-876-553501 Received: 7 October 2018; Accepted: 3 November 2018; Published: 6 November 2018 Abstract: We present an efficient and green methodology for the synthesis of glycerol monoethers, starting from glycidol and different alcohols, by means of heterogeneous acid catalysis. A scope of Brønsted and Lewis acid catalysts were applied to the benchmark reaction of glycidol and methanol. The selected catalysts were cationic exchangers, such as Nafion NR50, Dowex 50WX2, Amberlyst 15 and K10-Montmorillonite, both in their protonic form and exchanged with Al(III), Zn(II) and Fe(III). Thus, total conversions were reached in short times by using 1 and 5% mol catalyst loading and room temperature, without the need for excess glycidol or the presence of a solvent.
    [Show full text]
  • Production of Glycidyl Compounds
    Office europeen des brevets (fi) Publication number : 0 491 529 A1 @ EUROPEAN PATENT APPLICATION @ Application number : 91311630.7 © Int. CI.5: C07D 301/28, C07D 303/24 (22) Date of filing : 13.12.91 (30) Priority : 18.12.90 GB 9027448 (72) Inventor : Thoseby, Michael Robert 29 De Freville Avenue Cambridge (GB) (43) Date of publication of application : Inventor : Rolfe, William Martin 24.06.92 Bulletin 92/26 42 Vetch Walk Haverhill, Suffolk (GB) (S) Designated Contracting States : CH DE ES FR GB IT LI NL (74) Representative : Sparrow, Kenneth D. et al CIBA-GEIGY PLC. Patent Department, Central Research, Hulley Road @ Applicant : CIBA-GEIGY AG Macclesfield, Cheshire SK10 2NX (GB) Klybeckstrasse 141 CH-4002 Basel (CH) (54) Production of glycidyl compounds. (57) A process for the production of a glycidyl ether of an alcohol, comprising reacting an alcohol with epichlorohydrin, in substantially the stoichiometric proportions required to pro- duce the 1:1 adduct, in the presence, as catal- yst, of a salt of perchloric acid or trifluoromethane sulphonic acid with a metal of Group IMA of the Periodic Table of Elements (according to the IUPAC 1970 convention) ; and then dehydrochlorinating the product so obtained. CM LU Jouve, 18, rue Saint-Denis, 75001 PARIS 1 EP 0 491 529 A1 2 The present invention relates to a process for the 100 parts by weight of the alcohol reactant. production of glycidyl compounds. The alcohol reactant may be a primary, secon- The addition reaction between epoxides and dary or tertiary alcohol. While monohydric alcohols alcohols, in the presence of a catalyst, to produce an may be used, e.g.
    [Show full text]
  • Gasket Chemical Services Guide
    Gasket Chemical Services Guide Revision: GSG-100 6490 Rev.(AA) • The information contained herein is general in nature and recommendations are valid only for Victaulic compounds. • Gasket compatibility is dependent upon a number of factors. Suitability for a particular application must be determined by a competent individual familiar with system-specific conditions. • Victaulic offers no warranties, expressed or implied, of a product in any application. Contact your Victaulic sales representative to ensure the best gasket is selected for a particular service. Failure to follow these instructions could cause system failure, resulting in serious personal injury and property damage. Rating Code Key 1 Most Applications 2 Limited Applications 3 Restricted Applications (Nitrile) (EPDM) Grade E (Silicone) GRADE L GRADE T GRADE A GRADE V GRADE O GRADE M (Neoprene) GRADE M2 --- Insufficient Data (White Nitrile) GRADE CHP-2 (Epichlorohydrin) (Fluoroelastomer) (Fluoroelastomer) (Halogenated Butyl) (Hydrogenated Nitrile) Chemical GRADE ST / H Abietic Acid --- --- --- --- --- --- --- --- --- --- Acetaldehyde 2 3 3 3 3 --- --- 2 --- 3 Acetamide 1 1 1 1 2 --- --- 2 --- 3 Acetanilide 1 3 3 3 1 --- --- 2 --- 3 Acetic Acid, 30% 1 2 2 2 1 --- 2 1 2 3 Acetic Acid, 5% 1 2 2 2 1 --- 2 1 1 3 Acetic Acid, Glacial 1 3 3 3 3 --- 3 2 3 3 Acetic Acid, Hot, High Pressure 3 3 3 3 3 --- 3 3 3 3 Acetic Anhydride 2 3 3 3 2 --- 3 3 --- 3 Acetoacetic Acid 1 3 3 3 1 --- --- 2 --- 3 Acetone 1 3 3 3 3 --- 3 3 3 3 Acetone Cyanohydrin 1 3 3 3 1 --- --- 2 --- 3 Acetonitrile 1 3 3 3 1 --- --- --- --- 3 Acetophenetidine 3 2 2 2 3 --- --- --- --- 1 Acetophenone 1 3 3 3 3 --- 3 3 --- 3 Acetotoluidide 3 2 2 2 3 --- --- --- --- 1 Acetyl Acetone 1 3 3 3 3 --- 3 3 --- 3 The data and recommendations presented are based upon the best information available resulting from a combination of Victaulic's field experience, laboratory testing and recommendations supplied by prime producers of basic copolymer materials.
    [Show full text]
  • The Selective Epoxidation of Allyl Alcohol to Glycidol
    THE SELECTIVE EPOXIDATION OF ALLYL ALCOHOL TO GLYCIDOL A THESIS SUBMITTED FOR THE DEGREE OF DOCTOR OF PHILOSOPHY Luke Martin Harvey B. Eng. (Newcastle), B. Sci. (Newcastle) Department of Chemical Engineering The University of Newcastle, Australia November 2020 This research was supported by an Australian Government Research Training Program (RTP) Scholarship STATEMENT OF ORIGINALITY I hereby certify that the work embodied in the thesis is my own work, conducted under normal supervision. The thesis contains no material which has been accepted, or is being examined, for the award of any other degree or diploma in any university or other tertiary institution and, to the best of my knowledge and belief, contains no material previously published or written by another person, except where due reference has been made. I give consent to the final version of my thesis being made available worldwide when deposited in the University’s Digital Repository, subject to the provisions of the Copyright Act 1968 and any approved embargo. Luke Harvey 25 November 2020 I ACKNOWLEDGMENT OF AUTHORSHIP I hereby certify that the work embodied in this thesis contains published paper/s/scholarly work of which I am a joint author. I have included as part of the thesis a written declaration endorsed in writing by my supervisor, attesting to my contribution to the joint publication/s/scholarly work. By signing below I confirm that Luke Martin Harvey contributed the design of the experimental program, conducted experiments, data analysis and scientific writing to the paper/ publication entitled “Influence of impurities on the epoxidation of allyl alcohol to glycidol with hydrogen peroxide over titanium silicate TS-1” and contributed the epoxidation chemistry portion of the experimentation and scientific writing to the paper/ publication entitled “Enhancing allyl alcohol selectivity in the catalytic conversion of glycerol; influence of product distribution on the subsequent epoxidation step”.
    [Show full text]
  • Alkaline-Based Catalysts for Glycerol Polymerization Reaction: a Review
    Preprints (www.preprints.org) | NOT PEER-REVIEWED | Posted: 26 July 2020 doi:10.20944/preprints202007.0649.v1 Peer-reviewed version available at Catalysts 2020, 10, 1021; doi:10.3390/catal10091021 Review Alkaline-based catalysts for glycerol polymerization reaction: a review Negisa Ebadipour1, Sébastien Paul1, Benjamin Katryniok1 and Franck Dumeignil1,* 1 Univ. Lille, CNRS, Centrale Lille, Univ. Artois, UMR 8181 – UCCS – Unité de Catalyse et Chimie du Solide, F-59000 Lille, France; [email protected] (N.E.); [email protected] (S.P.); [email protected] (B.K.) * Correspondence: [email protected]; Tel.: +33-(0)3-20-43-45-38 Abstract: Polyglycerols (PGs) are biocompatible and highly functional polyols with a wide range of applications, such as emulsifiers, stabilizers, antimicrobial agents, in many industries including cosmetics, food, plastic and biomedical. The demand increase for biobased PGs encourages researchers to develop new catalytic systems for glycerol polymerization. This review focuses on alkaline homogeneous and heterogeneous catalysts. The performances of the alkaline catalysts are compared in terms of conversion and selectivity, and their respective advantages and disadvantages are commented. While homogeneous catalysts exhibit a high catalytic activity, they cannot be recycled and reused, whereas solid catalysts can be partially recycled. The key issue for heterogenous catalytic systems, which is unsolved so far, is linked to their instability due to partial dissolution in the reaction medium. Further, this paper also reviews the proposed mechanisms of glycerol polymerization over alkaline-based catalysts and discuss the various operating conditions with an impact on the performances. More particularly, temperature and amount of catalyst proved to have a significant influence on glycerol conversion and on its polymerization extent.
    [Show full text]
  • Comparisons of Epoxy Technology for Protective Coatings and Linings In
    ComparisonsComparisons ofof EpoxyEpoxy TechnologyTechnology forfor ProtectiveProtective CoatingsCoatings andand LiningsLinings inin WastewaterWastewater FacilitiesFacilities By John D. Durig, General Polymers, Cincinnati, Ohio, USA Aeration tank at a wastewater plant. Bis F epoxy resin with an aliphatic or a cycloaliphatic amine curing agent is appropriate. Editor’s Note: This article was first presented at SSPC (Photos courtesy of the author) 99, The Industrial Protective Coatings Conference and Exhibit, November 14-18, 1999, in Houston, TX, USA, and published in The Proceedings of the Seminars, SSPC 99-14, pp. 31-37. poxy technology and methods of curing and Epoxy Resin Technology E reacting with amine-based hardeners have There are three types of epoxy resins that find application continued to evolve since the first epoxy patents were is- in wastewater treatment facilities: bisphenol A, bisphenol sued in the 1930s. The possible reactions combined with F, and novolac resins. These resins all result from reac- wide-ranging formulation additives have resulted in a myri- tions of epichlorohydrin with phenolic compounds. The ad of products that can easily confuse decision makers type and number of phenolic groups determine both when it comes to product selection. Adding to the confu- physical and performance properties of the cured resin. sion is the wide range of environmental factors that must be considered when choosing a protective coating system. Bisphenol A Resin Structure This article will identify the primary differences be- Bisphenol A is a reaction product of phenol and acetone. tween three types of epoxies and four types of amine- Bisphenol A is reacted with epichlorohydrin to form based hardeners typically used in coatings for wastewater diglycidylether bisphenol A resin or DGEBA.
    [Show full text]
  • The Production of Epichlorohydrin from Glycerol. a Bachelor Integration Project for Delfzijl’S Chempark
    The production of epichlorohydrin from glycerol. A Bachelor Integration Project for Delfzijl’s Chempark Ruurd Feikes van der Heide University of Groningen Faculty of Science and Engineering IE&M Bachelor Thesis Supervisor 1: prof. Dr. Ir. HJ (Erik) Heeres Supervisor 2: Dr. Ing. H. Kloosterman Syncom supervisor: Dr. Ir. Andre Heeres June 2018 Pelsterstraat 32 9711 KM Groningen (06) 13787270 [email protected] student number 2674122 1 Table of content Introduction (RDP) -Problem context -Stakeholder analysis -System description -Goal statement -Design goal -Scope -Research questions -Cycle choice Abstract Backgrounds -Glycerol -Epichlorohydrin Benchmark -Propylene into epichlorohydrin, via allyl chloride -Allyl chloride to epichlorohydrin -TRL Innovation - Glycerol into epichlorohydrin -Hydrochlorination -Hexanoic acid -Acetic acid -Dehydrochlorination -TRL Cost analysis -Hexanoic acid -Solid oxide Discussion and conclusions References Appendix 2 Problem context The city of Delfzijl (Netherlands) has a chemical park with multiple factories present. The companies at the chemical park have interrelationships with each other which results that if a few of them stop producing products, the other companies will find problems in their own existence. The committee Willems started an investigation how the chemical park should optimize its competitiveness among the business environment nowadays. Willems used to be a high ranked employee of Shell before leaving the company. The committee stated that if the companies on the park want to stay in business, changes within production methods have to be made. A more sustainable production method where green raw materials like biomass are converted into valuable products is the solution to stay competitive. Prof. Dr. Ir.
    [Show full text]
  • Internal Doses of Glycidol in Children and Estimation of Associated Cancer Risk
    toxics Article Internal Doses of Glycidol in Children and Estimation of Associated Cancer Risk Jenny Aasa 1, Efstathios Vryonidis 1, Lilianne Abramsson-Zetterberg 2 and Margareta Törnqvist 1,* 1 Department of Environmental Science and Analytical Chemistry, Stockholm University, 106 91 Stockholm, Sweden; [email protected] (J.A.); [email protected] (E.V.) 2 National Food Agency, 751 26 Uppsala, Sweden; [email protected] * Correspondence: [email protected]; Tel.: +46-816-3769 Received: 20 December 2018; Accepted: 29 January 2019; Published: 1 February 2019 Abstract: The general population is exposed to the genotoxic carcinogen glycidol via food containing refined edible oils where glycidol is present in the form of fatty acid esters. In this study, internal (in vivo) doses of glycidol were determined in a cohort of 50 children and in a reference group of 12 adults (non-smokers and smokers). The lifetime in vivo doses and intakes of glycidol were calculated from the levels of the hemoglobin (Hb) adduct N-(2,3-dihydroxypropyl)valine in blood samples from the subjects, demonstrating a fivefold variation between the children. The estimated mean intake (1.4 µg/kg/day) was about two times higher, compared to the estimated intake for children by the European Food Safety Authority. The data from adults indicate that the non-smoking and smoking subjects are exposed to about the same or higher levels compared to the children, respectively. The estimated lifetime cancer risk (200/105) was calculated by a multiplicative risk model from the lifetime in vivo doses of glycidol in the children, and exceeds what is considered to be an acceptable cancer risk.
    [Show full text]
  • Environmental Health Criteria 33 EPICHLOROHYDRIN
    Environmental Health Criteria 33 EPICHLOROHYDRIN Please note that the layout and pagination of this web version are not identical with the printed version. Epichlorohydrin (EHC 33, 1984) INTERNATIONAL PROGRAMME ON CHEMICAL SAFETY ENVIRONMENTAL HEALTH CRITERIA 33 EPICHLOROHYDRIN This report contains the collective views of an international group of experts and does not necessarily represent the decisions or the stated policy of the United Nations Environment Programme, the International Labour Organisation, or the World Health Organization. Published under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation, and the World Health Organization World Health Orgnization Geneva, 1984 The International Programme on Chemical Safety (IPCS) is a joint venture of the United Nations Environment Programme, the International Labour Organisation, and the World Health Organization. The main objective of the IPCS is to carry out and disseminate evaluations of the effects of chemicals on human health and the quality of the environment. Supporting activities include the development of epidemiological, experimental laboratory, and risk-assessment methods that could produce internationally comparable results, and the development of manpower in the field of toxicology. Other activities carried out by the IPCS include the development of know-how for coping with chemical accidents, coordination of laboratory testing and epidemiological studies, and promotion of research on the mechanisms of the biological action of chemicals. ISBN 92 4 154093 1 The World Health Organization welcomes requests for permission to reproduce or translate its publications, in part or in full. Applications and enquiries should be addressed to the Office of Publications, World Health Organization, Geneva, Switzerland, which will be glad to provide the latest information on any changes made to the text, plans for new editions, and reprints and translations already available.
    [Show full text]