Occurrence of Bisphenol A Diglycidyl Ethers (BADGEs) and Novolac

Apr 29, 2015 - Center for Environmental Security, The Biodesign Institute, Global Security Initiative, Arizona State University, Tempe, Arizona 85287,...
0 downloads 0 Views 594KB Size
Subscriber access provided by NEW YORK UNIV

Article

Occurrence of bisphenol A diglycidyl ethers (BADGEs) and novolac glycidyl ethers (NOGEs) in archived biosolids from the U.S. EPA’s Targeted National Sewage Sludge Survey Jingchuan Xue, Arjun K. Venkatesan, Qian Wu, Rolf U Halden, and Kurunthachalam Kannan Environ. Sci. Technol., Just Accepted Manuscript • DOI: 10.1021/acs.est.5b01115 • Publication Date (Web): 29 Apr 2015 Downloaded from http://pubs.acs.org on May 12, 2015

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

Environmental Science & Technology is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 25

Environmental Science & Technology

1

Occurrence of bisphenol A diglycidyl ethers (BADGEs) and novolac

2

glycidyl ethers (NOGEs) in archived biosolids from the U.S. EPA’s

3

Targeted National Sewage Sludge Survey

4 5 6

Jingchuan Xue1; Arjun K. Venkatesan2, Qian Wu1, Rolf U. Halden2, Kurunthachalam Kannan1,3,*

7 1

10

Wadsworth Center, New York State Department of Health, and Department of Environmental Health Sciences, School of Public Health, State University of New York at Albany, Albany, NY 12201, United States

11

2

8 9

12

Center for Environmental Security, The Biodesign Institute, Arizona State University, Tempe, AZ 85287, United States

13

3

14

Biochemistry Department, Faculty of Science and Experimental Biochemistry Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah, Saudi Arabia

15 16 17

*Corresponding author: K. Kannan, [email protected]

18

Wadsworth Center

19

Empire State Plaza, P.O. Box 509

20

Albany, NY 12201-0509

21

Tel: +1-518-474-0015

22

Fax: +1-518-473-2895

23

E-mail: [email protected]

24 25 26

Submission to: ES&T

1 ACS Paragon Plus Environment

Environmental Science & Technology

27

Toc art

28

29

30

31

32

33

34

35

Abstract

36

Epoxy resins incorporating bisphenol A diglycidyl ether (BADGE) and novolac glycidyl

37

ether (NOGE) are used in a wide range of applications, including adhesives, structural and

38

electrical laminates. However, little is known about the occurrence of BADGE, NOGE, and

39

their derivatives in the environment. Using liquid chromatography-tandem mass spectrometry,

40

BADGE, bisphenol F glycidyl ether (BFDGE), 3-ring NOGE, and eight of their derivatives

41

(BADGE‧2 H2O, BADGE‧H2O, BADGE‧HCl‧H2O, BADGE‧2 HCl, BADGE‧HCl,

42

BFDGE‧2 H2O, and BFDGE‧2 HCl) were determined in archived biosolid samples collected

43

from 68 wastewater treatment plants (WWTPs) from the northeastern, midwestern, western,

44

and southern regions of the USA. BADGE‧2 H2O was the most frequently detected

45

(DR=99%) and the most abundant compound found (median: 93.6 ng/g dry weight [dw]) in

46

this family. The highest total concentrations of target chemicals, ranging from 83.6 to 2490 2 ACS Paragon Plus Environment

Page 2 of 25

Page 3 of 25

Environmental Science & Technology

47

ng/g dw, were found in biosolids collected from the northeastern United States. The sum of

48

geometric mean (GM) concentration of BADGE, NOGE and their derivatives in biosolids

49

increased with the treatment capacity of WWTPs. Based on the measured concentrations in

50

biosolids and predicted mass in wastewater, it was estimated that approximately 3.5% of the

51

total production of BADGEs was emitted through WWTP discharges.

52 53

Key words: biosolids; sewage sludge; BADGE; BFDGE; NOGE; epoxy resins

54

55

Introduction

56

Bisphenol A diglycidyl ether [BADGE or 2,2-bis(4-(2,3-epoxypropyl)phenyl) propane] is a

57

synthetic industrial compound obtained by a condensation reaction between 2 moles of

58

epichlorohydrin and 1 mole of 2, 2-bis(4-hydroxyphenol) propane (bisphenol A or BPA) in

59

the presence of sodium hydroxide.1 BADGE-based epoxy resins account for 90-95% of

60

epoxy resin production in the USA.2 Similarly, novolac glycidyl ether (NOGE)-based resin, a

61

complex mixture containing compounds with more than two aromatic rings and glycidyl

62

groups, is produced from the reaction between novolac and epichlorohydrin.3 The two-ring

63

(2R-) product of NOGE is referred to as bisphenol F diglycidyl ether (BFDGE). Other NOGE

64

analogues with 3R- to 8R- products are also used in commerce.3 Similarly, formulations

65

containing mixtures of more than one type of epoxy resins (e.g., blends of BADGE and

66

BFDGE resins) are also available in commerce.1

3 ACS Paragon Plus Environment

Environmental Science & Technology

BADGE and NOGE are categorized as “high production volume (HPV) chemicals”

67 68

by the United States Environmental Protection Agency (EPA). The combined production and

69

import volume of BADGE based epoxy resin (CAS No. 25068-38-6) was in the range of 1 to

70

10 million pounds, and that of BFDGE based epoxy resin (CAS No. 28064-14-4) was

71

~500,000 pounds in the USA in 2006.4 Polymers based on BADGE and NOGE are the

72

dominant type of epoxy resins used in internal coatings of food and beverage cans, lids of

73

glass jars, wine storage vats, and water pipes.5-7 BADGE and NOGE are also used as

74

additives for the elimination of surplus hydrochloric acid in the production of polyvinyl

75

chloride (PVC) organosols.3, 8 In addition, epoxy resins are widely used in electrical,

76

electronic, automotive and construction industries, among others.1 BADGE has a low water solubility (10. Method LOQs were

194

determined in the same manner with the post-matrix spiked (nine- to eleven-point) calibration

195

curves. As a check for instrumentation drift in response factors, a midpoint calibration

196

standard was injected after every 6 samples. To check for carryover of target chemicals from

197

sample to sample, a pure solvent (methanol) was injected after every 6 samples.

198

Several procedural blanks were analyzed with each batch of samples to determine the

199

contamination arising from laboratory materials and solvents. Throughout the analysis, six

200

sludge samples were selected randomly for pre-extraction matrix spike (MS) (two for every

201

25 samples) by spiking 40 ng of target analytes and passing them through the entire analytical

202

procedure.

203

Data Analysis

204

For the calculation of geometric mean (GM), arithmetic mean, and median of study results,

205

concentrations below the LOQ were substituted with a value equal to half the LOQ. Data

206

were acquired with Analyst software version 1.4.1 (Applied Biosystems, Foster City, CA).

207

The concentrations in biosolids are presented on a dry weight (dw) basis, unless stated

208

otherwise. Microsoft Excel 2007 was used for the statistical analysis. The statistics software

209

R v.3.1.0 was employed for Spearman correlation analysis. Statistical significance was set at

210

p