HS-SPME-GC-MS analysis of antioxidant degradation ...

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Oct 8, 2012 - (VI), 3-(3,5-di-tert-butyl-4-hydroxyphenyl)methylpropanoat (IX), 3-(3,5-di-tert-butyl-4-. hydroxyphenyl)pr...

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This article was downloaded by: [62.198.228.20] On: 15 December 2012, At: 02:22 Publisher: Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK

International Journal of Environmental Analytical Chemistry Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/geac20

HS-SPME-GC-MS analysis of antioxidant degradation products migrating to drinking water from PE materials and PEX pipes a

a

Hans-Christian Holten Lützhøft , Christopher Kevin Waul , a

a

Henrik Rasmus Andersen , Bozena Seredynska-Sobecka , Hans a

a

a

Mosbæk , Nina Christensen , Mikael Emil Olsson & Erik Arvin

a

a

Department of Environmental Engineering, Technical University of Denmark (DTU), Miljøvej 113, 2800 Kgs. Lyngby, Denmark Version of record first published: 08 Oct 2012.

To cite this article: Hans-Christian Holten Lützhøft, Christopher Kevin Waul, Henrik Rasmus Andersen, Bozena Seredynska-Sobecka, Hans Mosbæk, Nina Christensen, Mikael Emil Olsson & Erik Arvin (2012): HS-SPME-GC-MS analysis of antioxidant degradation products migrating to drinking water from PE materials and PEX pipes, International Journal of Environmental Analytical Chemistry, DOI:10.1080/03067319.2012.727805 To link to this article: http://dx.doi.org/10.1080/03067319.2012.727805

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Intern. J. Environ. Anal. Chem. 2012, 1–20, iFirst

HS-SPME-GC-MS analysis of antioxidant degradation products migrating to drinking water from PE materials and PEX pipes Hans-Christian Holten Lu¨tzhøft*, Christopher Kevin Waul, Henrik Rasmus Andersen, Bozena Seredynska-Sobecka, Hans Mosbæk, Nina Christensen, Mikael Emil Olsson and Erik Arvin

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Department of Environmental Engineering, Technical University of Denmark (DTU), Miljøvej 113, 2800 Kgs. Lyngby, Denmark (Received 9 August 2011; final version received 9 August 2012) Polyethylene (PE) and cross-linked polyethylene (PEX) pipes are frequently used in water supply systems. Such pipes contain added antioxidants with phenolic structures, e.g. Irgafos 168, Irganox 1010 and 1076, in order to improve durability. However, phenol, ketone and quinone antioxidant degradation products may leach and enter drinking water. The aim of this investigation was to develop a method for measuring these degradation products with a performance meeting the drinking water quality criteria of 20 mg L1. Using headspace solid phase microextraction coupled to a gas chromatograph with a mass spectrometer, a method was established revealing limits of detection and quantification less than 0.4 and 1 mg L1 respectively. The method was applied to migration experiments for two PEX pipes and one PE material, quantifying the release of two degradation products. Highest concentrations were observed for 2,6-di-tert-butyl-p-benzoquinone which in one of the two pipes was found in concentrations of 18–57 mg L1 in each of eight consecutive release experiments. Keywords: SPME-GC-MS; antioxidants; cross linked polyethylene pipes; degradation products; drinking water; water supply

1. Introduction Polyethylene (PE) pipes are now used extensively for replacing cast iron or concrete pipes in drinking water supply systems. These plastic pipes have favourable mechanical properties, low permeability to external contaminants and can be easily manufactured [1]. During the manufacturing process antioxidants are added to prevent oxidation of the polymer during manufacture and use [2]. Antioxidants such as Irgafos 168, Irganox 1010 and 1076 are typically bulky compounds with hindered phenolic structures (see Figure 1). The antioxidants are normally added to the polymers at a concentration of 0.05–1% w/w [3]. As is also seen from the antioxidant structures, degradation to lower molecular weight phenols, ketones and quinones such as butylated hydroxytoluene (BHT), 2,6-di-tert-butyl-p-benzoquinone (III), 3,5-di-tert-butyl-4-hydroxybenzaldehyde (VI), 3-(3,5-di-tert-butyl-4-hydroxyphenyl)methylpropanoat (IX), 3-(3,5-di-tert-butyl-4hydroxyphenyl)propanoic acid (X) and 2-tert-butylphenol (XIV) is possible, which to some extent also have antioxidant effects (see Table 1 for structures and laboratory IDs). *Corresponding author. Email: [email protected] ISSN 0306–7319 print/ISSN 1029–0397 online ß 2012 Taylor & Francis http://dx.doi.org/10.1080/03067319.2012.727805 http://www.tandfonline.com

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H.-C.H. Lu¨tzhøft et al. Irgafos 168

Structure

H3C

CH3

H 3C

H3C

Irganox 1010 H3C

CH3 CH3

H3C O

H3C

O

H3C

CH3

CH3

H3C

H3C CH3 CH3

CH3

O

CH3 H3C

CH3 CH3

CH3

H3C HO

O

OH

O

CH3

O

O CH3

H3C

CH3 CH3

CH3

P

H3C

CH3 OH H3C

Irganox 1076

O

O

H3C

CH3

H3C

O

H3C

O

H3C

O

CH3

H3C OH CH3

O

H3C H3C

CH3

H3C

CH3

H3C CH OH H C CH3 3 3

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Name

CAS#

Tris(2,4-ditert-

Pentaerythritol tetrakis(3-

Octadecyl 3-(3,5-di-tert-butyl-4-

butylphenyl)

(3,5-di-tert-butyl-4-

hydroxyphenyl)propionate

phosphate

hydroxyphenyl)propionate)

31570-04-4

6683-19-8

2082-79-3

MW , g m ole–1

6 4 6 .9 2

1 1 7 7 .6 3

5 3 0 .8 6

S, µg L–1

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