Identification and quantitation of dinaphthylsulfones in particulate matter of the Elbe river, Germany: Part VI of organic compounds as contaminants of the Elbe river and its tributaries

Article abstract of DOI:10.1016/S0045-6535(03)00095-X

Gas chromatographic-mass spectrometric (GC/MS) analysis of particulate matter of the Elbe river and its tributaries Havel, Spree and Mulde revealed a group of three dinaphthylsulfone isomers as sedimentary and suspended particulate matter (SPM) contaminants. The mass spectra of dinaphthylsulfones are characterized by the molecular ion (m/z 318), and the naphthyl fragment ion m/z 127. Losses of HSO₂ and C₁₀H₇O from the molecular ion lead to different mass spectra for each isomer. The gas phase infrared spectra exhibit isomer specific bands in the spectral region between 900 and 700 wave numbers. A synthetic mixture of dinaphthylsulfones was used for isomer identification and the assignment of the gas chromatographic retention behaviour of the dinaphthylsulfone isomers. Quantitative GC/MS analysis of dinaphthylsulfones in 44 sediment and SPM samples provided comprehensive information on the overall distribution and distinct sources of dinaphthylsulfones in the Elbe river drainage system. The results indicate emissions of these compounds over prolonged times and their environmental stability in anaerobic sediments.

Full text of DOI:10.1016/S0045-6535(03)00095-X

Chemosphere 51 (2003) 973–981
www.elsevier.com/locate/chemosphere
Identification and quantitation of dinaphthylsulfones
in particulate matter of the Elbe river, Germany q
Part VI of organic compounds as contaminants of
the Elbe river and its tributaries
*
Jan Schwarzbauer , Stephan Franke
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Received 16 April 2002; received in revised form 14 January 2003; accepted 14 January 2003
Abstract
Gas chromatographic–mass spectrometric (GC/MS) analysis of particulate matter of the Elbe river and its tribu-
taries Havel, Spree and Mulde revealed a group of three dinaphthylsulfone isomers as sedimentary and suspended
particulate matter (SPM) contaminants. The mass spectra of dinaphthylsulfones are characterized by the molecular ion
(m=z 318), and the naphthyl fragment ion m=z 127. Losses of HSO2 and C10H7O from the molecular ion lead to different
mass spectra for each isomer. The gas phase infrared spectra exhibit isomer specific bands in the spectral region between
900 and 700 wave numbers. A synthetic mixture of dinaphthylsulfones was used for isomer identification and the as-
signment of the gas chromatographic retention behaviour of the dinaphthylsulfone isomers. Quantitative GC/MS
analysis of dinaphthylsulfones in 44 sediment and SPM samples provided comprehensive information on the overall
distribution and distinct sources of dinaphthylsulfones in the Elbe river drainage system. The results indicate emissions
of these compounds over prolonged times and their environmental stability in anaerobic sediments.
Ó 2003 Elsevier Science Ltd. All rights reserved.
Keywords: Dinaphthylsulfones; Riverine organic contaminants; GC–MS analysis; Mass spectra; FTIR-spectra; Riverine particulate
matter
1. Introduction
the riverine particulate matter of the Elbe river revealed
a wide variety of lipophilic organic substances. In ad-
dition to biogenic compounds and their diagenetic
products a significant proportion of the compounds was
attributed to anthropogenic point and non-point sour-
ces. Organic substances as contaminants of the Elbe
river water were reported in detail previously (Franke
et al., 1995). Various groups of man-made substances
were detected in the suspended particulate matter (SPM)
as well especially in surface sediment layers. These xeno-
biotic compounds include alkyl sulfonic acid aryl esters
(Franke et al., 1998), chlorinated di- and triphenyl-
methanes (Schwarzbauer et al., 1999), brominated and
chlorinated aromatics, and pesticides (Schwarzbauer
et al., 2001). This paper describes the identification and
Investigations by gas chromatographic–mass spec-
trometric (GC/MS) analyses on the contamination of
q Part V: Schwarzbauer, J., Ricking, M., Franke, S., Francke,
W., 2001. Environmental Science and Technology 35, 4015–
4025.
* Corresponding author. Present address: Institute of Geol-
ogy and Geochemistry of Petroleum and Coal, Aachen
University of Technology, Lochnerstr. 4-20, 52056 Aachen,
Germany. Tel.: +49-241-805-750; fax: +49-241-888-8152.
E-mail address: schwarzbauer@lek.rwth-aachen.de (J.
Schwarzbauer).
0045-6535/03/$ - see front matter Ó 2003 Elsevier Science Ltd. All rights reserved.
doi:10.1016/S0045-6535(03)00095-X

974
J. Schwarzbauer, S. Franke / Chemosphere 51 (2003) 973–981
quantitation of dinaphthylsulfones in sedimentary and
SPM of the Elbe, Mulde, Spree and Havel rivers.
Dinaphthylsulfones were described formerly as ri-
verine and waste water contaminants. In sediments of
the Delaware river three isomers were detected (Sheldon
and Hites, 1978). Furthermore, dinaphthylsulfones were
identified in tannery effluents and tar balls associated
with industrial waste water emissions (Jungclaus et al.,
1978; Thruiston and McGuire, 1981). Neither the as-
signment of isomers nor quantitative data were obtained
in these studies.
river was collected in sediment traps during 1995 (ES1–
ES10). Additional sampling details were given elsewhere
(Franke et al., 1998; Schwarzbauer et al., 1999, 2001).
With the exception of the older samples from the
Hamburg Harbour all sediment samples were analysed
within a few weeks after sampling. Hamburg Harbour
samples collected in 1987/1988 were stored at 4 °C in
darkness under anaerobic conditions prior to the ana-
lytical procedure applied in 1994.
2.2. Extraction and fractionation
Hence, to our knowledge this is the first report of
dinaphthylsulfones in the riverine environment present-
ing not only quantitative data but also separately for
each positional isomer.
Extraction of organic compounds from the sample
materials, fractionation of the extracts by column ch-
romatography, and the determination of dry weights
have been described in detail previously (Franke et al.,
1998). Data on concentrations calculated from quanti-
tative analyses consider recoveries and dry weights.
Recoveries were determined twice as follows: Thor-
oughly pre-extracted, wet sediments in which dinaph-
thylsulfones were not longer detectable were spiked with
a mixture of synthetic dinaphthylsulfones (50 ll of a
methanolic solution containing 8.6 and 9.1 ng/ll of the
1,2- and 2,2-isomers, respectively). To thoroughly mix
the spike solution with the wet sediment the samples
were dispersed using a high speed dispersion tool (Ultra
Turrax, IKA, Germany). After 1 h of mixing the ana-
lytical procedure cited above was applied to the spiked
2. Materials and methods
2.1. Sampling
In 1993 and 1994 surface sediment samples (Fig. 1)
were taken from the Elbe river, the Hamburg Harbour
(E0–E10) and the tributaries Mulde (M1–M10), Havel
(H3, H5) and Spree (S2, S9, S10, S13, S14) including the
Teltow Canal (T1, T2, T5, T6). In addition subsamples
of sediment cores drawn in the Hamburg Harbour in
1987/1988 (E11–E14) were analysed. SPM from the Elbe
Fig. 1. Sampling locations of sediment and SPM (ES) in the Elbe river system.

J. Schwarzbauer, S. Franke / Chemosphere 51 (2003) 973–981
975
sediment samples. The two independent determinations
of the recoveries of the 1,2- and 2,2-isomers gave values
between 63% and 75% with a relative standard deviation
of approx. 10%. Based on these data a method recovery
of 70% was used for quantification. It has to be stated,
that the recoveries determined in the way described need
not to be representative for the extraction yield from
real samples, but they represent definitely the losses
during the extraction, fractionation and concentration
procedures.
(18.7 mmol) of concentrated sulphuric acid were added
to 7.5 g (58 mmol) of naphthalene and, subsequently the
mixture was heated at 180 °C for 8 h. After cooling
to room temperature approximately 10 ml water were
added to quench the reaction. The precipitate was sep-
arated and redissolved in 50 ml ether. The solution was
washed with water, dried over anhydrous MgSO4 and
the solvent was evaporated. After sublimation of unre-
acted naphthalene at 120 °C the crude product was
cleaned by column chromatography on silica gel (Merck
Kieselgel 60, 250–400 mesh) using a mixture of petrol
ether and dichloromethane (4:1 v/v) as eluent. The pre-
cleaned product was recrystallized twice from ethanol.
The reaction yielded an isomeric mixture of 1,2- and 2,2-
dinaphthylsulfones in a ratio of 4:5. Elemental analysis:
C 75.5% (calc.: 75.5%), H 4.5% (4.4%), O 10.0% (10.0%),
S 10.0% (10.1%).
2.3. GC/MS and gas chromatography/FTIR-spectroscopy
GC/MS screening analysis was performed on a VG
70-250 SE mass spectrometer linked to an HP 5890 gas
chromatograph which was equipped with a 30 m ꢀ 0.25
mm i.d. ꢀ 0.25 lm film DB-5 fused silica capillary col-
umn. Chromatographic conditions were: 1 ll on-column
injection at 50 °C, 3 min hold, then programmed at 3 °/
min to 300 °C, helium carrier gas velocity 25 cm/s.
Gas chromatography/FTIR spectra (GC/FTIR) were
taken using a HP 5965A IRD coupled to an HP 5980
Series II GC under the following conditions: flow-cell
temperature 290 °C, optical resolution 4 cmꢁ1, 30 m ꢀ
0.25 mm i.d. ꢀ 0.25 lm film DB-5 MS capillary column,
1 ll 60 s splitless injection at 280 °C, 3 min hold, then
programmed at 5°/min to 300 °C, hydrogen carrier gas
velocity 38 cm/s.
3. Results and discussion
3.1. Identification of 1,1-, 1,2- and 2,2-dinaphthylsulfone
GC/MS screening analyses applied to particulate
matter samples of the Elbe river and its tributaries
Havel, Spree and Mulde revealed a group of three
dinaphthylsulfone isomers. During fractionation of the
crude sediment extracts by column chromatography
the dinaphthylsulfones eluted with the most polar
fraction. This pointed to the presence of polar func-
tional groups in these compounds. In GC/MS the
isotopic pattern of the molecular ion indicated the
presence of a sulfur atom, and the fragment at m=z 127
the presence of a naphthyl moiety in each isomer. First
structural information was obtained by comparison
with a poor quality mass spectrum of 2,2-dinaphthyl-
sulfone as given by the NIST mass spectral data base.
The mass spectrum of one of the substances showed
the same fragments but different ion intensities. The
identity of the second and third eluting dinaphthyl-
sulfones was then proven by comparison with retention
times and mass spectra of the synthetic mixture ob-
tained by direct sulfonation of naphthalene. Both gas
chromatographic peaks were assigned to the individ-
ual isomers (1,2- and 2,2-dinaphthylsulfone) by GC/
FTIR analysis of the synthesis products as described
above.
Quantitative GC/MS analysis was carried out on a
quadrupole mass spectrometer HP 5985 linked to an HP
5890 gas chromatograph. For chromatographic separa-
tion, a 30 m ꢀ 0.28 mm i.d. ꢀ 0.25 lm film MXT-5 fused
silica lined steel capillary column was used under the
conditions described above. The target compounds were
detected by single ion monitoring (SIM) of m=z 127 and
m=z 318. The peak area of m=z 310 was used for quanti-
tation and the integrated areas were checked by the rela-
tive abundances of the corresponding ion m=z 127.
Injection volume and sample volume inaccuracy were
corrected for by using d12-benzo(a)anthracene (m=z 240) as
an internal standard. An external four-point-calibration
generated from a synthetic mixture of dinaphthylsulfones
was used for quantitation. As 1,1-dinaphthylsulfone did
not appear in the synthetic mixture the mass spectral
response factor of the 1,2-isomer was used after a cor-
rection corresponding to the relative proportion of the
ions used for quantitation in relation to the total ion in-
tensity. The detection limit was in the range of 0.5 lg/kg
dry weight; no attempts were made to quantify compo-
nents at concentrations of less than 1 lg/kg.
As the synthetic mixture only contained the above
introduced isomers, a structure elucidation based on
GC/FTIR analysis was not able for the first eluting
peak. But considering the limited number of possible
isomers (only 1,1-, 1,2- and 2,2-substituted isomers are
conceivable) and the mass spectral properties as de-
scribed below the assignment of this compound to the
1,1-substituted isomer is obvious.
2.4. Synthesis of reference compounds
A synthetic mixture of dinaphthylsulfone isomers
was obtained by direct sulfonation of naphthalene. 1.84 g

976
J. Schwarzbauer, S. Franke / Chemosphere 51 (2003) 973–981
In addition, the order of gas chromatographic re-
peak, and a fragment m=z 175 is not observed. The mass
spectrum of the 2,2-isomer is characterized by a base
peak at m=z 175 with an elemental composition of
C10H7OS, and m=z 253 is of minor intensity. The pre-
ferred fragmentations of the 1,1- and 2,2-isomers com-
bine in the 1,2-isomer to produce the base peak m=z 253
and the fragment m=z 175 (30% BPI). The differences in
the mass spectra of the dinaphthylsulfone isomers orig-
inate from a competition of two fragmentation path-
ways: the extrusion of an HSO2-radical, and the loss of
a naphtholyl-radical (C10H7O). Extrusion of a HSO2-
radical from the molecular ion requires the transfer of a
hydrogen to the SO2-moiety, and this is the preferred
fragmentation pathway if an 1-naphthyl residue is pre-
sent in the molecule. As molecular models show, in the
1,1- and the 1,2-isomers the 8-naphthyl (c-) hydrogen
atom(s) are in close vicinity to one of the oxygen atoms
of the SO2 group, while the 8-naphthyl- and c-hydrogens
are far more distant in the 2,2-isomer. The loss of a
tention on non-polar GC columns as revealed by these
analyses (1,1- < 1,2- < 2,2-isomer; Fig. 2) was in accor-
dance with literature data (Yoshii et al., 1972).
3.1.1. Mass spectra of dinaphthylsulfones
The mass spectra of dinaphthylsulfones (Fig. 3) are
characterized by a few intense ions. In addition to the
molecular ion (m=z 318) the naphthyl fragment ion m=z
127 is observed with high abundance in the mass spectra
of all isomers. These mass spectral properties were re-
ported formerly from a gas chromatographically unre-
solved mixture of isomers (Thruiston and McGuire,
1981). But differences in the formation of the base peak
and the relative abundance of further major fragments
depending on the position of substitution at the naph-
thalenic system are obvious. In the mass spectrum of the
1,1-isomer the fragment ion m=z 253 generated by the
loss of HSO2 from the molecular ion forms the base
Fig. 2. Ion traces of molecular (m=z 318) and fragment m=z 127 ions of dinaphtyl sulfones. A: sediment M9, Mulde at Bitterfeld–
Wolfen, B: synthetic dinaphthylsulfone mixture.

J. Schwarzbauer, S. Franke / Chemosphere 51 (2003) 973–981
977
253
100
SO2
50
127
318
115
101
75
253
100
SO2
127
318
50
175
175
115
77
101
318
100
SO2
127
50
115
252
101
m/z
40 60 80 100 120 140 160 180 200 220 240 260 280 300 320
Fig. 3. Mass spectra of dinaphthylsulfones.
naphtholyl-radical requires the rearrangement of the
dinaphthylsulfone to a naphthyl-naphthtalene sulfinate
prior to fragmentation. This fragmentation pathway
operates only if a 2-naphthyl residue is present in the
molecule.
3.1.2. Infrared spectra of dinaphthylsulfones
The gas phase infrared spectra obtained by GC/FTIR
analysis of a synthetic mixture of 1,2- and 2,2-dinaph-
thylsulfone are shown (Fig. 4) in the wave number re-
gion from 1850 to 500 cmꢁ1. In addition to a band at

978
J. Schwarzbauer, S. Franke / Chemosphere 51 (2003) 973–981
Fig. 4. Gas phase IR-spectra of synthetic dinaphthylsulfones (A ¼ 1; 2-isomer, B ¼ 2; 2-isomer).
3064 cmꢁ1 (aromatic C–H stretching mode, not shown)
the spectra contain the absorption bands of the anti-
as described above. In the spectrum of 2-methylnaph-
thalene the bands at 844 cmꢁ1 (deformation mode of an
isolated H in an aromatic ring), 806 cmꢁ1 (deformation
mode of two neighbouring hydrogen atoms in an aro-
matic ring) and 735 cmꢁ1 (deformation mode of four
neighbouring hydrogen atoms in an aromatic ring) re-
flect the 2-substitution and consequently appear also in
the IR-spectrum of 2,2-dinaphthylsulfone with a slight
shift of approx. 10 cmꢁ1. The IR-spectrum of 1-meth-
ylnaphthalene shows two adjacent bands at 786 and 770
cmꢁ1 (deformation modes of three and four neighbour-
ing hydrogen atoms in an aromatic ring), that are
characteristic absorptions for the 1-substitution. Ac-
symmetrical (1340 cmꢁ1) and symmetrical (1160 cmꢁ1
)
stretching modes of the sulfone group (Flett, 1962).
Wave numbers and intensities of these bands are not
affected by the substitution position. Isomer specific in-
formation could be drawn from the spectral region be-
tween 700 and 900 cmꢁ1 where the bands of the
deformation modes of aromatic C–H bonds occur. A
comparison of the dinaphthylsulfone spectra with the IR
data of 1- and 2-methylnaphthalene in this spectral re-
gion is given in Table 1. The spectra of 1- and 2-methyl-
naphthalenes were measured under the same conditions
Table 1
C–H out-of-plane IR-absorption bands (cmꢁ1) of dinaphthylsulfones and methylnaphthalenes
1,2-Dinaphthyl-
sulfone
2,2-Dinaphthyl-
sulfone
1-Methyl-naphtha- 2-Methyl-naphtha- Aromatic C–H out-of-plane vibrations
lene
lene
856
815
790
768
742
858
812
844
806
900–800
860–800
810–750
Isolated H
2 neighbouring H
3 neighbouring H
4 neighbouring H
4 neighbouring H
786
770
742
735
770–735
All measurements were performed on the same GC/FTIR system under identical analytical conditions.

J. Schwarzbauer, S. Franke / Chemosphere 51 (2003) 973–981
979
cordingly, the spectrum of the 1,2-dinaphthylsulfone
shows bands at 856, 768 and 742 cmꢁ1 and an unre-
solved absorption between 790 and 815 cmꢁ1 as a result
of the appearance of the 1- and 2-indicating bands.
These data definitely allowed the assignment of the po-
sitional isomers.
3.2. Dinaphthylsulfones in sediments and SPM of the Elbe
river system
Dinaphthylsulfones were detected in all investigated
areas of the Elbe river system (Fig. 1, Table 2). In gen-
eral the concentrations of the 1,2- and 2,2-isomers
Table 2
Concentrations of dinaphthylsulfones in sediments and SPM (lg/kg dry matter)
1,1-Dinaphthyl-sulfone
1,2-Dinaphthyl-sulfone
2,2-Dinaphthyl-sulfone
Sum
Sediments
Mulde river
M1
<1
<1
<1
<1
50
<1
60
<1
50
M2
M3
110
190
90
100
<1
130
280
240
M4–M7
M8
M9
<1
410
670
510
590
1080
830
130
80
M10
Havel and Spree rivers, Teltow Canal
H3
H5
<1
<1
<1
20
<1
10
<1
5
15
S2, S10, S13, S14
<1
90
<1
70
S9
T1
T2
T5
T6
180
580
790
100
50
40
290
410
40
240
340
40
20
<1
<1
<1
Elbe river
E0
E1
50
10
20
5
260
50
200
15
40
10
<1
5
510
75
E6
E7
70
35
130
50
E8
E9
<1
<1
<1
<1
15
20
E10
<1
<1
Hamburg harbour
E2
50
20
190
110
93
160
30
400
160
152
740
1330
644
530
190
E3
E4
20
39
E5
110
170
114
70
490
670
300
260
90
140
490
230
200
70
E11
E12
E13
E14
30
Suspended matter
Elbe river
ES1
ES2
640
<1
290
<1
740
60
1900
<1
340
<1
910
<1
770
90
2880
2300
ES3
ES4
1100
<1
ES5
ES6
2600
90
4110
240
150
510
ES7
ES8
<1
50
100
260
50
200

980
J. Schwarzbauer, S. Franke / Chemosphere 51 (2003) 973–981
exceeded the 1,1-dinaphthylsulfone concentrations. Sed-
iments of the upper and middle part of the Mulde river
(M1–M7) contained low amounts of 1,2- and 2,2-
dinaphthylsulfone, whereas the samples situated at the
confluence with the Elbe river (M8–M10) near an in-
dustrial area were contaminated with concentrations up
to 1100 lg/kg. In sediments of the Havel and Spree
rivers, and the Teltow Canal dinaphthylsulfones were
present in low concentrations between the limit of
quantitation and 180 lg/kg. Only at sampling sites T1
and T2, also situated near an industrial plant concen-
trations increased up to 790 lg/kg. These spatial distri-
butions suggest a low background contamination of the
riverine sediments superimposed by local industrial
emissions of dinaphthylsulfones. This is in accordance
with the formerly reported occurrence of dinaphthyl-
sulfones in tannery and industrial effluents as well as in
sediments situated near a chemical plant producing
condensed sulfonated polymers (Jungclaus et al., 1978;
Sheldon and Hites, 1978; Thruiston and McGuire,
1981). Furthermore, related compounds (e.g. naphthyl
sulfonic acids, sulphonated polyphenols) are well-known
constituents of industrial effluents and were frequently
described in the aquatic environment (Reemtsma et al.,
1993; Fichtner et al., 1995; Zerbinati et al., 1997; Alonso
and Barcelo, 1999).
Havel and Spree revealed the presence of all three iso-
mers of dinaphthylsulfone. The mass spectral fragmen-
tation depends on the substitution position at the
naphthalenic ring system leading to clearly distinguish-
able EI-spectra of the different isomers. Upon GC/FTIR
analysis isomer specific absorption bands in the IR wave
number region between 700 and 900 cmꢁ1 allowed to
differentiate the 1- and 2-substitution, and thereby to
assign the dinaphthylsulfone positional isomers. Ac-
cordingly, the gas chromatographic elution order on
non-polar phases was confirmed to be 1,1- (1), 1,2- (2)
and 2,2- (3). Quantitative analyses of sediments and
SPM from the Elbe river system showed a background
contamination with dinaphthylsulfones superimposed
by two point source emissions situated in industrial
areas (Teltow Canal, lower part of the Mulde river), and
a strong contamination of the upper Elbe river, and the
Hamburg harbour area. The occurrence in recent and
older layers of harbour sediment indicates a long emis-
sion history and a high stability of dinaphthylsulfones
under anaerobic conditions in the aquatic environment.
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4. Summary and conclusions
GC/MS screening analyses applied to sediment and
SPM samples of the Elbe river and its tributaries Mulde,

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