Achievements in the Life Sciences 10 (2016) 65–71

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Achievements in the Life Sciences

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Contents of 4-Nonylphenol in Surface Sea Water of Amur Bay (Japan/East Sea)

Andrei P. Cherniaev a,b,⁎, Aleksandra S. Kondakova c, Ekaterina N. Zyk a
a
The School of Natural Sciences, Far Eastern Federal University, 753 Office, Bldg. L, Ajax St., Vladivostok, Russky Island 690922, Russia
b
Pacific Research Institute of Fisheries and Oceanography (TINRO-Center), 4 Shevchenko Alley, Vladivostok 690090, Russia
c
Vladivostok State University Economics and Service, 41 Gogolya Str., Vladivostok 690014, Russia

a r t i c l e i n f o a b s t r a c t

Article history: The determination of 4-nonylphenols has been developed using HPLC with fluorescence detec-
Received 9 March 2016 tion method. 4-Nonylphenols in sea water samples were extracted using a liquid–liquid extrac-
Received in revised form 13 May 2016 tion. Acidification and adding salting-out agents (NaI) of water samples increased the
Accepted 31 May 2016
extraction degree. The extraction of 4-nonylphenols was done twice with 20 mL of methylene
Available online 23 June 2016
chloride. The applied concentrated range was over 5–1000 ng/mL for the 4-nonylphenol. The
recovery test ranged from 78.5 to 89.9% with relative standard deviations between 1.0 and
Keywords: 7.5% of 100 ng/mL of the standard phenols spiked with the water sample and the detection
4-Nonylphenol
limit was 1 ng/mL. The proposed method was applied satisfactorily for the determination of
HPLC
4-nonylphenole in sea water samples. Levels of 4-nonylphenol were determined in the sea wa-
Sea waters
Amur Bay ters of the Amur Bay. Water samples were collected every year from 2008 to 2015. Concentra-
tions of 4-nonylphenol in the waters ranged from levels below the detection limits up to
1.24 μg/L.
© 2016 Far Eastern Federal University. Hosting by Elsevier B.V. This is an open access article
under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Introduction

Alkylphenol compounds appear in waste waters of major industrial centers, and their content in coastal sea water areas may
be rather high and influence living organisms negatively (Taylor and Harrison, 1999). One of the representatives of alkylphenol
class is 4-nonylphenol not allowed to be dumped in the exclusive economic zone of the Russian Federation (http://
base.garant.ru/12147594/). However there are some data about the presence of 4-nonylphenol and other compounds of
alkylphenol class in sea waters (Kondakova et al., 2012).
4-Nonylphenol, as well as some other alkylphenols, has strongly marked xenoestrogen properties (Bernacka et al., 2009; Peng
et al., 2006). For the first time estrogenic activity of phenols was noted in 1978 (Muller and Kim, 1978). Xenoestrogens (de-
stroyers of endocrine system) are substances of anthropogenic origin, simulating, copying or blocking the effect of natural hor-
mones synthesized by the endocrine glands; they interact with estrogen receptors and change a normal course of biochemical
processes of the cell (Renner, 1997). Xenoestrogens influence the reproductive and endocrine systems of animals as well as estro-
gen, cause feminization of the population and have mutagenic and carcinogenic effects (Vazquez-Duhalt et al., 2005).
4-Nonylphenol formed in the environment by the degradation alkylphenolpolyethoxylates (AP) (Ike et al., 2002; Jonkers et al.,
2001). AP are actively used in various industrial processes (Kneeper and Berna, 2003). Oil, mining, chemical, textile, plastic and
pulp-and-paper industries are the major consumers of these products (Kneeper and Berna, 2003; Maguire, 1999; Soto et al.,

⁎ Corresponding author at: The School of Natural Sciences, Far Eastern Federal University, 753 Office, Bldg. L, Ajax St., Vladivostok, Russky Island 690922, Russia.
E-mail address: blizzardvl@gmail.com (A.P. Cherniaev).
Peer review under responsibility of Far Eastern Federal University.

http://dx.doi.org/10.1016/j.als.2016.05.006
2078-1520/© 2016 Far Eastern Federal University. Hosting by Elsevier B.V. This is an open access article under the CC BY-NC-ND license
(http://creativecommons.org/licenses/by-nc-nd/4.0/).
66 A.P. Cherniaev et al. / Achievements in the Life Sciences 10 (2016) 65–71

1992). Alkylphenol polyethoxylates are the most widespread non-ionogenic surface-active substances all over the world due to
their high stability and excellent cleaning and emulsifying properties (Maguire, 1999; Berryman et al., 2004).
Despite the fact that alkylphenolpolyethoxylates are not classified as highly toxic substances and can be effectively removed
from waste waters by means of standard cleaning, they represent a class of highly environment-hazardous compounds
(Canadian Council of the Ministers of the Environment, 2001). The reason for that is the fact that anaerobic condensation and bio-
transformation result in nonylphenol polyethoxylates transforming into stable short-chain metabolites, such as 4-nonylphenol
which is considered as a potential destroyer of the endocrine system (Berryman et al., 2004).
In connection with marked lipophilic properties, 4-nonylphenol can be accumulated in the organic matter and lipids of solid
matrices and animals, respectively. Bioaccumulation effects, which may be present in the next generations though may be of
sharp-toxic nature as well (Peng et al., 2006).
Due to high toxicity, large production volumes and high stability in the environment, the world's ecological and governmental
organizations suggested to impose restrictions on the use of APs (Canadian Council of the Ministers of the Environment, 2001).
Use of household detergents based on 4-nonylphenol is already forbidden or restricted in most European countries, for example,
in Switzerland the ban to use polyethoxylates of 4-nonylphenol was imposed as far back as 1986. In some other countries risk
reduction was achieved by voluntary agreement with detergent manufacturing companies (Ahel et al., 2000). According to the
Russian legislation (Regulation of the Russian Federation Government no. 251 dated March 24, 2000) and MARPOL Convention
73/78, discharge of nonylphenol to the marine environment is forbidden in the exclusive economic zone of the Russian Federa-
tion. Nonylphenol is entered in the “Bulletin of the Russian Register of Potentially Dangerous Chemical and Biological Substances”
(http://rpohv.ru).
There are some data in the literature about 4-nonylphenol content in river and lake waters as well as in coastal sea water
areas. 4-Nonylphenol was found in surface waters, discharged waters and bed silt of most developed countries: Canada, Great
Britain, Spain, Japan, USA, Germany, Taiwan, Switzerland and Italy (Li et al., 2004; Bester et al., 2001; Ying et al., 2002). Concen-
tration of nonylphenol in the environmental objects is varied from below detection level values to rather high concentration of
644 μg/L (Bernacka et al., 2009). According to the classification given by Baronti (Soto et al., 1992), surface waters with content
of nonylphenol less than 1 μg/L relate to poorly contaminated, 1–10 μg/L to contaminated, and more than 10 μg/L highly contam-
inated. According to a lot of researches, 4-nonylphenol is toxic for fishes (LC50 = 17–3000 μg/L). Invertebrate and marine algae
are also sensitive to the effect of 4-nonylphenol (LC50 in intervals of 21–3000 and 27–2500 μg/L, accordingly) (Vazquez-Duhalt
et al., 2005).
Analytical determination of alkylphenols is complicated due to their low concentration in the investigated matrices, dilution
and frequently high saline background of the sample. Therefore, concentration of 4-nonylphenol is necessary prior to its
determination.
Earlier, 4-nonylphenol content in coastal waters of the Russian Far East was not analyzed at all, that is why the purpose of this work
was to determine 4-nonylphenol levels in the region most affected by anthropogenic influence — the south of Primorsky region.

Materials and Methods

Solvents and Standards

Analytical standard of 4-nonylphenol (N 98% pure) was obtained from Alfa Aesar (Ward Hill, MA, USA). Sodium chloride, mag-
nesium sulfate, magnesium chloride, calcium chloride, potassium chloride, sodium bicarbonate, potassium iodide, potassium bro-
mide, sodium hydroxide, and anhydrous sodium sulfate, all N99% pure, were from Neva-reaktiv (St. Petersburg, the Russian
Federation). Hydrochloric acid solution (36% v./v. in water) was N98% pure. To perform the extraction, pentanol, benzene, and
hexane were used from Vekton (St. Petersburg, the Russian Federation), and methylene chloride, carbon tetrachloride were
from Ekos-1 (Moscow, the Russian Federation). All employed organic solvents were of high purity grade.
In the preparation of the basic, working standard solutions and extracts for chromatographic separation, acetonitrile (class 0
for chromatography) was used from Kriohrom (St. Petersburg, the Russian Federation). Basic standard solution with a concentra-
tion of 1000 μg/mL was prepared by dissolution of precisely weighed portion of 4-nonylphenol in acetonitrile and stored at a tem-
perature of −18 °С for not longer than 10 days. Standard working solutions of 4-nonylphenol in acetonitrile with concentrations
of 0.01, 0.05, 0.1, 0.5, 1.0 and 2.0 μg/mL were used for plotting the calibration curve (Fig. 1). Working standard solutions were
prepared immediately before the analysis.

Preparation of Artificial Seawater

Artificial seawater prepared according to Krot (1966) was used as artificial matrix. For this purpose weighed portions of dry
salts (sodium chloride, magnesium sulfate, magnesium chloride, calcium chloride, potassium chloride, sodium bicarbonate)
were dissolved in 500 mL of distilled water. The derived mixture was put into an ultrasonic bath for 5 min and diluted with dis-
tilled water to 10 L. Salinity of the prepared artificial seawater was 35 ± 0.5‰. Artificial seawater was stored at a temperature
from 0 to +2 °С for not longer than 5 days.
Sonication processing was performed used Sonorex Super, RK 52 (Bandelin electronic GmbH & Co KG, Germany, 50 Hz, 220 V).
 A.P. Cherniaev et al. / Achievements in the Life Sciences 10 (2016) 65–71 67

Fig. 1. Calibration curve.

Sampling Area and Water Collection

The sea water samples were taken at times from May to September every year from 2008 to 2015 (Fig. 2). Samples were col-
lected manually. One liter of filtered water sample was collected in 1 L dark glass bottle with Teflon cap. It was acidified with
1 mL of conc. HCl (pH ~ 2) to protect it from biodegradation. Samples were stored at 1 °С. The water samples were analyzed
within 3 days.
Stations no. 1 — estuary of the Ob'yasneniya River, no. 2 — the Zolotoy Rog Bight, no. 3 — Kuper Саре, no. 4 — estuary of the
Kedrovaya River, nos. 5, 7 — central part of the Amur Bay, no. 6 — estuary of the Barabashevka River, no. 8 — Tokarevsky Cape, no.
9 — Staritsky Cape, no. 10 — Ushi i., no. 11 — Matveeva stone, no. 12 — Vasiliev Cape, no. 13 — the Stark str., no. 14 — Prokhodnoy
Cape, no. 15 — Likander Cape, no. 16 — Lighthouse, no. 17 — De Vries Bay, no. 18 — Vladivostok Marine Station, no. 19 — estuary
of the Razdolnaya River.
PH-meter “HANNA-210” was used for control of the environment acidity.

Fig. 2. Location of sampling sites in the Amur Bay.

68 A.P. Cherniaev et al. / Achievements in the Life Sciences 10 (2016) 65–71

Extraction

Extraction of phenols was performed using liquid–liquid extraction treatment. The extraction of total phenols from the water
samples was performed with a total of 40 mL DCM (extracted twice with 20 mL of DCM), in the presence of sodium iodide and
pH is adjusted between 2.0 and 3.0 with hydrochloric acid in separating funnel. After separation the methylene chloride layer was
filtrated through anhydrous sodium sulfate. The obtained extracts were evaporated to 1 mL in a water bath (60 °C) on a rotary
evaporator at reduced pressure. The solution is then concentrated with dried nitrogen gas to dry residue. The total volume is ad-
justed to 1 mL with acetonitrile. This solution is ready for HPLC analysis. The concentration of total phenols from environmental
water samples was calculated by using “introduced–found” method.

Liquid Chromatography With Fluorescence Detection

Chromatographic measurement were taken using liquid chromatograph LC-10 ADvp (Shimadzu, Japan) with fluorescent detec-
tor RF-10AXL (excitation wave — 230 nm, emission wave — 320 nm). Separations were carried out on analytical column Discov-
ery С18 (25 cm × 0.46 cm, 5 μm particle size), mobile phase:water–acetonitrile (90:10 v./v.), and isocratic mode. The flow rate
was 0.5 mL/min.

Limit of Detection

Limit of detection was calculated as three times the signal of the background noise obtained in the analysis of water sample at
the retention times of 4-nonylphenol.

Results and Discussion

Selection of Conditions for Chromatographic Separation

Physical and chemical properties of the determined substance are important in the selection of conditions for chromatographic
separation. Alkylphenols are usually divided using sorbents, modified by alkyl groups (С8, С18). It makes it possible to make an anal-
ysis of highly polar compounds as well as to vary broadly polarity of mobile phase. Chromatographic determination of 4-nonylphenol
was carried out in reversed-phased conditions.
When selecting the eluent, various mobile phases were studied: compounds of acetonitrile and ethanol with water. If water–
alcohol solution is used, analytical definition is impossible due to asymmetry of 4-nonylphenol peak. Use of the phase acetoni-
trile–ethyl alcohol–water–acetic acid (50:30:19:1) did not bring any positive results as well due to the impossibility to detect
the peak of 4-nonylphenol. Apparently, decrease of eluent's рН value reduces a dissociation degree of 4-nonylphenol and will in-
crease molecular form content, which in turn leads to the increase in retention time. If acidified eluents were used, efficiency got
worse and the peaks became asymmetrical. An optimal variant was the use of the system acetonitrile–water (90:10), when the
peak form was symmetric and retention parameters were optimal.
Limit of detection for 4-nonylphenol when fluorescent detector was used equaled 1 ng.

Effect of Solvents

4-Nonylphenol extraction level was defined using various solvents. Artificial sweater was used as matrix. Benzene, hexane,
pentanol, carbon tetrachloride, and methylene chloride were used as solvents. Fig. 3 represents a dependence of 4-nonylphenol
recovery and polarity of the solvent used. Pentanol which has the highest dielectric permeability showed the most complete

Fig. 3. Influence of polarity (p′) on the recovery of 4-nonylphenol.

 A.P. Cherniaev et al. / Achievements in the Life Sciences 10 (2016) 65–71 69

extraction. However pentanol forms poorly splitting emulsions and that makes the results of extraction to be non-reproducible.
Methylene chloride was chosen as the most adequate solvent. It does not form any emulsions with water, and extraction level
of a target component is close to the level of extraction with pentanol.

Effect of pH

When studying the influence of acidity on the recovery of 4-nonylphenol, рН values were varied from 1 to 14 (Fig. 4). When
pH values are from 1 to 11 the recovery is unchangeable. When рН value is more than 11 the recovery is decreasing. Undissoci-
ated molecules of 4-nonylphenol and its ions are unequally extracted with organic solvents out of water solutions. During extrac-
tion, undissociated molecules transfer into the organic phase, and ions hydrated with water molecules remain in water phase.
Some discrepancy in the obtained dependence and theoretically calculated ionization degree is caused by an influence of the
saline background of artificial seawater. The high recovery was when pH value is up to 3 since at this stage the 4-nonylphenol
dissociation is almost completely suppressed and extraction is performed as effective as possible. However, when pH is less
than 2, the scattered results of the test are obtained. Thus, the best рН value for 4-nonylphenol extraction is 2.

Effect of Strong Electrolytes

Addition of strong electrolytes into water solution of target compound may decrease or increase its solubility in water. The
salting-out is explained by chemical interaction of salting-out agents and salting-out substances in the extraction systems. In re-
sult, compounds or complexes may be formed, which ultimately affect the value of the partition coefficient of the target compo-
nent between the organic and aqueous phases. Potassium salts were used as the salting-out agents; the added quantity of the
total sum of salts in the artificial matrix was 0.2 mol per 1 L (Helaleh et al., 2001). The salting-out agent ions with a small radius
have the greater charge density in comparison with the ions with a larger radius. Therefore, the ions with a small radius are hy-
drated better, and their salting-out effect is less than the same of the large ions. Iodide ion has the largest radius among the
salting-out anions being researched, and chloride ion has a minimal one. At that, the change of anion radius from 1.81 to
2.16 Å leads to an increase of 4-nonylphenol recovery in three fold, therefore the potassium iodide should be reasonably used
as a salting-out agent.
Thus, the technique of the analysis of 4-nonylphenol content in natural waters using methylene chloride as a solvent is offered,
at pH = 2 and in the presence of potassium iodide (0.2 mol per 1 L) as a salting-out agent with subsequent analysis applying the
method of reverse-phase high performance liquid chromatography.

Content of 4-Nonylphenol in Waters of the Amur Bay (East/Japan Sea)

The offered method is applied to determine the content of 4-nonylphenol in sea waters of the Amur Bay, the Russian Feder-
ation. The least polluted with 4-nonylphenol are the central part (St 5, 7) and the western coast (St 4, 6) of the Amur Bay, and the
most polluted are the Zolotoy Rog Bight (St 2, 8, 18) and the Ob'yasneniya River (St 1). The eastern coasts of the Amur Bay be-
come polluted with insufficient waste water treatment from settlements and industrial enterprises (St 19). The main pollutants
are electric power, municipal engineering, chemical industry, machinery and metal enterprises (Ogorodnikova, 2001). During a
year, a lot of waste water are discharged into the waters of the Amur Bay and adjacent waters. According to the state statistics,
46,332,96 thousand m3/year is discharged into Amur Bay, 23,480,27 thousand m3/year into the Zolotoy Rog Bight, and among
them 8222,83 thousand m3/year into the Ob'yasneniya River. All discharged waste waters are classified as “polluted, not treated”;

Fig. 4. Influence of pH on the recovery of 4-nonylphenol.

70 A.P. Cherniaev et al. / Achievements in the Life Sciences 10 (2016) 65–71

they include such polluting substances as: petrohydrocarbons (29.9 t/year), phenols (2.96 t/year), synthetic surface-active sub-
stances (86.37 t/year) and others (Chernyaev and Nigmatulina, 2013; Nigmatulina, 2007).
In result of the researches performed it was established that the content of 4-nonylphenol in the area of eastern coast of the
Amur Bay (Kuper Саре, St 3) makes 0.44 μg/L. One of 4-nonylphenol income sources is the cardboard factory located in Ussuriysk
constantly discharging the waste waters heavily contaminated with organic substances to the Razdolnaya River (St 19). Additional
contamination sources may be industrial wastes from some other enterprises as well as domestic waste water. By results of the
complex assessment in 2003, the waters of the Razdolnaya River are classified as “very dirty”, and maximum permissible concen-
tration (MPC) of phenols was six fold increased: this river delivers 26–28 fold more contaminants to Amur Bay in comparison
with all industrial and household city drains of Vladivostok. Existing currents in Amur Bay transfer water of the Razdolnaya
River along the east coast, and it evidences the presence of 4-nonylphenol in the coastal waters of the islands (St 8–15). The con-
centration of 4-nonylphenol in the seawaters of these stations is less than 0.01 μg/L. In the central part of the Amur Bay and in
area of the western coast (St 4–7), content of 4-nonylphenol is lower than the detection level. It is probably caused by the
large area, depth of the Bay and system of surface and underwater circulating currents owing to which the significant dilution
of the polluted waters takes place, and by significant remoteness of sources of 4-nonylphenol emission.
Content of 4-nonylphenol in the Zolotoy Rog Bight makes 1.22 μg/L (St 2). Specificity of this bay concerning the human impact
is that the same is one of the old-developed areas and consequently is the most exposed to the city waste waters. City ports and
ship repair yards discharging bilge waters, technical oils and fuel to Amur Bay water area exert a huge negative influence. The
Ob'yasneniya River (St 1) which waters contain 1.24 μg/L of 4-nonylphenol makes a significant contribution to the bay pollution.
Probably, one of the basic contamination sources is thermoelectric plant (CHP). A great quantity of waste water from cooling
and blow-down waters from return water supply systems, frequently polluted by transformer fuel components, is discharged
from the power plant without special treatment. It has been established that many components of transformer materials are
made of 4-nonylphenol containing phenol formaldehyde resins. Replacement of transformers and their destruction probably
leads to uncontrollable discharge of toxic components into the environment.

Conclusion

According to the above presented classification, waters of the Amur Bay may be referred to as “poorly contaminated waters”.
The existing concentrations of 4-nonylphenol in Amur Bay waters are not capable to give any significant negative influence in the
endocrine system of marine organisms and much less to cause their death. In the waters of the Zolotoy Rog Bight and the
Ob'yasneniya River, content of 4-nonylphenol is at a subcritical level and is capable of causing some changes in the structure of
marine organism communities. These waters are classified as “contaminated” (Baronti, 2000).
Marine organisms are one of the important links in a food chain when toxicants get into a human organism. Thus the existing
situation predetermines the necessity of carrying out high-grade monitoring works, revealing and classifying sources of pollution
by the substances showing xenoestrogenic effect.

Acknowledgment

The analysis of samples was performed with support from the Russian Science Foundation (agreement no. 14-50-00034).

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