Home > Novel Sample Preparation and GC–MS/MS Analysis of Triclosan and Methyl Triclosan in Biosolids

Novel Sample Preparation and GC–MS/MS Analysis

of Triclosan and Methyl Triclosan in Biosolids
Oct 01, 2017
By M. Bozlee [1]
Special Issues
Volume 35, Issue 10, pg 6–13

The antimicrobial triclosan is present in myriad personal care products, many of

which are disposed of down household drains and travel to wastewater
treatment plants. Triclosan and its metabolite, methyl triclosan, remain in
biosolids even after treatment for use on agricultural lands and domestic
gardening. Triclosan presents a host of environmental concerns, and methyl
triclosan is assumed to have similar risks. This article describes a simple and
rapid method for the preparation and extraction of triclosan and methyl triclosan
from the complex matrix of biosolids and paper mulch samples followed by
analysis using gas chromatography–tandem mass spectrometry (GC–MS/MS).
No derivatization or cleanup steps are needed, resulting in significant time
savings. Components within the paper mulch enhance the poor response of
underivatized triclosan. Matrix-matched standards exploit this matrix effect and
lower the limit of quantitation (LOQ) by a factor of 10. The quantitative analysis
is carried out using isotopic dilution to enhance precision and accuracy. This
method was used to investigate the use of earthworms (Eisenia fetida) as a
bioremediation agent to remove triclosan and methyl triclosan from biosolids.

Triclosan (TCS) is one of many pharmaceutical and personal care chemicals that enter
wastewater treatment plants, but are only partially removed during treatment. Some of
these recalcitrant chemicals are discharged in its effluent, but others such as TCS are
hydrophobic (log KOW 4.8) and primarily partition to the solids (1). Even after
additional treatment, much of the TCS will remain in biosolid products destined for
consumer and agricultural use.

Regardless of the treatment process used at a wastewater treatment plant or the

population demographics of the source, TCS is one of the most ubiquitous identified
compounds and among the highest concentration levels of analytes tested for in
biosolids (2,3). TCS is also fairly stable; with a half-life of 315 to 770 days in sewage
sludge and 104 days is soil after land application of biosolids (4,5). The safety of TCS
in biosolids is debatable. Studies have shown that TCS has a low toxicity to plants,
invertebrates, birds, and mammals and poor plant uptake, while other studies have
identified effects such as endocrine disruption, algae toxicity, and possible TCS-
induced antibiotic resistance (6–15). The United States Food and Drug Administration
(US FDA) issued a final rule establishing that over-the-counter consumer antiseptic
wash products containing certain active ingredients, including triclosan, can no longer
be marketed as of September 6, 2017. The ruling was partially based on possible
health risks and also on the lack of effectiveness over soap and water, but does not
include consumer hand “sanitizers,” wipes, or antibacterial products used in health-
care settings (16).

Methyl triclosan (M-TCS) is a metabolite of TCS that is also present in biosolids but at
much lower concentrations (17). Compared to TCS, it is even more resistant to
biodegradation and photolysis with a half-life of 443 days in soil after land application
of biosolids (18). M-TCS is not as well studied, but it is even more hydrophobic,
lipophilic, and bioaccumulative (19,20). Soil tested 4 years after biosolids application
showed M-TCS had a concentration six times that of TCS, highlighting the need to
understand this transformational product as much as its parent compound (21).

As they consume and degrade organic matter in soils, earthworms biomagnify

inorganic and organic contaminants, including mercury, lead, cadmium, polycyclic
aromatic hydrocarbons, fire retardants, pesticides, and TCS (22–26). More specifically,
they can bioaccumulate chemical contaminates in biosolids amended soils (2,26,27).
Kinney and colleagues (27) calculated the ratio of the concentration of contaminant
inside the earthworm to the concentration of contaminant in the soil or
bioaccumulation factor (BAF). Of all the contaminants detected in the worm and soil
samples, TCS had the highest BAF of 27 (24). Bioaccumulation of M-TCS in
earthworms has also been shown to occur in soils after biosolid applications (21).

Vermiculture is the practice of cultivating earthworms while transforming solid waste

and organic biosolids into a soil amendment product. This practice can save energy,
water, and reduce greenhouse gas emissions (28). Large-scale operations are
currently practiced in Canada, Italy, Japan, Malaysia, the Philippines, and the United
States (29,30). However, their ability to bioaccumulate pharmaceutical and personal
care products (PPCPs) from biosolids before being applied to gardens, lawns, and
agricultural lands remains largely unexplored and another possible benefit.

The biosolids department of Tacoma, Washington, teamed up with graduate student

Whitney P. Weibel to better understand vermiculture possibilities with PPCPs. In
support of her master’s thesis, “Examining the Feasibility of Vermicomposting
Biosolids Prior to Land Application to Remove Triclosan and Methyl Triclosan,” the
city’s environmental laboratory was tasked with developing a method for identifying
and quantifying these chemicals in biosolids (31). This article takes a closer look at
that research.

Method Development
The overall goal for the laboratory was to produce reliable, useful results while
constraining cost, time, and labor. Method development goals included a simple,
effective extraction and analysis with minimal handling and processing required (that
is, no cleanup, solvent exchange, concentration, or derivatization steps using a single
injection to identify and quantify both chemicals of interest) (Figure 1).

Figure 1: Project goals.

Preparation and Extraction

The preparation and extraction is fast and simple. Worm bin samples are milled into a
fine powder to enhance extraction efficiency and homogeneity, 5 mL of methylene
chloride is added followed by a 2-min vortex, a 5-min sonication, another 1-min vortex,
and filtration. This approach minimizes sample size, solvent usage, supply costs, and
waste generated.

Analysis

M-TCS works well with gas chromatography (GC), but TCS is more suitable to liquid
chromatography (LC) analysis. Many polar compounds such as TCS are better
analyzed by GC with derivatization, which reduces polarity, enabling them to be eluted
at reasonable temperatures without thermal decomposition while improving separation
and sensitivity (32–34). Compounds like TCS that contain a functional group with an
active hydrogen -OH are a major concern because of their affinity to form
intermolecular hydrogen bonds (35). However, avoiding derivatization can provide
better accuracy and precision by decreasing the number of sample handling steps as
well as factors such as incomplete derivatizations and artifact creation, especially in
crude complex matrices without cleanup (36,37).
To successfully achieve an analysis of a complex matrix without cleanup steps and
derivatization, GC coupled to tandem mass spectrometry (MS/MS) was chosen.
MS/MS improves selectivity and confidence in analyte confirmation while also
increasing sensitivity by decreasing background interference in selected-ion
monitoring (SIM) mode. Calibration standards showed very low sensitivity for TCS;
however, matrix spike recoveries of the worm bin samples showed a dramatic matrix
enhancement. The spike recovery immediately following the native sample analysis
was above 300%, and recoveries continued to rise to nearly 600% with additional
spikes in the analytical sequence before termination. M-TCS recovery also increased
to 176%. This phenomenon was not seen during prior testing with 100% biosolid
samples. However, the worm bin samples consisted of two components: biosolids and
paper mulch. The paper mulch provides bedding and an extra carbon source for the
earthworms. Each matrix component was extracted and spiked separately, and the
results showed that the increased sensitivity was because of the paper mulch.

The proposed mechanism of this enhancement is called matrix-induced

chromatographic response. The response improves peak intensity and shape for
certain compounds in the presence of a complex matrix (38,39). The enhancement of
matrix-induced chromatographic response is caused by a blockage of active sites in
the injector by matrix components. Masked active sites, such as free silanol groups
and metals, prevent thermal degradation-adsorption of the target analytes, thus
increasing the transfer of analytes to the detector. Within the analytical column,
coeluted matrix compounds that block active sites may also be responsible for the
phenomenon (38). Usually, compounds prone to matrix-induced chromatographic
enhancement are either thermally labile or polar analytes capable of hydrogen
bonding, which is consistent with the properties of TCS. It is also a common effect
observed with the analysis of certain pesticides (38,40).

Various cleanup procedures could have been used to remove the interferences and
negate the enhancement; we were trying to avoid using those procedures. The
alternative practice of matrix-matched calibration was chosen to compensate for
matrix-induced chromatographic enhancement. Considering that the major issue with
underivatized TCS is its low response, matrix-matched standards could take
advantage of this matrix effect to produce higher sensitivity. As such, milled paper
mulch was added to each of the calibration standards at approximately the same
amount as the worm bin samples. Sensitivity rose significantly, but variability continued
to be large. Before the calibration, injections of the highest concentration standard
were continued until the sensitivity seemed to stabilize. However, this technique only
marginally improved the variability.

Isotopically labeled internal standards were selected as a means to compensate for

this variability. Theoretically, the same degree of ion enhancement should be observed
for the target analytes and their isotopically labeled analogues, effectively providing a
correction to account for response variability and improve the quantification accuracy
(41,42). The isotopes for TCS and M-TCS were introduced before the extraction to
compensate for extraction efficiency in addition to the matrix enhancement
phenomenon during analysis.

The combination of a matrix-matched calibration and isotopic internal standards

proved to work well (Table I). The enhancement was significant. A greater than
sevenfold signal enhancement at 10 ng/mL was observed and the low point of the
linear curve decreased from 10 ng/mL to 1 ng/mL. M-TCS was also enhanced by 57%
at 10 µg/mL (Figure 2). The correlation coefficients were both above 0.9996. Each
calibration point was within 15% of the expected value, even at the lowest points of 1
ng/mL for TCS and 0.5 ng/mL for M-TCS. The stability of the calibration standards and
instrument was periodically checked over a 35-day period. Recoveries ranged from
89% to 115% (using calibration standards ranging from 5 ng/mL to 100 ng/mL). Limits
of quantitation (LOQs) of 20 ng/g for TCS and 10 ng/g for M-TCS were achieved for
the method.
Figure 2: Calibration with paper mulch (top line) versus no matrix (bottom line).

Methods
TCS was purchased as part of a mix (Pharmaceutical Mix #2) from Restek and a neat
M-TCS standard was purchased from Sigma-Aldrich. The 13C-labeled internal
standards were purchased from Cambridge Isotope Laboratories. Trace-level
methylene chloride for GC analysis was purchased from Honeywell. Paper mulch was
purchased from Applegate Mulch (100% recycled newsprint without added dye).
The biosolids and paper mulch samples, free of worms and eggs, were dried in a fume
hood for 96 h protected from light, milled into a very fine powder using a Retsch
cryogenic mill without nitrogen cooling and stored in a freezer at -20 °C until ready for
extraction. Sample extraction was performed by adding 0.25 g of sample to an 8-mL
amber screw-cap vial, followed by the addition of isotopically labeled internal
standards and then 5 mL of methylene chloride. The vials were vortexed for 2 min,
sonicated (Branson Ultrasonic Bath 3800) for 5 min, and then vortexed again for 1
min. The supernatant was transferred to a 2.7-µm syringe prefilter (GE Whatman) and
prefiltered into a 4-mL amber screw-cap vial. Then 0.5 mL of the filtrate was
transferred and filtered for analysis using a 0.2-µm self-filtering autosampler vial
(Agilent Technologies).

For the calibration, 0.15 g of milled paper mulch was added to each of the 8-mL amber
screw-cap vials, followed by the appropriate amounts of TCS, M-TCS, and isotopically
labeled standards and 5 mL of methylene chloride. The calibration standards were
extracted using the same procedure as the samples. Extracts were filtered (using a
0.45-µm glass fiber filter) and the instrument was conditioned by repeatedly injecting
the highest calibration standard until the area counts stabilized. This process ensured
that the matrix components had sufficiently masked the active sites in the system
before the calibration and samples were analyzed.

GC–MS/MS analysis was performed with an Agilent 7890 gas chromatograph

equipped with a split–splitless inlet and coupled to an Agilent 7000 triple-quadrupole
mass spectrometer. The split–splitless liner was a single taper 2.3-mm i.d. focus liner
with inert glass wool. The inlet liner was maintained at 280 °C. A 1-µL splitless
injection was used for calibration, sample, and quality control (QC) extracts.
Chromatographic analysis was carried out using a 20 m x 0.18 mm, 0.18-µm df Agilent
DB-5 column. Helium (purity 99.995%) was used as a carrier gas at a constant flow
rate of 1.1 mL/min. The oven was programmed to start at 70 °C, held at 70 °C for 0.5
min, ramped at 10 °C/min to 178 °C, and then slowed to a ramp of 2 °C/min to 196 °C
to completely resolve the closely eluted TCS and M-TCS peaks. Finally, a temperature
of 320 °C was reached at a ramp of 55 °C/min where it was maintained for 3.5 min.
The total analysis time was 26 min.

The MS precursor, quantitative, and qualifier ions are shown in Table II. Identification
is determined by comparing GC retention time, precursor ions, and no more than a
20% difference between the ratio of qualifier to quantifier ions compared to the
authentic standards. Quantitation is determined by using the response of the
quantitative daughter ion (shown in Table II) and a multipoint calibration of the target
analytes using the isotopic dilution technique.

Results
Much of the thesis effort was identifying suitable chemical and physical conditions for
earthworm (Eisenia fetida) health and survivability in various mixes of biosolids and
paper mulch (31). Unfortunately, only the repeated pilot study had earthworms survive
in the material long enough for evaluation of TCS and M-TCS removal. These results
showed a 75% reduction in TCS in 30 days (Figure 3). The known breakdown
pathways of TCS include photolysis, chlorination, ozone treatment, and aerobic
bacterial hydrolysis (43). At Tacoma’s wastewater treatment plant, chlorination does
not occur until after separation of the biosolids, the substrate was mostly kept in the
dark throughout the experiment, and ozone treatment is not incorporated. Aerobic
bacterial hydrolysis cannot be ruled out, but only 1% of the TCS loss can be explained
by the M-TCS gain (1,31). Therefore, the presence of earthworms may have had an
impact on the large decrease of TCS, which is consistent with findings from previous
research that earthworms can bioaccumulate TCS (2,21,27,44). However, further
research is needed to fully support this proposition, including earthworm uptake
studies.
Figure 3: Concentration of TCS and M-TCS before and after 30 days of vermicomposting.
Adapted with permission from reference 31.

M-TCS is formed in aerobic but not anaerobic environments and through the process
of microbial methylation of TCS (45). The city of Tacoma uses a brief 8–12 h aerobic
digestion, followed by a 30 day anaerobic digestion, which may explain the low initial
concentration of M-TCS (31). Some M-TCS was expected to form over the course of
the experiment without any influence from the earthworms. Unfortunately, the repeated
pilot test did not have a substrate without earthworms as a control. However, other
sample sets that were terminated early had controls that indicate the M-TCS
concentration increased, but less so than in the substrate with earthworms. The
presence of earthworms has been shown to increase biological activity of the microbial
communities within the substrate they are contained (46). This increased biological
activity may be responsible for the increase in TCS breakdown while the
corresponding uptake of M-TCS may occur at a slower rate. The abbreviated
experimental duration is insufficient and Eisenia fetida uptake studies are needed.

The concentration of biosolids, adjusted for percent weight in the worm bin samples,
ranged from 9100 ng/g to 12,800 ng/g dry, which is within literature limits. The
Environmental Protection Agency (EPA) surveyed sewage sludge from 84 wastewater
treatment plants subjected to secondary treatment or better and determined a
concentration range of 430–133,000 ng/g dry for TCS (3). However, an LC–MS/MS
screening of Tacoma’s biosolids using the same preparation and extraction procedure
but with a methanol–acetone extraction mix indicated a much lower concentration of
TCS, around 2200 ng/g dry (unpublished). The comparisons are from different
samples at disparate sampling events and provide only a snapshot. However,
efficiency between the two extractions may be a factor in the large disparity.
The method was further tested with worm bin samples containing widely different
proportions of biosolids, paper mulch mix, and cake from two additional treatment
plants, in Lynden, Washington, and Pierce County, Washington. Matrix spikes ranged
from 83% to 143% and relative standard deviations (RSDs) were 0–3%. The
increased spike recovery range may be caused by the proportion of paper mulch
extracted in the calibration standards not matching all of the variations received for
analysis.

Discussion and Conclusion

Using a simple extraction and a novel analysis method, excellent results can be
achieved for the analysis of TCS and M-TCS in the complex matrix of biosolids and
paper mulch. The preparation and extraction is fast and easy with no cleanup
procedures, derivatization, concentration, or solvent exchange required. GC–MS/MS
analysis involving matrix matched standards, isotopic dilution, and the use of paper
mulch was used to enhance the sensitivity, selectivity, and stability of the method. The
sensitivities for TCS and M-TCS were similar to other LC methods, as well as GC
methods that used large-volume injections or derivatization (47–51). Lower
quantitation levels were not needed for this project, but large-volume injection, a larger
sample size, concentration of the extract, further optimization of the inlet, and column
selection could be explored. Interestingly, M-TCS had a modest enhancement, even
without an active –OH group like TCS (Figure 2).

Analyte protectants, such as D-sorbitol, gulonolactone, and pepper leaf extract, are
substances added to samples and standards to block active sites within the GC
system and cause enhancement in lieu of using matrix-matched standards, or when
matrix-matched standards are not viable. Analyte protectants have also been used to
dramatically increase the storage length and stability of organophosphorus pesticides
standards (52). Their use has generally been limited to the scope of pesticide analysis.
There is a dearth of research using analyte protectants in GC for other relatively polar
compounds such as some PPCPs. Many phenolic compounds, such as TCS, are
analyzed using LC to avoid derivatization, but some thermolabile compounds may be
analyzed with adequate detection in GC using analyte protectants. Further research is
needed to determine if paper mulch extract is useful as an analyte protectant for other
PPCP compounds.

This work demonstrates that rather than being incinerated or dumped in landfills,
biosolids can be used as a nutrient-rich soil additive. Vermiculture can potentially
create a product with fewer anthropogenic chemicals before land application.

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M. Bozlee is with the Center for Urban Waters, City of Tacoma Environmental
Laboratory in Tacoma, Washington. Direct correspondence to:
MBozlee@CityofTacoma.org [4]

© 2019 UBM. All rights reserved.

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Links:
[1] http://www.chromatographyonline.com/m-bozlee
[2] https://www.epa.gov/biosolids/frequent-questions-about-biosolids
[3] http://ec.europa.eu/health/scientific_committees/consumer_safety/docs/sccs_o_023.pdf
[4] mailto:MBozlee@CityofTacoma.org