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Photocatalytic Degradation of Amoxicillin and Cephalexin from Aqueous

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Conference Paper · September 2018

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 International Congress on Engineering Science and Sustainable Urban Development
Denmark – Copenhagen
September, 2018

Photocatalytic Degradation of Amoxicillin and

Cephalexin from Aqueous Solution by ZnO and TiO2

Mohammadmehdi Fazilati1, Amir Hessam Hassani2*, and Ali Torabian3

1. MS of Environmental Engineer, Research Fellow, Department of Natural Resources and

Environment, Islamic Azad University Science and Research Branch, Email:
Mehdi.fazilati@yahoo.com
2. *Full Professor of Environmental Engineering, Corresponding authors, Department of Natural
Resources and Environment, Islamic Azad University Science and Research Branch, Tehran, Iran,
14778-93855. Email: ahh2002@yahoo.com
3. Full Professor of Environmental Engineering, Corresponding authors, Department of
Environmental Engineering, University of Tehran, Tehran, Iran. Email: atorabi@ut.ac.ir

Abstract
Not undestanding and recognizing the factors affecting waters containing pharmaceutical
compounds accurately will result in irrecoverable damages. For case in a point, the
development of antibiotic resistance in bacteria affect the denitrification process and
weaken methane-producing bacteria. To perform this investigation, after library
studies and collecting the required information, for the feasibility study of degrading
pharmaceutical compounds, advanced oxidation process by titanium dioxide and zinc
oxide nanoparticles from synthetic solutions was used.
The optimal values of pH were obtained at 5 and 7 for Amoxicillin and Cephalexin,
while the desired value of titanium dioxide and zinc oxide nanoparticles was obtained
as 2 g/L. The best contact time for Amoxicillin and Cephalexin by both nanoparticles
was achieved at 15 and 45 min and the optimum initial concentration of Amoxicillin
and Cephalexin was obtained as 15 and 5 mg/L, respectively. In 18 W radiation of
ultraviolet, the removal efficiency of Amoxicillin and Cephalexin with zinc oxide was
obtained as 48.6% and 81.8%, and with titanium dioxide was 27.6% and 63.5%,
respectively.
The results unveiled that the photocatalytic process of zinc oxide nanoparticles has a
higher efficiency compared to titanium dioxide nanoparticles.

Keywords: Photocatalyst, Titanium Dioxide, Zinc Oxide, Amoxicillin, Cephalexin

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1. Introduction
Water resources are of high significance. Today, metropolises are growing progressively,
with developing countries facing difficult situations. Mismanagement of water resources,
the growing competition for using freshwater, and decaying resources caused by pollutants
only increase the depth of these issues. The restriction of water resources, the incidence of
drought as well as the devastating effects of human activity on the environment have
contributed to serious challenges for benefiting from freshwater resources. Inappropriate
distribution of precipitation, the mismatch of demanding with time of precipitation, the dire
needing for investing in the storage, monitoring, and protection sectors of water resources
further complicate the dimensions of water challenge. Freshwater resources are considered
as renewable resources, whose renewability process follows the water cycle in nature;
however, the amount of water that emerges through this way across the earth or in any
geographical region is constant and specific regardless of year-round variations. Strict
protection of water resources against any contamination and reusing it are very significant
[1]. One of the main concerns of human beings these days is the entrance of
pharmaceutical compounds into water resources. If it is not controlled, it can result in
irrecoverable damages [2, 3].

In this regard, the objectives of this paper have been based on better understanding and
recognizing the performance of advanced oxidation processes by titanium dioxide and zinc
oxide nanoparticles in the degradation of antibiotics including Amoxicillin and
Cephalexin.
The method using in this study had been the photocatalytic process. The photocatalyst
consists of “photo” and “catalyst”, which is a substance causing the occurrence of a
chemical reaction in response to radiation and does not change itself. Photocatalysts are not
directly involved in oxidation-reduction reactions and only provide the conditions required
for proceeding the reactions [4].
1) TiO2 / ZnO + hv e–+ h +
1) h+ + H2O H+ + •OH
•
2) h+ + OH¯ OH
¯ •
3) e + O2 O2¯
4) HO2¯ + H2O + H+ H2O2 + OH¯
5) H2O2 + e¯ OH¯ + OH•
The consumed nanoparticles was included titanium dioxide and zinc oxide, which
structurally having three types of rutile, anatase, and brookite. Titanium dioxide is known
as titanium (IV) oxide or titania, with the chemical formula of TiO2. When it is used as a
dye, it is known as white titanium, white dye, and CI77891 [4].
Zinc oxide has the chemical formula of ZnO, which is a significant semiconductor with a
high band gap (37.3 eV) and excitation energy (60 meV) at room temperature. In recent
years, zinc oxide has attracted a great deal of attention mainly due to its unique optical,

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electronic, and piezoelectric properties. It also has found various applications including
solar cells, blue- light-emitting diodes, sensors, and reducers [7].
Jain et al., (2017) investigated the removal of rifabutin antibiotic using titanium dioxide
nanoparticles in the presence of ultraviolet radiation. They had used hydrogen peroxide as
a supplementary oxidant. After they had obtained the optimal conditions (contaminant
concentration=0.4 mg/L, pH=10.5, and catalyst concentration=0.06 g/L), they managed to
remove 85% of this antibiotic from aqueous environments [8].
In 2016 Kord Mostafapour conducted an investigation called the photocatalytic
degradation of ciprofloxacin using copper oxide in aqueous environments. At first, they
had measured the concentration of the antibiotic using the spectrophotometer device at the
maximum wavelength of 276 nm, then stated pH=7, nanoparticles dose of 0.07 g/L, and
time of 60 min as the optimal values. With the elevation of the antibiotic concentration
within the optimal time, they observed the maximum efficiency of the system as 73% [9].
In 2014 Akbari studied photocatalytic removal of doxycycline antibiotic using titanium
dioxide nanoparticles. The doxycycline was exposed under UV radiation using titanium
dioxide nanoparticles. The results indicated that, as a photocatalyst with suitable
performance in the presence of UV-C, titanium dioxide could be used for the removing of
doxycycline from aqueous solutions. They obtained removal percentage of doxycycline as
around 90.24 at the initial concentration of 20 mg/L, pH=6.5, the luminescence of 17 W,
and duration of 120 min [10].
Sadat Najafi studied photocatalytic removal of metronidazole antibiotic in aqueous
solutions using TiO2 nanoparticles under UV radiation. The results suggested that the
optimal conditions in the research included radiation time of 180 min, the antibiotic
concentration of 20 mg/L, and pH of 6. Under these conditions, removal of 94% of the
metronidazole antibiotic was obtained from aqueous solutions [11].
Dimitrakopoulou in 2012 dealt with removing Amoxicillin by ultraviolet and titanium
dioxide photocatalytic process. Their variables were involved antibiotic concentration=2.5-
30 mg/L, catalyst concentration=100-750 mg/L, acidic or close to neutral pH, and reaction
time=25-90 min. After analyzing the results, they achieved 93% removal of the
contaminant with the optimal catalyst concentration as 10 and 250 mg/L within 25 and 90
min as the optimal values. Furthermore, in this experiment, the results suggested that pH
had not been an influential factor in the removal efficiency [12].
Investigating the performance of titanium dioxide and zinc oxide nanoparticles in
removing antibiotics from the wastewater of pharmaceutical industries has been the main
purpose of this research.

2. Materials and Methods

2.1. Chemicals
This study has been experimental, and the following chemicals were used: Amoxicillin
trihydrate and Cephalexin monohydrate with a purity percentage of over 95% provided

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from Jaber Ibn-Hayan pharmaceutical company (Tehran, Iran), titanium dioxide

nanoparticles (of anatase type with Code US3490 with a purity percentage of over 99.5%
and size of 10-25 nm), zinc oxide nanoparticles (of anatase type with Code US3590 with a
purity percentage of over 99.5% and size of 10-30 nm) purchased from US-Research
Nanomaterials (America-Texas), acetonitrile, triethylamine, methanol, citric acid,
phosphoric acid, boric acid, and NaOH from Merck Company, Germany.
Amoxicillin is a wide range of the penicillin group of antibiotics. It is activated against
many gram-positive and gram-negative bacteria. The formula is C16H19N3O5S.3H2O and
its molecular weight is equal to 419.45, whose molecular structure is as follows [13, 14].

Figure 1. Amoxicillin chemical structure (www.antibiotics-info.org) [15]

Cephalexin is an oral medication, which is considered the first generation of antibacterial

cephalosporin. The formula of this antibiotic is hydrated C16H17N3O4S and its molecular
weight is equal to 365.4, whose molecular structure is as follows [16].

Figure 2. Cephalexin chemical structure (www.antibiotics-info.org) [15]

The properties of the mobile phase to measure the residual concentration of the antibiotics
were as follows: 30% acetonitrile and 0.025 KH2PO4 70% M for Amoxicillin. 225 ml
distilled water, 24.6 ml acetonitrile, 12.3 methanol, and 3.7 ml triethylamine for
Cephalexin.

2.2. Apparatuses
To measure the pH, an experimental pH-meter device (BASIC20, Switzerland) was used,
while to evaluate the residual of the antibiotics, a spectrophotometer device (Hach
DR5000, Germany) and an HPLC device (KNAUER, Germany) were used along with UV
detector and C18(4.6*250ml).

2.3. The procedure of the experiment

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This study was experimental and the sampling method had been manual and daily. First,
the stock solution 100 mg/L of each antibiotic with distilled water was prepared on a stirrer
at 500 rpm at a constant temperature within the mixing time of 2 hours. Thereafter,
standards were prepared from the stock solution with the concentrations of (1, 5, 10, 15,
20, 50 and 100 mg/L). By adjusting the intended pH (3, 5, 7, 9 and 11) by acetic acid,
phosphoric acid, boric acid, and NaOH 2 M and considering the times (3, 5, 15, 30, 45 and
60 min), they were poured into 1-L balloons. They were then placed on a shaker at 350
rpm inside an ultraviolet pilot to be mixed with different amounts of nanoparticles (0.2, 1,
1.4, 2, 3 and 4 mg/L), once with a power of 6 W and in other time with 18 W. After the
mentioned duration, the samples were passed through syringe filters (size= 0.22 µm). At
each stage, by changing one parameter and keeping other parameters constant.

2.4 XRD and SEM analysis

The results obtained from SEM and XRD for titanium dioxide nanoparticles and SEM
results for zinc oxide nanoparticles, as provided below, were prepared by the manufacturer
company of the nanoparticles (US-Research Nanomaterials Company).

a b

Figure 3. SEM images of Zinc Oxide (a) and Titanium Dioxide nanoparticles (b)
(www.us-nano.com) [17]

Figure 4. XRD image of Titanium Dioxide nanoparticle (www.us-nano.com) [17]

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3. Calculation
Initially, the maximum absorbed wavelength was obtained at 228 and 261 nm for
Amoxicillin and Cephalexin, by the spectrophotometer device. Thereafter, the
calibration curve for Amoxicillin and Cephalexin were plotted in Excel by using the
absorption numbers of discrepant concentrations of the antibiotics.

The removal percentage (E) of Amoxicillin and Cephalexin is measured was follows:

Here, C0 and Ce were the initial and final equilibrium concentration of Amoxicillin or
Cephalexin (mg/L) in aqueous solution, respectively [18].
The removal percentage of the antibiotics was calculated by the spectrophotometer device.
In the end, for the accuracy of the obtained results, the samples were measured by liquid
chromatography (HPLC) under optimal conditions.

3. Results and discussion

3.2. The effect of contact time
The results of investigating the effect of time is presented in Diagram 5. As can be
observed in the diagram, for the removal of Amoxicillin by titanium dioxide and zinc
oxide nanoparticles, the removal trend is ascending until 15 min, but from 15 to 60 min,
this trend becomes descending. On the other hand, for Cephalexin until 45 min, the
removal trend has been increasing whereby the removal percentage reaches a peak. After
that, a trivial descending trend is observed until 60 min. Kord Mostafapour et al., (2016)
reported 60 min as the optimal time in photocatalytic degradation of ciprofloxacin using
copper oxide from aqueous environments. Sadat Najafi et al., (2013) obtained 180 min in
removing metronidazole using TiO2 exposed to ultraviolet radiation as the optimal contact
time. Dimitrakopoulou et al., (2012) stated 25 and 90 min as the reaction time for the
optimal values of 10 and 250 mg/L of titanium dioxide catalyst in removing Amoxicillin,
respectively [9, 11, 12].

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Figure 5. Effect of time on the degradation efficiency of AMX and CPX

under UV/ZnO or UV/TiO2 processes Ads=1gr/L، Antibiotics Con= 5
mg/L, Radiation Intensity= 6 watt, Time= 3, 5, 15, 30, 45 and 60 min

3.3. The effect of the amount of adsorbent

The results of investigating the effect of the amount of adsorbent is demonstrated in
Diagram 6. As can be viewed in the diagram, with the elevation of the amount of titanium
dioxide and zinc oxide nanoparticles until 1 g/L, the removal percentage of Amoxicillin
and Cephalexin is increasing, while at 1.4 g/L, a minor reduction of removal is observed.
Thereafter, from 1.4 to 3 g/L, the removal percentage is climbing and reaching a peak.
Next, until 4 g/L, this trend is descending. Jain et al., (2017) managed to remove 85% of
Rifabutin antibiotic from aqueous environments using titanium dioxide nanoparticles in the
presence of ultraviolet radiation at the optimal value of 0.06 g/L. Kord Mostafapour,
(2016) observed that the maximum efficiency of the system as 73% for photocatalytic
degradation of ciprofloxacin using copper oxide at the optimal value of 0.07 g/L.
Dimitrakopoulou et al., (2012) obtained 10 and 250 mg/L as the optimal absorbent value
for titanium dioxide [8, 9, 12].

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Figure 6. Effect of adsorbent quantity on the degradation efficiency of

AMX and CPX under UV/ZnO or UV/TiO2 processes Time (AMX)
=15min and (CPX) =45min, Antibiotics Con= 5 mg/L, Radiation
Intensity= 6 watt, Ads= 0.2, 1, 1.4, 2, 3 and 4 gr/L

3.4. The effect of pH

The results obtained from investigating the changes of pH on the removal efficiency of
antibiotics is illustrated in Diagram 7. As can be noticed, the suitable pH for removing
Amoxicillin by the titanium dioxide and zinc oxide nanoparticles is 5. Considering
Cephalexin, with the elevation of pH from 3 to 7, the removal percentage rises in both
catalysts, with the most suitable pH being the neutral pH, and from 7 to 11, the extent of
removal declines. Jain et al., (2017) obtained the pH of 10.5 as the optimal pH in removing
Rifabutin antibiotic using titanium dioxide nanoparticles with the presence of ultraviolet
radiation. . Kord Mostafapour, (2016) obtained the optimal pH as 7. Akbari et al., (2014)
obtained the maximum removal efficiency for doxycycline as 90.24% using titanium
dioxide nanoparticles at the pH of 6.5. Dimitrakopoulou et al., (2012) concluded that pH
was not an influential factor in the removal efficiency [8,9,10,12].

Figure 7. Effect of pH on the degradation efficiency of AMX and CPX

under UV/ZnO or UV/TiO2 processes Time (AMX) =15min and (CPX)
=45min, Ads=2gr/L, Antibiotics Con= 5 mg/L, Radiation Intensity= 6
watt, pH= 3, 5, 7, 9 and 11

3.5. The effect of the concentration of antibiotics

The results obtained from investigating the effect of concentration of antibiotics is
presented in Diagram 8. As can be observed, for the removal of Amoxicillin and
Cephalexin by the titanium dioxide and zinc oxide catalysts, with increasing the

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concentration of antibiotics from 1 to 15 mg/L, the extent of removal increased, after

which at higher concentrations it diminishes. Jain et al., (2017) managed to remove 85% of
Rifabutin antibiotic using titanium dioxide nanoparticles in the presence of ultraviolet
radiation at the optimal concentration of 0.4 mg/L. Akbari et al., (2014) calculated
doxycycline removal percentage as 90.24% at the initial concentration of 20 mg/L. Sadat
Najafi et al., (2013) obtained the optimal concentration of metronidazole using TiO2 under
ultraviolet radiation as 20 mg/L [8, 10, 11].

Figure 8. Effect of Antibiotics Concentration on the degradation

efficiency of AMX and CPX under UV/ZnO or UV/TiO2 processes Time
(AMX) =15min and (CPX) =45min, Ads=2gr/L, pH (AMX) =5 and
(CPX) =7, Radiation Intensity= 6 watt, Antibiotics Con= 1, 5, 10, 15, 20,
50 and 100 mg/L

3.6. The effect of radiation intensity

The results obtained from investigating the effect of radiation intensity is presented in
Diagram 9. As can be perceived in the diagram, the degradation of Amoxicillin and
Cephalexin by the titanium dioxide and zinc oxide nanoparticles in the presence of
ultraviolet lamp is higher at the power of 18 W, compared to 6 W. Akbari et al., (2014)
achieved the removal percentage as 90.24 with radiation intensity of 17 W [10].

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Figure 9. Effect of radiation intensity on the degradation efficiency of

AMX and CPX under UV/ZnO or UV/TiO2 processes Time (AMX)
=15min and (CPX) =45min, Ads=2gr/L, pH (AMX) =5 and (CPX) =7
،Antibiotics Con= 15 mg/L, Radiation Intensity= 6 and 18 watt

4. Conclusions
In this investigation, titanium dioxide and zinc oxide nanoparticles were used for the
removing of Amoxicillin and Cephalexin. The optimal conditions for enhancing the
removal efficiency for Amoxicillin and Cephalexin in the photocatalytic process included:
pH of 5 and 7, contact time of 15 and 45 min, absorbent value of 2 g/L, radiation intensity
of 18 W, respectively. Actually, the zinc oxide proved a better performance than titanium
dioxide nanoparticle in the removal extension and the maximum removal efficiency under
optimal conditions for Amoxicillin with titanium dioxide and zinc oxide nanoparticles was
27.6 and 48.6%, respectively. Considering Cephalexin, the respective values have been
63.5 and 81.8%.
Based on the above results, it can be concluded that the extent of removal had descending
over time until reaching a specific point, after which a diminishing trend occurred in the
removal process. This can be due to sorption and desorption and incomplete solubility of
nanoparticles. At high absorbent values, the extent of removal was declined, which can be
due to decreased light diffusion, light scattering, or aggregation and precipitation of
catalysts at
high concentrations. Indeed, the reason behind the superior removal in acidic environments
or close to neutral pH could be attributed to the tendency of absorbing positive charge by
the antibiotics at a low pH. Under these conditions, the positive charge of the environment
increases and due to the changes in the structure of antibiotics, it makes their removal. In
addition, in aqueous environments, catalysts tend to agglomerate, which is dependent on
ionic tension, pH, and suspension. They less tend to agglomerate in acidic environments
when compared to a neutral state, whereby the specific surface area of the catalyst grows.

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Thus, by adjusting pH in acidic environments or close to neutral environments, with the

elevation of the specific surface area of catalysts, the removal efficiency rises due to
further contact. The reason behind the gradual reduction of degradation with expansion of
the contaminant concentration is because of the reaction rate. Indeed, it is higher due to
low absorption of pollutants on the active sites of the photocatalyst at low concentrations.
On the other hand, at high concentrations, due to the occupation of all active sites of the
photocatalysts, the mass transfer becomes restricted, thereby reducing the extent of
removal. The drug degradation in the presence of photocatalyst is mostly dependent on the
active genus produced (hydroxyl radical, hole, superoxide ion) in the process. Based on the
results of this research, production of hydroxyl radical at 18 W had been higher, and thus
the removal efficiency was greater.
Based on the obtained results which suggest the high performance of UV-TIO2/ZnO
photocatalytic processes, it is recommended that the efficiency of this method be
investigated using strong oxidants such as hydrogen peroxide along with the main catalysts
in this experiment. Furthermore, the temperature and dissolved oxygen could also be taken
into account as parameters in the experiments.

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[17] Hassani AH, Torabian A, Rahimi Kh. Performance of Iron-Zero (nZVI) nanoparticles in the
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