INTERIM REPORT

Maroun Semaan Faculty of Engineering and Architecture

Department of Chemical and Petroleum Engineering
CHEN 499 – Undergraduate Research

Submitted by: Natalia Wehbi & Mohamad Ardati

Date: March 6th, 2019
Abstract
Micropollutants, denoted as emerging contaminants, have raised concern due to their
increasing concentration present in the water system. These contaminants include personal care
products (PCPs), pesticides, surfactants, and other potentially harmful chemicals.
Pharmaceutically active compounds (PhACs) in specific have been under increasing concern
due to the potential health risks that could result from the increasing concentrations. Traditional
drinking and wastewater treatment facilities are not sufficient in the removal of PhACs and
therefore the application of alternative technologies must be investigated. Membrane
separation processes (MSPs) are the leading technologies in this field and are known to have
high efficiencies concerning the removal impurities. The MSP of interest is the pressure-driven
nanofiltration system which is characterized by its high rejection rates and when compared to
reverse osmosis, displays lower energy consumption and higher permeate fluxes. The
nanofiltration membrane separation process is governed by three main mechanisms: size
exclusion, electrostatic interactions, and adsorption; however, the mechanisms may be affected
by several factors including the salinity, pH, and temperature of the influent. On the other hand,
the implementation of NF on PhACs could be subject to drawbacks as well. This includes the
fouling of the membrane, the disposal of the resulting concentrate, and variation of
performance with different PhACs. This report also includes rough preliminary data that was
obtained from recent experiments concerning this topic.
Table of Contents
1 Literature Review .......................................................................................................... 1

1.1 Introduction ............................................................................................................ 1

1.2 Nanofiltration.......................................................................................................... 2

1.2.1 Mechanisms ..................................................................................................... 3

1.2.2 Effects of Salt .................................................................................................. 5

1.2.3 Effects of Temperature ..................................................................................... 5

1.2.4 Drawbacks of Nanofiltration ............................................................................ 6

1.3 Pharmaceuticals ...................................................................................................... 8

2 Results .......................................................................................................................... 9

References .......................................................................................................................... 10

Table of Figures
Figure 1: Characteristics of carbamazepine, ibuprofen, and diclofenac .................................. 8
Figure 2: The effect of temperature and salt concentration on the rejection of carbamazepine 9
Figure 3: The effect of temperature and salt concentration on the rejection of ibuprofen........ 9
1 Literature Review

1.1 Introduction
Chemical pollutants that have been recently detected in water supplies include pharmaceutical and
personal care products (PPCPs), pesticides, endocrine-disrupting chemicals (ECDs), and surfactants
[1, 2]. These pollutants have been denoted as “contaminants of emerging concern” or “emerging
contaminants”. Urbanization has led to the rise in concentration of these chemicals surface water,
ground water, wastewater effluent streams, and even throughout stages of drinking water plants [1, 2,
3]. Emerging contaminants are of great concern because the levels in which they are detected in the
aquatic environment could have potential toxicological effects on both aquatic life and human health
[2, 4]. In recent years, pharmaceutical active compounds (PhACs) have been under specific
observation since their use is increasing yearly, they are naturally biologically active, and the total
effect they have on the environment is not yet determined [3]. PhACs presence in the water system
results from wrongful disposal, leachate from landfills, water drainage, human excrements (sewage),
and industrial waste [5]. While recent studies report that PhACs are currently present in the
environment at low concentrations ranging between ng/l to µg/l, the increasing consumption and
production will only allow these numbers to increase. Moreover, the World Health Organization
(WHO) reported that these trace amounts raise concern about the health risks they may potentially
cause to humans [6]. The traditional wastewater and drinking water treatment facilities have been
unsuccessful in the removal of PhACs which is mainly due to their polarity, making them particularly
soluble in water, and their small size [7, 8]. Archer et al. [5] reported that due to the behavior of PhACs
through these processes, they transform into conjugates which allows the concentration of the effluent
in wastewater plants to be was overall higher than the influent. In addition, some contaminants such
as beta-blockers, anti-inflammatories, and anti-epileptic drugs were shown to have removal
efficiencies below 20% in traditional wastewater treatment plants, which increases the chance of their
accumulation [8].

In order to effectively remove pharmaceuticals from water, exploration on the application of

alternative technologies for such processes is necessary. Leading technologies include membrane
separation processes (MSP) which are characterized by their high efficiency when removing
contaminants, such as salt, heavy metals, and organic matter, and are thus expected to have the same
effect on PhACs and other emerging contaminants [7]. These MSPs include processes such as forward
osmosis (FO), membrane bioreactors (MBR), microfiltration (MF), ultrafiltration (UF), nanofiltration

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(NF), and reverse osmosis (RO) [7, 6]. Membrane filtration techniques are pressure-driven and enable
the removal of micropollutants through three main mechanisms: size exclusion, electrostatic repulsion,
or adsorption [6]. The most popular techniques used in the removal of pharmaceuticals from water are
reverse osmosis and nanofiltration. RO membranes have superior pollutant retention when compared
to NF, at the cost of higher operating pressures, and lower permeate flux. NF membrane techniques
are seen as cheaper alternatives to the use of RO in the removal of pollutants from water [9].

1.2 Nanofiltration
NF membranes are recognized as a reliable technology for water reuse, especially in processes where
the complete removal of ions is not necessary [8]. Nanofiltration membranes may contain small pores
or nanovoids. Nanovoids are the transition point between dense membranes (such as RO) and
microporous membranes, and are present in the range of 0.5-1 nm [10]. These membranes are typically
advantageous in their lower operating pressure of 5-10 bar for brackish water, compared to 20+ bar in
RO.

The majority of NF membranes are produced using multiple layers of synthetic or natural polymers.
The thin upper layer is the active layer which determines some characteristics of the membrane, most
importantly surface charge. The membrane selected for this paper are the NF-270 membranes which
have an ultrathin polyamide active layer on top of a porous polysulfone layer [11]. These membranes
are both charged and porous, and are considered as a hybrid between the filtration mechanism of
Ultrafiltration membranes and osmotic mechanism of RO membranes [12].

Similarly to all other membrane processes, certain transport phenomena govern the movement of the
species across the NF membrane. The first phenomena involves the transport of species through the
membrane, which is governed by the membrane type, thickness and permeability. The second
phenomena relates to the transport of the species to the membrane surface, which produces what is
called a concentration polarization layer. Concentration polarization is the increase in concentration of
solutes near the surface of the membrane compared to the bulk concentration. This is mainly a result
of the retention of solutes by the membrane and the permeation of the solvent which produces a layer
of higher concentration called the polarized layer [13]. Concentration polarization leads to higher
membrane resistance, which in turn provides higher rejection on the account of lower permeate flux.
However, a very concentration barrier could cause scaling and pore blockage to occur, deteriorating
the performance of the membrane. Concentration polarization can also be used to explain the rejection
behavior of certain pharmaceuticals that adsorb on the membrane or are attracted electrostatically to

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the surface. Since electrostatic mechanisms create a tendency for the molecules to be at a closer
position to the charged surface, and the adsorption of molecules at the surface both contribute to
increasing the concentration of these molecules, a polarized layer is formed. Consequently, the
concentration polarization phenomenon is created, and higher membrane resistance is observed.

1.2.1 Mechanisms
NF membranes are theorized to use several complex mechanisms through the removal of PhAC’s from
water. Several studies have identified these mechanisms as steric effect, electrostatic repulsion,
hydrophobic interactions, partitioning and diffusion, which ultimately depend on the physicochemical
properties of the membrane, the solutes, and the solution [7]. In general, these mechanisms can be
grouped into size exclusion, electrostatic repulsion, and adsorption.

1.2.1.1 Size Exclusion

The first mechanism involves the steric hindrance of pollutants by size exclusion, which is purely the
physical blockage of the organics, with no regard to other properties. This mechanism is especially
useful for the retention of uncharged and non-adsorptive organic solutes. The observed retention for
these types of materials can be predicted using the pore transport model described by Ngheim et al.
[14]. In addition, Ngheim et al concluded the retention of carbamazepine, a neutrally charged
compound, was solely governed by steric size exclusion [14]. Since the membrane can be thought of
as interconnected chains of polymers, where the effective pore size between these strands acts as a
barrier for larger molecule sizes [9].

According to a doctorate thesis by Kevin Terry Cliff [15], swelling occurs when the polymer
membrane is subjected to certain solvents that would soak up into the polymer structure and expand
it. The effective pore size, or the actual membrane pore size during the process, in porous
membranes usually decreases, due to the constriction caused by the expanding polymer material,
which in turn increases rejection characteristics. However, swelling increases the free volume
throughout a dense membrane, which in turn lower rejection. It was noted by Geens et al. and by
Shukla and Cheryan that water usually had the greatest swelling effect between multiple solvents
tested [15].

Molecular weight cut-off (MWCO) is a term used to identify the minimum molecular weight of a
molecule which the membrane rejects 90% of the solute [16]. The MWCO is measured in units of
Daltons (Da) where one dalton is defined as one twelfth the mass of an unbound neutral atom of
carbon-12. The MWCO of NF membranes is typically between 200 and 1000Da, which is small

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enough to reject most divalent ions [10]. Most common PhACs lie between 210 to 830 Da, which is
within the MWCO range of NF membranes [17].

1.2.1.2 Electrostatic Interactions

The thin polyamide layer of the surface of the membrane determines the chemical characteristics of
the NF membrane. This is the active layer of membrane and it contains functional groups which are
both amine and carboxylic which have the potential to ionize [14]. Therefore, the charge at the surface
of the membrane or the zeta potential is ultimately a function of the pH of the solution in which the
membrane is submersed in. The pH at which the membranes charge goes from positive to negative is
known as the isoelectric point. For the NF-270, the isoelectric point is around 3.5, and which below
this value the membrane charge is slightly positive and above is negatively with the negativity
increasing as the pH increases [14]. Resultantly, a major parameter in the removal of PhACs is the
charge of the PhAC molecules and the electrostatic interactions present between it and the membrane
surface. Since under neutral conditions the membrane is negatively charged, positively charged PhACs
will be attracted to the surface of the membrane leading to a concentration increase at the surface and
therefore lower rejections. On the other hand, negatively charged PhACs will be subjected to repulsive
forces decreasing the concentration of the solute at the surface resulting in higher rejection rates [6]
[18]. With an increasingly wide range of PhACs, including those of complex molecular structures in
the water system, it becomes challenging to determine the membrane type for the most efficient
removal.

Negheim et al. [14, 19] studied that electrostatic interactions between both ionizable (ibuprofen) and
non-ionizable (carbamazepine) pharmaceuticals. It was found that the retention of the ionizable PhACs
was dependent on the charge of the solution in which as the pH increased, the more negatively charged
the PhACs became. For non-ionizable PhACs, the retention was not affected by the chemistry of the
solution.

1.2.1.3 Adsorption
Adsorption is the process in which contaminants stick on the surface of the membrane due to physical
or chemical interactions. Physical adsorption is due to charge interaction and is usually reversible,
while chemical adsorption is due to the bonding of the solute with the molecules on surface of the
membrane and is usually irreversible [20].Trace organics that adsorb on the membrane surface usually
have high hydrogen bonding capacity, quantified by log K . Compounds with high hydrogen bonding
OW

capacity are considered hydrophobic. According to Ngheim et al. [20], the molecules with high

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hydrogen bonding capacity compete with the water molecules to attach to the hydrophilic groups of
the membrane polymer, lowering the water flux across the membrane. Build-up of contaminants
adsorbed to the membrane would cause a concentration gradient build-up and the deterioration of the
membrane.

On the other hand, some compounds adsorbing to the membrane could support the retention of
contaminants. In a study by Kiso et al., the retention for pesticides increased with increasing
hydrophobicity [21].

1.2.2 Effects of Salt

The salinity of the input solution could affect the membrane performance positively or negatively. A
study conducted by Luo & Wan tested the effect of increasing salinity on the retention of glucose using
a 15g/L glucose solution and NF270 membrane [22]. According to this study, glucose retention
decreased with increasing salt concentration, due to the increased interaction of salt molecules with
glucose in the solution, and the membrane media. It is concluded that solutions with higher salt
concentration exhibit higher deviation from predicted performance due to salt affects such as salting-
out, salting-in and pore swelling becoming more pronounced. In addition, the higher salt concentration
increased the osmotic pressure which in turn lowered the permeate flux. On the other hand, a study
showed the increase in salt concentration had a partial positive effect on the rejection of ibuprofen.
The rejection increased with salt concentration, until a point where it peaked and decreased again [2].
Further studies are required to find a proper theory to describe the reason behind the positive impacts
of salt on the removal of certain compounds.

1.2.3 Effects of Temperature

The temperature of the feed solution further complicates the separation process. While it is a key
parameter when discussing mass transfer and membrane processes, most related studies are conducted
at arbitrary temperatures. Previous studies have mostly investigated the effect of temperature on NF
membranes in general, but there is a lack of literature discussing the effect that it has on organic
contaminants such as PhACs [14, 23].

The main effect of temperature observed on membrane separation processes is the increase of permeate
flux, and it has been reported that the relation between temperature and water flux on NF membranes
is linear between certain ranges [23, 24]. This increase in flux is attributed to the thermal expansion of
the membrane polymer with increasing temperature; however, this phenomena also leads to the
decrease in the rejection. It was suggested that the active layer of the membrane consisting of a thin

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polymer expands under increasing temperature leading to the increase in average pore size and
decrease in pore density [25]. The viscosity of the solvent is another parameter that is likely to be
affected by the change of temperature and in turn impact the separation process [24]. While this has
been reported repeatedly, the impact that the temperature has on organic contaminants is also of
significance, yet this topic has been generally neglected.

Dang et al. [23] reported that the temperature increase did reveal an increase in average pore radius
and is a major factor in the increase of permeability. In addition, this increase in permeability coincided
with an increase in the diffusion coefficient and resultantly the decrease in the rejection of organic
contaminants. However, it was observed that the PhACs that were previously effectively removed by
the NF-270 membrane reveal minimal effects in rejection with relation to temperature. Due to the fact
that these PhACs are negatively charged, it was concluded that this was due to the electrostatic
repulsion being the main mechanism of removal and thus pore size does not play a significant role. On
the other hand, there were negatively charged PhACs in which their rejection was affected by
temperature, but these had previously show only moderate removal prior to the temperature change.
Neutral PhACs were reported to be most affected by the increase of membrane pore size [23].

The effect of temperature and salt simultaneously also significantly impacts the separation process.
Nilsson et al. [26] conducted a study on the effect of both temperature and salt effects on NF and
reported that the degree of swelling of the membrane increased due to the increase of polymer
flexibility. In addition, the rejection of the negatively charged salt was marginal due to the charge
effect.

1.2.4 Drawbacks of Nanofiltration

Reverse osmosis membranes have been reported to being the most effective in the removal PhACs;
however, NF draws more attention for the removal of emerging contaminants due to the lower energy
requirements, greater permeate flux, and incomplete removal of ions, which is not seen as necessary
for these applications [7]. While this has been proven true in lab scale experiments, at the pilot scale
level, the flux significantly decreased due to effluent organic matter fouling [27].

At the lab scale, most experiments have been conducted with the use of virgin membranes and
deionized water that has been spiked with target solutions. This neglects the water matrix effects and
the changes in the properties of the membrane which is crucial for the success of pilot-scale and
eventually full-scale processes [27]. Fouling in specific is the main problem with membrane processes,
and specifically with NF because the fouling occurs as the nanoscale and is therefore difficult to fully
understand. It can be the result of various impurities in the feed, such as organic and inorganic solutes,

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colloids, and biological solids [28]. Depending on impurities present, different types of fouling may
occur including the buildup of a cake, the precipitation of salts or scaling, or biofouling which is the
formation of biofilm attached to the membrane surface. This leads to the decrease in flux due to the
inhibition of the membrane rejection mechanisms such as the decline in the surface charge that was
reported by Mahlangu et al. [29]. However, they can be avoided or delayed through the use of
pretreatment process and effectively cleaning the membrane surface [28].

In addition, the treatment of the concentrate is a controversial issue across membrane processes. Since
these processes do not destroy or transform the impurity, throughout the process the buildup and an
unwanted and potentially harmful concentrate solution is generated [7, 29]. In addition to PhACs, this
concentrate may also include chemicals that were initially used in the pretreatment process, such as
antiscalants. The discharge of the concentrate result in the following possibilities: reuse, further
treatment, incineration, landfilling, or the direct or indirect disposal in surface water or groundwater.
This topic is highly controversial with both legal and ethical parameters that must be accounted for in
addition to the cost of further treatment [29].

The performance of nanofiltration membranes on PhACs varies between each type of PhAC ranging
from rejections of 0% to greater than 90% [7]. Radjenovic et al. [30] performed an experiment on
twelve different pharmaceutical products. Nine out of twelve of the pharmaceuticals resulted in
rejection rates greater than 95% and the other three were reported to have only slight rejections (~50%).
The lower rejections were concluded to be due to the hydrophilic behaviors and/or the low molecular
weights of the component [30]. This wide variation of performance brings to question the effectiveness
of NF on the removal of PhACs.

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1.3 Pharmaceuticals
The following PhACs are commonly used when studying the application of NF on PhACs. The
characteristics of each are displayed below.

Pharmaceutical Carbamazepine (CBZ) Ibuprofen Sodium Diclofenac Sodium

(IBF)
Structure

Class Anticonvulsant Analgesic Analgesic

(NSAID) (NSAID)
Molecular Weight 236.274 g/mol 228.267 g/mol 318.129 g/mol
Molecular C15H12N2O C13H17NaO2 C14H10Cl2NNaO2
Formula
Charge in Water 0 -1 -1
Functional Groups Carboxamide, Carboxylic Carboxylic
Dibenzazepine Acid Acid
derivative
Log Kow 2.45 4.51 3.97
Figure 1: Characteristics of carbamazepine, ibuprofen, and diclofenac

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2 Results
The effect salt concentration and temperature on the removal of pharmaceuticals using nanofiltration
membrane is currently being studied. The feed is dosed with NaCl at four different concentrations (0,
300, 2000, and 8000 ppm) and 100ppm of a pharmaceutical, either carbamazepine (CBZ), ibuprofen
(IBF), or diclofenac (DCF). The study is being conducted at two different temperature, 20℃ and 30℃,
in which the temperature is regulated using a chiller. The following are the results obtained so far.

CBZ REJECTION 20 VS 30
100.000%

90.000%

80.000%
REJECTION

70.000%

60.000%

50.000%

40.000%
0 1000 2000 3000 4000 5000 6000 7000 8000 9000
NACL CONC (PPM)
T = 30C (a) T = 30 (b) T = 20C (a) T = 20C (b)

Figure 2: The effect of temperature and salt concentration on the rejection of carbamazepine

IBF REJECTION 20 VS 30
110.00%
100.00%
90.00%
REJECTION

80.00%
70.00%
60.00%
50.00%
40.00%
0 1000 2000 3000 4000 5000 6000 7000 8000 9000
NACL CONC (PPM)
T = 30C T = 20C

Figure 3: The effect of temperature and salt concentration on the rejection of ibuprofen

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