JID: JTICE

ARTICLE IN PRESS [m5G;October 14, 2017;19:19]

Journal of the Taiwan Institute of Chemical Engineers 0 0 0 (2017) 1–13

Contents lists available at ScienceDirect

Journal of the Taiwan Institute of Chemical Engineers

journal homepage: www.elsevier.com/locate/jtice

Characterizations of surfactant synthesized from palm oil and its

application in enhanced oil recovery
Neha Saxena a, Nilanjan Pal a, Swapan Dey b, Ajay Mandal a,∗
a
Enhanced Oil Recovery Laboratory, Department of Petroleum Engineering, Indian Institute of Technology (ISM), Dhanbad 826 004, India
b
Department of Applied Chemistry, Indian Institute of Technology (ISM), Dhanbad 826 004, India

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

Article history: The present work deals with synthesis of an anionic biodegradable surfactant for application in chemical
Received 19 January 2017 enhanced oil recovery (EOR) process. Alpha sulfonated ethyl ester (α -SEE) was synthesized from palm
Revised 12 September 2017
oil via trans-esterification process. The surfactant was characterized by FTIR, GC, TGA, FE-SEM and EDX
Accepted 12 September 2017
analyses. Critical micelle concentration (CMC) was determined by surface tension measurement at air–
Available online xxx
aqueous interface. The efficiency of α -SEE was studied by calculating the interfacial tension (IFT) between
Keywords: crude oil and surfactant solution, and by investigating the ability of the surfactant to alter the wettabil-
Palm oil ity nature of carbonate and quartz surfaces. Salt effect was studied at CMC of surfactant to obtain an
Surfactant synthesis ultra-low IFT value of the order of 10−3 mN/m at optimal salinity. Addition of organic alkali also showed
Surface tension synergistic effect on IFT between crude oil and surfactant solution. The surfactant favorably altered the
Interfacial tension wettability of oil-wet carbonate and quartz surfaces to water-wet, which is desirable for oil recovery. The
Contact angle
surfactant showed potential application in EOR owing to its enhanced interfacial properties and rock-
Enhanced oil recovery
wetting characteristics. Flooding experiments were conducted with surfactant slugs at different α -SEE
concentrations to achieve about 25%–27% additional oil recoveries after conventional flooding.
© 2017 Taiwan Institute of Chemical Engineers. Published by Elsevier B.V. All rights reserved.

1. Introduction
The global energy demand is highly dependent on oil and gas
extraction in the face of current energy needs. Since 2013, it be-
came impertinent for petroleum industry to demand and develop
better techniques for improving oil production. In the present sce-
nario of low crude oil price, there are a few limitations of en-
hanced oil recovery techniques as a consequence of high project
cost and longer lead time periods. Enhanced oil recovery is a
strained and costly affair in less accessible areas, thereby paving
the necessity to extract oil by employing more economical and ef-
fective methods. Traditionally oil recovery techniques follow pri-
mary, secondary and tertiary (EOR) processes [1,2]. Among these
recovery processes, chemical flooding with polymers and surfac-
tants is gaining importance because of its high potential to extract
oil that is otherwise not recoverable by primary and secondary re-
covery [3]. However, as the most of the oil in existing reservoirs
are now matured with lower production rates, it is the right time
to develop cost effective EOR techniques which can be applied ef-
ficiently in the oil field with existing facilities [4]. Surfactants are
∗
Corresponding author.
E-mail address: ajay@iitism.ac.in (A. Mandal).
chemicals that are known for their use in detergents, cosmetics
and textile sectors [5,6]. Surfactants reduce the interfacial tension
between the injected water and the crude oil trapped in the reser-
voir to an ultra-low value. Recently, much attention is given on use
of biodegradable and environmental-friendly surfactants in oil re-
covery application [7,8].
Several efforts are being made to develop low cost chemicals
from natural resources for successful application in chemical en-
hanced oil recovery [9]. Bio-enzyme catalyzed esterification is em-
ployed to synthesize fatty acid esters from vegetable oils like cas-
tor oil, Jatropha oil [10,11]. The efficacy of the chemicals in oil re-
covery processes is dependent on capillary pressure, permeability
and wettability of rocks and interfacial tension. Though substantial
amounts of oil are extracted by the injection of surfactant solu-
tions in chemical enhanced oil recovery, some oil still remain in
the rock pores [12]. This is because of high interfacial tension be-
tween the oil water interface which traps the oil droplets by capil-
lary forces. Surfactants help in lowering the interfacial tension be-
tween the oil and water phases, and alter the wettability of the oil-
wet reservoir rock to water-wet [13,14]. Surfactant selection plays
a pivotal role in achieving cost-effectiveness and favorable interfa-
cial properties in EOR processes. Polyethylene glycol based esters
are generally produced by chemically catalyzed esterification pro-
cesses. However the yield of product is not satisfactory in such

https://doi.org/10.1016/j.jtice.2017.09.014
1876-1070/© 2017 Taiwan Institute of Chemical Engineers. Published by Elsevier B.V. All rights reserved.

Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
JID: JTICE
ARTICLE IN PRESS
2 N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13
Table 1
Properties and composition of Palm oil.
Palm oil properties Fatty acid constituents of palm oil
Properties @ 27 °C Value Fatty acid Constituents (%)
Acid value (mg KOH/g) 11.34 Oleic 37.0
Density (g/cc) 0.912 Linoleic 10.0
Viscosity (cap) 42.08 Palmitic 42.0
Saponification value (mg KOH/g) 202.7 Stearic 6.6
Myristic 1.7
Free fatty acid 2.7
reactions and also proceeds toward undesirable side products
[15,16]. In recent decades, esterification reactions carried out in the
presence of biocatalysts viz. enzymes which include lipases, hy-
drolases, etc. attracted the attention of scientists and researchers
for synthesizing fatty acid esters of selective fatty acid and polyol
systems. The catalytic action of lipases to catalyze fatty acids was
investigated by Hayes in different studies [17–20]. According to
Hayes (1992) the hydroxyl group present on the fatty acid chain
is subject to the catalytic action of lipases, and the length of acid
chain has a minor effect on the reaction mechanism [17]. Ziemann
and Wagner [21] synthesized wax esters of trihydroxy palmitic acid
by Rhizomucor miehei and obtained moderate yields. Lang et al.
[22] studied the laboratory synthesis of wax esters of 17-hydroxy
and 3-hydroxy stearic acids using lipase as catalyst and found that
the reaction rates were higher using Mucor miehei as the biocat-
alyst. Steffen and co-workers [23] also applied the same method
to synthesize monoglycerides of 17-hydroxy and 12-hydroxy stearic
acids to achieve higher yields with R. miehei.
The objective of this study is to synthesize an anionic surfac-
tant from palm oil which can be used in the field of enhanced
oil recovery. The chemical and morphological structure of α -SEE
was confirmed by FTIR, GC, TGA and FE-SEM and EDX. Surface ten-
sion studies were conducted in order to determine the CMC value
of the synthesized surfactant. The interfacial tension at surfactant
solution–crude oil interface and contact angle variation of surfac-
tant solution on quartz and carbonate rock with time were also
measured to study the efficacy of the α -SEE surfactant. The α -SEE
surfactant is expected to be green and biodegradable nature. The
enhanced oil recovery by injection of small pore volume of surfac-
tant slug after conventional water flooding were also investigated
by performing flooding experiments.
2. Materials and experimental methods
2.1. Materials required
Palm oil used in the synthesis of the sulfonated ester was pro-
cured from the local market. Its properties and composition are
shown in Table 1. The enzyme lipase from R. miehei was obtained
from Sigma Aldrich. Poly ethylene glycol 600 was obtained from
Loba chemicals. Chlorosulfonic acid, sodium carbonate anhydrous,
sodium bicarbonate, diethyl ether, petroleum ether, ethyl acetate
and pyridine were procured from Merck (India). The crude oil used
in the experiments was procured from Oil India Limited, Assam.
The obtained crude oil has a total acid number 0.84 mg KOH/g,
gravity of 18.9° API, density of 0.9244 g/cc and viscosity of 4.26 cp
at 27 °C.
2.2. Synthesis method
Esterification reaction: Palm oil and poly ethylene glycol (PEG)
600 were weighted in stoichiometric amounts in a round bot-
tom flask, mixed with constant stirring and the reaction mixture
was heated at a temperature of around 60 °C for about 30 min.
Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
[m5G;October 14, 2017;19:19]
Lipase was added subsequently to the reaction mixture 10.0%
(w/w) of the starting material [6]. The reaction mixture was con-
stantly stirred for 48 h and, in between, the progress of the reac-
tion was monitored by checking the TLC (Thin Layer Chromatogra-
phy) in a mixture of petroleum ether-ethyl acetate (70:30) as mo-
bile phase. Excess lipase was filtered off. Fatty acid residue was
removed by washing with a mixture of diethyl ether and a small
amount of sodium bicarbonate solution. The lipase-catalyzed es-
terification of palm oil in the presence of polyethylene glycol (PEG
600) aids in conversion of free fatty acids present in oil into ester.
The remaining solution was evaporated under vacuum and a light
yellow semi-viscous liquid (compound 1) was obtained.
Sulfonation reaction: The product (compound 1) obtained in es-
terification reaction was used to synthesize the desired product
(α -SEE) by sulfonation of palm oil ethyl ester. In this reaction,
chlorosulfonic acid (2.89 g) was added to pyridine (10.0 mL) in a
round bottom flask. The reaction was carried out in ice bath un-
der constant stirring for 30 min. Then, the reaction mixture was
heated to 60 °C till a clear solution was obtained. The solution
was then quenched with a saturated solution of sodium carbon-
ate and sodium bicarbonate in a separating funnel. Normal butanol
(30 mL) was poured into the separating funnel to dissolve the com-
ponents which remained unreacted in the organic layer to obtain
the desired product in aqueous layer and heated to temperature
of 120 °C to remove water and pyridine from desired sulfonated
product. Organic impurities from the final sulfonated product were
removed by washing it with petroleum ether twice. The final white
solid product (compound 2) was obtained by vacuum drying the
product at 60 °C for 24 h which was characterized with FTIR and
GC. The palm oil used in the synthesis chiefly contains oleic acid,
palmitic acid along with small amount of linoleic acid, myristic and
stearic acid, hence, the resultant surfactant formed in the process
is a mixture of the sulfonated ester.
2.3. Reaction scheme of α -SEE
Fig. 1 shows the reaction mechanism for the synthesis of α -SEE.
The fatty acid was first esterified in presence of lipase by cleavage
of ethyl group from PEG which gets attached to the oxygen atom
of fatty acid to form ethyl ester. In sulfonation step, the pyridine
was added as it abstracts the α -hydrogen of the ester group, being
the most reactive site for the reaction to take place efficiently as
compared to other available reactive sites like unsaturation present
in fatty acid. The sulfonate group is attached to α -position of ester
group.
2.4. Characterization of α -SEE by FTIR, GC, TGA, FESEM analyses
The FTIR analysis was done by Perkin Elmer-Spectrum 2 spec-
trometer to identify the functional groups present in the newly
synthesized sulfonated ester surfactant from palm oil. A pellet of
synthesized surfactant in combination with KBr was used in FTIR
analysis. The surface structure was analyzed by FE-SEM analysis
using SUPRA-55 ZEISS Germany. The synthesized surfactant was
kept in desiccator for 24 h for removal of moisture and was coated
with gold to obtain better accuracy. Gas Chromatography (Jeol GC-
Mate II) was used to determine the constituents of surfactant syn-
thesized from palm oil. The TGA analysis of α -SEE was done to
determine its thermal degradability by thermo gravimeter analyzer
(Netzsch-STA 449 Jupiter).
2.5. Interfacial and flooding properties of α -SEE surfactant
2.5.1. Surface tension measurements
The surface tension and critical micelle concentration (CMC)
of synthesized surfactant was calculated by using Du Nouy ring
JID: JTICE
ARTICLE IN PRESS [m5G;October 14, 2017;19:19]

N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13 3

Fig. 1. Reaction scheme for the synthesis of α -SEE.

method (KRUSS Easy Dyne, Germany) at 27 °C. Surface tension was
determined for aqueous solutions with different surfactant concen-
trations. Surface tension values for individual samples were mea-
sured three times to ensure the accuracy of results. The measured
value of surface tension of distilled water was 72.3 mN/m at 27 °C.
After each test the platinum ring used in the experiment was
cleaned by acetone and was dried with flame for the next set of
experiments.
2.5.2. Salt tolerance studies
The concentration of salt in surfactant solution at which surfac-
tant starts precipitating is known as salt tolerance of the surfac-
tant. Salt tolerance of α -SEE surfactant solution at CMC value was
measured at 27 °C. Aqueous solutions were prepared by adding
salt in the range of 1% to 12% NaCl to surfactant solution at CMC.
Initially, 1 wt.% NaCl was added to the solution. The mixture was
stirred at 20 0 0 rpm for 15 min. Similar procedure was repeated for
successive salt additions in surfactant solution until surfactant pre-
cipitation occurs.
2.5.3. Interfacial tension measurements
Oil–aqueous interfacial tension values between the surfactant
solutions of different concentrations and crude oil was calculated
by spinning drop tensiometer (SVT 20, Dataphysics) at 27 °C.
The surfactant solutions at various concentrations ranging from
20 0 0 ppm to 12,0 0 0 ppm were used. The α -SEE solution was in-
jected into a capillary tube through a syringe. Progressively, a drop
of crude oil was injected to the tube through rubber septum. The
IFT between the two liquids of different densities was determined
using SVT 20 software. The experiment was conducted at room
temperature at a speed of 30 0 0 rpm for individual sample. The
equilibrium interface tension for surfactant solution is obtained by

Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
JID: JTICE
ARTICLE IN PRESS
4 N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13
Fig. 2. Schematic representation of chemical flooding experimental setup α -SEE solution in sandpack system.
Eq. (1)
σ = ω R ρ / 4
2 3
(1)
where ω represents the angular velocity of the system, R repre-
sents the radius of crude oil droplet, σ is the interfacial tension
between two fluids under consideration and ࢞ρ is the density dif-
ference between surfactant solution and crude oil. The interfacial
tension between crude oil and distilled water interfaces was found
to be 18.0 mN/m at 27 °C.
2.5.4. Contact angle determination
To carry out a study on alteration of wettability of reservoir
rock from oil-wet rock to water-wet rock surface, the contact an-
gle between the newly synthesized surfactant solution and oil-wet
rock surface had been studied using Drop shape Analyzer (KRUSS
DSA 25, Germany) at 27 °C. Precisely controlled tempering and hu-
midity chambers were used to provide a realistic model of the pro-
cess conditions to avoid vibration, air effect and other mechanical
effects. To calculate the contact angle, 5–10 μL of surfactant solu-
tion was taken in the syringe and carefully dropped onto the sur-
face of oil wet rock (carbonate and quartz). The test was repeated
three times to maintain the consistency in the results for individ-
ual samples. Initially, the rock was suitably prepared for wettabil-
ity study by washing it with deionized water, and was then put
into the crude oil for ageing in oven at 65 °C for 15 days. After
being aged for 15 days the oil-wet rock was then vacuum dried
overnight.
2.5.5. Flooding experiments
Sandpack flood tests were employed for the evaluation of the
effectiveness of the synthesized surfactant (α -SEE) to enhance the
oil recovery after conventional water flooding. It consists of four
components viz. a core holder, a displacement pump (Teledyne
Isco), chemical solution cylinder for crude oil, brine and surfactant
solution and a fraction collector. A schematic of the experimental
setup is depicted in the Fig. 2. As per the homogeneous sand pack-
ing model, the geometry was chosen as L = 45 cm and r = 3.5 cm.
The core holder was tightly packed with uniform sands (60 mesh)
and saturated with 2.0 wt.% brine. It was flooded with the brine
at 35 psig and the absolute permeability was calculated from the
flow rate and pressure drop through sand pack using the Darcy’s
law equation. The sand pack was then flooded with the crude oil
Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
[m5G;October 14, 2017;19:19]
at 240 psig to irreducible water saturation. The initial water sat-
uration was determined on the basis of mass balance. The crude
oil used in the flooding experiments was collected from Oil India
Limited, Assam (India). The oil has a total acid number of 0.840 mg
KOH/g, gravity of 18.90°API and viscosity of 4.6 cP at 27 °C.
Darcy’s law was used to calculate the effective permeability to
oil (ko ) and effective permeability to water (kw ) at irreducible wa-
ter saturation (Swi ) and residual oil saturation (Sor ), respectively.
For a horizontal linear system, flow rate is related with permeabil-
ity as shown in Eq. (2)
kA dp
q= (2)
μ dx
where, q is the volumetric flow rate (cm3 /s), A is the total cross-
sectional area of the sandpack system (cm2 ), μ is the fluid viscosity
(cp), ddxp is the pressure gradient (atm/cm) and k is the permeability
in Darcy.
Water-flooding was initially conducted by subjecting the core-
holder placed horizontally to a constant injection pressure at
35 psig. After water flooding, when water-cut reached above 95%,
around 0.5 pore volume (PV) of surfactant slug was injected. This
was followed by chase water flooding (2.0 wt.% brine solution). The
flooding tests were repeated for all surfactant systems with varying
concentrations.
3. Results and discussion
3.1. Characterization of synthesized anionic surfactant
3.1.1. FTIR study of palm oil ethyl ester
The FTIR spectrum of synthesized palm oil ethyl ester derived
from palm oil is shown in Fig. 3. The FTIR spectrum of palm oil
ethyl ester shows an absorption band at 3471 cm−1 , arising due
to the stretching vibration of –OH bond. Peak at 3008 cm−1 cor-
responds to cisolefinic=C–H double bond. The symmetrical and
asymmetrical stretching vibrations of methylene group (–CH2 ) is
indicated by peaks at 2854 cm−1 and 2924 cm−1 . A strong peak
at 1746 cm−1 is attributed to C=O bond from ester as the main
functional group. The presence of a peak at 1464 cm−1 shows the
bending vibration of aliphatic groups –CH2 and –CH3 . The asym-
metrical axial stretching of the C–O ester group is identified by the
absorption peaks at 1237 cm−1 , 1163 cm−1 and 1116 cm−1 . The
JID: JTICE
ARTICLE IN PRESS [m5G;October 14, 2017;19:19]

N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13 5

Fig. 3. FTIR spectrum of Palm oil ethyl ester.

Fig. 4. FTIR spectrum of α -SEE.

peak near 722 cm−1 is due to the out-of-plane vibration of cis-
di-substituted olefins. FTIR spectrum of the synthesized surfactant
proved that palm oil is an ethyl ester of saturated and unsaturated
fatty acids.
3.1.2. FTIR study of α -SEE
Fig. 4 shows the FTIR spectrum of synthesized surfactant de-
rived from the palm oil. The spectra which appear in palm oil ethyl
ester are also present in synthesized surfactant. The absorbance for
different functional groups and bonds are shown in Fig. 4. Addi-
tional peaks at 1116 cm−1 and at 850 cm−1 , 617 cm−1 indicate the
stretching vibration of sulfonate groups (S=O) and (S–O) respec-
tively. Thus, the FTIR data confirms that the sulfonation of palm
oil ethyl ester produced the corresponding ethyl ester sulfonate.
The various peaks obtained in the FTIR spectra are discussed in
Table 2.
3.1.3. GC analysis of α -SEE
Fig. 5 shows the gas chromatogram of the surfactant synthe-
sized from palm oil. The purity of the final product is obtained
at ≥76%. The surfactant synthesized from palm oil is a mixture of
various fatty acid ethyl esters, which is confirmed by GC analy-
sis. A strong peak at retention time (RT) 17.22 with 43.09% peak
area shows that palmitic acid ethyl ester (C16:0 ) is constituted in
the synthesized product. The presence of oleic acid ethyl ester
(C18:1 ) is attributed to a peak at RT 19.43 and peak area percent-
age of 21.65%. A peak at RT 19.65 with 11.80% area in the GC chro-
matogram corresponds to stearic acid ethyl ester (C18:0 ).
3.1.4. FESEM analysis of α -SEE
FESEM analysis of α -SEE was performed to study the surface
morphology. Fig. 6(a) at 10 KX zoom shows that the surfactant
molecules appear to be in cluster form and are compact in nature.

Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
JID: JTICE
ARTICLE IN PRESS [m5G;October 14, 2017;19:19]

6 N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13

Table 2
Characteristic adsorption bands corresponding to different functional groups in palm-oil based surfactant.

Characteristic adsorption bands (cm−1 ) Description of functional group

310 0–370 0 Stretching vibration of O–H bonds

280 0–30 0 0 Stretching vibration of alkyl C–H bonds (asymmetric CH3 and CH2 stretching and symmetric CH2 )
1735–1750 Stretching vibration of ester groups C = O bonds
1620–1680 Stretching vibration of C = C bonds of alkene
1350–1480 Bending vibration of alkyl C–H bonds
1120–1160 Stretching vibration of the O = S = O bonds of sulfonate
850 & 617 Stretching vibration of S-O bonds
10 0 0–130 0 Stretching of C–O of ester group
1350–1480 CH3 asymmetric bending

Fig. 5. Gas chromatogram showing the retention time for different components of the α -SEE.

Fig. 6. FESEM image of α -SEE at different magnification: (a) 10 KX (b) 100 KX.

Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
JID: JTICE
ARTICLE IN PRESS [m5G;October 14, 2017;19:19]

N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13 7

Fig. 7. EDX analysis of the α -SEE.

Image shown in Fig. 6(b) at 100 KX zoom illustrates that particles

are rod-like and irregular in shape, and are well dispersed within
the area under analysis.

3.1.4. EDX spectrum of α -SEE

In EDX analysis of synthesized surfactant, five elements are ob-
served viz. carbon (C), oxygen (O), sodium (Na), sulfur (S) and gold
(Au) as shown in Fig. 7. The gold (Au) peak characterized in the
spectra was due to the presence of coating materials used along
with the surfactant during the analysis. All the remaining elements
present correspond to different components of the α -SEE. EDX data
clearly shows the presence of sulfur as chlorosulfonic acid was
used in the sulfonation reaction. The presence of sodium shows
that the anionic surfactant exists in the form of sodium salt. No
extra peak of any other element is depicted in the EDX spectra,
which indicates that the α -SEE surfactant is pure, without any
other elemental impurities.

Fig. 8. Thermal stability curve for α -SEE surfactant.

3.1.5. Thermal gravimetric analysis of α -SEE
The thermal stability of α -SEE was studied by thermo-
gravimetric analysis (TGA). The conventional reservoir temperature
lies in the range between 80 °C 120 °C [24]. Hence, it becomes
important to investigate the thermal degradation characteristics
of the surfactant for effective application in EOR processes. The
weight loss percentage is depicted with increase in temperature
in Fig. 8. TGA plot shows that the initial thermal loss occurs from
96 °C to 150 °C, wherein about 20% of loss in weight is observed.
No further loss in weight was observed above this temperature,
which shows that the α -SEE surfactant is thermally stable under
reservoir conditions which are pre-requisite for its application in
field of enhanced oil recovery. The presence of both saturated and
unsaturated fatty acids in palm oil supports the good thermal sta-
bility of α -SEE as these fatty acids require high temperature for
its degradation. The anti-oxidants present in palm oil aid in good
thermal stability.

Fig. 9. Variation of surface tension with concentration of synthesized surfactant at

3.2. Interfacial properties of α -SEE surfactant 27 °C.

3.2.1. Surface tension of α -SEE solutions

The surface tension versus concentration curve of α -SEE solu-
tions with concentration ranging from 0 ppm to 16,0 0 0 ppm is de-
picted in Fig. 9. The CMC of this surfactant was obtained as the
interception between the decreasing slope and horizontal constant
line of the surface tension curve plotted against concentration.
With the increase in concentration of synthesized surfactant so-
lution the surface tension values lowers as there is increase in ad-
sorption of surfactant molecules at the interface of air and water
[25] and this trend was observed until the concentration reached
CMC value of 80 0 0 ppm with surface tension of 32.5 mN/m. After

Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
JID: JTICE
ARTICLE IN PRESS
8 N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13
Fig. 10. Effect of time elapse on interfacial tension of α -SEE at different concentra-
tions at 27 °C.
the CMC, the surface tension curve attains a constant value as the
surface gets saturated with the surfactant molecules.
3.2.2. Salt tolerance analysis of α -SEE solutions
Generally salt tolerance of surfactants vary between
5 × 104 mg/L (5 wt.%) to 8 × 104 mg/L (8 wt.%) [26,27]. The salt
tolerance level of the surfactant solution is found to fall in this
range. Salt tolerance studies revealed that no surfactant precip-
itation occurred in the range between 1% NaCl and 7% NaCl for
α -SEE surfactant solutions at CMC (80 0 0 ppm). As the salt content
was increased to 8% NaCl, surfactant begins to precipitate in
solution. The surfactant is resistant to salt effects up to 7% NaCl
(7 × 104 mg/L) concentration. Therefore, the synthesized surfactant
shows good tolerance to reservoir salinity and can be effectively
used in both low salinity and high salinity reservoirs for oil
recovery applications.
3.2.3. Interfacial tension (IFT) of crude oil and α -SEE
Studies on dynamic interfacial tension (DIFT) between crude oil
and α -SEE surfactant solutions at 27 °C are depicted in Fig. 10.
The interfacial tension initially decreases to a minimum value, due
to the existence of dynamic equilibrium between adsorption and
desorption of α -SEE molecules at oil–water interface. As aqueous
phase interacts with oil phase, surfactant molecules show diffu-
sion phenomenon from the bulk to the interface, and at interface
of oil and water phase adsorption occurs. At first, the adsorption
rate of molecules was higher than desorption rate which lead to
reduction in DIFT. Finally, when an equilibrium state was achieved
and adsorption and desorption forces were balanced, the DIFT ap-
proached toward a constant value [28].
Fig. 11 shows the variation of equilibrium IFT with surfactant
concentration at 27 °C. With increase in α -SEE (alpha-sulfonated
ethyl ester) concentration in aqueous solution, more surfactant
molecules are adsorbed at the interface and IFT is reduced [29].
When surfactant concentration reaches critical micelle concentra-
tion (CMC) value, the oil–aqueous interface is saturated with sur-
factant molecules and micelles begin to form in the aqueous bulk
phase. At 80 0 0 ppm (CMC), the value of IFT was found to be
1.17 × 10−2 mN/m. As the surfactant concentration is further in-
creased, the micelle formation takes place resulting in slight in-
crease in IFT. This is attributed to change in the distribution of sur-
factant molecules in the oil and water phase, caused as a result of
increase in surfactant concentration [30].
3.2.4. Effect of salt concentration on IFT
Addition of salt plays a synergistic effect on the interfacial ac-
tivity of surfactant molecules at oil–aqueous interface. The effect
Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
[m5G;October 14, 2017;19:19]
Fig. 11. Interfacial tension versus concentration of α -SEE at 27 °C.
Fig. 12. Effect of salinity on IFT at CMC (80 0 0 ppm) of α -SEE at 27 °C.
of salt concentration on IFT value of surfactant solutions at CMC
is depicted in Fig. 12. The IFT shows a bell shaped curve with an
optimal salinity of 2% NaCl content in surfactant solution at CMC.
Initially, it decreases to a minimum value of 8.30 × 10−3 mN/m
at 2% salt content followed by an increase in the IFT value. Ini-
tially for palm oil-based anionic surfactant, the oil–aqueous inter-
face is negatively charged. On addition of NaCl salt, some Na+ ions
are attracted toward the adsorption layer as counterions, whereas
other cations form the electrical double layer [31]. With further in-
crease in salt concentration, more counterions are attracted toward
the interface, reducing the effective charge in the interface layer
[32,33]. This reduces the electrostatic repulsive forces between an-
ions carried by polar head group of α -SEE molecule, leading to
thinning of the interface layer. As a result, surfactant molecules
are more closely packed at the oil–aqueous interface and IFT is
drastically reduced [30,34]. After salt concentration in solution ex-
ceeds optimal salinity value, the ionic interactions between the hy-
drophilic group (negatively charged group of surfactant) and the
cationic part of salt (Na+ ) are subsequently decreased in surfactant
solution [35].
3.2.5. Effect of pH on IFT
Alkalis play a synergistic effect on the oil–aqueous interfacial
tension. Addition of alkali improves pH of the solution and makes
the solution more alkaline in nature. On alkali addition, the re-
activity with acidic component of crude oil is increased due to
the formation of in-situ surfactants by the deprotonation of acids
present in crude oil [36–38]. Fig. 13 shows the influence of pH due
to addition of mono-ethanolamine (MEA) on IFT between crude
oil and surfactant solution at CMC. IFT was found to decrease
with increase in pH value. Initially, this decrease was sharp at
JID: JTICE
ARTICLE IN PRESS [m5G;October 14, 2017;19:19]

N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13 9

Fig. 13. Effect of pH on IFT at CMC (80 0 0 ppm) of α -SEE at 27 °C.

Fig. 14. FTIR spectrum of dry quartz rock and crude oil aged quartz rock.

low pH values. IFT decrease by alkali addition is likely a con-

sequence of the synergism among surfactant molecules, ionized
acid and unionized acid to form a mixed adsorbed interfacial layer
[28,39]. Consequently, adsorption of surfactant molecules at oil–
aqueous interface is increased, resulting decrease of IFT. However,
IFT trend showed gradual and slower reduction with increase in
organic alkali concentrations (pH value). Minimum IFT value of
6.81 × 10−3 mN/m was achieved at solutions with 12 pH. Reduction
in IFT with pH may be attributed to the increased ionic strength,
which prevents the surfactant from adsorbing onto the surface of
rocks. Furthermore, MEA causes lesser reservoir damage due to its
organic nature and low alkali consumption in the reservoir [40,41].

3.3. Wettability alteration studies

3.3.1. Characterization of quartz and carbonate rock surfaces

A water-wet rock surface possesses greater oil recovery that can
be achieved by water flooding. When the calculated amount of sur-
factant solution is injected to the oil-wet or intermediate wet rock
the trapped oil is recovered efficiently due to the change in wetta-
bility of rock from oil-wet to water-wet. This change in wettability
is governed by three factors: the electrostatic force between the
ions, the forces of attraction between surfactant and polar compo-
nents of crude oil, and surface characteristics of the rock.
The FTIR analysis of quartz rock, dry and aged with crude oil
is depicted in Fig. 14. The spectrum of dry quartz show bands
at 458 cm−1 and 689 cm−1 corresponding to asymmetric and
symmetric bending vibrations of Si–O bonds whereas peaks at
782 cm−1 and 1081 cm−1 , corresponds to stretching vibration
for Si–O bond. The Si–O bond between the quartz rock surfaces
clarifies the presence of silica as its main component, whereas
the aged quartz rock shows bending vibrations of C–H of sub-
stituted benzene at 1076 cm−1 and C=C stretching vibration at
1630 cm−1 respectively. The absorption band at 2850 cm−1 and
2922 cm−1 depicts C–H symmetric vibration of the saturated hydro-
carbons and O–H band due to stretching vibration at 3435 cm−1 .
C=O stretching peaks appeared between 1627 cm−1 to 1870 cm−1
which confirms the presence of carbonyl components like acids,
aliphatic esters and aldehydes in the crude oil. Many new peaks
are observed which corresponds to the components of crude oil,
thereby confirming the ageing of quartz with crude oil.
Characterization of the functional groups present in, dry and
oil-wet carbonate rock were done using the FTIR technique, and
the results are shown in Fig. 15. The FTIR spectrum of dry car-
bonate rock surface shows absorption peaks at 868 cm−1 and
Fig. 15. FTIR spectrum of dry and aged carbonate rock with crude oil.
1794 cm−1 corresponding to stretching vibration for Ca–CO3 bonds
for calcite. Carbonate rock aged in the crude oil show absorption
bands at about 3436 cm−1 , depicting bending vibration of O–H
bonds. A new peak at 2947 cm−1 corresponds to alkyl C–H bond,
thereby confirming that the rock was aged with crude oil.
3.3.2. Effect of surfactant concentration on contact angle
The contact angle values of surfactant solution at different con-
centrations with time were measured to study the wettability al-
teration of oil-wet rock surfaces. The sessile drop method was used
to calculate the contact angle of oil wetted rock surfaces at differ-
ent surfactant concentrations. Initially the test was conducted with
distilled water and the contact angle calculated were found to be
greater than 90° at the start, indicating that the rock surface under
study was oil-wet. In the presence of surfactant, the contact angle
gradually decreased with elapse of time and reached a constant
value after 10 0 0 s, showing that the rock surface had changed its
wettability to water-wet. This decrease in contact angle value is
dependent on the type of rock surface, type of surfactant used
and the acid components of crude oil adsorbed onto the surface
of rock used [42]. The plot of contact angle versus time for carbon-
ate and quartz rock surfaces at different concentrations is shown in
Figs. 16 and 17 respectively.

Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
JID: JTICE
ARTICLE IN PRESS
10 N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13
Fig. 16. The contact angle of oil wet carbonate surface through surfactant dosing at
different concentration at 27 °C.
Fig. 17. The contact angle of oil wet quartz surface through surfactant dosing at
different concentrations at 27 °C.
Surfactant concentration plays a pivotal role in controlling the
dynamic wetting characteristics of both quartz and carbonate
rocks. The interaction between SO4 2− ions in the palm oil-based
surfactant and organic compounds on the rock surface displaces
the adsorbed fatty acids (in crude oil) adsorbed on rock surface
and, therefore, reduces oil-wetness [43,44]. This improves the oil-
displacing ability of the surfactant at the interface between oil-wet
rock and aqueous solution of surfactant [45]. The lowest drop in
contact angle is observed at CMC value (80 0 0 ppm) of the synthe-
sized surfactant. For carbonate rock surface, surfactant solution at
CMC showed contact angle decrease from 82.5° to 20.7° in 10 0 0 s.
Contact angle is found to decrease from 80.3° to 17.3° in 10 0 0 s
for quartz surface at CMC (80 0 0 ppm). This shows that ability to
alter nature of the rock surface from oil-wet to water-wet surface
is most favorable at CMC. At surfactant concentrations above CMC,
rate of decrease of contact angle with time is reduced, showing
that adhesion tension between rock and surfactant solution does
not increase with concentrations beyond CMC [46]. Variation in
contact angle shows that the alteration of wettability of rock is due
to the effect of two mechanisms predicted: first is ion-pair attrac-
tion between the anionic polar head groups of the surfactant units
and cationic charged components present in the crude oil adsorbed
on the rock surface [47,48]. Another possible reason for this varia-
tion can be the adsorption of negatively charged group of anionic
surfactant onto the positively charged surface of rock [49]. Conse-
Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
[m5G;October 14, 2017;19:19]
Fig. 18. Effect of salinity on contact angle at CMC (80 0 0 ppm) of α -SEE solution at
27 °C on Quartz surface and Carbonate rock surface.
quently, α -SEE surfactant synthesized from palm oil proves to be
highly efficient in altering the wettability of rock from oil-wet to
water-wet,which ultimately aids in enhancing the oil recovery.
3.3.3. Effect of salinity on contact angle
Salinity plays a crucial role in wettability alteration behavior of
surfactant solutions. Hence, there is a need to study the effect of
salt on alteration of wettability of oil wet rock surfaces at opti-
mal surfactant concentration of 80 0 0 ppm at 27 °C. Fig. 18 shows
the influence of salinity on contact angle behavior of quartz and
carbonate rocks respectively for 600 s. Addition of salt (NaCl) im-
proves the wettability behavior of oil-wet rock due to increased
rate of accumulation of surface active components at oil–aqueous
interface. The contact angle value decreases with the increase in
salt percentage in surfactant solution at CMC. This may be due
to the salting-out of surfactant molecules in aqueous phase in the
presence of NaCl [50]. As salt concentration in CMC surfactant so-
lution increases, some water molecules are attracted by salt ions.
This reduces the availability of water molecules to interact with
surfactant molecules in bulk solution. As a result, faster diffusion
rate of surfactant molecules from bulk to interface is achieved and
additional surfactant molecules precipitate to the rock–aqueous in-
terface to form stronger hydrophobic surfactant-surfactant inter-
actions [13,51]. This phenomenon is observed till optimal salin-
ity value is reached. At optimal salinity (2% NaCl), wetting char-
acteristics are more favorable than other solutions for application
in EOR. Contact angle values are found to decrease from oil-wet
conditions to 7.7° for quartz and 12.9° for carbonate rock surfaces
respectively in 600 s. The decrease in value of contact angle at op-
timal salinity is due to the reduced electrostatic repulsion force as
more sodium ions are bound to oil wet surface which results in al-
teration of wettability [52]. Beyond optimal salinity, the repulsive
electrostatic and hydration forces at the rock–solution interface in-
crease in order to avoid droplet spreading at the surface [53]. This
reduces the adsorption of the surfactant onto the rock surface and
thus, increases the value of contact angle with increase in salinity
above the optimal salinity [54]. It is, therefore, concluded that salt–
surfactant mixtures show better wettability characteristics as com-
pared to surfactant solutions on both quartz and carbonate rock
surfaces [55].
JID: JTICE
ARTICLE IN PRESS [m5G;October 14, 2017;19:19]

N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13 11

Fig. 19. Flooding performance of α -SEE slugs in sandpack system at different surfactant concentrations: (a) 80 0 0 ppm, (b) 10,0 0 0 ppm, (c) 12,0 0 0 ppm, and (d) additional oil
recoveries.

Table 3
Flooding results of the different systems.

Sandpack Porosity Permeability, k (Darcy) Design of chemical Oil Recovery Additional % Saturation
sample No. (%) slug for flooding (%OOIP) at 95% recovery (%
kw (Sw = 1) ko (Swi ) water cut OOIP) Swi Soi Sor

I 31.24 4.47 0.58 0.5 PV 80 0 0 ppm 51.10 25.80 21.14 78.86 19.20
SMES + Chase water
II 31.64 4.75 0.65 0.5 PV 10,0 0 0 ppm 51.70 26.10 20.35 79.65 18.10
SMES + Chase water
III 31.97 5.10 0.70 0.5 PV 12,0 0 0 ppm 51.50 26.30 20.10 79.90 17.00
SMES + Chase water

3.4. Oil recovery by flooding of synthesized surfactant solutions
While planning for surfactant flooding in chemical enhanced
oil recovery, it is important to design the surfactant slug with
optimum concentration of surfactant. Optimum surfactant concen-
tration basically depends on the CMC of surfactant, adsorption of
surfactant onto the reservoir rock, salt tolerance and interfacial
behavior at oil–aqueous interface. In this study, flooding tests were
conducted with the injection of α -SEE surfactant slugs at three
different concentrations. During surfactant flooding, a significant
amount of surfactant is adsorbed on the rock surface. Hence,
flooding studies are carried out with surfactant slugs at concen-
trations higher than CMC value (80 0 0 ppm) to account for these
adsorption losses. This ensures that under reservoir conditions, at
least CMC of surfactant is maintained for efficient recovery of oil.
Sandpack saturated with crude oil (obtained from Oil India,
Assam) was initially flooded with brine solution (2% NaCl). Water
breakthrough was found to occur after injection of small pore vol-
ume of displacing fluid during flooding test due to lower viscosity
of water as compared to that of crude oil. Almost 52% of original
oil in place (OOIP) is recovered after conventional water flooding
due to high porosity of the sandpack system. When water-cut
reached up to ∼95%, injection of surfactant slug improved the
oil recovery rate with drastic reduction in water-cut percentages.
However, with further increase in pore volume of slug injected,
the oil recovery increased with simultaneous increase in water-cut.
The flooding performance of different surfactant slugs (80 0 0 ppm,
10,0 0 0 ppm, 12,0 0 0 ppm) injected into the sandpack systems are
depicted in Fig. 19(a), (b) and (c) respectively. After injection of
surfactant slug, the oil droplets trapped in pores are mobilized
due to reduction of interfacial tension between oil and displac-
ing fluid [56,57]. With increase in surfactant concentration, oil
saturation increases due to increase in the coalescence of mobi-
lized oil droplets to form oil bank [58–60]. This allows better oil

Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
JID: JTICE
ARTICLE IN PRESS
12 N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13
displacement by injected fluid with increase in surfactant con-
centration [60,61]. Behind the oil bank, the surfactant prevents
backflow and subsequent retrapment of mobilized oil in the pores.
After injection of surfactant slug, the chase water flooding is
continued till no further recovery of oil. A comparative study of
additional oil recoveries after water flooding by surfactant solution
at different concentrations is illustrated in Fig.19(d). It has been
found that additional recoveries of 24.70%, 25.80% and 27.60% of
OOIP after water injection were observed for three different con-
centrations of surfactant. Surfactant slugs with higher concentra-
tion always contain sufficient concentration to achieve low IFT and
low contact angle even after adsorption. Thus additional recovery
increases with increase in surfactant concentration. A comparative
picture of oil recovery at different surfactant concentrations along
with different petro-physical properties are shown in Table 3.
4. Conclusions
The effectiveness of an anionic surfactant synthesized from
a natural vegetable resource, palm oil has been investigated
for application in enhanced oil recovery. The surfactant, alpha-
sodium ethyl ester (α -SEE) has been suitably characterized by FTIR,
GC, EDX and FE-SEM techniques for the determination of func-
tional groups, presence of various esters, elemental composition
and molecular surface morphology, respectively. Thermogravimet-
ric analysis shows good thermal stability of α -SEE surfactant up
to reservoir temperature. Critical micelle concentration (CMC) of
the synthesized surfactant is found to be 80 0 0 ppm at 27 °C. An
ultralow IFT of 1.17 × 10−2 mN/m is observed at the crude oil–
aqueous solution interface at CMC. The value of IFT is further re-
duced to 8.30 × 10−3 mN/m under optimal salinity conditions (2%
NaCl) at CMC. By addition of organic alkali (MEA) IFT reduced to
very low values, and a minimum value of 6.81 × 10−3 mN/m was
obtained at pH 12 for alkali-surfactant system at CMC. The surfac-
tant shows good wetting characteristics by altering the nature of
the both quartz and carbonate rock surfaces from oil-wet to water-
wet. Contact angle values are found to initially decrease with sur-
factant concentration up to CMC, after which it starts increasing.
Effect of addition of salt shows much lower contact angle reduc-
tion as compared to that of pure surfactant solutions. Flooding ex-
periments show additional recoveries of 25.80%, 26.10% and 26.30%
OOIP by the injection of different surfactant slugs with 80 0 0 ppm,
10,0 0 0 ppm and 12,0 0 0 ppm concentrations respectively after con-
ventional water flooding for sandpack systems with 2% brine salin-
ity.
Acknowledgments
The authors gratefully acknowledge the financial assistance pro-
vided by Oil India Limited [Contract No. 62O6917], Duliajan, Assam,
India to the Department of Petroleum Engineering, Indian Institute
of Technology (ISM), Dhanbad, India. Authors would also like to
thank Central Research Facility, IIT (ISM), Dhanbad, India for tech-
nical assistance and support.
References
[1] Green DW, Willhite GP. Enhanced oil recovery. SPE textbook series. 1st ed.
Texas: Richardson; 1998.
[2] Majidaie S, Muhammad M, Tan IM, Demiral B. Green surfactant for enhanced
oil recovery. In: 2011 Natl. Postgrad. Conf. - Energy Sustain. Explor. Innov.
Minds; 2011. p. 1–5.
[3] Babu K, Pal N, Saxena VK, Mandal A. Synthesis and characterization of a new
polymeric surfactant for chemical enhanced oil recovery. Korean J Chem Eng
2016;33(2):711–19.
[4] Ahmadi AM, Shadizadeh RS. Experimental investigation of adsorption of a new
nonionic surfactant on carbonate minerals. Fuel 2013;104:462–7.
Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
[m5G;October 14, 2017;19:19]
[5] Negm NA, El-Tabl AS, Aiad IA, Zakareya K, Moustafa AH. Synthesis, char-
acterization, biodegradation and evaluation of the surface active proper-
ties of nonionic surfactants derived from Jatropha oil. J Surfactants Deterg
2013;16(6):857–63.
[6] Ghosh M, Bhattacharyya DK. Enzymic preparation of polyethylene glycol esters
of castor oil fatty acids and their surface-active properties. J Surfactants Deterg
1998;1(4):503–5.
[7] Johansson I, Svensson M. Surfactants based on fatty acids and other natural
hydrophobes. Curr Opin Colloid Interface Sci 2001;6(2):178–88.
[8] Zhang Q, Zhang S, Dai L, Chen X. Novel zwitterionic poly(arylene ether sul-
fone)s as antifouling membrane material. J Membr Sci 2010;349(1–2):217–24.
[9] Flaaten A, Nguyen QP, Pope GA, Zhang JA. Systematic laboratory approach to
low-cost, high-performance chemical flooding. Society of Petroleum Engineers;
2008.
[10] Babu K, Maurya NK, Mandal A, Saxena VK. Synthesis and characterization of
sodium methyl ester sulfonate for chemically-enhanced oil recovery. Braz J
Chem Eng 2015;32(3):795–803.
[11] Matassoli ALF, Corrêa INS, Portilho MF, Veloso CF, Langone MAP. Enzymatic
synthesis of biodiesel via alcoholysis of palm oil. Appl Biochem Biotechnol
2009;155:44–52.
[12] Kenneth J, Wasan DT, Mohan V. Improved oil recovery by surfactant and poly-
mer flooding; 1977.
[13] Kumar S, Mandal A. Studies on interfacial behavior and wettability change
phenomena by ionic and nonionic surfactants in presence of alkalis and salt
for enhanced oil recovery. Appl Surf Sci 2016;372:42–51.
[14] Babu K, Pal N, Bera A, Saxena VK, Mandal A. Studies on interfacial tension
and contact angle of synthesized surfactant and polymeric from castor oil for
enhanced oil recovery. Appl Surf Sci 2015;353:1126–36.
[15] Shaw JF, Lo S. Production of propylene glycol fatty acid monoesters by lipase–
catalyzed reactions in organic solvents. J Am Oil Chem Soc 1994;71(7):715–19.
[16] Mattson FH, Volpenhein RA. Synthesis and properties of glycerides. J Lipid Res
1962;3(3):281–96.
[17] Hayes DG, Gulari E. Formation of polyol-fatty acid esters by lipases in reverse
micellar media. Biotechnol Bioeng 1992;40(1):110–18.
[18] Hayes DG, Kleiman R. Lipase-catalyzed synthesis and properties of estolides
and their esters. J Am Oil Chem Soc 1995;72(11):1309–16.
[19] Hayes DG, Kleiman R. Lipase-catalyzed synthesis of lesquerolic acid
wax and diol esters and their properties. JAOCS, J Am Oil Chem Soc
1996;73(11):1385–92.
[20] Hayes DG. The catalytic activity of lipases toward hydroxy fatty acids—a re-
view. JAOCS, J Am Oil Chem Soc 1996;73(5):543–9.
[21] Ziemann A, Wagner F. Enzymatic monoacylation of trihydroxy compounds.
Biotechnol. Lett. 1992;14(9):773–8.
[22] Lang S, Multzsch R, Passeri A, Schmeichel A. Unusual wax esters and gly-
colipids : biocatalytical formation and physico-chemical characterization. Acta
Biotechnol. 1991;11(4):379–86.
[23] Multzsch R, Lokotsch W, Steffen B, Lang S, Metzger JO, Schafer HJ, et al. Enzy-
matic production & physicochemical characterization of uncommon wax esters
and monoglycerides.pdf. J Am Oil Chem Soc 1994;71(7):721–5.
[24] Kumar S, Saxena N, Mandal A. Synthesis and evaluation of physicochemical
properties of anionic polymeric surfactant derived from Jatropha oil for appli-
cation in enhanced oil recovery. J Ind Eng Chem 2016;43:106–16.
[25] Han F, Deng YY, Wang PL, Song J, Zhou YW, Xu BC. Synthesis and characteri-
zation of glucosamide surfactant. J Surfactants Deterg 2013;16(2):155–9.
[26] Jixiang G, Xiao S, Zuguo Y, Jingjing C, Lei W. Synthesis of temperature-resistant
and salt- tolerant surfactant SDB-7 and its performance. Pet Sci 2014:584–9.
[27] Zhao L, Li A, Chen K, Tang J, Fu S. Development and evaluation of foaming
agents for high salinity tolerance. J Pet Sci Eng 2012;81:18–23.
[28] Zhao Z, Li Z, Qiao W, Cheng L. Dynamic interfacial behavior between crude
oil and octylmethylnaphthalene sulfonate surfactant flooding systems. Colloids
Surf A Physicochem Eng Asp 2005;259(1–3):71–80.
[29] Elraies KA, Tan IM, Awang M, Saaid AI. The synthesis and performance of
sodium methyl ester sulphonate for enhanced oil recovery. Petrol Sci Technol
2010;28:1799–806.
[30] Yuan CD, Pu WF, Wang XC, Sun L, Zhang YC, Cheng S. Effects of interfacial
tension, emulsification, and surfactant concentration on oil recovery in surfac-
tant flooding process for high temperature and high salinity reservoirs. Energy
Fuels 2015;29:6165–76.
[31] Bera A, Ojha K, Mandal A, Kumar T. Interfacial tension and phase be-
havior of surfactant-brine-oil system. Colloids Surf A Physicochem Eng Asp
2011;383(1–3):114–19.
[32] Zhang L, Luo L, Zhao S, Xu Z, An J, Yu J. Effect of different acidic fractions
in crude oil on dynamic interfacial tensions in surfactant/alkali/model oil sys-
tems. J Pet Sci Eng 2004;41:189–98.
[33] Zhao Z, Bi C, Li Z, Qiao W, Cheng L. Interfacial tension between crude oil and
decylmethylnaphthalene sulfonate surfactant alkali-free flooding systems. Col-
loids Surf A 2006;276:186–91.
[34] Li Y, He X, Cao X, Zhao G, Tian X, Cui X. Molecular behavior and synergistic ef-
fects between sodium dodecylbenzene sulfonate and Triton X-100 at oil/water
interface. J Colloid Interface Sci 2007;307:215–20.
[35] Moeini F, Hemmati-Sarapardeh A, Ghazanfari MH, Masihi M, Ayatollahi S.
Toward mechanistic understanding of heavy crude oil/brine interfacial ten-
sion: the roles of salinity, temperature and pressure. Fluid Phase Equilib
2014;375:191–200.
[36] Peru DA, Lorenz PB. Surfactant-enhanced low-pH alkaline flooding. SPE Reserv
Eng 1990;5(3):327–32.
JID: JTICE
ARTICLE IN PRESS
N. Saxena et al. / Journal of the Taiwan Institute of Chemical Engineers 000 (2017) 1–13
[37] Qiao W, Li J, Zhu Y, Cai H. Interfacial tension behavior of double long-chain
1,3,5-triazine surfactants for enhanced oil recovery. Fuel 2012;96:220–5.
[38] Chu Y, Gong Y, Tan X, Zhang L, Zhao S, An J, et al. Studies of synergism
for lowering dynamic interfacial tension in sodium α -(n-alkyl) naphthalene
sulphonate/acidic oil systems. J Colloid Interface Sci 2004;276:182–7.
[39] Trabelsi S, Argillier JF, Dalmazzone C, Hutin A, Bazin B, Langevin D. Effect
of added surfactants in an enhanced alkaline/heavy oil system. Energy Fuels
2011;25:1681–5.
[40] Hou J, Ziu Z, Yue X, Xia H. Study of the effect of ASP solution viscoelasticity
on displacement efficiency. In: Proceedings of SPE Annual Technical Conference
and Exhibition. Society of Petroleum Engineers; 2001.
[41] Xie D, Hou J, Zhao F, Doda A, Trivedi J. The comparison study of IFT and con-
sumption behaviors between organic alkali and inorganic alkali. J Pet Sci Eng
2016;147:528–35.
[42] Bera A, Kissmathulla S, Ojha K, Kumar T, Mandal A. Mechanistic study of wet-
tability alteration of quartz surface induced by nonionic surfactants and inter-
action between crude oil and quartz in the presence of sodium chloride salt.
Energy Fuels 2012;26(6):3634–43.
[43] Karoussi O, Hamouda AAJ. Macroscopic and nanoscale study of wettability al-
teration of oil- wet calcite surface in presence of magnesium and Sulfate ions.
Colloid Interface Sci 2008;317:26–34.
[44] Karimi M, Al-Maamar SR, Ayatollahi S, Nasir M. Impact of sulfate ions on wet-
tability alteration of oil-wet calcite in the absence and presence of cationic
surfactant. Energy Fuels 2016;30:819–29.
[45] Mohammed M, Babadagli T. Wettability alteration: a comprehensive review
of materials/methods and testing the selected ones on heavy-oil containing
oil-wet systems. Adv Colloid Interface Sci 2015;220:54–77.
[46] Eckmann DM, Cavanagh DP, Branger AB. Wetting characteristics of aqueous
surfactant-laden drops. Colloid Interface Sci 2001;242:386–94.
[47] Salehi M, Johnson SJ, Liang JT. Mechanistic study of wettability alteration us-
ing surfactants with applications in naturally fractured reservoirs. Langmuir
2008;24(24):14099–107.
[48] Standnes DC, Austad T. Wettability alteration in chalk 2. Mechanism for wet-
tability alteration from oil-wet to water-wet using surfactants. J Pet Sci Eng
20 0 0;28(3):123–43.
Please cite this article as: N. Saxena et al., Characterizations of surfactant synthesized from palm oil and its application in enhanced oil
recovery, Journal of the Taiwan Institute of Chemical Engineers (2017), https://doi.org/10.1016/j.jtice.2017.09.014
[m5G;October 14, 2017;19:19]
13
[49] Hou BF, Wang YF, Huang Y. Mechanistic study of wettability alteration
of oil-wet sandstone surface using different surfactants. Appl Surf Sci
2015;330:56–64.
[50] Ren ZH. Mechanism of the salt effect on micellization of an aminosulfonate
amphoteric surfactant. J Ind Eng Chem 2015;54:9683–8.
[51] Prosser AJ, Franses EI. Adsorption and surface tension of ionic surfactants at
the airwater interface: review and evaluation of equilibrium models. Colloids
Surf A 2001;178:1–40.
[52] Golabi E, Azad FS, Ayatollahi SS, Hosseini SN, Akhlaghi N. Experimental study
of wettability alteration of limestone rock from oil-wet to water-wet using var-
ious surfactants. In: SPE Heavy Oil Conf.; 2012. p. 1–16.
[53] Shedid SA, Ghannam MT. Factors affecting contact-angle measurement of
reservoir rocks. J Pet Sci Eng 2004;81:193–203.
[54] Gupta R, Mohanty KK. Wettability alteration of fractured carbonate reservoirs.
In: SPE Symp Improv Oil Recover; 2008. p. 19–23. No. April.
[55] Szymczyk K, Jańczuk B. Wettability of a polytetrafluoroethylene surface
by an aqueous solution of two nonionic surfactant mixtures. Langmuir
2007;23:8740–6.
[56] Sofla SJD, Sharifi M, Sarapardeh AH. Toward mechanistic understanding of nat-
ural surfactant flooding in enhanced oil recovery processes: the role of salinity,
surfactant concentration and rock type. J Mol Liq. 2016;222:632–9.
[57] Park S, Lee ES, Sulaiman WRW. Adsorption behaviors of surfactants for chem-
ical flooding in enhanced oil recovery. J Ind Eng Chem 2015;21:1239–45.
[58] Iglauera S, Wua Y, Shulera P, Tanga Y, Goddard III WA. New surfactant classes
for enhanced oil recovery and their tertiary oil recovery potential. J Pet Sci Eng
2010;71:23–9.
[59] Joonaki E, Gahrooei HRE, Ghanaatian S. Experimental study on adsorption and
wettability alteration aspects of a new chemical using for enhanced oil recov-
ery in carbonate oil reservoirs. J Unconv Oil Gas Resour 2016;15:11–21.
[60] Bera A, Mandal A, Guha BB. Synergistic effect of surfactant and salt mixture
on interfacial tension reduction between crude oil and water in enhanced oil
recovery. J Chem Eng Data 2014;59:89–96.
[61] Ahmadi MA, Shadizadeh SR. Implementation of a high-performance surfac-
tant for enhanced oil recovery from carbonate reservoirs. J Pet Sci Eng
2013;110:66–73.