Synthesis of two chiral surfactants by a simple method and the surface activity evaluation

Article abstract of DOI:10.1016/j.molliq.2020.113892

In order to expand the application range of surfactants, two chiral surfactants named CTACYT and CTATYS were synthesized by reacting cetyltrimethylammonium chloride (CTAC) with L-cysteine and L-tyrosine, respectively by a simple method. Studies show that the foaming ability, foam stability and emulsifying properties of both CTACYT and CTATYS are superior to CTAC. The corrosion inhibition efficiencies of CTACYT and CTATYS are 96.72% and 90.22%, respectively, which are higher than that of CTAC. The new chiral surfactants remain the chiral character, and the specific optical rotations of CTACYT and CTATYS were 8.1° and 11.6°, respectively. This work provides a new and easy way to the synthesis of chiral surfactants, which will benefit the related research in this field.

Full text of DOI:10.1016/j.molliq.2020.113892

Journal of Molecular Liquids 316 (2020) 113892
Contents lists available at ScienceDirect
Journal of Molecular Liquids
journal homepage: www.elsevier.com/locate/molliq
Synthesis of two chiral surfactants by a simple method and the surface
activity evaluation
a
a
Gang Chena,b, , Jiao Yan , Yun Bai , Sanbao Donga,b, Dengwei Liu c, Jie Zhanga,
⁎
Shidong Zhu a,b, Chengtun Qu a,b,
Shaanxi Province Key Laboratory of Environmental Pollution Control and Reservoir Protection Technology of Oilfields, Xi'an Shiyou University, Xi'an 710065, China
State Key Laboratory of Petroleum Pollution Control, CNPC Research Institute of Safety and Environmental Technology, Beijing 102206, China
Development Research Center, Ministry of Water Resources, Beijing 100038, China
⁎
a
b
c
a r t i c l e i n f o
a b s t r a c t
Article history:
In order to expand the application range of surfactants, two chiral surfactants named CTACYT and CTATYS were
synthesized by reacting cetyltrimethylammonium chloride (CTAC) with L-cysteine and L-tyrosine, respectively
by a simple method. Studies show that the foaming ability, foam stability and emulsifying properties of both
CTACYT and CTATYS are superior to CTAC. The corrosion inhibition efficiencies of CTACYT and CTATYS are
96.72% and 90.22%, respectively, which are higher than that of CTAC. The new chiral surfactants remain the chiral
character, and the specific optical rotations of CTACYT and CTATYS were 8.1° and 11.6°, respectively. This work
provides a new and easy way to the synthesis of chiral surfactants, which will benefit the related research in
this field.
Received 18 December 2019
Received in revised form 19 July 2020
Accepted 21 July 2020
Available online 24 July 2020
Keywords:
Chiral surfactants
Surface tension
Foam ability
© 2020 Elsevier B.V. All rights reserved.
Emulsification
Corrosion inhibition
Specific optical rotation
1. Introduction
rationally design functional cationic surfactants by incorporating func-
tional groups into conventional cationic surfactants [8–12]. Depending
Quaternary ammonium cationic surfactants are widely used in many
fields, such as textiles, cosmetics and petrochemical industries [1–3].
The prepared cationic surfactants display greater aqueous solution
properties as compared to other cationic surfactants, such as minimum
surface tension, lower critical micelle concentration (CMC), higher
foaming ability, better emulsifying performances, and higher corrosion
inhibition efficiency [4,5]. Experimental study found that the structure
of surfactant has a significant impact on its properties, such as washing,
wetting, dispersing, emulsifying, solubilizing, foaming and so on. It is
widely used in the fields of washing products, chemical industry, med-
icine, textile, remediation of petroleum oil contaminated soil [6] and so
on. With the continuous development of economy, the level of chemical
industry in China has been greatly improved, with the growth of our de-
mand and application of surfactants. In order to effectively promote the
application of surfactants in various fields, we need to strengthen the
chemical structure of surfactants [7]. In recent years, researchers have
expanded their range of applications by complexing cationic surfactants
with other types of surfactants. However, few studies have attempted to
on the functional group, functional cationic surfactants can react to vari-
ous environmental stimuli to achieve their desired effects and applications.
Due to scientific curiosity, our study uses cetyltrimethylammonium
chloride (CTAC) as a raw material to react with L-cysteine and L-
tyrosine, respectively to synthesize two kinds of chiral surfactants
(CTACYT, CTATYS) by simple method. Here, we studied the foaming
properties, the emulsifying properties and the corrosion inhibition
properties of two kinds of chiral surfactants.
2. Experimental
2.1. Materials
Cetyltrimethylammonium chloride (CTAC), L-cysteine and L-
Tyrosine were purchased from China National Pharmaceutical Group.
Other chemicals were purchased from Xi'an Chemical Reagent Factory,
and were used without further purification.
2.2. Synthesis of CTACYT and CTATYS
⁎
Corresponding authors at: State Key Laboratory of Petroleum Pollution Control, CNPC
Sodium hydroxide reacted completely with cetyltrimethylammonium
chloride (molar ratio of 1:1) at room temperature using methanol as a
Research Institute of Safety and Environmental Technology, Beijing 102206, China.
E-mail addresses: gangchen@xsyu.edu.cn (G. Chen), xianquct@xsyu.edu.cn (C. Qu).
https://doi.org/10.1016/j.molliq.2020.113892
0167-7322/© 2020 Elsevier B.V. All rights reserved.

2
G. Chen et al. / Journal of Molecular Liquids 316 (2020) 113892
solvent. Then, the supernatant reacted with L-cysteine and L-tyrosine, re-
spectively (molar ratio of 1:1), was heated to reflux for 2 h with stirring,
and the mixture was evaporated and dried. Finally, two new surfactants
(CTACYT, CTATYS) were obtained. The synthetic chemical equations for
CTACYT and CTATYS are shown in Fig. 1. The products were recrystallized
in ethanol to get the purified product for the following characterization
and evaluation. 1H NMR of CTACYT (D2O, 400 MHz), δ: 3.80 (1H, dd,
J = 7.2 Hz), 3.30 (9H, s), 3.23–3.24 (3H, m), 2.98 (1H, m), 2.55 (1H, b),
1.73 (2H, dd, J = 7.2 Hz), 1.65 (1H, b), 1.29–1.32 (26H, m), 0.96 (3H, t,
J = 7.2 Hz); 1H NMR of CTATYS (D2O, 400 MHz), δ: 6.95 (2H, d, J =
6.8 Hz), 6.68(2H, d, J = 6.8 Hz), 5.93 (1H, b), 3.87 (1H, dd, J = 7.2 Hz),
3.30 (9H, s), 3.23–3.24 (3H, m), 2.97 (1H, m), 2.72 (1H, b), 1.73 (2H, dd,
J = 7.2 Hz), 1.29–1.32 (26H, m), 0.96 (3H, t, J = 7.2 Hz).
tube was shaken evenly 200 times, which was immediately placed on
the test tube rack vertically and placed back in the 60 °C incubator.
Then, the timing started and the water separated in the test tube was re-
corded at volume intervals. The formula for calculating the water ex-
traction rate is:
VW
Ed
¼
ꢀ 100%
V
Where:
Ed-water extraction rate (%);
Vw-water output (ml);
V-the water phase volume when preparing emulsion (mL).
2.3. Surface tension measurement
2.6. Corrosion inhibition measurement
Hanging ring method is one of the frequently used methods for mea-
suring the surface tension of different surfactant solutions. At room tem-
perature, a Krüss-K6 tensiometer (Krüss K100, Germany) was used to
measure the surface tension by means of different surfactant solutions
prepared at concentrations ranging from 10 to 5000 mg/l [7]. The plat-
inum ring was often washed using distilled water to obtain a standard
surface tension value of the distilled water. All surface tension measure-
ments were repeated thrice to reduce the error [8].
A weight loss technique was used to evaluate the inhibiting effi-
ciency of the four surfactant solutions at a certain concentration in HCl
solution at 60 °C for 4 h [13]. The experiment was carried out with a
40 mm × l3 mm × 2 mm mild steel sample. The sample was polished
with 360#, 600#, 1200# sandpaper on a smooth plane before the exper-
iment, and then the polished sample was cleaned in distilled water and
later washed with absolute ethanol. Finally, it was washed with acetone.
They were dried by degreasing cold air, placed in a dryer, weighed with
an electronic balance 5 min prior to the experiment, and then the
length, width, thickness, diameter of the hole were measured with a
vernier caliper. These samples were immersed in 5% HCl solution, and
different surfactant solutions were added at some concentration at
60 °C for 4 h [14].
Electrochemical measurements were conducted in a conventional
three-electrode thermostated cell. The electrode was inserted into a Tef-
lon tube and isolated with polyester so that only its section (0.5 cm2)
was allowed to contact the aggressive solutions. A platinum disk as
counter electrode and standard calomel electrode (SCE) as the reference
electrode have been used in the electrochemical studies. The potentio-
dynamic curves were recorded using a CS350 system connected to a
personal computer. The working electrode was first immersed in the
test solution for 60 min to establish a steady state open circuit potential.
After measuring the open circuit, potential dynamic polarization curves
were obtained with a scan rate of 0.5 mV/s. Corrosion rates (corrosion
2.4. Foaming ability measurement
The foaming ability is usually measured by the Waring Blender
method. 100 ml solution was poured into a 500 ml container with a
high speed stirrer, and the time t1/2 (half-life) represents stabilization
[9]. Each experiment was repeated at least three times [10]. The micro-
structure of the foam was characterized under a microscope using a po-
larizing microscope (DM4500P LFD, Germany).
2.5. Emulsification
Three 20 ml stoppered graduated cylinders were taken, 2% different
surfactant solutions with 10 ml of dehydrated and degassed crude oil
were added in a volume ratio of 1:1, and the cylinder was sealed and
placed at 60 °C [11,12]. The box was taken out for 60 min and each
Fig. 1. Synthetic chemical equations for CTACYT and CTATYS.

G. Chen et al. / Journal of Molecular Liquids 316 (2020) 113892
3
Table 1
current densities) were obtained from the polarization curves by linear
extrapolation of the anodic and cathodic branches of the Tafel plots at
points 100 mV more positive and more negative than the Ecorr
The CMC and surface tension of different surfactants.
.
Surfactant
CMC/mg/l
The minimum surface tension/mN/m
CTAC
CTACYT
CTATYS
8.27
8.68
8.47
37.4
37.1
37.0
2.7. Specific rotation
The rotation of a substance depends on its properties, its concentra-
tion, the temperature at which it is measured, the wavelength of the
light used and the thickness of the liquid layer of the substance trans-
mitted. Therefore, the specific rotation Dt is usually used to represent
the optical rotation of a compound with a fixed wavelength，the for-
the high interfacial elasticity of the film [20,21]. At room temperature,
the cationic surfactants assimilate to form a double layer, and the hydro-
philic head base and liquid membrane form a hydrated layer. In this
study, the stability was measured based on the initial foam height
(H0) and the height of the foam after 5 min (H5) after mechanical stir-
ring at room temperature. The results are shown in Table 2. The foaming
capacity of the three surfactants is different, and the foaming height of
the same surfactant increases with the increase in concentration,
reaching a maximum of H0 and H5 when the concentration is approxi-
mately 2000 mg/l. Above this concentration, H0 and H5 remain almost
constant. Therefore, 2000 mg/l is known as the best concentration of
foaming ability and foam stability of different surfactant solutions.
CTACYT has the best foaming ability, with H0 reaching 21.4 ml and H5
reaching 20.2 ml, hence the foam volume of CTACYT only decreased
by 0.2 ml. CTATYS's foam stability reached 98.17%. In order to further
understand the stability of the surfactants, the Waring Blender method
was used to determine the concentration of 2000 mg/l surfactant solu-
tion. A 100 ml solution and distilled water were used as the solvent,
and the stirring speed was 7000 r/min for 3 min. Then, the foam height
and half-life of the different surfactant solutions having the same con-
centration were observed. Fig. 3 shows that CTACYT has a significant
foaming capacity, which agrees with the results of the agitation method
[22].
mula for calculating the specific rotation is as follows:
t
½αꢁD
¼
LαcWhere:
α-rotation,
t-Temperature at the time of measurement;
L-Length of sample tube (DM);
c-concentration (g/100 ml).
3. Results and discussion
3.1. Surface activity
As shown in Fig. 2, the minimum interfacial tension values of
CTACYT and CTATYS are almost the same as that of CTAC at high concen-
tration. However, the critical micelle concentrations of CTACYT and
CTATYS were slightly higher than that of CTAC. When the critical micelle
concentration is reached in the surfactant solution, the surface tension
value of the surfactant molecules in the water is almost no longer re-
duced and slightly increased [15]. As shown in Table 1, the surface ten-
sion of the three kinds of surfactants (CTAC, CTACYT, CTATYS) in the
critical micelle concentration is 37.4, 37.1 and 37.0 mN/m, respectively.
3.2. Foaming ability
Table 2
The foaming performance of different concentration of different surfactants.
Previous papers have reported that foaming ability and foam stabil-
ity are related to the properties of interfacial membranes and interfacial
tension [16–18]. When bubbles with the same total surface area are pro-
duced, the low surface tension helps to produce the foam; however, it
can also bubble and burst. The findings of Sonin et al. [19] insist that
the high-frequency interfacial elasticity has a significant impact on the
film thinning process, that is, foam stabilization is mainly due to the
elasticity of the interface film that defines the two phases. This study
also demonstrates the fact that foaming stability is closely related to
Concentration of surfactant /mg/l
Foam height of Ross-Miles/ml
CTAC
H0
CTACYT
H0
CTATYS
H0
H5
H5
H5
400
600
1000
2000
3000
12.7
14.0
16.8
18.3
18.2
11.6
13.1
15.7
18.0
17.8
12.8
15.2
17.3
21.4
19.4
11.9
14.8
16.2
21.2
19.0
13.5
15.9
17.5
21.8
20.3
12.8
15.2
16.7
21.4
19.6
45
450
400
350
300
250
200
150
100
50
6
5
4
3
2
1
0
CTAC
CTACYT
CTACYS
The foam height
The half lifetime
44
43
42
41
40
39
38
37
0
0.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
CTAC
CTACYT
CTATYS
Concentration/g/L
surfactants
Fig. 2. Surface tension-concentration curve of different surfactants at 25 °C.
Fig. 3. The foaming performance of different surfactants with the same concentration.

4
G. Chen et al. / Journal of Molecular Liquids 316 (2020) 113892
100
3.3. Microstructure of foams
90
An optical microscope was used to characterize the microstructure
of a large amount of foam produced by 2000 mg/l of three surfactant so-
lutions at a stirring speed of 7000 r/min for 3 min [23]. The results are
shown in Figs. 4. It is evident from the figures that the foams produced
by the different surfactant solutions exhibit different shapes and vol-
umes. The foam microstructure of CTAC and CTACYT is spherical, and
the foam microstructure of CTATYS is an irregular polygon, indicating
that the structure of the amino acid has different effects on the micro-
structure of the foam. This can be ascribed to the fact that foam stability
is controlled by the liquid film discharge process. Compared with other
surfactants, CTAC has the fastest drainage process and CTACYT has the
slowest drainage process; hence, CTACYT produces foam with high sta-
bility. Two hydrophilic groups have been added to CTACYT and CTATYS.
One functional group is an amino group (−NH2) and the other is a car-
boxyl group (-COO−), in order that the molecular structure makes
CTACYT and CTATYS more hydrated than conventional anionic (cat-
ionic) ionic surfactants. When adsorbed at the gas-liquid interface, the
molecules of the liquid film can be hydrogen-bonded or entangled
with each other, so that the surface film has certain strength, thereby
providing better foaming ability and foam stability.
80
70
60
50
40
30
20
CTAC
CTACYT
CTATYS
0
10
20
30
t/min
40
50
60
Fig. 5. The emulsion capability of surfactants in the CMC with same concentration.
3.5. Corrosion inhibition
3.4. Emulsification power
Corrosion inhibitors are the most commonly used method of
inhibiting metal corrosion. In recent years, with the improvement of
human environmental awareness and the development of sustainable
development, the research and development of new and efficient envi-
ronmental inhibitors has become a hot spot [25]. The inhibition effi-
ciency obtained by weight loss method of chiral cationic surfactants,
CTACYT and CTATYS, is 96.72% and 90.22%, respectively, which is supe-
rior to that of CATC. Probably because there are not only nitrogen atoms
in the molecular structure of CTACYT, but also sulfur atoms. The syner-
gistic action of these two ions makes the Fe-interface more favorable for
the adsorption of charged CTACYT molecules, making them easier to co-
adsorb with metal ions [26,27], and making them more effective in cor-
rosion inhibition. Therefore, it is inferred that the adsorption of CTACYT
on the metal surface may be a chemical adsorption in addition to phys-
ical adsorption, while the adsorption of CTATYS is physical adsorption.
The anodic and cathodic polarization curves for a mild steel elec-
trode at 298 K were shown in Fig. 6. Table 4 shows the electrochemical
corrosion kinetic parameters, i.e., corrosion potential (Ecorr), cathodic
and anodic Tafel slopes (βa, βc) and corrosion current density Icorr ob-
tained by extrapolation of the Tafel lines. The inhibition efficiency (%)
is also calculated from the following equation:
The water evolution rate may reflect the emulsifying ability of the
surfactant, that is, the smaller the water evolution rate, the stronger
the emulsifying ability of the system to be tested, and on the contrary,
the worse the emulsifying ability of the system. The stability of the
emulsion formed between the surfactant solution and the oil phase de-
pends on the chemical structure of the surfactant and oil [24]. The emul-
sifying ability of the surfactant is strongest at the micelle concentration.
Therefore, we have studied the emulsifying ability of three surfactants
at different micellar concentrations, as shown in Fig. 5. With the exten-
sion of time, the water evolution rate of the emulsion formed by the
CTAC solution and dehydrated degassed crude oil increased continu-
ously. After 20 min of rapid demulsification, the water evolution rate
of the emulsion solution reached over 80%. However, the water evolu-
tion rate of the emulsion formed by the CTACYT and CTATYS solutions
and the dehydration and degassing crude oil was less than 60% at
20 min. Also, the water evolution rate had a tendency to be stable
with the prolongation of time. It can be seen that CTACYT and CTATYS
had strong emulsifying ability and could form stable emulsion with
dehydrated and degassed crude oil. Also, for the emulsifying ability,
the separation time become longer and the emulsifying ability was im-
proved. With the introduction of amino acids, the hydrophilicity in-
creases, the adsorption is saturated, a dense film is formed at the
water/oil interface, and the strength of the interfacial film is increased,
which makes the separation time longer; that is, the emulsifying ability
becomes stronger.
Icorr−I
Eð%Þ ¼
corrðiÞ ꢀ 100
ð1Þ
Icorr
where Icorr and Icorr(i) are corrosion current densities obtained in the ab-
sence and presence of inhibitors, respectively. As it was expected both
(a)
(b)
(c)
Fig. 4. Microscope morphology of CTAC(a), CTACYT(b) and CTATYS(c).

G. Chen et al. / Journal of Molecular Liquids 316 (2020) 113892
5
Table 5
Specific optical rotation of chiral amino acid surfactants.
Chiral substance
Solvent
c(mmol/l)
α
[α]t D
L-cysteine
L-tyrosine
CTACYT
1 mol/l
1 mol/l
1 mol/l
1 mol/l
1
1
1
1
+0.16°
−0.62°
+0.18°
−0.58°
+8.0°
−12.4°
+8.1°
CTATYS
−11.6°
4. Conclusions
First of all, with the introduction of amino acids, the hydrophilicity
increases, the adsorption is saturated, a dense film is formed at the
water/oil interface, and the strength of the interfacial film is increased,
so that the separation time becomes longer; that is, the emulsifying abil-
ity becomes stronger. Both CTACYT and CTATYS surfactants have better
emulsifying ability and foam stability than CTAC. Secondly, the CTACYT
and CTATYS surfactants have the functional group structure of amino
acids, which has better corrosion inhibition effect than CTAC. The corro-
sion inhibition efficiencies of CTACYT and CTATYS are 96.72% and
90.22%, respectively. The result obtained by the electrochemical method
is that the instantaneous corrosion inhibition rate is different from the
average corrosion inhibition rate obtained by the weightlessness
method, but the corrosion inhibition trends measured by the two
methods are consistent. Besides, the new chiral surfactants remain the
chiral character, and the specific optical rotations of CTACYT and
CTATYS were 8.1° and 11.6°, respectively. This work will benefit the re-
lated research in this field.
Fig. 6. The polarization curve of steel in HCl solution containing the surfactants at 20 mg/l.
anodic and cathodic reactions of mild steel electrode corrosion were
inhibited by the increase of the surfactants. This result suggests that
the addition of the surfactants reduces anodic dissolution and also re-
tards the hydrogen evolution reaction [13], and CTACYT and CTATYS
are much better than that of CTAC, which is consisted with the results
above. Comparing the data from Table 3 and Table 4, we can find the in-
hibition efficiency obtained from potentiodynamic polarization are
quite different from those calculated from weight-loss measurements,
which is attributable to the fact that the weight-loss method gives aver-
age corrosion rate, whereas electrochemical method gives instanta-
neous corrosion rates. These differences may arise frequently because
of the difference in the time required to form an adsorbed layer of inhib-
itors on metal surface [13,14].
CRediT authorship contribution statement
Gang Chen: Conceptualization, Methodology. Jiao Yan: Data
curation, Writing - original draft. Yun Bai: Visualization, Investigation.
Sanbao Dong: Software, Validation. Dengwei Liu: Investigation. Jie
Zhang: Supervision. Shidong Zhu: Software. Chengtun Qu: Writing -
review & editing.
3.6. Specific rotation
It can be seen from Table 5 that the modification of the proceeds of
the chiral amino acid surfactant is slightly different from the rotation
of cysteine, and the tyrosine ratio is almost unchanged. The interpreta-
tion of quaternary ammonium salt cationic opponents on the carbon
atoms did not produce electronic polarization phenomenon. In the pre-
vious studies, they thought that the bigger the spiral electronic polariza-
tion, the more susceptible it is to the effects of light and electromagnetic
fields, hence the optical rotation [28].
Declaration of competing interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influ-
ence the work reported in this paper.
Acknowledgments
This work was financially supported by the grants from National
Natural Science Foundation of China (21376189, 51974245) and
Shaanxi Key Research and Development Program (2019KW-061). And
we thank the work of Modern Analysis and Testing Center of Xi'an
Shiyou University.
Table 3
Corrosion inhibition efficiency and corrosion rate of the surfactants at 20 mg/l.
Cationic surfactants
Wcorr (g·m−2·h−1
)
Ew (%)
Blank
CTAC
CTACYT
CTATYS
17.07
1.93
0.56
1.67
/
88.70
96.72
90.22
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