gemini review.pdf
TRANSCRIPT
-
7/25/2019 Gemini review.pdf
1/14
RE V I E W A RT I CL E
A Review of Gemini Surfactants: Potential Applicationin Enhanced Oil Recovery
Muhammad Shahzad Kamal1
Received: 16 May 2015 / Accepted: 7 December 2015/ Published online: 26 December 2015 AOCS 2015
Abstract Gemini surfactants are a group of novel sur-
factants with more than one hydrophilic head group andhydrophobic tail group linked by a spacer at or near the
head groups. Unique properties of gemini surfactants, such
as low critical micelle concentration, good water solubility,
unusual micelle structures and aggregation behavior, high
efficiency in reducing oil/water interfacial tension, and
interesting rheological properties have attracted the atten-
tion of academic researchers and field experts. Rheological
characterization and determination of the interfacial ten-
sion are two of the most important screening techniques for
the evaluation and selection of chemicals for enhanced oil
recovery (EOR). This review deals with rheology, wetta-
bility alteration, adsorption and interfacial properties ofgemini surfactants and various factors affecting their per-
formance. The review highlights the current research
activities on the application of gemini surfactants in EOR.
Keywords Gemini surfactants Enhanced oil recovery
Rheology Interfacial tension Surface tension
Introduction
Background of Enhanced Oil Recovery (EOR)
Enhanced oil recovery (EOR) or tertiary oil recovery is a
technique to recover additional oil remaining in reservoirs
after primary and secondary recovery processes. In primary
oil recovery, oil is recovered using natural pressure of oil
reservoirs, while in secondary recovery water is injected todisplace the oil. The EOR methods that have been used are
summarized in Fig.1. Thermal EOR, gas injection, and
chemical EOR (cEOR) are the most commonly used EOR
methods. In cEOR, a high recovery rate can be achieved by
increasing the dimensionless capillary number, which is
defined as the ratio of viscous forces to inertial forces [1
3]. An ultra-low interfacial tension (IFT) in the range of
10-3 mN/m is required to obtain a capillary number high
enough for effective oil displacement from reservoir rock
and pore spaces [412]. Such a low interfacial tension can
be achieved by using a suitable surfactant and/or a com-
bination of surfactants [1316]. As indicated by the patentsgranted, the use of surfactants in EOR began almost
80 years ago [17]. Surfactants used in the early 1960s were
made by the direct sulfonation of crude oil or organic
synthesis of alkyl/aryl sulfonates [17]. Even though the use
of surfactants in EOR has been researched extensively, the
number of surfactant EOR projects decreased significantly
due to the low oil prices from late 1980s to early 2000.
However, the depletion of oil reserves, the advancement of
technologies, increasing demand for oil, and high oil prices
have encouraged researchers to focus on surfactant EOR
[1821].
The majority of the reported surfactants used in EOR are
ethoxylated and propoxylated sulfates and sulfonates. Even
though the displacement efficiency of sulfonates with a
higher equivalent weight is better [22], sulfonates with high
equivalent weights are insoluble in water, and thus sul-
fonates with lower equivalent weights have to be used as
sacrificial agents and solubilizers. Therefore, mixtures of
surfactants are used in EOR formulations. This type of
formulation, however, may lead to chromatographic sepa-
ration in the reservoir during displacement. Hence, in
& Muhammad Shahzad [email protected]; [email protected]
1 Center for Integrative Petroleum Research, King FahdUniversity of Petroleum and Minerals, Dhahran 31261,Saudi Arabia
1 3
J Surfact Deterg (2016) 19:223236
DOI 10.1007/s11743-015-1776-5
http://crossmark.crossref.org/dialog/?doi=10.1007/s11743-015-1776-5&domain=pdfhttp://crossmark.crossref.org/dialog/?doi=10.1007/s11743-015-1776-5&domain=pdf -
7/25/2019 Gemini review.pdf
2/14
conventional surfactant formulations, interfacial tension is
either not reduced sufficiently to remove trapped oil or the
slug may lose its integrity during flooding [22]. High-temperature and high-salinity conditions of reservoirs are
another major challenge in the application of surfactant
flooding. Surfactants can precipitate by interacting with
divalent cations present in the reservoir brine [23,24], and
can thermally degrade at high-reservoir temperatures [25].
Surfactant retention in the reservoirs has an adverse effect
on the economics of EOR. In summary, an ideal candidate
surfactant for EOR must be compatible with the reservoir
brine, must be able to generate ultra-low interfacial tension
between water and oil, has low retention on reservoir rock,
and has long-term thermal stability under reservoir
conditions.
Background of Gemini Surfactants
A novel class of surfactants referred to as gemini sur-
factants has drawn the attention of EOR experts lately due
to their unique properties. They have been used in a range
of applications due to their unique properties [2634].
Gemini surfactants were first identified by Bunton et al. and
named in 1991 by Menger and Littau [3538]. They con-
tain more than one hydrophilic head group and
hydrophobic tail group linked by a spacer at or near the
head groups [3947]. A schematic representation of agemini surfactant is shown in Fig. 2. The attachment of the
spacer group increases the hydrophobicity of gemini
surfactants relative to that of the constituent monomeric
units [48]. The most widely studied gemini surfactants are
m-s-m type containing quaternary ammonium, where s and
mrepresent the number of carbon atoms of the spacer and
the alkyl chain, respectively [49, 50]. For example, the
gemini surfactants alkanediyl-a,x-bis(dodecyldimethyl-
ammonium bromide) with alkanediyl spacer groups C2H4
and C8H20, are referred to as 12-2-12, and 12-8-12,respectively [48]. The hydrophilic head group can be
cationic, non-ionic, anionic, or zwitterionic. The
hydrophobic tail can be short or long and the spacer group
can be polar (polyether) or non-polar (aliphatic or aro-
matic), and rigid (benzene) or flexible (methylene) [51].
Length of the spacer group, which maintains and controls
the separation between the two head groups, can vary
between C2 and C12. Most of the work on gemini sur-
factants has focused on their physicochemical properties
such as high solubilization capacity [52, 53], unique
micelle structure and aggregation behavior [45], high sur-
face activity [37], and interesting rheological properties[5456].
Shukla and Tyagi reviewed anionic gemini surfactants,
their synthesis, and properties such as the CMC, surface
activity, and foaming properties [51]. Zana reviewed the
behavior of dimeric and oligomeric surfactants in aqueous
solution [43]. Kumar and Tyagi reviewed the applications
of dimeric surfactants in genetics, cosmetics and personal
care, paints, and textile industries [57]. Hait and Moulik
reviewed the synthesis, structure, CMC, and the surface
active properties of gemini surfactants [58]. A large num-
ber of experimental studies on the properties of aqueous
solutions of gemini surfactants have been reported. Thedetermination of the properties of the liquidliquid inter-
face, particularly the oilwater interface, is the main area
of research in laboratories conducting research on gemini
surfactants [5962]. This review highlights the interfacial
properties, adsorption, and rheological behavior of gemini
surfactants under different conditions. As it is not possible
to perform expensive and time-consuming oil recovery
experiments for each surfactant under different conditions,
IFT measurements, adsorption, and rheological character-
ization are used as screening tools for the selection of EOR
chemicals in the oil industry. Data obtained from adsorp-
tion experiments, and rheological and interfacial mea-
surements are widely used as guidelines for the selection of
suitable surfactants and optimum surfactant formulations.
Increases thecapillary number
Polymer
Viscosifies thedisplacing fluid
EOR
Improves themobility ratio
ChemicalThermal
Surfactant
Alters the wettability
Decreasesinterfacial tension
Gas
Alkali
Fig. 1 Types of EOR methods
Fig. 2 Schematicrepresentation of a geminisurfactant [161]
224 J Surfact Deterg (2016) 19:223236
1 3
-
7/25/2019 Gemini review.pdf
3/14
Fundamentals of Gemini Surfactants
Structure
In the last decade, a rich variety of cationic, anionic,
zwitterionic, and nonionic gemini surfactants have been
developed and commercialized. Structures of some of the
typical gemini surfactants are given in Table1. Gemini
surfactants can have phosphate, sulfonate, carboxylate,
sulfate, ethyl ammonium, methyl ammonium [63], pyrro-
lidinium [64], hexahydropyridine [64], and imidazolium[64] head groups. Common spacers of gemini surfactants
are given in Table2. Oligostyrene [65], oligo (ethylene-
propylene glycol), and poly (dimethyl siloxane) [66] are
some typical examples of hydrophobic tail groups. Gemini
surfactants have widespread applications in the fabrication
of high-porosity materials [67], textiles, emulsifiers, wet-
ting processes, leather-finishing, and skin and personal care
products [68].
Comparison of Gemini Surfactants
with Conventional Surfactants
Before comparing gemini surfactants with conventional
surfactants, it is important to have an understanding of the
fundamental properties of surfactants which are used to
characterize them. An understanding of the critical micelle
Table 1 Typical structures ofrepresentative geminisurfactants
Structure of surfactant Type References
Cationic [64]
Anionic [155,162]
Zwitterionic [163]
Nonionic [164]
Table 2 Common spacers of gemini surfactants
Entry Spacer References
1 Azobenzene [156]
2 Ethylene oxide [147]
3 Perylene tetracarboxylic diimide [65,165]
4 Stilbene [65]
5 Tetracarboxylic diimide [65]
6 Polyoxyethylene [166]
7 2-Butynyl [38]
8 Methylene [51]
9 Polyether [51]
J Surfact Deterg (2016) 19:223236 225
1 3
-
7/25/2019 Gemini review.pdf
4/14
concentration (CMC), hydrophilic/lipophilic balance
(HLB), Krafft temperature, and the molecular packingparameter can greatly aid in understanding the performance
of surfactants. R ratio and the solubilization ratio of sur-
factants are also used for surfactant characterization.
CMC is the concentration of a surfactant above which
the formation of micelles takes place [69]. In solution
chemistry, CMC is widely used to compare the effective-
ness of surfactants for their desired applications [70].
Critical micelle concentrations of gemini surfactants are
typically 10100 times lower than the corresponding value
for conventional monomeric surfactants [71]. CMC of a
range of conventional and gemini surfactants are given in
Table3. Among the gemini surfactants, anionic surfactantshave a lower CMC compared to their cationic counterparts.
The Krafft temperature, also referred as the critical micelle
temperature, is defined as the minimum temperature at
which micelle formation takes place. Below the Krafft
temperature, CMC is not attained and thus, micelles cannot
form [72]. A surfactant is considered soluble if its Krafft
temperature is below room temperature [51] and for gemini
surfactants it is much lower than that of monomeric sur-
factants [43]. Krafft temperatures below 0 C have been
reported for many gemini surfactants containing both
hydrophobic and hydrophilic spacers [7381].The HLB value of surfactants is a measure of the degree
of hydrophilicity or lipophilicity. An HLB value of 1
corresponds to a completely hydrophobic molecule,
whereas a completely hydrophilic molecule has an HLB
value around 40. Although high hydrophilicity assists in
the dissolution of surfactants, it adversely affects the per-
formance of surfactants in reducing IFT [17]. HLB values
of surfactants used for oil displacement are typically in the
range of 69 [82]. The HLB value can be adjusted by
changing the tail length and modifying the head group.
The structure of surfactants can be correlated with their
interfacial performance using the packing parameter [82].The packing parameter (P) depends on the relative area of
the surfactant head group (ao) and the tail group (VH/lc) and
their relationship is shown by Eq. 1. When P approaches
one, the area of the hydrophilic groups will be equal to the
area of lipophilic groups and the surfactant will be com-
pactly arranged at the interface minimizing the IFT. Typ-
ically, the P value of a conventional surfactant is between
0.3 and 0.6, which is not suitable for oil displacement.
P value of potential surfactants for EOR applications
Table 3 CMC values of conventional and gemini surfactants
Entry Surfactant CMC/mM References
1a C12H25N?(CH3)3 Br
- 16 [39]
2 C12H25N?(CH3)3 Cl
22 [39]
3 C16H33N?(CH3)3 Br
1 [39]
4 C12H25OSO3 Na? 8 [39]
5 C2H4(C12H25N?Me2 Br-)2 0.84 [48]
6 C3H6(C12H25N?Me2 Br
-)2 0.87 [48]
7 C4H8(C12H25N?Me2 Br
-)2 1.09 [48]
8 C6H12(C12H25N?Me2 Br
-)2 1.01 [48]
9 C8H16(C12H25N?Me2 Br
-)2 0.83 [48]
10 C10H20(C12H25N?Me2 Br
-)2 0.63 [48]
11 C12H24(C12H25N?Me2 Br
-)2 0.37 [48]
12 C12H25N?(CH3)2(CH2)16N
?(CH3)2C12H25 2Br- 0.12 [39]
13 C16H33N?(CH3)2(CH2)2N ?
(CH3)2C16H33 2Br- 0.003 [39]
14 C12H25N?(CH3)2(CH2)2O(CH2)2N
?(CH3)2C12H25 2Cl- 0.5 [39]
15 C16H33N?(CH3)2(CH2)5N
?(CH3)2C16H33 2Br- 0.009 [39]
16 C16H33N?(CH3)2(CH2)2O(CH2)2N
?(CH3)2C16H33 2Br- 0.004 [39]
17 C16H33N?(CH3)2CH2(CH2OCH2)3CH2N
?(CH3)2C16H33 2Br- 0.02 [39]
18 C12H25N?(CH3)2CH2CH(OH)CH2N
?(CH3)2C12H25 2Br- 0.8 [39]
19 C12H25N?(CH3)2CH2C6H4CH2N
?(CH3)2C12H25 2Br- 0.03 [39]
20 C12H25N?(CH3)2CH2CH(OH)CH(OH)CH2N
?(CH3)2C12H25 2Br- 0.7 [39]
21 C12H25N?(CH3)2CH2CH(OH)CH2N
?(CH3)2CH2CH(OH)CH2N?(CH3)2C12H25 3Cl
- 0.5 [39]
22 C12H25OPO2-O(CH2)6OPO2
-OC12H25 2Na? 0.4 [39]
23 C10H21OCH2CH(OSO3-)CH2O(CH2)2OCH2CH(OSO3
-)CH2OC10H21 2Na? 0.01 [39]
a Entries 14 are for conventional surfactants
226 J Surfact Deterg (2016) 19:223236
1 3
-
7/25/2019 Gemini review.pdf
5/14
should be adjusted to one, which can be accomplished by
increasing VH, and by decreasing lc and ao. The value oflccan be deceased by increasing the degree of branching and
aocan be decreased by using a week hydrophilic group or a
zwitterion [82].
P VH
lc ao1
In addition to the above mentioned properties, gemini
surfactants have better wetting and foaming properties,
unusual aggregation morphologies, better solubilizing
properties, better foaming properties, and better rheological
properties compared to conventional surfactants [73, 83
92]. Gemini surfactants are three orders of magnitude more
efficient in lowering the surface tension of water, and more
than two order of magnitude more dynamic in the inter-
facial performance compared to conventional surfactants
[57]. Due to the unique properties of gemini surfactants,
they have been referred to as a new generation of surfac-
tants and have shown great promise for industrial appli-cations [93].
The following sections highlight those properties of
gemini surfactants which are used for screening them for
EOR applications.
Interfacial Tension
This section highlights the interfacial properties of gemini
surfactants and various factors affecting IFT. Interfacial
evaluation can be used to determine the suitability of sur-
factants for chemical EOR. If the IFT between surfactantsolution and crude oil is high, the surfactant can be ruled
out at the initial stages.
Gao et al. investigated sulfate based gemini surfactants
and demonstrated that they have an extraordinary tolerance
of salinity [17]. Even with a brine of 20 % NaCl and 5 wt%
CaCl2 no phase separation or precipitation was observed.
In addition, it was found that the interfacial tension is ultra-
low towards the higher end of salinity, which is extremely
desirable in high-temperature and high-salinity environ-
ments. As the synergy between gemini surfactants and
conventional surfactants provide mutual benefits, they can
be used as co-solvents and co-surfactants.At low surfactant concentrations, surfactant molecules
remain flat at the interface. However, with increasing sur-
factant concentration they tend to orient themselves at the
interface. At concentrations close to the CMC, surfactant
molecules associate into larger aggregates of molecules
also known as micelles. A further increase in the surfactant
concentration will only increase the rate of formation of
micelles and there will be no further adsorption of the
surfactant at the interface. Gemini surfactants decrease IFT
with increasing concentration and it is important to note
that gemini surfactants achieve the minimum IFT at very
low concentrations, which will have a positive impact on
the economics of surfactant flooding. Gemini surfactants
can achieve IFT in the range of 10-3 mN/m at 0.02 %
concentration whereas conventional surfactants will require
0.22 wt% [17]. At a gemini surfactant concentration of
0.423 mml/L an IFT lower than 10-4 mN/m can beachieved [94]. However, it has been reported that the
decrease in the interfacial tension with increasing surfac-
tant concentration is limited to a particular concentration
range. Further increase in the surfactant concentration can
increase the IFT. At lower concentrations, HLB of the
interface changes due to the adsorption of gemini surfac-
tants at the interface, which results in the lowering of IFT.
Increasing the concentration of the surfactant above a
particular concentration can increase the rigidity of inter-
face film, which increases the IFT. However further
investigations are required to understand the mechanism
[22].Due to adsorption and desorption of the surfactant at the
interface, it will take some time to achieve the equilibrium
IFT value. Gemini surfactants achieve equilibrium IFT val-
ues in a shorter time compared to conventional surfactants.
Although the addition of polymers increase the equilibrium
time, equilibrium IFT values are not affected by their addi-
tion [17]. Temperature can also affect the dynamic IFT, and
time required to achieve the equilibrium IFT can be reduced
at high temperature [44]. For example, a gemini surfactant
took 50 min to achieve the equilibrium IFT value at 45 C,
whereas the same takes only 15 min at 70 C [44].
Temperature has a strong effect on the IFT, and IFTgoes through minima with increasing temperature for most
gemini surfactants. An initial decrease and then an increase
in the IFT are associated with a change in the distribution
of surfactants in oil, water, and emulsions. Emulsions may
invert from oil-in-water to water-in-oil with the variation of
temperature. The temperature corresponding to a minimum
in interfacial tension is known as the phase inversion
temperature (PIT) [44]. At temperatures below the PIT,
adsorption of the surfactant increases with increasing
temperature resulting in the lowering of IFT. However, at
temperatures above the PIT, further increase in the tem-
perature may lead to the diffusion of the surfactant away
from the interface into the oil phase resulting in an increase
of the IFT.
Performance of a surfactant can be improved through
the synergistic interaction with another surfactant. Gemini
surfactants can have excellent synergy with other gemini
surfactants and conventional surfactants when the interac-
tions are attractive. Ye et al. showed that the temperature
effects on IFT can be diminished by using a mixture of
gemini surfactants [44]. This is attributed to the formation
J Surfact Deterg (2016) 19:223236 227
1 3
-
7/25/2019 Gemini review.pdf
6/14
of mixed micellar aggregates with a compact arrangement.
Such a surfactant can be used as a co-solvent, which can
enhance the solubility of the main surfactant or the co-
surfactant improving their performance.
Gemini surfactants are more effective in reducing the IFT
of the kerosene-water interface in salt solutions as compared
to salt-free solutions. This is due to the modification of HLB
of the interface and compression of the electrical double
layer due to the added salts. However, gemini surfactants
showed similar behavior in salt-free and salt solutions in
decreasing the IFT of the hexadecane and water interface
[22]. Thus, the nature of the lipophilic phase, i.e., crude oil, is
also important in the decrease in IFT.
In summary, gemini surfactants are more effective in
decreasing the IFT under varying conditions compared to
monomeric surfactants. Regarding EOR applications, the
most important property of gemini surfactants is achieving
ultra-low interfacial tension at low surfactant concentra-
tions. Low surfactant concentration reduces the required
amount of surfactant and the cost of surfactant flooding,
which is the ultimate goal of any EOR process.
Wettability Alteration
Wettability is defined as the tendency of a liquid to pref-
erentially adhere or stick to a solid surface in the presence
of other liquids [95], which is the major factor controlling
the location and flow of oil in reservoirs. An oil reservoir
can be water-wet, oil-wet, or mixed-wet depending upon
the nature of the oil and the type of the formation. The fact
that the maximum amount of oil can be recovered from
water-wet reservoirs is well established; however, majority
of the carbonate reservoirs is oil-wet to mixed-wet. Wet-
tability is normally determined by measuring the contact
angle between a solid surface and an oil droplet. Data inTable4show that only 8 % of the carbonate reservoirs are
water-wet and the remaining are intermediate-wet to
strongly oil-wet reservoirs. Surfactants alter the wettability
of rocks from oil-wet to water-wet and enhance the spon-
taneous imbibition [96,97].
Wettability alteration takes place by ion-pair formation
and adsorption of the surfactant on the rock surface [ 98,
99]. When electrostatic interactions exist between the head
group of the surfactant and the adsorbed crude oil
components, ion-pair formation is the main mechanism of
wettability alteration. However, in the absence of electro-
static interactions, hydrophobic interactions between the
tail of the surfactant and the adsorbed crude oil components
are responsible for wettability alteration [98]. Effectiveness
of a surfactant in altering the wettability depends on the
ionic nature of the surfactant. In the oil-wet core of chalk
reservoirs, cationic surfactants perform better than anionicsurfactants in altering the wettability [96,100]. The authors
hypothesized that the wettability alteration is due to ion-
pair formation between the head of the cationic surfactant
and certain components of the crude oil. On the other hand,
anionic surfactants form a monolayer on the surface of
carbonate rock through hydrophobic interactions between
the tail of the surfactant and crude oil components. Ion-pair
interactions are much stronger compared to hydrophobic
interactions; therefore, cationic surfactants are more
effective in altering the wettability of carbonate rock.
Efficacy of gemini surfactants in altering the wettability
was investigated by several researchers [101,102]. Salehiet al. investigated the effects of anionic gemini surfactants
on wettability alteration of Berea sandstone and compared
the results with those obtained using a conventional sur-
factant [101]. They found that ion-pair formation is the
main mechanism of wettability alteration, which can be
improved by increasing the charge density on the head
groups (Fig. 3). Contrary to carbonate rock, ion-pair for-
mation is the main mechanism involving anionic surfac-
tants in the case of sandstone rock. Due to the presence of
two hydrophilic head groups and two hydrophobic tails,
gemini surfactants can further improve the wettability
alteration. Research on the wettability alteration of car-bonate rocks by gemini surfactants is limited and needs
more experimental investigation.
Adsorption
Adsorption of surfactants on reservoir rock surfaces, which
decreases the concentration of the surfactant in the flooding
liquid, is a major hurdle that has to be overcome [103
Fig. 3 Ion-pair formation between crude oil components and ananionic gemini surfactant [101]
Table 4 Distribution of carbonate reservoirs [95]
Contact angle () Reservoirs (%)
Water-wet 080 8
Intermediate-wet 80100 12
Oil-wet 100160 65
Strongly oil-wet 160180 15
228 J Surfact Deterg (2016) 19:223236
1 3
-
7/25/2019 Gemini review.pdf
7/14
106]. Adsorption of cationic, non-ionic, anionic, and
amphoteric surfactants on sandstone and carbonate rock
surfaces has been studied widely and the mechanism of
adsorption has been discussed in a number of publications
[16,107109]. Adsorption of surfactants on reservoir rock
surfaces depends on the charge on the surfactant,
hydrophobicity of the surfactant, charge on the rock sur-
faces, pH, salinity, temperature, and interactions betweenthe surfactant and the rock surfaces [110]. Static and
dynamic adsorption tests are performed to screen chemi-
cals for EOR applications. Static adsorption tests are sim-
ple and normally used for initial screening of EOR
chemicals. In static adsorption tests, a small amount of a
crushed rock sample is shaken in a surfactant solution for a
specific time. The adsorption density is found by the dif-
ference in concentration of the surfactant before and after
equilibration. Surfactant concentration can be determined
by conductivity measurements, surface tension measure-
ments, gas chromatography, total carbon analysis (TOC),
two phase titration, UV spectroscopy, gel permeationchromatography, and high performance liquid chromatog-
raphy (HPLC) [16,111117]. As crushed rock has a higher
surface area than a consolidated core, static adsorption tests
give higher values of adsorption than dynamic adsorption
tests [118]. Dynamic adsorption tests are typically per-
formed using core flooding experiments, which are time
consuming and used only for selected promising surfac-
tants. For EOR applications, surfactant adsorption density
should be less than 1 mg/g-rock [119].
Behrens studied the adsorption of the anionic gemini
surfactant Aerosol OT on kaolinite using the surfactant
concentration determination method [110]. Adsorption ofthe anionic gemini surfactant on kaolinite increases with
increasing salinity due to the increased ionic strength. Gao
and Sharma investigated the adsorption behavior of sulfate
gemini surfactant on Berea sandstone rock in the presence
of 10,000 mg/L of NaCl [17]. They found that the Lang-
muir adsorption model can be used to describe the
adsorption behavior of the anionic gemini surfactant,
similar to that of a conventional surfactant. The adsorption
process of the gemini surfactants can be divided roughly
into three regions. At low surfactant concentration (region
I), the adsorption of the gemini surfactants increases lin-
early and obeys Henrys Law. The surfactant molecules are
adsorbed as individual ions and interactions do not take
place between adsorbed molecules. Only electrostatic
interactions between the head groups and the charged sites
are present. In Region II, adsorption takes place much
faster due to lateral interactions between the tail groups of
the surfactant molecules, in addition to the electrostatic
interactions. A plateau is obtained in Region III and further
increase in the surfactant concentration has little or no
effect on the adsorption density. This is due to the
formation of micelles that act as chemical sinks for addi-
tional surfactant. Anionic gemini surfactants also show
lower equilibrium adsorption compared to conventional
surfactants on Berea sandstone. Alkyl chain length and the
spacer have a strong influence on the adsorption of gemini
surfactants. Surfactants with longer alkyl chains and spacer
groups have a higher adsorption due to their lower solu-
bility and stronger interactions with the rock surface.Pahi et al. compared the adsorption of the alkylbenzene
monomeric and gemini surfactants [120]. They also
observed that gemini surfactants have similar adsorption
behavior but with a lower equilibrium adsorption compared
to conventional monomeric surfactants. The maximum
amount of adsorbed gemini surfactants was found at the
CMC. Rosen and Li studied the adsorption of two cationic
gemini surfactants on limestone and clay (Na-montmoril-
lonite) [121]. They found that the adsorption of the gemini
surfactants on clay is similar to that of a conventional
surfactant with similar hydrophilic and hydrophobic
groups.Gao and Sharma studied the adsorption behavior of the
anionic disulfate gemini surfactant and the various factors
affecting the adsorption on a Berea sandstone core [118].
The adsorption process of the sulfate gemini surfactant is
also characterized by three distinct regions. The disulfate
gemini surfactant has a lower adsorption density compared
to the corresponding conventional single tail surfactant
under similar conditions. The adsorption density depends
on the hydrophilicity and the dual-head group structure of
gemini surfactants. Due to their higher hydrophilicity, the
gemini surfactants have a higher tendency to go into the
aqueous phase as compared to conventional surfactants,and therefore, they have a lower tendency to adsorb on
solid surfaces. One gemini molecule can interact with more
than two adsorption sites and saturate the surface more
efficiently due to the presence of two head groups. They
also observed that the adsorption density of the gemini
surfactant increases in the presence of salts. The increase in
the adsorption density in the presence of salts is due to the
suppression of electrostatic interactions between the head
group and double layer formed at the surface by the added
sodium ions, the promotion of various aggregates, and
reduction in the solubility [118]. The molecular structure of
gemini surfactants also affects their adsorption on reservoir
rock surfaces. An increase in the length of the tail of the
surfactant increases the lateral interactions and thus,
increases the adsorption density. In addition, longer
hydrocarbon chains also reduce the solubility in the bulk
aqueous phase, thus, increasing the tendency of adsorption
on solid surfaces.
In summary, the adsorption behavior of gemini surfac-
tants depends mainly on the molecular structure, salinity,
temperature, and the type of interactions between the
J Surfact Deterg (2016) 19:223236 229
1 3
-
7/25/2019 Gemini review.pdf
8/14
surfactant molecules and the solid surface. Due to their
higher hydrophilicity and the dual headgroup, they have
lower adsorption densities compared to conventional single
tail surfactants.
Rheology
Rheology is another important property that can be used for
the selection of chemicals for EOR. Water-soluble poly-
mers are used to prepare displacing fluids with a high
viscosity, which are required to displace reservoir oil [122
131]. Due to their unique aggregation behavior, gemini
surfactants can also improve the rheological properties of
displacing fluids. This approach has the advantage of using
a single slug of gemini surfactants instead of a combination
of surfactants and polymers. Both steady shear and
dynamic rheology are important for EOR applications.
Elasticity of a material has been proven recently to assist in
the recovery of residual trapped oil [132137].A large amount of research has been conducted on steady
shear rheology, extensional rheology, and rheo-scattering of
worm-like micelles [138]. Gemini surfactants have better
rheological properties compared to conventional surfactants.
Although dilute solutions of ionic and non-ionic conven-
tional surfactants behave as a Newtonian fluid with viscosity
slightly higher than that of water, dilute solutions of gemini
surfactants are much more viscous. Gemini surfactants form
aggregates that are less curved compared to corresponding
monomeric surfactants. Gemini surfactants form worm-like
micelles which are also referred to as giant, rod-like, thread-
like, or polymer-like micelles [139145]. They have a net-work structure similar to polymers, except that these
micelles continuously break and reform [49]. When worm-
like micelles are subjected to stress, they undergo two types
of stress relaxation processes. They may undergo reptile-like
motion or reversible scissions that occur at two time scales
known as the reputation time and scission time. The vis-
coelastic behavior of worm-like micelles canbe described by
the Maxwell model [49]. Aggregate curvature decreases
with increasing concentration of the surfactant, and electron
micrographs show that these micelles may be several
micrometers long [83,146]. However, micelles of conven-
tional surfactants remain spherical even at considerably high
concentrations [147]. Micelles of gemini surfactants trans-
form from spherical to worm-like with increasing concen-
tration, and both types coexist as the transformation is not
abrupt. However, with increasing concentration, the number
of spherical micelles per unit volume decreases. Therefore,
the solution shows viscous behavior due to the formationof a
transient network [83], which has been confirmed by others
[84]. Length of the worms varies from 100 to 400 nm while
diameter is normally the same for each worm-like micelle.
While for the 12-s-12 series surfactants the shape of micelles
change from elongated to spherical [45], for the 16-s-16
series surfactants, worm-like and spherical micelles co-exist
at specific concentrations. Micelles change from elongated
to spherical when the length of the spacer is increased [ 148,
149]. In general, gemini surfactants are capable of producing
worm-like micelles as well as spherical micelles [150].
Gemini surfactants with longer carbon chains have higherviscosity compared to those with shorter carbon chains [83].
Gemini surfactants with long saturated alkyl chains have a
high Krafft point. In some cases, the Krafft temperature is
even higher compared to the corresponding monomeric
surfactant. For example, the Krafft temperature of16-2-16is
45 C, while the Krafft temperature for the corresponding
monomeric surfactant cetyltrimethyl ammonium bromide is
24 C [151]. While the Krafft temperature for 22-s-22 can be
as high as 80 C, it is very low (\0 C) for surfactants with
an unsaturated chain [150]. Surfactants with a long unsatu-
rated chain have an excellent ability to enhance viscosity.
Surfactants with long unsaturated chains, such as hydrox-yethyl methyl ammonium chloride (EHAC), show strong
viscoelastic properties. The viscoelastic solution made from
EHAC is referred to as a clean fracturing fluid which can be
used in EOR applications [152,153].
The properties of the spacer group are the most impor-
tant internal parameter controlling the rheological behavior
of gemini surfactants. Gemini surfactants with relatively
short spacer groups have a significantly high viscosity [54,
154, 155]. Gemini surfactants with very short spacer
groups, have a very small head area consisting of the two
head groups, and therefore, are more suitable for forming
worm-like micelles [45, 156158]. In the case of surfac-tants with longer spacer groups, the packing parameter,
which facilitates the formation of spherical micelles, will
be small and thus the viscosity will be low. Danino et al.
reported micelle formation behavior of12-s-12quaternary
ammonium gemini surfactants for a range ofs values [45].
If s is between 6 and 12, the distance between the head
groups is similar due to the space occupied by the head
groups, and similar aggregates (spherical) as in the case of
the corresponding monomeric surfactant are formed.
However, if s[14 the spacer adopts a looped structure
similar to a gemini (dimeric) surfactant [48]. If s B5, the
head groups are in close proximity to each other, leading to
aggregates with a lower curvature. The rigidity of the
spacer is also important in determining the viscoelastic
behavior. A rigid spacer like azobenzene restrains the two
alkyl tails from drawing close to each other, and hence
increases the packing parameter. However, 22-4-22and18-
3-18are more efficient in enhancing viscosity compared to
22-3-22 and 18-2-18 [83].
Gemini surfactants possess the useful property of the
ability to change the shear rate. They can be shear-thinning
230 J Surfact Deterg (2016) 19:223236
1 3
-
7/25/2019 Gemini review.pdf
9/14
or shear-thickening depending on the concentration, tem-
perature, and the applied shear rate. Shear-thinning occurs
when the rate of deformation of the network is higher and
the time required to regain equilibrium is long [49].
Near the Krafft temperature of a surfactant, a network or
worm-like micelles form. However, if the temperature is far
below or far above the Krafft point, worm-like micelles will
transform to spherical micelles. Therefore, near the Krafftpoint the viscosity of a surfactant will be a maximum, which
decreases if thetemperature is above or belowthe Krafftpoint.
This phenomenon is not common in most surfactants [84].
Guo et al. investigated the interactions between gemini sur-
factants and polymers (partially hydrolyzed polyacrylamide)
[159]. Combination of anionic gemini surfactants and non-
ionic conventional surfactants can widen the surfactant con-
centration window with increased viscosity. The investi-
gated gemini surfactant and the polymer has a synergistic
effect on theIFT reduction. TheIFT of the surfactant-polymer
solution is lower compared to the IFT of the pure surfactant.
Similar results were reported by Tang et al. [93].In general, gemini surfactants have unique rheological
properties, which are useful for EOR applications. These
rheological properties are associated with interesting
aggregation behavior. High viscosity in combination with
ultra-low interfacial tension can make gemini surfactants
ideal candidates for EOR applications.
Field Applications and Future Prospects
Chemicals must be evaluated using a series of evaluation
methods prior to their use any in field applications. Otherthan good rheological and interfacial properties, a
surfactant must be tolerant to harsh reservoir conditions,
must be thermally stable, and should have lower retention
on rock surfaces. Due to the high charge density and closer
packing of molecules, their tendency to adsorb on nega-
tively charged rock surfaces is very low [160]. In addition,
gemini surfactants have high tolerance to divalent cations,
which make them ideal candidates for EOR applications.
Only few reports are available on oil recovery experimentsusing gemini surfactants. Up to 39 % of oil recovery has
been reported from core flooding experiments by the
injection of gemini surfactants [35]. Salehi et al. compared
gemini surfactants with conventional surfactants and
observed that oil recovery from gemini surfactants is
almost doubled that from conventional surfactants [101],
which is due to better packing leading to stronger inter-
actions of the surfactant with adsorbed molecules. Labo-
ratory core flooding data of a range of gemini surfactants is
given in Table5. In summary, a large research effort is
underway on the laboratory scale and high recovery rates
have been reported using gemini surfactants. However, todate gemini surfactants have not been used in field appli-
cations. Nevertheless, considering the number of publica-
tions and the extent of the laboratory scale evaluation
concerning gemini surfactants, they will be future candi-
dates for EOR applications.
Concluding Remarks
Adsorption, rheology, wettability alteration, and interfacial
properties of gemini surfactants are reviewed together with
their potential applications in EOR. A rich variety ofanionic, non-ionic, cationic, and zwitterionic gemini
Table 5 Oil recovery data for gemini surfactants
Gemini surfactant Class Ta (C) Recovery (%) Rock b References
Ethanediyl-a,b bis(cetyldimethylammonium bromide) Cationic Ng 68 Ng [102]
Quaternary ammonium based Cationic Ng 14.96 Ng [59]
Ethylene-bis(dodecyl benzene sulfonate) Anionic 40 16.78 S [167]
2,2-Bis(4-decaaldoxy-3-sodium sulfophenylate) propane Anionic 55 19.1 Ng [94]
AN12-4-12 Anionic Ng 10.4 S [93]
C74
H154
O28
N2P2
Zwitterionic 80 39.6 S [35]
C34H74O8N2P2 Zwitterionic 80 36.7 S [35]
DMES-14 Anionic 65 42.4 (SP)c S [168]
GA124-12 Anionic Ng 11.7 S [169]
Fatty acid disulfonate Anionic 65 32 (SP) S [170]
Xylene di-C14/C16-sulfonate Anionic 90 49 Td S [101]
aTexperimental temperature
bS is for sandstone formation and Ng if information is not provided
c The surfactant is used with some polymer in injection slugd Recovery reported with letter T is total oil recovery while other values are addition oil recovery
J Surfact Deterg (2016) 19:223236 231
1 3
-
7/25/2019 Gemini review.pdf
10/14
surfactants are available. Low CMC, better wetting prop-
erties, good foaming properties, ability to reduce surface
tension, unique aggregation behavior, ability to achieve
ultra-low interfacial tension at low concentration make
them ideal candidates for EOR applications. Despite the
fact that the number of laboratory evaluations on gemini
surfactants have increased and encouraging results have
been obtained, no field data on flooding with gemini sur-factants are available. Most likely, this is due to fact that
gemini surfactants are a comparatively new class of sur-
factants and in the future they will definitely replace con-
ventional monomer surfactants, particularly if the
economics of these surfactants improve.
Acknowledgments This project was funded by the National Planfor Science, Technology, and Innovation (MAARIFAH)KingAbdulaziz City for Science and Technologythrough the Scienceand Technology Unit at King Fahd University of Petroleum & Min-erals (KFUPM)the Kingdom of Saudi Arabia, award number13-ENV1968-04. I would like to thank the Center for Integrative
Petroleum Research at the King Fahd University of Petroleum andMinerals for providing facilities to access various literature sources.
References
1. Taber J (1969) Dynamic and static forces required to remove adiscontinuous oil phase from porous media containing both oiland water. Soc Petrol Eng J 9(01):312
2. Foster W (1973) A low-tension waterflooding process. J PetTech 25(2):205210
3. Ahmadi MA, Arabsahebi Y, Shadizadeh SR, Behbahani SS(2014) Preliminary evaluation of mulberry leaf-derived surfac-tant on interfacial tension in an oil-aqueous system: EOR
application. Fuel 117:7497554. Kang W, Liu S, Meng LW, Cao D, Fan H (2010) A novel ultra-low interfacial tension foam flooding agent to enhance heavy oilrecovery. In: SPE Improved Oil Recovery Symposium, Okla-homa. USA. doi:10.2118/129175-MS
5. Zhang G, Yu J, Du C, Lee R (2015) Formulation of surfactantsfor very low/high salinity surfactant flooding without alkali. In:SPE International Symposium on Oilfield Chemistry, TheWoodlands, Texas, USA. doi: 10.2118/173738-MS
6. Kamal MS, Sultan AS, Hussein IA (2015) Screening ofamphoteric and anionic surfactants for cEOR applications usinga novel approach. Colloid Surface A 476:1723
7. Chen P, Mohanty KK (2015) Surfactant-enhanced oil recoveryfrom fractured oil-wet carbonates: effects of low ift and wetta-bility alteration. In: SPE International Symposium on Oilfield
Chemistry, The Woodlands, Texas, USA. doi:10.2118/173797-MS8. Wu X, Han M, Zahrani BH, Guo L (2015) Effect of surfactant-
polymer interaction on the interfacial properties for chemicalEOR. SPE Middle East Oil & Gas Show and Conference,811 March, Manama, Bahrain. doi:10.2118/172706-MS
9. Cao R, Yang H, Sun W, Ma YZ (2015) A new laboratory studyon alternate injection of high strength foam and ultra-lowinterfacial tension foam to enhance oil recovery. J Petrol SciEng 125:7589
10. Yuan FQ, Cheng YQ, Wang HY, Xu ZC, Zhang L, Zhang L,Zhao S (2015) Effect of organic alkali on interfacial tensions of
surfactant solutions against crude oils. Colloid Surface A470:171178
11. Liyanage PJ, Lu J, Arachchilage GWP, Weerasooriya UP, PopeGA (2015) A novel class of large-hydrophobe tristyrylphenol(TSP) alkoxy sulfate surfactants for chemical enhanced oilrecovery. J Petrol Sci Eng 128:7385
12. Ahmadi MA, Galedarzadeh M, Shadizadeh SR (2015) Wetta-bility alteration in carbonate rocks by implementing new derivednatural surfactant: enhanced oil recovery applications. TransportPorous Med 106(3):645667
13. Aoudia M, Al-Maamari RS, Nabipour M, Al-Bemani AS,Ayatollahi S (2010) Laboratory study of alkyl ether sulfonatesfor improved oil recovery in high-salinity carbonate reservoirs: acase study. Energ Fuel 24(6):36553660
14. Aoudia M, Al-Shibli MN, Al-Kasimi LH, Al-Maamari R, Al-Bemani A (2006) Novel surfactants for ultralow interfacialtension in a wide range of surfactant concentration and tem-perature. J Surfactant Deterg 9(3):287293
15. Ahmadi MA, Arabsahebi Y, Shadizadeh SR, ShokrollahzadehBehbahani S (2014) Preliminary evaluation of mulberry leaf-derived surfactant on interfacial tension in an oil-aqueous sys-tem: EOR application. Fuel 117:749755
16. Ahmadi MA, Shadizadeh SR (2013) Experimental investigationof adsorption of a new nonionic surfactant on carbonate min-erals. Fuel 104:462467
17. Gao B, Sharma MM (2013) A new family of anionic surfactantsfor enhanced-oil-recovery applications. Soc Petrol Eng J18(05):829840
18. Levitt D, Jackson A, Heinson C, Britton L, Malik T, Dwar-akanath V, Pope G (2006) Identification and evaluation of high-performance EOR surfactants. In: SPE/DOE Symposium onImproved Oil Recovery, USA, 2006. doi:10.2118/100089-MS
19. Zhao P, Jackson A, Britton C, Kim D, Britton L, Levitt D, PopeG (2008) Development of high-performance surfactants fordifficult oils. In: SPE Symposium on Improved Oil Recovery,2023 April, Tulsa, Oklahoma, USA. doi:10.2118/113432-MS
20. Zhang J, Nguyen QP, Flaaten A, Pope GA (2009) Mechanismsof enhanced natural imbibition with novel chemicals. SPEReserv Eval Eng 12(06):912920
21. Flaaten A, Nguyen QP, Pope GA, Zhang J (2009) A systematiclaboratory approach to low-cost, high-performance chemicalflooding. SPE Reserv Eval Eng 12(05):713723
22. Chen H, Han L, Luo P, Ye Z (2004) The interfacial tensionbetween oil and gemini surfactant solution. Surf Sci552(1):L53L57
23. Kamal MS, Hussien IA, Sultan AS, Han M (2013) Rheologicalstudy on ATBS-AM copolymer-surfactant system in high-tem-perature and high-salinity environment. J Chem. doi:10.1155/2013/801570
24. Kamal MS, Sultan AS, Al-Mubaiyedh UA, Hussien IA, PabonM (2014) Evaluation of rheological and thermal properties of anew fluorocarbon surfactant-polymer system for EOR applica-tions in high-temperature and high-salinity oil reservoirs. J Sur-
factant Deterg 17(5):98599325. Azad MS, Sultan AS (2014) Extending the applicability ofchemical EOR in high salinity, high temperature & frac-tured carbonate reservoir through viscoelastic surfactants. In:SPE Saudi Arabia Section Technical Symposium and Exhibi-tion, 2124 April, Al-Khobar, Saudi Arabia. doi:10.2118/172188-MS
26. Song X, Li P, Wang Y, Dong C, Thomas RK (2006) Solventeffect on the aggregate of fluorinated gemini surfactant at silicasurface. J Colloid Interf Sci 304(1):3744
27. El-Salam FHA (2009) Synthesis, antimicrobial activity andmicellization of gemini anionic surfactants in a pure state as well
232 J Surfact Deterg (2016) 19:223236
1 3
http://dx.doi.org/10.2118/129175-MShttp://dx.doi.org/10.2118/173738-MShttp://dx.doi.org/10.2118/173797-MShttp://dx.doi.org/10.2118/173797-MShttp://dx.doi.org/10.2118/172706-MShttp://dx.doi.org/10.2118/100089-MShttp://dx.doi.org/10.2118/113432-MShttp://dx.doi.org/10.1155/2013/801570http://dx.doi.org/10.1155/2013/801570http://dx.doi.org/10.2118/172188-MShttp://dx.doi.org/10.2118/172188-MShttp://dx.doi.org/10.2118/172188-MShttp://dx.doi.org/10.2118/172188-MShttp://dx.doi.org/10.1155/2013/801570http://dx.doi.org/10.1155/2013/801570http://dx.doi.org/10.2118/113432-MShttp://dx.doi.org/10.2118/100089-MShttp://dx.doi.org/10.2118/172706-MShttp://dx.doi.org/10.2118/173797-MShttp://dx.doi.org/10.2118/173797-MShttp://dx.doi.org/10.2118/173738-MShttp://dx.doi.org/10.2118/129175-MS -
7/25/2019 Gemini review.pdf
11/14
as mixed with a conventional nonionic surfactant. J SurfactantDeterg 12(4):363370
28. Mahdavian M, Tehrani-Bagha AR, Holmberg K (2011) Com-parison of a cationic gemini surfactant and the correspondingmonomeric surfactant for corrosion protection of mild steel inhydrochloric acid. J Surfactant Deterg 14(4):605613
29. Han L, Ye Z, Chen H, Luo P (2009) The interfacial tensionbetween cationic gemini surfactant solution and crude oil.J Surfactant Deterg 12(3):185190
30. El-Tabei A, Hegazy M (2013) A corrosion inhibition study of anovel synthesized gemini nonionic surfactant for carbon steel in1 M HCl solution. J Surfactant Deterg 16(5):757766
31. Ye Z, Han L, Chen H, Shi L, Luo P (2010) Effect of sodiumsalicylate on the properties of gemini surfactant solutions.J Surfactant Deterg 13(3):287292
32. Wu Z-Y, Fang Z, Qiu L-G, Wu Y, Li Z-Q, Xu T, Wang W, JiangX (2009) Synergistic inhibition between the gemini surfactantand bromide ion for steel corrosion in sulphuric acid. J ApplElectrochem 39(6):779784
33. Jiang X-M, Zhang L, Zhang W-Q, Zhao S (2015) Dilationalproperties of an anionic gemini surfactant with a hydrophobicspacer. J Surfactant Deterg 18(1):4145
34. Labena A, Hegazy MA, Horn H, Muller E (2014) Cationicgemini surfactant as a corrosion inhibitor and a biocide for highsalinity sulfidogenic bacteria originating from an oil-field watertank. J Surfactant Deterg 17(3):419431
35. Dong Z, Zheng Y, zhao J (2014) synthesis, physico-chemicalproperties and enhanced oil recovery flooding evaluation ofnovel zwitterionic gemini surfactants. J Surfactant Deterg17(6):12131222
36. Bunton CA, Robinson LB, Schaak J, Stam M (1971) Catalysis ofnucleophilic substitutions by micelles of dicationic detergents.J Org Chem 36(16):23462350
37. Menger FM, Littau C (1991) Gemini-surfactants: synthesis andproperties. J Am Chem Soc 113(4):14511452
38. Menger F, Keiper J, Azov V (2000) Gemini surfactants withacetylenic spacers. Langmuir 16(5):20622067
39. Menger FM, Keiper JS (2000) Gemini surfactants. Angew ChemInt Edit 39(11):19061920
40. Gouzy M-F, Guidetti B, Andre-Barres C, Rico-Lattes I, LattesA, Vidal C (2001) Aggregation behavior in aqueous solutions ofa new class of asymmetric bipolar amphiphiles investigated bysurface tension measurements. J Colloid Interf Sci239(2):517521
41. Menger FM, Zhang H, Caran KL, Seredyuk VA, Apkarian RP(2002) Gemini-induced columnar jointing in vitreous ice. Cryo-HRSEM as a tool for discovering new colloidal morphologies.J Am Chem Soc 124(7):11401141
42. Xi Yuan H, Rosen MJ (1988) Dynamic surface tension of aqueoussurfactant solutions. J Colloid Interf Sci 124(2):652659
43. Zana R (2002) Dimeric and oligomeric surfactants. Behavior atinterfaces and in aqueous solution: a review. Adv ColloidInterfac 97(1):205253
44. Ye Z, Zhang F, Han L, Luo P, Yang J, Chen H (2008) The effectof temperature on the interfacial tension between crude oil andgemini surfactant solution. Colloid Surface A 322(1):138141
45. Danino D, Talmon Y, Zana R (1995) Alkanediyl-. alpha.,omega.-bis(dimethylalkylammonium bromide) surfactants(dimeric surfactants). 5. Aggregation and microstructure inaqueous solutions. Langmuir 11(5):14481456
46. Kern F, Lequeux F, Zana R, Candau S (1994) Dynamic prop-erties of salt-free viscoelastic micellar solutions. Langmuir10(6):17141723
47. Geng XF, Hu XQ, Xia JJ, Jia XC (2013) Synthesis and surfaceactivities of a novel di-hydroxyl-sulfate-betaine-type zwitteri-onic gemini surfactants. Appl Surf Sci 271:284290
48. Atkin R, Craig V, Wanless E, Biggs S (2003) Adsorption of12-s-12 gemini surfactants at the silica-aqueous solution inter-face. J Phys Chem B 107(13):29782985
49. Bhadani A, Shrestha RG, Koura S, Endo T, Sakai K, Abe M,Sakai H (2014) Self-aggregation properties of new ester-basedgemini surfactants and their rheological behavior in the presenceof cosurfactantmonolaurin. Colloid Surface A 461:258266
50. Li Y, Wang X, Wang Y (2006) Comparative studies on inter-actions of bovine serum albumin with cationic gemini and sin-gle-chain surfactants. J Phys Chem B 110(16):84998505
51. Shukla D, Tyagi V (2006) Anionic gemini surfactants: a distinctclass of surfactants. J Oleo Sci 55(5):215226
52. Brinchi L, Germani R, Goracci L, Savelli G, Bunton CA (2002)Decarboxylation and dephosphorylation in new gemini surfac-tants. Changes in aggregate structures. Langmuir18(21):78217825
53. Bhattacharya S, Kumar VP (2004) Evidence of enhanced reac-tivity of DAAP nucleophiles toward dephosphorylation anddeacylation reactions in cationic Gemini micellar media. J OrgChem 69(2):559562
54. In M, Bec V, Aguerre-Chariol O, Zana R (2000) Quaternaryammonium bromide surfactant oligomers in aqueous solution:self-association and microstructure. Langmuir 16(1):141148
55. De S, Aswal VK, Goyal PS, Bhattacharya S (1996) Role ofspacer chain length in dimeric micellar organization. Smallangle neutron scattering and fluorescence studies. J Phys Chem-Us 100(28):1166411671
56. Qiu LG, Cheng MJ, Xie AJ, Shen YH (2004) Study on theviscosity of cationic gemini surfactantnonionic polymer com-plex in water. J Colloid Interf Sci 278(1):4043
57. Kumar N, Tyagi R (2014) Industrial applications of dimericsurfactants: a review. J Disper Sci Technol 35(2):205214
58. Hait S, Moulik S (2002) Gemini surfactants: a distinct class ofself-assembling molecules. Curr Sci India 82(9):11011111
59. Xiong SC, Shi L, Liu WD, Han ZL, He Y (2009) Performanceproperties of quaternary ammonium salt gemini surfactant LTSfor stimulating injection wells and enhancing oil recovery.Oilfield Chem 2:024
60. Jiang YW (2009) Preparation and oil-recovery properties ofamino-sulfonate amphoteric gemini sulfactants. Fine SpecialtyChem 21:14
61. Haibo W (2009) Oil displacement character of Gemini surfac-tant weak gel system. Petrol Geol Recovery Efficiency 2:5254
62. Tang S, Wang L, Hao M, Lai Y, Yue Q (2007) Study on surfaceactivity and displacement efficiency of gemini surfactant(C12212.2Br-1). Drill Prod Technol 30(4):127
63. Lu T, Lan Y, Liu C, Huang J, Wang Y (2012) Surface proper-ties, aggregation behavior and micellization thermodynamics ofa class of gemini surfactants with ethyl ammonium headgroups.J Colloid Interf Sci 377(1):222230
64. Cai B, Dong J, Cheng L, Jiang Z, Yang Y, Li X (2013)Adsorption and micellization of gemini surfactants with pyrro-lidinium head groups: effect of the spacer length. Soft Matter
9(31):7637764665. Dahan E, Sundararajan PR (2014) Solvent-dependent nanos-tructures of gels of a Gemini surfactant based on perylene dii-mide spacer and oligostyrene tails. Eur Polym J 61:113123
66. Yao D, Tuteja B, Sundararajan PR (2006) Pigment-mediatednanoweb morphology of poly (dimethylsiloxane)-substitutedperylene bisimides. Macromolecules 39(23):77867788
67. Ma C, Han L, Jiang Z, Huang Z, Feng J, Yao Y, Che S (2011)Growth of mesoporous silica film with vertical channels onsubstrate using gemini surfactants. Chem Mater23(16):35833586
68. Savic S, Weber C, Savic MM, Muller-Goymann C (2009)Natural surfactant-based topical vehicles for two model drugs:
J Surfact Deterg (2016) 19:223236 233
1 3
-
7/25/2019 Gemini review.pdf
12/14
influence of different lipophilic excipients on in vitro/in vivoskin performance. Int J Pharm 381(2):220230
69. Horiuchi S, Winter G (2015) CMC determination of nonionicsurfactants in protein formulations using ultrasonic resonancetechnology. Eur J Pharm Biopharm 92:814
70. Rather MA, Rather GM, Pandit SA, Bhat SA, Bhat MA (2015)Determination of cmc of imidazolium based surface active ionicliquids through probe-less UVvis spectrophotometry. Talanta131:5558
71. Jiang YS, Guan B, Lu Y, Cui W, Qiu X, RIPED-Langfang P(2013) Viscoelastic Evaluation of Gemini Surfactant Gel forHydraulic Fracturing. In: SPE European Formation DamageConference & Exhibition, 57 June, Noordwijk, Netherlands.doi:10.2118/165177-MS
72. Sheng J (2010) Modern chemical enhanced oil recovery: theoryand practice. Gulf Professional Publishing, Elsevier Inc, TheBoulevard, Oxford, UK. ISBN 978-1-85617-745-0
73. Zhu YP, Masuyama A, Okahara M (1990) Preparation andsurface active properties of amphipathic compounds with twosulfate groups and two lipophilic alkyl chains. J Am Oil ChemSoc 67(7):459463
74. Zhu YP, Masuyama A, Kobata Y, Nakatsuji Y, Okahara M,Rose MJ (1993) Double-chain surfactants with two carboxylategroups and their relation to similar double-chain compounds.J Colloid Interf Sci 158(1):4045
75. Zhu YP, Masuyama A, Nagata T, Okahara M (1991) Preparationand properties of double-chain surfactants bearing two sulfonategroups. Yukagaku 40(6):473477
76. Zhu YP, Masuyama A, Nakatsuji Y, Okahara M (1993) Syn-thesis and properties of bis(sulfonate) types of double-chainsurfactants bearing a sulfur atom in the connecting part. Yuka-gaku 42(2):8694
77. Masuyama A, Hrono T, Yun-Peng Z, Okahara M, Rosen M(1992) Synthesis and properties of bis(taurine) types of double-chain surfactants. Yukagaku 41(4):301305
78. Y-p Zhu, Masuyama A, Okahara M (1991) Preparation andsurface-active properties of new amphipathic compounds withtwo phosphate groups and two long-chain alkyl groups. J AmOil Chem Soc 68(4):268271
79. Zhu YP, Masuyama A, Kirito YI, Okahara M (1991) Preparationand properties of double-or triple-chain surfactants with twosulfonate groups derived from N-acyldiethanolamines. J Am OilChem Soc 68(7):539543
80. Zhu YP, Masuyama A, Okahara Kirito YI, Rosen MJ (1992)Preparation and properties of glycerol-based double-or triple-chain surfactants with two hydrophilic ionic groups. J Am OilChem Soc 69(7):626632
81. Kim TS, Kida T, Nakatsuji Y, Hirao T, Ikeda I (1996) Surface-active properties of novel cationic surfactants with two alkylchains and two ammonio groups. J Am Oil Chem Soc73(7):907911
82. Youyi Zhu S, Hou Q, Wang Z, Jian G, Zhang Q (2013) Can weuse some methods to design surfactants with ultralow oil/water
interfacial tension? spe international symposium on oilfieldchemistry, 810 April. The Woodlands, Texas, USA. doi:10.2118/164100-MS
83. HanL, Chen H, LuoP (2004)Viscositybehaviorof cationic geminisurfactants with long alkyl chains. Surf Sci 564(1):141148
84. Chen H, Ye Z, Han L, Luo P, Zhang L (2007) Temperature-induced micelle transition of gemini surfactant in aqueoussolution. Surf Sci 601(10):21472151
85. Boschkova K, Feiler A, Kronberg B, Stalgren J (2002)Adsorption and frictional properties of gemini surfactants atsolid surfaces. Langmuir 18(21):79307935
86. Candau S (1997) Gemini surfactants, the effect of hydrophobicchain length and dissymmetry. Chem Commun 21:21052106
87. Duivenvoorde FL, Feiters MC, Van der Gaast S, Engberts JB(1997) Synthesis and properties of di-n-dodecyl a,x-alkyl bis-phosphate surfactants. Langmuir 13(14):37373743
88. Lu T, Han F, Mao G, Lin G, Huang J, Huang X, Wang Y, Fu H(2007) Effect of hydrocarbon parts of the polar headgroup onsurfactant aggregates in gemini and bola surfactant solutions.Langmuir 23(6):29322936
89. Kirby AJ, Camilleri P, Engberts JB, Feiters MC, Nolte RJ,Soderman O, Bergsma M, Bell PC, Fielden ML, Garca Rodr-guez CL (2003) Gemini surfactants: new synthetic vectors forgene transfection. Angew Chem Int Edit 42(13):14481457
90. Sharma G, Naqvi AZ, Chaturvedi SK, Khan RH (2013) Ion-dipole induced interaction between cationic gemini/TTAB andnonionic (Tween) surfactants: interfacial and microstructuralphenomena. RSC Adv 3(19):69456959
91. Li Q, Wang X, Yue X, Chen X (2013) Wormlike micellesformed using gemini surfactants with quaternary hydroxyethylmethylammonium headgroups. Soft Matter 9(40):96679674
92. Hoque J, Gonuguntla S, Yarlagadda V, Aswal VK, Haldar J(2014) Effect of amide bonds on the self-assembly of geminisurfactants. Phys Chem Chem Phys 16(23):1127911288
93. Tang SF, Hu XD, Ouyang XN, Yan SX, Wen SC, Lai YL (2012)Experimental study of anionic gemini surfactant enhancingwaterflooding recovery ratio. Adv Mat Res 361:469472
94. Liu Y, Lu Y, Lin W, Hu X (2011) Performance study of a newtype alkaline/surfactant/polymer ternary complex. In: SPEEnhanced Oil Recovery Conference, 1921 July, Kuala Lumpur,Malaysia. doi:10.2118/145001-MS
95. Wang Y, Xu H, Yu W, Bai B, Song X, Zhang J (2011) Sur-factant induced reservoir wettability alteration: recent theoreti-cal and experimental advances in enhanced oil recovery. Pet Sci8(4):463476
96. Standnes DC, Austad T (2000) Wettability alteration in chalk: 2.Mechanism for wettability alteration from oil-wet to water-wetusing surfactants. J Petrol Sci Eng 28(3):123143
97. Zhang R, Qin N, Peng L, Tang K, Ye Z (2012) Wettabilityalteration by trimeric cationic surfactant at water-wet/oil-wetmica mineral surfaces. Appl Surf Sci 258(20):79437949
98. Salehi M, Johnson SJ, Liang J-T (2008) Mechanistic study ofwettability alteration using surfactants with applications in nat-urally fractured reservoirs. Langmuir 24(24):1409914107
99. B-f Hou, Y-f Wang, Huang Y (2015) Mechanistic study ofwettability alteration of oil-wet sandstone surface using differentsurfactants. Appl Surf Sci 330(2015):5664
100. Austad T, Matre B, Milter J, Saevareid A, yno L (1998)Chemical flooding of oil reservoirs 8 spontaneous oil expulsionfrom oil-and water-wet low permeable chalk material by imbi-bition of aqueous surfactant solutions. Colloid Surface A137(1):117129
101. Salehi M, Johnson SJ, Liang J-T (2010) Enhanced wettabilityalteration by surfactants with multiple hydrophilic moieties.J Surfactants Deterg 13(3):243246
102. Bi Z, Qi L, Liao W (2005) Dynamic surface properties, wetta-
bility and mimic oil recovery of ethanediyl-a,b-bis(cetyldimethylammonium bromide) on dodecane modifiedsilica powder. J Mater Sci 40(11):27832788
103. Ahmadi MA, Shadizadeh S (2015) Experimental and theoreticalstudy of a new plant derived surfactant adsorption on quartzsurface: kinetic and isotherm methods. J Disper Sci Technol36(3):441452
104. Ahmadi MA, ShadizadehSR (2013) Induced effect of adding nanosilica on adsorption of a natural surfactant onto sandstone rock:experimental and theoretical study. J Petrol Sci Eng 112:239247
105. Ahmadi MA, Shadizadeh SR (2013) Implementation of a high-performance surfactant for enhanced oil recovery from carbon-ate reservoirs. J Petrol Sci Eng 110:6673
234 J Surfact Deterg (2016) 19:223236
1 3
http://dx.doi.org/10.2118/165177-MShttp://dx.doi.org/10.2118/164100-MShttp://dx.doi.org/10.2118/164100-MShttp://dx.doi.org/10.2118/145001-MShttp://dx.doi.org/10.2118/145001-MShttp://dx.doi.org/10.2118/164100-MShttp://dx.doi.org/10.2118/164100-MShttp://dx.doi.org/10.2118/165177-MS -
7/25/2019 Gemini review.pdf
13/14
106. Zendehboudi S, Ahmadi MA, Rajabzadeh AR, Mahinpey N,Chatzis I (2013) Experimental study on adsorption of a newsurfactant onto carbonate reservoir samplesapplication toEOR. Can J Chem Eng 91(8):14391449
107. Ahmadi MA, Shadizadeh SR (2012) Adsorption of novel non-ionic surfactant and particles mixture in carbonates: enhancedoil recovery implication. Energ Fuel 26(8):46554663
108. Ahmadi MA, Zendehboudi S, Shafiei A, James L (2012) Non-ionic surfactant for enhanced oil recovery from carbonates:adsorption kinetics and equilibrium. Ind Eng Chem Res51(29):98949905
109. Cao M, Song X, Wang J, Wang Y (2006) Adsorption of hexyl-a,x-bis(dodecyldimethylammonium bromide) gemini surfactanton silica and its effect on wettability. J Colloid Interf Sci300(2):519525
110. Behrens EJ (2013) Investigation of loss of surfactants duringenhanced oil recovery applications-adsorption of surfactantsonto clay materials. Institutt for Kjemisk Prosessteknologi.http://hdl.handle.net/11250/247912
111. Porter MR (1991) Recent developments in the analysis of sur-factants. Springer, Dordrecht, Netherlands. ISBN978-1851665815
112. Schmitt TM (2001) Analysis of surfactants. Marcel Dekker,New York. ISBN 0-8247-0449-5
113. Daoshan L, Shouliang L, Yi L, Demin W (2004) The effect ofbiosurfactant on the interfacial tension and adsorption loss ofsurfactant in ASP flooding. Colloid Surface A 244(1):5360
114. Cullum D (1994) Introduction to surfactant analysis. Springer,Dordrecht, Netherlands. ISBN 978-94-011-1316-8
115. Rosen MJ, Goldsmith HA (1960) Systematic analysis of surface-active agents. Interscience Publishers, New York
116. Park S, Lee ES, Sulaiman WRW (2014) Adsorption behaviors ofsurfactants for chemical flooding in enhanced oil recovery. J IndEng Chem 21:12391245
117. ShamsiJazeyi H, Verduzco R, Hirasaki GJ (2014) Reducingadsorption of anionic surfactant for enhanced oil recovery: partI. Competitive adsorption mechanism. Colloid Surface A453:162167
118. Gao B, Sharma MM (2012) A new family of anionic surfactantsfor EOR applications. In: SPE Annual Technical Conferenceand Exhibition, 810 October, San Antonio, Texas, USA.doi:10.2118/159700-MS
119. Han M, Al Sofi A, Fuseni A, Zhou X, Hassan S (2013) Devel-opment of chemical EOR formulations for a high temperatureand high salinity carbonate reservoir. In: International PetroleumTechnology Conference, 2628 March, Beijing, China. doi:10.2523/17084-MS
120. Pahi AB, Kiraly Z, Mastalir A, Dudas J, Puskas S, Vago A(2008) Thermodynamics of micelle formation of the counterioncoupled gemini surfactant bis(4-(2-dodecyl) benzenesulfonate)-Jeffamine salt and its dynamic adsorption on sandstone. J PhysChem B 112(48):1532015326
121. Rosen M, Li F (2001) The adsorption of gemini and conven-
tional surfactants onto some soil solids and the removal of2-naphthol by the soil surfaces. J Colloid Interf Sci234(2):418424
122. Wei M, Saleh L, Bai B (2014) Data analysis and novel screeningcriteria for polymer flooding based on a comprehensive data-base. In: SPE Improved Oil Recovery Symposium, 1216 April,Tulsa, Oklahoma, USA. doi: 10.2118/169093-MS
123. Van Wunnik JN, Stoll M, Al-sulaimani HS, Arkesteijn F, FaberR (2014) Potential of alkaline surfactant polymer (ASP) floodingin a medium-light oil reservoir with strong bottom aquifer. In:SPE EOR Conference at Oil and Gas West Asia, 31 March-2April, Muscat, Oman. doi:10.2118/169669-MS
124. Samanta A, Ojha K, Sarkar A, Mandal A (2011) Surfactant andsurfactant-polymer flooding for enhanced oil recovery. AdvPetrol Explor Dev 2(1):1318
125. Samanta A, Bera A, Ojha K, Mandal A (2010) Effects of alkali,salts, and surfactant on rheological behavior of partiallyhydrolyzed polyacrylamide solutions. J Chem Eng Data55(10):43154322
126. Jang HY, Zhang K, Chon BH, Choi HJ (2014) Enhanced oilrecovery performance and viscosity characteristics of polysac-charide xanthan gum solution. J Ind Eng Chem21(2015):741745
127. Jung JC, Zhang K, Chon BH, Choi HJ (2013) Rheology andpolymer flooding characteristics of partially hydrolyzed poly-acrylamide for enhanced heavy oil recovery. J Appl Polym Sci127(6):48334839
128. Chen Q, Wang Y, Lu Z, Feng Y (2013) Thermoviscosifyingpolymer used for enhanced oil recovery: rheological behaviorsand core flooding test. Polym Bull 70(2):391401
129. Zhang P, Wang Y, Yang Y, Chen W, Baie S (2013) Effectiveviscosity in porous media and applicable limitations for polymerflooding of an associative polymer. Technol Rev, Oil Gas Sci.doi:10.2516/ogst/2013149
130. Kamal MS, Sultan AS, Al-Mubaiyedh UA, Hussein IA (2015)Review on polymer flooding: rheology, adsorption, stability, andfield applications of various polymer systems. Polym Rev55(3):491530
131. Kamal MS, Sultan AS, Al-Mubaiyedh UA, Hussein IA, Feng Y(2015) Rheological properties of thermoviscosifying polymersin high-temperature and high-salinity environments. Can JChem Eng 93(7):11941200
132. Urbissinova T, Trivedi JJ, Kuru E (2010) Effect of elasticityduring viscoelastic polymer flooding a possible mechanism ofincreasing the sweep efficiency. In: SPE Western RegionalMeeting, 2729 May, Anaheim, California, USA. doi:10.2118/133471-MS
133. Wang D, Xia H, Liu Z, Yang Q (2001) Study of the mechanismof polymer solution with visco-elastic behavior increasingmicroscopic oil displacement efficiency and the forming ofsteady oil thread flow channels. In: SPE Asia Pacific Oil and GasConference and Exhibition, 1719 April, Jakarta, Indonesia. doi:10.2118/68723-MS
134. Xia H, Wang D, Wu J, Kong F (2004) Elasticity of HPAMsolutions increases displacement efficiency under mixed wetta-bility conditions. In: SPE Asia Pacific Oil and Gas Conferenceand Exhibition, Australia, doi:10.2118/88456-MS
135. Xia H, Wang D, Wu W, (2007) Jiang H Effect of the visco-elasticity of displacing fluids on the relationship of capillarynumber and displacement efficiency in weak oil-wet cores. In:Asia Pacific Oil and Gas Conference and Exhibition, Indonesia,doi:10.2118/109228-MS
136. Zhang Z, Li J, Zhou J (2011) Microscopic roles of viscoelas-ticity in HPMA polymer flooding for EOR. Transport PorousMed 86(1):199214
137. Wang D, Cheng J, Xia H, Li Q, Shi J (2001) Viscous-elasticfluids can mobilize oil remaining after water-flood by forceparallel to the oil-water interface. In: SPE Asia Pacific ImprovedOil Recovery Conference, 69 October, Kuala Lumpur,Malaysia. doi:10.2118/72123-MS
138. Rogers SA, Calabrese MA, Wagner NJ (2014) Rheology ofbranched wormlike micelles. Curr Opin Colloid In19(6):530535
139. Pei X, Xu Z, Song B, Cui Z, Zhao J (2014) Wormlike micellesformed in catanionic systems dominated by cationic geminisurfactant: synergistic effect with high efficiency. Colloid Sur-face 443:508514
J Surfact Deterg (2016) 19:223236 235
1 3
http://hdl.handle.net/11250/247912http://dx.doi.org/10.2118/159700-MShttp://dx.doi.org/10.2523/17084-MShttp://dx.doi.org/10.2523/17084-MShttp://dx.doi.org/10.2118/169093-MShttp://dx.doi.org/10.2118/169669-MShttp://dx.doi.org/10.2516/ogst/2013149http://dx.doi.org/10.2118/133471-MShttp://dx.doi.org/10.2118/133471-MShttp://dx.doi.org/10.2118/68723-MShttp://dx.doi.org/10.2118/88456-MShttp://dx.doi.org/10.2118/109228-MShttp://dx.doi.org/10.2118/72123-MShttp://dx.doi.org/10.2118/72123-MShttp://dx.doi.org/10.2118/109228-MShttp://dx.doi.org/10.2118/88456-MShttp://dx.doi.org/10.2118/68723-MShttp://dx.doi.org/10.2118/133471-MShttp://dx.doi.org/10.2118/133471-MShttp://dx.doi.org/10.2516/ogst/2013149http://dx.doi.org/10.2118/169669-MShttp://dx.doi.org/10.2118/169093-MShttp://dx.doi.org/10.2523/17084-MShttp://dx.doi.org/10.2523/17084-MShttp://dx.doi.org/10.2118/159700-MShttp://hdl.handle.net/11250/247912 -
7/25/2019 Gemini review.pdf
14/14
140. Lin Z, Scriven L, Davis H (1992) Cryogenic electron micro-scopy of rodlike or wormlike micelles in aqueous solutions ofnonionic surfactant hexaethylene glycol monohexadecyl ether.Langmuir 8(9):22002205
141. Vinson PK, Talmon Y (1989) Comments on electron diffrac-tion observed in the gigantic micelle-producing system ofCTAB-aromatic additives, by Hirata, Sakaiguchi, and Akai.J Colloid Interf Sci 133(1):288289
142. Jerke G, Pedersen JS, Egelhaaf SU, Schurtenberger P (1998)Flexibility of charged and uncharged polymer-like micelles.Langmuir 14(21):60136024
143. Yang J (2002) Viscoelastic wormlike micelles and their appli-cations. Curr Opin Colloid In 7(5):276281
144. Porte G, Appell J (1981) Growth and size distributions ofcetylpyridinium bromide micelles in high ionic strength aqueoussolutions. J Phys Chem 85(17):25112519
145. Kalus J, Hoffmann H, Reizlein K, Ulbricht W, Ibel K (1982)Small angle neutron scattering measurements on ionic detergentsolutions with rodlike micelles. Berich Bunsen Gesel86(1):3742
146. Zana R, Talmon Y (1993) Dependence of aggregate morphologyon structure of dimeric surfactants. Nature 362(6417):228230
147. Candau S, Hirsch E, Zana R (1984) New aspects of the beha-viour of alkyltrimethylammonium bromide micelles: light scat-tering and viscosimetric studies. J Phys-Paris 45(7):12631270
148. Aswal V, De S, Goyal P, Bhattacharya S, Heenan R (1998)Small-angle neutron scattering study of micellar structures ofdimeric surfactants. Phys Rev E 57(1):776
149. Aswal V, Goyal P, Heenan R (1998) Transition from disc to rod-like shape of 16-3-16 dimeric micelles in aqueous solutions.J Chem Soc Faraday T 94(19):29652967
150. Li H, Yang H, Yan Y, Wang Q, He P (2010) Synthesis andsolution properties of cationic gemini surfactants with longunsaturated tails. Surf Sci 604(13):11731178
151. Zhao J, Christian SD, Fung B (1998) Mixtures of monomericand dimeric cationic surfactants. J Phys Chem B102(39):76137618
152. Raghavan SR, Kaler EW (2001) Highly viscoelastic wormlikemicellar solutions formed by cationic surfactants with longunsaturated tails. Langmuir 17(2):300306
153. Qu Q, Nelson EB, Willberg DM, Samuel MM, Lee Jr JC, ChangFF, Card RJ, Vinod PS, Brown JE, Thomas RL (2002) Com-positions containing aqueous viscosifying surfactants andmethods for applying such compositions in subterranean for-mations. US Patent 20030019627 A1
154. Oda R, Huc I, Homo J-C, Heinrich B, Schmutz M, Candau S(1999) Elongated aggregates formed by cationic gemini sur-factants. Langmuir 15(7):23842390
155. Sharma SC, Shrestha RG, Varade D, Aramaki K (2007) Rheo-logical behavior of gemini-type surfactant/alkanolamide/watersystems. Colloid Surface A 305(1):8388
156. Song B, Hu Y, Song Y, Zhao J (2010) Alkyl chain length-dependent viscoelastic properties in aqueous wormlike micellar
solutions of anionic gemini surfactants with an azobenzenespacer. J Colloid Interf Sci 341(1):94100157. Lu T, Huang J (2007) Synthesis and properties of novel gemini
surfactant with short spacer. Chinese Sci Bull 52(19):26182620158. Bernheim-Groswasser A, Zana R, Talmon Y (2000) Sphere-to-
cylinder transition in aqueous micellar solution of a dimeric(gemini) surfactant. J Phys Chem B 104(17):40054009
159. Guo YJ, Liu JX, Zhang XM, Feng RS, Li HB, Zhang J, Lv X,Luo PY (2012) Solution property investigation of combinationflooding systems consisting of gemininon-ionic mixed surfac-tant and hydrophobically associating polyacrylamide forenhanced oil recovery. Energ Fuel 26(4):21162123
160. Berger P, Lee C (2002) Ultra-low concentration surfactants forsandstone and limestone floods. In: SPE/DOE Improved OilRecovery Symposium, 1317 April, Tulsa, Oklahoma. doi: 10.2118/75186-MS
161. Menger F, Littau C (1993) Gemini surfactants: a new class ofself-assembling molecules. J Am Chem Soc115(22):1008310090
162. Acharya DP, Gutierrez JM, Aramaki K, K-i Aratani, Kunieda H(2005) Interfacial properties and foam stability effect of novelgemini-type surfactants in aqueous solutions. J Colloid Interf Sci291(1):236243
163. Qiuling Z, Zhinong G (2006) Synthesis and surface-activeproperty of bis-quaternary ammonium-sodium sulfate geminisurfactant. Front Chem China 1(4):434437
164. Liu S, Sang R, Hong S, Cai Y, Wang H (2013) A novel type ofhighly effective nonionic gemini alkyl o-glucoside surfactants: aversatile strategy of design. Langmuir 29(27):85118516
165. Islam MR, Dahan E, Saimani S, Sundararajan PR (2012)Preclusion of nano scale self-assembly in block-selective non-aqueous solvents for rodcoil and coilrodcoil macromolecularsurfactants based on perylene tetracarboxylic diimide. EurPolym J 48(9):15381554
166. Barran-Berdon AL, Misra SK, Datta S, Munoz-Ubeda M,Kondaiah P, Junquera E, Bhattacharya S, Aicart E (2014)Cationic gemini lipids containing polyoxyethylene spacers asimproved transfecting agents of plasmid DNA in cancer cells.J Mater Chem 2(29):46404652
167. Wang Y, Zheng XY, LI XG, Jiang QZ, Wu YQ (2009) Effectsof ethylene-bis(alkyl benzene sulfonate) gemini surfactant onwettability of solid surfaces. Oilfield chemistry 3:021. http://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX200903021.htm
168. Jian-xin L, Yong-jun G, Jun H, Jian Z, Xing L, Xin-ming Z,Xin-sheng X, Ping-ya L (2012) Displacement characters ofcombination flooding systems consisting of gemini-nonionicmixed surfactant and hydrophobically associating polyacry-lamide for Bohai offshore oilfield. Energ Fuel 26(5):28582864
169. Hu XD, Tang SF, Liu Y, Wen SC, Yan SX (2012) Performanceof anionic gemini surfactant in enhancement of oil recovery.oilfield chemistry 1:013. http://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX201201013.htm
170. Zhang XM, Guo YJ, Liu JX, Zhu YW, Hu J, Feng RS, Fu CY(2014) Adaptability of a hydrophobically associating polyacry-lamide/mixed-surfactant combination flooding system to theShengli Chengdao oilfield. J Appl Polym Sci 131(12):40390.doi:10.1002/app.40390
Muhammad Shahzad KamalReceived his B.Sc. (2008) in chemicalengineering and M.Sc. (2010) in polymer engineering from UETLahore. He completed his Ph.D. in chemical engineering at the King
Fahd University of Petroleum and Minerals (KFUPM), Saudi Arabia.Currently he is working as a research engineer in the Center forIntegrative Petroleum Research at KFUPM.
236 J Surfact Deterg (2016) 19:223236
1 3
http://dx.doi.org/10.2118/75186-MShttp://dx.doi.org/10.2118/75186-MShttp://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX200903021.htmhttp://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX200903021.htmhttp://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX201201013.htmhttp://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX201201013.htmhttp://dx.doi.org/10.1002/app.40390http://dx.doi.org/10.1002/app.40390http://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX201201013.htmhttp://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX201201013.htmhttp://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX200903021.htmhttp://en.cnki.com.cn/Article_en/CJFDTOTAL-YJHX200903021.htmhttp://dx.doi.org/10.2118/75186-MShttp://dx.doi.org/10.2118/75186-MS