Synthesis and evaluation of properties of: N, N -bis(perfluorooctyl)imine acetate sodium as a gas-wetting alteration agent

Article abstract of DOI:10.1039/c7ra10742k

The wettability of a rock's surface is a vital factor for gas flow and fracturing fluid backflow. As a result of this, novel and effective gas wetting alteration agents are required. In this work, a gas-wetting alteration agent, N,N-bis(perfluorooctyl)imine acetate sodium, was synthesized and characterized by different methods. The wettability of a rock's surface was evaluated by contact angle and imbibition measurements, the Owens two-liquid method and glass capillary tube rise testing. The results showed that after treatment with 0.5 wt% N,N-bis(perfluorooctyl)imine acetate sodium the contact angles of water and n-hexadecane on the surface of the rock increased from 36° and 0° to 140° and 119°, respectively. The surface free energy rapidly reduced from primeval 72 mN m^-1 to 3.4 mN m^-1 after treatment with 0.3 wt% N,N-bis(perfluorooctyl)imine acetate sodium. These values agreed with the imbibition measurements and the results of the glass capillary tube rise testing. Moreover, analysis by scanning electron microscopy (SEM) and energy dispersive spectroscopy (EDS) showed that the roughness of the rock surface significantly increased. The above results fully proved that the wettability of the rock surface is altered from its original water-wetting or oil-wetting to gas-wetting. Furthermore, thermal analysis demonstrated that the gas-wetting alteration agent has good thermal stability, which indicates its great potential to be used as a gas-wetting alteration agent for unconventional gas reservoirs under high temperature conditions.

Full text of DOI:10.1039/c7ra10742k

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PAPER
Synthesis and evaluation of properties of N,N-
bis(perfluorooctyl)imine acetate sodium as a gas-
wetting alteration agent
Cite this: RSC Adv., 2018, 8, 7924
a
a
b
a
a
a
Yanling Wang,* Yongfei Li,
Qian Wang, Qiang Li, Yue Zhang and Lin Yuan
The wettability of a rock’s surface is a vital factor for gas flow and fracturing fluid backflow. As a result of this,
novel and effective gas wetting alteration agents are required. In this work, a gas-wetting alteration agent,
N,N-bis(perfluorooctyl)imine acetate sodium, was synthesized and characterized by different methods. The
wettability of a rock’s surface was evaluated by contact angle and imbibition measurements, the Owens
two-liquid method and glass capillary tube rise testing. The results showed that after treatment with
0.5 wt% N,N-bis(perfluorooctyl)imine acetate sodium the contact angles of water and n-hexadecane on
ꢀ
ꢀ
ꢀ
ꢀ
the surface of the rock increased from 36 and 0 to 140 and 119 , respectively. The surface free energy
ꢁ1
ꢁ1
rapidly reduced from primeval 72 mN m
to 3.4 mN m after treatment with 0.3 wt% N,N-
bis(perfluorooctyl)imine acetate sodium. These values agreed with the imbibition measurements and the
results of the glass capillary tube rise testing. Moreover, analysis by scanning electron microscopy (SEM)
and energy dispersive spectroscopy (EDS) showed that the roughness of the rock surface significantly
increased. The above results fully proved that the wettability of the rock surface is altered from its
original water-wetting or oil-wetting to gas-wetting. Furthermore, thermal analysis demonstrated that
the gas-wetting alteration agent has good thermal stability, which indicates its great potential to be used
as a gas-wetting alteration agent for unconventional gas reservoirs under high temperature conditions.
Received 28th September 2017
Accepted 31st January 2018
DOI: 10.1039/c7ra10742k
rsc.li/rsc-advances
Reservoir wettability is a crucial factor that dominates the
distribution and ow of gas in shale media. It also has
1
. Introduction
With the change in energy patterns, shale gas has recently a remarkable inuence on both the re-ow of fracturing uid
5,6
emerged as a relatively important energy source that provides and the relative permeability of the reservoir. Thus, the
an opportunity for a lot of countries around the world to reduce investigation of reservoir wettability is of profound signicance
7
their dependence on energy imports and their struggle to ach- for improving shale gas recovery. Li et al. put forward the gas-
1
ieve energy independence. It may also be a potential transition wetting concept in which the wettability of rock was altered
fuel that will permit the transformation from non-renewable to from liquid-wetting to neutral using a uorocarbon surfactant.
8
renewable energy resources as it is conducive to reducing Tang and Firoozabadi demonstrated the altering of the wetta-
2
emissions of carbon dioxide and other pollutants. However, bility of sandstone from strong liquid-wetting to neutral gas-
9
shale gas is generally extracted from low-permeability or tight wetting using polymers. Feng et al. achieved the gas wetting
porous media. It cannot be captured from original source rock alteration of a rock’s surface with organosilicon-acrylic and
3
10
without an extra driving force. Hydraulic fracturing is the signicantly improved gas production. Jin and Wang investi-
technology classically used to increase the production of shale gated the concept that the wettability of low-permeability rock
4
gas, but this method is characterized by large displacement of could be permanently altered from strong water-wetting to
liquid volume. Thus, fracturing uid owback plays a very intermediate by a novel gas-wetting alteration agent. Further-
11
important role in hydraulic fracturing operations. Its purpose is more, Al-Yaseri et al. veried that the density of gas in the gas–
to promote the outow of extra liquid which maintains the liquid–solid system has a signicant effect on the wettability.
12,13
crevice with strong gas ow and to reduce damage to the Iglauer et al.
reported that gas-wetting increases with
formation.
increasing pressure, salinity and dissolved ion valencies, while
the effect of temperature is not well understood. Moreover, the
inuence of various subsurface minerals and rock types on the
wettability and the mechanism of interaction were also
investigated.
a
College of Petroleum Engineering, China University of Petroleum (East China),
Qingdao 266580, Shandong, P. R. China. E-mail: wangyl@upc.edu.cn
b
However, the hydrophobic and oleophobic groups of the gas-
wetting alternation agents used in the previous studies were
College of Chemical Engineering, China University of Petroleum (East China),
Qingdao 266580, Shandong, P. R. China
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single-chain structures that cannot effectively alter the wetta- puried by recrystallization aer removing the solvent. The
bility of rock surfaces from liquid-wetting to gas-wetting. The puried material was steamed under reduced pressure to give
objective of this study is to synthesize a gas-wetting alteration the nal product N,N-bis(peruorooctyl)imine acetate sodium.
agent with a double-chain hydrophobic and oleophobic struc- This reaction is shown in Scheme 1(c).
ture. The product can more effectively alter the reservoir
wettability and improve the owback rate of the fracturing uid.
2.3 Characterization
An FT-IR spectrum of the sample was obtained using a Bruker
VERTEX 70 series Fourier transform infrared spectrometer in
the wavenumber range of 4000–500 cm ; H NMR spectra were
2
. Experimental
2.1 Materials
ꢁ1
1
Peruorooctanoyl chloride was provided by Aladdin Industrial recorded in the stated solutions, on a Bruker DRX-400 spec-
Corporation. Triethylamine was offered by Shandong Chemical trometer, operating at 400 MHz for H; the thermal stability of
Reagents Co., Ltd. Dichloromethane and sodium chloroacetate the compound was analyzed using a TGA/SDTA851 thermal
ꢀ
ꢁ1
were supplied by Sinopharm Chemical Reagent Co. Ltd. Anhy- gravimetric analyzer with a heating rate of 10 C min . The
drous ethanol and acetone were purchased from Shanghai Han morphology and elements of the rock surface before and aer
Guang Chemical Reagent Co., Ltd. All of the above chemicals treatment were examined by a JEOL JSM-6390A scanning elec-
are analytical reagents. The rock samples used in this study tron microscope and energy dispersive spectrometer (EDAX
were obtained from the Shengli Oileld, China, and the basic Ltd., USA).
parameters are shown in Table 1. During the experiment, the
rock samples were polished using sandpaper to get a relatively
2
.4 Methods
smooth surface, then washed with 1.0 wt% NaCl solution and
ꢀ
14
dried at 80 C for 12 h. Deionized water was prepared in the
laboratory.
2.4.1 Contact angle measurement. In order to measure the
contact angle of water or n-hexadecane drops on original and
treated rock surfaces, we used a micropipette to place a liquid
drop on the surface of air-saturated rock at room temperature.
The morphology of a sessile droplet on the rock surface was
enlarged on a monitor screen. Pictures of the droplets were
taken using a digital camera under proper illumination of
a light source. The contact angle of the gas–liquid–rock three-
phase system was measured using the soware’s goniometry
tool.
.4.2 The Owens two-liquid method. There is a close rela-
tionship between the surface free energy and the wettability of
a rock surface. In order to investigate the wettability alteration
of the rock, its surface free energy was studied using the Owens
2.2 Synthesis of the gas-wetting alteration agent
The gas-wetting alteration agent was synthesized according to
the following procedures:
Firstly, peruorooctanoyl chloride and calcium oxide were
added to a ask in a molar ratio of 2 : 1 under a nitrogen
atmosphere, and then anhydrous ethanol was added as solvent.
Then, ammonia (a 3-fold molar excess of peruorooctanoyl
chloride) was injected and stirred for 4 h. The mixture was
15
2

ltered under reduced pressure and dried in a universal oven at
ꢀ
78 C to obtain peruorooctanoyl ammonia. This rst reaction
is described in Scheme 1(a).
16
two-liquid method. The surface free energy consists of the
dispersion force and the polar force and the specic calculation
equation is as follows:
Secondly, 0.1 mol of peruorooctanoyl ammonia was placed
in a three-necked ask with anhydrous ethanol and triethyl-
amine as the solvent and catalyst, respectively. Then, 0.1 mol of
peruorooctanoyl chloride was added dropwise under stirring
1
7
D
s
P
s
g
s
¼ g
+ g
(1)
(2)
ꢀ
and the temperature was kept below 5 C for 6 h. N,N-bis(per-

uorooctyl)imine was produced aer removing the solvent and
D
s
D 1/2
)
P P 1/2
+ 2(g g )
s L
g
L
(1 + cos q) ¼ 2(g
g
L
impurities. This procedure is shown in Scheme 1(b).
Finally, N,N-bis(peruorooctyl)imine was added into a solu-
tion of acetone in a three-necked ask and sufficiently dissolved
at 60 C. Next, a solution of sodium chloroacetate was added
dropwise to the mixture and vigorously stirred at room
temperature for 6 h. The reaction mixture was ltered and
concentrated under reduced pressure. Then, the residue was
In eqn (1) and (2), g is the surface free energy of the solid;
s
D
P
g
s
and g
s
are the dispersion force and polar force of the solid,
is the surface free energy of liquid; q is the
ꢀ
respectively; g
contact angle; g
L
D
P
L L
and g are the dispersion force and polar force
of the liquid, respectively.
D
P
18
s s
Variables g and g can be calculated using eqn (3) and (4).
D
gL1(1 + cos q ) ¼ 2(g g
D
L1
1/2
P
s
P
L1
1/2
)
)
+ 2(g g
)
)
(3)
(4)
1
s
Table 1 The basic parameters of rock
D
s
D
L2
1/2
P
s
P
L2
1/2
g
L2(1 + cos q
2
) ¼ 2(g
g
+ 2(g
g
Porosity
(%)
Permeability
(mm )
2
Type
Composition
In eqn (3) and (4), gL1 is the surface free energy of water; q is the
contact angle of water on the rock surface; g and g are the
L1 L1
dispersion force and polar force of water, respectively; gL2 is the
surface free energy of n-hexadecane; q is the contact angle of n-
1
D
P
11.8 ꢂ 10ꢁ5
Shale
4.13
Clay (>40%), quartz (>35%),
carbonate (<20%)
2
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Scheme 1 Synthesis of the gas-wetting alteration agent.
D
P
hexadecane on the rock surface; gL2 and gL2 are the dispersion capillary tube was washed with distilled water and dried at high
force and polar force of n-hexadecane, respectively. temperature. Then, the cleaned glass capillaries were treated in
.4.3 Imbibition. A spontaneous imbibition test can be a gas-wetting alteration agent solution for 24 h and dried at
2
conducted to evaluate the effect of wettability on uid imbibed a certain temperature to remove excess solution from the tube.
into the rock. The amount of liquid imbibed versus time was Finally, the treated glass capillaries were inserted into the
recorded using a balance when the bottom of rock touched the solution. During the process, the liquid was sucked into the
19,20
liquid surface.
The readability of the balance was 0.001 g. A tube by capillary force. A schematic diagram is shown in Fig. 2.
schematic showing the spontaneous imbibition test is exhibited If the liquid was positive in the capillary (h > 0), the contact
ꢀ
in Fig. 1.
angle of the liquid on the rock surface was less than 90 ; when
2
.4.4 The glass capillary tube rise test. The glass capillary the liquid was neutral in the tube (h ¼ 0), the contact angle was
ꢀ
tube rise test was performed to verify the effect of the gas- equal to 90 ; and if the liquid was negative (h < 0), then the
wetting alteration agent on wettability alteration. The capillary contact angle of liquid was greater than 90 . The specic
ꢀ
radius used in this study was about 0.5 mm. Firstly, the glass contact angle in the gas–liquid–rock system could be computed
using eqn (5), where s and r represent the surface tension and
density of the liquid, respectively; r is the radius of the glass
capillary; q is the contact angle; h is the height of the liquid in
21,22
the glass capillary and g is the gravitational acceleration.
ꢀ
ꢁ
rghr
q ¼ arc cos
(5)
2s
3
. Results and discussion
3.1 FTIR spectrum
The infrared spectrum of the gas-wetting alteration agent is
shown in Fig. 3. The absorption peak of C–H appears at
ꢁ1
ꢁ1
ꢁ1
2
957 cm . The peaks at 1252 cm and 1149 cm correspond
Fig. 1 The simple device for spontaneous imbibition testing.
to the characteristic absorption of –CF and –CF , respectively.
3
2
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Fig. 2 The simple device for glass capillary tube rise testing.
The stretching vibration absorption of the C]O–N group
ꢁ
1
occurs at 1695 cm . Moreover, the characteristic peak of the
ꢁ
1
C]O–NH group at 3300–3100 cm disappears, indicating that
the monomers have reacted adequately. Furthermore, the
ꢁ
1
carboxylate stretching peaks are shown at 1603 cm
and
ꢁ
1
1398 cm .
1
3
.2 H NMR spectrum
1
The gas-wetting alteration agent was characterized by H NMR
and the spectrum is presented in Fig. 4. The peaks at d 2.508
and d 3.331 correspond to the solvent (DMSO) and deionized
water, respectively. The single peak at d 5.601 for H is assigned
1
Fig. 4 H NMR spectrum of the gas-wetting alteration agent.
to the –CH group. This observation can be explained by the
2
chemical shi of hydrogen in the methylene group moving
upeld due to the strong electron-withdrawing amide group
and the role of the carboxylate. The result is in good agreement
with the infrared analysis, indicating that the product has been
successfully synthesized.
ꢀ
During the rst stage, before 170 C, there is almost no weight
ꢀ
ꢀ
loss. In the second stage, from 170 C to 230 C, the weight loss
is about 9%, which may be attributed to the evaporation of the
residual solvent during the purication process. There was
a signicant increase in weight loss between 230 C and 400 C,
with the maximum weight loss rate peaking at about 1.267%
ꢀ
ꢀ
3.3 Thermal stability
ꢀ
ꢁ1
ꢀ
The thermal analysis revealed the stability of the gas-wetting
alteration agent when the temperature is increased. As seen in
Fig. 5 there are four stages of weight loss in the TGA curve.
C
at 270 C with a relatively narrow reaction interval. The
acceleration of weight loss at this stage indicates that thermal
Fig. 3 FTIR spectrum of the gas-wetting alteration agent.
Fig. 5 The thermal stability curves of the gas-wetting alteration agent.
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ꢀ
19 , respectively. The results were better than the literature
1
25–27
data.
The respective contact angles of water and n-hex-
ꢀ
ꢀ
adecane remained at about 140 and 119 with further increases
in concentration. Pictures of the drops on the rock surface
before and aer treatment with different concentrations are
shown in Fig. 7.
This observation may be explained as follows: at low
concentrations, a small amount of molecules are adsorbed on
the surface of the rock through van der Waals forces and these
adsorbed molecules are easily desorbed or replaced by mole-
cules in other solutions. At higher concentrations, the adsorp-
tion capacity is greater than that of desorption, resulting in an
increase of the amount of gas-wetting alteration agent adsorbed
Fig. 6 The contact angles of water and n-hexadecane on rock on the rock and the formation of a gas-wetting molecular layer
surfaces.
on its surface. As a result of this, the wettability of the rock is
altered from strong liquid-wetting to gas-wetting. With a further
increase of concentration, the adsorption capacity of the rock
surface tends to be saturated and so the wettability becomes
ꢀ
decomposition has occurred. Above 400 C, the remaining
weight ratio is less than 10%, which can be assigned to the
carbon residue. These results show that the synthesized gas-
wetting alteration agent decomposes at higher temperatures
stable. Therefore, the contact angle of water or n-hexadecane
28,29
remains essentially unchanged.
ꢀ
23,24
compared to literature data (120–140 C).
This demonstrates
3.5 The surface free energy
that it has a great potential in terms of temperature tolerance
and can be applied to unconventional reservoirs.
The surface free energy is a crucial feature when altering the
wettability of a rock surface. Table 2 shows the change in the
surface free energy of the rock before and aer treatment with
different concentrations. It can be seen that the surface free
3.4 Contact angle measurements
ꢁ1
ꢁ1
The contact angles of water and n-hexadecane on the rock energy was rapidly reduced from 72 mN m to 3.4 mN m
surface before and aer treatment were measured and the aer treatment with a concentration of 0.3 wt%. With the
results are shown in Fig. 6. Initially, the rock surface showed increase in concentration, the surface free energy did not
strong liquid-wetting with contact angles of water and n-hex- decrease signicantly. This result is consistent with studies by
ꢀ
ꢀ
30,31
adecane of 36 and 0 , respectively. However, aer treatment Gindl and Jiang et al.
However, when the concentration
with the gas-wetting alteration agent, the wettability of the rock exceeded 0.9 wt%, the surface free energy had a tendency to
was changed to preferential gas-wetting. When the concentra- gradually increase. A reasonable explanation is that when the
tion of the gas-wetting alteration agent was 0.1 wt%, the polar segments of the gas-wetting alteration agent are adsorbed
ꢀ
ꢀ
contact angle of water changed from 36 to 60 , while that of into the rock by electrostatic forces, the non-polar segments
ꢀ
ꢀ
n-hexadecane increased from 0 to 43 . With the increase in with double-repellent chains are exposed to the surface of the
concentration of the agent, the contact angles of water and rock. Moreover, these further form a strong hydrophobic and
n-hexadecane increased continuously. When the concentration oleophobic molecular layer which alters the wettability of the
ꢀ
was 0.5 wt%, the contact angles reached maximums of 140 and rock surface. Unfortunately, when the concentration exceeds
Fig. 7 The pictures of the droplets on the rock suface.
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Table 2 The surface free energy of the rocks
both water and n-hexadecane reveals that the wettability of the
rock has been altered from strong liquid-wetting to gas-wetting,
which agrees with the results of Giraldo et al. and Lai et al.
Concentration (%)
Surface free energy (mN m
0
72
0.3
3.4
0.5
3.2
0.7
2.9
0.9
4.5
1.2
7.1
33
34
ꢁ1
)
3.7 Capillary tube rise testing
the optimum value, the surface free energy has a tendency to
gradually increase with an increase in concentration. The
reason is that the bimolecular chains may be entwined with
each other, leading to a portion of the nonpolar segments being
locked. As a result, the surface free energy exhibits a small
The glass capillary tube rise test was performed to further
demonstrate the wettability alteration of the rock. Fig. 9
summarizes the liquid level in the capillary tube as a function of
the treatment concentrations. It can be clearly observed that the
water level was rapidly reduced from 31 mm to approximately
32
rebound.
ꢁ
13 mm as the concentration of the agent increased. Moreover,
the n-hexadecane level was conrmed to show a similar trend to
the water. Therefore, it was sufficient to indicate that the
wettability of the capillary inner wall was changed to gas-
wetting. The results of the glass capillary rise testing were
3.6 Imbibition
The wettability of the rock before and aer treatment was
determined by spontaneous imbibition. The dynamic process of
water or n-hexadecane imbibed into the rock was conducted by
recording the weight of the liquid over time until there was no
signicant change. Fig. 8(a) shows that the volume of water
imbibed into the rock was 0.83 g without the chemical treat-
ment, while the value sharply decreased to 0.07 g aer treat-
ment with 0.3 wt%. This indicates that the rocks have become
strongly hydrophobic. Fig. 8(b) shows the n-hexadecane
imbibed into untreated and treated rock. The amount of
imbibed rock decreased signicantly from 0.87 g to 0.25 g aer
treatment, which demonstrates that the rock has an oleophobic
property aer chemical treatment. The substantial reduction in
35
consistent with literature data. Accordingly, the agent could
effectively improve the rate of fracturing uid owback and
maintain the blocks with high yields, while promoting the
outow of extra liquid to reduce any damage to the formation.
3.8 SEM
Fig. 10 displays the microstructure of the rock surface before
and aer treatment. Fig. 10(a) shows that almost no material
covered the surface of the original rock and its surface was
relatively smooth. This observation could promote the expan-
sion of liquid on the rock’s surface, which further illustrates the
reason why the initial wettability of the reservoir is liquid-
wetting. However, it can be clearly seen from Fig. 10(b) that
the morphology of the rock surface has been signicantly
changed aer treatment with the gas-wetting alteration agent.
The surface of the rock adsorbs a large number of agent mole-
cules through van der Waals forces and forms a tight adsorption
layer, which effectively improves the roughness of the rock
surface. In addition, the surface free energy can be signicantly
reduced aer treatment. Thus, the wettability of the rock
surface is altered from water-wetting or oil-wetting to gas-
wetting. This is consistent with what has been reported in the
36,37
literature.
Fig. 8 Imbibition by liquid into the rock before and after treatment: (a)
water and (b) n-hexadecane.
Fig. 9 The water level in the capillaries before and after treatment.
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Fig. 10 SEM images of the rock surface: (a) original rock and (b) treated.
Fig. 11 Results of EDS of the rock surface: (a) original rock and (b) treated.
3
.9 EDS
can be adsorbed into the rock by electrostatic forces, while the
non-polar segments with double-repellent chains are exposed to
its surface and form a strong hydrophobic and oleophobic
molecular layer. Furthermore, the analysis by SEM and EDS also
suggests that the effect of the agent on gas-wetting alteration
can be ascribed to the increase in the roughness of the rock
surface and the decrease in the surface free energy.
Fig. 11 illustrates the elements of the rock surface before and
aer it was modied by the gas-wetting alteration agent. As
shown in Fig. 11(a), there was no uorine element in the orig-
inal rock sample, which was mainly composed of elements such
as calcium, potassium, oxygen and silicon. The presence of Au
was due to the spray before the test. It can be seen from
Fig. 11(b) that uorine has been found on the treated rock
surface. This shows that uorine can be sufficiently adsorbed Conflicts of interest
on the surface of the rock. This is the primary cause of the gas-
There is no conict to declare.
wetting alteration of the reservoir and is consistent with the
38
research of Aminnaji et al.
Acknowledgements
Financial support by the Fundamental Research Funds for the
National Key Basic Research Program of China (No.
4
. Conclusions
In this work a gas-wetting alteration agent was synthesized and 2015CB250904) and Central Universities (No. 15CX06034A) is
1
characterized by FTIR and H NMR. Thermal gravimetric anal- gratefully acknowledged. The funders had no conict of interest
ysis exhibited that the synthesized gas-wetting alteration agent or any role in the study design, data collection and analysis,
ꢀ
can resist temperatures up to 230 C. The contact angle method decision to publish or preparation of the manuscript.
was used to examine the wettability of the rock before and aer
treatment. The results show that the wettability of the rock
surface is altered from its original strong liquid-wetting to gas-
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explained by the special chemical structure, compared with the
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RSC Adv., 2018, 8, 7924–7931 | 7931