Study on the Asphaltene Precipitation in CO2 ... - ACS Publications

Subscriber access provided by READING UNIV

Article

Study on the Asphaltene Precipitation in CO2 Flooding: A Perspective from Molecular Dynamics Simulation Timing Fang, Muhan Wang, Jiawei Li, Bing Liu, Yue Shen, Youguo Yan, and Jun Zhang Ind. Eng. Chem. Res., Just Accepted Manuscript • DOI: 10.1021/acs.iecr.7b03700 • Publication Date (Web): 26 Dec 2017 Downloaded from http://pubs.acs.org on December 26, 2017

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

Industrial & Engineering Chemistry Research is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Industrial & Engineering Chemistry Research

3

Study on the Asphaltene Precipitation in CO2 Flooding: A Perspective from Molecular Dynamics Simulation

4

Timing Fang, Muhan Wang, Jiawei Li, Bing Liu, Yue Shen, Youguo Yan*, Jun Zhang*

5

College of Science, China University of Petroleum, Qingdao 266580, Shandong, China

6

Abstract: The asphaltene precipitation is a common phenomenon in the exploitation of crude

7

oil and closely correlates with the oil recovery, especially in CO2 flooding. In this work,

8

employing molecular dynamics simulations, the asphaltene precipitation process in CO2 was

9

investigated. The simulation results reveal that the CO2 could step-by-step extract nonpolar

10

and light polar components from asphaltene micelle, and a two-step asphaltene precipitation

11

process was illustrated. In our eight asphaltene molecule system, first, four asphaltene dimers

12

formed. Two dimers get together into one aggregation in bulk, the other two dimers get

13

together and adsorbed onto the silica surface. After that, the surface aggregation further

14

induces the adsorption of bulk aggregation onto it to complete asphaltene precipitation. In

15

addition, we also studied the pressure effect on asphaltene precipitation. Our work provided a

16

molecular level understanding of asphaltene precipitation phenomenon in CO2 flooding, and

17

the results have significant promise for the oil exploitation.

18

Keywords: CO2 flooding; Molecular dynamics simulation; Asphaltene precipitation

19

1. Introduction

20

Global warming has become one of the most important environmental problems. Carbon

1 2

ACS Paragon Plus Environment

Industrial & Engineering Chemistry Research 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

21

capture and storage (CCS) has been widely recognized as a potential alternative which can

22

reduce carbon dioxide (CO2) and mitigate climate warming effectively [1, 2]. CCS can not

23

only reduce CO2 emissions, but also enhance the oil recovery (EOR); this method has been

24

widely used in oil field development [3, 4]. CO2 flooding has been employed as EOR

25

approach since the 1970s [5-8]. CO2 can dissolve into the crude oil and lower its viscosity,

26

improving the oil mobility [9-12]. However, CO2 would preferentially extract light oil

27

components and result in the precipitation of heavy oil components, especially asphaltene.

28

The precipitation would reduce the effective oil flow aperture and deteriorate the oil recovery

29

[13, 14]. Thus, it is necessary to reveal the precipitation phenomenon, which is helpful to

30

develop a strategy to solve the problem mentioned above.

31

In the past decades, the precipitation behavior has attracted great attention, and abundant

32

researches have been done meanwhile. For example, Hu et al. [15] investigated the CO2

33

effects on asphaltene precipitations under the reservoir condition, revealing that asphaltene

34

precipitation was detected when the operating pressure approached or exceeded the minimum

35

miscibility pressure. Other studies of Verdier et al. [16] and Srivastava et al. [17] suggested

36

that high temperature and low pressure facilitated the occurring of asphaltene precipitation,

37

and the increase of injected CO2 volume fraction also enhanced the asphaltene precipitation.

38

Carauta et al. [18] studied the stability of asphaltene dimers in a series of solvents by

39

measuring the distance between the molecular cores. The researchers found that the most

40

stable dimers were in heptane and the most unstable dimers were in toluene. Despite

41

modeling studies, it is not yet clarified in detail because it is still a notable challenge to

42

observe this microscopic process under reservoir conditions to reveal key insight into the

43

asphaltene precipitation in CO2 flooding.


Page 2 of 20

Page 3 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


44

The mechanism of molecular attraction or separation can be described by using molecular

45

dynamics simulation, which could reveal the relationship between molecular distribution and

46

environment changes. An understanding of the interaction between asphaltene molecules and

47

mineral surfaces in CO2 flooding, is not only germane to clarify the mechanism of their

48

deposition, but also gradually important for the energy demand.

49

In this study, molecular dynamics (MD) simulation was performed to investigate the

50

asphaltene precipitation process in CO2 flooding at the molecular level. The present study is

51

divided into three parts: Firstly, the formation and structural features of asphaltene micelle

52

were analyzed. Secondly, the extraction process of nonpolar and light oil components in CO2

53

flooding was presented, besides, the asphaltene precipitation could be divided into two steps:

54

aggregation and adsorption to the silica surface. Furthermore, the effect of pressure on

55

asphaltene precipitation was also studied. This study provides considerable insights into the

56

behaviors of asphaltene molecules in CO2 flooding.

57

2. Methods

58

2.1. Force field

59

MD

60

Condensed-Phase-Optimized

61

(COMPASS) were used to consider interatomic interaction [19]. COMPASS, a widely used

62

all-atom force field based on ab initio and optimization by the experimental data, has been

63

validated to be capable of accurately predicting structural and thermophysical properties for a

64

broad range of organic and inorganic substances including CO2, silica and oil accurately [20,

65

21]. COMPASS includes the bonded and non-bonded potential. The bonded potential consists

66

of bond stretching, angular bending, dihedral angle torsion, cross terms and out-of-plane

simulation

was

performed

by

Molecular

Materials Potential

Studio. for


The

Atomistic

force Simulation

field

of

Studies


Page 4 of 20

67

interactions as shown; the non-bonded potential is composed of long-range electrostatic

68

interaction and short-range van der Waals (vdW) interaction. The electrostatic interaction was

69

revealed by Coulombic equation and the vdW interaction was represented by 9-6

70

Lennard-Jones function, which are described by the following equation [22].

71

= + + + + + +

72

= 2 − 3 "

= #

73

$% $&

!

'

(1) (2) (3)

74

2.2. Model construction

75

The microscopic structure of asphaltene will have some impacts on the asphaltene

76

aggregation. There have been recent advances in the structural elucidation of asphaltene

77

molecules [23] and explained the process of aggregation. Boek et al. [24] used a quantitative

78

molecular representation (QMR) algorithm to generate a range of molecular representative

79

asphaltene architectures, which showed that the consistency between MD simulation and

80

experimental data. Based on the structure information, Hu et al. [25] revealed that pure CO2

81

would enhance the hydrogen bond and the dipolar interaction in asphaltene aggregates. The

82

π-π charge-transfer interaction will be greatly enhanced after CO2 injection. This indicates

83

that the more aromatic clusters and heteroatoms the asphaltenes have, the greater the

84

deposition of asphaltene will be after CO2 injection. Sedghi et al. [26] confirmed that the

85

interactions between aromatic cores of asphaltene molecules are the major driving force for

86

the association. Moreover, the length and number of aliphatic chains do not seem to have a

87

noticeable effect on asphaltene dimerization. However, Costa et al. [27] revealed the

88

unexpected simulation results, which showed that the π–π stacking interaction and van der

89

Waals forces between aromatic rings did not result in significant aggregation, but functional


Page 5 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


90

group surrounding the aromatic core played a critical part in the molecular interaction. Thus,

91

it is a long-standing debate about asphaltene molecular architecture and properties mentioned

92

above.

93

In general, there is some consensus that asphaltene can be divided into "continental" and

94

"archipelago" types [28, 29]. Based on those two types, analysis of the asphaltene aggregation

95

suggests that asphaltene molecules are generally spherical, with the archipelago model

96

favoring longer prolate structures and the continental model tending toward oblate structures

97

[30]. Different types may also coexist in the real asphaltene. However, in order to reduce the

98

computational cost, the "average" asphaltene molecules are used to represent the system. In

99

this study, the continental model (C54H65NO2S) is used, because it can form aggregates

100

through the accumulation of aromatic regions and is widely used as the basis for molecular

101

models [31, 32]. This simplification is feasible because recent studies have shown that a

102

well-defined compound can be used to mimic the asphaltene aggregation process successfully

103

[33]. The model resin is selected from the published reference [28] and saturated hydrocarbon

104

is dodecane molecules. The molecules were constructed by Sketch Atom tool of the Materials

105

Studio software and optimized by Forcite calculation/Geometry Optimization with COMPASS

106

Forcefield.

107

We know that oil samples are usually divided into four fractions, including asphaltene,

108

resin, aromatic and saturated hydrocarbon [34]. However, to simplify the models, resin

109

molecules was used instead of the aromatic component due to the role aromatic played is

110

similar to the resin component [32]. Therefore, the oil film in this study contains asphaltene,

111

resin and saturated hydrocarbon components as shown in Fig. 1, a similar approach was also

112

used in some experiment research [35].



113 114

Figure 1. Molecular structure of model asphaltene (a), resin (b) and hydrocarbon (c).

115

2.3. Simulation details

116

The constructed oil film contains 8 asphaltene molecules, 40 resin molecules and 32

117

hydrocarbon molecules (C12) using amorphous method, which roughly corresponds to a mass

118

ratio in the reported literature [36]. The dimensions of hydroxylated silica surface were 54.01

119

Å × 32.27 Å × 13.71 Å. The silica surface was built by cleaving the α-quartz along the (100)

120

crystallographic orientation [37, 38]. The oil film was placed on top of the hydroxylated silica

121

surface. A 5 ns NVT (constant atoms number N, volume V a temperature T) simulation was

122

performed to get an initial equilibrated adsorption configuration of the oil film on silica

123

surface. In this simulation, the periodic boundary conditions were applied in the XY

124

dimensions. Then, a 105 Å CO2 phase in thickness was placed onto the equilibrated oil layer.

125

At the top of the bulk CO2 phase, a dense CO2 layer with a thickness of 5.2 Å was fixed to

126

prevent the CO2 escaping and maintain the CO2 pressure [20]. An 18 Å vacuum slab in

127

thickness was added outmost to eliminate the effect of periodic boundary condition. A 10 ns

128

NVT simulation was implemented to observe the precipitation process. In this simulation, the

129

periodic boundary conditions were applied in three dimensions. In two MD simulations, the

130

temperature was kept at 373 K controlled by an Andersen thermostat [39, 40], a time step of 1


Page 6 of 20

Page 7 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


131

fs was adopted, and every 1000 steps puts a frame for data analysis.

132

3. Results and discussion

133

3.1 Formation of asphaltene micelle

134

First, we want to get the appropriate micelle structure, which is the base to research the

135

asphaltene precipitation phenomenon. Fig. 2(a) gives the final equilibrium configurations, a

136

micelle forms on the silica surface, and detailed observation indicates that eight asphaltene

137

molecules form four dimers, as signed by four individual configures for clearness. The dimer

138

formation could be ascribed to their strong π-π electron interaction [41], the further

139

explanation could be found in Section 1 of Supporting Information. The micellar profile (Fig.

140

2(b)) indicates the asphaltenes locate in the center, while the lighter components including

141

aromatic and saturated hydrocarbons locate outside. For clarity, a structural schematic of

142

micelle was presented.

143

Furthermore, the radial distribution functions (RDFs) profiles (center-to-center of

144

molecules) of asphaltene-asphaltene, asphaltene-resin and asphaltene-hydrocarbon were

145

calculated to reveal the spatial distribution in Fig. 2(c). The RDFs could be calculated by

146

equation [42]: g(r) = ρ(r)/ρo, where ρ(r) is the local number density and ρo is the bulk number

147

density. The RDFs describes the probability of the particle B presents at the distance r from

148

the target particle A. This probability is described by the ratio of local number density to the

149

bulk number density of particle B, which reflects the spatial distribution of B around A [22].

150

Here, the g(r)asphaltene-asphaltene is related to the probability of finding an asphaltene molecule at

151

distance r from another asphaltene molecule as shown in Fig. 2(c). For g(r)asphaltene-resin and

152

g(r)asphaltene-hydrocarbon, the peaks are further distances of approximately 4.85 and 6.15 Å

153

respectively, while the peak of g(r)asphaltene-asphaltene is located at approximately 3.65 Å. Thus,



154

these results confirm micellar structure characteristics as shown in Fig. 2(b). Our obtained

155

micelle and interlayer distance are well consistent with reported simulation [43] and

156

experiment result which is observed by X-ray diffraction [44].

157 158

Figure 2. (a) Equilibrium conformations of the sorption system after 5 ns MD simulation. Four

159

configurations were presented here to give four asphaltene dimers for clearness, (b) a cross-section view of

160

the micelle and a structural schemetic. Color codes: asphaltene, blue; resin, red; alkane, green. (c) RDFs of

161

different components in micelle.

162

3.2 Asphaltene precipitation phenomenon

163

Fig. 3(a) exhibits the dynamical precipitation process, as seen, the hydrocarbon components

164

first extracted by the CO2, and then the resin molecules gradually dissolve into the CO2 phase.

165

The density distribution of resin and hydrocarbon at 2.5 ns and 5.5 ns was depicted in Fig.

166

3(b), which reveals the process of step-by-step dissolution. In this extracting process, the

167

asphaltene molecules merge together to complete precipitation. Furthermore, RDFs of the

168

molecular mass center of various oil components were calculated to quantitatively display the

169

precipitation process in Fig. 3(c-e). As described above, the asphaltene cores are surrounded

170

by the resin and hydrocarbon components in the equilibrated micelle. Along with the

171

simulation, the RDF peak of asphaltene-asphaltene gradually rises, indicating that the

172

asphaltene molecule approaching together in the simulation. While the RDF peaks of

173

asphaltene-resin and asphaltene-hydrocarbon gradually decrease. With these changes, the ACS Paragon Plus Environment

Page 8 of 20

Page 9 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


174

separation between molecules could be reflected. The RDF changes clearly illustrate the

175

asphaltene precipitation and resin (hydrocarbon) dissolution.

176

177 178

Figure 3. (a) Side views for the evolutions of CO2 extracting oil components from 1 ns to 10 ns. (b)

179

Density distribution of resin and hydrocarbon at 2.5 ns and 5.5 ns. Radial distribution functions for

180

molecular mass centers between asphaltene and resin, hydrocarbon at (c) asphaltene-asphaltene, (d)

181

asphaltene-resin and (e) asphaltene- hydrocarbon.

182

Detailed observation gives a clear asphaltene precipitation process, as shown in Figure 4.

183

For clarity of presentation, only asphaltene molecules and silica surface are present.

184

Meanwhile, we found the initial aggregation of asphaltene molecules happens in bulk and

185

silica surface simultaneously, they are displayed in Fig. 4(a) and Fig. 4(b), respectively. In this

186

process, two asphaltene dimers first form and then merge into large aggregation. And then,

187

these two aggregations further fuse and the bulk one adsorbed onto the silica one to complete

188

the precipitation process (Fig. 4(c)). Overall, as displayed in Fig. 4(a-c), the asphaltene

189

precipitation could be divided into three sequential steps including initial formation of dimer,

190

the fusion of dimer, and last precipitation.



Page 10 of 20

191 192

Figure 4. The snapshots of asphaltenes aggregation process (a) happened in bulk (particle 1) and (b)

193

happened on silica surface (particle 2), and (c) coalescence process of two particles.

194

3.3 Asphaltene precipitation mechanism

195

The interaction energies between various components were calculated to probe physical

196

forces governing asphaltene precipitation as shown in Fig. 5. For instance, EHydrocarbon/CO2

197

could be calculated by equation (4) [45, 46],

198

() ⁄*+, = *+,.() − /*+, + () 0

(4)

199

Where EHydrocarbon/CO2 is the interaction energy between hydrocarbon and CO2, ECO2+Hydrocarbon

200

is the total potential energy of hydrocarbon and CO2. EHydrocarbon and ECO2 represent the

201

potential energy of hydrocarbon molecules and CO2 molecules. Increasingly negative energy

202

represents the increasing interaction between the two components.

203

Here, from Fig. 5 it can be observed that: (1) EHydrocarbon/CO2 is the major driver of dissolved

204

hydrocarbon; (2) the driving force of resin dissolution comes from EResin/CO2, in addition, the

205

weakened interaction between resin and asphaltene molecules can be observed from the

206

change of EResin/asphaltene, but partial resin molecules still adsorbed on asphaltene aggregation;

207

(3) the values of EAsphaltene/asphaltene and EAsphaltene/silica surface increased and held steady at the end

208

of simulation, which promote the asphaltene precipitation. Furthermore, solubility parameters


Page 11 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


209

are also analyzed to reveal the reason of different solubility of oil components in section 2 of

210

Supporting Information.

211 212

Figure 5. Dynamic interaction energy between various components including the silica surface during

213

asphaltene precipitation. (a) The interaction energy between hydrocarbon with others, (b) The interaction

214

energy between resin with others, (c) the interaction energy between asphaltene with others.

215

In addition, we performed umbrella sampling simulations to calculate the potential of mean

216

force (PMF) [47], as shown in Fig. 6. PMF between two particles provides a quantitative

217

description of the strength of aggregation. The difference in energy between the minimum of

218

the PMF and the value of the PMF at long distances can be interpreted as the free energy of

219

aggregation formation. For example, the value of free energy of dimer formation for

220

asphaltene molecules is 31.03 kJ/mol. A higher value of free energy corresponds to a more

221

stable system. Thus, the PMF comparison indicates that asphaltene molecules favor being the

222

larger asphaltene aggregation in CO2 flooding.



10

Potential of mean force kJ/mol

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

PMFs of asphaltenes monomer-monomer 0 monomer-dimer monomer-tetramer -10

-20

31.03

-30

32.12 35.87

-40 0

4

8

12

16 。

20

com-com distance / A

223 224

Figure 6. Potential of mean force curves for asphaltene in CO2 flooding between two monomers (black),

225

between a monomer and a dimer (red) and between a monomer and a tetramer (blue).

226

3.4 Pressure effect on Asphaltene precipitation

227

Based on previous studies [48-50], the asphaltene precipitation is sensitive to pressure

228

changes, high pressure is unfavorable to asphaltene precipitation. Here, we investigated this

229

phenomenon to reveal the underlying mechanism. In order to illustrate these progresses, side

230

views for the evolution of asphaltene molecules movement are shown in Fig. 7(a). Due to the

231

penetration of CO2 molecules and swelling of the oil phase, the asphaltene aggregation

232

became loose and disordered. This phenomenon became obvious with the increasing pressure,

233

which led to weakening the interaction between asphaltene molecules. Fig. 7(b) exhibits

234

PMFs of asphaltene-asphaltene at 20 MPa, 25 MPa and 40 MPa. With the increase of pressure,

235

it can be seen that the value of free energy of dimer formation for asphaltene molecules

236

decreased from 34.47 kJ/mol to 25.41 kJ/mol. In addition, Fig. 7(c) exhibits PMFs of

237

asphaltene-silica surface at 20 MPa, 25 MPa and 40 MPa. With the increase of pressure, the

238

value of free energy of the asphaltene molecules adsorbed on silica surface also became

239

smaller. Therefore, high pressure helps to weaken the adsorption strength of asphaltene

240

molecules on the surface. ACS Paragon Plus Environment

Page 12 of 20

Page 13 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


241

242 243

Figure 7. (a) Side views for the evolutions of asphaltene molecules movement versus the injection pressure

244

(20 MPa (the density of CO2: 0.48 g/ml), 25 MPa (CO2: 0.59 g/ml) and 40 MPa (CO2: 0.76 g/ml)) of CO2

245

flooding. Potential of mean force curves between two asphaltene monomers (b) and between asphaltene

246

and silica surface (c).

247

4. Conclusions

248

In this study, the asphaltene precipitation process in CO2 was investigated by adopting

249

molecular dynamic simulations. The dynamical simulation process identifies that the CO2

250

could extract nonpolar and light polar components step-by-step, and a two-step precipitation

251

process was found. First, the asphaltene dimers form and then grow up into large aggregation

252

in two modes, one happens in bulk, the other happens on the silica surface. Besides, the

253

surface aggregation inducing the further adsorption of bulk aggregation to complete

254

precipitation was investigated. Potential of mean force calculations show that further

255

asphaltene aggregation in size becomes more favored in CO2 flooding, and the aggregation in

256

size and adsorption on silica surface become less favored at high pressures. Our work



257

provided the understanding of asphaltene precipitation at a molecular level, and the results

258

have significant promise for the oil exploitation and might show some application prospect in

259

the future.

260

ASSOCIATED CONTENT

261

Supporting Information. Section 1: Spatial distribution of asphaltene molecules. Section 2:

262

Cohesive energy density and solubility parameter for different components.

263

AUTHOR INFORMATION

264

Corresponding author

265

*Tel.: +86 0532-86983366 E-mail: [email protected] (Jun Zhang)

266

Notes

267

The authors declare no competing financial interest.

268

ACKNOWLEDGMENT

269

This work is financially supported by the National Basic Research Program of China

270

(2014CB239204, 2015CB250904), the National Natural Science Foundation of China

271

(U1262202), the Fundamental Research Funds for the Central Universities (15CX08003A,

272

14CX05022A, 15CX05049A, YCX2017067).

273

REFERENCES

274

(1) Liu, H.; Tellez, B. G.; Atallah, T.; Barghouty, M. The role of CO2 capture and storage in

275

Saudi Arabia's energy future. Int J Greenh Gas Con. 2012. 11, 163-171.

276

(2) Abas, N.; Khan N. Carbon conundrum, climate change, CO2 capture and consumptions. J

277

CO2 Util. 2014. 8, 39-48.

278

(3) Czarnota, R.; Janiga, D.; Stopa, J.; Wojnarowski, P. Determination of minimum miscibility

279

pressure for CO2 and oil system using acoustically monitored separator. J CO2 Util. 2017. 17, ACS Paragon Plus Environment

Page 14 of 20

Page 15 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


280

32-36.

281

(4) Li, S.; Li, Z.; Dong, Q. Diffusion coefficients of supercritical CO2 in oil-saturated cores

282

under low permeability reservoir conditions. J CO2 Util. 2016. 14, 47-60.

283

(5) Mondal, S.; De, S. CO2 based power cycle with multi-stage compression and intercooling

284

for low temperature waste heat recovery. Energy. 2015. 90, 1132-1143.

285

(6) Zanganeh, P.; Dashti, H.; Ayatollahi, S. Visual investigation and modeling of asphaltene

286

precipitation and deposition during CO2 miscible injection into oil reservoirs. Fuel. 2015. 160,

287

132-139.

288

(7) Lee, T.; Bocquet, L.; Coasne, B. Activated desorption at heterogeneous interfaces and

289

long-time kinetics of hydrocarbon recovery from nanoporous media. Nat Commun. 2016. 7.

290

(8) Han, J.; Lee, M.; Lee, W.; Lee, Y.; Sung, W. Effect of gravity segregation on CO2

291

sequestration and oil production during CO2 flooding. Appl Energ. 2016. 161, 85-91.

292

(9) Safi, R.; Agarwal, R.K.; Banerjee, S. Numerical simulation and optimization of CO2

293

utilization for enhanced oil recovery from depleted reservoirs. Chem Eng Sci. 2016. 144,

294

30-38.

295

(10) Nasrabadi, H.; Moortgat, J.; Firoozabadi, A. New Three-Phase Multicomponent

296

Compositional Model for Asphaltene Precipitation during CO2 Injection Using CPA-EOS.

297

Energ Fuel. 2016. 30, 3306-3319.

298

(11) Zhang, J.; Pan, Z.; Liu, K.; Burke, N. Molecular Simulation of CO2 Solubility and Its

299

Effect on Octane Swelling. Energ Fuel. 2013. 27, 2741-2747.

300

(12) Cao, M.; Gu, Y. Oil recovery mechanisms and asphaltene precipitation phenomenon in

301

immiscible and miscible CO2 flooding processes. Fuel. 2013. 109, 157-166.

302

(13) Cao, M.; Gu, Y. Temperature effects on the phase behaviour, mutual interactions and oil

303

recovery of a light crude oil–CO2 system. Fluid Phase Equilibr. 2013. 356, 78-89.

304

(14) Gonzalez, D. L.; Vargas, F. M.; Hirasaki, G. J.; Chapman, W. G. Modeling study of

305

CO2-induced asphaltene precipitation. Energ Fuel. 2007. 22, 757-762.

306

(15) Hu, Y. F.; Li, S.; Liu, N.; Chu, Y. P.; Park, S. J.; Mansoori, G. A.; Guo, T. M.

307

Measurement and corresponding states modeling of asphaltene precipitation in Jilin reservoir

308

oils. J. Pet. Sci. Eng. 2004. 41, 169−182.

309

(16) Verdier, S.; Carrier, H.; Andersen, S. I.; Daridon, J. L. Study of pressure and temperature

310

effects on asphaltene stability in presence of CO2. Energ Fuel. 2006. 20, 1584−1590. ACS Paragon Plus Environment


311

(17) Srivastava, R. S.; Huang, S. S. Asphaltene deposition during CO2 flooding: A laboratory

312

assessment. SPE Production Operations Symposium. Society of Petroleum Engineers. 1997.

313

(18) Carauta, A. N.; Seidl, P. R.; Chrisman, E. C.; Correia, J. C.; Menechini, P. D. O.; Silva, D.

314

M.; Leal, K. Z.; de Menezes, S. M. C.; de Souza, W. F.; Teixeira, M. A. G. Modeling solvent

315

effects on asphaltene dimers. Energ Fuel. 2005, 19, 1245-1251.

316

(19) Sun, H. COMPASS: an ab initio force-field optimized for condensed-phase applications

317

overview with details on alkane and benzene compounds. J Phys Chem B. 1998. 102,

318

7338-7364.

319

(20) Osnis, A.; Sukenik, C. N.; Major, D. T. Structure of carboxyl-acid-terminated

320

self-assembled monolayers from molecular dynamics simulations and hybrid quantum

321

mechanics–molecular mechanics vibrational normal-mode analysis. J Phys Chem C. 2012.

322

116, 770-782.

323

(21) Yang, J.; Ren, Y.; Tian, A. COMPASS force field for 14 inorganic molecules, He, Ne, Ar,

324

Kr, Xe, H2, O2, N2, NO, CO, CO2, NO2, CS2, and SO2, in liquid phases. J Phys Chem B. 2000.

325

104, 4951-4957.

326

(22) Accelrys. Material Studio, Accelrys Software Inc., San Diego, CA; 2010.

327

(23) Schuler, B.; Meyer, G.; Peña, D.; Mullins, O. C.; Gross, L. Unraveling the molecular

328

structures of asphaltenes by atomic force microscopy. J. Am. Chem. Soc. 2015. 137,

329

9870−9876.

330

(24) Boek,E. S. Yakovlev, D. S. Headen, T. F. Quantitative molecular representation of

331

asphaltene and molecular dynamics simulation of their aggregation. Energ Fuel. 2009. 23,

332

1209-1219.

333

(25) Hu, M.; Shao, C.; Dong, L.; Zhu, J. Molecular dynamics simulation of asphaltene

334

deposition during CO2 miscible flooding. Petrol Sci Technol. 2011. 29, 1274-1284.

335

(26) Sedghi, M.; Goual, L.; Welch, W.; Kubelka, J. Effect of asphaltene structure on

336

association and aggregation using molecular dynamics. J. Phys. Chem. B. 2013. 117,

337

5765-5776.


Page 16 of 20

Page 17 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


338

(27) Costa, J.; Simionesie, D.; Zhang, Z. J.; Mulheran, P. A. Aggregation of model asphaltenes:

339

a molecular dynamics study. J. Phys. Condens. Matter. 2016. 28, 394002.

340

(28) Aguilera-Mercado, B.; Herdes, C.; Murgich, J.; Müller, E.A. Mesoscopic simulation of

341

aggregation of asphaltene and resin molecules in crude oils. Energ Fuel. 2006. 20, 327-338.

342

(29) Kuznicki, T.; Masliyah, J. H.; Bhattacharjee, S. Molecular dynamics study of model

343

molecules resembling asphaltene-like structures in aqueous organic solvent systems. Energ

344

Fuel. 2008. 22, 2379-2389.

345

(30) Headen, T. F.; Boek, E. S.; Jackson, G.; Totton, T. S.; Müller, E. A. Simulation of

346

Asphaltene Aggregation through Molecular Dynamics: Insights and Limitations. Energ Fuel.

347

2017. 31, 1108-1125.

348

(31) Kuznicki, T.; Masliyah, J. H.; Bhattacharjee, S. Molecular dynamics study of model

349

molecules resembling asphaltene-like structures in aqueous organic solvent systems. Energ

350

Fuel. 2008. 22, 2379-2389.

351

(32) Wu, G.; He, L.; Chen, D. Sorption and distribution of asphaltene, resin, aromatic and

352

saturate fractions of heavy crude oil on quartz surface: molecular dynamic simulation.

353

Chemosphere. 2013. 92, 1465-1471.

354

(33) Breure, B.; Subramanian, D.; Leys, J.; Peters, C. J.; Anisimov, M. A. Modeling

355

asphaltene aggregation with a single compound. Energ Fuel. 2012. 27, 172-176.

356

(34) Speight, J. G. The chemistry and technology of petroleum. CRC press, 2014.

357

(35) Zanganeh, P.; Ayatollahi, S.; Alamdari, A.; Zolghadr, A.; Dashti, H.; Kord, S. Asphaltene

358

deposition during CO2 injection and pressure depletion: A visual study. Energ Fuel. 2012. 26,

359

1412-1419.

360

(36) Li, X.; He, L.; Wu, G.; Sun, W.; Li, H.; Sui, H. Operational parameters, evaluation

361

methods, and fundamental mechanisms: aspects of nonaqueous extraction of bitumen from oil ACS Paragon Plus Environment


362

sands. Energ Fuel. 2012. 26, 3553-3563.

363

(37) Skelton, A. A.; Fenter, P.; Kubicki, J. D. Simulations of the Quartz (10ī1)/Water Interface:

364

A Comparison of Classical Force Fields, Ab Initio Molecular Dynamics, and X-ray

365

Reflectivity Experiments. J Phys Chem C. 2011. 115, 2076-2088.

366

(38) de Leeuw, N. H.; Higgins, F. M.; Parker, S. C. Modeling the surface structure and

367

stability of α-quartz. J Phys Chem B. 1999. 103, 1270-1277.

368

(39) Andersen, H. C. Molecular dynamics simulations at constant pressure and/or temperature.

369

J Chem Phys. 1980. 72, 2384-2393.

370

(40) Wang, X. J.; Zhao, X. Y.; Li, Q. G.; Chan, T. W.; Wu, S. Z. Artificial Neural Network

371

Modeling and Mechanism Study for Relaxation of Deformed Rubber. Ind Eng Chem Res.

372

2016. 55, 4059-4070.

373

(41) Amin, J. S.; Nikooee, E.; Ghatee, M. H.; Ayatollahi, S.; Alamdari, A.; Sedghamiz, T.

374

Investigating the effect of different asphaltene structures on surface topography and

375

wettability alteration. Appl Surf Sci. 2011. 257, 8341-8349.

376

(42) Gereben, O.; Petkov, V. Reverse Monte Carlo study of spherical sample under

377

non-periodic boundary conditions: the structure of Ru nanoparticles based on x-ray diffraction

378

data. J. Phys.: Condens. Matter. 2013. 25, 454211.

379

(43) Pacheco-Sánchez, J. H.; Zaragoza, I. P.; Martínez-Magadán, J. M. Asphaltene

380

aggregation under vacuum at different temperatures by molecular dynamics. Energ Fuel.

381

2003. 17, 1346-1355.

382

(44) Yen, T. F.; Erdman, J. G.; Pollack, S. S. Investigation of the structure of petroleum

383

asphaltenes by X-ray diffraction. Anal Chem. 1961. 33, 1587-1594.

384

(45) Fang, T. M.; Wang, M. H.; Wang, C.; Liu, B.; Shen, Y.; Dai, C. L.; Zhang, J. Oil

385

detachment mechanism in CO2 flooding from silica surface: Molecular dynamics simulation.

386

Chem Eng Sci. 2017. 164, 17-22.

387

(46) Zhong, J.; Wang, P.; Zhang, Y.; Yan, Y. G.; Hu, S. Q.; Zhang, J. Adsorption mechanism of

388

oil components on water-wet mineral surface: A molecular dynamics simulation study. Energy.

389

2013. 59, 295-300.

390

(47) Torrie, G. M.; Valleau, J. P. Nonphysical sampling distributions in Monte Carlo

391

free-energy estimation: Umbrella sampling. J Comput Phys. 1977. 23, 187-199.

392

(48) Guiliano, M.; Boukir, A.; Doumenq, P.; Mille, G.; Crampon, C.; Badens, E.; Charbit, G. ACS Paragon Plus Environment

Page 18 of 20

Page 19 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


393

Supercritical fluid extraction of bal 150 crude oil asphaltenes. Energ Fuel. 2000. 14, 89-94.

394

(49) Al-Marzouqi, A. H.; Zekri, A. Y.; Jobe, B.; Dowaidar, A. Supercritical fluid extraction for

395

the determination of optimum oil recovery conditions. J. Pet. Sci. Eng. 2007. 55, 37-47.

396

(50) Cao, X.; Peng, B.; Ma, S.; Ni, H.; Zhang, L.; Zhang, W.; Li, M.; Hsu, C.; Shi, Q.

397

Molecular Selectivity in Supercritical CO2 Extraction of a Crude Oil. Energ Fuel. 2017. 31,

398

4996-5002.

399



43x21mm (600 x 600 DPI)


Page 20 of 20

Study on the Asphaltene Precipitation in CO2 ... - ACS Publications

Recommend Documents