Exploratory Study for the Mechanism of Surfactant Restraining the

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Exploratory Study for the Mechanism of Surfactant Restraining the Coke on the Surface of Reactor in Residue Slurry Phase Hydrocracking Min Cui, Chuan Li, Jiqian Wang, and Wenan Deng Energy Fuels, Just Accepted Manuscript • DOI: 10.1021/acs.energyfuels.6b00367 • Publication Date (Web): 31 Mar 2016 Downloaded from http://pubs.acs.org on April 11, 2016

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Exploratory Study for the Mechanism of Surfactant Restraining the Coke on the Surface of Reactor in Residue Slurry Phase Hydrocracking Min Cui1, Chuan Li*2, Jiqian Wang2, Wenan Deng2 1. College of Science, China University of Petroleum, Qingdao, Shandong 266580, PR China; 2. State Key Laboratory of Heavy Oil, China University of Petroleum, Qingdao, Shandong 266580, PR China Chuan

Li,

E-mail:

[email protected],

[email protected];

Min

Cui,

E-mail:

[email protected]

Abstract: The product distributions in slurry phase hydrocracking of a kind of heavy oil (AR from Venezuela, VAR) with 4 kinds of surfactants (cetyl trimethyl ammonium bromide (CTAB), sodium dodecyl benzene sulfonate (SDBS), twelve alkyl two methyl betaine (TATMB) and OP-10 (OP)) were studied to select the best surfactant restraining the coke on the surface of reactor (CokeS). In order to understand the action mechanism of surfactant, the asphaltene surface functional groups were analyzed, and the catalyst’s average diameter, system’s colloidal stability parameter (CSP) and asphaltene’s adsorption performance on metal surface were measured also. Results indicated that CTAB could reduce CokeS from 1.6 wt% to 0.4 wt%, while SDBS increased CokeS, and TATMB and OP almost does not affect CokeS. Only the change regulation of asphaltene’s adsorption performance and CokeS was consistent with different surfactants, which implied the asphaltene’s adsorptivity on metal surface should be the critical factor controlling CokeS. The study showed the asphaltene of VAR was acidic, so CTAB with the weak basic amino-group could react with VAR asphaltene, thereby restraining the adsorptivity of asphaltene on the surface of reactor, which caused 1

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the decrease of CokeS. The mechanism of surfactant decreasing CokeS was proposed that the surfactant with the opposite functional group compared with the acidity or basicity of asphaltene can react with asphaltene through acid-base action to restrain the adsorptivity of asphaltene on the surface of reactor resulting in the reduce of CokeS. Key words: mechanism; surfactant; coke on the surface of reactor; adsorption performance of asphaltene; residue slurry phase hydrocracking 1. Introduction Residue Slurry phase hydrocracking is a heavy oil processing technology,

1-3

which has the

advantages of good adaptability of raw materials with poor quality, high conversion and high residual carbon removal rate. 4 Much efforts about catalyst, 5-8 technology 9-11 and reaction 12-14 have been made towards industrializing this technology. Nevertheless, coking, especially coking on the reactor surface, which can block up the pipeline and shorten the run period of equipments, is the bottleneck of industrialization.

15, 16

Therefore how to restrain the coke formation on the reactor

surface is very important to develop the technology of slurry phase hydrocracking. Coking on the reactor surface is a complex physical and chemical process. Asphaltene molecules begin cracking and condensation reactions at high temperature. When the hydrogenation rate is less than the dehydrogenation rate, the condensation reaction becomes the dominant reaction, and the difference of polarity between asphaltene and other fractions becomes bigger and bigger, leading to the liquid-liquid phase separation, forming the second liquid phase, a part of which is adsorbed on the hot metal surface and continues dehydrogenation and condensation reactions to produce coke on the reactor surface. the reactor surface effectively,

17, 18

19, 20

Although some surfactants can decrease the coke yield on

and lots of investigations about the interaction between

surfactants and asphaltene have been done,

21-29

but the mechanism of surfactant reducing the coke

on the surface of reactor (CokeS) is still not clear, resulting in the suitable surfactant can not be 2


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chosen on the basis of characteristics of raw oil. Recently, Li

30

found sodium dodecyl benzene

sulfonate(SDBS) could decrease CokeS in slurry phase hydrocracking of Karamay AR by reducing the asphaltene’s adsorptivity on the surface of reactor. However, this conclusion was obtained by only one kind of heavy oil, which was not confirmed through other raw oils. Hence, a related research about another kind of heavy oil with different surface functional groups of asphaltene would be necessary. In view of coking process, the surfactant may affect CokeS from three ways: 1. strengthening the hydrogenation ability of catalyst to reach a lower total coke yield; 2. making the system more stable to delay the forming of the second liquid phase; 3. reducing the asphaltene’s adsorptivity on metal surface to decrease CokeS. This investigation will study the effects of different surfactants on catalyst’s average diameter, system’s colloidal stability parameter and asphaltene’s adsorption performance to confirm the mechanism of surfactant reducing CokeS in residue slurry phase hydrocracking. 2. Experimental section 2.1. Feedstock and additives The feed oil used in this work was an inferior atmospheric residue from Venezuela (VAR) with poor qualities (Table 1), which was difficult to effectively process by now, and the catalyst precursor was the mixture of molybdenum naphthenate and nickel naphthenate, in which the mass ratio of Mo/Ni was 3:2. Literatures reported only the surfactant with straight chain number of 6~16 can interact with asphaltene efficaciously,

26, 30

so 4 kinds of adequate surfactants were selected in this

study, which were cationic surfactant (cetyl trimethyl ammonium bromide (CTAB, C19H42BrN)), anionic surfactant (sodium dodecyl benzene sulfonate (SDBS, C18H29NaO3S)), amphoteric surfactant (twelve alkyl two methyl betaine (TATMB, C19H39NO2)) and non-ionic surfactant (OP-10 (OP, C24H60O)) respectively. 3


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Table 1. Properties of VAR Properties

VAR

Density, 20℃, g·cm-3

0.9664

Viscosity, 50℃, mm2·s-1

300

C7-asphaltene, wt%

7.77

Conradson carbon residue (CCR), wt%

12.0

C, wt%

85.06

H, wt%

11.17

S, wt%

2.54

N, wt%

0.43

H/C atomic ratio

1.56

2.2. Experimental Equipment and Methods 2.2.1. Reactions The apparatus with a 0.5 L autoclave was used in this study. A schematic flow diagram is shown in Figure 1.

Figure 1. Experimental equipment: 1. Hydrogen cylinder, 2. Electric heater, 3. Autoclave, 4. High pressure agitator, 5. Speed and temperature controller, 6. Surge flask. The experimental raw material was 200g VAR, and the additives included catalyst precursor, 4


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sulfur and surfactant, the contents of which were 150 µg·g-1 (calculated by metal atoms), 400 µg·g-1 and 200 µg·g-1 severally. The reactions carried out in autoclave, and the reaction conditions were: stir speed, 800 rpm; temperature, 435 °C; H2 pressure, 12 MPa; reaction time, from 10 min to 60 min. After reaction, the autoclave was water-cooled, and the products were separated into 4 parts: TATMB>none>SDBS. Besides, surfactants could alter the proportion of CokeL and CokeS. The proportion of CokeS and CokeL was about 4.0 without any surfactant, and changed into 0.3, 10.0, 3.8 and 4.3, respectively, when adding CTAB, SDBS, TATMB and OP. That implied 8


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CTAB could reduce CokeS significantly (from 1.6 wt% to 0.4 wt%), and SDBS could increase CokeS (from 1.6 wt% to 2.0 wt%), which was different compared with the situation when the raw oil was KAR,

30

while TATMB decreased CokeS and OP increased CokeS slightly. Then the sequence of

reducing CokeS was CTAB>TATMB≈none≈OP>SDBS, and CTAB was the best surfactant to reduce CokeS.

3.2. Average diameter of catalyst and CSP value of system . Figure 4 shows the changes of average diameter of catalyst using different surfactants. In theory, the catalyst with smaller mean particle diameter would show better hydrogenation activity during slurry phase hydrocracking,

32

but as could be seen form Figure 4, the reduction sequence of

catalyst’s average diameter was OP>TATMB>CTAB>none>SDBS, which didn’t agree with the sequence of decreasing CokeS. Therefore, the influence of surfactant on catalyst is not the critical factor restraining CokeS apparently. 0

2

4

6

8

10 10

8

Average diameter of catalyst, µm

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

Energy & Fuels

8 6 6

4 4

2

0

2

1

none

2

CTAB

3

4

TATMB SDBS Surfactant type

5

0

OP

Figure 4. Average diameters of catalyst with different surfactants The influences of surfactants on the system’s CSP value under different reaction time were shown in Figure 5. Increasing reaction time could decrease the CSP value, and the CSP value without any surfactant and adding SDBS reduced sharply after 30 min, implying the reaction system 9


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start forming coke rapidly. In contrast, the CSP value of system with CTAB, TATMB and OP reduced markedly after 40 min, which implied CTAB, TATMB and OP could enhance the system’s colloidal stability and prolong the coking inducing period except SDBS. The sequence of improving system’s colloidal stability was OP>CTAB>TATMB>none>SDBS, which was in accordance with the sequence of restraining the yield of total coke, but wasn’t consistent with the sequence of restraining CokeS. Hence, though the surfactant improving the system’s colloidal stability can accordingly restrain the yield of total coke, however is not the critical factor decreasing CokeS yet, which was in accord with the conclusion reported. 30 0 5.0

2

4

6

8

10 10

none CTAB SDBS TATMB OP

4.5

4.0

Value of CSP

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

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8

6

3.5

3.0

4

2.5 2 2.0

1.5

10

20

30

40

50

60

0

Reaction time, min

Figure 5. CSP values of system with different surfactants 3.3. Adsorption performance of asphaltene on sheet metal Figure 6 shows the asphaltene’s adsorption rates at different reaction time on sheet metal at the adsorbing time of 80 min. All of adsorption rates raised as the reaction time prolonging. The longer reaction time would increase the condensation degree and polarity of asphaltene which made asphaltene adsorb on sheet metal more easily. A break point of adsorption rate appeared at the reaction time of 40 min, which meant the reaction system trended to form coke obviously after reacting 40 min. In addition, the asphaltene’s adsorption rate could be affected by added surfactants, 10


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and the sequence of reduing asphaltene’s adsorption rate was CTAB>TATMB≈none≈OP>SDBS, agreeing with the sequence of restraining CokeS. 0 2.0

2

4

1.8

Adsorption rate, %

6

8

10 10


1.6 1.4

8

6

1.2 1.0 4 0.8 0.6

2

0.4 0.2

0

10

20

30

40

50

60

0

Reaction time, min

Figure 6. Asphaltene’s adsorption rates with surfactants at different reaction time Figure 7 shows the asphaltene’s adsorption rates at different adsorption time on sheet metal when reacting 60 min. All adsorption rates were improved as adsorption time prolonging, and the sequence of reducing adsorption rate was CTAB>TATMB≈none≈OP>SDBS, which also agreed with the sequence of restraining CokeS. 0 2.0 1.8 1.6 1.4

Adsorption rate, %

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2

4

6

8

10 10


8

6

1.2 1.0

4

0.8 0.6 0.4

2

0.2 0.0 0

20

40

60

Adsorption time, min 11


80

0

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Figure 7. Asphaltene’s adsorption rates with surfactants at different adsorption time In addition, the asphaltene’s adsorption rate raised linearly as the adsorption time increasing when adding surfacrants except CTAB. When CTAB was added, the upturn of adsorption rate was slowing down after adsorbing 20 min, which implied that the adsorption of asphaltene molecules on sheet metal might be in the way of single-molecule layer at the primary stage, and all surfactants showed no evident effect on this stage. When the asphaltene molecules continued to adsorb on sheet metal, an asphaltene’s multi-molecule layer would form. In this stage, SDBS, TATMB and OP seemed ineffectively to restrain forming asphaltene’s multi-molecule layer on sheet metal except CTAB. The inhibition of forming asphaltene’s multi-molecule layer on sheet metal by CTAB should be the reason of restraining asphaltene’s adsorption rate on sheet metal.

Table 3. Asphaltene’s adsorption rates with surfactants at different reaction time and adsorption time Adsorption rate at different adsorption time, % Surfactant

none

CTAB

SDBS

TATMB

Reaction time, min 0min

20min

40min

60min

0

0

0.12

0.25

0.40

20

0

0.19

0.37

0.60

40

0

0.32

0.59

0.85

0

0

0.10

0.21

0.27

20

0

0.16

0.30

0.37

40

0

0.28

0.44

0.50

0

0

0.15

0.30

0.45

20

0

0.21

0.43

0.66

40

0

0.35

0.63

0.93

0

0

0.11

0.23

0.37

12


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OP

20

0

0.17

0.35

0.57

40

0

0.30

0.56

0.81

0

0

0.14

0.28

0.43

20

0

0.21

0.40

0.62

40

0

0.35

0.63

0.87

As seen from Table 3, the results of asphaltene’s adsorption rate under other conditions were basically consistent to the results shown in Figure 6 and Figure 7. In this way, it can be concluded that the surfactant reducing the asphaltene’s adsorptivity on the surface of reactor is the critical factor restraining CokeS. The asphaltene’s XPS data could support the effectiveness of CTAB in this study. Figure 8 shows the VAR asphaltene’s XPS spectra, from which the types and contents of the functional groups of VAR asphaltene are obtained (Table 4). In VAR asphaltene, the C atoms in the form of C

—C and C—H accounted for dominant, reaching 89.62 mol% of all atoms. Among the O-containing groups, C=O was primary, in which the O atoms reached 1.15 mol% accounting for all atoms. In pyrrolic N and thiophenic S, the molar ratio of N atoms and S atoms were 0.96 mol% and 0.71 mol% accounting for all atoms severally. The three kinds of functional groups mentioned above were nearly neutral. The O atoms in COO were 0.70 mol% accounting for all elements which was considered as acidic functional group. Furthermore, the functional group of C-O (O atoms were 0.75 mol% accounting for all elements) might contain hydroxyl group and phenolic group, and the functional group of aliphatic S (sulfur atoms were 0.96 mol% accounting for all elements) might contain thiol group and phenyl-sulfhydryl group, which were all considered to be acidic. By comparison, the nitrogen atoms in pyridinic N were only 0.67 mol% accounting for all elements which was considered to be alkaline. Therefore, based on the analyses of XPS data, the VAR 13


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asphaltene should be weak acidic, with which CTAB could react by the weak basic amino-group in CTAB and thus prevented forming asphaltene’s multi-molecule layer. 50000

(a)

C1s

60000 50000

(b) 40000

O1s

Original peak

N1s 40000

30000

30000 20000

20000

Peak 1

Peak 2

S2p

10000

10000

Fitted peak

0 800

700

600

500

400

300

200

100

0

0 288

286

284

Binding energy, eV

282

280

Binding energy, eV

700

3500

(c)

Original peak

600

3000

(d)

Original peak

Peak 2

Peak 2 500

2500

2000

400

Peak 1

300

Peak 3

1500

Fitted peak

Fitted peak

1000

200

500

100

0 538

536

534

532

530

528

Peak 1

0 408

526

406

404

Binding energy, eV

402

400

398

396

394

392

Binding energy, eV

1200

(e)

Original peak

Peak 1

1000

800

Peak 2 600

Fitted peak 400

200

0 170

168

166

164

162

160

Binding energy, eV

Figure 8. VAR asphaltene’s XPS spectra: (a) Full survey spectrum; (b) C1s spectrum; (c) O1s spectrum; (d) N1s spectrum; (e) S2p spectrum

Table 4. VAR asphaltene’s XPS data Group type

Atom

Wa/ wt%

Aax/mol%

14


Cax/mol%

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C—C,C—H

C

95.24

89.62

84.13 C binding with O

C

4.76

4.48

C —O

O

28.96

0.75

C=O

O

44.23

1.15

COO

O

26.81

0.70

Pyridinic N

N

41.24

0.67

3.10

1.70 Pyrrolic N

N

58.76

0.96

Aliphatic S

S

57.29

0.96

42.71

0.71

3.97 Thiophenic S

S

So, the reason of CTAB reducing CokeS is that the CTAB with basic functional group and the acidic VAR asphaltene particle can interact with each other, reducing the asphaltene’s adsorptivity on the surface of reactor, which cause the decrease of CokeS. Associated with the reported conclusion that the SDBS with acidic functional group and the basic KAR asphaltene particle can interact to reduce the asphaltene’s adsorptivity on the surface of reactor to restrain CokeS,

30

the

mechanism of surfactant decreasing the coke on the surface of reactor can be obtained that the surfactant with the opposite functional group compared with the acidity or basicity of asphaltene can react with asphaltene through acid-base action to reduce the adsorptivity of asphaltene on the surface of reactor, which should be the critical factor of surfactant restraining CokeS. This process can be illustrated by Figure 9.

15


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Figure 9. Mechanism of surfactant restraining CokeS: (a) The reaction system with surfactant, (b) The reaction system with no surfactant; 1. The surfactant with the opposite functional group compared with the acidity or basicity of asphaltene, 2. Asphaltene particle, 3. Surface of reactor, 4. Coke.

4. Conclusion (1) In slurry phase hydrocracking of VAR, the surfactant with the function of strengthening system’s colloidal stability can reduce the yield of total coke, but can’t change the proportion of CokeL and CokeS, and CTAB is the best surfactant to reduce CokeS compared with SDBS, TATMB and OP. (2) The mechanism of surfactant decreasing the coke on the surface of reactor can be obtained that the surfactant with the opposite functional group compared with the acidity or basicity of asphaltene can react with asphaltene through acid-base action to reduce the asphaltene’s adsorptivity on the surface of reactor, which is the critical factor of surfactant restraining CokeS.

Acknowledgement This work was supported by National Natural Science Foundation Young Investigator Grant Program of China (No. 21106186) and the Fundamental Research Funds for the Central Universities ( No. 14CX05032A). 16


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(22) Chang C. L.; Fogler H. S. Stabilization of asphaltenes in aliphatic solvents using alkylbenzne-derived amphiphiles. 2. Study of the asphaltene-amphiphile interactions and structures using Fourier Transform Infrared Spectroscopy and Small -Angle X-ray Scattering techniques. Langmuir 1994, 10(6), 1758-1766. (23) Ramos A. C. S.; Haraguchi L.; Notrispe F. R.; Loh W.; Mohamed R. S. Interfacial and colloidal behavior of asphaltenes obtained from Brazilian crude oils. Journal of Petroleum Science and Engineering 2001, 32(2-4), 201-216. (24) León O.; Contreras E.; Rogel E.; Dambakli G.; Espidel J.; Acevedo S. The influence of the adsorption of amphiphiles and resins in controlling asphaltene flocculation. Energy & Fuels 2001, 15(5), 1028-1032. (25) Rogel E.; León O. Study of the adsorption of alkyl-benzene-derived amphiphiles on an asphaltene surface using molecular dynamics simulations. Energy & Fuels 2001, 15(5), 1077-1086. (26) Wiehe I. A.; Jermansen T. G. Design of synthetic dispersants for asphaltenes. Petroleum Science and Technology 2003, 21(3-4), 527-536. (27) Ibrahim H. H.; Idem R. O. Interrelationships between asphaltene precipitation inhibitor effectiveness, asphaltenes characteristics, and precipitation behavior during n-heptane (light paraffin hydrocarbon)-induced asphaltene precipitation. Energy & Fuels 2004, 18(4), 1038-1048. (28) Adams J. J. Asphaltene adsorption, a literature review. Energy & Fuels 2014, 28(5), 2831-2856. (29) Miao L.; Li F.; Sun D.; Wu T.; Li Y. Interfacial and electrokinetic properties of asphaltenes and alkali/surfactant/polymer in produced water system. Journal of Petroleum Science and Engineering 2015, 133, 18-28. (30) Li C.; Song J.; Wang X.; Deng W. Effect of sodium dodecyl benzenesulfonate on the coke formation during slurry-bed hydrocracking of an atmospheric residue from Karamay. Energy & Fuels 2015, 29(1), 52-57. 19


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