CO2 Adsorption of Nitrogen-Doped Carbons Prepared from Nitric Acid

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CO2 adsorption of nitrogen-doped carbons prepared from nitric acid pre-oxidized petroleum coke Jie Yang, Limin Yue, Binbin Lin, Linlin Wang, Yongle Zhao, Ying Lin, Kaijiao Chang, Herbert DaCosta, and Xin Hu Energy Fuels, Just Accepted Manuscript • DOI: 10.1021/acs.energyfuels.7b01795 • Publication Date (Web): 11 Sep 2017 Downloaded from http://pubs.acs.org on September 12, 2017

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CO2 adsorption of nitrogen-doped carbons prepared from nitric acid pre-oxidized petroleum coke Jie Yang a, Limin Yuea, Binbin Lina, Linlin Wangb, Yongle Zhao a, Ying Lina, Kaijiao Changa, Herbert DaCostac, Xin Hu*,a a

College of Chemistry and Life Sciences, Zhejiang Normal University, 688 Yingbin

Ave. Jinhua 321004, PR China b

College of Engineering, Zhejiang Normal University, 688 Yingbin Ave. Jinhua

321004, PR China c

Math, Science, and Engineering Division, Illinois Central College, 1 College Drive

East Peoria, IL 61635, USA *

Corresponding author’s e-mail: [email protected]; phone: 86-151-0579-0257; fax:

86-579-8228-8269

1

ACS Paragon Plus Environment

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Abstract Petroleum coke was pre-treated by HNO3 before urea modification and KOH activation to synthesize N-doped porous carbons. The as-synthesized samples were carefully characterized by various techniques. This series of samples demonstrate high CO2 uptake at 1 bar, up to 4.13 mmol/g at 25 °C and 6.24 mmol/g at 0 °C, respectively. In addition, these sorbents possess high CO2/N2 selectivity, stable reusability, moderate heat of CO2 adsorption, and high dynamic CO2 capture capacity under simulated flue gas conditions. Further comparison shows that sorbents synthesized by HNO3 pretreatment possess higher nitrogen content and narrow microporosity than the control sample without HNO3 pretreatment, but a lower CO2 uptake. Additional investigations show that, in addition to nitrogen content and narrow micropores, the size of narrow micropores, the narrow micropore size distributions, surface acidity, and the content of specific N and O species on the surface of the N-doped porous carbons also play major roles in determining the CO2 capture capacity under ambient condition. This work is intended to provide useful information and to inspire ways to develop new carbonaceous sorbents for removing CO2 from combustion flue gas. Keywords: CO2 adsorption, nitrogen-doped, porous carbons, petroleum coke, nitric acid pre-oxidized

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1. Introduction Climate change has become a global issue1. Over 100 nations joined the Paris Climate Agreement, which officially came to effect on November 04, 2016. This Agreement intends to hold the rise of global average temperature below 2 °C above pre-industrial levels, but it hopes to keep the rise under 1.5 °C2. It is well accepted that CO2 emission causes global warming, thus efforts need to be made to reduce the emission of CO2 into the atmosphere3. Among the different approaches and technologies to mitigate CO2 emission, CO2 capture using solid adsorbents is a promising alternative4-7. The merits of the adsorption process include low energy consumption for sorbent regeneration, easy sorbent preparation, simplicity of operation, and low capital investment costs8-10. The key to this technology is to synthesize adsorbents with the following properties: (1) high CO2 adsorption capacity, (2) high CO2/N2 selectivity, (3) moderate CO2 heat of adsorption, (4) fast adsorption/desorption kinetics, and (5) excellent chemical and mechanical stability. Various porous materials such as carbons11-21, zeolite22, 23, metal organic frameworks24, 25

(MOF), and porous polymers26,

27

have been extensively investigated as CO2

adsorbents. Of these sorbents, porous carbons have shown great promise in CO2 adsorption and separation applications28,

29

. Some advantages of porous carbons

include low production cost, wide availability, simple synthesis, easy surface functionalization, easy-to-design pore structure, easy to regenerate, chemical and moisture inertness, and high stability11, 30, 31. Previous studies have revealed that the amount of narrow micropores (N-5>N-Q for these carbons. Figure S1 summarizes the quantitative evaluation of different nitrogen species on the surface of selected samples. 3.2 Phase Structure and Surface Morphology Morphology of P, HP, HNP and HNP-650-3 observed by SEM are shown in Figure 2. P , HP and HNP show the similar bulky morphology indicating that surface modification by HNO3 or urea brought little change in the surface morphology. After KOH activation, the surface of HNP-650-3 shows some irregular and heterogeneous types of macropores, as illustrated in Figure 2d. The detailed pore and phase structures of HNP-650-3 were further studied with XRD and TEM techniques. XRD pattern of HNP-650-3 shows two broad and weak diffraction peaks at 2θ of 24 and 43°, which are indexed to (002) and (100) diffractions of amorphous carbon47, respectively (Figure S3). TEM image (Figure S4) clearly illustrates worm-like micropores formed by stacking curved graphene layers in HNP-650-3, confirming its amorphous nature.

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3.3 Porous Properties The porous properties of as-synthesized carbons were characterized by N2 sorption at -196°C and CO2 sorption at 0 °C. Figs. 3 show the nitrogen adsorption/desorption isotherms at -196 °C for nitrogen-doped porous carbons synthesized under different conditions. The textural characterization results are included in Table 1. All of the isotherms display type I curves with 90% N2 adsorption capacity at a very low relative pressure (P/P0 0.1, the isotherm demonstrates an almost flat sorption feature. Additionally, there are almost no hysteresis loops in the isotherms in the entire P/P0 range. These findings obviously suggest the lack of mesoporosity in the prepared carbons. From table 1, the value of each textural characteristic increases with the increase of KOH/precursor ratio or activation temperature with only one exception. The BET surface area (SBET), total pore volume (V0) and micropore pore volume (Vt) of this series of carbons range from 1394 to 2532 m2/g, 0.58-1.40 cm3/g and 0.52-1.21 cm3/g, respectively. The CO2 adsorption data achieved at 0 °C were applied to determine the narrow microporosity using the Dubinin−Radushkevich (D−R) equation. The value of narrow micropore (Vn) is in the range of 0.59-0.92 cm3/g for these carbons. It is found that for the samples prepared with KOH/precursor ratio of 2, Vn is higher than Vt. On the contrary, for the samples prepared under higher KOH/precursor ratio, Vn is lower than Vt. HNP-700-4 shows the biggest difference between Vn and Vt among all the samples. This indicates that

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the harsh activation condition is detrimental to developing narrow micropores, which is responsible for CO2 adsorption under ambient condition11, 12. It is important to point out that the value of each textural characteristic of HNP-650-3 is higher than the control sample NP-650-3 including the value of Vn, suggesting the positive effect of HNO3 pretreatment on increasing the narrow microporosity of the carbons. 3.4 CO2 Adsorption properties CO2 adsorption isotherms are achieved at 1 bar, at 25 °C and 0 °C, respectively (Fig. 4). The carbonaceous sorbents synthesized in this study exhibited good CO2 adsorption capacities in the range of 3.22 to 4.13 mmol/g at 25 °C and 5.05 to 6.24 mmol/g at 0 °C under atmospheric pressure. Among all the samples, HNP-650-3 possesses the highest CO2 adsorption capacity of 4.13 mmol/g at 25 °C. This value is comparable to some known N-doped porous carbons37, 48-50 and higher than many other microporous sorbents such as zeolites23, MOFs25, 51, COFs52 and PAFs53, 54 at the same condition. However, it should be noted that there is still a large gap between this value and the 5.4 mmol/g reported by Sayari and co-workers for a high N-containing porous carbon28. Correlation between CO2 adsorption capacity and N content as well as each porous properties characteristics (i.e. SBET, V0, Vt , Vn) were shown in Figure S5. Obviously, CO2 adsorption capacity for these samples does not show any proper correlation with SBET, V0, Vt , Vn or the nitrogen content. The maximum CO2 adsorption capacity was found in HNP-650-3, which has the second-highest Vn and moderate N content of all sorbents. On the other hand, HNP-600-2 with highest nitrogen content but relatively low Vn and HNP-700-3 with the highest Vn but

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second-lowest nitrogen content show much lower CO2 uptake than HNP-650-3. These results indicate the synergetic effect of narrow micropores and nitrogen content on the CO2 adsorption capacity of this series of samples. When comparing HNP-650-3 with the control sample NP-650-3, it was surprising to find that HNP-650-3 showed a lower CO2 adsorption capacity than NP-650-3, although the former has higher Vn and nitrogen content than the latter. In most references, nitrogen content and narrow porosity are considered as the only major factors that determines the CO2 uptake under ambient condition16, 18, 19, 32-35. Our results hint that there are other factors that also play key roles in CO2 uptake under ambient condition. We explain this unusual phenomenon in terms of three factors. In the first one, the pore size distribution of HNP-650-3 and NP-650-3 were determined by the density functional theory (DFT) method using N2 adsorption data, as shown in Figure 5. From this figure, HNP-650-3 shows the larger pore size together with broader pore size distributions than NP-650-3, which may account for its lower CO2 adsorption capacity. In the second factor, surface properties of both samples were examined by titration with NaOH and HCl to determine their total surface acidity and basicity55. The detailed titration method can be found in the supporting information and the results are shown in Table 2. From the results, it can be observed that HNP-650-3 has a higher total basicity than NP-650-3, possibly due to the fact that HNP-650-3 has more basic nitrogen functionalities on its surface. However, at the same time, HNP-650-3 possesses a higher total acidity than NP-650-3, which is believed to be ascribed to the extra oxygen functionalities inherited from the

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HNO3 pretreatment. Hence, we propose that the higher surface acidity of HNP-650-3 compared to NP-650-3 possibly leads to its lower CO2 uptake. As the third factor, we carefully examined the N1s XPS results of HNP-650-3 and NP-650-3 (Figure 6), and found that the amount of N-6 is higher than N-5 for HNP-650-3, but for NP-650-3, N-5 species is the main component of the nitrogen functionalities, as presented in Table S1. The higher ratio of N-5 in NP-650-3 could be favorable to CO2 capture, since it has been reported that in general, N-5 contributes more significantly to CO2 capture than N-6 and N-Q types of nitrogen species32, 56. Other than the nitrogen species, XPS was also employed to investigate the number and type of the oxygen functional groups presented on the surface of HNP-650-3 and NP-650-3. Figure S6 shows XPS survey-scan spectra for the two samples, respectively. The quantitative analysis shows that the surface oxygen contents obtained from XPS measurements are 22.3% for HNP-650-3 and 19.6 % for NP-650-3, which are somewhat higher than the amounts of bulk oxygen obtained from elemental analysis. The XPS O1s spectra of HNP-650-3 and NP-650-3 were shown in Figure S7. The O1s spectrum can be deconvoluted into two peaks with the binding energies centered at 531 and 532.9 eV for the above samples. These peaks can be assigned to ester or ether (C-O) and hydroxyl groups (C-OH)57, respectively. The quantitative evaluation of different oxygen species on the surface of two samples was summarized in Table S2. From the quantitative analysis, NP-650-3 has higher ratio of C-OH than HNP-650-3. In a previous study, it has shown that hydrogen bonds between CO2 and the surface of carbon sorbent can be formed due to the high electronegativity of the oxygen atom in

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the CO2 molecule48. The higher ratio of C-OH on the surface of NP-650-3 leads to the higher possibility of the formation of typical hydrogen bond O-H…O, which may also account for its higher CO2 uptake than HNP-650-3. The above three factors may explain why a sample with higher nitrogen content and narrow micropores show lower CO2 uptake under ambient condition. Albeit empirical, we hope that this can provide insights to help further improving the CO2 adsorption capacities of N-doped porous carbons. Very rigorous analysis will be needed to clarify the roles of these factors on CO2 capture and relationship among these factors in the future work. For complete characterization of this series of samples, the isosteric heat of adsorption (Qst), CO2 over N2 selectivity, cyclic stability towards CO2 adsorption, and dynamic CO2 capture capacity from N2/CO2 gas mixtures were carefully investigated and discussed. The isosteric heat of adsorption (Qst) on different carbon materials was calculated from the CO2 adsorption isotherms at 25 °C and 0 °C using the Clausius–Clapeyron equation58, 59. The Qst value in the initial adsorption stage (low CO2 loading) for the studied carbons is found to be between 24–35 kJ mol-1 (Figure 7a). These values are still in the range of physisorption process. Generally, a high Qst value is beneficial for flue gas separation, because a high CO2 adsorption capacity at low pressures is needed, but a too high Qst would lead to difficulty in the regeneration of sorbents. This moderate Qst is favorable from the viewpoint of potential applications. In addition, as a result of the surface heterogeneity, the Qst value decreases with the increase in the amount of the CO2 adsorbed.

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The CO2 over N2 selectivity of HNP-650-3 was determined according to independent N2 and CO2 adsorption isotherms (Figure 7b). Based on the ideal adsorption solution theory (IAST)60, the CO2/N2 selectivity of HNP-650-3 was 14 for the gas mixtures (CO2 : N2 = 0.10 : 0.90) at 25 °C, indicating its potential in post-combustion CO2 capture. In order to test recyclability and stability, the sample HNP-650-3 was submitted to five repeated adsorption/desorption cyclic test at 25 °C (Figure 7c). The results showed only 0.2% loss after five successive adsorption/desorption runs, indicating the high potential for multiple-time use in CO2 capture processes. Finally, the sorbent was evaluated under dynamic conditions to find out the extent of equilibrium adsorption capacity converted into breakthrough capacity. The dynamic CO2 capture capacity of HNP-650-3 was characterized using a dynamic setup. From the breakthrough curves shown in Figure 7d, its dynamic CO2 capture capacity was calculated to be 0.86 mmol/g from a CO2/N2 (10:90 v/v) gas mixture at 25 °C, proving its capability in capturing CO2 from flue gas. 4. Conclusion In summary, the role of HNO3 pretreatment on CO2 uptake of N-doped carbons was examined in this work. Petroleum coke was pre-oxidized by HNO3 before urea modification and KOH activation to synthesize N-doped porous carbons. This series of samples demonstrate high CO2 uptake at 1 bar, up to 4.13 mmol/g at 25 °C and 6.24 mmol/g at 0 °C, respectively. In addition, these sorbents possess high CO2/N2 selectivity, stable reusability, moderate heat of CO2 adsorption, and high dynamic CO2

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capture capacity under simulated flue gas conditions. Further comparison shows that sorbent pretreated by HNO3 possesses higher nitrogen content and narrow microporosity than the one without HNO3 pretreatment. However, the sample pretreated by acid (HNP-650-3) shows a lower CO2 uptake than the control sample without HNO3 pretreatment (NP-650-3). This seems to be contrary to the conclusion drawn from many previous reports. Further investigations showed that the larger narrow micropore size together with broader pore size distributions, higher surface acidity, and smaller ratio of N-5 species and C-OH group of HNP-650-3 than NP-650-3 can possible explain this phenomenon. This work indicates that various factors, in addition to nitrogen content and narrow micropores, may play major roles in determining the CO2 capture capacity under ambient condition. This work is intended to provide useful information and hence to inspire ways to develop new carbonaceous sorbents for removing CO2 from combustion flue gas. Acknowledgments Financial support from Zhejiang Provincial Natural Science Foundation (LY17E010002) and the NSF of China (21106136), and National Undergraduate Training Program for Innovation and Entrepreneurship of China (201510345015). Supporting Information: Schematic diagram of the CO2 capture system, XRD patterns, FT-IR spectrum, TEM image, the plots of each porous properties characteristics and nitrogen content versus CO2 uptake, XPS survey-scan spectra and XPS O 1s spectra for HNP-650-3 and NP-650-3. This material is available free of charge via the internet at

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Table 1. Porous properties, elemental compositions and CO2 uptakes of sorbents derived from petroleum coke under different conditions Sample

V0 b Vt c Vn d SBETa N (wt%) C (wt%) H (wt%) (m2/g) (cm3/g) (cm3/g) (cm3/g)

O (wt%)e

CO2 uptake (mmol/g) 25°C 0.36 0.56 0.55 0.86 3.56 3.95 3.29 3.98 4.13 3.28 3.82 3.49 3.22 4.26

P 0.43 0.01 0.12 0.20 80.90 3.92 14.98 HP 0.10 4.06 76.07 2.78 17.09 NP 2.37 0.04 0.09 9.16 73.21 2.53 15.10 HNP 0.13 0.11 11.08 75.39 2.43 11.10 HNP-600-2 1479 0.60 0.53 0.61 3.25 75.58 1.45 19.72 HNP-600-3 1699 0.74 0.66 0.72 2.68 75.21 1.37 20.74 0.85 0.77 0.76 1.70 75.98 1.40 20.92 HNP-600-4 1888 HNP-650-2 1394 0.58 0.52 0.71 2.79 75.61 1.32 20.28 HNP-650-3 2363 1.00 0.96 0.88 1.61 75.74 1.24 21.41 HNP-650-4 2526 1.25 1.10 0.84 1.41 78.35 1.12 19.12 HNP-700-2 1703 0.84 0.66 0.74 2.18 80.48 0.88 16.46 HNP-700-3 2423 1.10 1.05 0.92 1.34 80.54 0.90 17.22 HNP-700-4 2532 1.40 1.21 0.59 1.20 81.04 0.95 16.81 NP-650-3 1755 0.73 0.64 0.75 0.81 80.60 1.53 17.06 a Surface area was calculated using the BET method at P/P0=0.005-0.05. b Total pore volume at P/P0 = 0.99. c Evaluated by the t-plot method. d Pore volume of narrow micropores (

CO2 Adsorption of Nitrogen-Doped Carbons Prepared from Nitric Acid

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