Recent advances on metal-free graphene-based catalysts for the production of industrial chemicals

doi:10.1007/s11705-018-1722-y

Front. Chem. Sci. Eng.

2018, Vol. 12

Issue (4) : 855-866 https://doi.org/10.1007/s11705-018-1722-y

REVIEW ARTICLE

Recent advances on metal-free graphene-based catalysts for the production of industrial chemicals

Zhiyong Wang^1,², Yuan Pu^1,², Dan Wang^1,²(

), Jie-Xin Wang^1,², Jian-Feng Chen^1,²

¹. Beijing Advanced Innovation Center for Soft Matter Science and Engineering, State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China
². Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

Download: PDF(373 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract

With the development of carbon catalysts, graphene-based metal-free catalysts have drawn increasing attention in both scientific research and in industrial chemical production processes. In recent years, the catalytic activities of metal-free catalysts have significantly improved and they have become promising alternatives to traditional metal-based catalysts. The use of metal-free catalysts greatly improves the sustainability of chemical processes. In view of this, the recent progress in the preparation of graphene-based metal-free catalysts along with their applications in catalytic oxidation, reduction and coupling reactions are summarized in this review. The future trends and challenges for the design of graphene-based materials for industrial organic catalytic reactions with good stabilities and high catalytic performance are also discussed.

Keywords graphene-based materials metal-free catalyst industrial chemical productions catalytic reaction

Corresponding Author(s): Dan Wang

Just Accepted Date: 05 March 2018 Online First Date: 12 June 2018 Issue Date: 03 January 2019

Cite this article:

Zhiyong Wang,Yuan Pu,Dan Wang, et al. Recent advances on metal-free graphene-based catalysts for the production of industrial chemicals[J]. Front. Chem. Sci. Eng., 2018, 12(4): 855-866.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-018-1722-y
https://academic.hep.com.cn/fcse/EN/Y2018/V12/I4/855

Fig.1 Structure diagram of (a) GO and (b) rGO

Fig.2 Schematic diagram of active sites of graphene derivatives

Fig.3 Scheme 1Oxidation of benzene using CCG as catalyst [⁷⁴]

Fig.4 (a) EPR spectra of PMS activation under different conditions (♥: DMPO-OH, ♦: DMPO-SO₄); (b) radical evolution during the PMS activation on SNG (catalyst: 0.2 g?L⁻¹; PMS: 6.5 × 10⁻³ mol?L⁻¹; phenol: 20 mg?L⁻¹; T: 25 °C; DMPO: 0.08 mol?L⁻¹) [⁷⁶]

Fig.5 Scheme 2Selective oxidative dehydrogenation of ethylbenzene to the styrene [⁷⁸]

Fig.6 Catalytic performance of different carbon materials during the oxidative dehydrogenation of EB, after 30 h on stream. Reaction conditions: 50 mg of the catalyst, 3% EB with He balance, O₂-EB= 1, total flow rate= 10 mL?min⁻¹, T = 400 °C [⁷⁸]

Tab.1 Graphene-based materials used in oxidation catalytic reactions

Fig.7 Scheme 3The reaction mechanism for the reduction of 4-NP to 4-AP catalyzed by SG metal-free catalyst [⁸⁵]

Tab.2 Graphene-based materials in reduction catalytic reactions

Fig.8 Scheme 4GO-catalyzed Friedel-crafts alkylation of arenes with alcohols [⁹²]

Fig.9 Scheme 5Michael addition catalyzed by GO-DETA [⁹⁴]

Fig.10 Scheme 6Oxidation of benzylamine to N-benzylidene benzylamine [⁹⁵]

Tab.3 Graphene-based materials in other catalytic reactions

1	A DChowdhury, KHouben, G TWhiting, S HChung, MBaldus, B MWeckhuysen. Electrophilic aromatic substitution over zeolites generates Wheland-type reaction intermediates. Nature Catalysis, 2017, 1(1): 23–31 https://doi.org/10.1038/s41929-017-0002-4
2	MHasany, M Malakootikhah, VRahmanian, SYaghmaei. Effect of hydrogen combustion reaction on the dehydrogenation of ethane in a fixed-bed catalytic membrane reactor. Chinese Journal of Chemical Engineering, 2015, 23(8): 1316–1325 https://doi.org/10.1016/j.cjche.2015.05.006
3	A BKoven, S S Tong, R R Farnood, C Q Jia. Alkali-thermal gasification and hydrogen generation potential of biomass. Frontiers of Chemical Science and Engineering, 2017, 11(3): 369–378 https://doi.org/10.1007/s11705-017-1662-y
4	CTan, X Cao, X JWu, QHe, J Yang, XZhang, JChen, W Zhao, SHan, G HNam, MSindoro, HZhang. Recent advances in ultrathin two-dimensional nanomaterials. Chemical Reviews, 2017, 117(9): 6225–6331 https://doi.org/10.1021/acs.chemrev.6b00558
5	VGeorgakilas, J A Perman, J Tucek, RZboril. Broad family of carbon nanoallotropes: Classification, chemistry, and applications of fullerenes, carbon dots, nanotubes, graphene, nanodiamonds, and combined superstructures. Chemical Reviews, 2015, 115(11): 4744–4822 https://doi.org/10.1021/cr500304f
6	MYe, Z Zhang, YZhao, LQu. Graphene platforms for smart energy generation and storage. Joule, 2018, 2(2): 1–24 https://doi.org/10.1016/j.joule.2017.11.011
7	DWang, L Zhu, J FChen, LDai. Can graphene quantum dots cause DNA damage in cells? Nanoscale, 2015, 7(21): 9894–9901 https://doi.org/10.1039/C5NR01734C
8	HTao, Y Gao, NTalreja, FGuo, J Texter, CYan, ZSun. Two-dimensional nanosheets for electrocatalysis in energy generation and conversion. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2017, 5(16): 7257–7284 https://doi.org/10.1039/C7TA00075H
9	ESalehi, F Soroush, MMomeni, ABarati, AKhakpour. Chitosan/polyethylene glycol impregnated activated carbons: Synthesis, characterization and adsorption performance. Frontiers of Chemical Science and Engineering, 2017, 11(4): 575–585 https://doi.org/10.1007/s11705-017-1650-2
10	ZXiang, D Wang, YXue, LDai, J F Chen, D Cao. PAF-derived nitrogen-doped 3D carbon materials for efficient energy conversion and storage. Scientific Reports, 2015, 5(1): 8307–8314 https://doi.org/10.1038/srep08307
11	XLiu, L Dai. Carbon-based metal-free catalysts. Nature Reviews Materials, 2016, 1(11): 16064–16075 https://doi.org/10.1038/natrevmats.2016.64
12	D SSu, G Wen, SWu, FPeng, R Schlögl. Carbocatalysis in liquid-phase reactions. Angewandte Chemie International Edition, 2017, 56(4): 936–964 https://doi.org/10.1002/anie.201600906
13	DWang, Z Wang, QZhan, YPu, J X Wang, N R Foster, L Dai. Facile and scalable preparation of fluorescent carbon dots for multifunctional applications. Engineering, 2017, 3(3): 402–408 https://doi.org/10.1016/J.ENG.2017.03.014
14	GLv, H Wang, YYang, TDeng, C Chen, YZhu, XHou. Graphene oxide: A convenient metal-free carbocatalyst for facilitating aerobic oxidation of 5-hydroxymethylfurfural into 2,5-diformylfuran. ACS Catalysis, 2015, 5(8): 5636–5646 https://doi.org/10.1021/acscatal.5b01446
15	SWang, Y Li, XFan, FZhang, GZhang. β-Cyclodextrin functionalized graphene oxide: An efficient and recyclable adsorbent for the removal of dye pollutants. Frontiers of Chemical Science and Engineering, 2015, 9(1): 77–83 https://doi.org/10.1007/s11705-014-1450-x
16	ZLiu, W Wang, XJu, RXie, L Chu. Graphene-based membranes for molecular and ionic separations in aqueous environments. Chinese Journal of Chemical Engineering, 2017, 25(11): 1598–1605 https://doi.org/10.1016/j.cjche.2017.05.008
17	X KKong, C L Chen, Q W Chen. Doped graphene for metal-free catalysis. Chemical Society Reviews, 2014, 43(8): 2841–2857 https://doi.org/10.1039/C3CS60401B
18	DDeng, K S Novoselov, Q Fu, NZheng, ZTian, X Bao. Catalysis with two-dimensional materials and their heterostructures. Nature Nanotechnology, 2016, 11(3): 218–230 https://doi.org/10.1038/nnano.2015.340
19	LDai, Y Xue, LQu, H JChoi, J BBaek. Metal-free catalysts for oxygen reduction reaction. Chemical Reviews, 2015, 115(11): 4823–4892 https://doi.org/10.1021/cr5003563
20	S SShinde, C H Lee, A Sami, D HKim, S ULee, J HLee. Scalable 3-D carbon nitride sponge as an efficient metal-free bifunctional oxygen electrocatalyst for rechargeable Zn-Air batteries. ACS Nano, 2017, 11(1): 347–357 https://doi.org/10.1021/acsnano.6b05914
21	P YHuang, C S Ruiz-Vargas, A M van der Zande, W S Whitney, M P Levendorf, J W Kevek, S Garg, J SAlden, C JHustedt, YZhu, et al. Grains and grain boundaries in single-layer graphene atomic patchwork quilts. Nature, 2011, 469(7330): 389–392 https://doi.org/10.1038/nature09718
22	K SNovoselov, A KGeim, S VMorozov, DJiang, YZhang, S VDubonos, I VGrigorieva, A AFirsov. Electric field effect in atomically thin carbon films. Science, 2004, 306(5696): 666–669 https://doi.org/10.1126/science.1102896
23	PTang, G Hu, MLi, DMa. Graphene-based metal-free catalysts for catalytic reactions in the liquid phase. ACS Catalysis, 2016, 6(10): 6948–6958 https://doi.org/10.1021/acscatal.6b01668
24	YMa, Y Chen. Three-dimensional graphene networks: Synthesis, properties and applications. National Science Review, 2015, 2(1): 40–53 https://doi.org/10.1093/nsr/nwu072
25	KSenthilkumar, S R Prabakar, C Park, SJeong, M SLah, MPyo. Graphene oxide self-assembled with a cationic fullerene for high performance pseudo-capacitors. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2016, 4(5): 1663–1670 https://doi.org/10.1039/C5TA09929C
26	JKim, W K Sang, H Yun, B JKim. Impact of size control of graphene oxide nanosheets for enhancing electrical and mechanical properties of carbon nanotube-polymer composites. RSC Advances, 2017, 7(48): 30221–30228 https://doi.org/10.1039/C7RA04015F
27	AAmbrosetti, P L Silvestrelli. Adsorption of rare-gas atoms and water on graphite and graphene by van der waals-corrected density functional theory. Journal of Physical Chemistry C, 2017, 115(9): 3695–3702 https://doi.org/10.1021/jp110669p
28	TEsfandiyari, N Nasirizadeh, MDehghani, M HEhrampoosh. Graphene oxide based carbon composite as adsorbent for Hg removal: Preparation, characterization, kinetics and isotherm studies. Chinese Journal of Chemical Engineering, 2017, 25(9): 1170–1175 https://doi.org/10.1016/j.cjche.2017.02.006
29	RKato, S Minami, YKoga, MHasegawa. High growth rate chemical vapor deposition of graphene under low pressure by RF plasma assistance. Carbon, 2016, 96: 1008–1013 https://doi.org/10.1016/j.carbon.2015.10.061
30	SKim, Y Song, M JHeller. Seamless aqueous arc discharge process for producing graphitic carbon nanostructures. Carbon, 2017, 120: 83–88 https://doi.org/10.1016/j.carbon.2017.04.006
31	I MPatil, M Lokanathan, BKakade. Three dimensional nanocomposite of reduced graphene oxide and hexagonal boron nitride as an efficient metal-free catalyst for oxygen electroreduction. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2016, 4(12): 4506–4515 https://doi.org/10.1039/C6TA00525J
32	T VTam, S G Kang, K F Babu, E S Oh, S G Leeb, W M Choi. Synthesis of B-doped graphene quantum dots as metal-free electrocatalyst for oxygen reduction reaction. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2017, 5(21): 10537–10543 https://doi.org/10.1039/C7TA01485F
33	ALerf, H He, MForster, JKlinowski. Structure of graphite oxide revisited. Journal of Physical Chemistry B, 1998, 102(23): 4477–4482 https://doi.org/10.1021/jp9731821
34	D RHaag, H H Kung. Metal free graphene based catalysts: A review. Topics in Catalysis, 2014, 57(6-9): 762–773 https://doi.org/10.1007/s11244-013-0233-9
35	WTu, Y Zhou, ZZou. Versatile graphene-promoting photocatalytic performance of semiconductors: Basic principles, synthesis, solar energy conversion, and environmental applications. Advanced Functional Materials, 2013, 23(40): 4996–5008 https://doi.org/10.1002/adfm.201203547
36	PShao, J Tian, FYang, XDuan, S Gao, WShi, XLuo, F Cui, SLuo, SWang. Identification and regulation of active sites on nanodiamonds: Establishing a highly efficient catalytic system for oxidation of organic contaminants. Advanced Functional Materials, 2018, 28(13): 1705295–1705302 https://doi.org/10.1002/adfm.201705295
37	W SHummers Jr, R EOffeman. Preparation of graphitic oxide. Journal of the American Chemical Society, 1958, 80(6): 1339–1339 https://doi.org/10.1021/ja01539a017
38	JChen, Y Li, LHuang, CLi, G Shi. High-yield preparation of graphene oxide from small graphite flakes via an improved Hummers method with a simple purification process. Carbon, 2015, 81(1): 826–834 https://doi.org/10.1016/j.carbon.2014.10.033
39	JBai, H Sun, XYin, XYin, S Wang, A ECreamer, LXu, Z Qin, FHe, BGao. Oxygen-content-controllable graphene oxide from electron-beam-irradiated graphite: Synthesis, characterization, and removal of aqueous lead. ACS Applied Materials & Interfaces, 2016, 8(38): 25289–25296 (Pb(II) ) https://doi.org/10.1021/acsami.6b08059
40	Y JGao, G Hu, JZhong, Z JShi, Y SZhu, D SSu, J GWang, X HBao, DMa. Nitrogen-doped sp2-hybridized carbon as a superior catalyst for selective oxidation. Angewandte Chemie International Edition, 2013, 52(7): 2109–2113 https://doi.org/10.1002/anie.201207918
41	RKumar, R K Singh, A R Vaz, R Savu, S AMoshkalev. Self-assembled and one-step synthesis of interconnected 3D network of Fe3O4/reduced graphene oxide nanosheets hybrid for high performance supercapacitor electrode. ACS Applied Materials & Interfaces, 2017, 9(10): 8880–8890 https://doi.org/10.1021/acsami.6b14704
42	GHu, C Xu, ZSun, SWang, H M Cheng, F Li, WRen. 3D graphene-foam-reduced-graphene-oxide hybrid nested hierarchical networks for high-performance Li-S batteries. Advanced Materials, 2016, 28(8): 1603–1609 https://doi.org/10.1002/adma.201504765
43	XMu, B Yuan, XFeng, SQiu, L Song, YHu. The effect of doped heteroatoms (nitrogen, boron, phosphorus) on inhibition thermal oxidation of reduced graphene oxide. RSC Advances, 2016, 6(107): 105021–105029 https://doi.org/10.1039/C6RA21329D
44	M HAunkor, I M Mahbubul, R Saidurb, H CMetselaar. The green reduction of graphene oxide. RSC Advances, 2016, 6(33): 27807–27828 https://doi.org/10.1039/C6RA03189G
45	NSykam, G M Rao. Room temperature synthesis of reduced graphene oxide nanosheets as anode material for supercapacitors. Materials Letters, 2014, 204: 169–172 https://doi.org/10.1016/j.matlet.2017.05.114
46	X KKong, Z Sun, MChen, CChen, Q W Chen. Metal-free catalytic reduction of 4-nitrophenol to 4-aminophenol by N-doped graphene. Energy & Environmental Science, 2013, 6(11): 3260–3266 https://doi.org/10.1039/c3ee40918j
47	KXu, Y Fu, YZhou, FHennersdorf, PMachata, IVincon, J JWeigand, A APopov, RBerger, XFeng. Cationic nitrogen-doped helical nanographenes. Angewandte Chemie International Edition, 2017, 56(50): 15876–15881 https://doi.org/10.1002/anie.201707714
48	HTao, C Yan, A WRobertson, YGao, J Ding, YZhang, TMaa, Z Sun. N-doping of graphene oxide at low temperature for the oxygen reduction reaction. Chemical Communications, 2017, 53(5): 873–876 https://doi.org/10.1039/C6CC08776K
49	XWang, G Sun, PRouth, D HKim, WHuang, PChen. Heteroatom-doped graphene materials: Syntheses, properties and applications. Chemical Society Reviews, 2014, 43(20): 7067–7098 https://doi.org/10.1039/C4CS00141A
50	DWei, Y Liu, YWang, HZhang, LHuang, GYu. Synthesis of N-doped graphene by chemical vapor deposition and its electrical properties. Nano Letters, 2009, 9(5): 1752–1758 https://doi.org/10.1021/nl803279t
51	T VVineesh, M P Kumar, C Takahashi, GKalita, SAlwarappan, D KPattanayak, T NNarayanan. Bifunctional electrocatalytic activity of boron-doped graphene derived from boron carbide. Advanced Energy Materials, 2015, 5(17): 1500658–1500665 https://doi.org/10.1002/aenm.201500658
52	L KPutri, B J Ng, W J Ong, H W Lee, W S Chang, S P Chai. Heteroatom nitrogen- and boron-doping as a facile strategy to improve photocatalytic activity of standalone reduced graphene oxide in hydrogen evolution. ACS Applied Materials & Interfaces, 2017, 9(5): 4558–4569 https://doi.org/10.1021/acsami.6b12060
53	YFang, X Wang. Metal-free boron-containing heterogeneous catalysts. Angewandte Chemie International Edition, 2017, 56(49): 15506–15518 https://doi.org/10.1002/anie.201707824
54	CYu, Z Liu, XMeng, BLu, D Cui, JQiu. Nitrogen and phosphorus dual-doped graphene as a metal-free high-efficiency electrocatalyst for triiodide reduction. Nanoscale, 2016, 8(40): 17458–17464 https://doi.org/10.1039/C6NR00839A
55	JXu, J Shui, JWang, MWang, H K Liu, S X Dou, I Y Jeon, J M Seo, J B Baek, L Dai. Sulfur graphene nanostructured cathodes via ball-milling for highperformance lithium sulfur batteries. ACS Nano, 2014, 8(10): 10920–10930 https://doi.org/10.1021/nn5047585
56	JXu, I Y Jeon, J M Seo, S Dou, LDai, J BBaek. Edge-selectively halogenated graphene nanoplatelets (XGnPs, X= Cl, Br, or I) prepared by ball-milling and used as anode materials for lithium-ion batteries. Advanced Materials, 2014, 26(43): 7317–7323 https://doi.org/10.1002/adma.201402987
57	JXu, J Ma, QFan, SGuo, S Dou. Recent progress in the design of advanced cathode materials and battery models for high-performance lithium-X (X= O2, S, Se, Te, I2, Br2) batteries. Advanced Materials, 2017, 29(28): 1606454–1606473 https://doi.org/10.1002/adma.201606454
58	ZXiang, D Cao, LHuang, JShui, M Wang, LDai. Nitrogen-doped holey graphitic carbon from 2D covalent organic polymers for oxygen reduction. Advanced Materials, 2014, 26(2): 3315–3320 https://doi.org/10.1002/adma.201306328
59	JZhang, L Dai. Nitrogen, phosphorus, and fluorine tri-doped graphene as a multifunctional catalyst for self-powered electrochemical water splitting. Angewandte Chemie International Edition, 2016, 55(42): 13296–13300 https://doi.org/10.1002/anie.201607405
60	RDu, Q Zhao, NZhang, JZhang. Macroscopic carbon nanotube-based 3D monoliths. Small, 2015, 11(27): 3263–3289 https://doi.org/10.1002/smll.201403170
61	M AWorsley, S Charnvanichborikarn, EMontalvo, S JShin, E DTylski, J PLewicki, A JNelson, J HSatcher Jr, JBiener, T FBaumann, et al. Toward macroscale, isotropic carbons with graphene-sheet-like electrical and mechanical properties. Advanced Functional Materials, 2014, 24(27): 4259–4264 https://doi.org/10.1002/adfm.201400316
62	ECharon, J N Rouzaud, J Aléon. Graphitization at low temperatures (600–1200 °C) in the presence of iron implications in planetology. Carbon, 2014, 66: 178–190 https://doi.org/10.1016/j.carbon.2013.08.056
63	JXia, N Zhang, SChong, DLi, Y Chen, CSun. Three-dimensional porous graphene-like sheets synthesized from biocarbon via low-temperature graphitization for a supercapacitor. Green Chemistry, 2018, 20(3): 694–700 https://doi.org/10.1039/C7GC03426A
64	HWang, X B Li, L Gao, H LWu, JYang, L Cai, T BMa, C HTung, L ZWu, GYu. Three-dimensional graphene networks with abundant sharp edge sites for efficient electrocatalytic hydrogen evolution. Angewandte Chemie International Edition, 2018, 57(1): 192–197 https://doi.org/10.1002/anie.201709901
65	HRen, M Tang, BGuan, KWang, J Yang, FWang, MWang, J Shan, ZChen, DWei, et al. Hierarchical graphene foam for effcient omnidirectional solar-thermal energy conversion. Advanced Materials, 2017, 29(38): 1702590–1702596 https://doi.org/10.1002/adma.201702590
66	YShao, M F El-Kady, C W Lin, G Zhu, K LMarsh, J YHwang, QZhang, YLi, H Wang, R BKaner. 3D freeze-casting of cellular graphene films for ultrahigh-power-density supercapacitors. Advanced Materials, 2016, 28(31): 6719–6726 https://doi.org/10.1002/adma.201506157
67	B GCompton, J A Lewis. 3D-printing of lightweight cellular composites. Advanced Materials, 2014, 26(34): 5930–5935 https://doi.org/10.1002/adma.201401804
68	CZhu, T Y Han, E B Duoss, A M Golobic, J D Kuntz, C M Spadaccini, M A Worsley. Highly compressible 3D periodic graphene aerogel microlattices. Nature Communications, 2015, 6(1): 6962–6969 https://doi.org/10.1038/ncomms7962
69	JSha, Y Li, R VSalvatierra, TWang, P Dong, YJi, S KLee, CZhang, JZhang, R HSmith, et al. Three-dimensional printed graphene foams. ACS Nano, 2017, 11(7): 6860–6867 https://doi.org/10.1021/acsnano.7b01987
70	WQi, P Yan, D SSu. Oxidative dehydrogenation on nanocarbon: Insights into the reaction mechanism and kinetics via in situ experimental methods. Accounts of Chemical Research, 2018, 51(3): 640–648 https://doi.org/10.1021/acs.accounts.7b00475
71	XGuo, W Qi, WLiu, PYan, F Li, CLiang, D SSu. Oxidative dehydrogenation on nanocarbon: Revealing the catalytic mechanism using model catalysts. ACS Catalysis, 2017, 7(2): 1424–1427 https://doi.org/10.1021/acscatal.6b02936
72	WLiu, B Chen, XDuan, K HWu, WQi, X Guo, BZhang, D SSu. Molybdenum carbide modified nanocarbon catalysts for alkane dehydrogenation reactions. ACS Catalysis, 2017, 7(9): 5820–5827 https://doi.org/10.1021/acscatal.7b01905
73	XYang, Y Cao, HYu, HHuang, HWang, F Peng. Unravelling the radical transition during the carbon-catalyzed oxidation of cyclohexane by in situ electron paramagnetic resonance in the liquid phase. Catalysis Science & Technology, 2017, 7(9): 4431–4443 https://doi.org/10.1039/C7CY00958E
74	J HYang, G Sun, YGao, HZhao, P Tang, JTan, A HLu, DMa. Direct catalytic oxidation of benzene to phenol over metal-free graphene-based catalyst. Energy & Environmental Science, 2013, 6(3): 793–798 https://doi.org/10.1039/c3ee23623d
75	SIndrawirawan, H Sun, XDuan, SWang. Low temperature combustion synthesis of nitrogen-doped graphene for metal-free catalytic oxidation. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2015, 3(7): 3432–3440 https://doi.org/10.1039/C4TA05940A
76	XDuan, K O’Donnell, HSun, YWang, S Wang. Sulfur and nitrogen co-doped graphene for metal-free catalytic oxidation reactions. Small, 2015, 11(25): 3036–3044 https://doi.org/10.1002/smll.201403715
77	Z FHuang, H W Bao, Y Y Yao, W Y Lu, W X Chen. Novel green activation processes and mechanism of peroxymonosulfate based on supported cobalt phthalocyanine catalyst. Applied Catalysis B: Environmental, 2014, 154: 36–43 https://doi.org/10.1016/j.apcatb.2014.02.005
78	JDiao, H Liu, JWang, ZFeng, T Chen, CMiao, WYang, D S Su. Porous graphene-based material as an efficient metal free catalyst for the oxidative dehydrogenation of ethylbenzene to styrene. Chemical Communications, 2015, 51(16): 3423–3425 https://doi.org/10.1039/C4CC08683J
79	ADhakshinamoorthy, MLatorre-Sanchez, A MAsiri, APrimo, HGarcia. Sulphur-doped graphene as metal-free carbocatalysts for the solventless aerobic oxidation of styrenes. Catalysis Communications, 2015, 65: 10–13 https://doi.org/10.1016/j.catcom.2015.02.018
80	G BGonçalves, S GPires, M QSimoes, M SNevesb, P PMarques. Three-dimensional graphene oxide: A promising green and sustainable catalyst for oxidation reactions at room temperature. Chemical Communications, 2014, 50(57): 7673–7676 https://doi.org/10.1039/C4CC02092H
81	JLong, X Xie, JXu, QGu, L Chen, XWang. Nitrogen-doped graphene nanosheets as metal-free catalysts for aerobic selective oxidation of benzylic alcohols. ACS Catalysis, 2012, 2(4): 622–631 https://doi.org/10.1021/cs3000396
82	CRizescu, I Podolean, JAlbero, V IParvulescu, S MComan, CBucur, MPuchec. Garcia H. N-Doped graphene as a metal-free catalyst for glucose oxidation to succinic acid. Green Chemistry, 2017, 19(8): 1999–2005 https://doi.org/10.1039/C7GC00473G
83	QGu, G Wen, YDing, K HWu, CChen, D Su. Reduced graphene oxide: A metal-free catalyst for aerobic oxidative desulfurization. Green Chemistry, 2017, 19(4): 1175–1181 https://doi.org/10.1039/C6GC02894B
84	SGu, S Wunder, YLu, MBallauff, RFenger, KRademann, BJaquet, AZaccone. Kinetic analysis of the catalytic reduction of 4 nitrophenol by metallic nanoparticles. Journal of Physical Chemistry C, 2014, 118(32): 18618–18625 https://doi.org/10.1021/jp5060606
85	ZWang, R Su, DWang, JShi, J X Wang, Y Pu, J FChen. Sulfurized graphene as efficient metal-free catalysts for reduction of 4-nitrophenol to 4-aminophenol. Industrial & Engineering Chemistry Research, 2017, 56(46): 13610–13617 https://doi.org/10.1021/acs.iecr.7b03217
86	JLiu, X Yan, LWang, LKong, P Jian. Three-dimensional nitrogen-doped graphene foam as metal-free catalyst for the hydrogenation reduction of p-nitrophenol. Journal of Colloid and Interface Science, 2017, 497: 102–107 https://doi.org/10.1016/j.jcis.2017.02.065
87	JPan, S Song, JLi, FWang, X Ge, SYao, XWang, H Zhang. Solid ion transition route to 3D S-N-codoped hollow carbon nanosphere/graphene aerogel as a metal-free handheld nanocatalyst for organic reactions. Nano Research, 2017, 10(10): 3486–3495 https://doi.org/10.1007/s12274-017-1560-0
88	BQiu, M Xing, JZhang. Recent advances in three-dimensional graphene based materials for catalysis applications. Chemical Society Reviews, 2018, 47(6): 2165–2216 https://doi.org/10.1039/C7CS00904F
89	ZWang, Y Pu, DWang, JShi, J X Wang, J F Chen. 3D-foam-structured nitrogen-doped graphene-Ni catalyst for highly efficient nitrobenzene reduction. AIChE Journal. American Institute of Chemical Engineers, 2018, 64(4): 1330–1338 https://doi.org/10.1002/aic.16016
90	YGao, D Ma, CWang, JGuan, X Bao. Reduced graphene oxide as a catalyst for hydrogenation of nitrobenzene at room temperature. Chemical Communications, 2011, 47(8): 2432–2434 https://doi.org/10.1039/C0CC04420B
91	FYang, C Chi, CWang, YWang, Y Li. High graphite N content in nitrogen-doped graphene as an efficient metal-free catalyst for reduction of nitroarenes in water. Green Chemistry, 2016, 18(15): 4254–4262 https://doi.org/10.1039/C6GC00222F
92	FHu, M Patel, FLuo, CFlach, RMendelsohn, EGarfunkel, HHe, M Szostak. Graphene-catalyzed direct friedel-crafts alkylation reactions: mechanism, selectivity, and synthetic utility. Journal of the American Chemical Society, 2015, 137(45): 14473–14480 https://doi.org/10.1021/jacs.5b09636
93	YGao, P Tang, HZhou, WZhang, HYang, N Yan, GHu, DMei, J Wang, DMa. Graphene oxide catalyzed C‒H bond activation: The importance of oxygen functional groups for biaryl construction. Angewandte Chemie, 2016, 128(9): 3176–3180 https://doi.org/10.1002/ange.201510081
94	AYang, J Li, CZhang, WZhang, NMa. One-step amine modification of graphene oxide to get a green trifunctional metal-free catalyst. Applied Surface Science, 2015, 346: 443–450 https://doi.org/10.1016/j.apsusc.2015.04.033
95	X HLi, M Antonietti. Polycondensation of boron- and nitrogen-codoped holey graphene monoliths from molecules: Carbocatalysts for selective oxidation. Angewandte Chemie, 2013, 52(17): 4670–4674 https://doi.org/10.1002/ange.201209320
96	FYang, X Fan, CWang, WYang, L Hou, XXu, AFeng, S Dong, KChen, YWang, et al. P-doped nanomesh graphene with high-surface-area as an efficient metal-free catalyst for aerobic oxidative coupling of amines. Carbon, 2017, 121: 443–451 https://doi.org/10.1016/j.carbon.2017.05.101
97	D HLan, L Chen, C TAu, S FYin. One-pot synthesized multi-functional graphene oxide as a water-tolerant and efficient metal-free heterogeneous catalyst for cycloaddition reaction. Carbon, 2015, 93: 22–31 https://doi.org/10.1016/j.carbon.2015.05.023
98	MLacroix, L Dreibine, BTymowski, FVigneron, DEdouard, DBégin, PNguyen, CPham, S Savin-Poncet, FLuck, M JLedoux, CPham-Huu. Silicon carbide foam composite containing cobalt as a highly selective and re-usable Fischer-ropsch synthesis catalyst. Applied Catalysis A, General, 2011, 397(1): 62–72 https://doi.org/10.1016/j.apcata.2011.02.012
99	XLi, X Pan, LYu, PRen, X Wu, LSun, FJiao, X Bao. Silicon carbide-derived carbon nanocomposite as a substitute for mercury in the catalytic hydrochlorination of acetylene. Nature Communications, 2014, 5(1): 3688–3694
100	SHaase, M Weiss, RLangsch, TBauer, RLange. Hydrodynamics and mass transfer in three-phase composite minichannel fixed-bed reactors. Chemical Engineering Science, 2013, 94(5): 224–236 https://doi.org/10.1016/j.ces.2013.01.050
101	P CLeung, F Recasens, J MSmith. Hydration of isobutene in a trickle-bed reactor: Wetting efficiency and mass transfer. AIChE Journal. American Institute of Chemical Engineers, 1987, 33(6): 996–1007 https://doi.org/10.1002/aic.690330612
102	SLeveneur, J Wärnå , TSalmi, D YMurzin, LEstel. Interaction of intrinsic kinetics and internal mass transfer in porous ion-exchange catalysts: Green synthesis of peroxycarboxylic acids. Chemical Engineering Science, 2009, 64(19): 4101–4114 https://doi.org/10.1016/j.ces.2009.05.055
103	G WChu, Y J Song, W J Zhang, Y Luo, H KZou, YXiang, J FChen. Micromixing efficiency enhancement in a rotating packed bed reactor with surface-modified nickel foam packing. Industrial & Engineering Chemistry Research, 2015, 54(5): 1697–1702 https://doi.org/10.1021/ie504407a

Viewed

Full text

Abstract

Cited

Shared

Discussed