Catalysis of semihydrogenation of acetylene to ethylene: current trends, challenges, and outlook

doi:10.1007/s11705-021-2113-3

Front. Chem. Sci. Eng.

2022, Vol. 16

Issue (7) : 1031-1059 https://doi.org/10.1007/s11705-021-2113-3

REVIEW ARTICLE

Catalysis of semihydrogenation of acetylene to ethylene: current trends, challenges, and outlook

Toyin D. Shittu¹, Olumide B. Ayodele^2,³(

)

¹. Department of Chemical and Petroleum Engineering, United Arab Emirates University, Al-Ain 15551, United Arab Emirates
². Department of Micro and Nanofabrication, International Iberian Nanotechnology Laboratory, Braga 4715-330, Portugal
³. School of Chemical Engineering, Engineering Campus, University of Science Malaysia, Nibong Tebal 14300, Malaysia

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Abstract

Ethylene is an important feedstock for various industrial processes, particularly in the polymer industry. Unfortunately, during naphtha cracking to produce ethylene, there are instances of acetylene presence in the product stream, which poisons the Ziegler–Natta polymerization catalysts. Thus, appropriate process modification, optimization, and in particular, catalyst design are essential to ensure the production of highly pure ethylene that is suitable as a feedstock in polymerization reactions. Accordingly, carefully selected process parameters and the application of various catalyst systems have been optimized for this purpose. This review provides a holistic view of the recent reports on the selective hydrogenation of acetylene. Previously published reviews were limited to Pd catalysts. However, effective new metal and non-metal catalysts have been explored for selective acetylene hydrogenation. Updates on this recent progress and more comprehensive computational studies that are now available for the reaction are described herein. In addition to the favored Pd catalysts, other catalyst systems including mono, bimetallic, trimetallic, and ionic catalysts are presented. The specific role(s) that each process parameter plays to achieve high acetylene conversion and ethylene selectivity is discussed. Attempts have been made to elucidate the possible catalyst deactivation mechanisms involved in the reaction. Extensive reports suggest that acetylene adsorption occurs through an active single-site mechanism rather than via dual active sites. An increase in the reaction temperature affords high acetylene conversion and ethylene selectivity to obtain reactant streams free of ethylene. Conflicting findings to this trend have reported the presence of ethylene in the feed stream. This review will serve as a useful resource of condensed information for researchers in the field of acetylene-selective hydrogenation.

Keywords selectivity hydrogenation acetylene ethylene palladium

Corresponding Author(s): Olumide B. Ayodele

Online First Date: 05 January 2022 Issue Date: 15 July 2022

Cite this article:

Toyin D. Shittu,Olumide B. Ayodele. Catalysis of semihydrogenation of acetylene to ethylene: current trends, challenges, and outlook[J]. Front. Chem. Sci. Eng., 2022, 16(7): 1031-1059.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-021-2113-3
https://academic.hep.com.cn/fcse/EN/Y2022/V16/I7/1031

Scheme 1 Reaction mechanism of acetylene hydrogenation.

Fig.1 Simulation data showing the effects of temperature on (a) acetylene conversion and ethylene selectivity as well as (b) acetylene and hydrogen coverage at atmospheric pressure and feed composition of 2% C₂H₂ and 20% H₂. Reprinted with permission from ref. [13], copyright 2019, American Chemical Society.

Fig.2 Effect of acetylene partial pressure on acetylene turnover frequency (Black, green, and red represent Pd/Al₂O_3, PdIn_0.23/Al₂O₃, and PdIn_0.41/Al₂O₃, respectively). Reprinted with permission from ref. [43], copyright 2017, American Chemical Society.

S/N	Feed composition /vol%	Temperature /°C	Pressure /MPa	GHSV/SV/FL	Tested catalyst	Preparation method	Conversion/%	Selectivity/%	Ref.
1	0.6 C₂H₂, 1.8 H₂, bal. N₂	30–70	2.1	120 mL·min^–1	PdIn/Al₂O₃	Incipient wetness, co-impregnation	ca. 98	ca. 90	[43]
2	2 C₂H₂, 20 H₂, bal. He and 2 C₂H₂, 40 C₂H₄, 20 H₂, bal. He	60–110	N.A.	180000 mL·g^–1·h^–1	PdZn	Wet impregnation	100	100	[8]
3	0.738 C₂H₂, 34.45 C₂H₆, 64.59 C₂H₄, H₂:C₂H₂ = 0.5–1.5	35–60	1.5–2.0	2600–6200 h^–1	PdAg/α-Al₂O₃	Impregnation	ca. 80	ca. 94	[2]
4	1 C₂H₂, 2 H₂, bal. N₂	80	0.1	30000 mL·g^–1·h^–1	Pd/TiO₂	Incipient wetness impregnation	100	68	[53]
5	1 C₂H₂, 2 H₂, bal. N₂	40–100	0.1	30000 mL·g^–1·h^–1	Pd/SiC	Incipient wetness impregnation	98	96	[54]
6	0.951 C₂H₂ in C₂H₄, H₂:C₂H₂ = 2:1	30–55	0.05	10056 h^–1	PdGa/MgO-Al₂O₃	Impregnation	100	95	[4]
7	0.35 C₂H₂, 0.6 H₂, bal. N₂, H₂:C₂H₂ = 2:1	30–100	0.4	8040 h^–1	Pd/HT, Pd/Al₂O₃, Pd/MgO	Wet impregnation	100 for Pd/HT	100 for Pd/HT	[42]
8	C₂H₂:H₂:N₂ = 1:2:6	130	N.A.	18000 h^–1	Pd-MgO/TiO₂	Wet impregnation	97.7	70.7	[55]
9	2 C₂H₂, 50 C₂H₄, 4 H₂, bal. Ar			10–120 mL·min^–1	NaN₃-Pd/SAC	Impregnation	ca. 36	ca. 60	[19]
10	0.5 C₂H₂, 35 C₂H₄, bal. N₂, H₂:C₂H₂ = 5:1	0–125		66 mL·min^–1	Pd/C, Pd/MgO, Pd/Al₂O₃	Wet impregnation	100	ca. 55	[3]
11	H₂ = 4.3, C₂H₄ = 70, C₂H₂ = M (1, 0.6, 0.8), Ar= M (27.4, 25.1, 24.9) (mol%)	51 and 62	0.12	200 mL·min^–1	Pd/α-Al₂O₃	Impregnation	ca. 90	N.A.	[6]
12	0.72 C₂H₂, 60.1 C₂H₄, 9.14 C₂H₆, 30.02 H₂	10–20	1.520	21.6–216 cm³·gcat^–1·s^–1	Pd/α-Al₂O₃ Pd/γ-Al₂O₃	Wet impregnation	100	N.A.	[56]
13	0.72 C₂H₂, 1.46 H₂, 52.6 C₂H₄ in He		0.1	60 mL·min^–1	Pd/TiO₂ PdAg/TiO₂	Photo deposition method	82	79	[57]
14	C₂H₂:H₂ = 0.3	50–75	0.00013		Pt/M, Pd/M, Rh/M, Ir/M (M= SiO₂, NaY)	Wet impregnation, ion exchange	100	ca. 95	[58]
15	1 C₂H₂, 20 C₂H₄, 10 H₂, bal. He	20–180		60000 h^–1	Pd/ND@G		100	ca. 90	[59]
16	0.5 C₂H₂, 35 C₂H₄, 1000 ppm CO, bal. N₂, feed gas:H₂ = 5:1	70			Pd/SiO₂ PdAg/SiO₂	Sequential impregnation, co-impregnation	99.3	ca. 85	[23]
17	0.962 C₂H₂ in C₂H₄, H₂:C₂H₂	30–70	0.2	10056 h^–1	PdNi/MMO PdNi/MgAl-LDH	Co-impregnation, sol-immobilization	100	80	[21]
18	0.5 C₂H₂, 50 C₂H₄, 5 H₂, bal. He	200		30 mL·min^–1	PdGa		ca. 90	ca. 75	[60]
19	1 C₂H₂, 1.1 H₂, bal. He	40		15–35 mL·min^–1	Pd/SiO₂ PdAu/SiO₂	Ion exchange	33.7	77.2	[46]
20		75–175			Pd/N-G	Freeze-drying-assisted method	99	93.5	[61]
21	1 C₂H₂, 20 C₂H₄, 3 H₂, bal. N₂			120 mL·min^–1	Pd/CNT	Impregnation, incipient wetness	ca. 85	ca. 40	[62]
22	H₂:C₂H₂ = 2:1 Ar 70	60–180		33000 h^–1	Pd/MWNTs PdSn/MWNTs	Chemical vapor deposition and polyol method	ca. 100	96	[11]
23	1.5 C₂H₂, 1.7 H₂, bal. C₂H₄	40		52580, 32577, 22534, 12385 h^–1	Pd/α-Al₂O₃ Pd/γ-Al₂O₃ Pd/γ-Al₂O₃-α-Al₂O₃	Incipient wetness impregnation	ca. 85	ca. 100	[63]
24	1.2 C₂H₂, H₂:C₂H₂ = 2:1_, bal. N₂ and 0.6 C₂H₂, 5.4 C₂H₄, H₂:C₂H₂ = 2:1_, bal. N₂	50–225	0.1	256000 h^–1	PdP₂/TiO₂	Impregnation	100	84	[9]
25	0.6 C₂H₂, 1.8 H₂, bal. N₂ H₂:C₂H₂ = 3:1	50–150	0.1	24000 h^–1	Cu/Al₂O₃ Pd/Al₂O₃ PdCu/Al2O₃	Impregnation	>99	>80	[64]
26	0.6 C₂H₂, 99.4 N₂, H₂:C₂H₂ = 3:1 or 10:1 and 0.6 C₂H₂, 5.4 C₂H₄, bal. 94 N₂, H₂:C₂H₂ = 3:1 or 1.5:1	50–150	0.1–0.5	24000 h^–1	Cu/Al₂O₃ Pd/Al₂O₃ PdCu/Al₂O₃	Sequential impregnation, co-impregnation	98	80	[65]
27	1.2 C₂H₂, 32 C₂H₄, 4.3 H₂, bal. He	57–107		16.2 mL·min^–1	PdZn/CeO₂	Wet impregnation	98	98	[66]
28	H₂:C₂H₂ = 5–30	250–400	0.1		In₂O₃, CeO₂		100	>85	[67]
29	1 C₂H₂, 30 C₂H₄, 1 C₃H₈, 1 H₂, 67 Ar	30–60	1	4000 h^–1	Pd/Al₂O₃ PdAg/Al₂O₃	Impregnation	82	64	[68]
30	H₂:HC= 3, 5, 7, 10, 30, or 60, Conc. of C₂H₂ = 0.1 and 0.3	30–450	0.1	7500 h^–1	Au/CeO₂	Direct anionic exchange	100	100	[69]
31	H₂:C₂H₂ = 2:1	40–250			Au/Al₂O₃	Deposition–precipitation	N.A.	100	[70]
32	2 C₂H₂, 80 H₂ in He	27–373	0.1	50000 h^–1	PG(Al₂Au) PG(Ag₃Au)		N.A.	>95	[71]
33	0.15 C₂H₂, 1.5 H₂, bal. He	80–250		40000 mL·g^–1·h⁻¹	Au-Cu/SBA-15	Deposition	ca. 45	ca. 50	[72]
34	0.8 C₂H₂, 16 H₂, bal. C₂H₄	150–250 150–400		90000 mL·g^–1·h^–1	Au/SiO₂	Deposition	ca. 75	ca. 80	[73]
35	0.6 C₂H₂, 3 H₂, 96.4 Ar	25–300		17200 mL·g^–1·h^–1	Au/CeO₂	Immobilization	100	50	[74]
36	1.5 C₂H₂, 2 H₂, bal. C₂H₄	40		100 mL·min^–1	AuPd/TiO₂	Co-impregnation, deposition, precipitation	ca. 50	>95	[75]
37	1 C₂H₂, 20 C₂H₄, 5 H₂, bal. He	65		50–250 cm³·min^–1	Pd/SiO₂ PdAg/SiO₂ PdAu/SiO₂	Electroless deposition	60	50	[76]
38	H₂/C₂H₂/N₂ = 60/15/25	175		700 mL·min^–1	Zn/Al₂O₃ Ni/Al₂O₃ ZnNi/Al₂O₃	Co-precipitation	N.A.	N.A.	[77]
39	1 C₂H₂, 5 H₂, bal. Ar	180	0.1	36000 mL·g^–1·h^–1	NiIn/SiO₂	Incipient wetness impregnation	100	ca. 60	[78]
40	C₂H₂:C₂H₄:H₂ = 1:70:4 0.5 C₂H₂, 35 C₂H₄, bal. N₂	20–200		21000 mL·g^–1·h^–1	Ni/CeO₂	Incipient wetness impregnation, co-precipitation, sol-gel solution combustion synthesis	100	100	[79]
41	1 C₂H₂, 20 C₂H₄, 20 H₂, bal. He	40–200		60000 mL·g^–1·h^–1	Ni/SiO₂ NiAg/SiO₂	Wetness co-impregnation	98	N.A.	[80]
42	0.5–4 C₂H₂, 0.005–1 CO, 6–35 H₂, bal. He	80		100 cm³·min^–1	Ni/SiO₂	Incipient wetness impregnation	ca. 45	N.A.	[81]
43	1 C₂H₂, 5 H₂, 94 N₂	180	0.1	36000 mL·g^–1·h^–1	Ni/SiO₂ NiGa/SiO₂	Incipient wetness impregnation	100	ca. 81	[82]
44	0.5 C₂H₂, 5 H₂, 50 C₂H₄, bal. He	200		40 mL·min^–1	Pd₂Ga₁₋_xSn_x		ca. 100	ca. 85	[83]
45	0.5 C₂H₂, 5 H₂, 50 C₂H₄, bal. He	200		30 mL·min^–1	BiRh nanoplate	Microwave-assisted polyol process	ca. 100	ca. 93	[84]
46	0.65 C₂H₂, 50 C₂H₄, 5 H₂, bal. Ar	80–120	0.1	40 mL·min^–1	Pd/Ni(OH)₂ Pd/NiO Pd/SiO₂	Incipient impregnation	ca. 100	80	[85]
47		40–140			PdZn/ZIF-8C	Impregnation	100	ca. 90	[86]
48		100–165			Ni₃Ga/MIHMs	Topological self-template strategy	100	ca. 85	[87]
49	10 C₂H₂, 90 C₂H₄, C₂H₂ + C₂H₄:H₂ = 1:3_, bal. N₂	110 and 120		7.800 and 14.600 mL·g^–1·h^–1	(N) Gr, (P) Gr, (S) Gr, rGO, GO Gr	Pyrolysis hummers oxidation, hydrothermal reduction	99	91.6	[88]
50	0.5 C₂H₂, 50 C₂H₄, 5 H₂, bal. He	30–120			Pd@H-Zn/Co-ZIF Pd@S-Zn/Co-ZIF PdNPs/C		>80	>80	[89]
51	1 C₂H₂, 10 H₂, bal. Ar	180–240	0.1	36000 mL·g^–1·h^–1	MoP	Hydrogen reduction	>99	73	[90]
52	0.01–0.294 C₂H₂, 39.5 C₂H₄, 0.76 H₂, bal. He	80		34 mL·min^–1	Pd/SiO₂	Ion exchange	N.A.	ca. 80	[91]
53					Pd/α-Al₂O₃ Pd/γ-Al₂O₃	Wet impregnation	N.A.	N.A.	[92]
54	1.2 C₂H₂, 93 C₂H₄, 2.4 H₂, bal. N₂ H₂:C₂H₂ = 1. 1.2, 1.3	90–180		135 mL·min^–1	Pd/MWCNT	Incipient wetness impregnation	100	93	[45]
55	H₂:C₂H₂ = 2, 45, 130	10–67	0.1	20–500 cm³·min^–1	Pd/SiO₂ Pd/Al₂O₃	Impregnation	N.A.	N.A.	[33]
56	0.6 C₂H₂, 49.3 C₂H₄, 1.2 H₂, bal. N₂	60		40–180 mL·min^–1	Pd(S) Pd(C)	Incipient wetness impregnation	70	50	[93]
57	1 C₂H₂, 35.5 C₂H₄, 15 H₂, bal. He and 0.3 C₂H₂, 0.44 H₂, bal. C₂H₄	21.5, 34, 48			Pd/Al₂O₃ Pd/SiO₂ PdCu/Al₂O₃	Deposition co-impregnation	ca. 40	ca. 90	[94]
58	C₂H₂:H₂ = 2:1, 2 C₂H₂ in C₂H₄		0.0073		Pd/Al₂O₃	Impregnation	ca. 85	ca. 90	[95]
59	C₂H₂:C₂H₄:D₂ = 9:1:40	302, 442, 502	0.0133		Pd/Al₂O₃	Deposition	ca. 50	ca. 70	[30]
60	2 C₂H₂, 4 H₂, bal. He 0.5 C₂H₂, 5 H₂, 50 C₂H₄, bal. He	120 and 200		30 mL·min^–1	PdGa, PdGa₇, Pd/Al₂O₃ Pd₂₀Ag₂₀	Milling, ammonia-assisted chemical etching	ca. 80	ca. 84	[96]
61	1.42 C₂H₂, 1.71 H₂, 15.47 C₂H₆, bal. C₂H₄	40		5400 h^–1	Pd/TiO₂	Incipient wetness impregnation	ca. 40	ca. 93	[97]
62	1 C₂H₂, 20 C₂H₄, 20 H₂, bal. He	40–240		60000 mL·g^–1·h^–1	PdAu/SiO₂ Au/SiO₂ Pd/SiO₂	Incipient wetness co-impregnation	85.9	56.4	[98]
63	1 C₂H₂, 20 C₂H₄, 20 H₂, bal. He	40–400		60000 mL·g^–1·h^–1	PdAg/SiO₂	Incipient wetness co-impregnation	93	80	[99]
64	1 C₂H₂, 1 C₂H₄, 2 H₂, 96 Ar	25	0.1	0–20 L·h^–1	Pd/C	Impregnation	50	76	[100]
65	H₂:C₂H₂ = 9:1	100 and 160	0.006–0.06	30 cm³·min^–1	Pt/Naβ-Al₂O₃	Deposition by sputtering	ca. 84	ca. 80	[101]
66	0.351 C₂H₂, 0.697 H₂, 30.5 C₂H₄, 66.7 N₂	170	0.1	6000 h^–1	Pd-IL/Al₂O₃	Incipient impregnation	100	ca. 90	[102]
67	C₂H₂ 0.58, C₂H₄ 57.33, C₂H₆ 10.24, C₃H₆ 0.12, H₂ 30.45, CO 1.28 (mol%)	30–110	1.6	133 cm³·min^–1	Pd/Al₂O₃ Ag/Al₂O₃ PdAg/Al₂O₃	Impregnation	ca. 100	ca. 100	[103]

Tab.1 Parameters of the selective hydrogenation of acetylene reported in the literature

Fig.3 Structure of PdZn intermetallic nanoparticle. (a) Unit cell (in Å) of 1:1 PdZn L1₀ type alloy; surfaces of (b) PdZn (100) with 1:1 stoichiometric ratio and (c) PdZn (111); slab layer models for (d) PdZn (100) and (e) PdZn (111). The neighboring Pd–Pd pair is the nearest neighbor; for example, on the PdZn (100) surface, Pd₁ (blue) is neighboring with two Pd₂ units underneath (green); on the PdZn (111) surface, Pd (blue) is neighboring with two surface Pd atoms and one Pd atom underneath (green). Reprinted with permission from ref. [8], copyright 2016, American Chemical Society.

Tab.2 Vibrational frequency of CO and the adsorption energies on the PdZn (100), PdZn (111), and Pd (111) surfaces ^a)

Fig.4 Acetylene conversion and selectivity with (a) 10 mg Pd/ZnO and (b) 2.8 mg Pd/Al₂O₃. Reacting gas composition comprises 2 vol% acetylene and 20 vol% hydrogen (balance in He) with a flow rate of 30 mL·min^–1. Reprinted with permission from ref. [8], copyright 2016, American Chemical Society.

Fig.5 (a) Ethene selectivity as a function of reaction temperature and (b) acetylene conversion using different catalysts, where I= Pd/MgO–Al₂O₃, II= Pd–Ga (2:1)/MgO–Al₂O₃, and III= Pd–Ga (1:5)/MgO–Al₂O₃ at a relative pressure of 0.05 MPa, GHSV of 10056 h^–1, 33.2% C₂H₄/C₂H₂ mixed gases (containing 0.951% acetylene in ethene), 0.6% H₂, and 66.2% N₂. Reprinted with permission from ref. [4], copyright 2001, Elsevier.

Fig.7 Fourier transform infrared spectra of reduced CuPd bimetallic catalysts after exposure to CO at 298 K at increasing pressures. (a) 10-CuPd; (b) 25-CuPd; (c) 50-CuPd; (d) 100-CuPd. Reprinted with permission from ref. [64], copyright 2014, Elsevier.

Fig.8 Promotion of selectivity by the addition of Sn to Pd in different molar ratios and at various temperatures (all catalysts contain 0.1 wt% Pd). Reprinted with permission from ref. [11], copyright 2012, Elsevier.

Fig.11 Radar plot of the rate with key theoretical indicators including the adsorption energy of the alkyne (E_ads(C₂H₂)) and activation energy for H₂ dissociation (E_a(H₂)) for activity, alkene adsorption energy (E_ads(C₂H₄)) and ensemble area (A_ensemble) for selectivity, and segregation energy (E_seg) for stability. Values closest to the perimeter lead to enhanced properties. Blue shaded area connects the optimal values reported till date for the Pd₃S system. Reprinted with permission from ref. [122], copyright 2018, Nature.

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