Progress on Renewable Energy-Driven Synthesis of Cyclic Carbonates from CO2

doi:10.6023/cjoc202406044

Abstract

The cyclic carbonate is a crucial chemical product extensively employed in battery electrolytes, cosmetics, paints, and various other industries. Additionally, it serves as an eco-friendly solvent and reaction precursor for organic synthesis. As the commercial products via CO₂ conversion, cyclic carbonates were mainly prepared through the cycloaddition reaction of epoxides with CO₂. By far, the production of cyclic carbonates still relies on the thermal catalytic cycloaddition reactions, in which high temperature is always required due to the high energy barrier for the ring-opening of epoxides and CO₂activation. In recent years, novel catalytic pathways have been proposed accompanied with the emergence of new catalytic materials. Especially the light/electricity-driven cycloaddition reactions render the synthesis of cyclic carbonates under room tem- perature. In addition, achievements have also been made on electron-induced cyclic carbonate synthesis from olefins or vicinal diols and CO₂. The present review provides a comprehensive overview of the photocatalytic/electrocatalytic synthesis of cyclic carbonates from CO₂, aiming to offer novel insights into the design of innovative reaction pathways and catalytic materials by incorporating material engineering and catalytic mechanisms.

Key words: carbon dioxide, catalytic activation, renewable energy, cyclic carbonate, photothermal synergy

Cite this article

Lifeng Xu, Anguo Wu, Fangyu Yu, Hongru Li, Liangnian He. Progress on Renewable Energy-Driven Synthesis of Cyclic Carbonates from CO₂[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3091-3105.

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References 57

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Entry	Epoxide (n/mmol)	Catalyst (dosage)	TBAB/mol%	Solvent^e (V/mL)	Reaction condition	Yield/%	Ref.
1	Propylene oxide (1)	CoPc/TiO₂(100 mg)	10	S1/S2 (10/5)	24 h, 20 W LED	92	[3]
2	Propylene oxide (3)	Ti₁₈Bi₄O₂₉Bz₂₆(20 μmol)	1.6		14 h, 300 W Xe lamp	>99	[4]
3^b	Propylene oxide (1.4)	BiNbO₄/r-GO (50 mg)	2	S1/S2 (10/2)	24 h, 300 W Hg lamp	65	[5b]
4^c	Propylene oxide (1.4)	FeNbO₄/r-GO (50 mg)	2	S1/S2 (4/1)	24 h, 500 W Hg lamp	57	[5a]
5	Phenyl oxirane (44)	W₁₈O₄₉/g-C₃N₄(30 mg)	2.5		4 h, 300 W Xe lamp	60	[6]
6	Propylene oxide (71)	g-C₃N₄/Ag (10 mg)	0.7		6 h, 300 W Xe lamp		[7]
7	Phenyl oxirane (0.15)	Pd/SCNT-500 (10 mg)	67		24 h, 0.15w/cm²455nm	97	[8]
8^d	Propylene oxide (10)	Zr-Thia/g-CN (50 mg)	2.5		30 h, 250w Hg lamp	90.8	[9]
9^c	Propylene oxide (1.4)	BiNbO₄/NH₂-MIL-125(Ti) (50 mg)	2	S1/S2 (5/1)	72 h, 300 W Hg lamp	74	[10b]
10^c	Propylene oxide (1.4)	FeNbO₄/NH₂-MIL-125(Ti) (50 mg)	2	S1/S2 (4/1)	72 h, 300 W Hg lamp	52	[10a]
11	Propylene oxide (4.5)	Bi-PCN-224 (30 mg)	11		6 h, 300 W Xe lamp	99	[11]
12	Propylene oxide (0.1)	UiO-bpydc (Zn) (20 mg)	500	S3 (3)	9 h, 300 W Xe lamp	90	[12]
13	Epichlorohydrin (20)	PCN-224 (Mg) (0.5 mmol)	1		6 h, LED light (3*30 W)	99	[13]
14	Epichlorohydrin (38)	Fe-BDC (15 mg)	0.8		4 h, 300 W Xe lamp	45	[14]
15	Epichlorohydrin (12.75)	Fe-DBP (10 mg)	8		12 h, 1000 W Xe lamp.	97	[15]
16	Epichlorohydrin (0.2)	TpPa-1 (5 mg)	5	S1 (5)	8 h, Blue light 455nm	82	[16]
17	Propylene oxide (0.25)	OH-P [5]-on-COF (1.5 mg)	5		8 h, LED lamp	99	[17]
18	Epichlorohydrin (1)	9,10-Anthraquinone (10 mol%)	10	S1 (10)	12 h, 20 W LED	93	[18]

Entry	Epoxide (n/mmol)	Catalyst (dosage)	TBAB/mol%	Solvent^e (V/mL)	Reaction condition	Yield/%	Ref.
1	Propylene oxide (1)	CoPc/TiO₂(100 mg)	10	S1/S2 (10/5)	24 h, 20 W LED	92	[3]
2	Propylene oxide (3)	Ti₁₈Bi₄O₂₉Bz₂₆(20 μmol)	1.6		14 h, 300 W Xe lamp	>99	[4]
3^b	Propylene oxide (1.4)	BiNbO₄/r-GO (50 mg)	2	S1/S2 (10/2)	24 h, 300 W Hg lamp	65	[5b]
4^c	Propylene oxide (1.4)	FeNbO₄/r-GO (50 mg)	2	S1/S2 (4/1)	24 h, 500 W Hg lamp	57	[5a]
5	Phenyl oxirane (44)	W₁₈O₄₉/g-C₃N₄(30 mg)	2.5		4 h, 300 W Xe lamp	60	[6]
6	Propylene oxide (71)	g-C₃N₄/Ag (10 mg)	0.7		6 h, 300 W Xe lamp		[7]
7	Phenyl oxirane (0.15)	Pd/SCNT-500 (10 mg)	67		24 h, 0.15w/cm²455nm	97	[8]
8^d	Propylene oxide (10)	Zr-Thia/g-CN (50 mg)	2.5		30 h, 250w Hg lamp	90.8	[9]
9^c	Propylene oxide (1.4)	BiNbO₄/NH₂-MIL-125(Ti) (50 mg)	2	S1/S2 (5/1)	72 h, 300 W Hg lamp	74	[10b]
10^c	Propylene oxide (1.4)	FeNbO₄/NH₂-MIL-125(Ti) (50 mg)	2	S1/S2 (4/1)	72 h, 300 W Hg lamp	52	[10a]
11	Propylene oxide (4.5)	Bi-PCN-224 (30 mg)	11		6 h, 300 W Xe lamp	99	[11]
12	Propylene oxide (0.1)	UiO-bpydc (Zn) (20 mg)	500	S3 (3)	9 h, 300 W Xe lamp	90	[12]
13	Epichlorohydrin (20)	PCN-224 (Mg) (0.5 mmol)	1		6 h, LED light (3*30 W)	99	[13]
14	Epichlorohydrin (38)	Fe-BDC (15 mg)	0.8		4 h, 300 W Xe lamp	45	[14]
15	Epichlorohydrin (12.75)	Fe-DBP (10 mg)	8		12 h, 1000 W Xe lamp.	97	[15]
16	Epichlorohydrin (0.2)	TpPa-1 (5 mg)	5	S1 (5)	8 h, Blue light 455nm	82	[16]
17	Propylene oxide (0.25)	OH-P [5]-on-COF (1.5 mg)	5		8 h, LED lamp	99	[17]
18	Epichlorohydrin (1)	9,10-Anthraquinone (10 mol%)	10	S1 (10)	12 h, 20 W LED	93	[18]

Entry	Catalyst^b	Zn form	Reaction condition	Light intensity^a	Product	Yield/%	Ref.
1	HPC-800	Zn atom	100 kPa CO₂, 10 h	300 mW•cm^–2	4-Bromomethyl-1,3-dioxolan-2-one	94	[22]
2	Zn SA-NC	Zn atom	100 kPa CO₂, 16 h	300 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	99	[23]
3	ZNC-800	Zn atom	100 kPa CO₂, 10 h	1000 mW•cm^–2	4-Methyl-1,3-dioxolan-2-one	94	[24]
4	Zn-Asp-300	ZnO	100 kPa CO₂, 4 h	152.5 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	92	[25]
5	ZNPC-600	ZnO	100 kPa CO₂, 6 h	500 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	99	[21]
6	ZnS / NPC-2	ZnS	100 kPa CO₂, 12 h	300 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	98	[26]
7	ZnO/NC-L	ZnO	100 kPa CO₂, 6 h	120 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	76	[27]

Entry	Catalyst^b	Zn form	Reaction condition	Light intensity^a	Product	Yield/%	Ref.
1	HPC-800	Zn atom	100 kPa CO₂, 10 h	300 mW•cm^–2	4-Bromomethyl-1,3-dioxolan-2-one	94	[22]
2	Zn SA-NC	Zn atom	100 kPa CO₂, 16 h	300 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	99	[23]
3	ZNC-800	Zn atom	100 kPa CO₂, 10 h	1000 mW•cm^–2	4-Methyl-1,3-dioxolan-2-one	94	[24]
4	Zn-Asp-300	ZnO	100 kPa CO₂, 4 h	152.5 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	92	[25]
5	ZNPC-600	ZnO	100 kPa CO₂, 6 h	500 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	99	[21]
6	ZnS / NPC-2	ZnS	100 kPa CO₂, 12 h	300 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	98	[26]
7	ZnO/NC-L	ZnO	100 kPa CO₂, 6 h	120 mW•cm^–2	4-Chloromethyl-1,3-dioxolan-2-one	76	[27]

Entry	Cathode\|anode	Supporting electrolyte	Solvent	Reaction condition	Epoxide	Yield/%	Ref.
1	Ss\|Mg	KBr, Ni(cyclam)Br₂	DMF	r.t., 100 kPa	Styrene oxide	92	[41]
2	Cu\|Mg/Al	[BMlm][BF₄]	r.t., 100 kPa	Propylene oxide	92	[42]
3	CuNPs\|Mg	0.1 mol/L TEAI	MeCN	25 ℃, 100 kPa	Propylene oxide	86	[43]
4	Cu/CS\|Mg	0.1 mol/L TEAI	MeCN	r.t., 100 kPa	Propylene oxide	94.7	[44]
5	AgNPs\|Mg	0.1 mol/L TEAI	MeCN	25 ℃, 100 kPa	Propylene oxide	70	[45]
6	Ss\|Mg	TBAI	MeCN	r.t., 100 kPa	(R)-Styrene oxide	59 (91% ee)	[46]
7	C\|Pt	TBAP, Ni(Ⅱ) complex	MeCN	r.t., 100 kPa	Styrene oxide	100	[47]
8	Cu(ND)/CP\|Pt	ZnCl₂, TBAB	MeCN	r.t., 100 kPa	Styrene oxide	74.9	[48]
9	HNSs\|Pt	ZnCl₂, TBAB	MeCN	r.t., 100 kPa	Styrene oxide	66.9	[49]
10	Ti/TiO₂-CNT-Pt\|C	[APMIm]DCA	MeCN	50 ℃, 100 kPa	Styrene oxide	95	[50]

可再生能源驱动的CO₂基环状碳酸酯合成研究进展

Progress on Renewable Energy-Driven Synthesis of Cyclic Carbonates from CO₂

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可再生能源驱动的CO2基环状碳酸酯合成研究进展