可再生能源驱动的CO2基环状碳酸酯合成研究进展

doi:10.6023/cjoc202406044

摘要/Abstract

环状碳酸酯是重要的化工产品, 在电池电解液、化妆品、油漆等领域具有广泛应用, 同时还是有机合成的绿色溶剂和反应原料. 环状碳酸酯是工业规模CO₂转化的重要产品, 主要通过环氧化物与CO₂的环加成反应进行制备. 在传统的热催化反应中, 由于环氧化物活化开环具有较高的能垒, 因而一般需要较高的反应温度. 近年来, 新材料的发展推动了环加成反应催化剂的创新, 新的催化模式不断出现, 尤其是光驱动和电驱动的环加成反应实现了温和条件下环状碳酸酯的制备. 此外, 电驱动的烯烃或邻二醇与CO₂合成环状碳酸酯也取得了初步的研究成果. 总结了光/电驱动的CO₂合成环状碳酸酯的反应, 旨在通过对材料设计和催化机理的介绍, 为新型反应路径和催化材料的设计提供新思路.

关键词: 二氧化碳, 催化活化, 可再生能源, 环状碳酸酯, 光热协同

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

引用此文

许立锋, 武安国, 于芳羽, 李红茹, 何良年. 可再生能源驱动的CO₂基环状碳酸酯合成研究进展[J]. 有机化学, 2024, 44(10): 3091-3105.

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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图/表 22

图式1. 热催化CO2合成环状碳酸酯的反应机理

Scheme 1. Plausible mechanism for thermocatalytic cyclic carbonates synthesis from carbon dioxide and epoxides

图1. CoPc/TiO2光催化制备环状碳酸酯

图2. BiNbO4/rGO光催化CO2和环氧化物合成环状碳酸酯

图式2. Mg-卟啉MOF光催化制备环状碳酸酯的机理

Scheme 2. Proposed reaction pathway for the photocatalytic synthesis of cyclic carbonates using PCN-224 (Mg)

图3. (a) TpPa-1的结构、(b) TpPa-1光催化反应机制和(c) OH-P[5]-on-COF的结构

Figure 3. (a) Structure of COF TpPa-1, (b) photocatalytic mechanism of TpPa-1, and (c) structure of OH-P[5]-on-COF

图式3. 9,10-蒽醌光催化制备环状碳酸酯

Scheme 3. Proposed reaction pathway for synthesis of cyclic carbonates using 9,10-anthraquinone as photocatalyst

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]

表1. 环氧化物与CO2环加成合成环状碳酸酯的光催化方法总结a

Table 1. Summary of photocatalytic methods for the synthesis of cyclic carbonates from the cycloaddition of epoxides with CO2

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]

表2. 氮掺杂多孔碳材料负载锌的催化性能

Table 2. Catalytic properties of N-doped porous carbon-supported Zinc

图式4. 壳聚糖煅烧合成羟基修饰的N掺杂多孔碳材料

Scheme 4. Synthesis of hydroxy-modified nitrogen-doped carbon materials from chitosan

图式5. 光热协同催化环加成反应机理

Scheme 5. Typical mechanism of photothermal synergistic cycloaddition reaction

图式6. CMS@MIL-88-NH2复合材料及其反应机理

Scheme 6. CMS@MIL-88-NH2 composite materials and their catalytic mechanism

图式7. COF-PI-2催化剂的结构

Scheme 7. Structure of the catalyst COF-PI-2

图式8. Ni(cyclam)Br2催化反应机理

Scheme 8. Catalytic reaction mechanism of Ni(cyclam)Br2

图式9. 电催化CO2和(R)-氧化苯乙烯环加成反应机理

Scheme 9. Reaction mechanism of cycloaddition reaction between CO2 and (R)-oxidized styrene

图式10. Ni(II)配合物催化反应机理

Scheme 10. Catalytic mechanism of Ni (II) complexes in electrocatalytic synthesis of cyclic carbonate

图式11. HNSs催化剂的吡啶N和羧酸基团上环加成的反应途径

Scheme 11. Reaction pathway of cycloaddition on pyridine N and carboxylic acid groups in HNSs catalysts

图式12. Ti/TiO2-CNT-Pt和[APMIm]DCA)协同催化机理

Scheme 12. Synergistic catalysis of Ti/TiO2-CNT-Pt and [APMIm]DCA in the cycloaddition reaction

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]

表3. 环氧化物与CO2环加成合成环状碳酸酯的电催化方法总结

Table 3. Summary of electrocatalytic methods for the synthesis of cyclic carbonates by cycloaddition of epoxy compounds and CO2

图式13. CO2与烯烃电合成环状碳酸酯机理

Scheme 13. Mechanism of electrosynthesis of cyclic carbonates from CO2 and olefins

图式14. CO2与二元醇电合成环状碳酸酯机理

Scheme 14. Mechanism of electrosynthesis of cyclic carbonates from CO2 and diols

图式15. 电生NHCs活化CO2与邻二醇反应合成环状碳酸酯

Scheme 15. Electrogenerated NHCs activate CO2 and react with adjacent diols to synthesize cyclic carbonates

图式16. 电生氰甲基负离子催化二元醇与CO2合成环状碳酸酯的机理

Scheme 16. Mechanism of cyclic carbonate from ethylene diols and CO2 catalyzed by electrogenerated cyanomethyl anion

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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

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

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