有机化学 ›› 2024, Vol. 44 ›› Issue (10): 3091-3105.DOI: 10.6023/cjoc202406044 上一篇 下一篇
综述与进展
许立锋a, 武安国a, 于芳羽a, 李红茹a,b,*(), 何良年a,*()
收稿日期:
2024-06-28
修回日期:
2024-07-24
发布日期:
2024-08-30
基金资助:
Lifeng Xua, Anguo Wua, Fangyu Yua, Hongru Lia,b,*(), Liangnian Hea,*()
Received:
2024-06-28
Revised:
2024-07-24
Published:
2024-08-30
Contact:
*E-mail: Supported by:
文章分享
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.
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.
Entry | Epoxide (n/mmol) | Catalyst (dosage) | TBAB/mol% | Solvente (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 | [ |
2 | Propylene oxide (3) | Ti18Bi4O29Bz26 (20 μmol) | 1.6 | 14 h, 300 W Xe lamp | >99 | [ | |
3b | Propylene oxide (1.4) | BiNbO4/r-GO (50 mg) | 2 | S1/S2 (10/2) | 24 h, 300 W Hg lamp | 65 | [ |
4c | Propylene oxide (1.4) | FeNbO4/r-GO (50 mg) | 2 | S1/S2 (4/1) | 24 h, 500 W Hg lamp | 57 | [ |
5 | Phenyl oxirane (44) | W18O49/g-C3N4 (30 mg) | 2.5 | 4 h, 300 W Xe lamp | 60 | [ | |
6 | Propylene oxide (71) | g-C3N4/Ag (10 mg) | 0.7 | 6 h, 300 W Xe lamp | [ | ||
7 | Phenyl oxirane (0.15) | Pd/SCNT-500 (10 mg) | 67 | 24 h, 0.15w/cm2 455nm | 97 | [ | |
8d | Propylene oxide (10) | Zr-Thia/g-CN (50 mg) | 2.5 | 30 h, 250w Hg lamp | 90.8 | [ | |
9c | Propylene oxide (1.4) | BiNbO4/NH2-MIL-125(Ti) (50 mg) | 2 | S1/S2 (5/1) | 72 h, 300 W Hg lamp | 74 | [ |
10c | Propylene oxide (1.4) | FeNbO4/NH2-MIL-125(Ti) (50 mg) | 2 | S1/S2 (4/1) | 72 h, 300 W Hg lamp | 52 | [ |
11 | Propylene oxide (4.5) | Bi-PCN-224 (30 mg) | 11 | 6 h, 300 W Xe lamp | 99 | [ | |
12 | Propylene oxide (0.1) | UiO-bpydc (Zn) (20 mg) | 500 | S3 (3) | 9 h, 300 W Xe lamp | 90 | [ |
13 | Epichlorohydrin (20) | PCN-224 (Mg) (0.5 mmol) | 1 | 6 h, LED light (3*30 W) | 99 | [ | |
14 | Epichlorohydrin (38) | Fe-BDC (15 mg) | 0.8 | 4 h, 300 W Xe lamp | 45 | [ | |
15 | Epichlorohydrin (12.75) | Fe-DBP (10 mg) | 8 | 12 h, 1000 W Xe lamp. | 97 | [ | |
16 | Epichlorohydrin (0.2) | TpPa-1 (5 mg) | 5 | S1 (5) | 8 h, Blue light 455nm | 82 | [ |
17 | Propylene oxide (0.25) | OH-P [5]-on-COF (1.5 mg) | 5 | 8 h, LED lamp | 99 | [ | |
18 | Epichlorohydrin (1) | 9,10-Anthraquinone (10 mol%) | 10 | S1 (10) | 12 h, 20 W LED | 93 | [ |
Entry | Epoxide (n/mmol) | Catalyst (dosage) | TBAB/mol% | Solvente (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 | [ |
2 | Propylene oxide (3) | Ti18Bi4O29Bz26 (20 μmol) | 1.6 | 14 h, 300 W Xe lamp | >99 | [ | |
3b | Propylene oxide (1.4) | BiNbO4/r-GO (50 mg) | 2 | S1/S2 (10/2) | 24 h, 300 W Hg lamp | 65 | [ |
4c | Propylene oxide (1.4) | FeNbO4/r-GO (50 mg) | 2 | S1/S2 (4/1) | 24 h, 500 W Hg lamp | 57 | [ |
5 | Phenyl oxirane (44) | W18O49/g-C3N4 (30 mg) | 2.5 | 4 h, 300 W Xe lamp | 60 | [ | |
6 | Propylene oxide (71) | g-C3N4/Ag (10 mg) | 0.7 | 6 h, 300 W Xe lamp | [ | ||
7 | Phenyl oxirane (0.15) | Pd/SCNT-500 (10 mg) | 67 | 24 h, 0.15w/cm2 455nm | 97 | [ | |
8d | Propylene oxide (10) | Zr-Thia/g-CN (50 mg) | 2.5 | 30 h, 250w Hg lamp | 90.8 | [ | |
9c | Propylene oxide (1.4) | BiNbO4/NH2-MIL-125(Ti) (50 mg) | 2 | S1/S2 (5/1) | 72 h, 300 W Hg lamp | 74 | [ |
10c | Propylene oxide (1.4) | FeNbO4/NH2-MIL-125(Ti) (50 mg) | 2 | S1/S2 (4/1) | 72 h, 300 W Hg lamp | 52 | [ |
11 | Propylene oxide (4.5) | Bi-PCN-224 (30 mg) | 11 | 6 h, 300 W Xe lamp | 99 | [ | |
12 | Propylene oxide (0.1) | UiO-bpydc (Zn) (20 mg) | 500 | S3 (3) | 9 h, 300 W Xe lamp | 90 | [ |
13 | Epichlorohydrin (20) | PCN-224 (Mg) (0.5 mmol) | 1 | 6 h, LED light (3*30 W) | 99 | [ | |
14 | Epichlorohydrin (38) | Fe-BDC (15 mg) | 0.8 | 4 h, 300 W Xe lamp | 45 | [ | |
15 | Epichlorohydrin (12.75) | Fe-DBP (10 mg) | 8 | 12 h, 1000 W Xe lamp. | 97 | [ | |
16 | Epichlorohydrin (0.2) | TpPa-1 (5 mg) | 5 | S1 (5) | 8 h, Blue light 455nm | 82 | [ |
17 | Propylene oxide (0.25) | OH-P [5]-on-COF (1.5 mg) | 5 | 8 h, LED lamp | 99 | [ | |
18 | Epichlorohydrin (1) | 9,10-Anthraquinone (10 mol%) | 10 | S1 (10) | 12 h, 20 W LED | 93 | [ |
Entry | Catalystb | Zn form | Reaction condition | Light intensitya | 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 | [ |
2 | Zn SA-NC | Zn atom | 100 kPa CO2, 16 h | 300 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 99 | [ |
3 | ZNC-800 | Zn atom | 100 kPa CO2, 10 h | 1000 mW•cm–2 | 4-Methyl-1,3-dioxolan-2-one | 94 | [ |
4 | Zn-Asp-300 | ZnO | 100 kPa CO2, 4 h | 152.5 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 92 | [ |
5 | ZNPC-600 | ZnO | 100 kPa CO2, 6 h | 500 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 99 | [ |
6 | ZnS / NPC-2 | ZnS | 100 kPa CO2, 12 h | 300 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 98 | [ |
7 | ZnO/NC-L | ZnO | 100 kPa CO2, 6 h | 120 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 76 | [ |
Entry | Catalystb | Zn form | Reaction condition | Light intensitya | 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 | [ |
2 | Zn SA-NC | Zn atom | 100 kPa CO2, 16 h | 300 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 99 | [ |
3 | ZNC-800 | Zn atom | 100 kPa CO2, 10 h | 1000 mW•cm–2 | 4-Methyl-1,3-dioxolan-2-one | 94 | [ |
4 | Zn-Asp-300 | ZnO | 100 kPa CO2, 4 h | 152.5 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 92 | [ |
5 | ZNPC-600 | ZnO | 100 kPa CO2, 6 h | 500 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 99 | [ |
6 | ZnS / NPC-2 | ZnS | 100 kPa CO2, 12 h | 300 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 98 | [ |
7 | ZnO/NC-L | ZnO | 100 kPa CO2, 6 h | 120 mW•cm–2 | 4-Chloromethyl-1,3-dioxolan-2-one | 76 | [ |
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 | [ |
2 | Cu|Mg/Al | [BMlm][BF4] | r.t., 100 kPa | Propylene oxide | 92 | [ | |
3 | CuNPs|Mg | 0.1 mol/L TEAI | MeCN | 25 ℃, 100 kPa | Propylene oxide | 86 | [ |
4 | Cu/CS|Mg | 0.1 mol/L TEAI | MeCN | r.t., 100 kPa | Propylene oxide | 94.7 | [ |
5 | AgNPs|Mg | 0.1 mol/L TEAI | MeCN | 25 ℃, 100 kPa | Propylene oxide | 70 | [ |
6 | Ss|Mg | TBAI | MeCN | r.t., 100 kPa | (R)-Styrene oxide | 59 (91% ee) | [ |
7 | C|Pt | TBAP, Ni(Ⅱ) complex | MeCN | r.t., 100 kPa | Styrene oxide | 100 | [ |
8 | Cu(ND)/CP|Pt | ZnCl2, TBAB | MeCN | r.t., 100 kPa | Styrene oxide | 74.9 | [ |
9 | HNSs|Pt | ZnCl2, TBAB | MeCN | r.t., 100 kPa | Styrene oxide | 66.9 | [ |
10 | Ti/TiO2-CNT-Pt|C | [APMIm]DCA | MeCN | 50 ℃, 100 kPa | Styrene oxide | 95 | [ |
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 | [ |
2 | Cu|Mg/Al | [BMlm][BF4] | r.t., 100 kPa | Propylene oxide | 92 | [ | |
3 | CuNPs|Mg | 0.1 mol/L TEAI | MeCN | 25 ℃, 100 kPa | Propylene oxide | 86 | [ |
4 | Cu/CS|Mg | 0.1 mol/L TEAI | MeCN | r.t., 100 kPa | Propylene oxide | 94.7 | [ |
5 | AgNPs|Mg | 0.1 mol/L TEAI | MeCN | 25 ℃, 100 kPa | Propylene oxide | 70 | [ |
6 | Ss|Mg | TBAI | MeCN | r.t., 100 kPa | (R)-Styrene oxide | 59 (91% ee) | [ |
7 | C|Pt | TBAP, Ni(Ⅱ) complex | MeCN | r.t., 100 kPa | Styrene oxide | 100 | [ |
8 | Cu(ND)/CP|Pt | ZnCl2, TBAB | MeCN | r.t., 100 kPa | Styrene oxide | 74.9 | [ |
9 | HNSs|Pt | ZnCl2, TBAB | MeCN | r.t., 100 kPa | Styrene oxide | 66.9 | [ |
10 | Ti/TiO2-CNT-Pt|C | [APMIm]DCA | MeCN | 50 ℃, 100 kPa | Styrene oxide | 95 | [ |
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