Heterogeneous Catalytic Fixation of Carbon Dioxide for Synthesis of Carbonyl Derivatives

doi:10.6023/cjoc202405033

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (10): 3077-3090.DOI: 10.6023/cjoc202405033 Previous Articles Next Articles

Special Issue: 二氧化碳专题合集

REVIEWS

异相催化固定二氧化碳合成羰基衍生物的研究进展

张誉元, 杨昌杰, 唐海涛, 潘英明^*()

广西师范大学化学与药学学院省部共建药用资源化学与药物分子工程国家重点实验室药用资源化学与药物分子工程教育部重点实验室广西民族药省部共建协同创新中心广西桂林 541004

收稿日期:2024-05-25 修回日期:2024-08-21 发布日期:2024-09-10
基金资助:
广西科技基地及人才项目(高层次创新人才及团队培养)(Guike AD23026094); 国家自然科学基金(22161008)

Heterogeneous Catalytic Fixation of Carbon Dioxide for Synthesis of Carbonyl Derivatives

Yuyuan Zhang, Changjie Yang, Haitao Tang, Yingming Pan^*()

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004

Received:2024-05-25 Revised:2024-08-21 Published:2024-09-10
Contact: *E-mail: panym@mailbox.gxnu.edu.cn
Supported by:
Guangxi Science and Technology Base and Talent Project (High Level Innovative Talents and Team Training)(Guike AD23026094); National Natural Science Foundation of China(22161008)

As an effective way to utilize CO₂ resources, multiphase catalytic carbon fixation is of great significance to promote carbon neutrality and carbon peak. The exploration of this reaction is of guiding significance to the establishment of other catalytic systems. This paper reviews the recent progress in the synthesis of a series of carbon dioxide fixed carbonyl derivatives by heterogeneous catalysis in the fields of photocatalysis, electrocatalysis, thermal catalysis, and photothermal catalysis. The synthesis of carbonyl derivatives by different heterogeneous catalysis CO₂, including organic carbonates, carbamates and carboxylic acids, is introduced. The reaction mechanism of these reactions is discussed. This provides a reference for the design and realization of the polyphase catalytic fixed CO₂ reaction.

Key words: heterogeneous catalysis, fixation of carbon dioxide, carbonyl derivatives

Cite this article

Yuyuan Zhang, Changjie Yang, Haitao Tang, Yingming Pan. Heterogeneous Catalytic Fixation of Carbon Dioxide for Synthesis of Carbonyl Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3077-3090.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 18

Figure 1. Heterogeneous catalytic synthesis of carbonyl derivatives from carbon dioxide

Figure 2. CuAg NWs fixes CO2 to produce carboxylic acids

Figure 3. Ag-CeO2 NWs fixed CO2 to produce phenyllactic acid

Figure 4. Cu-SnO2 reduces CO2 to formic acid

Figure 5. HNSs fixed CO2 to produce cyclic carbonates

Figure 6. d-BCN fixed CO2 to produce carboxylic acids

Figure 7. OH-P[5]-on-COF fixed CO2 to produce cyclic carbonates

Figure 8. Mg-NC fixed CO2 to produce cyclic carbonates

Figure 9. CTO fixed CO2 to produce N-methylformylanilide

Figure10. Au-MOFs fixed CO2 to produce carboxylic acids

Figure 11. POMP-NHC-Ir fixed CO2 to produce amide compound

Figure 12. Ir1-WO3 fixed CO2 to produce cyclic carbonates

Figure 13. {(ME2NH2)2[Co3(BCP)2]?6H2O?4DMF}n fixed CO2 to produce oxazolidinones

Figure 14. PIL-s1-HCO3 fixed CO2 to produce formamide products

Figure 15. Cu@NHC-1 fixed CO2 to produce oxazolidinones

Figure 16. Ag@POP-NL-3 fixed CO2 to produce cyclic carbonate ester

Figure 17. Photocatalytic reduction of CO2 via CdS/VS-MoS2

Figure 18. CoFe2O4@TPA fixes CO2 to produce carbonate under photothermal conditions

References 58

[1]	Liu, L.-C.; Corma, A. Chem. Rev. 2023, 123, 4855.
[2]	Huang, W.-Y.; Wang, G.-Q.; Li, W.-H.; Li, T.-T.; Ji, G.-J.; Ren, S.-C.; Jiang, M.; Yan, L.; Tang, H.-T.; Pan, Y.-M.; Ding, Y.-J. Chem 2020, 6, 2300.
[3]	Jia, J.-S.; Cao, Y.; Wu, T.-X.; Tao, Y.; Pan, Y.-M.; Huang, F.-P.; Tang, H.-T. ACS Catal. 2021, 11, 6944.
[4]	Kisch, H. Angew. Chem., Int. Ed. 2010, 49, 9588.
[5]	Jaramillo, T. F.; Jørgensen, K. P.; Bonde, J.; Nielsen, J. H.; Horch, S.; Chorkendorff, I. Science 2007, 317, 100. pmid: 17615351
[6]	Wang, X.-S.; Yang, X.; Chen, C.-H.; Li, H.-F.; Huang, Y.-B.; Cao, R. Acta Chim. Sinica 2022, 80, 22. (in Chinese)
	(王旭生, 杨胥, 陈春辉, 李红芳, 黄远标, 曹荣, 化学学报, 2022, 80, 22.) doi: 10.6023/A21100455
[7]	Xiong, T.-K.; Zhou, X.-Q.; Zhang, M.; Tang, H.-T.; Pan, Y.-M.; Liang, Y. Green Chem. 2021, 23, 4328.
[8]	Xie, Y.-Y.; Pan, Y.-M. Green Chem. 2024, DOI: 10.1039/D4GC02829E.
[9]	Pan, Y.-Z.; Qi, X.; Zhu, J.-X.; Wang, Y.-C.; Liang, Y.; Wang, H.-S; Tang, H.-T.; Pan, Y.-M. Org. Lett. 2022, 24, 8239.
[10]	Sun, G.-Q.; Yu, P.; Zhang, W.; Zhang, W.; Wang, Y.; Liao, L.-L.; Zhang, Z.; Li, L.; Lu, Z.-P.; Yu, D.-G.; Lin, S. Nature 2023, 615, 67.
[11]	Ertl, G. Angew. Chem., Int. Ed. 2008, 47, 3524.
[12]	Centi, G.; Perathoner, S. Catal. Today 2009, 148, 191.
[13]	Aresta, M.; Dibenedetto, A.; Angelini, A. J. CO₂ Util. 2014, 3-4, 65.
[14]	Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933.
[15]	Peters, M.; Köhler, B.; Kuckshinrichs, W.; Leitner, W.; Markewitz, P.; Müller, T. E. ChemSusChem 2011, 4, 1216.
[16]	Kondratenko, E. V.; Mul, G.; Baltrusaitis, J.; Larrazábal, G. O.; Pérez-Ramírez, J. Energy Environ. Sci. 2013, 6, 3112.
[17]	Qiao, J.-L.; Liu, Y.-Y.; Hong, F.; Zhang, J.-J. Chem. Soc. Rev. 2014, 43, 631.
[18]	Tao, Z.; Rooney, C. L.; Liang, Y.; Wang, H. J. Am. Chem. Soc. 2021, 143, 19630.
[19]	Fu, X.; Zhang, J.; Kang, Y. React. Chem. Eng. 2021, 6, 612.
[20]	Hori, Y.; Kikuchi, K.; Suzuki, S. Chem. Lett. 1985, 14, 1695.
[21]	Isse, A. A.; Durante, C.; Gennaro, A. Electrochem. Commun. 2011, 13, 810.
[22]	Zhang, Y.; Yu, S.; Luo, P.; Xu, S.; Zhang, X.; Zhou, H.; Du, J.; Yang, J.; Xin, N.; Kong, Y.; Liu, J.; Chen, B.; Lu, J. R. Soc. Open Sci. 2018, 5, 180897.
[23]	Cao, Y.-M.; Li, D.-Y.; Ding, C.-M.; Ye, S.; Zhang, X.-W.; Chi, H.-B.; Liu, L.-Q.; Liu, Y.; Xiao, J.-P.; Li, C. ACS Catal. 2023, 13, 11902.
[24]	Peng, X.; Karakalos, S. G.; Mustain, W. E. ACS Appl. Mater. Interfaces 2018, 10, 1734.
[25]	Li, Z.-Y.; Yang, Y.-S.; Wei, M. Acta Chim. Sinica 2022, 80, 199. (in Chinese)
	(李泽洋, 杨宇森, 卫敏, 化学学报, 2022, 80, 199.) doi: 10.6023/A21110493
[26]	Jiang, G.-M.; Su, Y.-P.; Li, H.-X.; Chen, Y.-F.; Li, S.; Bu, Y.-B.; Zhang, Z.-T. Appl. Surf. Sci. 2021, 549, 149277.
[27]	Rao, R.-C.; Shao, F.-L.; Dong, X.-Z.; Dong, H.-Z.; Fang, S.; Sun, H.; Ling, Q. Appl. Surf. Sci. 2020, 513, 145771.
[28]	Naqvi, S. T. R.; Shirinfar, B.; Majeed, S.; Najam-Ul-Haq, M.; Hussain, D.; Iqbal, T.; Ahmed, N. Analyst 2018, 143, 5610.
[29]	Guan, A.; Quan, Y.; Chen, Y.; Liu, Z.; Zhang, J.; Kan, M.; Zhang, Q.; Huang, H.; Qian, L.; Zhang, L.; Zheng, G. Chin. J. Catal. 2022, 43, 3134.
[30]	Jiang, Y.-L.; Li, G.-C.; Chen, Q.-S.; Xu, Z.-N.; Lin, S.-S.; Guo, G.-C. Acta Chim. Sinica 2022, 80, 703. (in Chinese)
	(蒋银龙, 李国超, 陈青松, 徐忠宁, 林姗姗, 郭国聪, 化学学报, 2022, 80, 7037.)
[31]	Ren, B.; Wen, G.; Gao, R.; Luo, D.; Zhang, Z.; Qiu, W.; Ma, Q.; Wang, X.; Cui, Y.; Ricardez-Sandoval, L.; Yu, A.; Chen, Z. Nat. Commun. 2022, 13, 2486.
[32]	Álvarez, A.; Bansode, A.; Urakawa, A.; Bavykina, A. V.; Wezendonk, T. A.; Makkee, M.; Gascon, J.; Kapteijn, F. Chem. Rev. 2017, 117, 9804. doi: 10.1021/acs.chemrev.6b00816 pmid: 28656757
[33]	Jiang, Y.-L.; Shan, J.-Q.; Wang, P.-T.; Huang, L.-S.; Zheng, Y.; Qiao, S.-Z. ACS Catal. 2023, 13, 3101.
[34]	Hao, Y.; Yan, X.; Liu, X.; Qin, S.; Zhu, Z.; Panchal, B.; Chang, T. J. CO₂ Util. 2022, 56, 101867.
[35]	Guo, L.; Zhang, R.; Xiong, Y.; Chang, D.; Zhao, H.; Zhang, W.; Zheng, W.; Chen, J.; Wu, X. Molecules 2020, 25, 3627.
[36]	Dai, X.-Y.; Qi, K.; Liu, C. Carbon 2023, 202, 1.
[37]	Li, D.; Kassymova, M.; Cai, X.; Zang, S.; Jiang, H. Coord. Chem. Rev. 2020, 412, 213262.
[38]	Lu, Q.; Eid, K.; Li, W.; Abdullah, A. M.; Xu, G.; Varma, R. S. Green Chem. 2021, 23, 5394.
[39]	Li, L.; Dai, X.; Chen, D.-L.; Zeng, Y.; Hu, Y.; Lou, D. Angew. Chem., Int. Ed. 2022, 61, 202205839.
[40]	Gong, E.; Ali, S.; Hiragond, C. B.; Kim, H. S.; Powar, N. S.; Kim, D.; Kim, H.; In, S.-I. Energy Environ. Sci. 2022, 15, 880.
[41]	Inoue, T.; Fujishima, A.; Konishi, S. Nature 1979, 277, 637.
[42]	Yuan, T.; Wu, Z.-W.; Zhai, S.-M.; Wang, R.; Wu, S.-T.; Cheng, J.-J.; Zheng, M.-F.; Wang, X.-C. Angew. Chem., Int. Ed. 2023, 62, e20230486.
[43]	Li, X.-J.; Niu, X.-X.; Fu, P.; Song, Y.-R. Appl. Catal. B 2024, 350, 123943.
[44]	Li, L.; Liu, W.-X.; Ying, H.-H.; He, X.; Shang, S.; Zhang, P.; Zhang, X.-D.; Liu, S.-H.; Wang, H.; Xie, Y. CCS Chem. 2024, DOI: 10.31635/ccschem.024.202404189.
[45]	Yuan, S.-B.; Bai, P.; He, Y.; Chen, J.-F.; Zhao, Y.-C.; Li, Y.-D. J. CO₂ Util. 2023, 71, 102453.
[46]	Yang, Z.-Y.; Shen, C.-R.; Dong, K.-W. Chin. J. Chem. 2022, 40, 2734.
[47]	Wei, R.-J.; Xie, M.; Xia, R.-Q.; Chen, J.; Hu, H.-J.; Ning, G.-H.; Li, D. J. Am. Chem. Soc. 2023, 145, 22720.
[48]	Shen, Y.-J.; Zheng, Q.-S.; Chen, Z.-N.; Wen, D.-H.; James, H. C.; Xu, X.; Tu, T. Angew. Chem., Int. Ed. 2021, 60, 4125.
[49]	Xu, J.; Xu, H.; Dong, A.-Q.; Zhang, H. Adv. Mater. 2022, 34, 2206991.
[50]	Zhou, X.-Q.; Tang, H.-T.; Cui, F.-H.; Liang, Y.; Li, S.-H.; Pan, Y.-M. Green Chem. 2023, 25, 5024.
[51]	Xiong, T.-K.; Xia, Q.; Zhou, X.-Q.; Li, S.-H.; Cui, F.-H.; Tang, H.-T.; Pan, Y.-M.; Liang, Y. Adv. Synth. Catal. 2023, 365, 2183.
[52]	Pan, Y.-Z.; Xia, Q.; Zhu, J.-X.; Wang, Y.-C.; Wang, H.-S.; Tang, H.-T.; Pan, Y.-M. Org. Lett. 2022, 24, 8239.
[53]	Jiao, Z.-H.; Zhao, X.-Y.; Zhao, J. Acta Phys.-Chim. Sin. 2023, 39, 2301018.
[54]	Chen, P.-B.; Tang, X.-Y.; Meng, X.-J.; Tang, H.-T.; Liang, Y.; Pan, Y.-M. Green Synth. Catal. 2022, 3, 162.
[55]	Rao, Z.-X.; Chen, P.-B.; Xu, J.; Wang, Q.; Tang, H.-T.; Liang, Y.; Pan, Y.-M. ChemSusChem 2023, e202300170.
[56]	Chen, P.-B.; Yang, J.-W.; Rao, Z.-X.; Wang, Q.; Tang, H.-T.; Liang, Y.; Pan, Y.-M. J. Colloid Interf. Sci. 2023, 652, 866.
[57]	Liu, C.-Y.; Xiao, Y.-J.; Wan, W.-R.; Wei, Y. Appl. Catal. B 2023, 325, 122394.
[58]	Zhang, L.-P.; Tu, X.-W.; Chen, Y.-T.; Han, W.-H. Mol. Catal. 2023, 538, 112971.

异相催化固定二氧化碳合成羰基衍生物的研究进展

Heterogeneous Catalytic Fixation of Carbon Dioxide for Synthesis of Carbonyl Derivatives

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 18

References 58

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Siyi Mi, Longlong Ma, Jianguo Liu. Research Progress of Continuous Flow Selective Hydrogenation Technology [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1445-1457.
[2]	Xiaolin Jiang, Chaoyang Wang, Liyuan Wu, Yuehui Li. Advances in Catalytic Conversion of CO₂ with Carbazole-Based Molecules and Polymers [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1423-1444.
[3]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[4]	Shiguo Ou, Ruirui Chai, Jiahao Li, Dawei Wang, Xinxin Sang. Metal-Organic Framework Derived Phytate-Iron for Efficient Synthesis of 2-Arylbenzoxazole via Hydrogen Transfer Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2934-2945.
[5]	Xu Liao, Zeyu Wang, Wufei Tang, Jinqing Lin. Progress in Porous Organic Polymer for Chemical Fixation of Carnbon Dioxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2699-2710.
[6]	Baichuan Mo, Chunxia Chen, Jinsong Peng. Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1215-1240.
[7]	Rui Bai, Xujuan Liu, Wenyu Luo, Shanshan Liu, Linyu Jiao. Research Progress of Chan-Lam Coupling Reaction in Heterogeneous Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2342-2354.
[8]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[9]	Qiang Huang, Tingting Deng, Jiayun Zhu, Jun Li, Feifei Li. Study on the Green Synthesis of β-Hydroxy-1,2,3-triazoles Catalyzed by An Amino-Functionalized Graphene-Supported Ag-Cu Composites [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 534-542.
[10]	Yaoyao Zhang, Lijie Zhou, Biao Han, Weishuang Li, Bojie Li, Lei Zhu. Research Progress of Chitosan Supported Copper Catalyst in Organic Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 33-53.
[11]	Xin Chen, Chunxia Chen, Jinsong Peng. Research Progress of Cellulose and Its Derivatives Supported Copper Catalyst Catalyzed Organic Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1319-1336.
[12]	Li Cheng, Wenrong Wang, Yuqian Sun, Tuanjie Li, Chenxia Yu, Changsheng Yao. N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1607-1613.
[13]	Yuxuan Chen, Qi Chen, Zhanhui Zhang. Application of Covalent Organic Framework Materials as Heterogeneous Ligands in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3826-3843.
[14]	Feiyu Wang, Zhipeng Zhang, Fei Huang. Research Progress of O—H Insertion Reaction Based on Diazo Ester [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 144-157.
[15]	Xu Zi-Yue, Luo Yi, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Porous Organic Polymers as Heterogeneous Catalysts for Visible Light-Induced Organic Transformations [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3777-3793.