Citation: Dana Bílková, Petr Jansa, Iva Paterová, Libor Červený. Hydrogenation of coumarin to octahydrocoumarin over a Ru/Ccatalyst[J]. Chinese Journal of Catalysis, ;2015, 36(7): 957-960. doi: 10.1016/S1872-2067(15)60860-9 shu

Hydrogenation of coumarin to octahydrocoumarin over a Ru/Ccatalyst

1.
a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;

Corresponding author: Dana Bílková,
Received Date: 3 January 2015
Available Online: 8 April 2015
Fund Project: This work was supported by specific university research (MSMT No. 20/2014). (MSMT No. 20/2014)

The production of octahydrocoumarin, which can serve as a replacement for toxic coumarin, was investigated using 5% Ru on active carbon (Ru/C) as the catalyst for the hydrogenation of coumarin. The hydrogenation was studied by optimizing the reaction conditions (pressure, solvent and coumarin concentration). The activity and selectivity of the Ru/C catalyst were compared for different solvents. The mechanism of coumarin hydrogenation was deduced. The formation of side products was explained. The optimal hydrogenation reaction conditions were: 130 ℃, 10 MPa, 60 wt% coumarin in methanol, and 0.5 wt% (based on coumarin) of Ru/C catalyst. At the complete conversion of coumarin, the selectivity to the desired product was 90%.
- Hydrogenation,
- Coumarin,
- Octahydrocoumarin,
- Supported ruthenium catalyst,
- Selectivity
1. [1]
  [1] Vonášek F, Trepková E, Novotný L. Aromatic and Taste Substances. Praha/Bratislava: SNTL/Alfa, 1987, ISBN 04-810-87
2. [2]
  [2] Lake B G. Food Chem Toxicol, 1999, 37: 423
3. [3]
  [3] Riehl T F Jr, Kennedey J E Jr. DE Patent 2023914. 1970
4. [4]
  [4] Ye Z S, Shi L, Zhou Y G. Synlett, 2014, 25: 928
5. [5]
  [5] Gebauer-Henke E, Tomkins P, Leitner W, Müller T E. ChemCatChem, 2014, 6: 2910
6. [6]
  [6] Hattori T, Ida T, Tsubone A, Sawama Y, Monguchi Y, Sajiki H. Eur J Org Chem, 2015, 2015: 2492
7. [7]
  [7] Kuhn W, Funk H U, Senft G. WO Patent 2002018360A1. 2002
8. [8]
  [8] Ulgheri F, Marchetti M, Piccolo O. J Org Chem, 2007, 72: 6056
9. [9]
  [9] Semeniuchenko V, Groth U, Khilya V. Synthesis, 2009: 3533
10. [10]
  [10] Frank R L, Pierle R C. J Am Chem Soc, 1951, 73: 724
11. [11]
  [11] House H O, Carlson R G, Babad H. J Org Chem, 1963, 28: 3359
12. [12]
  [12] Alekseeva N A, Kolomeer G G, Maksutova I V, Minkovskij M M, Filatova T I. RU Patent 2059632C1. 1996
13. [13]
  [13] Koji I, Shin T. US Patent 5639893. 1997
14. [14]
  [14] de Benneville P L, Connor R. J Am Chem Soc, 1940, 62: 283
15. [15]
  [15] Pikna R. Diploma Thesis: Hydrogenation of Coumarin. ICT Prague, 2012
1. [1]
  Yajun Gao , Xinyu Yang , Jian Su , Zhizhong Li . A stable scandium(III) metal-organic framework with introduced nitrate ions for enhancing C₂H₆/C₂H₄ selectivity in the separation of MTO products. Chinese Journal of Structural Chemistry, 2025, 44(6): 100576-100576. doi: 10.1016/j.cjsc.2025.100576
2. [2]
  Yan Zhao , Zhenming Tian , Qisen Jia , Ting Yao , Jiashu Li , Yanan Wang , Xuejing Cui , Jing Liu , Xin Chen , Luhua Jiang . Crystal orientation dependent charge transfer dynamics and interfacial water configuration boosting photoelectrocatalytic water oxidation to H2O2. Chinese Journal of Structural Chemistry, 2025, 44(7): 100619-100619. doi: 10.1016/j.cjsc.2025.100619
3. [3]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
4. [4]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
5. [5]
  Wenchao Chen , Xiaoting Niu , Xinyu Liang , Guanghao Zhu , Xue Zhang , Qing Gong , Cen Xie , Guangbo Ge , Ping Wang , Yuqi He . Rationally engineered a universal far-red fluorogenic substrate of bile salt hydrolase for functional imaging and inhibitor screening. Chinese Chemical Letters, 2026, 37(4): 111320-. doi: 10.1016/j.cclet.2025.111320
6. [6]
  Lingyun Shen , Shenxiang Yin , Qingshu Zheng , Zheming Sun , Wei Wang , Tao Tu . A rechargeable and portable hydrogen storage system grounded on soda water. Chinese Chemical Letters, 2025, 36(3): 110580-. doi: 10.1016/j.cclet.2024.110580
7. [7]
  Zunjie Zhang , Mengran Liu , Bingcheng Ge , Tianfang Yang , Shuaitong Wang , Yang Liu , Shuyan Gao . In-situ reconstructed Cu/NiO nanosheets synergistically boosting nitrate electroreduction to ammonia. Chinese Chemical Letters, 2025, 36(8): 110657-. doi: 10.1016/j.cclet.2024.110657
8. [8]
  Zimo Yang , Yan Tong , Yongbo Liu , Qianlong Liu , Zhihao Ni , Yuna He , Yu Rao . Developing selective PI3K degraders to modulate both kinase and non-kinase functions. Chinese Chemical Letters, 2024, 35(11): 109577-. doi: 10.1016/j.cclet.2024.109577
9. [9]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
10. [10]
  Junyi Yu , Yin Cheng , Anhong Cai , Xianfeng Huang , Qingrui Zhang . Synthetic Cu(Ⅲ) from copper plating wastewater for onsite decomplexation of Cu(Ⅱ)- and Ni(Ⅱ)-organic complexes. Chinese Chemical Letters, 2025, 36(2): 110549-. doi: 10.1016/j.cclet.2024.110549
11. [11]
  Weidan Meng , Yanbo Zhou , Yi Zhou . Green innovation unleashed: Harnessing tungsten-based nanomaterials for catalyzing solar-driven carbon dioxide conversion. Chinese Chemical Letters, 2025, 36(2): 109961-. doi: 10.1016/j.cclet.2024.109961
12. [12]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
13. [13]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
14. [14]
  Bo Li , Yuanzhe Cheng , Xuyang Ma , Dongxu Zhao , Yang Zhang , Yongxing Sun , Jia Chen , Li Wu , Liang Zhao , Hongdeng Qiu , Yujian He . Facile and scale-up synthesis of cyano-functionalized covalent organic frameworks for selective gold recovery. Chinese Chemical Letters, 2026, 37(1): 111134-. doi: 10.1016/j.cclet.2025.111134
15. [15]
  Yongli Zhao , Dingsheng Cao , Jie-Ping Wan , Yunyun Liu . Synthesis of 3-phosphinyl chromones via in situ iodination mediated C-H phosphination and the tunable synthesis of 2-phosphoryl chromanones. Chinese Chemical Letters, 2026, 37(1): 111740-. doi: 10.1016/j.cclet.2025.111740
16. [16]
  Lijuan Huang , Rui Gan , Xin Han , Meilin Sun , Li Chen , Wen Liu , Xiaoxin Zhang , Fei Pan . Peroxymonosulfate activation by Fe(Ⅲ)-phytate co-precipitation for efficient water treatment at circumneutral pH: The critical role of direct electron transfer. Chinese Chemical Letters, 2026, 37(5): 111840-. doi: 10.1016/j.cclet.2025.111840
17. [17]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
18. [18]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356
19. [19]
  Shaoming Dong , Yiming Niu , Yinghui Pu , Yongzhao Wang , Bingsen Zhang . Subsurface carbon modification of Ni-Ga for improved selectivity in acetylene hydrogenation reaction. Chinese Chemical Letters, 2024, 35(12): 109525-. doi: 10.1016/j.cclet.2024.109525
20. [20]
  Hua Liu , Jian Zhao , Qi Li , Xiang-Yu Zhang , Zhi-Wei Zheng , Kun Huang , Da-Bin Qin , Bin Zhao . Indium-captured zirconium-porphyrin frameworks displaying rare multi-selectivity for catalytic transfer hydrogenation of aldehydes and ketones. Chinese Chemical Letters, 2025, 36(6): 110593-. doi: 10.1016/j.cclet.2024.110593

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(772)
HTML views(43)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142