Skip to main content
SpringerLink
Log in

The Highly Effective Cobalt Based Metal–Organic Frameworks Catalyst for One Pot Oxidative Esterification Under Mild Conditions

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The cobalt-based metal organic frameworks (Co-MOFs) catalyst has been prepared with using terephthalic acid and 4,4′-bipyridine as organic linkers by facile solvothermal method for one pot oxidative esterification. The prepared catalyst was pyrolysed at different temperature and then applied for oxidation of aldehyde using molecular oxygen as benign oxidant under mild conditions. The Co-MOFs pyrolysed at 800 °C (denoted as Co-MOFs-800) catalyst exhibited excellent catalytic activity, selectivity and recyclability toward the oxidative esterification of benzaldehydes. Furthermore, it can be reused up to 5 runs without significant loss of activity.

Graphic Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 1
Fig. 8

Similar content being viewed by others

References

  1. Ogawa T, Matsui M (1976) J Am Chem Soc 98:1629–1630

    Article  CAS  Google Scholar 

  2. Wilson SR, Tofigh S, Misra RN (1982) J Org Chem 47:1360–1361

    Article  CAS  Google Scholar 

  3. Garegg PJ, Olsson L, Oscarson S (1995) J Org Chem 60:2200–2204

    Article  CAS  Google Scholar 

  4. Otera J, Nishikido J (2010) Esterification; methods, reactions, and applications, 2nd edn. Wiley-VCH, Weinheim

    Google Scholar 

  5. Smith MB, March J (1992) March’s advanced organic chemistry. Wiley, New York

    Google Scholar 

  6. Ning L, Liao S, Liu X, Guo P, Zhang Z, Zhang H, Tong X (2018) J Catal 364:1–3

    Article  CAS  Google Scholar 

  7. Fan C, Wang R, Kong P, Wang X, Wang J, Zhang X (2020) Catal Commun 140:106002

    Article  CAS  Google Scholar 

  8. Jun G, Guoli F, Lan Y, Xinzhong C, Peng Z, Feng L (2017) Chem Cat Chem 9:1230–1241

    Google Scholar 

  9. Yajuan H, Yanzhu C, Shuru L, Hengquan Y (2012) J Phys Chem C 116:6512–6519

    Article  CAS  Google Scholar 

  10. Ramakrishnan R, Kathiravan K, Sakthivel K, Sivakumar T (2016) RSC Adv 6:45907–45922

    Article  CAS  Google Scholar 

  11. Chih Hsiang T, Mengze X, Pranaw K, Brian TG (2018) Catal Today 306:81–88

    Article  CAS  Google Scholar 

  12. Singh S, Patel A, Prakashan P (2015) Appl Catal A 505:131–140

    Article  CAS  Google Scholar 

  13. Li Y, Wang L, Yan R, Han J, Zhang S (2015) Catal Sci Technol 5:3682–3692

    Article  CAS  Google Scholar 

  14. Wan X, Deng W, Zhang Q, Wang Y (2014) Catal Today 233:147–154

    Article  CAS  Google Scholar 

  15. Suzuki K, Yamaguchi T, Matsushita K, Iitsuka C, Miura J, Akaogi T, Ishida H (2013) ACS Catal 3:1845–1849

    Article  CAS  Google Scholar 

  16. Sanny V, Deepak V, Anil SK, Suman JL (2015) Appl Catal A 489:17–23

    Article  CAS  Google Scholar 

  17. Yasukawa T, Yang X, Kobayashi S (2018) Org Lett 20:5772–5776

    Article  CAS  Google Scholar 

  18. Xie J, Kammert JD, Kaylor N, Zheng JW, Choi E, Pham HN, Sang X, Stavitski E, Attenkofer K, Unocic RR, Datye AK, Davis RJ (2018) ACS Catal 8:3875–3884

    Article  CAS  Google Scholar 

  19. Cui X, Li Y, Bachmann S, Scalone M, Surkus AE, Junge K, Topf C, Beller M (2015) J Am Chem Soc 137:10652–10658

    Article  CAS  PubMed  Google Scholar 

  20. Su H, Zhang KX, Zhang B, Wang HH, Yu QY, Li XH, Antonietti M, Shen JS (2017) J Am Chem Soc 139:811–818

    Article  CAS  PubMed  Google Scholar 

  21. Feng Y, Jia W, Yan GH, Zeng XH, Sperry J, Xu BB, Sun Y, Tang X, Lei TZ, Lin L (2020) J Catal 381:811–818

    Google Scholar 

  22. Eisenberg D, Slot TK, Rothenberg G (2018) ACS Catal 8:8618–8629

    Article  CAS  Google Scholar 

  23. Slot TK, Eisenberg D, Rothenberg G (2018) Chem Cat Chem 10:2119–2124

    CAS  PubMed  Google Scholar 

  24. Astrakova TV, Sobolev VI, Koltunov KY (2020) Catal Commun 137:105952

    Article  CAS  Google Scholar 

  25. Cheng TY, Yu H, Peng F, Wang HG, Zhang BS, Su DS (2016) Catal Sci Technol 6:1007–1015

    Article  CAS  Google Scholar 

  26. Jagadeesh RV, Junge H, Pohl MM, Radnik J, Bruckner A, Beller M (2013) J Am Chem Soc 135:10776–10782

    Article  CAS  PubMed  Google Scholar 

  27. Tang C, Surkus AE, Chen F, Pohl MM, Agostini G, Schneider M, Junge H, Beller M (2017) Angew Chem Int Ed 56:16616–16620

    Article  CAS  Google Scholar 

  28. Wang X, Zhou J, Fu H, Li W, Fan X, Xin G, Zheng J, Li X (2014) J Mater Chem A 4:14064–14070

    Article  CAS  Google Scholar 

  29. Li X, Jiang Q, Dou S, Deng L, Huo J, Wang S (2016) J Mater Chem A 4:15836–15840

    Article  CAS  Google Scholar 

  30. Zheng W, Jiang X, Wang X, Kaneti YV, Chen Y, Liu J, Jiang JS, Yamauchi Y, Hu M (2017) Angew Chem Int Ed 56:8435–8440

    Article  CAS  Google Scholar 

  31. Jiewei L, Lianfen C, Hao C, Jianyong Z, Li Z, Cheng Yong S (2014) Chem Soc Rev 43:6011–6061

    Article  Google Scholar 

  32. Chen L, Chen H, Luque R, Li Y (2014) Chem Sci 5:3708–3714

    Article  CAS  Google Scholar 

  33. Sun CY, To WP, Wang XL, Chan KT, Su ZM, Che CM (2015) Chem Sci 6:7105–7111

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Gong YN, Ouyang T, He CT, Lu TB (2016) Chem Sci 7:1070–1075

    Article  CAS  PubMed  Google Scholar 

  35. Adeel CH, Nazir A, Hussein YA, Laypkovc A, Francis V (2015) Chem Soc Rev 44:6804–6849

    Article  Google Scholar 

  36. Huang YB, Liang J, Wang XS, Cao R (2017) Chem Soc Rev 46:126–157

    Article  CAS  PubMed  Google Scholar 

  37. Xuning L, Xiang H, Shibo X, Shu M, Jie D, Weizheng C, Song L, Xiaoli Y, Hongbin Y, Jiajian G, Junhu W, Yanqiang H, Tao Z, Bin L (2018) J Am Chem Soc 140:12469–12475

    Article  CAS  Google Scholar 

  38. Huirong C, Kui S, Junying C, Xiaodong C, Yingwei L (2017) J Mater Chem A 5:9937–9945

    Article  Google Scholar 

  39. Ming Z, Chaohai W, Chao L, Rui L, Jiansheng L, Xiuyun S, Jinyou S, Weiqin H, Lianjun W (2018) J Mater Chem A 6:11226–11235

    Article  Google Scholar 

  40. Feng J, Hailing G, Lei Z, Junjuan L, Yongming C, Svetlana M, Chenguang L (2019) Microporous Mesoporous Mater 276:98–106

    Article  CAS  Google Scholar 

  41. Guowu Z, Hua Chun Z (2017) ACS Catal 7:7509–7519

    Article  CAS  Google Scholar 

  42. Guihao Z, Dingxin L, Jianyong Z (2018) J Mater Chem A 6:1887–1899

    Article  Google Scholar 

  43. Guangli Y, Jian S, Faheem M, Pengyuan W, Guangshan Z (2014) RSC Adv 4:38804–38811

    Article  CAS  Google Scholar 

  44. Wei Z, Hongli L, Cuihua B, Shijun L, Yingwei L (2015) ACS Catal 5:1850–1856

    Article  CAS  Google Scholar 

  45. Yu Xiao Z, Yu Zhen C, Lina C, Junling L, Hai Long J (2015) Chem Commun 51:8292–8295

    Article  CAS  Google Scholar 

  46. Sun KK, Chen SJ, Li ZL, Lu GP, Cai C (2019) Green Chem 21:1602–1608

    Article  CAS  Google Scholar 

  47. Feng Y, Jia W, Yan G, Zeng X, Sperry J, Xu B, Sun Y, Tang X, Lei T, Lin L (2020) J Catal 381:570–578

    Article  CAS  Google Scholar 

  48. Alireza A, Mohammad S, Mahnaz N, Shokoofeh G (2017) J Mol Struct 1133:458–463

    Article  CAS  Google Scholar 

  49. Xu Y, Li B, Zheng S, Wu P, Zhan J, Xue H, Xu Q, Pang H (2018) J Mater Chem A 6:22070–22076

    Article  CAS  Google Scholar 

  50. Chao L, Taiqiang C, Weijing X, Xiaobing L, Likun P, Qun C, Bingwen H (2015) J Mater Chem A 3:5585–5591

    Article  CAS  Google Scholar 

  51. Tao J, Tong ML, Chen XM (2000). J Chem Soc Dalton Trans. https://doi.org/10.1039/b005438k

    Article  Google Scholar 

  52. Xu H (2008) Acta Cryst E64:m103

    Google Scholar 

  53. Kathiravan M, Thirusangumurugan S, Manzar S, Ahmad AS, Marga PM, Matthias B, Rajenahally JV (2018) Chem Sci 9:8553–8560

    Article  Google Scholar 

  54. Heejun P, Sojin O, Sujeong L, Sora C, Moonhyun O (2019) Appl Catal B 246:322–329

    Article  CAS  Google Scholar 

  55. Li W, Geng W, Liu L, Shang Q, Liu L, Kong X (2020) Sustain Energy Fuels 4:2043–2054

    Article  CAS  Google Scholar 

  56. Wang Z, Xiao S, Zhu Z, Long X, Zheng X, Lu X, Yang S (2015) ACS Appl Mater Interfaces 7(7):4048–4055

    Article  CAS  PubMed  Google Scholar 

  57. Liu Y, Jiang H, Zhu Y, Yang X, Li C (2016) J Mater Chem A 4:1694–1701

    Article  CAS  Google Scholar 

  58. Liua Y, Wanga C, Jua S, Lia M, Yuana A, Zhu G (2020) Prog Nat Sci Mater 30:185–191

    Article  CAS  Google Scholar 

  59. Wang T, Ma H, Liu X, Luo Y, Zhang S, Sun Y, Wang X, Gao J, Xu J (2019) Chem Asian J 14:1515–1522

    Article  CAS  PubMed  Google Scholar 

  60. Bai C, Li A, Yao X, Liu H, Li Y (2016) Green Chem 18:1061–1069

    Article  CAS  Google Scholar 

  61. Liu M, Zhang H, Wang J, Zhao G, Liu D (2020) React Kinet Mech Catal 129:865–881

    Article  CAS  Google Scholar 

  62. Vineeta P, Amer NA, Ahmed A, Brigitte S, Pascal R, Rabah B, Suman JL (2015) RSC Adv 5:88567–88573

    Article  CAS  Google Scholar 

  63. Hui S, Ke ZX, Bing Z, Hong WH, Qiu YY, Xin LH, Markus A, Jie CS (2017) J Am Chem Soc 139:811–818

    Article  CAS  Google Scholar 

  64. Rui T, Lu GP, Zhao X, Chen Z (2021) Chin Chem Lett 32:685–690

    Article  CAS  Google Scholar 

  65. Salazar A, Hunemorder P, Rabeah J, Quade A, Jagadeesh RV, Mejia E (2019) ACS Sustain Chem Eng 7:12061–12068

    CAS  Google Scholar 

  66. Zhou C, Tan Z, Jiang H, Zhang M (2018) Green Chem 20:1992–1997

    Article  CAS  Google Scholar 

  67. Jiang BL, Lin Y, Wang ML, Liu DS, Xu BH, Zhang SJ (2019) Org Chem Front 6:801–807

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the financial supports from the National Natural Science Foundation of China (NSFC 21333009, 21573244, 21573245), Chinese Academy of Sciences-Peking University Pioneer Cooperation Team and the Youth Innovation Promotion Association of CAS (2017049).

Author information

Authors and Affiliations

  1. School of Science, Department of Chemistry, University of Phayao, 19 Moo 2 Tambon Maeka Amphur, Mueang Phayao, 56000, Thailand

    Pagasukon Mekrattanachai, Naruemon Setthaya & Chakkresit Chindawong

  2. Beijing National Laboratory for Molecular Sciences, Laboratory of Molecular Nanostructures and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Lei Zhu & Wei Guo Song

  3. University of Chinese Academy of Sciences, Beijing, 100049, China

    Lei Zhu & Wei Guo Song

Authors
  1. Pagasukon Mekrattanachai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lei Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Naruemon Setthaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chakkresit Chindawong
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wei Guo Song
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Pagasukon Mekrattanachai or Wei Guo Song.

Ethics declarations

Conflict of interest

There are no conflicts to declare.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Electronic supplementary material 1 (DOCX 4580 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mekrattanachai, P., Zhu, L., Setthaya, N. et al. The Highly Effective Cobalt Based Metal–Organic Frameworks Catalyst for One Pot Oxidative Esterification Under Mild Conditions. Catal Lett 152, 1639–1650 (2022). https://doi.org/10.1007/s10562-021-03754-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-021-03754-x

Keywords

Search

Navigation