Skip to main content
SpringerLink
Log in

Direct synthesis of 3-picoline from 2-methylglutaronitrile over supported PdZn catalyst: promoting effects of Zn

  • Published:
Reaction Kinetics, Mechanisms and Catalysis Aims and scope Submit manuscript

Abstract

The promotion effect of transition metal on the catalytic performance of a Pd catalyst for the direct synthesis of 3-picoline from 2-methylglutaronitrile was investigated. The PdZn/SiO2–Al2O3 catalysts with appropriate Zn/Pd molar ratio exhibited a high 3-picoline yield. Kinetic and mechanism analysis revealed a kinetically relevant step of dehydrogenation in 3-methyltetrahydropyridine to 3-picoline involving the bound of 3-methyltetrahydropyridine to a Zn site and dehydrogenation by a vicinal Pd site to form 3-picoline. Such synergy between Zn and Pd sites accounted for the observed superiority of PdZn catalysts in direct synthesis of 3-picoline.

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
Scheme 1
Fig. 7

Similar content being viewed by others

References

  1. Shimizu S, Abe N, Iguchi A, Sato H (1998) Catal Surv Asia 2:71–76

    Article  CAS  Google Scholar 

  2. Rosas CB, Smith GB (1980) Chem Eng Sci 35:330–337

    Article  CAS  Google Scholar 

  3. Srinivas N, Radha Kishan M, Kulkarni SJ, Raghavan KV (2000) Microporous Mesoporous Mater 39:125–134

    Article  CAS  Google Scholar 

  4. Kalevaru VN, David Raju B, Venkat Rao V, Martin A (2009) Appl Catal A 352:223–233

    Article  CAS  Google Scholar 

  5. Reddy KRSK, Sreedhar I, Raghavan KV (2008) Appl Catal A 339:15–20

    Article  CAS  Google Scholar 

  6. Volf J, Pašek J (1986) Stud Surf Sci Catal 27:105–144

    Article  CAS  Google Scholar 

  7. Saito Y, Ishitani H, Ueno M, Kobayashi S (2017) ChemistryOpen 6:211–215

    Article  CAS  Google Scholar 

  8. De Bellefon C, Fouilloux P (1994) Catal Rev 36:459–506

    Article  Google Scholar 

  9. Cooper A, Bachiller-Baeza B, Anderson JA, Rodríguez-Ramos I, Guerrero-Ruiz A (2014) Catal Sci Technol 4:1446–1455

    Article  CAS  Google Scholar 

  10. Childers DJ, Schweitzer NM, Shahari SMK, Rioux RM, Miller JT, Meyer RJ (2014) J Catal 318:75–84

    Article  CAS  Google Scholar 

  11. Usamia Y, Kagawaa K, Kawazoea M, Matsumurab Y, Sakuraib H, Haruta M (1998) Appl Catal A 171:123–130

    Article  Google Scholar 

  12. Katano S, Kato HS, Kawai M, Domen K (2009) J Phys Chem C 113:14872–14878

    Article  CAS  Google Scholar 

  13. Ludwig W, Savara A, Schauermann S, Freund HJ (2010) ChemPhysChem 11:2319–2322

    Article  CAS  Google Scholar 

  14. Wang S, Gao K, Li W, Zhang J (2017) Appl Catal A 531:89–95

    Article  CAS  Google Scholar 

  15. Li X, Zhang B, Wu Q, Zhang C, Yu Y, Li Y, Lin W, Cheng H, Zhao F (2016) J Catal 337:284–292

    Article  CAS  Google Scholar 

  16. Nilsson M, Jansson K, Jozsa P, Pettersson LJ (2009) Appl Catal B 86:18–26

    Article  CAS  Google Scholar 

  17. Iwasa N, Yoshikawa M, Arai M (2002) Phys Chem Chem Phys 4:5414–5420

    Article  CAS  Google Scholar 

  18. Friedrich M, Penner S, Heggen M, Armbruster M (2013) Angew Chem 52:4389–4392

    Article  CAS  Google Scholar 

  19. Rameshan C, Stadlmayr W, Weilach C, Penner S, Lorenz H, Havecker M, Blume R, Rocha T, Teschner D, Knop-Gericke A, Schlogl R, Memmel N, Zemlyanov D, Rupprechter G, Klotzer B (2010) Angew Chem 49:3224–3227

    Article  CAS  Google Scholar 

  20. Dai C, Zhu S, Wang X, Zhang C, Zhang W, Li Y, Ning C (2017) New J Chem 41:3758–3765

    Article  CAS  Google Scholar 

  21. Suresh DD, DiCosimo, Loiseau R, Friedrich MS, Szabo HC (1991) United States Patent 5066809. 19 Nov 1991

  22. Vicerich MA, Oportus M, Benitez VM, Reyes P, Pieck CL (2014) Catal Lett 144:1178–1187

    Article  CAS  Google Scholar 

  23. Zhang Y, Zhou Y, Huang L, Zhou S, Sheng X, Wang Q, Zhang C (2015) Chem Eng J 270:352–361

    Article  CAS  Google Scholar 

  24. Berndt H, Lietz G, Lucke B, Volter J (1996) Appl Catal A 146:351–363

    Article  CAS  Google Scholar 

  25. Lente G (2013) ACS Catal 3:381–382

    Article  CAS  Google Scholar 

  26. Kozuch S, Martin JML (2012) ACS Catal 2:2787–2794

    Article  CAS  Google Scholar 

  27. Sun Q, Wang S, Liu H (2017) ACS Catal 7:4265–4275

    Article  CAS  Google Scholar 

  28. Liu G, Zeng L, Zhao Z-J, Tian H, Wu T, Gong J (2016) ACS Catal 6:2158–2162

    Article  Google Scholar 

  29. Ping H, Kou Z, Xu G, Wu S (2016) J Environ Chem Eng 4:3253–3259

    Article  CAS  Google Scholar 

  30. Burch R, Hayes MJ (1997) J Catal 165:249–261

    Article  CAS  Google Scholar 

  31. Li B, Wang J, Yuan Y, Ariga H, Takakusagi S, Asakura K (2011) ACS Catal 1:1521–1528

    Article  CAS  Google Scholar 

  32. Shen M, Yang M, Wang J, Wen J, Zhao M, Wan W (2009) J Phys Chem C 113:3212–3221

    Article  CAS  Google Scholar 

  33. Tew MW, Emerich H, van Bokhoven JA (2011) J Phys Chem C 115:8457–8465

    Article  CAS  Google Scholar 

  34. Shen L, Mao S, Li J, Li M, Chen P, Li H, Chen Z, Wang Y (2017) J Catal 350:13–20

    Article  CAS  Google Scholar 

  35. Jiang T, Huai Q, Geng T, Ying W, Xiao T, Cao F (2015) Biomass Bioenergy 78:71–79

    Article  CAS  Google Scholar 

  36. Kovnir K, Armbrüster M, Teschner D, Venkov TV, Szentmiklósi L, Jentoft FC, Knop-Gericke A, Grin Y, Schlögl R (2009) Surf Sci 603:1784–1792

    Article  CAS  Google Scholar 

  37. Wang Z, Yang L, Zhang R, Li L, Cheng Z, Zhou Z (2016) Catal Today 264:37–43

    Article  CAS  Google Scholar 

  38. Kovnir K, Armbrüster M, Teschner D, Venkov TV, Jentoft FC, Knop-Gericke A, Grin Y, Schlögl R (2007) Sci Technol Adv Mater 8:420–427

    Article  CAS  Google Scholar 

  39. Sanderson RT 2nd (ed) (1976) Chemical bonds and bond energy. Academic Press, New York

    Google Scholar 

  40. Lanini S, Prins R (1996) Appl Catal A 137:287–306

    Article  CAS  Google Scholar 

  41. Ronald LA, Wilmington DE (1990) United States Patent US 4935521. 19 Jun 1990

  42. Newson, JE, Truong S, Lonza AG (1986) Swiss Patent 654576A5. 28 Feb 1986

  43. Gerhard F, Gerald N, Basf AG (1988) United States Patent US 4755604. 5 Jul 1988

  44. Walter R, Basf AG (1988) United States Patent US 4762939. 9 Aug 1988

  45. Gerald G, Robert D. Reilly Industries Inc (1996) DE68926297. 19 Sep 1996

  46. Li Q, Zhang Y, Chen S, Fang W, Yang Y (2011) Chin J Catal 32:446–450

    Article  Google Scholar 

  47. Lai W, Xu Y, Zhao Y, Zheng J, Yi X, Fang W (2015) Reac Kinet Mech Cat 115:635–649

    Article  CAS  Google Scholar 

  48. Liu X, Jiang S, Lai W, Yi X, Yang L, Fang W (2017) Reac Kinet Mech Cat 121:673–687

    Article  CAS  Google Scholar 

  49. Gomez S, Peters JA, Maschmeyer T (2002) Adv Synth Catal 344:1037–1057

    Article  CAS  Google Scholar 

  50. Chen H, Xue M, Hu S, Shen J (2012) Chem Eng J 181–182:677–684

    Article  Google Scholar 

  51. Johnson RS, DeLaRiva A, Ashbacher V, Halevi B, Villanueva CJ, Smith GK, Lin S, Datye AK, Guo H (2013) Phys Chem Chem Phys 15:7768–7776

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Nos. 21703179 and 21473143) and the Fundamental Research Funds for the Central Universities of China (No. 20720170103).

Author information

Authors and Affiliations

  1. National Engineering Laboratory for Green Chemical Productions of Alcohols-Ethers-Esters, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, People’s Republic of China

    Weikun Lai, Yingxu Tian, Kang Yang, Yixin Lian & Weiping Fang

  2. School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan, 430073, People’s Republic of China

    Wenjing Song

Authors
  1. Weikun Lai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yingxu Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wenjing Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kang Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yixin Lian
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Weiping Fang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yixin Lian.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 290 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lai, W., Tian, Y., Song, W. et al. Direct synthesis of 3-picoline from 2-methylglutaronitrile over supported PdZn catalyst: promoting effects of Zn. Reac Kinet Mech Cat 125, 951–964 (2018). https://doi.org/10.1007/s11144-018-1437-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-018-1437-6

Keywords

Search

Navigation