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N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst

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Abstract

The mesoporous solid acid–base Cs–B–Zr mixed oxides were synthesized using the co-precipitation method followed by a subsequent thermal treatment. The catalytic activity of solid Cs–B–Zr mixed oxide was tested for solvent free acid–base catalysed direct alkylolamines with alcohols as green alkylating agent. The effects of Cs/B/Zr ratio, calcination temperature, reaction conditions, and reaction substrate on the catalytic performance of the catalysts were investigated. The XRD, N2 adsorption–desorption, ICP-OES, FT-IR and NH3/CO2-TPD results showed that the mesoporous structure and acid–base properties of the catalysts play important roles in the reaction. A suitable number of acid and basic sites on the catalyst lead to a high activity for the N-alkylation reaction.

Graphical Abstract

A direct N-alkylation of amino alcohol with alcohols has been developed using mixed oxide Cs–B–Zr as an acid–base bifunctionalized catalyst.

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References

  1. Lawrence S (2004) Amines: synthesis, properties and application. Cambridge University Press, Cambridge

    Google Scholar 

  2. Seayad A, Ahmed M, Klein H, Jackstell R, Gross T, Beller M (2002) Science 297:1676

    Article  CAS  Google Scholar 

  3. Brown B (1994) The organic chemistry of aliphatic nitrogen compounds. Oxford University Press, New York, pp 350–352

    Google Scholar 

  4. Yin H, Jin M, Chen W, Chen C, Zheng L, Wei P, Han S (2012) Tetrahedron Lett 53:1265

    Article  CAS  Google Scholar 

  5. Lombardo M, Mosconi E, Pasi F, Petrini M, Trombini C (2007) J Org Chem 72:1834

    Article  CAS  Google Scholar 

  6. Nakano H, Yokoyama J, Fujita R, Hongo H (2002) Tetrahedron Lett 43:7761

    Article  CAS  Google Scholar 

  7. Kashima C, Harada K, Omote Y (1985) Can J Chem 63:288

    Article  CAS  Google Scholar 

  8. Chakraborti A, Kondaskar A (2003) Tetrahedron Lett 44:8315

    Article  CAS  Google Scholar 

  9. Pujala B, Rana S, Chakraborti A (2011) J Org Chem 76:8768

    Article  CAS  Google Scholar 

  10. He W, Wang L, Sun C, Wu K, He S, Chen J, Wu P, Yu Z (2011) Chem Eur J 17:13308

    Article  CAS  Google Scholar 

  11. Cui X, Dai X, Deng Y, Shi F (2013) Chem Eur J 19:3665

    Article  CAS  Google Scholar 

  12. Jumde V, Gonsalvi L, Guerriero A, Peruzzini M, Taddei M (2015) Eur J Org Chem 2015:1829–1833

    Article  CAS  Google Scholar 

  13. Edwards M, Jazzar F, Paine B, Shermer D, Whittlesey M, Williams M, Edney D (2004) Chem Commun Camb 1:90

    Article  Google Scholar 

  14. Grigg R, Mitchell T, Sutthivaiyakit S, Tongpenyai N (1981) J Chem Soc Chem Commun 12:611

    Article  Google Scholar 

  15. Watanabe Y, Tsuji Y, Ohsugi Y (1981) Tetrahedron Lett 22:2667

    Article  CAS  Google Scholar 

  16. Hamid M, Allen C, Lamb G, Maxwell A, Maytum H, Watson A, Williams J (2009) J Am Chem Soc 131:1766

    Article  CAS  Google Scholar 

  17. Dang T, Ramalingam B, Shan SP, Seayad A (2013) ACS Catal 3:2536

    Article  CAS  Google Scholar 

  18. Ohshima T, Miyamoto Y, Ipposhi J, Nakahara Y, Utsunomiya M, Mashima K (2009) J Am Chem Soc 131:14317

    Article  CAS  Google Scholar 

  19. Yang H, Mao R, Luo C, Lu C, Cheng G (2014) Tetrahedron 70:8829

    Article  CAS  Google Scholar 

  20. Gunanathan C, Milstein D (2008) Angew Chem Int Ed 47:8661

    Article  CAS  Google Scholar 

  21. Gnanamgari D, Sauer E, Schley N, Butler C, Incarvito C, Crabtree R (2009) Organometallics 28:321

    Article  CAS  Google Scholar 

  22. Kawahara R, Fujita K, Yamaguchi R (2010) J Am Chem Soc 132:15108

    Article  CAS  Google Scholar 

  23. Reddy M, Kumar M, Swamy P, Naresh M, Srujana K, Satyanarayana L, Venugopala A, Narender N (2013) Green Chem 15:3474

    Article  CAS  Google Scholar 

  24. Tayade K, Mishra M, Munusamy K, Somani R (2014) J Mol Catal A Chem 390:91

    Article  CAS  Google Scholar 

  25. Sun Y, Lu X, Wei X, Zhou D, Xia Q (2014) Catal Commun 43:213

    Article  CAS  Google Scholar 

  26. Pathare S, Akamanchi K (2013) Appl Catal A Gen 452:29

    Article  CAS  Google Scholar 

  27. Lee YY, Kevin WCW (2012) Phys Chem Chem Phys 14:13914

    Article  CAS  Google Scholar 

  28. Peng WH, Lee YY, Connie W, Kevin WCW (2012) J Mater Chem 22:23181

    Article  CAS  Google Scholar 

  29. Ivanova I, Knyazeva EE (2013) Chem Soc Rev 42:3671

    Article  CAS  Google Scholar 

  30. Oku T, Arita Y, Tsuneki H, Ikariya T (2004) J Am Chem Soc 126:7368

    Article  CAS  Google Scholar 

  31. Qiu C, Lin T, Zhang Q, Xu HD, Chen Y, Gong M (2011) Chin J Catal 32:1227

    CAS  Google Scholar 

  32. Malshe K, Patil P, Umbarkar S, Dongare M (2004) J Mol Catal A Chem 212:337

    Article  CAS  Google Scholar 

  33. Kong X, Wang G, Du X, Lu L, Li L, Chen L (2012) Catal Commun 27:26–29

    Article  CAS  Google Scholar 

  34. Liang Q, Hu Q, Miao G, Yuan B, Chen X (2015) Mater Lett 148:45

    Article  CAS  Google Scholar 

  35. Dayananda D, Sarva V, Prasad S, Arunachalam J, Parameswaran P, Ghosh N (2015) Appl Surf Sci 329:1

    Article  CAS  Google Scholar 

  36. Panda A, Sinhamahapatra A, Sutradhar N et al (2011) Appl Catal A Gen 402:87

    Article  Google Scholar 

  37. Panda A, Sinhamahapatra A, Pal P et al (2013) Chem Cat Chem 5:331

    Google Scholar 

  38. Egili K, Oraby A (1996) J Phys Condens Matter 8:8959

    Article  Google Scholar 

  39. Motke S, Yawale S, Yawale S (2002) Bull Mater Sci 25:75

    Article  CAS  Google Scholar 

  40. Xu B, Cheng S (1999) S J, Zhu Q. Appl Catal A Gen 188:361–368

    Article  CAS  Google Scholar 

  41. Srivastava A, Dongare M (1987) Mater Lett 5:111

    Article  CAS  Google Scholar 

  42. Shen W, Tang X, Yong Li et al (2006) Appl Catal B Environ 62:265

    Article  Google Scholar 

  43. Xu S, Hong Y, Chen C, Li S, Xiao L, Fan J (2013) J Mater Chem A 1:6191

    Article  CAS  Google Scholar 

  44. Dongare M, Madje B, Patil P et al (2004) Catal Commun 5:353

    Article  Google Scholar 

  45. Xu Q, Li Q, Zhu X, Chen J (2013) Adv Synth Catal 355:73

    Article  CAS  Google Scholar 

  46. Lu X, Sun Y, Wei X, Peng C, Zhou D, Xia Q (2014) Catal Commun 55:78

    Article  CAS  Google Scholar 

  47. Bahn S, Imm S, Neubert L, Zhang M, Neumann H, Beller M (2011) ChemCatChem 3:1853–1864

    Article  Google Scholar 

  48. Tsuneki H (2001) Appl Catal A Gen 221:209

    Article  CAS  Google Scholar 

  49. Wang W, Seiler M, Ivanova I, Sternberg U, Weitkamp J, Hunger M (2002) J Am Chem Soc 124:7548

    Article  CAS  Google Scholar 

  50. Wang W, Buchholz A, Seiler M, Hunger M (2003) J Am Chem Soc 125:15260

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful for the National Natural Science Foundation of China (Nos. 51002137, 10804099) and the Zhejiang Basic Research Development Program (LQ12E02009).

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Authors and Affiliations

  1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China

    Aimin Chen, Houyong Wang, Rui Liu, Yingying Bo & Jun Hu

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  1. Aimin Chen
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  2. Houyong Wang
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  3. Rui Liu
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  4. Yingying Bo
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  5. Jun Hu
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Correspondence to Aimin Chen or Jun Hu.

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Chen, A., Wang, H., Liu, R. et al. N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst. Catal Lett 146, 1182–1193 (2016). https://doi.org/10.1007/s10562-016-1737-2

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  • DOI: https://doi.org/10.1007/s10562-016-1737-2

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