Skip to main content

Advertisement

SpringerLink
Log in

Preparation and characterization of melamine-based porous Schiff base polymer networks for hydrogen storage

  • Original Paper
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Based on Schiff base chemistry, crosslinked porous organic aminal networks were prepared using acetic acid as a catalyst. These Schiff base networks (SNWs) are polymeric materials based on melamine and 5,5′-methylene-bis-salicylaldehyde, with nitrogen contents as high as ca. 36 wt.%, which were characterized by FTIR spectroscopy, elemental analysis, and 13C and 15 N solid-state NMR spectroscopies. A series of polymer networks with different monomeric molar ratios and different amounts of added catalyst were explored, in order to study their effect on the final polymer structure, porosity and H2 storage capacity. These materials exhibit Brunauer-Emmett-Teller (BET) surface areas up to ca. 526 m2/g, as measured by N2 adsorption at 77 K, and exhibit gravimetric storage capacities up to 2.57 wt.% at 20 bar and 77 K.

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

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

Similar content being viewed by others

References

  1. Schlapbach L, Züttel A (2001) Nature 414:353–358

    Article  CAS  Google Scholar 

  2. Yang J, Sudik A, Wolverton C, Siegel DJ (2010) Chem Soc Rev 39:656–675

    Article  CAS  Google Scholar 

  3. US Department of Energy, Office of Energy Efficiency and Renewable Energy, and The FreedomCAR and Fuel Partnership, (2009) Targets for Onboard Hydrogen Storage Systems for Light-Duty Vehicles, http://www1.eere.energy.gov/hydrogenandfuelcells/storage/pdfs/targets_onboard_hydro_storage_explanation.pdf

  4. US Department of Energy, Stetson N (2013) Hydrogen Storage Program Overview, http://www.hydrogen.energy.gov/pdfs/progress13/iv_0_stetson_2013.pdf

  5. Regli L, Zecchina A, Vitillo JG, Cocina D, Spoto G, Lamberti C, Lillerud KP, Olsbye U, Bordiga S (2005) Phys Chem Chem Phys 7:3197–3203

    Article  CAS  Google Scholar 

  6. Weitkamp J, Fritz M, Ernst S (1995) Int J Hydrogen Energy 20:967–970

    Article  CAS  Google Scholar 

  7. Zhao XB, Xiao B, Fletcher AJ, Thomas KM (2005) J Phys Chem B 109:8880–8888

    Article  CAS  Google Scholar 

  8. Panella B, Hirscher M, Roth S (2005) Carbon 43:2209–2214

    Article  CAS  Google Scholar 

  9. Meng S, Kaxiras E, Zhang Z (2007) Nano Lett 7:663–667

    Article  CAS  Google Scholar 

  10. Züttel A, Sudan P, Mauron P, Kiyobayashi T, Emmenegger C, Schlapbach L (2002) Int J Hydrogen Energy 27:203–212

    Article  Google Scholar 

  11. Han SS, Furukawa H, Yaghi OM, Goddard WA (2008) J Am Chem Soc 130:11580–11581

    Article  CAS  Google Scholar 

  12. Germain J, Fréchet JMJ, Svec F (2007) J Mater Chem 17:4989–4997

    Article  CAS  Google Scholar 

  13. Wood CD, Tan B, Trewin A, Niu H, Bradshaw D, Rosseinsky MJ, Khimyak YZ, Campbell NL, Kirk R, Stöckel E, Cooper AI (2007) Chem Mater 19:2034–2048

    Article  CAS  Google Scholar 

  14. Wood CD, Tan B, Trewin A, Su F, Rosseinsky MJ, Bradshaw D, Sun Y, Zhou L, Cooper AI (2008) Adv Mater 20:1916–1921

    Article  CAS  Google Scholar 

  15. Shaffei KA, Atta AM, Gomes CSB, Gomes PT, El-Ghazawy RA, Mahmoud AG (2014) J Polym Res 21:245

    Article  Google Scholar 

  16. Belyakova LD, Schevchenko TI, Davankov VA, Tsyurupa MP, Nesmeyanov AN (1986) Adv Colloid Interface Sci 25:249–266

    Article  CAS  Google Scholar 

  17. Podlesnyuk VV, Hradil J, Králová E (1999) React Funct Polym 42:181–191

    Article  CAS  Google Scholar 

  18. McKeown NB, Budd PM (2006) Chem Soc Rev 35:675–683

    Article  CAS  Google Scholar 

  19. Mackintosh HJ, Budd PM, McKeown NB (2008) J Mater Chem 18:573–578

    Article  CAS  Google Scholar 

  20. Schmidt J, Weber J, Epping JD, Antonietti M, Thomas A (2009) Adv Mater 21:702–705

    Article  CAS  Google Scholar 

  21. Germain J, Fréchet JMJ, Svec F (2009) Small 5:1098–1111

    Article  CAS  Google Scholar 

  22. El-Kaderi HM, Hunt JR, Mendoza-Cortés JL, Côté AP, Taylor RE, O’Keeffe M, Yaghi OM (2007) Science 316:268–272

    Article  CAS  Google Scholar 

  23. Campbell NL, Clowes R, Ritchie LK, Cooper AI (2009) Chem Mater 21:204–206

    Article  CAS  Google Scholar 

  24. McKeown NB, Budd PM (2010) Macromolecules 43:5163–5176

    Article  CAS  Google Scholar 

  25. Ghanem BS, Msayib KJ, McKeown NB, Harris KDM, Pan Z, Budd PM, Butler A, Selbie J, Book D, Walton A (2007) Chem Commun 67–69

  26. Tsyurupa MP, Davankov VA (2006) React Funct Polym 66:768–779

    Article  CAS  Google Scholar 

  27. Jiang J-X, Su F, Trewin A, Wood CD, Campbell NL, Niu H, Dickinson C, Ganin AY, Rosseinsky MJ, Khimyak YZ, Cooper AI (2007) Angew Chem Int Ed 46:8574–8578

    Article  CAS  Google Scholar 

  28. Ahn J-H, Jang J-E, Oh C-G, Ihm S-K, Cortez J, Sherrington DC (2006) Macromolecules 39:627–632

    Article  CAS  Google Scholar 

  29. Hulicova D, Yamashita J, Soneda Y, Hatori H, Kodama M (2005) Chem Mater 17:1241–1247

    Article  CAS  Google Scholar 

  30. Yang SJ, Cho JH, Oh GH, Nahm KS, Park CR (2009) Carbon 47:1585–1591

    Article  CAS  Google Scholar 

  31. Schwab MG, Fassbender B, Spiess HW, Thomas A, Feng X, Müllen K (2009) J Am Chem Soc 131:7216–7217

    Article  CAS  Google Scholar 

  32. Layer RW (1963) Chem Rev 63:489–510

    Article  CAS  Google Scholar 

  33. Uribe-Romo FJ, Hunt JR, Furukawa H, Klöck C, O’Keeffe M, Yaghi OM (2009) J Am Chem Soc 131:4570–4571

    Article  CAS  Google Scholar 

  34. Pandey P, Katsoulidis AP, Eryazici I, Wu Y, Kanatzidis MG, Nguyen ST (2010) Chem Mater 22:4974–4979

    Article  CAS  Google Scholar 

  35. Ding S-Y, Gao J, Wang Q, Zhang Y, Song W-G, Su C-Y, Wang W (2011) J Am Chem Soc 133:19816–19822

    Article  CAS  Google Scholar 

  36. Wan S, Gándara F, Asano A, Furukawa H, Saeki A, Dey SK, Liao L, Ambrogio MW, Botros YY, Duan X, Seki S, Stoddart JF, Yaghi OM (2011) Chem Mater 23:4094–4097

    Article  CAS  Google Scholar 

  37. Uribe-Romo FJ, Doonan CJ, Furukawa H, Oisaki K, Yaghi OM (2011) J Am Chem Soc 133:11478–11481

    Article  CAS  Google Scholar 

  38. Yang G, Han H, Du C, Luo Z, Wang Y (2010) Polymer 51:6193–6202

    Article  CAS  Google Scholar 

  39. Li G, Zhang B, Yan J, Wang Z (2014) Chem Commun 50:1897–1899

    Article  CAS  Google Scholar 

  40. Armarego WLF, Chai CLL (2009) Purification of Laboratory Chemicals. Elsevier Inc, Burlington

    Google Scholar 

  41. Marvel CS, Tarköy N (1957) J Am Chem Soc 79:6000–6002

    Article  CAS  Google Scholar 

  42. Bell RP, Bascombe KN, Coutrey JCM (1956) J Chem Soc 1286–1291

  43. Mésangeau C, Yous S, Pérès B, Lesieur D, Besson T (2005) Tetrahedron Lett 46:2465–2468

    Article  Google Scholar 

  44. Kailasam K, Jun Y-S, Katekomol P, Epping JD, Hong WH, Thomas A (2010) Chem Mater 22:428–434

    Article  CAS  Google Scholar 

  45. Coullerez G, Léonard D, Lundmark S, Mathieu HJ (2000) Surf Interface Anal 29:431–443

    Article  CAS  Google Scholar 

  46. Meier RJ, Tiller A, Vanhommerig SAM (1995) J Phys Chem 99:5457–5464

    Article  CAS  Google Scholar 

  47. Larkin P (2011) Infrared and Raman Spectroscopy. Elsevier Inc, Waltham

    Google Scholar 

  48. Kaya I, Yildirim M (2009) Synth Met 159:1572–1582

    Article  CAS  Google Scholar 

  49. Baraka A, Hall PJ, Heslop MJ (2007) React Funct Polym 67:585–600

    Article  CAS  Google Scholar 

  50. Egger CC, Schädler V, Hirschinger J, Raya J, Bechinger B (2007) Macromol Chem Phys 208:2204–2214

    Article  CAS  Google Scholar 

  51. Subrayan RP, Jone FN (1996) J Appl Polym Sci 62:1237–1251

    Article  CAS  Google Scholar 

  52. Hindson JC, Ulgut B, Friend RH, Greenham NC, Norder B, Kotlewski A, Dingemans TJ (2010) J Mater Chem 20:937–944

    Article  CAS  Google Scholar 

  53. Budd PM, Ghanem BS, Makhseed S, McKeown NB, Msayib KJ, Tattershall CE (2004) Chem Commun 230–231

  54. McKeown NB, Gahnem B, Msayib KJ, Budd PM, Tattershall CE, Mahmood K, Tan S, Book D, Langmi HW, Walton A (2006) Angew Chem Int Ed 45:1804–1807

    Article  CAS  Google Scholar 

  55. Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquerol J, Siemieniewska T (1985) Pure Appl Chem 57:603–619

  56. Hirscher M, Panella B (2007) Scr Mater 56:809–812

    Article  CAS  Google Scholar 

  57. Gadiou R, Saadallah S-E, Piquero T, David P, Parmentier J, Vix-Guterl C (2005) Microporous Mesoporous Mater 79:121–128

    Article  CAS  Google Scholar 

  58. Panella B, Hirscher M, Pütter H, Müller U (2006) Adv Funct Mater 16:520–524

    Article  CAS  Google Scholar 

  59. Wong-Foy AG, Matzger AJ, Yaghi OM (2006) J Am Chem Soc 128:3494–3495

    Article  CAS  Google Scholar 

  60. Thomas KM (2007) Catal Today 120:389–398

    Article  CAS  Google Scholar 

  61. Nijkamp MG, Raaymakers JEMJ, van Dillen AJ, de Jong KP (2001) Appl Phys A 72:619–623

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the Fundação para a Ciência e Tecnologia, Portugal, for financial support (Projects PTDC/EQU-EQU/110313/2009, PEst-OE/QUI/UI0100/2013 and RECI/QEQ-QIN70189/2012) and for a fellowship to C.S.B.G. (SFRH/BPD/64423/2009). We thank the Erasmus Mundus programme (WELCOME) for granting a scholarship to A.G.M. Thanks are also due to Dr. Teresa Nunes for helpful discussions about the solid state NMR measurements.

Author information

Authors and Affiliations

  1. Centro de Química Estrutural, Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001, Lisboa, Portugal

    Abdallah G. Mahmoud, M. João Ferreira, Clara S. B. Gomes & Pedro T. Gomes

  2. Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan, Cairo, Egypt

    Abdallah G. Mahmoud & K. A. Shaffei

  3. Egyptian Petroleum Research Institute, 1 Ahmad Elzomor St., Nasr City, 11727, Cairo, Egypt

    Rasha A. El-Ghazawy & Ayman M. Atta

  4. Surfactant Research Chair, Chemistry Department, College of Science, King Saud University, P.O. Box 2455, 11451, Riyadh, Saudi Arabia

    Ayman M. Atta

Authors
  1. Rasha A. El-Ghazawy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Abdallah G. Mahmoud
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. João Ferreira
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Clara S. B. Gomes
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pedro T. Gomes
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. A. Shaffei
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ayman M. Atta
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Pedro T. Gomes or Ayman M. Atta.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 29.1 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

El-Ghazawy, R.A., Mahmoud, A.G., Ferreira, M.J. et al. Preparation and characterization of melamine-based porous Schiff base polymer networks for hydrogen storage. J Polym Res 21, 480 (2014). https://doi.org/10.1007/s10965-014-0480-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-014-0480-x

Keywords

Search

Navigation