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Catalysis Letters

, Volume 148, Issue 8, pp 2373–2381 | Cite as

Highly Basic and Dipolar Layered Double Hydroxides Enhance Catalysis of Cyanoethylation of Alcohols

  • Mariana Díaz
  • Alejandra Santana Cruz
  • Jorge Flores
  • Ariel Guzmán
  • Enrique Lima
Article

Abstract

Layered double hydroxides (LDH), magnesium–aluminum–carbonates and magnesium–gallium–aluminum–carbonates, were synthesized by sol–gel incorporating during synthesis a part of aluminum as (AlF6)3− blocks in order to incorporate F as a part of brucite-like layers and not as compensating anions. Structural, textural and surface properties of resulting fluorinated were characterized. Particularly, presence the fluorine as a part of brucite-like layers influenced directly polarity and hydrogen bonding acceptor character at surface of materials. These modifications at surface of LDH greatly changed their catalytic properties. Cyanoethylation reaction between acrylonitrile and methanol was catalyzed by both fluorine-free and fluorinated LDH, pointing out a clear influence of fluorine on the conversion and rate reaction.

Graphical Abstract

Keywords

Layered double hydroxides Catalysts Basicity Polarity Cyanoethylation 

Notes

Acknowledgements

This work was financially supported by CONACYT (Grant 220436) and PAPIIT-IN106517. We are also grateful to G. Cedillo and A. Tejeda for their technical assistance.

References

  1. 1.
    Bruson HA (1949) Organic reactions V. In: Adams R (ed) Organic reactions V. Wiley, New York, pp 79–135Google Scholar
  2. 2.
    MacGregor JH, Pugh C (1945) J Chem Soc 535Google Scholar
  3. 3.
    Utermohlen WP (1945) J Am Chem Soc 67:1505CrossRefGoogle Scholar
  4. 4.
    Astle MJ, Etherington RW (1952) Ind Eng Chem 44:2871CrossRefGoogle Scholar
  5. 5.
    Trinadh M, Rajasekhar T, Bhadru B, Gopinath J, Santosh V, Reddy BVS, Sainath AVS (2013) J Appl Polym Sci 128:795CrossRefGoogle Scholar
  6. 6.
    Kabashima H, Hattori H (1998) Catal Today 44:277CrossRefGoogle Scholar
  7. 7.
    Zamanian S, Kharat AN (2014) Chin J Catal 35:264CrossRefGoogle Scholar
  8. 8.
    Kumbhar PS, Sanchez-Valente J, Figueras F (1998) Chem Commun 10:1091CrossRefGoogle Scholar
  9. 9.
    Valente J, Pfeiffer H, Lima E, Prince J, Flores J (2011) J Catal 279:196CrossRefGoogle Scholar
  10. 10.
    Angelescu E, Pavel OD, Che M, Bîrjega R, Constentin G (2004) Catal Commun 10:647CrossRefGoogle Scholar
  11. 11.
    Bîrjega R, Pavel OD, Costentin G, Che M, Angelescu E (2005) Appl Catal A 288:185CrossRefGoogle Scholar
  12. 12.
    Miyata S (1975) Clays Clay Miner 23:369CrossRefGoogle Scholar
  13. 13.
    Miyata S (1983) Clays Clay Miner 31:305CrossRefGoogle Scholar
  14. 14.
    Ulibarri MA, Hernandez MJ, Cornejo J (1991) J Mater Sci 26:1512CrossRefGoogle Scholar
  15. 15.
    Braterman PS, Ping Xu Z, Yarberry F (2004) Layered double hydroxides. In: Auerbach SM, Carrado KA, Dutta PK (eds) Handbook of layered materials. CRC Press, New York, pp 373–474Google Scholar
  16. 16.
    Choudary BM, Kantam ML, Kavita B, Reddy CV, Rao K, Figueras F (1998) Tetrahedron Lett 39:3555CrossRefGoogle Scholar
  17. 17.
    Hora L, Kelbichová V, Kikhtyanin O, Bortnovskiy O, Kubička D (2014) Catal Today 138Google Scholar
  18. 18.
    Monzón A, Romeo E, Royo C, Trujillano R, Labajos FM, Rives V (1999) Appl Catal A 185:53CrossRefGoogle Scholar
  19. 19.
    Coq B, Tichit D, Ribet S (2000) J Catal 189:117CrossRefGoogle Scholar
  20. 20.
    Barrault J, Derouault A, Courtois G, Maissant JM, Dupin JC, Guimon C, Martinez H, Dumitriu E (2004) Appl Catal A 262:43CrossRefGoogle Scholar
  21. 21.
    Liu Y, Lotero E, Goodwin JG Jr, Mo X (2007) Appl Catal A 138Google Scholar
  22. 22.
    Li E, Zhi PX, Rudolph V. Appl Catal B (2009) 88:42CrossRefGoogle Scholar
  23. 23.
    Turco M, Bagnasco G, Costantino U, Marmottini F, Montanari T, Ramis G, Busca G (2004) J Catal 228:43Google Scholar
  24. 24.
    Cavani F, Trifirò F, Vaccari A (1991) Catal Today 11:173CrossRefGoogle Scholar
  25. 25.
    Prinetto F, Ghiotti G, Robert D, Tichit D (2000) J Phys Chem B 104:11117CrossRefGoogle Scholar
  26. 26.
    Lakshmi Kantam MB, Choudary M, Reddy CV, Koteswara Rao K, Lakshmi Kantam M, Choudary BM, Koteswara Rao K, Figueras F (1998) Chem Commun 32:1033CrossRefGoogle Scholar
  27. 27.
    Roelofs JCAA., Lensveld DJ, Van Dillen AJ, De Jong KP (2001) J Catal 203:184CrossRefGoogle Scholar
  28. 28.
    Climent MJ, Corma A, Iborra S, Velty A (2004) J Catal 221:474CrossRefGoogle Scholar
  29. 29.
    Constantino VRL, Pinnavaia TJ (1995) Inorg Chem 34:883CrossRefGoogle Scholar
  30. 30.
    Prescott HA, Li ZJ, Kemnitz E, Trunschke A, Deutsch J, Lieske H, Auroux A (2005) J Catal 234:119CrossRefGoogle Scholar
  31. 31.
    Lima E, Martínez-Ortiz MJ, Gutiérrez Reyes RI, Vera M (2012) Inorg Chem 51:7774CrossRefPubMedGoogle Scholar
  32. 32.
    Lima E, Pfeiffer H, Flores J (2014) Appl Clay Sci 88–89:26Google Scholar
  33. 33.
    Valente JS, Cantú M, Cortez JGH, Montiel R, Bokhimi X, López-Salinas E (2007) J Phys Chem C 111:642CrossRefGoogle Scholar
  34. 34.
    López-Salinas E, Garcia-Sánchez M, Ramón-Garcia ML, Schifter I (1996) J Porous Mater 3:169CrossRefGoogle Scholar
  35. 35.
    Lungwitz R, Spange S (2008) New J Chem 32:392CrossRefGoogle Scholar
  36. 36.
    Spange S, Prause S, Vilsmeier E, Thiel WR (2005) J Phys Chem B 109:7280CrossRefPubMedGoogle Scholar
  37. 37.
    Spange S, Zimmermann Y, Graeser A (1999) Chem Mater 11:3245CrossRefGoogle Scholar
  38. 38.
    Spange S, Schmidt C, Kricheldorf HR (2001) Langmuir 17:856CrossRefGoogle Scholar
  39. 39.
    Lippmaa E, Samoson A, Mägi M (1986) J Am Chem Soc 108:1730CrossRefGoogle Scholar
  40. 40.
    Scholz G, Stosiek C, Noack J, Kemnitz E (2011) J Fluorine Chem 132:1079CrossRefGoogle Scholar
  41. 41.
    Krahl T, Ahrens M, Scholz G, Heidemann D, Kemnitz E (2008) Inorg Chem 47:663CrossRefPubMedGoogle Scholar
  42. 42.
    Zhang W, Wang D. Ma J, Wei W (2017) Catal Lett 147:1181CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Mariana Díaz
    • 1
  • Alejandra Santana Cruz
    • 2
  • Jorge Flores
    • 2
  • Ariel Guzmán
    • 3
  • Enrique Lima
    • 1
    • 2
  1. 1.Laboratorio de Fisicoquímica y Reactividad de Superficies (LaFReS), Instituto de Investigaciones en MaterialesUniversidad Nacional Autónoma de MéxicoMexico CityMexico
  2. 2.Universidad Autónoma Metropolitana, AzcapotzalcoMexico CityMexico
  3. 3.Instituto Politécnico Nacional - ESIQIEMexico CityMexico

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