Modified fluorapatite as highly efficient catalyst for the synthesis of chalcones via Claisen-Schmidt condensation reaction

Ilham Jioui; Karim Danoun; Abderrahim Solhy; Mustapha Jouiad; Mohamed Zahouily; Bilal Essaid; Christophe Len; Aziz Fihri

Journal of Industrial and Engineering Chemistry, Vol.39, 218-225, July, 2016

DOI10.1016/j.jiec.2016.06.003 Export Citation

Modified fluorapatite as highly efficient catalyst for the synthesis of chalcones via Claisen-Schmidt condensation reaction

Ilham Jioui¹, Karim Danoun^{1, 2}, Abderrahim Solhy^{3, †}, Mustapha Jouiad^{4, †}, Mohamed Zahouily^{1, 2}, Bilal Essaid⁵, Christophe Len⁶, and Aziz Fihri^{2, †}

¹Laboratoire de Materiaux, Catalyse & Valorisation des Ressources Naturelles, URAC 24, Faculte des Sciences et Techniques, Universite Hassan II, Casablanca B.P. 146, 20650, Morocco
²MAScIR Foundation, VARENA Center, Rabat Design, Rue Mohamed El Jazouli, Madinat Al Irfane, 10100 Rabat, Morocco
³Center for Advanced Materials (CAM), Mohammed VI Polytechnic University, Lot 660-Hay Moulay Rachid, 43150 Ben Guerir, Morocco
⁴Department of Mechanical and Materials Engineering, Masdar Institute of Science and Technology, 54224 Abu Dhabi, United Arab Emirates
⁵R&D OCP, OCP Group, Complexe industriel Jorf Lasfar, BP 118, El Jadida, Morocco
⁶Sorbonne Universites, Transformations Integrees de la Matiere Renouvelable, UTC/ESCOM, Centre de Recherche Royallieu, CS60319, F-60203 Compiegne Cedex, France

E-mail:, ,

In the present study, we investigated the synthesis of fluorapatite using a pseudo sol-gel process and the chemical modification of this new catalyst support via impregnation of sodium nitrate followed by calcination at 550 ℃ in order to enhance its catalytic performance. This approach was used to obtain a bi-functional catalyst for Claisen-Schmidt condensation. Indeed, this heterogeneous catalyst exhibited excellent catalytic activity and high selectivity for the synthesis of chalcones from direct aromatic aldehydes with substituted ketones at room temperature. The operational simplicity, excellent yields of the products and the recyclability of the catalyst are the main advantages of this method.

Keywords:Heterogeneous catalysis;Modified fluorapatite;Claisen-Schmidt condensation;Chalcones

[References]

Wattenberg LW, Coccia JB, Galbraith AR, Cancer Lett., 83, 165 (1994)
Srimal RC, Dhawan BN, J. Pharm. Pharmacol., 25, 447 (1973)
Nowakowska Z, Eur. J. Med. Chem., 42, 125 (2007)
Go ML, Wu X, Liu XL, Curr. Med. Chem., 12, 483 (2005)
Kumar D, Kumar NM, Akamatsu K, Kusaka E, Harada H, Ito T, Bioorg. Med. Chem. Lett., 20, 3916 (2011)
Sivakumar PM, Ganesan S, Veluchamy P, Doble M, Chem. Biol. Drug. Des., 76, 407 (2010)
Drexler MT, Amiridis MD, J. Catal., 214(1), 136 (2003)
Park SN, Kim SY, Lim GN, Jo NR, Lee MH, J. Ind. Eng. Chem., 25, 680 (2012)
Halake K, Birajdar M, Lee J, J. Ind. Eng. Chem., 25, 1 (2016)
Song D, Rostami A, West FG, J. Am. Chem. Soc., 129(39), 12019 (2007)
Nielsen SF, Christensen SB, Cruciani G, Kharazmi A, Liljefors T, J. Med. Chem., 41, 4819 (1998)
Edwards ML, Stemerick DM, Sunkara PS, J. Med. Chem., 33, 1948 (1990)
Bu XY, Zhao LY, Li YL, Synthesis, 1246 (1997)
Bu XY, Li YL, J. Nat. Prod., 59, 968 (1996)
Sathyanarayana S, Krishnamurthy HG, Curr. Sci., 57, 1114 (1988)
Alcantara AR, Marinas JM, Sinisterra JV, Tetrahedron Lett., 28, 1515 (1987)
Sinisterra JV, Garcia-Raso A, Cabello JA, Marinas JM, Synthesis, 502 (1984)
Hargrove-Leak SC, Amiridis MD, Catal. Commun., 3, 557 (2002)
Climent MJ, Corma A, Iborra S, Primo J, J. Catal., 151(1), 60 (1995)
Climent MJ, Corma A, Iborra S, Velty A, J. Catal., 221(2), 474 (2004)
Solhy A, Tahir R, Sebti S, Skouta R, Bousmina M, Zahouily M, Larzek M, Appl. Catal. A: Gen., 374(1-2), 189 (2010)
Mazumder NA, Rano R, J. Ind. Eng. Chem., 29, 359 (2015)
Sebti S, Solhy A, Tahir R, Boulaajaj S, Mayoral JA, Fraile JM, Kossir A, Oumimoun H, Tetrahedron Lett., 42, 7953 (2001)
Macquarrie DJ, Nazih R, Sebti S, Green Chem., 4, 56 (2002)
Yamagishi K, Onuma K, Suzuki T, Okada F, Tagami J, Otsuki M, Senawangse P, Nature, 453, 819 (2005)
Wang L, He S, Wu X, Liang S, Mu Z, Wei J, Deng F, Deng Y, We S, Biomaterials, 35, 6758 (2014)
Khattech I, Jemal M, Thermochim. Acta, 298(1-2), 23 (1997)
Wei M, Evans JH, Bostrom T, Grondahl L, J. Mater. Sci. -Mater. Med., 14, 311 (2003)
Plana F, Font-Altaba M, Traveria-Cros A, Cuevas-Diarte MA, Acta Geol. Hisp., 15, 15 (1980)
Escudero A, Calvo ME, Rivera-Fernandez S, de la Fuente JM, Ocana M, Langmuir, 29(6), 1985 (2013)
Kantam ML, Kumar KBS, Srinivas P, Sreedhar B, Adv. Synth. Catal., 349, 1141 (2007)
Mori K, Yamaguchi K, Hara T, Mizugaki T, Ebitani K, Kaneda K, J. Am. Chem. Soc., 124(39), 11572 (2002)
Tahir R, Banert K, Sebti S, Appl. Catal. A: Gen., 315, 147 (2006)
Zahouily M, Abrouki Y, Rayadh A, Sebti S, Dhimanec H, David M, Tetrahedron Lett., 44, 2463 (2003)
Saber A, Smahi A, Solhy A, Nazih R, Elaabar B, Maizi M, Sebti S, J. Mol. Catal. A-Chem., 202(1-2), 229 (2003)
Solhy A, Smahi A, Badaoui HE, Elaabar B, Amoukal A, Tikad A, Sebti S, Macquarrie DJ, Tetrahedron Lett., 44, 4031 (2003)
White TJ, Dong ZL, Acta Crystallogr. Sect. B-Struct. Sci., 59, 1 (2003)
Hopkins RH, Damon DH, Piotrowski P, Walker MS, Uphoff JH, J. Appl. Phys., 42, 272 (1971)
Elliott JC, Structure and Chemistry of the Apatites and Other Calcium Orthophosphates, Elsevier, Amsterdam, 1994.
Somasundaran P, Encyclopedia of Surface and Colloid Science, 2004 Update Supplement, Marcel Dekker, 2004.
Suith PR, LaCout JL, Hewat A, Young RA, Acta Crystallogr. Sect. B-Struct. Sci., 41, 173 (1985)
Okazaki M, Miake Y, Tohda H, Yanagisawa T, Takahasi J, Biomaterials, 20, 1303 (1999)
O’Donnell MD, Hill RG, Law RV, J. European Ceram. Soc., 29, 377 (2009)
Braun M, Hartmann P, Jana C, J. Mater. Sci. -Mater. Med., 6, 150 (1995)
Braun M, Jana C, Chem. Phys. Lett., 245, 19 (1995)

[1] Wattenberg LW, Coccia JB, Galbraith AR, Cancer Lett., 83, 165 (1994)

[2] Srimal RC, Dhawan BN, J. Pharm. Pharmacol., 25, 447 (1973)

[3] Nowakowska Z, Eur. J. Med. Chem., 42, 125 (2007)

[4] Go ML, Wu X, Liu XL, Curr. Med. Chem., 12, 483 (2005)

[5] Kumar D, Kumar NM, Akamatsu K, Kusaka E, Harada H, Ito T, Bioorg. Med. Chem. Lett., 20, 3916 (2011)

[6] Sivakumar PM, Ganesan S, Veluchamy P, Doble M, Chem. Biol. Drug. Des., 76, 407 (2010)

[7] Drexler MT, Amiridis MD, J. Catal., 214(1), 136 (2003)

[8] Park SN, Kim SY, Lim GN, Jo NR, Lee MH, J. Ind. Eng. Chem., 25, 680 (2012)

[9] Halake K, Birajdar M, Lee J, J. Ind. Eng. Chem., 25, 1 (2016)

[10] Song D, Rostami A, West FG, J. Am. Chem. Soc., 129(39), 12019 (2007)

[11] Nielsen SF, Christensen SB, Cruciani G, Kharazmi A, Liljefors T, J. Med. Chem., 41, 4819 (1998)

[12] Edwards ML, Stemerick DM, Sunkara PS, J. Med. Chem., 33, 1948 (1990)

[13] Bu XY, Zhao LY, Li YL, Synthesis, 1246 (1997)

[14] Bu XY, Li YL, J. Nat. Prod., 59, 968 (1996)

[15] Sathyanarayana S, Krishnamurthy HG, Curr. Sci., 57, 1114 (1988)

[16] Alcantara AR, Marinas JM, Sinisterra JV, Tetrahedron Lett., 28, 1515 (1987)

[17] Sinisterra JV, Garcia-Raso A, Cabello JA, Marinas JM, Synthesis, 502 (1984)

[18] Hargrove-Leak SC, Amiridis MD, Catal. Commun., 3, 557 (2002)

[19] Climent MJ, Corma A, Iborra S, Primo J, J. Catal., 151(1), 60 (1995)

[20] Climent MJ, Corma A, Iborra S, Velty A, J. Catal., 221(2), 474 (2004)

[21] Solhy A, Tahir R, Sebti S, Skouta R, Bousmina M, Zahouily M, Larzek M, Appl. Catal. A: Gen., 374(1-2), 189 (2010)

[22] Mazumder NA, Rano R, J. Ind. Eng. Chem., 29, 359 (2015)

[23] Sebti S, Solhy A, Tahir R, Boulaajaj S, Mayoral JA, Fraile JM, Kossir A, Oumimoun H, Tetrahedron Lett., 42, 7953 (2001)

[24] Macquarrie DJ, Nazih R, Sebti S, Green Chem., 4, 56 (2002)

[25] Yamagishi K, Onuma K, Suzuki T, Okada F, Tagami J, Otsuki M, Senawangse P, Nature, 453, 819 (2005)

[26] Wang L, He S, Wu X, Liang S, Mu Z, Wei J, Deng F, Deng Y, We S, Biomaterials, 35, 6758 (2014)

[27] Khattech I, Jemal M, Thermochim. Acta, 298(1-2), 23 (1997)

[28] Wei M, Evans JH, Bostrom T, Grondahl L, J. Mater. Sci. -Mater. Med., 14, 311 (2003)

[29] Plana F, Font-Altaba M, Traveria-Cros A, Cuevas-Diarte MA, Acta Geol. Hisp., 15, 15 (1980)

[30] Escudero A, Calvo ME, Rivera-Fernandez S, de la Fuente JM, Ocana M, Langmuir, 29(6), 1985 (2013)

[31] Kantam ML, Kumar KBS, Srinivas P, Sreedhar B, Adv. Synth. Catal., 349, 1141 (2007)

[32] Mori K, Yamaguchi K, Hara T, Mizugaki T, Ebitani K, Kaneda K, J. Am. Chem. Soc., 124(39), 11572 (2002)

[33] Tahir R, Banert K, Sebti S, Appl. Catal. A: Gen., 315, 147 (2006)

[34] Zahouily M, Abrouki Y, Rayadh A, Sebti S, Dhimanec H, David M, Tetrahedron Lett., 44, 2463 (2003)

[35] Saber A, Smahi A, Solhy A, Nazih R, Elaabar B, Maizi M, Sebti S, J. Mol. Catal. A-Chem., 202(1-2), 229 (2003)

[36] Solhy A, Smahi A, Badaoui HE, Elaabar B, Amoukal A, Tikad A, Sebti S, Macquarrie DJ, Tetrahedron Lett., 44, 4031 (2003)

[37] White TJ, Dong ZL, Acta Crystallogr. Sect. B-Struct. Sci., 59, 1 (2003)

[38] Hopkins RH, Damon DH, Piotrowski P, Walker MS, Uphoff JH, J. Appl. Phys., 42, 272 (1971)

[39] Elliott JC, Structure and Chemistry of the Apatites and Other Calcium Orthophosphates, Elsevier, Amsterdam, 1994.

[40] Somasundaran P, Encyclopedia of Surface and Colloid Science, 2004 Update Supplement, Marcel Dekker, 2004.

[41] Suith PR, LaCout JL, Hewat A, Young RA, Acta Crystallogr. Sect. B-Struct. Sci., 41, 173 (1985)

[42] Okazaki M, Miake Y, Tohda H, Yanagisawa T, Takahasi J, Biomaterials, 20, 1303 (1999)

[43] O’Donnell MD, Hill RG, Law RV, J. European Ceram. Soc., 29, 377 (2009)

[44] Braun M, Hartmann P, Jana C, J. Mater. Sci. -Mater. Med., 6, 150 (1995)

[45] Braun M, Jana C, Chem. Phys. Lett., 245, 19 (1995)