Document Type : Original Research Article

Authors

Department of Chemistry, Pachaiyappa’s College Chennai, Tamil Nadu, India - 600 030

Abstract

In the present study, kinetics of synthesis of spiro[cyclobutane-1,2’-indene]-1’,3’-dione was successfully carried out by spirolation of indene-1,3-dione with 1,3-dibromo propane using aqueous potassium hydroxide and catalyzed by a newly synthesized multi-site phase-transfer catalyst viz., 1,3,5-tribenzyl-1,3,5-triethyl-1,3,5-triazinane-1,3,5-triiu tribromide (MPTC), under ultrasonic (40 kHZ, 300 W) assisted organic solvent condition. The pseudo first-order under the ultrasound irradiation (40 kHz, 300 W) in a batch reactor, the overall reaction was greater than that of without ultrasound.

Graphical Abstract

Synthesis of spiro [cyclobutane-1,2'-indene]-1',3'-dione under a new multi-site phase-transfer catalyst combined with ultrasonication-a kinetic study

Keywords

Main Subjects

[1]. Yadav G.D. Top Catal., 2004, 29:145                       
[2]. Starks C.M., Liotta C.L., Halpern M. Chapman & Hall., 1994  
[3]. Dehmlow E.V., Dehmlow S.S. VCH., 1993  
[4.] Sasson Y., Neumann R., Blackie academic., 1997
[5]. Weber W.P., Gokel G.W., Springer – Verlag., 1977
[6]. Amiri K., Rostami A., Rostami A. New J.Chem.,2016, 40:7522
[7]. Yang Z., Zeng H., Zhou H., Ji H. Tetrahedron, 2012, 68:5912
[8]. Banerjee B. Ultrason. Sonochem., 2017, 35:14
[9]. Banerjee B.J. Serb. Chem. Soc., 2017, 82:755
[10]. Yang H.M., Chu W.M. Ultrason. Sonochem., 2014, 21:400
[11]. Anandan S., Asiri A.M., Ashokkumar M. Ultrason. Sonochem., 2014, 21:923
[12].Lee L.W., Yang H.M. Ind. Eng. Chem. Res., 2014, 53:12257
[13]. Abimannan P., Rajendran V. Current Catalysis, 2016, 5:44
[14].Zhao P., Wang J., Chen G., Zhou Y., Huang J. Catal. Sci. Technol., 2013, 3:1394
[15]. Mason T.J., Peters D. Ellis Horwood., 2002
[16].Luche J.L. Plenum Press., 1998 
[17]. Dubey S.M., Gogate P.R. Ind. Eng. Chem. Res., 2014, 53:7979
[18]. Selvaraj V., Rajendran V. Ultrason. Sonochem., 2014, 21:619
[19]. Soltani Rad M.V. Ultrason. Sonochem., 2017, 34:872  
[20]. Safaei-Ghomi J., Tavazoa M., Mahdavinia G.H. Ultrason. Sonochem., 2018, 40:237 
[21]. Wang M.L., Brahmayya M., Hsieh Y.M. J. Taiwan. Inst. Chem. Eng., 2015, 57:61
[22]. Toma M., Fukutomi S., Asakura Y., Koda S. Ultrason. Sonochem., 2011, 18:197
[23]. Patil R., Bhoir P., Deshpande P., Wattamwar T., Shirude M., Chaskar P. Ultrason Sonochem., 2013, 20:1327
[24]. Piiskop S., Salmar S., Tuulmets A., Kuznetsov A., Jarv J. Ultrason. Sonochem., 2013, 20:1414
[25]. Akhbari K., Morsali A., Retailleau P., Ultrason. Sonochem., 2013, 20:1428 
[26]. Murugan E., Tamizharasu G. J. Mol. Catal. A: Chem., 2012, 363:89
[27]. Wang J., Zong Y., Fu R., Niu Y., Yue G., Quan Z., Wang X., Pan Y. Ultrason Sonochem., 2014, 21:29
[28]. Bussemaker M.J., Zhang D. Ultrason. Sonochem., 2013, 21:436      
[29]. Niemczewski B. Ultrason. Sonochem., 2014, 21:354      
[30]. Yang H.M., Lin D.W. Cataly. Commun., 2011, 14:101
[31]. Wang M.L., Rajendran V. Ultrason. Sonochem., 2007, 14:368
[32]. Murugesan V., Umapathi M.J. Ind. J. Ind.Chem., 2016, 7:441     
[33]. Abimannan P., Selvaraj V., Rajendran V. Ultrason. Sonochem., 2015, 23:164
[34]. Murugesan V., Marimuthu E., Yoganand K.S., Umapathy M.J. Ind.J. Ind. Chem., 2017, 8:241    
[35]. Halpern M., Sasson Y., Rabinovitz M. J. Org. Chem., 1984, 49:2011
[36]. Rajendran V., Wang M.L. J. Mol. Catal. A: Chem., 2008, 288:23
[37]. Sasson Y., Bilman N. J. Chem. Soc. Perkin. Trans., 1989, 2:2029
[38]. Wang M.L., Lee Z.F. J. Mol. Catal. A: Chem., 2006, 264:119
[39]. Bhatkhande B.S., Adhikari M.V., Samant S.D. Ultrason. Sonochem., 2002, 9:31
[40]. Mason T.J., Lorimer J.P. Wiley-VCH., 2002
[41]. Margulis M.A. High. Energ. Chem., 2004, 38:135
[42]. Ambulgekar G.V., Bhanage B.M., Samant S.D. Tetrahedron. Lett., 2005, 46:2483
[43]. Davidson R.S., Safdar A., Spencer J.D., Robinson B. Ultrasonics, 1987, 25:35
[44]. Lepoint T., Mullie F. Ultrason. Sonochem., 1994, 1:S13
[45]. Mahamuni N.N., Gogate P.R., Pandit A.B. Ind. Eng. Chem. Res., 2006, 45:98 
[46]. Wang M.L., Rajendran V. J. Mol. Catal. A: Chem., 2007, 273:5
[47]. Yang H.M., Peng G.Y. Ultrason. Sonochem., 2010, 17:239
[48]. Masson T.J., Cobley A.J., Graves J.E., Morgan D. Ultrason. Sonochem., 2011, 18:226
[49]. Liju W., Ablajan K., Jun F. Ultrason. Sonochem., 2015, 22:118
[50]. Kanthale P., Ashokumar M., Grieser F. Ultrason. Sonochem., 2008, 15:143            
[51]. Hatanaka S.I., Mitome H., Yausui K., Hayashi S. Ultrasonics., 2006, 44:e435
[52]. De La Rochebrochar S., Suptil J., Blais J.F., Naffrechoux E. Ultrason. Sonochem., 2012, 19:280
[53]. Koda S., Kimura T., Kondo T., Mitome H. Ultrason. Sonochem., 2003, 10:149