Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate

doi:10.1016/S1872-2067(14)60280-1

催化学报 ›› 2015, Vol. 36 ›› Issue (4): 595-602.DOI: 10.1016/S1872-2067(14)60280-1

Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate

Abdol R. Hajipour^a,b, Hirbod Karimi^a,c, Amir Masti^a

a Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran;
b Department of Neuroscience, University of Wisconsin, Medical School, Madison, WI 53706-1532, USA;
c Young Researchers and Elite Club, Shahreza Branch, Islamic Azad University, Shahreza, Iran

收稿日期:2014-11-24 修回日期:2014-12-26 出版日期:2015-03-23 发布日期:2015-03-23
通讯作者: Abdol R. Hajipour
基金资助:
This work was supported by the Isfahan University of Technology (IUT), IR Iran.

Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate

Abdol R. Hajipour^a,b, Hirbod Karimi^a,c, Amir Masti^a

a Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran;
b Department of Neuroscience, University of Wisconsin, Medical School, Madison, WI 53706-1532, USA;
c Young Researchers and Elite Club, Shahreza Branch, Islamic Azad University, Shahreza, Iran

Received:2014-11-24 Revised:2014-12-26 Online:2015-03-23 Published:2015-03-23
Supported by:
This work was supported by the Isfahan University of Technology (IUT), IR Iran.

摘要/Abstract

摘要：

Iron zirconium phosphate (ZPFe) nanoparticles were found to function as an efficient catalyst for the acetylation of a wide range of alcohols and phenols using acetic anhydride, generating good to excellent yields under solvent-free conditions. The steric and electronic properties of various substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively coupled plasma-optical emission spectrometry, X-ray diffraction, N₂ adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 9.3 Å when Fe³⁺ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. This new method for the acetylation of alcohols and phenols has several important advantages, including mild and environmentally friendly reaction conditions, as well as good to excellent yields and a facile work-up.

关键词: Iron zirconium phosphate, Nanoparticle, Acetylation, Alcohol, Phenol, Solvent-free condition, Solid catalyst

Abstract:

Key words: Iron zirconium phosphate, Nanoparticle, Acetylation, Alcohol, Phenol, Solvent-free condition, Solid catalyst

Abdol R. Hajipour, Hirbod Karimi, Amir Masti. Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate[J]. 催化学报, 2015, 36(4): 595-602.

Abdol R. Hajipour, Hirbod Karimi, Amir Masti. Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate[J]. Chinese Journal of Catalysis, 2015, 36(4): 595-602.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(14)60280-1

https://www.cjcatal.com/CN/Y2015/V36/I4/595

参考文献

[1] Gan H M, Zhao X G, Song B N, Guo L, Zhang R, Chen C, Chen J Z, Zhu W W, Hou Z S. Chin J Catal (干慧媚, 赵秀阁, 宋宝宁, 郭立, 张然, 陈晨, 陈吉忠, 朱闻闻, 侯震山. 催化学报), 2014, 35: 1148
[2] Sun L, Boo W J, Sue H J, Clearfield A. New J Chem, 2007, 31: 39
[3] Hajipour A R, Karimi H. Mater Lett, 2014, 116: 356
[4] Sun Z Y, Liu Z, Xu L, Yang Y, He Y. Stud Surf Sci Catal, 2004, 154: 1060
[5] Shi Q S, Tan S Z, Ouyang Y S, Yang Q H, Chen A M, Li W R, Shu X L, Feng J, Feng J, Chen Y B. Adv Mater Res, 2011, 151-152: 852
[6] Cai X, Dai G J, Tan S Z, Ouyang Y, Ouyang Y S, Shi Q S. Mater Lett, 2012, 67: 199
[7] Wang Q, Yu J F, Liu J J, Guo Z H, Umar A, Sun L Y. Sci Adv Mater, 2013, 5: 469
[8] Clearfield A, Kalnins J M. J Inorg Nuc Chem, 1978, 40: 1933
[9] Gawande M B, Deshpande S S, Sonavane S U, Jayaram R V. J Mol Catal A, 2005, 241: 151
[10] Khare S, Chokhare R. J Mol Catal A, 2011, 344: 83
[11] Giannoccaro P, Gargano M, Fanizzi A, Ferragina C, Aresta M. Appl Catal A, 2005, 284: 77
[12] Pet'kov V I, Markin A V, Shchelokov I A, Sukhanov M V, Smirnova N N. Russ J Phys Chem, 2007, 81: 1728
[13] Yang Y H, Dai G J, Tan S Z, Liu Y L, Shi Q S, Ouyang Y S. J Rare Earths, 2011, 29: 308
[14] Dai G J, Yu A L, Cai X, Shi Q S, Ouyang Y S, Tan S Z. J Rare Earths, 2012, 30: 820
[15] Zhang Q R, Du W, Pan B C, Pan B J, Zhang W M, Zhang Q J, Xu Z W, Zhang Q X. J Hazard Mater, 2008, 152: 469
[16] Costantino U, Szirtes L, Kuzmann E, Megyeri J, Lázár K. Solid State Ionics, 2001, 141-142: 359
[17] Gobechiya E R, Kabalov Y K, Orlova A I, Trubach I G, Bykov D M, Kurazhkovskaya V S. Crystallogr Rep, 2004, 49: 390
[18] Khare S, Chokhare R. J Mol Catal A, 2012, 353-354: 138
[19] Wang X Y, Hua W M, Yue Y H, Gao Z. Chem J Chin Univ, 2013, 34: 1913
[20] Pylinina A I, Mikhalenko I I. Russ J Phys Chem A, 2013, 87: 372
[21] Pylinina A I, Mikhalenko I I. Russ J Phys Chem A, 2011, 85: 2109
[22] Hajipour A R, Karimi H, Karimzadeh M. Monatsh Chem, 2014, 145: 1461
[23] Hajipour A R, Karimi H. Chin J Catal (催化学报), 2014, 35: 1529
[24] Hajipour A R, Karimi H. Chin J Catal (催化学报), 2014, 35: 1982
[25] Yoon H J, Lee S M, Kim J H, Cho H J, Choi J W, Lee S H, Lee Y S. Tetrahedron Lett, 2008, 49: 3165
[26] Sharghi H, Jokar M, Doroodmand M M. Adv Synth Catal, 2011, 353: 426
[27] Taghavi S A, Moghadam M, Mohammadpoor-Baltork I, Tangestaninejad S, Mirkhani V, Khosropour A R. Inorg Chim Acta, 2011, 377: 159
[28] Montes I, Sanabria D, García M, Castro J, Fajardo J. J Chem Educ, 2006, 83: 628
[29] Reddy T S, Narasimhulu M, Suryakiran N, Mahesh K C, Ashalatha K, Venkateswarlu Y. Tetrahedron Lett, 2006, 47: 6825
[30] Prajapti S K, Nagarsenkar A, Babu B N. Tetrahedron Lett, 2014, 55: 1784
[31] Khaligh N G, Ghasem-Abadi P G. Chin J Catal (催化学报), 2014, 35: 1126
[32] Yadav P, Lagarkha R, Balla Z A. Asia J Chem, 2010, 22: 5155
[33] Osiglio L, Romanelli G, Blanco M. J Mol Catal A, 2010, 316: 52
[34] Tamaddon F, Amrollahi M A, Sharafat L. Tetrahedron Lett, 2005, 46: 7841
[35] Dalpozzo R, De Nino A, Maiuolo L, Procopio A, Nardi M, Bartoli G, Romeo R. Tetrahedron Lett, 2003, 44: 5621
[36] Gupta R, Kumar V, Gupta M, Paul S, Gupta R. Indian J Chem Sec B, 2008, 47B: 1739
[37] Tayebee R, Cheravi F. Bull Korean Chem Soc, 2009, 30: 2899
[38] Liu Z H, Ma Q Q, Liu Y X, Wang Q M. Org Lett, 2014, 16: 236
[39] Chakraborti A K, Gulhane R, Shivani. Synthesis, 2004: 111
[40] Niknam K, Saberi D. Appl Catal A, 2009, 366: 220
[41] Lakshmi Kantam M, Aziz K, Likhar P R. Catal Commun, 2006, 7: 484
[42] Wang W J, Cheng W P, Shao L L, Yang J G. Catal Lett, 2008, 121: 77
[43] Liu Y, Liu L, Lu Y, Cai Y Q. Monatsh Chem, 2008, 139: 633
[44] Yue C B, Liu Q Q, Yi T F, Chen Y. Monatsh Chem, 2010, 141: 975
[45] Shirini F, Zolfigol M A, Abedini M. Monatsh Chem, 2009, 140: 1495
[46] Niknam K, Saberi D. Tetrahedron Lett, 2009, 50: 5210
[47] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 695
[48] Hajjami M, Ghorbani-Choghamarani A, Norouzi M. Chin J Catal (催化学报), 2012, 33: 1661
[49] Nowrouzi N, Alizadeh S Z. Chin J Catal (催化学报), 2013, 34: 1787
[50] Ghorbani-Choghamarani A, Pourbahar N. Chin J Catal (催化学报), 2012, 33: 1470
[51] Farhadi S, Jahanara K. Chin J Catal (催化学报), 2014, 35: 368
[52] Zarei A, Hajipour A R, Khazdooz L. Synth Commun, 2011, 41: 1772
[53] Hajipour A R, Khazdooz L, Ruoho A E. J Chin Chem Soc, 2009, 56: 398
[54] Kumar P, Pandey R K, Bodas M S, Dagade S P, Dongare M K, Ramaswamy A V. J Mol Catal A, 2002, 181: 207
[55] Iqbal J, Srivastava R R. J Org Chem, 1992, 57: 2001
[56] Dehghani F, Sardarian A R, Doroodmand M M. J Iran Chem Soc, 2014, 11: 673
[57] Constantinou-Kokotou V, Peristeraki A. Synth Commun, 2004, 34: 4227
[58] Alam M, Rahman A, Alandis N M, Shaik M R. Arabian J Chem, 2014, 7: 53
[59] Esmaeilpour M, Sardarian A R. Iran J Sci Technol, Trans A: Sci, 2014, 38: 175
[60] Shirini F, Akbari-Dadamahaleh S, Mohammad-Khah A, Aliakbar A R. C R Chim, 2014, 17: 164
[61] Meshram G, Patil V D. Synth Commun, 2009, 39: 4384
[62] Farhadi S, Jahanara K, Sepahdar A. J Iran Chem Soc, 2014, 11: 1103
[63] Rajabi F, Luque R. Catal Commun, 2014, 45: 129
[64] Hajipour A R, Karimi H. Appl Catal A, 2014, 482: 99
[65] Hajipour A R, Karimi H. Chin J Catal (催化学报), 2014, 35: 1136
[66] Bingham P A, Hannant O M, Reeves-McLaren N, Stennett M C, Hand R J. J Non Cryst Solids, 2014, 387: 47
[67] Pandit A A, Shitre A R, Shengule D R, Jadhav K M. J Mater Sci, 2005, 40: 423
[68] Sing K S W, Everett D H, Haul R A W, Moscou L, Pierotti R A, Rouquerol J, Siemieniewska T. Pure Appl Chem, 1985, 57: 603

Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate

Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate

PDF

可视化

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics

[1]	Francesca Liguori, Carmen Moreno-Marrodan, Pierluigi Barbaro. Metal nanoparticles immobilized on ion-exchange resins: A versatile and effective catalyst platform for sustainable chemistry[J]. 催化学报, 2015, 36(8): 1157-1169.
[2]	Abdol R. Hajipour, Hirbod Karimi, Afshin Koohi. Selective oxidation of alcohols over nickel zirconium phosphate[J]. 催化学报, 2015, 36(7): 1109-1116.
[3]	Sneha Yadav, Jitender M. Khurana. Cinnamomum tamala leaf extract-mediated green synthesis of Ag nanoparticles and their use in pyranopyrazles synthesis[J]. 催化学报, 2015, 36(7): 1042-1046.
[4]	Sanjay Srivastava, Pravakar Mohanty, Jigisha K. Parikh, Ajay K. Dalai, S. S. Amritphale, Anup K. Khare. Cr-free Co-Cu/SBA-15 catalysts for hydrogenation of biomass-derived α-, β-unsaturated aldehyde to alcohol[J]. 催化学报, 2015, 36(7): 933-942.
[5]	Alireza Khorshidi, Shahab Shariati. Efficient synthesis of 3, 3'-bisindoles catalyzed by Fe₃O₄@MCM-48-OSO₃H magnetic core-shell nanoparticles[J]. 催化学报, 2015, 36(5): 778-784.
[6]	Keyvan Bijanzad, Azadeh Tadjarodi, Omid Akhavan. Photocatalytic activity of mesoporous microbricks of ZnO nanoparticles prepared by the thermal decomposition of bis(2-aminonicotinato) zinc (II)[J]. 催化学报, 2015, 36(5): 742-749.
[7]	Hossein Naeimi, Hossein Foroughi. Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions[J]. 催化学报, 2015, 36(5): 734-741.
[8]	Nasir Iravani, Mosadegh Keshavarz, Hossein Ali Shojaeian Kish, Rasool Parandvar. Tin sulfide nanoparticles supported on activated carbon as an efficient and reusable Lewis acid catalyst for three-component one-pot synthesis of 4H-pyrano[2, 3-c]pyrazole derivatives[J]. 催化学报, 2015, 36(4): 626-633.
[9]	Hassan Kefayati, Mostafa Golshekan, Shahab Shariati, Mahsa Bagheri. Fe₃O₄@MCM-48-SO₃H: An efficient magnetically separable nanocatalyst for the synthesis of benzo[f]chromeno[2, 3-d]pyrimidinones[J]. 催化学报, 2015, 36(4): 572-578.
[10]	Farzaneh Ahmadi, Jahan Bakhsh Raoof, Reza Ojani, Mehdi Baghayeri, Moslem Mansour Lakouraj, Hamed Tashakkorian. Synthesis of Ag nanoparticles for the electrochemical detection of anticancer drug flutamide[J]. 催化学报, 2015, 36(3): 439-445.
[11]	Jalal Albadi, Amir Alihosseinzadeh, Mehdi Mardani. Efficient approach for the chemoselective acetylation of alcohols catalyzed by a novel metal oxide nanocatalyst CuO-ZnO[J]. 催化学报, 2015, 36(3): 308-313.
[12]	Hossein Eshghi, Ali Javid, Amir Khojastehnezhad, Farid Moeinpour, Fatemeh F. Bamoharram, Mehdi Bakavoli, Masoud Mirzaei . Preyssler heteropolyacid supported on silica coated NiFe₂O₄ nanoparticles for the catalytic synthesis of bis(dihydropyrimidinone)benzene and 3,4-dihydropyrimidin-2(1H)-ones[J]. 催化学报, 2015, 36(3): 299-307.
[13]	Reza Ojani, Saeid Safshekan, Jahan-Bakhsh Raoof. Silver nanoparticle decorated poly(2-aminodiphenylamine) modified carbon paste electrode as a simple and efficient electrocatalyst for oxidation of formaldehyde[J]. 催化学报, 2014, 35(9): 1565-1570.
[14]	Abdol R. Hajipour, Ghobad Azizi. Immobilized Pd nanoparticles on Tris-modified SiO₂：Synthesis, characterization, and catalytic activity in Heck cross-coupling reactions[J]. 催化学报, 2014, 35(9): 1547-1554.
[15]	Abdol R. Hajipour, Hirbod Karimi. Selective oxidation of alcohols over copper zirconium phosphate[J]. 催化学报, 2014, 35(9): 1529-1533.