European Journal of Chemistry 2014, 5(3), 536-540 | doi: https://doi.org/10.5155/eurjchem.5.3.536-540.1028 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | SHORT COMMUNICATION | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals


Chandrakala Ummadisetti (1,*) , Badari Narayana Prasad Rachapudi (2) , Lakshmi Anu Prabhavathi Devi Bethala (3)

(1) Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India
(2) Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India
(3) Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India
(*) Corresponding Author

Received: 03 Feb 2014 | Revised: 20 Mar 2014 | Accepted: 20 Mar 2014 | Published: 30 Sep 2014 | Issue Date: September 2014

Abstract


Glycerol-based SO3H-functionalized carbon catalyst was demonstrated as an efficient and recyclable green catalyst for the chemoselective synthesis of pentaerythritol diacetals with aromatic aldehydes in the presence of ketones in excellent yields in toluene at 80 °C. In addition, the catalyst also has the capability for the deprotection of pentaerythritol diacetals in methanol at reflux temperature. The recovered catalyst without any pre-treatment was reused for 5 cycles without any deactivation and leaching into the reaction medium under optimum conditions.


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Reusability; Chemoselectivity; Aromatic aldehydes; Pentaerythritol diacetals; Glycerol-based SO3H-carbon catalyst; Protection and deprotection of diacetals

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.5.3.536-540.1028

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2160 times | icon graph PDF Article downloaded 801 times

Funding information


Department of Science and Technology (DST), Government of India, New Delhi, India

Citations

/


[1]. Niklas Warlin, Maria Nelly Garcia Gonzalez, Smita Mankar, Nitin G. Valsange, Mahmoud Sayed, Sang-Hyun Pyo, Nicola Rehnberg, Stefan Lundmark, Rajni Hatti-Kaul, Patric Jannasch, Baozhong Zhang
A rigid spirocyclic diol from fructose-based 5-hydroxymethylfurfural: synthesis, life-cycle assessment, and polymerization for renewable polyesters and poly(urethane-urea)s
Green Chemistry  21(24), 6667, 2019
DOI: 10.1039/C9GC03055G
/


[2]. Apurva A. Narvekar, J.B. Fernandes, S.P. Naik, S.G. Tilve
Development of glycerol based carbon having enhanced surface area and capacitance obtained by KOH induced thermochemical activation
Materials Chemistry and Physics  261, 124238, 2021
DOI: 10.1016/j.matchemphys.2021.124238
/


[3]. Mary Batista, Silvia Carvalho, Renato Carvalho, Moisés L. Pinto, João Pires
Waste-Glycerol as a Precursor for Carbon Materials: An Overview
Compounds  2(3), 222, 2022
DOI: 10.3390/compounds2030018
/


[4]. Songqi Ma, Jingjing Wei, Zhen Jia, Tao Yu, Wangchao Yuan, Qiong Li, Sheng Wang, Shusen You, Ren Liu, Jin Zhu
Readily recyclable, high-performance thermosetting materials based on a lignin-derived spiro diacetal trigger
Journal of Materials Chemistry A  7(3), 1233, 2019
DOI: 10.1039/C8TA07140C
/


[5]. Derya ÜNLÜ
Biyodizel Yan Ürünü Olan Gliserolden Üretilen Katalizör ile Yakıt Katkı Maddesi Bütil Levulinat Sentezi
Bitlis Eren Üniversitesi Fen Bilimleri Dergisi  8(1), 214, 2019
DOI: 10.17798/bitlisfen.453633
/


[6]. Apurva A. Narvekar, J.B. Fernandes, S.G. Tilve
Adsorption behavior of methylene blue on glycerol based carbon materials
Journal of Environmental Chemical Engineering  6(2), 1714, 2018
DOI: 10.1016/j.jece.2018.02.016
/


[7]. Smita V. Mankar, Maria Nelly Garcia Gonzalez, Niklas Warlin, Nitin G. Valsange, Nicola Rehnberg, Stefan Lundmark, Patric Jannasch, Baozhong Zhang
Synthesis, Life Cycle Assessment, and Polymerization of a Vanillin-Based Spirocyclic Diol toward Polyesters with Increased Glass-Transition Temperature
ACS Sustainable Chemistry & Engineering  7(23), 19090, 2019
DOI: 10.1021/acssuschemeng.9b04930
/


[8]. Peng Wang, Shuai Zhang, Wanghezi Xu, Tianming Xiao, Qichao Ran
High Heat-Resistant and Degradable Polybenzoxazines with a Diacetal Structure
ACS Sustainable Chemistry & Engineering  9(23), 7913, 2021
DOI: 10.1021/acssuschemeng.1c01919
/


[9]. Linze Liu, Yiqinq Xia, Lian Wang, Rui Shi, Shuai Yan, Xingyu Zhao, Yongzhong Jin, Yuping Sheng
Cyanate Ester Resin with High Heat‐Resistance and Degradable Diacetal Structure: Synthesis, Polymerization, and Properties
Macromolecular Materials and Engineering  307(11), 2200423, 2022
DOI: 10.1002/mame.202200423
/


[10]. Brandon Andrade-Gagnon, Marilyne Bélanger-Bouliga, Phuong Trang Nguyen, Thi Hong Diep Nguyen, Steve Bourgault, Ali Nazemi
Degradable Spirocyclic Polyacetal-Based Core-Amphiphilic Assemblies for Encapsulation and Release of Hydrophobic Cargo
Nanomaterials  11(1), 161, 2021
DOI: 10.3390/nano11010161
/


References


[1]. Taylor, P. Mechanism and Synthesis, Royal Society of Chemistry, Cambridge, UK. 2002, 32.

[2]. Brown, J.; Lenhard, R. H.; Berstein, S. J. Am. Chem. Soc. 1964, 86, 2183-2187.
http://dx.doi.org/10.1021/ja01065a016

[3]. Saniger, E.; Campos, J. M.; Entrena, A.; Marchal, J. A.; Boulaiz, H.; Aranega, A.; Gallo, M. A.; Espinosa, A. Tetrahedron 2003, 59, 8017-8026.
http://dx.doi.org/10.1016/j.tet.2003.08.016

[4]. Bruns, K.; Conrad, J.; Steigel, A. Tetrahedron 1979, 35, 2523-2530.
http://dx.doi.org/10.1016/0040-4020(79)88015-1

[5]. Marrian, S. F. Chem. Rev. 1948, 43, 149-202.
http://dx.doi.org/10.1021/cr60134a004

[6]. Zhang, Z. H.; Li, T. S.; Jin, T. S.; Li, J. T. J. Chem. Res. (S). 1998, 10, 640-641.
http://dx.doi.org/10.1039/a803046d

[7]. Perner, J.; Stork, K.; Merger, F.; Oppenlaender, K. Ger. Offen, 1978, 2707875 (Chem. Abstr. 1978, 89, 181503x).

[8]. Jin, T.; Yang, M.; Wang, X.; Feng, G.; Li, T. J. Chem. Res. 2004, 3, 203-205.
http://dx.doi.org/10.3184/0308234041640654

[9]. Jermy, B. R.; Pandurangan, A. Catal. Comm. 2006, 7, 921-925.
http://dx.doi.org/10.1016/j.catcom.2006.03.021

[10]. Deng, G.; Ren, T. J. Chem. Res. 2003, 1, 24-25.
http://dx.doi.org/10.3184/030823403103172805

[11]. Jin, T. S.; Li, T. S.; Zhang, Z. H. Synth. Commun. 1999, 29, 1601-1606.
http://dx.doi.org/10.1080/00397919908086141

[12]. Jin, T. S.; Ma, Y. R.; Li, T. S. J. Chem. Res. (S). 1999, 268-269.

[13]. Wang, G.; Song, G.; Yang, T.; Yang, L.; Suo, J. J. Mol. Catal A: Chem. 2005, 233, 121-126.
http://dx.doi.org/10.1016/j.molcata.2005.02.006

[14]. Wang, Y.; Xu, Y. N.; Wang, Z. Z.; Dai, L. Y. Chin. Chem. Lett. 2010, 21, 524-528.
http://dx.doi.org/10.1016/j.cclet.2009.12.014

[15]. Jermy, B. R.; Pandurangan, A. J. Mol. Catal A: Chem. 2006, 256, 184-192.
http://dx.doi.org/10.1016/j.molcata.2006.04.045

[16]. Shaterian, H. R.; Rigi, F. Chin. J. Chem. 2012, 30, 695-698.
http://dx.doi.org/10.1002/cjoc.201280002

[17]. Shaterian, H. R.; Azizi, K.; Fahimi, N. Chem. Sci. Trans. 2012, 1(1), 85-90.
http://dx.doi.org/10.7598/cst2012.141

[18]. Hara, M.; Yoshida, T.; Takagaki, A.; Takata, T.; Kondo, J. N.; Hayash, S.; Domen, K. Angew. Chem. Int. Ed. 2004, 43, 2955-2958.
http://dx.doi.org/10.1002/anie.200453947

[19]. Toda, M.; Takagaki, A.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Dome, K.; Hara, M. Nature 2005, 438, 178-178.
http://dx.doi.org/10.1038/438178a

[20]. Takagaki, A.; Toda, M.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Domen, K.; Hara, M. Catal. Today 2006, 116, 157-161.
http://dx.doi.org/10.1016/j.cattod.2006.01.037

[21]. Zong, M. H.; Duan, Z. Q.; Lou, W. Y.; Smith, T. J.; Wu, H. Green Chem. 2007, 9, 434-437.
http://dx.doi.org/10.1039/b615447f

[22]. Prabhavaeti Devi, B. L. A.; Gangadhar, K. N.; Prasad, P. S. S.; Jagannadh, B.; R. B. N. Prasad, Chem. Sus. Chem. 2009, 2, 617-620.
http://dx.doi.org/10.1002/cssc.200900097

[23]. Prabhavaeti Devi, B. L. A.; Gangadhar, K. N.; Kumar, K. L. N. S.; Sanker, K. S.; Prasad, R. B. N.; Prasad, P. S. S. J. Mol. Cat. A: Chem. 2011, 345, 96-100.
http://dx.doi.org/10.1016/j.molcata.2011.05.025

[24]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D.; Vijayalakhsmi, K.; Prabhavaeti Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1126-1129.
http://dx.doi.org/10.1016/j.tetlet.2011.12.092

[25]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Nageswar, Y. V. D.; Reddy, T. V. K.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1968-1973.
http://dx.doi.org/10.1016/j.tetlet.2012.02.018

[26]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Vijay, M.; Prabhavaeti Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 2636-2638.
http://dx.doi.org/10.1016/j.tetlet.2012.03.051

[27]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Chandrakala, U.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 3497-3501.
http://dx.doi.org/10.1016/j.tetlet.2012.04.122

[28]. Rao, B. M.; Reddy, G. N.; Reddy, T. V. K.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N.; Yadav, J. S.; Reddy, B. V. S.; Tetrahedron Lett. 2013, 54, 2466-2471.
http://dx.doi.org/10.1016/j.tetlet.2013.02.089

[29]. Gangadhar, K. N.; Vijay, M.; Prasad, R. B. N.; Prabhavathi Devi, B. L. A. Green Sust. Chem. 2013, 3, 122-218.

[30]. Manneganti, V.; Rachapudi, B. N. P.; Bethala, L. A. P. D. Eur. J. Chem. 2014, 5(1), 167-170.
http://dx.doi.org/10.5155/eurjchem.5.1.167-170.917


How to cite


Ummadisetti, C.; Rachapudi, B.; Bethala, L. Eur. J. Chem. 2014, 5(3), 536-540. doi:10.5155/eurjchem.5.3.536-540.1028
Ummadisetti, C.; Rachapudi, B.; Bethala, L. Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals. Eur. J. Chem. 2014, 5(3), 536-540. doi:10.5155/eurjchem.5.3.536-540.1028
Ummadisetti, C., Rachapudi, B., & Bethala, L. (2014). Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals. European Journal of Chemistry, 5(3), 536-540. doi:10.5155/eurjchem.5.3.536-540.1028
Ummadisetti, Chandrakala, Badari Narayana Prasad Rachapudi, & Lakshmi Anu Prabhavathi Devi Bethala. "Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals." European Journal of Chemistry [Online], 5.3 (2014): 536-540. Web. 3 Jun. 2023
Ummadisetti, Chandrakala, Rachapudi, Badari, AND Bethala, Lakshmi. "Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.5.3.536-540.1028


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2014, 5(3), 536-540 | doi: https://doi.org/10.5155/eurjchem.5.3.536-540.1028 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.