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Current Catalysis, 2017, 6, 000-000 1
RESEARCH ARTICLE
2211-5447/17 $58.00+.00 ©2017 Bentham Science Publishers
Green Oxidation Protocol for Alcohols to Carbonyls by Tert-
butylhydroperoxide Over MnO2 Catalysts: Comparison of Bulk and
Nanostructure
Anand S. Burange
1,2
, Ashtami Jayakumar
3
, Amber J. Sahani
1
, Savita Ladage
4
and Radha V. Jayaram
1,*
1
Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai- 400 019, India;
2
Department of Chemistry,
Wilson College, Chowpatty, Mumbai- 400 007, India.;
3
Institute for Intensive Research in Basic Science (IIRBS,Mahatma
Gandhi University, Priyadarshini Hills P.O Kottayam, Kerala 686560, India and
4
Homi Bhabha Centre for Science
Education,Tata Institute of Fundamental Research,V.N. Purav Marg, Mankhurd, Mumbai 400088, India
Abstract: Background: There are various conventional ways for the synthesis of aromatic ketones but
suffer from disadvantages like the use of toxic reagents, stoichiometric reagents producing huge amount
of byproducts, thus causing hazard to the environment, whereas homogeneous protocols or the noble
metal which support catalytic processes are not economically viable. On this ground, an effort was
made to develop new green catalytic protocol to overcome these environmental concerns. The catalytic
activity of manganese dioxides prepared by different recipes was investigated for the oxidation of allylic
and benzylic alcohols.
Methods: MnO2
B
sample was prepared by calcinations of manganese nitrate while sample ANMnO2
was prepared by the reduction of potassium permanganate using triethanolamine as a reductant. All the
samples were well characterized by XRD, SEM, EDX and TEM techniques. All the prepared catalyst
samples along with commercial MnO2 were tested for the oxidation of alcohols using TBHP as a clean
oxidant, where % conversion and % selectivity were determined by Gas Chromatography. The products
were further confirmed by the GC-MS and NMR techniques.
Results: Of all the oxides, nano amorphous manganese dioxide exhibited significant catalytic activity
and selectivity for the corresponding carbonyls. Change from bulk to nano structure enhanced the
catalytic activity because of its higher surface area and change in Mn
3+
/ Mn
4+
ratio. The nano
amorphous MnO2 (ANMnO2)/TBHP in acetonitrile solvent catalytic system was found to be most
efficient with substrate compatibility. In mechanistic investigations, it was observed that from the bulk
to the nano structure, Mn
3+
species content in an oxide increased which may play a crucial role in the
activity. It was also confirmed by hydrogen peroxide decomposition studies. The catalyst ANMnO2 was
found to be reusable for five consecutive cycles with no significant loss in catalytic activity.
Conclusion: In conclusion, change in the catalyst’s preparation recipe not only alters the particle size
but also affects the ratio of Mn
3+
to Mn
4+
species on the surface as well as on the bulk and thereby
catalytic activity. On comparison of initial rate m
-2
g of all the catalyst samples for the said reaction,
there was no significant difference observed which clearly proved the role of Mn
3+
in catalytic activity.
A R T I C L E H I S T O R Y
Received: October 13, 2016
Revised: December 31, 2016
Accepted: January 7, 2017
DOI:
10.2174/22115447066661701171223
25
Keywords: Manganese dioxide, amorphous catalysis, nanomaterials, oxidation, nanocatalysis.
1. INTRODUCTION
Alcohol oxidation to a carbonyl is one of the most
important transformation for the synthesis of variety of
intermediates in synthetic organic chemistry [1-2]. Aromatic
ketones and carbonyls are usually prepared by Friedel crafts
acylation [3-5] or cross-coupling reactions [6-7], apart from
*Address correspondence to this author at the Department of Chemistry,
Head, Chemistry Department at Institute of Chemical Technology,
Matunga, Mumbai, Maharashtra, India; Tel/Fax: + 91 22 3361 2607, +91 22
3361 1020; E-mails: rv.jayaram@ictmumbai.edu.in
the oxidation of alcohols. Traditional route for the synthesis
of aromatic ketones involves the use of a stoichiometric
amount of oxidants such as permanganate and dichromate,
but these reagents are toxic and non-ecofriendly causing
serious environmental problems [8-10]. Noble metals
supported on metal oxides showed promising catalytic
activity [11-13], but they are not economically viable.
In the last few decades, the stoichiometric reagents for
oxidation reaction were gradually replaced by various
catalytic systems, including homogeneous and
heterogeneous catalysts. This includes many homogeneous