CHEMICAL ENGINEERING TRANSACTIONS
VOL. 83, 2021
A publication of
The Italian Association
of Chemical Engineering
Online at www.cetjournal.it
Guest Editors: Jeng Shiun Lim, Nor Alafiza Yunus, Jiří Jaromír Klemeš
Copyright © 2021, AIDIC Servizi S.r.l.
ISBN 978-88-95608-81-5; ISSN 2283-9216
NaOH-Promoted Reduction of Carbonyl Compounds Assisted
by Microwave
Uyen Phuoc Nhat Tran
Van Hien University, 613 Au Co St, Phu Trung Ward, Tan Phu Dist, Ho Chi Minh City, Viet Nam.
uyentpn@vhu.edu.vn
The reduction of aldehydes and ketones based on MPV chemistry is one of the vital transformations in organic
chemistry. In this study, MPV chemistry was developed in heating assistance of Microwave to synthesize a
broad range of alcohol with yields up to 96 % by a simple, cheap, and safe synthetic protocol. Sodium
hydroxide (NaOH) is an excellent promoter for the reduction. The method is quite cheap and straightforward
while it utilized easy-to-handle chemicals and did not require strictly anhydrous reagents, transition metals, or
any additional ligands. This potential method encourages a scale-up upgrading of Microwave use for alcohol
production.
1. Introduction
The development of sustainable synthetic methods directed recently is due to the heightened awareness of
humans and the recognition of eco-friendly and economic methodologies that minimize negative impacts on
the environment (Rathi et al., 2015). Among those, microwave-assisted methods have matured and have
been used safely to substitute for conventional heating techniques (Prieto et al., 2019). Microwave was
applied successfully in many fields such as bioenergy recovery (Ani et al., 2020), encapsulation (Muhamad et
al., 2020), phytochemical extraction (Abd Rahman et al., 2020). Also, many microwave-heated chemical
transformations have been achieved (Ni et al., 2020), thereby upgrading existing protocols to form superior
results compared to normal heated ones (Zhou et al., 2020). Esterification, oligolactic acid synthesis, aromatic
polyester synthesis are synthetic types whose methods were developed to have scale-up applications of
microwave (Nagahata and Takeuchi, 2019).
The reduction of aldehydes and ketones is one of the essential functional group transformations in organic
chemistry. Meerwein Ponndorf Verley (MPV) reduction is recognized as one of such efficient transformations
due to many desirable features such as high selectivity, mild conditions, and relatively cheap reagents (Cha,
2006). MPV reactions are normally catalyzed homogeneously by metal alkoxides such as aluminum
isopropoxide Al(OiPr)3 (Cha, 2006). The reaction proceeds a hydride transfer from alcohol to carbonyl
compound, which is coordinated to the metal center of alkoxide. The catalytic activity of these alkoxides is
related to their Lewis acidic character in combination with ligand exchangeability (Cohen et al., 2004). In
recent years, modifications of MPV reactions have been introduced to address some of the remaining
problems, including long reaction times, solvent selection, side reactions, workup issues, and catalyst
effectiveness by exploring novel catalytic systems. However, the cost and toxicity of transition metals
(Bruneau-Voisine et al., 2017) and the sophisticated preparation of ligands (Zheng et al., 2020) needed to
enhance MPV reduction are attributed to be typical drawbacks of this reaction. Boron alkoxides B(OR)3, an
environmentally friendly candidate, could catalyze MPV reductions as metal alkoxides but it remained long
reaction time, high content of alkoxides and limited subtract scope (Uysal and Oksal, 2011).
To expand upon this trend in a different approach to build up a metal-free protocol, sodium tetraborate
(Na2B4O7) was chosen as a catalyst for the MPV reaction in initial tests of this study. However, the
unnecessary presence of Na2B4O7 in those tests led us to explore another metal-free alternative. Highly
positive thermal effects of Microwave (conduction and dipolar polarization mechanism) encouraged us to use
it to replace traditional heat transfer. To achieve a more sustainable alcohol synthesis that overcomes the
weakness of alkoxide or metal catalytic system, an alkoxide-free and metal-free MPV method in the effective
combination of the low base concentration and the crucial microwave heating was developed. The base-
DOI: 10.3303/CET2183021
Paper Received: 25/06/2020; Revised: 06/08/2020; Accepted: 06/08/2020
Please cite this article as: Tran U.P.N., 2021, NaOH-Promoted Reduction of Carbonyl Compounds Assisted by Microwave, Chemical
Engineering Transactions, 83, 121-126 DOI:10.3303/CET2183021
121