Glycerol-based deep eutectic solvents: Physical properties
Mohamed Khalid AlOmar
a,b
, Maan Hayyan
a,b,
⁎, Mohammed Abdulhakim Alsaadi
b,c
, Shatirah Akib
d
,
Adeeb Hayyan
b,e
, Mohd Ali Hashim
b,e
a
Department of Civil Engineering, Faculty of Engineering, University of Malaya, Kuala Lumpur 50603, Malaysia
b
University of Malaya Centre for Ionic Liquids, University of Malaya, Kuala Lumpur 50603, Malaysia
c
Nanotechnology & Catalysis Research Centre (NANOCAT), IPS Building, University of Malaya, 50603 Kuala Lumpur, Malaysia
d
School of Energy, Geoscience, Infrastructure and Society (EGIS), Heriot-Watt University Malaysia, 62200 Putrajaya, Malaysia
e
Department of Chemical Engineering, Faculty of Engineering, University of Malaya, Kuala Lumpur 50603, Malaysia
abstract article info
Article history:
Received 15 August 2015
Received in revised form 20 November 2015
Accepted 22 November 2015
Available online xxxx
Deep eutectic solvents (DESs) have been used in many industrial applications. DES is a mixture of a salt and a
hydrogen bond donor (HBD). In this study, 70 DESs were synthesized successfully based on glycerol (Gly) as
the HBD with different phosphonium and ammonium salts, namely methyl triphenyl phosphonium bromide
(MTPB), benzyl triphenyl phosphonium chloride (BTPC), allyl triphenyl phosphonium bromide (ATPB), choline
chloride (ChCl), N,N-diethylethanolammonium chloride (DAC), and tetra-n-butylammonium bromide (TBAB).
The DESs were prepared using different molar ratios of the HBD to the salts. The freezing point of each DES
was determined using Differential Scanning Calorimetry (DSC). The physical properties of these DESs, including
density, viscosity, conductivity, and surface tension, were investigated as functions of temperature. In addition,
the functional groups were analyzed utilizing Fourier transform infrared (FTIR) spectroscopy. It is worth noting
that these systems have a wide variety of physical properties, which implies that these DESs would be suitable for
diverse applications.
© 2015 Elsevier B.V. All rights reserved.
Keywords:
Deep eutectic solvent
Choline chloride
Ionic liquid
Methyl triphenyl phosphonium bromide
N,N-diethyl ethanol ammonium chloride
1. Introduction
In the last two decades, there has been increasing interest in the
applications of ionic liquids (ILs), especially with respect to catalysts,
electrochemistry process technology and analytics, biotechnology, and
functional liquids. ILs are solvents which consist solely of ions. Mainly,
the synthesis of ILs can be split into two distinct categories, those
formed from eutectic mixtures of metal halides and organic salts, and
those containing discrete anions [1]. Due to the increasing need for
organic solvents and the high cost of ILs [2], researchers recently have
focused on ionic liquid analogues, i.e., deep eutectic solvents (DESs),
which were introduced by Abbot et al. in 2003 [3]. Basically, DESs are
mixtures of two or more compounds, and the mixtures have a melting
point that is lower than that of the individual compounds [4,5]. Further-
more, DESs are prepared by mixing a salt and a hydrogen bond donor
(HBD), hence, the hydrogen bonds with the anion of the salt. DESs can
be made from different kinds of salts (organic and inorganic) and differ-
ent kinds of HBDs [2]. The physicochemical properties of DESs are much
like those of conventional ILs [6]. However, DESs have many advantages
over conventional ILs, including the simplicity of the synthesis, lower
production cost, low or negligible toxicity profiles, and sustainability
with respect to environmental and economic benefits [6–8].
Recently, DESs have been reported in many applications, one of
which was the use of ChCl-based DESs as functional additives for
starch-based plastics [9]. Also, they have been used as catalysts for the
production of biodiesel fuel from low grade palm oil [10,11], as an elec-
trolyte in electrochemical processes such as, deposition of specific
metals in the electroplating and electroless plating of metals [12,13],
and as viable co-solvents for enzyme-catalyzed epoxide hydrolysis [14].
Glycerol is a conventional solvent that is defined simply as a polyol
(sugar alcohol), and it is used extensively in many industrial applica-
tions, especially in the food and pharmaceutical industries. However,
there is a limited use of glycerol in organic transformations due to its
low solubility in organic compounds and the intrinsic reactivity of the
polyol backbone which leads to the side product formation [15].
Therefore, to overcome these disadvantages, researchers have been
working to enhance the physicochemical properties of glycerol by
different methods [15,16]. One of these methods is preparing of DESs
containing glycerol as HBD.
In the current work, six DES systems were prepared based on glycerol
as a HBD and six different salts, i.e., methyl triphenyl phosphonium bro-
mide (MTPB); benzyl triphenyl phosphonium chloride (BTPB); allyl
triphenyl phosphonium bromide (ATPB); choline chloride (ChCl); N,N-
diethylethanolammonium chloride (DAC); and tetra-n-butylammonium
bromide (TBAB). The physical properties of these DESs were investigated,
Journal of Molecular Liquids 215 (2016) 98–103
⁎ Corresponding author at: Department of Civil Engineering, Faculty of Engineering,
University of Malaya, Kuala Lumpur 50603, Malaysia.
E-mail address: maan_hayyan@yahoo.com (M. Hayyan).
http://dx.doi.org/10.1016/j.molliq.2015.11.032
0167-7322/© 2015 Elsevier B.V. All rights reserved.
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