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<div class="articledetails article-header clearfix">
<p class="art-type">Review Article</p>
<p class="art-title">Ionic liquids with Dimethyl Phosphate Anion as
Highly Efficient Materials for Technological
Processes: A Review</p>
<p class="art-author"><?php $authors="Andris Zicmanis<sup>*</sup> and Zeltkalne S"; echo (stristr($authors,$coauthor))?str_replace($coauthor,"<a href='".$extpath."authors/".$courl."' target='_blank'>".$coauthor."</a>",$authors):$authors; ?></p>
<p class="art-affl">
Faculty of Chemistry, University of Latvia, 19, Raina Blvd, LV-1586, Riga, Latvia
</p>
<p class="art-aff"><b>*Corresponding author: <?php $corresponding_author="Andris Zicmanis"; echo ($coauthor!="" && $coauthor==$corresponding_author)?"<a href='".$extpath."authors/".$courl."' target='_blank'>".$coauthor."</a>":$corresponding_author;?></b>, Faculty of Chemistry, University of Latvia, 19, Raina Blvd, LV-1586, Riga, Latvia, E-mail: <a href="mailto:zicmanis@latnet.lv">zicmanis@latnet.lv</a>
</p>
<p class="art-aff"><b>Received:</b> April 9, 2018
<b>Accepted:</b> April 16, 2018
<b>Published:</b> April 22, 2018</p>
<p class="art-aff"><b>Citation: </b> Zicmanis A, Zeltkalne S. Ionic
liquids with Dimethyl Phosphate Anion as
Highly Efficient Materials for Technological
Processes: A Review. <i>Int J Petrochem Res.</i>
2018; 2(1): 116-125. doi: <a href="https://doi.org/10.18689/ijpr-1000121">10.18689/ijpr-1000121</a></p>
<p class="art-aff"><b>Copyright:</b> &copy; 2018 The Author(s). This work
is licensed under a Creative Commons
Attribution 4.0 International License, which
permits unrestricted use, distribution, and
reproduction in any medium, provided the
original work is properly cited.</p>
<p><a href="<?php echo $extpath;?><?php echo $jres['journal_link'];?>/ijpr-1000121.pdf" class="btn btn-danger pull-right" target="_blank">Download PDF</a></p>
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<div class="articlecontent">
<p class="art-subhead">Abstract</p>
<p class="art-para">Petrochemistry needs stable, environmentally-friendly and efficient materials for
use in the transformation, purification, and analysis of oil products. Ionic liquids (ILs) meet these requirements. A novel group of ILs with a very specific anion &ndash; dimethyl
phosphate (DMP) ion &ndash; has appeared recently and can be designated as ILs-DMP. The
DMP anion increases hydrophilicity and allocates the complex-formation capacity to
ILs-DMP. Although these new materials have been widely used in cellulose dissolution
processes, they have not been explored sufficiently in petrochemistry. There is a reason
to believe that, in comparison with other ILs, the DMP anion can also provide additional
benefits in oil chemistry. Unfortunately, no collected information is available about ILsDMP
in literature. The information presented in the review can pave the way to new
applications of these unique materials.</p>
<p class="art-para"><b>Keywords:</b> Ionic liquids, Dimethyl phosphate anion, Preparation, Analysis, Applications.</p>
<p class="art-subhead">Introduction</p>
<p class="art-para">Ionic liquids (ILs) have gained a stable position in technology and research in the
last quarter of the 20th century. The possibility to adjust their structures to the application
needs until the best match is reached is the biggest advantage of ILs in comparison with
conventional molecular organic solvents (MOSs). The negligible vapor pressure that
removes their volatility, followed by a threat of ignition or poisoning, the great ability to
dissolve the most diverse substances, and other features are noted when discussing ILs. Therefore, it does not come as a surprise that ILs are used in various branches of both
industry and science, and new applications of ILs appear frequently <a href="#1">[1]</a> <a href="#2">[2]</a> <a href="#3">[3]</a>. To date, more than 240 review articles about ILs have been published. New review papers about
some significant areas of their use have already appeared this year, for instance, about
the conversion of carbohydrates into value-added small molecules <a href="#4">[4]</a>, about the
thermal, electrochemical and radiolytic stability of ILs <a href="#5">[5]</a>, about the use of ILs in lithium
and sodium batteries <a href="#6">[6]</a>, for CO2/CH4 and H2S/CO<sub>2</sub> separations <a href="#7">[7]</a>, and others.</p>
<p class="art-para">ILs with dialkyl phosphate anions and, most frequently, with the dimethyl
phosphate anion (ILs-DMP), can be considered as newcomers in the large family
of ILs. Even if they have formally been known for more than a half of century
since the first patent in 1951 <a href="#8">[8]</a>, ILs-DMP attracted the attention of specialists
only after the famous publication of the extensive research of the Wasserscheid&#700;s
group about these materials <a href="#9">[9]</a> that have properties noticeably superior to
other ILs in almost all indicators. ILs-DMP have different cations that, for the
most part, are 1,3-dialkylimidazolium ions. Unquestionably, the greatest asset of ILs-DMP is their ability to dissolve cellulose, the most
common biopolymer in nature. Investigations of other
uses of ILs-DMP started after the highly successful
dissolution of cellulose. ILs-DMP form a separate group of
ILs, and ILs with other dialkyl phosphate anions are usually
included in this group. For all that, no specialized review
article is available about ILs-DMP that would critically
evaluate the properties of these prospective materials
and their possible applications. The present review is
intended to contribute to filling this shortage.</p>
<p class="art-subhead">Preparation</p>
<p class="art-para">Presently, ILs-DMP are prepared using two methods
both in industry and in laboratories: by the alkylation of
amines (phosphines, nitrogen heterocycles) (Scheme 1) and by the alkylation of the chloride anion in pre-made
ILs that have this anion (Scheme 2).</p>
<p class="art-para">The alkylation of amines, phosphines or nitrogen
heterocycles is the first and most widespread type of
production of ILs-DMP. Alkylation with trimethyl
phosphate is usually carried out by stirring reagents at
80&ndash;100 &deg;C for 24&ndash;48 h under helium, argon or nitrogen
<a href="#9">[9]</a>, with a small molar excess of trimethyl phosphate. Alkylation with other trialkyl phosphates requires more
severe conditions. So, reactions between tertiary amines
and triethyl phosphate come to an end only at 120 &deg;C
after 24&ndash;48 h, while reactions with tributyl phosphate
demand a temperature 160 &deg;C for 72 h <a href="#9">[9]</a>. These
alkylation reactions are carried out in aprotic solvents, such as toluene, ethyl acetate, acetonitrile, and others
<a href="#9">[9]</a> <a href="#10">[10]</a>. No unanimous opinion exists among researchers
about the best solvent for these reactions. The choice of
the solvent used largely depends on the established
practice in each specific laboratory. The use of ketones (acetone, 2-butanone) as solvents is undesirable in
synthesizing ILs-DMP due to the staining of the products (ILs-DMP) that is very difficult to remove. Even repeated
treatment of the stained IL-DMP solutions in the solution
of methanol with charcoal does not eliminate the
unwanted color. ILs-DMP are remarkably hygroscopic
materials. Therefore, their protection from contact with
air moisture is indispensable. Some researchers perform
the synthesis successfully in tightly closed containers, most frequently in a steel cylinder that allows easier
protection of the reaction mixture from contact with air, or use solvents with lower boiling temperatures. Pure
ILs-DMP can be obtained when exact reaction conditions
are maintained, and only the solvent and its residue
should be removed from the reaction mixture after the
synthesis. This can be done in different ways, and
probably the best procedure is simple rinsing of the
product with ethyl acetate for several times, followed by
vacuum drying of the purified product. The whole
process is time-consuming. Fortunately, the yields of
ILs-DMP are high with alkylation (= 95%). Notably, if the
product is colored yellow or brown, it is always possible to
cleanse it by treating its methanol solution with charcoal
for several times, until the solution becomes colorless. Needless to say, each purification leads to a decrease in
yield. At the same time, the otherwise good method, the
alkylation reaction, has a serious limitation: a methyl group
is introduced in the IL-DMP cation simultaneously with the
formation of the anion. Fortunately, the presence of the
methyl group usually is not an obstacle for use of the
prepared ILs-DMP. The obtaining of a popular IL-DMP
&ndash; 1-butyl-3-methylimidazolium dimethyl phosphate &ndash; is
shown below just for illustration (Scheme 1).</p>
<div class="art-img">
<img src="<?php echo $imgpath;?>images/IJPR-121-scheme1.PNG" class="img-responsive center-block"/></div>
<p class="art-para">According to the second method, ILs-DMP are
prepared by alkylation with the trimethyl phosphate of
a pre-made salt, which has the chloride anion in its
structure, such as ammonium, phosphonium, or nitrogen
heterocyclic onium chlorides <a href="#11">[11]</a> <a href="#12">[12]</a>. In fact, it is the
alkylation of the chloride anion. The mixture of the salt
and trimethyl phosphate is stirred and heated at 100&ndash; 120 &deg;C for that purpose, the end of the gas (chloromethane) evaluation signaling for the end of the
reaction. This anion metathesis reaction greatly increases
the diversity of the substances to be obtained and removes
the main constraint of the first method, the compulsory
introduction of a methyl group in the cations of ILs-DMP, thus expanding the range of available ILs-DMP. The
synthesis of 1-butyl-3-octylimidazolium dimethyl
phosphate is presented below for the illustration of the
method (Scheme 2).</p>
<div class="art-img">
<img src="<?php echo $imgpath;?>images/IJPR-121-scheme2.PNG" class="img-responsive center-block"/></div>
<p class="art-subhead">Analysis</p>
<p class="art-para">Both traditional and quite specific analytical methods
are used for the characterization of ILs-DMP. The choice
of the analyses mainly depends on the utilization needs
of ILs-DMP.</p>
<p class="art-para"><b>Traditional methods</b></p>
<p class="art-para">The most widely used analytical method of ILs-DMP
is the high performance liquid chromatography (HPLC), in a tandem with mass spectrometry. Traditional and
highly advanced instruments are used in these analyses, and the method can be considered as both a qualitative
and quantitative analytical method. Another required
analysis of ILs-DMP is the determination of the moisture
content in them using the Karl Fisher titration method, taking into account the high hygroscopicity of these materials. Thermogravimetry can be mentioned as the
third required analysis of ILs-DMP that limits the
temperature interval for the use of these materials. The
type of the cation is mainly responsible for the thermal
stability of ILs-DMP. Heterocyclic imidazolium DMPs are
highly heat-resistant substances that can be heated up to
280&ndash;340 &deg; C, while aliphatic tetraalkylammonium salts
decompose as early as at temperatures starting from
120 &deg; C. Unfortunately, decomposition temperatures of
ILs-DMP depend on several factors, including the
heating rate, the type of atmosphere, and even the type
of an analytical vessel. Therefore, different decomposition
temperatures appear in the literature for the same ILDMP. The fourth commonly used analysis of ILs-DMP is
the determination of their viscosity. The measurements
are highly dependent on the presence of a molecular
liquid (other solvent) in ILs-DMP, which most often is
water. Viscosities of liquid ILs-DMP cover a wide range
on the viscosity scale and depend on the measuring
temperature. Viscosity is usually measured only for
materials intended for transfer with flow (in tubes, as
lubricants, etc.) <a href="#1">[1] </a><a href="#2">[2]</a> <a href="#9">[9]</a>.</p>
<p class="art-para"><b>Specific methods</b>
<p class="art-para">The titrimetric quantitative analysis of ILs-DMP can be
deemed the most important specific analytical method. ILsDMP
can be easily titrated with perchloric acid in the solution
of glacial acetic acid <a href="#13">[13]</a> <a href="#14">[14]</a>. The DMP anion (pKa 1.29 <a href="#15">[15]</a>) reacts with the strong acid, and the titrimetric analysis at the
same time allows confirming the purity of the prepared ILDMP. It is worth noting that the obtained titration curves are
of high quality, and this allows easy finding of the equivalence
point. The content of the basic substance usually is = 99.5% in
carefully synthesized ILs-DMP. The titrimetric analysis can be
considered as the most accurate quantitative way of
characterization of IL-DMP samples. UV-Vis spectroscopy is
also proposed for the same purpose, although it is less
popular <a href="#16">[16]</a>. The second popular and often used specific
method is 1
H NMR spectroscopy of ILs-DMP, including the
comparison of integral intensities of resonance signals. The
integral intensity of six protons of the DMP anion (doublet at
d 3.28 ppm) should correspond to the integral intensities of
protons in the cation of the same IL-DMP, for example, to the
integral intensities of two protons (C<sub>4</sub>-H and C<sub>5</sub>-H) in a
1,2,3-trisubstituted imidazolium cation.</p>
<p class="art-para">The mentioned comparison is particularly important in
the case when ILs-DMP are prepared by the alkylation of the
chloride ion with trimethyl phosphate (the second route of
preparation), as it confirms a complete transformation of the
chloride ion. Unfortunately, the analysis of <sup>1</sup>H NMR spectra
gives much more inaccurate information than the titrimetric
analysis. For some ILs-DMP, the polarity is measured using
solvatochromic dyes, most frequently Nile Red <a href="#17">[17]</a>. They are
not &#8220;superpolar&#8221; solvents regardless of their ionic structure, as their polarity is somewhere between methanol and
acetonitrile. There is very little available information about the
toxicity of ILs-DMP. The DMP anion makes the biggest
contribution to the total toxicity of ILs-DMP <a href="#18">[18]</a>. The
amphiphilic ILs-DMP also show a marked toxicity on biological
cells and liposomes <a href="#19">[19]</a>. A specific simple method has been
devised for evaluating the toxicity of mixtures of ILs-DMP
with other ILs, which is dependent on the mixture information
only <a href="#20">[20]</a>. The &#8220;green&#8221; nature of ILs-DMP is called into question
after measuring the phytotoxicity of 1-ethyl-3-
methylimidazolium DMP <a href="#21">[21]</a>. Densities of some ILs-DMP are
measured mainly for their application in dissolving biomass
<a href="#22">[22]</a>, as well as for understanding the effect of electrostatic
interactions on the density of ILs <a href="#23">[23]</a>. The physicochemical
properties of trialkylphosphonium cation-based ILs-DMP that
are less known to the public are described in detail in an
extensive research, particularly emphasizing their increased
thermal stability <a href="#24">[24]</a>.</p>
<p class="art-subhead">Application</p>
<p class="art-para">The excellent dissolution capacity is the most praised
property of ILs-DMP, and the light dissolution of cellulose is
the best example of it. The high dissolution ability is based on
the additional cooperation of the solute with both the cation
and the anion (DMP ion) of IL-DMP, in distinction from
molecular liquids (water or organic solvents), where such
cooperation is impossible. Furthermore, the DMP anion can
additionally show some complex-formation interaction with
the solute. All these forms of cooperation promote more
efficient dissolution of the solutes in ILs-DMP than in other
ILs, although the exact dissolution mechanism of ILs-DMP has
not been determined yet.</p>
<p class="art-para"><b>Investigations in petrochemistry</b></p>
<p class="art-para">To date, the use of ILs-DMP in petrochemistry has not
been sufficiently investigated, despite the distinct advantages
of these materials in comparison with other ILs. The main
achievements of applications of some well-known ILs in the
upstream oil industry have been collected and analyzed in an
excellent recent review <a href="#25">[25]</a>. Desulfurization of fuel oil <a href="#26">[26]</a>
and diesel oil <a href="#27">[27]</a> <a href="#28">[28]</a> using ILs-DMP should be noted as the
most successful application examples. The removal of
dimethyl disulfide via extraction using imidazolium-based
ILs-DMP has also been very successful, and various extraction
parameters have been recognized <a href="#29">[29]</a>. The aromaticity
indices and double-bond equivalents were studied to seek a
simpler approach in identifying the ILs-DMP suitable for the
desulphurization processes <a href="#30">[30]</a>. A total of 168 possible cation
and anion combinations in ILs, including ILs-DMP, were
screened with COSMO-RS (Conductor-like Screening Model
for Real Solvents) for the purpose of desulphurization of
diesel oil, and good agreement was reached between the
experimental and calculated data <a href="#28">[28]</a>. Asphaltene separation
with ILs-DMP was investigated for the deasphaltenes process
using a quantum chemical approach and COSMO-RS <a href="#31">[31]</a>. Separation of hydrocarbons (crude bitumen, heavy crude oil) from materials containing mineral solids has been highly
successful <a href="#32">[32]</a>. The activity coefficients were determined at
infinitive dilution of alkanes, alkenes, and alkyl benzenes in
ILs-DMP using gas-liquid chromatography <a href="#33">[33]</a>. ILs-DMP have turned out to be superior solvents for the headspace gas
chromatography of residual solvents with a very low vapor
pressure, the best of them being 1-(n-butyl)-3-
methylimidazolium DMP <a href="#34">[34]</a>. There is no doubt that ILs-DMP
will find a wide range of applications in all kinds of oil product
analyses in the near future.</p>
<p class="art-para"><b>Dissolution of biopolymers</b>
<p class="art-para">The largest number of studies on ILs-DMP are devoted to
the dissolution of biopolymers, mainly of cellulose, and these
investigation have been very successful <a href="#35">[35]</a> <a href="#36">[36]</a> <a href="#37">[37]</a>, including the dissolution of food processing byproducts, such
as corncobs <a href="#38">[38]</a>. Only a few ILs-DMP are capable to dissolve
cellulose efficiently, the best of them being 1-ethyl-3-
methylimidazolium diethyl phosphate <a href="#35">[35]</a>. The anions of ILs
capable to dissolve cellulose should be good hydrogen bond
acceptors, and DMP is such an anion. It has been established
that a cation also plays a significant role in the dissolution
process, the imidazolium cation being superior to others <a href="#36">[36]</a>. The ionic liquid-pretreated cellulose was transformed into the
water-soluble sugar completely <a href="#39">[39]</a> <a href="#40">[40]</a>. Many attempts have
been made to find out the precise mechanism of dissolution
<a href="#41">[41]</a> <a href="#42">[42]</a> <a href="#43">[43]</a>, thermodynamics of the dissolution processes
<a href="#44">[44]</a>, and the stability of cellulose during the dissolution
process <a href="#45">[45]</a>, as well as the viscosity of high-concentration
cellulose solutions in ILs-DMP <a href="#46">[46]</a>.</p>
<p class="art-para">Plant fibers were made from IL-DMP solutions, including
fibers from the regenerated plant fiber raw material <a href="#47">[47]</a>, purified cellulose fibers <a href="#48">[48]</a>, and even lignocellulosic materials
<a href="#49">[49]</a>. An efficient process for purifying cellulosic materials has
been developed <a href="#65">[65]</a>, which includes the separation and
removal of hemicellulose <a href="#50">[50]</a> <a href="#51">[51]</a>. Enhanced production of
sugars and lignin by means the fractionation of lignocellulosic
biomass in IL-DMP solutions has been proposed <a href="#52">[52]</a>. Recent
extensive solubility studies of different sugars in ILs-DMP <a href="#53">[53]</a>
have facilitated the biopolymer degradation research.</p>
<p class="art-para">Dissolution possibilities of other biopolymers in ILs-DMP
have been studied much less, except for the widespread
biopolymer chitin, which has been studied quite thoroughly
<a href="#54">[54]</a> <a href="#55">[55]</a>. It is worth mentioning that the addition of an aprotic
diluent (DMSO) has noticeably affected the dissolution
process <a href="#55">[55]</a>. The possibility of selective dissolution of xylan
&ndash; the most important type of hemicellulose &ndash; has also been
described <a href="#56">[56]</a>. The authors have also modified the DMP
anion by substituting one oxygen atom for sulfur and
selenium, respectively. This alteration has reduced the
hydrogen bond basicity of the ILs-DMP and has prevented
the dissolution of cellulose fibers, whereas the less ordered
xylan was still dissolved. The extraction of lignin from
lignocellulosic biomass was evaluated with the COSMO-RS
method, and the effect of cation and anion combination in
ILs-DMP was compared with that in other ILs <a href="#57">[57]</a>. Valuable
results have been obtained in the experiments of pretreatment
of lignocellulosic biomass with ILs-DMP, owing to
their ability to disrupt the extensive hydrogen-bonding
network. This has facilitated the subsequent enzymatic
hydrolysis and improved the sugar yield <a href="#58">[58]</a> <a href="#59">[59]</a>. Highly
successful dissolution of wool keratin in ILs-DMP was reported
recently, and fibers obtained from these solutions are used in
textile industry and medicine <a href="#60">[60]</a> <a href="#61">[61]</a>. 1-Butyl-3-
methylimidazolium DMP was recognized as the best solvent
for this purpose. It can completely dissolve 5.0 wt % wool
keratin at 120 &deg;C. Earlier, the protein stability in ILs-DMP was
determined using the differential scanning fluorimetry <a href="#62">[62]</a>. An efficient method for dissolving peanut meal in ILs-DMP
has also been proposed <a href="#63">[63]</a>, and several methods have been
developed for the preparation of peanut protein composite
fibers from these solutions <a href="#64">[64]</a> <a href="#65">[65]</a>. Next, the rheological
properties of concentrated gelatin solutions in some ILs-DMP
have been examined, and the existence of entanglement
coupling between gelatin chains in the solutions has been
discovered <a href="#66">[66]</a>. An interesting method has also been
proposed for the preparation of silkworm fiber material from
solutions in ILs-DMP <a href="#67">[67]</a>.</p>
<p class="art-para">Further modifications of biopolymers in IL-DMP media
have been successful. Esterified cellulose pulp compositions
are prepared from available wood pulp sources, and their
hemicellulose content is distinct from the cellulose esters
prepared by conventional esterification processes <a href="#68">[68]</a>. Carboxyl cellulose is prepared by grafting the cellulose
material with an acid anhydride in ILs-DMP <a href="#69">[69]</a>. A number of
succinic acid-based products have been obtained from
biomass with ILs-DMP and high-pressure carbon dioxide <a href="#70">[70]</a>. A method for the preparation of an enzyme cellulaseimmobilizing
carrier from the straw treated with ILs-DMP and
a modifier has been proposed. The method produces no
pollution, has mild operation conditions and a simple and
feasible treatment process, and the IL and modifier can be
completely recovered <a href="#71">[71]</a>. A method of silylation of lowmolecular-weight
carbohydrates (glucose, mannose and
lactose) in ILs has been developed for their gas
chromatographic analysis, and the derivatization reagents
and reaction conditions have been evaluated for different
carbohydrates <a href="#72">[72]</a>. Ball-milled lignocellulosic biomass was
dissolved and acetylated in ILs-DMP with or without a cosolvent
in order to find milder dissolution conditions and to
mitigate possible degradation processes <a href="#73">[73]</a>. Further, a
process of lignin oxidation in ILs-DMP coupled with the
separation for the production of high added-value aromatic
aldehydes has been proposed <a href="#74">[74]</a>. A method for the
preparation of sodium lignosulfonate from crop straw has
been demonstrated <a href="#75">[75]</a>. Another useful method relates to
the production of regenerated biopolymers in the form of
carbohydrates, such as cellulose, starch, et al., using a solvent
system that contains ILs-DMP and protic solvents <a href="#76">[76]</a>. A
highly useful experimental investigation about the pretreatment
of sugarcane bagasse with ILs-DMP to facilitate the
enzymatic production of bioethanol has been performed <a href="#77">[77]</a> (see, section 3.5 below).</p>
<p class="art-para"><b>Other separations</b></p>
<p class="art-para">Extractions and separations of other products from the
main product are less investigated in IL-DMP media. Screening
of various ILs for the extraction of pentachlorophenol and dichlorodiphenyltrichloroethane from aqueous solutions
using the COSMO-RS model for the prediction of the
selectivity of these compounds has been reported <a href="#78">[78]</a>. A
similar approach is used for the prediction of selective
extraction of all three cresols <a href="#79">[79]</a>. ILs-DMP have proved to be
superior extractants than traditional organic solvents for the
determination of negligible amounts of phenols <a href="#80">[80]</a>. ILsDMP
are even considered as novel partitioning media for
water purification devices <a href="#81">[81]</a>. A simple and green extraction
method has been proposed to recover vitamin E from the
deodorizer distillate with the help of ILs-DMP, and the
theoretical expectations successfully satisfy the experimental
results <a href="#82">[82]</a>. Recently, ILs-DMP were found to be highly
valuable as separation agents for terpenes and terpenoids
<a href="#83">[83]</a>. Even a high-value triterpenoid betulinic acid can be
easily extracted by ILs-DMP after streamlined oxidation of the
birch bark industrial byproduct <a href="#84">[84]</a>. A quite new application
area for ILs-DMP is in extracting polyester from the fabrics
that contain polyester and dyes. Unfortunately, no economic
considerations are presented in the patent <a href="#85">[85]</a>. Finally, the
recovery of thiophene from crude benzene by extraction with
ILs-DMP has been proposed <a href="#86">[86]</a>.</p>
<p class="art-para"><b>Synthetic transformations of organic substances</b></p>
<p class="art-para">Transformations of organic substances have been less
investigated in ILs-DMP than in other ILs. The excellent
dissolution capacity of ILs-DMP is usually availed of, since it is
considerably higher than that of traditional organic solvents, and sometimes their catalytic action appears in these
transformations.</p>
<p class="art-para">The displacement of poisonous chromium catalysts with
lanthanide catalysts in the process of the direct conversion of
glucose to 5-(hydroxymethyl)furfural has been successful in
ILs-DMP <a href="#87">[87]</a>. Notably, a higher reactivity was observed in
contrast to analogous chromium catalyst systems when the
hydrophobicity of the imidazolium cation in an IL-DMP was
increased. Further, a base-free conversion of the aromatic
aldehyde into 2,5-furandicarboxylic acid was also reported, and the possibility of using non-noble metal catalysts in these
oxidations was demonstrated <a href="#88">[88]</a>. The aerobic oxidation of
5-(hydroxymethyl)furfural over solid ruthenium hydroxide
catalysts in ILs-DMP at elevated temperatures and pressures
was also investigated. Unfortunately, both 2,5-furandicarboxylic
acid and 5-(hydroxymethyl)-2-furancarboxylic acid are
formed in these oxidation reactions <a href="#89">[89]</a>. Nevertheless, these
reactions serve well for the transformation of renewable
natural resources (straw, corn stems, etc.) into useful products
of fine organic synthesis. The production of glycerol carbonate
from glycerol over selected ammonium and imidazoliumbased
ILs-DMP was recently reported. The discovery helps
solving the problem of unintentional byproduct generation in
the biodiesel industry <a href="#90">[90]</a>. Another possibility was researched
to convert glycerol in IL-DMP media in its reaction with CO<sub>2</sub>
, and it turned out that the &#8220;protected glycerol&#8221; can serve as a
useful and cheap solvent <a href="#91">[91]</a>. Ionic liquids themselves
represent an alternative solvent system to absorb CO<sub>2</sub> from
emission sources, demonstrating distinct advantages over
traditional solvents (e.g., aminoethanol): high chemical
stability, low corrosion, nearly zero vapor pressure, etc. <a href="#92">[92]</a>
The use of high-stability Rh carbonylation catalysts in the
production of acetic acid from methanol in IL-DMP media in
rather harsh reaction conditions (at 170&ndash;230 &deg;C and 2.0&ndash;4.0
MPa) has been proposed <a href="#93">[93]</a>. Catalytic hydrogenation has
also been investigated in ILs-DMP over atomically dispersed
supported metal catalysts, and the results have demonstrated
a wide range of options for adjusting the catalytic properties
of the catalysts used <a href="#94">[94]</a>. The selective hydrogenation of
1,3-butadiene to cis- or trans-butene from the crude C4
steam cracker fraction represents a convincing example of a
selective reaction using a solid catalyst covered with a ionic
liquid layer (SCILL) <a href="#95">[95]</a>. The behavior of other catalysts &ndash; copper complexes of acetyl acetone in particular &ndash; in ILs-DMP
and organic solvents was investigated by the spectroscopic
and electrochemical techniques, and the redox behavior of
these complexes was described <a href="#96">[96]</a>. The interaction between
ILs-DMP and acetone was also studied, and acetone was
found to be a strong hydrogen bond acceptor in these media
<a href="#97">[97]</a>. Recently, the gold-catalyzed dimeric cyclization of
1-phenylpropenes into 2,3-dihydro-1H-indenes was
examined in ILs-DMP, and the main patterns of these
cyclizations were described <a href="#98">[98]</a>. Even catalyst compositions
for olefin metathesis in a gas phase were described for ILsDMP, and the manufacture of ethene and 1-butene from
propene was demonstrated <a href="#99">[99]</a>. Sometimes, ILs-DMP have
served as reaction media and catalysts at the same time. This
double manifestation has been demonstrated for some
Knoevenagel condensation reactions <a href="#10">[10]</a> <a href="#12">[12]</a> and even for
the syntheses of heterocyclic compounds, such as
1,4-dihydropyridine derivatives <a href="#100">[100]</a>. The syntheses of some
polymers in IL-DMP media have also been described: poly(caprolactone) with low polydispersity was prepared by
the controlled ring-opening polymerization of e-caprolactone
<a href="#101">[101]</a>; piperazine-based polyimides were prepared in ILs with
a higher degree of polymerization than in the conventional
polymerization processes <a href="#102">[102]</a>; poly(&beta;-alanine) was
successfully synthesized in the direct polyamidation reaction
of &beta;-alanine with triphenyl phosphite as the condensing
agent <a href="#103">[103]</a>; and hybrid-supported metallocene catalysts
were successfully tested for polyolefin syntheses using these
catalysts <a href="#104">[104]</a>.</p>
<p class="art-para"><b>Enzymatic transformations of organic substances</b></p>
<p class="art-para">Despite the well-known instability of enzymes, the
enzymatic reactions of organic compounds have been very
successfully induced in IL media, including ILs-DMP. The
possibility of preparation of isoamyl acetate was demonstrated
already 10 years ago using the immobilized enzyme Candida
antarctica lipase B and IL-alcohol biphasic system. The
recyclability of the IL-enzyme set has been studied extensively, and the system was found to be reusable 7 to 10 cycles <a href="#105">[105]</a>. Later on, the activity of several enzymes was studied in different
ILs, and the enzymes were found to be most active in ILs-DMP
<a href="#106">[106]</a>. Sometimes, chemically modified cations of ILs-DMP
improve the activity and stability of enzymes, for example, formate dehydrogenase in the [mmim][DMP] solution <a href="#107">[107]</a>
<a href="#108">[108]</a>. ILs-DMP have also served as biocompatible solubilizers
for hardly water-soluble substances, for example, in the
stereoselective reduction of ketones using the alcohol
dehydrogenase from Lactobacillus brevis <a href="#109">[109]</a>. Interesting and
promising are investigations in electroenzymatic syntheses, efforts to combine oxidoreductase-catalyzed reactions with
the electrochemical reactant supply <a href="#110">[110]</a>. However, the most
important is the enzymatic hydrolysis (saccharification) of
cellulose in ILs-DMP. Different cellulose-containing materials
have been hydrolyzed in ILs-DMP in this way: bagasse <a href="#111">[111]</a>, chestnut shells <a href="#112">[112]</a>, barley straw <a href="#113">[113]</a>, etc. Different methods
have been used for the separation of glucose from enzymatic
hydrolysis mixtures, mainly alumina column chromatography
<a href="#114">[114]</a>. A new approach to enzymatic reactions in IL-DMP media
is the use of purposefully made model enzymes, for example, the model cellulase from polybasic carboxylic acid, inorganic
acid and IL <a href="#115">[115]</a>, or polybasic carboxylic acid and organic base
<a href="#116">[116]</a>. It is too early to judge about the development prospects
for these approaches. Admittedly, enzymatic transformations
are less developed in ILs-DMP than in other ILs.</p>
<p class="art-para"><b>Use in electrochemistry</b></p>
<p class="art-para">The use of ILs-DMP in electrochemistry is also less
developed than in other ILs. The information about the
possibilities of such use can be found mainly in patent
literature. Printed energy storage devices <a href="#117">[117]</a> and printed
silver oxide batteries <a href="#118">[118]</a> are described in detail. Benefits of
ILs-DMP when used as electrolytes for photovoltic devices are
praised <a href="#119">[119]</a>. These materials are also useful in electric light controlling elements <a href="#120">[120]</a>. A great success is the application
of ILs-DMP in cyanide-free copper-zinc electroplating liquids, and several recipes have been proposed for non-cyanide
plating solutions <a href="#121">[121]</a> <a href="#122">[122]</a>. ILs-DMP have also served as
composite materials for the preparation of very specific
electrochromic devices <a href="#123">[123]</a>. There is also an innovative
method of preparation of a heteroatom in-situ doped carbonbased
catalyst for the fuel cell proposed, with flexible and
changeable doping species of heteroatoms and high doping
efficiency <a href="#124">[124]</a>.</p>
<p class="art-para"><b>Other applications</b></p>
<p class="art-para">Applications of ILs-DMP in other areas are still fragmentary. They have been used in high-temperature environmentfriendly
lubricant compositions <a href="#125">[125]</a>. They have helped to
change the interfacial behavior, such as wettability and
adhesion of surfaces, and the well-known possibility to design
the necessary structure of ILs has been highly useful in
developing the very best compositions for concrete surfaces
<a href="#126">[126]</a>. Absorption heat transformers using ILs-DMP together
with water or methanol as working fluids have been proposed, and these systems are superior in comparison with the previous
ones <a href="#127">[127]</a>. Phase diagram data have been obtained for
aqueous two-phase systems containing ILs-DMP and
potassium salts <a href="#128">[128]</a>. ILs-DMP have been used as entrainers in
the azeotropic systems of water/ethanol, water/2-propanol, and water/tetrahydrofuran <a href="#129">[129]</a>. Original information has
been obtained about the interactions that control the phase
behavior of aqueous biphasic systems composed of poly (ethylene glycol) polymers and ILs-DMP. The adjustable
structural features of ILs and the influence of the molecular
weight of the PEG polymer have been discussed <a href="#130">[130]</a>. Recently, the use of eutectic mixtures of ILs-DMP as absorbents in
absorption chillers was proposed <a href="#131">[131]</a>. The addition of ILsDMP
to polymer compositions has delayed crystallization and
lowered the crystallization point of thermoplastic polymers
<a href="#132">[132]</a>. ILs-DMP have helped in producing porous structures
from synthetic polymers (fibers, sheets, films, coatings, etc.) <a href="#133">[133]</a>. Liquid layers of ILs-DMP have alleviated the stress
generated between the substrate and the solid ultra-thin film, and the flexibility of films <a href="#134">[134]</a> and chemical-mechanical
properties of tribofilms have been studied in depth <a href="#135">[135]</a>. Recently, ILs-DMP have helped to accomplish a rather difficult
task: the fabrication of polyethersulfone flat sheet membranes. The obtained membrane morphologies were compared with
those of the membranes prepared from solutions in DMF and
were further successfully applied in DNA separations <a href="#136">[136]</a>.</p>
<p class="art-para">No matter how diverse the available information about
ILs-DMP is today, more is yet to come. There is no doubt that
there will be more pleasant surprises for researchers of these
materials in the near future.</p>
<p class="art-subhead">Conclusions</p>
<p class="art-para">ILs-DMP are readily available materials with chemical and
mechanical properties superior to most other ILs. Safe and
reliable methods have been developed for their qualitative and
quantitative analyses. Just the first attempts are made in using
these materials in oil chemistry. Their use is much better
explored in the dissolution of cellulose and related materials, although there is still no credible explanation for their increased
dissolution capacity. The dissolution of other biopolymers in
ILs-DMP has also been quite successfully developed, as well as
different transformations of biopolymers. Other areas of use
are represented only with some examples. Of course, future
developments in these areas are open. At the same time, the
influence of the structure of ILs-DMP on the processes
performed in their media has not been sufficiently appreciated
by now. The number of dialkyl phosphate anions is limited. This
makes it difficult to appreciate the true impact of the anion in
the examined processes. Investigations in these directions
might lead to a considerable selectivity increase of ILs-DMP in
different application processes.</p>
<p class="art-subhead">Acknowlwdgement</p>
<p class="art-para">The authors sincerely acknowledge the material and
financial support of the University of Latvia.</p>
<div style="clear:both">&nbsp;</div>
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