American Journal of Applied Science and Technology
13
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VOLUME
Vol.05 Issue 04 2025
PAGE NO.
13-19
10.37547/ajast/Volume05Issue04-03
Obtaining Effective Depressor Dispersant Additives for
Diesel Fuel Based on Pentaerythritol
Sirojiddinov I.L.
Tashkent Chemical Technology Research Institute, Uzbekistan
Vafoyev O.SH.
Tashkent Chemical Technology Research Institute, Uzbekistan
Nurqo‘lov F.N.
Tashkent Chemical Technology Research Institute, Uzbekistan
Received:
19 February 2025;
Accepted:
18 March 2025;
Published:
21 April 2025
Abstract:
In the development of a depressant additive for diesel fuels, unsaturated fatty acids with pentaerythritol,
the characteristics of which correspond to TU 38.401.1059-97, were selected as the main component. The choice
of pentaerythritol was due to the following reasons: firstly, unsaturated organic acids, which do not have a
permanent consumer, are inexpensive products produced in the country, which are formed in industrial production.
Keywords:
Diesel fuels, additive, depressant, component, pentaerythritol, oleic acid.
Introduction:
The quality of diesel fuel is closely related to the
reliability and durability of the engine. The use of low-
quality diesel fuel leads to poor performance of the
high-pressure fuel pump, rough engine operation,
increased carbon formation, reduced combustion
efficiency, increased smoke emission, etc. One of the
main disadvantages of diesel fuels is their
physicochemical properties, which makes it difficult to
start diesel engines in winter.
Pentaerythritol (PE) is a polyhydric alcohol containing 4
hydroxyl groups and a neopentane carbon skeleton. PE
is widely used in the petrochemical industry. For
example, fire-resistant heat-resistant compositions [1-
3], alkyd varnishes, paints and resins [4,5], chemically
resistant polymeric materials (pentaplast) [6], non-
ionic surfactants [7], antimicrobial agents [8],
stationary phases for chromatographic separation,
polyoxidation inhibitors, [9], [10] agents [11].
The industrial method of producing PE is the aldol
condensation of acetaldehyde with formaldehyde in an
alkaline medium, followed by recrystallization [12],
but, unfortunately, this process is associated with the
formation of by-products that have low market
demand and the high cost of removing them from
commercial PE, therefore, modern technologies are
constantly being developed [13-15].
Currently, the main producer of pentaerythritol in the
Russian Federation is the Metafrax company; according
to annual reports for 2018-2020. The stability of the PE
market, as well as the expansion of production
capacities, is noticeable. At the same time, there is a
large share (~60%) of commercial products exported to
foreign countries (Belgium, Germany, Italy, Korea, the
Netherlands, Poland, Estonia, Belarus). According to
the Ministry of Industry and Trade, the share of Russian
pentaerythritol in the EU market is 40%[16].
Of the various products based on pentaerythritol,
esters are of greatest interest. Among the wide range
of applications of such compounds, their use as
lubricants for special aviation equipment [17] and
plasticizing compositions [18] deserves special
attention.
There are a number of requirements for industrial
plasticizers arising from technical and economic points
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American Journal of Applied Science and Technology (ISSN: 2771-2745)
of view: low volatility, absence of odor and color,
chemical inertness, low cost, environmental safety, and
compatibility with the polymer material [19].
According to the requirements, mainly pentaerythritol
esters and linear or branched acids with an average
molecular weight of 400-800 g/mol are used as
plasticizers [20,21]. Currently, these compounds are
gradually replacing the traditionally used phthalate
plasticizers, the production of which cannot fully meet
the increasing environmental requirements [22, 23].
For example, in European countries and the USA, the
use of phthalate plasticizers such as DBP (benzylbutyl
phthalate) in children's products has been permanently
banned since 2005 [24].
Of great interest are esters of pentaerythritol and
branched acids, which, due to their isomeric structure
and high molecular weight, provide low diffusion, i.e.,
they have a higher resistance to emissions from the
polymer compared to plasticizers with a linear
structure [25].
The use of pentaerythritol esters as lubricants is closely
related to the development of aircraft gas turbine
engines. As aircraft designs become more complex, the
requirements for lubricating oils under extreme
operating conditions have also become more stringent,
such as thermal and thermal-oxidative stability,
compatibility with various additives, good lubricating
properties and viscosity index. From an environmental
point of view, ester oils are preferable, since base oils
produced from petroleum sources are not renewable
and difficult to biodegrade. According to statistics,
when disposed of or leaked, most lubricants (50-60%)
come into direct contact with soil, water and air, posing
a potential threat to the ecosystem [26]. Standard
mineral oil cannot fully meet these high performance
standards, so synthetic ester oils almost completely
dominate this market segment.
Mixed esters of pentaerythritol are used as lubricants,
for example, the composition of 36/1 K and 36/1Ku-A
oils is known, which contain products obtained by
esterification of PE with a mixture of C5-C9 synthetic
fatty acids, with the addition of paraoxyphenylamine
(antioxidant content) in the amount of 2% [27]. In
addition, sterically hindered esters are used as heat
carriers where fluidity is required at low temperatures,
as well as lubricants in metal rolling. The high quality of
the ester base has allowed foreign companies to
organize the production of synthetic oils, plastic
lubricants and hydraulic fluids for special equipment
with improved performance characteristics [27]. The
high technologies used in the creation of ester oils are
constantly being improved and modernized, and
therefore meet the requirements of environmental
safety, resource conservation and diversification of
areas of application. The low level of domestic
production of synthetic lubricants is primarily due to
the lack of synthetic raw materials, additives, and
advanced scientific and technical capacity [28,29].
The traditional method for obtaining esters is the
esterification reaction, which consists of the
interaction of an alcohol with a carboxylic acid or its
anhydride, catalyzed by Brønsted (HCl, H2SO4) or Lewis
(AlCl3, ZrCl4, etc.) acids [30].
It is known that the etherification reaction is reversible,
and when the process is carried out in the liquid phase,
it occurs with a small thermal effect, and in the gas
phase with an exothermic effect and high values of
equilibrium constants [31]. The production of
pentaerythritol esters has long been the focus of
attention, as evidenced by numerous publications
devoted to the products obtained by etherification of
various individual carboxylic acids and their mixtures
and transetherification of vegetable oils with
neopolyols.
METHODS
The synthesis of depressant compounds is carried out
by etherification. The reaction was carried out in three-
necked flasks equipped with a stirrer and a
thermometer. 10 g of pentaerythritol alcohol was
placed in the flask, and 30% of the 1% orthophosphoric
acid catalyst was dissolved in toluene solvent and 40 g
of oleic acid were added to it until it was dissolved,
based on the mass of pentaerythritol. The reaction
mixture in the flask was heated to 100-1100 °C at
atmospheric pressure for 4 hours with stirring. Then
the reaction mixture was cooled to room temperature
of 20-25 °C. After the reaction was completed, 8 g of
5% sodium hydroxide solution was used to neutralize
the unreacted oleic acid. During the neutralization
process, 5% sodium hydroxide solution was added to
the ether part of the mixture until litmus paper turned
blue. The resulting ester was separated from the lower
aqueous layer in a Buchner funnel and filtered through
porous filter paper. After filtration, the oleic acid ester
PEO was formed, and the reaction yield was 42.29 g
(84.58%).
As a result, it was found that complete conversion of
pentaerythritol was observed when the molar ratio of
alcohol to acid = 1: 4, therefore, this molar ratio was
used later. It was found that orthophosphoric acid
significantly accelerates the process compared to the
thermal option of process control, however, the use of
catalysis with inorganic acids helps to accelerate
undesirable negative osmolization reactions of the
reaction mixture, negatively affects the color of the
product, and also increases the complexity of the
subsequent stages of separation.
In all synthesis options, complete separation of the
water of reaction was observed. Carrying out the
synthesis at high temperatures (in the absence of a
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American Journal of Applied Science and Technology (ISSN: 2771-2745)
solvent) leads to a decrease in the yield of tetraesters,
which leads to the formation of by-products (which
worsen the color indicators - a necessary parameter
characterizing the quality), which are not completely
removed from the target product. A similar result was
observed when using homogeneous catalysts. At the
same time, the thermal etherification option in solvent
conditions shows the best results.
Thus, for further studies, the following parameters
were used: the amount of azeotrope-forming
substances toluene 30% of the reaction mass; catalyst
1%; pentaerythritol ratio: acid = 1: 4 (mol.); reaction
zone temperature 100-110 0C. After removing the
water released as a result of the azeotropic reaction
with the solvent, the remaining solvent was removed
by distillation at atmospheric pressure, and then excess
acid was removed under vacuum.
The introduction of the extractant into the crude
product was carried out by stirring for 2 hours (ratio 1-
1, 1-2) at 500C; no transesterification and hydrolysis
were observed. The resulting mixture was stored at -
300C for 10-12 hours. After the formation of two
phases, the etherification product was separated from
the extractor by decantation. The extractor residues
were removed by vacuum drying for 2-3 hours. When
regenerating the extractor, it was possible to reduce
the loss of the target product to 5-7%.
The recrystallization method was used to purify the
crystalline products. Methanol was used in 5 to 15 (wt.)
relative to the extracted product. Except for
pentaerythritol tetraolein, acetonitrile was used in 4-5
times
excess
(wt.)
for
its
extraction.
The
recrystallization temperature was -300C, the time for
tetraolein was 1.5 hours, for the rest 10-12 hours.
The implemented methods of separation and
purification turned out to be very effective, and due to
the high quality of the target product, the thermal
etherification option in the presence of a solvent is
preferred.
Low-temperature properties are characterized by the
cloud point, the filtration limit temperature and the
freezing point. The cloud point is the temperature at
which the phase composition of the fuel changes, since
a solid phase appears along with the liquid phase. In
this case, the fuel loses its transparency and becomes
cloudy due to the release of microscopic ice crystals (if
there is water in the fuel) and mainly solid
hydrocarbons. However, when cloudy, the fluidity of
the fuel does not change. The size of the crystals is such
that they pass through the filters. At the maximum
filtration temperature, the crystal size of the solid
hydrocarbons increases and they do not pass through
the filters, i.e. the fluidity of the fuel deteriorates. At
the crystallization point, the crystal lattice hardens so
much that the fuel loses its fluidity.
First trial
: During cooling, the sample is continuously
stirred with a stirrer for 20 s and rested for 15 s. When
the thermometer shows a temperature close to the
expected cloud point, the test tube is removed from
the cryostat and compared to the standard sample to
observe the turbidity. If the fuel is not cloudy compared
to the transparent standard, the test tube is lowered
back into the cryostat. With each subsequent decrease
in the temperature of the sample by 1 0С, it is taken for
comparison with the standard. When a visible turbidity
appears in the sample that does not disappear with
stirring, the temperature is recorded. The temperature
at which the appearance of turbidity in the tested fuel
is observed is taken as the cloud point of this fuel
sample. This method determines the cloud point of
diesel fuels without additives and tests with the
addition of various amounts of additives.
Second trial
: Constant stirring is maintained at the
same interval with a difference of 15-170C between the
sample and the coolant residue. 50C before the
expected freezing temperature, the sample is removed
from the cryostat and tilted at an angle of 45° for 1
minute. If the sample is mobile, it is lowered back into
the cryostat, then every 10C the sample temperature is
lowered and tilted at an angle of 45°. When the sample
is completely stationary at an angle of 45° for one
minute, the operation is stopped and the temperature
is recorded as the freezing point of the sample.
Filtration limit temperature (on a cold filter) - the
highest temperature at which a certain volume of fuel
does not flow from a standard filter unit for a certain
time during cooling under standardized conditions.
Third trial
: The measuring vessel is filled to the marked
mark with the sample and an insulating ring is placed
on the bottom of the sleeve. The vessel is closed with a
suitable stopper with a filter pipette and a
thermometer. After installation in the apparatus, the
lower part of the filter is placed at the bottom of the
measuring vessel, parallel to the thermometer pipette
and 1.5-2 mm above the bottom of the vessel. The div
is placed vertically in a cooling bath 85 mm deep, in
which the temperature is maintained at -34 °C. A
vacuum device is connected to the pipette using
flexible hoses connected to a tap, then a vacuum is
applied and the air flow is adjusted. Given that the
cloud point of the samples under study is known, the
determination begins when the sample is cooled to 5
°C above the cloud point. After setting the required
temperature, it is necessary to turn on the valve to
connect the filter to the vacuum, which simultaneously
turns on the stopwatch and causes the sample to be
sucked into the pipette through the filtration mesh.
After the fuel reaches the mark on the pipette, the tap
is returned to its original position, so that the sample is
poured into the measuring vessel and the stopwatch is
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American Journal of Applied Science and Technology (ISSN: 2771-2745)
stopped. If the fuel consumption time does not exceed
60 seconds, the temperature is further reduced in 1°C
increments. The temperature at which the sample
stops flowing through the filter or the pipette does not
reach the mark within 60 seconds is considered the
maximum filtration temperature for that sample.
RESULTS
Taking into account the analysis of the literature data,
it should be noted that homogeneous and
heterogeneous
catalysts
(sulfuric
acid,
orthophosphoric acid, sulfonic cation exchangers, etc.)
are widely used, but, unfortunately, the use of catalysts
negatively affects the purity of the product, as a result
of which it becomes difficult to obtain the desired
tetrasubstituted pentaerythritol esters, which worsen
the properties (color, viscosity, etc.). Thus, to avoid the
above, we used the option of thermal etherification of
pentaerythritol (self-catalysis).
The dynamics of changes in the cloud point, freezing
point and filter limit temperatures are presented in
Figures 1-3.
The dependence of the degree of change in the low-
temperature properties of diesel fuels on the amount
of added additives and the relationship between the
hydrocarbon composition of the fuel and the efficiency
of adding this additive are shown.
The dependence of the cloud point on the amount of
additives added is shown in Figure 1.
Figure 1. CHANGE IN FREEZING TEMPERATURE BY ADDING
DEPRESSOR ADDITIVES TO ECO DIESEL FUEL
PEO - limit temperature of clouding ability of the
sample;
PES - limit temperature of clouding ability of the
sample;
DZ - limit temperature of clouding ability of the sample.
The dynamics of changes in the freezing and filtration
limit temperatures are presented in Figures 2-3. The
dependence of the degree of change in the low-
temperature properties of diesel fuels on the amount
of added additives and the relationship between the
hydrocarbon composition of the fuel and the efficiency
of adding this additive are shown. The dependence of
the freezing point on the amount of added additives is
shown in Figure 2.
Figure 2. CHANGE IN CLOUD POINT BY ADDING DEPRESSOR
ADDITIVES TO ECO DIESEL FUEL
-30
-25
-20
-15
-10
-5
0
0%
0,01%
0,15%
0,03%
0,05%
Т
em
pera
tur
e
0
C
T(z)
Concentration (%)
DZ (0)
PES-1
PEO-1
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American Journal of Applied Science and Technology (ISSN: 2771-2745)
PEO - freezing point of the sample;
PES - freezing point of the sample;
DZ - freezing point of the sample.
Analyzing the obtained data, we can say that the
depressant additive had the greatest effect on reducing
the freezing point in samples 1 and 2. The freezing
point of the PEO sample decreased from -9°C to -27°C.
The greatest modification effect was achieved with an
additive amount of 0.50% of the fuel volume. The
freezing point of the PES sample decreased from -9°C
to -25°C, which indicates the best compatibility of
diesel fuel with the additive we have chosen. According
to the modified low-temperature performance, PEO
diesel fuel can be transferred from the category of
summer grades of diesel fuel (freezing point -25°C) to
the winter category (-27°C in temperate climates). The
highest improvement in the freezing point was
achieved with 0.5% of the additive added to the
sample.
For sample DZ, this additive had no apparent effect on
the freezing point shift.
The dependence of the maximum filtration
temperature on the concentration of added depressant
is given below.
Figure 3. CHANGE IN FILTERING TEMPERATURE BY ADDING DEPRESSOR
ADDITIVES TO ECO DIESEL FUEL
PEO - the limit temperature of the filterability of the
sample;
PES - the limit temperature of the filterability of the
sample;
DZ - the limit temperature of the filterability of the
sample.
Analyzing the obtained data, we can say that the
depressor additive had the greatest effect on reducing
the maximum filterability temperature in PEO -
samples. The filterability limit temperature for the PEO
sample decreased from -5°C to -9°C. The greatest
modification effect was achieved with an additive
amount of 0.5% of the fuel volume.
Based on the obtained data, it was concluded that the
addition of the additive reduces the cloud point,
freezing point and filterability limit temperature for
-14
-12
-10
-8
-6
-4
-2
0
0%
0,01%
0,15%
0,03%
0,05%
Т
em
peratur
e
0
C
T(p)
Concentration (%)
DZ
PES-1
PEO-1
-10
-9
-8
-7
-6
-5
-4
-3
-2
-1
0
0%
0,01%
0,15%
0,03%
0,05%
Т
em
pera
tur
e
0
C
T(f)
Concentration (%)
DZ
PES-1
PEO-1
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American Journal of Applied Science and Technology (ISSN: 2771-2745)
both PEO and PES - samples. However, the PEO -
sample showed the greatest sensitivity to the
modification of low-temperature properties by the
additive we selected. The freezing point decreased by
56.6%, the maximum filterability temperature
decreased by 78%. It gives the highest rates of
improvement of low-temperature properties for these
samples.
Based on the data from the original PEO, PSO sample,
after adding 0.2% mass, a decrease in low-temperature
properties was observed with a certain amount of
additives. It should be noted that the cloud point did
not change significantly, as did the crystallization point
and the final filterability. The optimal additive
concentration to achieve the greatest effect of
improving low-temperature properties was 0.5% of the
diesel fuel sample. In conclusion, it can be said that the
PEO depressant additive had the greatest effect on
reducing the cloud point, freezing point and filter limit
temperature of the diesel fuel sample.
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