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Solvent Extraction Group 10.06.2020 (Kurtarılan)
Solvent Extraction Group 10.06.2020 (Kurtarılan)
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ـ
Student
Alaa Jaafar Kadhim
Supervised by
Mr. Habib A. Hassan
Project of Bachelor’s
Kirkuk, 2020
CHAPTER ONE: THEORETICAL CONTENT
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1.1 Introduction 2
1.2 Gasoline 2
1.2.1 Definition 2
1.4.1 HYDRODESULFURIZATION 7
1.4.3 BIODESULFURIZATION 7
I
CHAPTER TWO: EXPERIMENTAL SECTION
CONTENT
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REFERENCE 32
II
LIST OF FIGURE
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Figures Pages
III
LIST OF TABLE
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Tables Pages
IV
LIST OF SYMBOLS
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symbol Names
H2S Hydrogen Sulfide
SO2 sulfur dioxide
SO4 Sulfate
HDS Hydrodesulphurization
ODS Oxidative desulfurization
SCW Supercritical Water
Aaq Water
Aorg organic liquid
NaOH Sodium hydroxide
AgNO3 Silver nitrate
S Pure sulfur
Na2S H2S
NaSR RSH
N Normality
V Volume
W Weight
Sp.gr specific gravity
M.wt molecular weight
Density
Dr.test Doctor test
T.S Total sulfur
NIL Zero
RSH Mercaptans
VI
ACKNOWLEDGMENT
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First and foremost, I am grateful to the God for the good health and wellbeing
that were necessary to complete this thesis.
I also place on record, my sense of gratitude to one and all, who directly or
indirectly, have let their hand in this venture.
VI
ABSTRACT
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In order to obtain the ultra-low sulfur fuels, deep desulfurization of fuels has become a
vital subject of environmental studies. Extraction desulfurization system is one of the
most promising desulfurization processes. The aim of this study is to investigate the
possible use of Ionic liquids as an extractant for the removal of sulfur components.
VII
C h a p t e r 1
General Introduction
1.1 INTRODUCTION
Fuel combustion cause pollution to the environment due to the sulfur compounds in fuel oils, which
forms SOX during combustion (Aydına, 2017). In recent years, considerable attention has been paid to
deep desulfurization of fuels. In the petroleum industry, hydrodesulfurization as a traditional method is
used to remove various sulfur compounds from fuels. The hydrodesulfurization efficiency is limited to
remove sulfur compounds such as thiols, sulfides, and disulfides in fuels. This method cannot be used
for hard-to-remove aromatic sulfur compounds such as dibenzothiophene, benzothiophene (BT),
thiophene (T) (Olawumi O. Sadare F. O., 2017), and their derivatives in fuels. Therefore, it is necessary
to develop other desulfurization processes based on adsorption, oxidation. Among these methods,
extractive desulfurization (EDS) using inorganic solvents were used for the removal of sulfur
compounds from the fuels. Ionic liquids are mixtures of salts and water. Recently, these compounds
were found to be effective in the EDS from models of gasoline (N. Farzin Nejad a b, 2012.).
Natural gas is typically separated into a gaseous fraction and a liquid fraction using a separator
vessel. The gaseous fraction leaving the separator, which may contain the impurities such as
mercury, carbon dioxide and hydrogen sulfide, is sent to a gas treatment and the liquid fraction
called ‗‗gas condensate‘‘ which contains sulfur contents, is fed into a reactor containing a
catalyst along with a stream of hydrogen gas. The product leaving the reactor contains a mixture
of hydrogen, hydrogen sulfide, and natural gas condensate having a reduced amount of sulfur
(Javad Ahmadpour, 2018).
1.2 Gasoline
1.2.1 Definition
Gasoline, also called gas (United States and Canada), or petrol (Great Britain) or benzene (Europe) is a
mixture of volatile, flammable liquid hydrocarbons derived from petroleum and used as fuel for internal
combustion engines. It is also used as a solvent for oils and fats. Originally a by-product of the
petroleum industry (kerosene being the principal product), gasoline became the preferred automobile
fuel because of its high energy of combustion and capacity to mix readily with air in a carburetor.
Gasoline is a mixture of hydrocarbons that usually boil below 180 oC (355 oF or, at most, below 200oC
(390 oF) (El-Naggar, 2014). The hydrocarbon constituents in this boiling range are those that have 4 to
12 carbon atoms in their molecular structure and fall in to three general types: paraffins (including the
2
cyclo paraffins and branched materials), olefins, and aromatics. Gasoline is still in great demand as a
major product from petroleum. The network of interstate high ways that links towns and cities in the
United States are dotted with frequent service centers where motorists can obtain refreshment not only
for themselves but also for their vehicles (Bellis, 2012).
From crude oil in the distillation column under atmosphere pressure each component of petroleum will
production one-by-one, gasoline and other petroleum products from crude oil and other liquids produced
in petroleum refineries (Angela O. Mamudu, 2019), though this might take many repetitive distillation
operations as fig(1.1). However, to do so would be both very wasteful and prohibitively expensive. On
the other hand, 20% of a good crude oil might yield gasoline on simple distillation Making 1,000,000
gallons of gasoline would require only 119,000 barrels of crude oil. The major chemical components of
straight-run gasoline are straight-chain paraffin in the range of pentane to nonane (Energy, 1991/1992)
3
From Condensate wells produce free natural gas along with a semi-liquid hydrocarbon condensate.
Whatever the source of the natural gas, once separated from crude oil (if present), it commonly exists in
mixtures with other hydrocarbons, principally ethane, propane, butane, and pentanes (Devold, OIL AND
GAS PRODUCTION HANDBOOK, 2006). While the ethane, propane, butane, and pentanes must be
removed from natural gas, this does not mean that they are all waste products. In fact, associated
hydrocarbons, known as natural gas liquids (NGL), can be very valuable byproducts of natural gas
processing. NGLs include ethane, propane, butane, iso-butane, and natural gasoline as fig (1.2). These
are sold separately and have a variety of different uses such as raw materials for oil refineries or
petrochemical plants (Devold, Oil and gas production handbook, 2013)
temperature, which causes not only corrosion of car engines but also serious harm to the environment
and human health (ZHANG Cun, 2011).Concentration levels of H2S vary significantly depending upon
their source. H2S produced from absorption processes, such as amine treating of natural gas or refinery
gas, can contain 50-75% H2S by volume or higher. Many other processes can produce H2S with only
ppm concentration (GROUP, 1998) .
4
The main environmental concerns related to sulfur emissions are acid rain and the formation of
particulate matter. When sulfur dioxide (SO2) is emitted and combines with water it forms sulfuric acid,
or acid rain. Acid rain has many negative environmental impacts including the acidification of aquatic
systems, increasing soil acidity and damage to vegetation. Acid rain can also cause the degradation of
buildings and other human infrastructure. Sulfur is also emitted from vehicles in the form of sulfate
particles (SO4) (Full, 2000 ). Along with nitrogen oxides (NOx), these particles contribute to particulate
matter (PM) formation. Airborne lead is highly toxic and can impact human development and the
nervous system. Sulfur is emitted as sulfur dioxide (SO2) and sulfate particulate matter—pollutants
which damage human health, impair visibility, and lead to the acidification of ecosystems (X.Pan,
2011).Sulfur compounds are responsible for major damage to materials. Sulfur oxides generally
accelerate metal corrosion by first forming sulfuric acid either in the atmosphere or on the metal surface.
Sulfur dioxide is the most detrimental pollutant with regard to metal corrosion [28]. Temperature and
relative humidity also significantly influence the rate of corrosion (Miller, 2005).
The acid rain as a result of this emission dissolves the calcium carbonate in monuments and
buildings that are made with limestone and marble. Sulfuric acid can cause huge economic losses owing
to the occurrence of metal corrosion in machineries and vehicles in oil plants (Olawumi O. Sadare F. O.,
2017).
Hydrogen sulfide is especially dangerous when it occurs in low-lying areas or confined workspaces
or when it exists in high concentrations under 1 pressure (Roth, 2004). As a result, work practices, such
as continuous monitoring and the use of specified respiratory protective equipment in certain work
situations, are of great importance.it is either the gaseous or liquid forms of the compound. Synonyms
for hydrogen sulfide include Hydrosulfuric acid, sulfurated hydrogen, sulfur hydride, rotten-egg gas, and
stink damp (Joh n F. Finklea, 1977).
Human health effects of exposure to Hydrogen Sulfide, an irritant and an asphyxiant, depends
on the concentration of the gas and the length of exposure. Background ambient levels of H2S
in urban areas range from 0.11 to 0.33 ppb, while in undeveloped areas concentrations can be
as low as 0.02 to 0.07 ppb. A rotten egg odor characterizes H 2 S at low concentrations, and
some people can detect the gas by its odor at concentrations as low as 0.5 ppb. About half of
the population can smell H2S at concentrations as low as 8 ppb, and more than 90% can smell
it at levels of 50 ppb. Hydrogen Sulfide, however, is odorless at concentrations
above 150 ppb, because it quickly impairs the olfactory senses (Rao, 2014). Some of the Health
effects of H2S on human are given in the table(1.1)
5
Table1.1: Health Effects of H2S (Somasekhara, 2014).
The presence of sulfur-containing compounds in fossil fuels leads to corrosion problems and
inactivation of the pollution control catalysts in internal combustion engines. Furthermore, sulfur oxides
(SOx), produced during the combustion of untreated fossil fuels, are the main source of acid
rain and air pollution. Due to these environmental concerns, very stringent standards on the sulfur
content of transportation fuels have been legislated in different countries. Therefore, different methods
for removal of the sulfur-containing compounds from fuels have been studied by many researchers
(Mohammad Dana, 2019).
6
1.4.1 HYDRODESULFURIZATION
HDS is a catalytic chemical process widely used to remove sulfur (S) from natural gas and from refined
petroleum products such as gasoline or petrol, jet fuel, kerosene, diesel fuel, and fuel oils. The purpose
of removing the sulfur is to reduce the sulfur dioxide (SO2) emissions that result from various
combustion practices (Bose, 2015). Hydrogenation of the sulfur compounds results in the formation of
undesirable, toxic gaseous hydrogen sulfide. The industrial hydrodesulfurization processes include
facilities for the capture and removal of the hydrogen sulfide gas (Thanh Tung NGUYEN, 2017).
In petroleum refineries, the hydrogen sulfide gas is then subsequently converted into by product
elemental sulfur. In fact, the vast majority of the 68,000,000 metric tons of sulfur produced worldwide in
2010 was byproduct sulfur from petroleum refining and natural gas processing plants. It requires either
severe process conditions such as temperature, pressure and space velocity or the use of novel effective
catalysts that able to convert the less reactive-non-desirable compounds at an acceptable rate (Amin,
2011)
ODS process is remarkably successful in the removal of sulfur under mild reaction conditions
(Muhammad Nobi Hossain, 2019). Which the sulfur compounds can be oxidized into their
corresponding sulfoxides and sulfones (Dan Xu, 2009). Appears to be particularly promising and is
currently receiving increasing attention because it avoids the use of hydrogen and allows the process to
be conducted at ambient conditions. Although this process is effective, there are still some problems
such as cross-contamination between extractant and fuel and loss of fuel. ILs have been examined for
effective removal of S-containing aromatic compounds, and these liquids are easy to handle because of
nonvolatility, nonflammability, and high thermal stability (ZHAO Di-shun, 2009).
1.4.3 BIODESULFURIZATION
Biodesulfurization is described as the process by which the use of a catalyst of biological nature enables
the removal of sulfur content in oil fractions at moderate pressure and temperature conditions. Given its
specificity, it is presented as a promising alternative for the removal of organic-sulfured molecules
resistant to conventional technologies, such as dibenzothiophenes and their substituted forms (Julia
Acero, 2003). It‘s involving the use of specific microorganisms to the removal of sulfur present in the
7
carbon chain, using the oxidation pathway ―4S‖, in which there is cleavage of carbon–sulfur bond, and
maintaining the calorific value of the organic molecule. The BDS is a low-cost technique when
compared with HDS. For this process to occur, activation of specific enzymes is needed (Santos, 2014).
Is typically per-formed in wet scrubbers, where the absorption mean is a water slurry containing fine
particles of limestone (or other alkaline absorbent species). In this way, So x absorption rate is enhanced
by reaction with dis-solved particles, which provide a continuous alkaline reagent supply. However, it
has been suggested that in areas close to the sea seawater scrubbing is an economically attractive
solution rather than a slurry, where scrubbing performance relies on seawater natural alkalinity. The
advantages of using seawater involve simple plant design, no addition of chemicals and no solid by-
products. The acidified effluent can be discharged directly into the sea, after a further neutralization step
obtained by mixing with fresh sea-water and additional forced oxidation of sulfite ions by air blowing
(Giuseppe Caiazzo, 2011).
(SCW) desulfurization was investigated for both model sulfur compounds and Arab Heavy crude. In
part 1, the reactions of alkyl sulfides in SCW were studied. During hexyl sulfide decomposition in SCW,
pentane and CO+CO2 were detected in addition to the expected six-carbon products (Kida, 2014). A
multi-step reaction sequence for hexyl sulfide reacting with SCW is proposed which explains the
surprising products. Intermediate studies were performed to confirm that the key intermediate hexanal
forms and rapidly decomposes to pentane and CO (Pushkaraj R. Patwardhan, 2013). In part 2, Arab
Heavy crude was treated with SCW and analyzed with comprehensive gas chromatography (GCxGC)
coupled with two detectors, sulfur chemiluminescence detector (SCD) and a flame ionization detector
(FID). SCD is a sulfur specific detector that allowed detailed analysis of the reactions that occur during
SCW treatment of real fuel mixtures (Demirbas, 2016).
Liquid-liquid extraction has been applied industrially for many years for the production of lubricating
oils, pharmaceutical preparation, natural product isolation, etc. Liquid ion exchange, however, was not
developed until the middle fifties when it was rapidly applied in the recovery of uranium from low-grade
ore. Its use in copper production only started two years ago and large-scale use only in the last five (Dr.
D.S. Flett, SEPTEMBER 9th - 16th 1977).
8
Solvent extraction techniques have a broad field of applications in inorganic and organic chemistry
and large-scale industrial separations, in analytical chemistry, in pharmaceutical and biochemical
industries, and in waste treatment. In addition, solvent extraction is a good instrument for studying
fundamental understanding of equilibrium and kinetics of complex formation processes. Extraction
methods have now become a routine procedure in separation technologies (El-Nadi, 2017).
In analytical chemistry, solvent extraction has come to the forefront in recent years as a popular
separation technique because of its elegance, simplicity, speed and applicability to both tracer and macro
amounts of metal ions. The aspects and basic principles of solvent extraction are very well explained. In
analytical chemistry, solvent extraction has come to the forefront in recent years as a popular separation
technique because of its elegance, simplicity, speed and applicability to both tracer and macro amounts
of metal ions. The aspects and basic principles of solvent extraction are very well explained (Fifield F.
W., 1975).
Treating of petroleum products by washing with solutions of alkali (caustic or lye) is almost as old as the
petroleum industry itself. Early discoveries that product odor and color could be improved by removing
organic acids (naphthenic acids and phenols) and sulfur compounds (mercaptans and hydrogen sulfide)
led to the development of caustic washing (Speight, 1978).
Solvent extraction refers to the process of selectively removing a solute from a liquid mixture with a
solvent. As a separation technique, it is a partitioning process based on the unequal distribution of the
solute (A) between two immiscible solvents, usually water (aq) and an organic liquid (org):
Aa Aorg
NaOH is extensively used in a variety of sweetening processes like caustic treatment, Merox process,
chelate sweetening, inhibitor sweetening etc. which shows that NaOH has greater affinity for the sulfur
compounds in the petroleum fractions. This is probably due to the acidic character of the certain sulfur
compounds like mercaptans, which readily distributes from the oil phase in to the alkaline layer of
NaOH and converts to sulphides (MOHAMMAD SHAKIRULLAH, 2010).
The process consists of mixing a water solution of lye (sodium hydroxide or caustic soda) with a
petroleum fraction. The treatment is carried out as soon as possible after the petroleum fraction is
distilled, as contact with air forms free sulfur, which is very corrosive and difficult to remove. The lye
reacts with any hydrogen sulfide present to form sodium sulfide, which is soluble in water.
9
1.4.5.2 ADVANTAGE OF EXTRACTION BY CAUSTIC TREATMENT (FDA,
2004)
Lends itself to rapid and very selective separations that are usually highly efficient.
Partition coefficients are often approximately independent of concentration down to tracer levels and,
therefore, can be applied to a wide range of concentrations.
Can usually be followed by back-extraction into aqueous solvents or, in some cases, the solution can be
used directly in subsequent procedures. This also provides significant preanalysis concentration of the
analyte.
Wide scope of applications the composition of the organic phase and the nature of complexing or
binding agents can be varied so that the number of practical combinations is virtually unlimited.
Can be performed with simple equipment, but can also be automated.
10
The main objective of this project is to study the desulfurization of fuels by using
liquid ــliquid extraction. In particular, petroleum product is going to be tasted, during
desulfurization of gasoline
• Being a part of reducing atmospheric pollution and derived effects such as acid rain.
11
C h a p t e r 2
Experimental Section
12
This chapter contains a description of the apparatus, chemical substance, and analysis measurement
method of sulfur, which were used in the test of experiment work.
The experimental work was performed in preparing the chemical and testing sulfur content in the
gasoline model.
1- Doctor test this is a qualitative test for the presence of hydrogen sulfide, or mercaptans in the
absence of hydrogen sulfide, in gasoline, jet fuel, kerosene and similar petroleum products.
ASTM Test Method D 4952, Qualitative Analysis for Active Sulfur Species in Fuels and
Solvents (Doctor Test)
2- Auto titration for the determination of sulfur compounds as hydrogen sulfide and mercaptan
sulfur in liquid hydrocarbons and oils.
3- Total sulfur are measured with an elemental combustion analyzer according to UV-
Fluorescence detection technique or Microcoulometric detection technique. These measurements
are carried out mainly in the Oil & Gas Industry. Petroleum products like gasoline.
1- Cylinder
2- Dark volumetric flask
3- Beaker
4- The balance of chemical
5- Auto titration device
6- Total sulfur device
2.2 THE MATERIALS THAT USED ARE:-
1- Gasoline
2- NaOH
3- AgNO3
4- Pure sulfur S
5- Distilled water
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2.3 SAMPLES OF GASOLINE
The gasoline sample was taken from North Gas Company (N.G.C) in Kirkuk. It was consist as shown in
table (2.1)
COMPONENTS PERCENTAGE %
C3 WT% ـــــــــــ
IC4 WT% ـــــــــــ
NC4 WT% 0.23
IC5 WT% 30.23
NC5 WT% 30.14
C6 WT% 39.40
The ionic liquid NaOH was prepared (0.1N, 100 g, and 98%) was dissolved in water (1000 mL).
The feed of gasoline treatment section is the residue product depropanizer unit. Gasoline desulfurization
unit performs on four main processes to remove sulfur compounds from gasoline and prepare it for the
end user., the first process, the pre-alkalization, removes hydrogen sulfide, carbon dioxide and a
small portion of carbonyl sulfide from the propane stream using an alkaline solution by the following
reactions:
From the top of the pre-alkalization vessel, the feed of the second process, Extraction, enters
the bottom of an extraction column, after being heated through a heat exchanger. Mercaptans and
14
Carbonyl Sulfide are removed from the Propane Stream in presence of an aqueous caustic solution
and a small amount of catalyst, according to the following reactions:
The caustic solutions are from caustic solution regeneration stage and Tanks improvised in
the Plant for storing materials. Water washing Stage, performed by bubbling the Propane streams
through the Water, to remove caustic traces from the bulk of Propane. Finally, the Water droplets are
adsorbed by a salt filter and flows to the Propane Treatment section.
The sample is shaken with a sodium plumbite solution in a test tube. If hydrogen sulfide is present the
following reaction occurs:
The lead sulfide is black and readily visible. If this reaction does not appear, sulfur is added to the
test tube and the mixture shaken again. If mercaptans are present, on shaking they undergo a series of
reactions, coloring the hydrocarbon layer first orange, then red and brown, and finally a black precipitate
of lead sulfide appears as shown in fig (2.1) . The overall reaction may be written:
15
Fig (2.1) Dr.Test
Dissolve 8.495 gm of AgNO3 in 500 ml of distilled water, it kept in dark volumetric flask because
AgNO3 affected by light.
16
Fig (2.2):- Auto titration device
NaSR = RSH
(TS) Stands for the sum parameter of all organic and inorganic sulfur compounds. Trace levels (0.02
– 10.000 mg/kg or ppm by weight) of Total Sulfur are measured with an elemental combustion analyzer
according to UV-Fluorescence detection technique or Microcoulometric detection technique. These
measurements are carried out mainly in the Oil & Gas Industry.
DESCRIPTION
18
2.3.3.1 MEASUREMENT OF SULFUR IN GASOLINE
A stream of inert gas (argon or helium) carries the reaction products after the produced water vapor is
removed into a reaction chamber. In this chamber, the SO2 molecules are converted to
excite through the absorption of energy of a UV lamp and emitting light (fluorescence) while it
settles into a stable state.
To calculate the area, the response signal is integrated. The linear regression function of the
concentration of standard mixtures versus integrated area can be used to calculate the sulfur
concentration of an unidentified product.
19
Fig (2.4) total sulfur chart
2.6.3.2 CALIBRATION
Calibration curves are generated using tert-Butyl-di-Sulfide in o-Xylene standards. Each of the
calibration solutions and blanks (o-Xylene) are measured three times. The average response of the blank
injections is subtracted from each calibration standard response conform method. Although the
ElemeNtS system is linear in response, ranging from 0 – 1000 ng/µL (figure 6), separate calibration
curves have been produced according to the proposed ranges in ASTM D5453 (Figures 2.6, 2.7, 2.8).
20
Table (2.2) Response values
Fig (2.5) Full range Calibration curve covering typical range of ASTM D5453
21
Fig (2.6) Curve I (0.5-10 ng/µL)
22
Fig (2.8) Curve III (100-1000 ng/µL)
23
2.6.3.3. FIND THE CONCENTRATION OF THE STANDARD SOLUTION
To find the concentrations of the standard liquid injected we have calculate the concentration of the
standard liquid. Choose more than one concentration to drew the curve
N=
= density of o-Xylene
24
C h a p t e r 3
25
This chapter contains results and conclusion
AUTO TITRATION
SAMPLE Dr.test T.S
H2S RSH
AUTO TITRATION
SAMPLE Dr.test T.S
H2S RSH
26
3.2 THE RESULT AFTER TREATING
AUTO TITRATION
SAMPLE Dr.test T.S
H2S RSH
AUTO TITRATION
SAMPLE Dr.test T.S
H2S RSH
27
3.3 DISCUSSION
The treatment proses was by using NaOH and mixing it with natural gasoline to remove sulfur
compounds in it.
After taking the sample of natural gasoline and analyzing it, the sulfur compound was as fig. (3.1) &
(3.2).
300
250
200
150
100
50
0
Dr.test RSH T.S
28
300
250
200
150
100
50
0
Dr.test RSH T.S
After treating with NaOH it appears that the sulfur compound decrease and Dr.test be free of sulfur
contents .The total sulfur level was decreased from 255 to 212 ppm as shown in figures (3.3) & (3.4) &
(3.5).
29
250
200
150
100
50
0
Dr.test RSH T.S
250
200
150
100
50
0
Dr.test RSH T.S
30
300
250
200
150
100
50
0
Dr.test RSH T.S
3.4 CONCLUSION
Desulfurization of petroleum fractions by extraction with NaOH is an economic, simple, and efficient
process. The sulfur contents of the nature gasoline can be lowered up to 60%. The process has the
advantage of easy handling and the use of less expensive reagents over conventional
hydrodesulfurization, oxidative desulfurization, and adsorptive desulphurization, etc. which make use of
expensive chemicals, equipments, difficult to process and are more time-consuming.
31
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وزارة التعليم العالي و البحث العلمي
الجامعة التقنية الشمالية
كلية التقنية /كركوك
هندسة تقنيات الوقود و الطاقة
بحـــث تخـرج
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