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Microwave-Assisted Oxidative Desulfurization of Sour Natural Gas


Condensate via Combination of Sulfuric and Nitric Acids
Ehsan Moaseri, Akbar Shahsavand,* and Behnaz Bazubandi
Chemical Engineering Department, Faculty of Engineering, Ferdowsi University of Mashhad, Mashhad 9177948974, Iran

ABSTRACT: Sulfur components are traditionally considered as undesirable contaminants of liquid hydrocarbon fuels. Many
countries have passed strict regulations to keep sulfur content of dierent fuels as low as possible. On a daily basis, over 3000
barrels of sour gas condensate are produced in Khangiran natural gas processing plant with an annual growth rate of around 16%
in the last six years. In pursue of our previous researches, a mixture of nitric and sulfuric acids is introduced as a novel oxidative
desulfurization agent. Also, the eect of microwave radiation was studied on desulfurization eciency of proposed agent. Both
hydrogen sulde and mercaptans are totally eliminated from sour gas condensate and its total sulfur content is severely reduced
from 8500 ppm to less than 300 ppm.

1. INTRODUCTION operational conditions have been proposed to enhance the


Sulfur compounds are usually known as one of the most eciency of HDS process for these sterically hindered sulfur
noxious and notorious petroleum contaminants.1,2 More than compounds, this approach is usually rejected due to sharp
195 types of sulfur compounds are recognized in crude oil such increase in both investment and operational costs.11
as hydrogen sulde, organic suldes and disuldes, benzothio- Oxidative desulfurization (ODS) process can be considered
phene, dibenzothiophene, and their alkylated derivatives.3 as an alternative or complementary process for HDS
During the combustion, these compounds release sulfur oxides method.12,13 The ODS process consists of two following
(SOx) and sulfate particles into atmosphere, which can lead to consecutive steps:
severe air pollution problems and acid rain falls.4 Due to the (a) Initially, the sulfur compounds are oxidized to their
depletion of sweet oil and gas reservoirs, oil and gas producers corresponding sulfoxides or sulfones by an oxidative
around the globe are forced to utilize sour oil and gas wells. agent.
This issue can lead to excessive release of SOx into atmosphere. (b) Afterward, highly polarized sulfoxides or sulfones are
Growing concerns on environmental issues enforce the extracted by an appropriate polar solvent or adsorbed on
governments to pass restriction rules for permissible sulfur high-capacity adsorbents.
content thresholds. Legislation of 15 and 10 ppmw as the
acceptable standard levels of sulfur compounds in diesel fuels of Compared to HDS process, the ODS technique has attracted
the US and EU, respectively, represents the eorts in pursuit of special attentions for its high removal eciency of alkylated
ultraclean fuels.5,6 Hence, desulfurization plants are becoming aromatic sulfur compounds in liquid phases under mild
an inseparable and essential part of rening process. temperatures and pressures. Also, reasonable capital investment
At the present, hydrodesulfurization (HDS) technique is and operational costs are two other advantages of this process.
almost the dominant desulfurization process, which is widely Beside these, ODS process does not require any hydrogen, and
used all around the world.7 This process is based on surface it can be accomplished in the absence of any hydrogen source.
adsorption of almost all sulfur compounds on appropriate Various oxidative agents have been reported to be used for
metallic catalyst surfaces. Subsequently hydrogenation of the desulfurization of petroleum cuts. Some of these processes are
corresponding sulfur compound takes place under high partial based on application of single oxidants, such as hydrogen
pressure of hydrogen. Thus, the sulfur compound is converted peroxide,14 nitric acid (HNO3),1518 organic hydroperoxides,19
to corresponding hydrocarbon and hydrogen sulde (H2S) gas molecular oxygen,20 ozone,21 air,22 sulfuric acid (H2SO4),23
as an undesired byproduct. Recent studies have revealed that potassium ferrate,24 Fentons reagent.25 A number of other
the sulfur removal eciency of HDS process depends on the ODS processes employ a combination of two agents. The rst
chemical nature (structure and bulkiness) of the sulfur one acts as the oxidant and the second agent catalyzes the ODS
compounds involved in hydrodesulfurization.8 While HDS is reactions. The recruitment of hydrogen peroxide with formic,
successful in desulfurization of aliphatic thiols, mercaptans, acetic, nitric, and phosphoric acids2629 are the popular
thioethers, suldes, disuldes, and thiophene, this process is less examples of such binary agents. Moreover, many solid basic
eective in removal of alkylated aromatic sulfur compounds, catalysts have been reported for enhancement of oxidation yield
such as dibenzothiophene (DBT) and its derivatives.9,10 In via hydrogen peroxide. Alumina-supported polymolybdates,30
practice, the sulfur compound should be initially adsorbed on vanadium(V) oxide/aluminum oxide (V 2 O 5 /Al 2 O 3 ), 31
the metal catalyst surface in order to be hydrogenated.
Evidently, steric hindrance of alkylated aromatic sulfur Received: September 16, 2013
compounds restricts appropriate adsorption of these com- Revised: December 30, 2013
pounds on the catalytic surface. Although more severe Published: December 30, 2013

2013 American Chemical Society 825 dx.doi.org/10.1021/ef4018515 | Energy Fuels 2014, 28, 825831
Energy & Fuels Article

vanadium(V) oxide/titanium dioxide (V2O5/TiO2),32 cobalt- Table 1. Characteristics of Khangiran Gas Processing Plant
molibden/aluminum oxide (CoMo/Al2O3),33 molibden/ Sour Condensate
aluminum oxide (Mo/Al2O3)34 are mostly used as the solid
property method unit amount
catalysts among many others.
In addition to these liquid and solid phase catalysts, high- Sp.Gr. 60/60 F D-4052 0.7959
energy radiations may be also employed to improve the sulfur TSC D-1266 ppm (wt) 8210
removal eciency through activation of oxidation process. mercaptans D-3227 ppm (wt) 456
Plasma radiations for molecular oxygen,35 UV irradiation for H2S D-1159 ppm (wt) 150
activation of hydrogen peroxide36 and microwave-assisted acidity D-664 mg KOH/g 0.19
ODS37 are the examples of such high-energy radiation viscosity @ 100 F D-445 c.St. 1.143
utilization. water content D-4928 Wt% <0.02
In our previous research, we reported that the addition of molecular weight IP-86 g/mol 140
concentrated H2SO4 to sour condensate is able to achieve 90% aromatics D-1319 vol % 19.9
desulfurization eciency.38 Due to its reasonable capital and olens D-1319 vol % <0.3
operational cost, the H2SO4 is nominated as the appropriate naphthenic D-1319 vol % 64.1
choice for successful ODS process. paranic D-1319 vol % 16
In the present article, it has been investigated the caloric value, gross D-240 kcal/kg 11085
combination of H2SO4 with HNO3, as another strong oxidant, chemical analysis
in pursuit of even deeper desulfurization and achievement of components mole percent components mole percent
ultraclean fuels. To the best of our knowledge, combination of C6 1.3 C11 17
H2SO4 and HNO3 has not been reported to be used for C7 2.6 C12 12.2
desulfurization of petroleum cuts. Eect of dierent operational C8 7.5 C13 7.5
conditions such as HNO3 to H2SO4 volumetric ratio (NSR), C9 18 C14 4.0
oxidative agents to sour condensate volumetric ratio (OCR) C10 21 C15 3.0
and process temperature has been studied to predict the
optimal conditions. Moreover, microwave radiations have been 500 mL distilled water to ensure the removal of residual salts and
also used during the desulfurization process to improve the excess oxidative agents remaining inside the treated condensate. The
sulfur removal eciency of sour natural gas condensates. A intensity of stirring and mixture temperature were controlled via a
novel set up has been proposed for microwave radiation temperature conditioned magnetic stirring system. Since desulfuriza-
assisted ODS that can simultaneously control the power output tion reactions are all exothermic, the temperature of all mixtures was
maintained at 80 C and the eect of temperature variations on
of radiations and the temperature of the mixture. desulfurization eciency was not studied.

2. MATERIALS AND METHODS 3. EXPERIMENTAL SETUP FOR MICROWAVE


Similar to our previous work, the sour natural gas condensate was RADIATION
obtained from the Khangiran sour gas processing plant. The Khangiran To study the eect of high energy radiations on sulfur removal
renery has been located in northeast of Iran and produces around 80 eciency, microwave radiations with dierent output powers were
thousand metric tons of sour gas condensate in 2013. The production applied to sour condensate during the oxidation process using a
rate of the sour condensate is anticipated to increase sharply due to the specially designed microwave oven. The oven was equipped with a
decrease of Mozdouran reservoir pressure, which pushes the PID controller (model: TNZ4SSeries) in order to maintain the
production pressuretemperature (PT) line into the sour gas phase mixture temperature in the desired output power of radiations. In
envelope. other words, the radiations were not continuous and the controller
2.1. Characteristics of Sour Natural Gas Condensate. The switched the power on and o to maintain the temperature around the
detailed physical and chemical properties of the sour condensate used set-point. The controller was appropriately tuned with rise time of less
in various ODS experiments are presented in Table 1. As expected, the than 10 s and overshoot of around 15%. A three-neck at
sour condensate contains considerable amounts of sulfur compounds, polytetrauoroethylene vessel was constructed as the reactor vessel
classied into three categories of H2S, mercaptans (thiols), and total and equipped with a thermocouple (up to 200 C) and an overhead
sulfur content (TSC), based on their elimination priorities. Evidently, stirrer (300 rpm). For safety purposes, all experiments were performed
these high amounts of sulfur compounds will cause several operational under nitrogen atmosphere and for comparison purposes the ODS
problems and hazardous environmental issues. reaction temperature was set at 80 C by the PID controller.
2.2. Reagents and Solvents. Merck H2SO4 (98 wt %) and HNO3
(63 wt %) was used in all experiments. Distilled water with 106 1 4. RESULTS AND DISCUSSIONS
cm1 conductivity was used in all tests for post wash purposes. All
chemicals were used as received unless stated otherwise. The following sections represent the collected results for
2.3. Sulfur Content Analysis. All treated condensates were several desulfurization experiments obtained by using dierent
sampled and analyzed for H2S, mercaptans and TSC by ASTM oxidative agents in the absence or presence of microwave
methods of D-1159, D-3227 and D-1266, respectively, by Khangiran radiations.
gas processing plant laboratory. 4.1. Treatment via H2SO4/HNO3 Solution in the
2.4. ODS Experimental Procedure. The ODS experiments were Absence of Microwave Radiation. Initially, the desulfuriza-
performed by treating sour condensate with oxidative agents of H2SO4 tion of sour natural gas condensate was carried out with
or combination of H2SO4 and HNO3, under dierent OCRs, various dierent combinations of H2SO4 and HNO3 as oxidative agents
NSRs and several mixing times and stirring intensities.
For each operation, 100 mL sour condensate has been sampled and in the absence of microwave radiation. Several OCRs (0.5, 1,
treated at ambient pressure. The sour condensate was mixed with the 1.33, and 2) with NSRs of 0, 0.3, 1, and 3 were used under
oxidative agent in a three-neck at ange reaction vessel under agitation times of 2, 5, 10, 15, and 20 min. The eect of H2SO4
nitrogen atmosphere. After each treatment, the condensate was concentration on desulfurization eciency was not assessed
separated from oxidative agent via separating funnel and washed by because our previous study38 revealed that only concentrated
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H2SO4 provides satisfactory desulfurization eciency. The


conducted experiments indicated that the water to treated
condensate volume ratio of 5:1 was optimal, which completely
removed the oxidized components and extraneous acids from
the organic phase. The pH of the treated condensates was
around 7 after such washing process.
Table 2 illustrates the amount of residual sulfur compounds
remained in the treated condensates in terms of H2S,

Table 2. Experimental Results for Various Runs in the


Absence of Microwave Radiation
run agitation time H2S RSH TSC
no. NSR OCR (min) (ppm) (ppm) (ppm)
1 0 0.5 15 NILa NIL 1200
2 0 1 15 NIL NIL 1060
3 0 1.33 15 NIL NIL 800
4 0 2 15 NIL NIL 700
5 0 2 2 71.9 168.9 4700
6 0 2 5 25.3 126.6 2800
7 0 2 10 NIL 31 1050
8 0 2 20 NIL NIL 670
9 0.3 0.5 15 NIL NIL 1100
10 0.3 1 15 NIL NIL 860 Figure 1. Variations of TSC of treated condensates in the absence
11 0.3 1.33 15 NIL NIL 780 microwave radiation: (A) with NSR at dierent OCRs, (B) with
agitation times at dierent NSRs.
12 0.3 2 15 NIL NIL 600
13 0.3 2 2 29.7 52.5 4300
14 0.3 2 5 NIL 16 1650 As can be seen, plot of TSC of treated condensates versus
15 0.3 2 10 NIL NIL 980 NSR for dierent values of OCR shows a relatively distinct
16 0.3 2 20 NIL NIL 400 minimum for all four curves at NSR = 0.3. Also, the TSC of
17 1 0.5 15 NIL NIL 3500 treated condensates decreases for all values of OSC by raising
18 1 1 15 NIL NIL 2860 this ratio from 0 to 0.3. Thus, high NSRs (higher than 0.3) lead
19 1 1.33 15 NIL NIL 1940 to ineective desulfurization of sour condensate. This result
20 1 2 15 NIL NIL 1010 clearly illustrates that the NSR plays a crucial role in eective
21 3 0.5 15 NIL NIL 6800 desulfurization of sour condensate.
22 3 1 15 NIL NIL 6100 The reason behind the eectiveness of the HNO3/H2SO4
23 3 1.33 15 NIL NIL 5840 solution is the high standard reduction potential of nitronium
24 3 2 15 NIL NIL 5630 cation produced during mixing of HNO3 with H2SO4 which
a provides larger oxidative tendency. As stated in literature, the
NIL: less than 1 ppm.
standard reduction potentials of H2SO4 and HNO3 are 0.16 and
0.957, respectively.40,41 Addition of HNO3 to H2SO4 leads to
mercaptans and TSC for various runs and in the absence of the formation of nitronium cation (NO2+) based on the
microwave radiation. As it can be seen, H2S and mercaptans are following reaction:
completely removed after all treatment except when the HNO3 + 2H 2SO4 NO2+ + H3O+ + 2HSO4 (1)
agitation time is very low (2 and 5 min). Therefore, eective
eliminations of H2S and mercaptans can be achieved by using The nitronium cation is an extremely strong oxidation agent
sucient treatment time with all of these combinations of with the standard reduction potential of +1.6 V at pH = 7.0.42 It
oxidative agents. has been reported that this cation is able to oxidized even
Figure 1A represents the variations of TSC of treated strictly hindered and stable sulfur compound such as benzene
condensates with NSR at dierent OCRs. As expected, the TSC ring with an attached sulfur.43,44 For instance, highly refractory
reduces by increasing the OCR. Although the TSC of the sulfur compounds such as thiophene and DBT can be oxidized
treated condensate may be further decreased by using higher by nitronium cation based on the reactions shown in Figure 2.
OCRs, the OCR value of around 2 is recommended based on Hence, the generation of such strong cation can further
economical considerations. It should be noted that at the OCR enhance the desulfurization eciency of H2SO4 through both
of 0.5, the minimum TSC of treated condensate is about 1100 improving the desulfurization reaction eciency of H2SO4 and
ppm. On the other hand, at OCR = 2, the minimum value of oxidizing the sulfur compounds resistant to H2SO4. In addition,
TSC is around 600 ppm, which is much lower than the it should be emphasized that, based on the reaction 1, the
previous one. Many literatures have stated that H2SO4 can solution with NSR = 0.3 has the highest concentration of
eectively desulfurize simple structure sulfur compounds such nitronium cation compared to other NSRs that has been used.
as H2S, mercaptans, suldes, disuldes, and even thiophenes;39 Furthermore, H2SO4 is a strong desulfurization agent for
however, this reagent is not capable of oxidizing alkylated organic sulfur compounds (OSC),39 and run no. 4 of Table 2
aromatic sulfur compounds, such as DBT. Hence, the remained depicts that desulfurization of sour condensate with just H2SO4
700 ppm of TSC in the treated condensate with H2SO4 mainly reduces more than 90% of TSC. On the other hand, HNO3
consists of highly alkylated aromatic sulfur compounds. shows strong desulfurization tendency for inorganic sulfur
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Figure 2. Oxidation of refractory sulfur components by nitronium cation: (A) reaction with thiophene and (B) reaction with DBT.

Figure 3. Formation of stable emulsion in condensate treated by H2SO4 by increase of agitation intensity: (A) 100 rpm, (B) 300 rpm, (C) 500 rpm,
(D) 700 rpm.

compounds.45,46 Since OSC comprises most of the TSC of sour diameter of the droplet size; smaller is the diameter of the
condensate, the nitric acid should be used as a limiting reactant droplet, lesser will be the rate of creaming. Therefore, reduction
in the reaction of nitronium production. in droplet size, caused by higher agitation intensities, lead to
Figure 1B shows the eect of agitation time on the TSC of signicant reducing the creaming rate and eventually
treated condensates by H2SO4 and combination of HNO3/ permanent connement of these droplets in the aqueous
H2SO4 at optimal volumetric ratio of 0.3. Both of these phase, known as stable emulsion.47 Elimination of such stable
oxidative solutions provide similar behaviors and the slope of emulsions necessitates costly operations such as the use of
TSC gradually decreases by increasing the agitation time and certain chemical de-emulsiers or application of some external
asymptotically approaches to less than 1000 ppm at 15 min. electric or magnetic elds.4851 Figure 3 shows the images of
Evidently, 15 min can be considered as the optimum agitation condensates treated by concentrated H2SO4 with dierent
time for successful desulfurization of sour condensate for both agitation intensities. As can be seen, the agitation intensities of
oxidative agents. Evidently, considering the asymptotic nature 100 and 300 rpm provide a homogeneous single phase solution.
of all corresponding curves, longer agitations are not supposed Using higher intensities (500 and 700 rpms) produce
to further reduce TSC and based on both technical and considerable amounts of stable emulsions. Based on these
economic considerations higher agitations are not advised. results, operating with agitation intensity around 300 rpm is
Considering the obtained results, the eective parameters on recommended to prevent emulsion formation.
the desulfurization eciency in the absence on microwave 4.2. Microwave-Assisted ODS of Sour Condensate.
radiation can be arranged based on order of eectiveness as Microwave radiation was applied during the ODS treatment of
follows: agitation time, OCR and NSR. Obviously, the use of sour condensate by H2SO4 and the combination of HNO3/
HNO3/H2SO4 solution provide slightly better desulfurization H2SO4. The microwave-assisted ODS experiments were carried
(600 ppm) result at optimal agitation time and optimum OCR out in three dierent microwave output powers (300, 500, and
value, compared to concentrated H2SO4 solution (700 ppm). 700 W), with retention times of 2, 5, 10, 15, and 20 min at
Agitation intensity of sour condensate with oxidative agent is OCR of 2 and NSR of 0 and 0.3 (see Table 3).
another important operating variable. By mixing aqueous and Figure 4A shows that the desulfurization eciency is
organic phases, droplets of immiscible organic phase in dierent improved with increasing the microwave radiation output
sizes are produced inside aqueous phase. Evidently, increasing power for both oxidative agents. Also, it seems that the
agitation intensity may lead to more ecient desulfurization by microwave radiation has more inuence on the eciency of
constructing smaller dispersed phase droplets, which will ODS treatment with HNO3/H2SO4. Figure 4B represents the
provide more mass transfer area between aqueous and organic eect of retention time on the TSC of condensates treated by
phases. On the other hand, employment of excessive agitation microwave-assisted ODS with H2SO4 and the combination of
intensities may create stable emulsions; the formed droplets HNO3/H2SO4. Although the microwave radiation improves the
tend to coalesce with each other due to high interfacial energy desulfurization eciency, the trend of the time dependence
and consequently cream above the aqueous phase. However, charts are still comparable with the curves obtained in the
based on Stokes law, the rate of creaming is inuenced by the absence of microwave radiation. The obtained results indicate
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Table 3. Sulfur Contents of Microwave-Assisted Treated microwave radiation provides a selective heating process.
Condensates via Dierent Oxidative Agents These radiations are absorbed by polar components and can
easily pass through nonpolar species. Therefore, microwave
microwave retention
run output power time TSC radiation leads to selective absorption of energy by oxidizing
no. NSR OCR (W) (min) H2S RSH (ppm) agents and most of the sulfur compounds (which are polar
1 0 2 300 15 NIL NIL 580 components), without any discernible eect on hydrocarbons
2 0 2 500 2 NIL NIL 3100 (mostly nonpolar components). In other words, signicant
3 0 2 500 5 NIL NIL 2250 portion of sulfur compounds including mercaptans, sulfoxides,
4 0 2 500 10 NIL NIL 980 sulfones, suldes, and disuldes are among polar components;
5 0 2 500 15 NIL NIL 530 this can eectively accelerate the desulfurization reactions by
6 0 2 500 20 NIL NIL 510 providing sucient activation energy through microwave
7 0 2 700 15 NIL NIL 510 radiation. Moreover, since all of oxidizing agents are highly
8 0.3 2 300 15 NIL NIL 420 polar molecules, the desulfurization of even nonpolar sulfur
9 0.3 2 500 2 NIL NIL 2840 components can be notably enhanced due to the fact that
10 0.3 2 500 5 NIL NIL 1130 oxidizing agents are highly activated under microwave
11 0.3 2 500 10 NIL NIL 570 radiations, which can lead to further desulfurization of these
12 0.3 2 500 15 NIL NIL 350 nonpolar sulfur components (e.g., DBT and aryl sulfur
13 0.3 2 500 20 NIL NIL 300 compounds).
14 0.3 2 700 15 NIL NIL 280 The second discussion suggests that while the more polar
species may absorb microwave energy more eectively, this
energy is immediately turned to heat and the heat dissipates
across the entire reaction mixture. Hence, any dierences are
solely due to dierences in heating rate and also temperature.
The authors believe that both approaches enjoy a broad overlap
and actually stem from similar roots.

5. ENVIRONMENTAL ISSUES
Complete elimination of hydrogen sulde and mercaptans with
considerable reduction of TSC (from 8500 ppm to around 280
ppm) of more than 3000 bbl/day production of Khangiran sour
gas condensate can prevent the emission of more than 6.5 t of
various sulfur oxides (SOx) in to the atmosphere. Evidently,
such immense reduction in SOx emission has great environ-
mental advantages. On the other hand, with an eye on the
optimal values of OCR (2) and NSR (0.3) and considering
around 3% bleed ratio, based on the experimental results
obtained via titration of the spent acids with standard caustic
solution, considerable amounts of depleted sulfuric and nitric
acids should be discarded, in each 24 h (135 and 45 bbl/day,
respectively). Haphazard disposal of these hazardous materials
may create other environmental issues and presents another
Figure 4. Variations of TSC of treated condensates treated with (A) challenge for our future researches. Practical approaches can
microwave output power and (B) retention time. include either safe disposal methods52,53 or regeneration cycles
of depleted acids.54
that the ODS eciency of sour condensate by the combination
of H2SO4 and HNO3 can be improved up to 30% in the 6. CONCLUSION
presence of microwave radiations. To complete the order of Sour gas condensate production of Khangran natural gas
eectiveness of operational parameters in the ODS process in renery has been tripled in the last six years. Transportation,
the presence of microwave radiations, parameters can be storage, and consumption of these condensates have led to
arranged as follows: agitation time, OCR, NSR, and microwave several health and environmental issues. Ecient desulfuriza-
radiation power. tion of sour condensates can drastically improve HSE
Interestingly, microwave-assisted ODS via HNO3/H2SO4 standards. A novel mixture of nitric and sulfuric acids is
solutions could eectively desulfurize the sour condensate introduced as an ecient ODS agent. It is clearly shown that
with considerable removal eciency of as high as 97%. It seems the use of microwave radiation can signicantly improve the
that most of the remaining sulfur compounds (280 ppm) desulfurization eciency. The proposed oxidative agent
should be sterically hindered or highly stable (refractory) sulfur completely eliminated the hydrogen sulde and mercaptans
components, such as DBT, benzo naphtho thiophene, benzo and signicantly reduced the TSC of a typical sour gas
phenanthro thiophene, and pyridyl benzothiophene, which condensate from 8500 ppm to around 280 ppm. It was clearly
even nitronium cation cannot eectively oxidize them. shown that by using the optimal OCR and NSR values, the
The following somehow dierent points of view may explain proposed ODS agent can prevent the emission of more than
the eectiveness of microwave radiation in enhancement of 6.5 tons per day of SOx, which provides valuable environmental
ODS eciency. The rst mechanism postulates that the benets.
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Article

AUTHOR INFORMATION (19) Liotta, F. J.; Han, Y. Z. Production of Ultra-Low Sulfur Fuels by
Selective Hydroperoxide Oxidation; National Petrochemical & Reners
Corresponding Author Association: Washington, DC, 2003.
*Tel.: 098 511 8810739. Fax: 098 511 8816840. E-mail: (20) Kharasch, M. S.; Nudenberg, W.; Mantell, G. J. Reactions of
Shahsavand@um.ac.ir. atoms and free radicals in solution. XXV. The reactions of olefins with
Notes mercaptans in the presence of oxygen. J. Org. Chem. 1951, 16 (4),
The authors declare no competing nancial interest. 524532.

(21) Wang, J.; Zhao, D.; Li, K. Oxidative desulfurization of


dibenzothiophene using ozone and hydrogen peroxide in ionic liquid.
ACKNOWLEDGMENTS Energy Fuels 2010, 24 (4), 25272529.
The authors wish to acknowledge the kind assistance of Dr. (22) Guo, W.; Wang, C.; Lin, P.; Lu, X. Oxidative desulfurization of
Morteza Maghrebi and Dr. Majid Baniadam for providing the diesel with TBHP/isobutyl aldehyde/air oxidation system. Appl.
microwave oven. The authors also acknowledge the valuable Energy 2011, 88 (1), 175179.
(23) Nehlsen, J.; Benziger, J.; Kevrekidis, I. Oxidation of aliphatic and
contributions of Khangiran gas renery ocials for performing
aromatic sulfides using sulfuric acid. Ind. Eng. Chem. Res. 2005, 45 (2),
all necessary analysis tests for collected samples.

518524.
(24) Liu, Y.; Song, H.; Zhang, W. Oxidative desulfurization of model
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