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Synthesis and evaluation of some amine compounds having surface active

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Article  in  Egyptian Journal of Petroleum · October 2014

DOI: 10.1016/[Link].2014.08.008

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Egyptian Journal of Petroleum (2014) xxx, xxx–xxx

Egyptian Petroleum Research Institute

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FULL LENGTH ARTICLE

Synthesis and evaluation of some amine compounds

having surface active properties as H2S scavenger
Nadia G. Kandile a, Taha M.A. Razek b, Ahmed M. Al-Sabagh c,*
,
Maamoun M.T. Khattab d

a
Faculty of Women, Ain Shams, Egypt
b
Institute of Environmental Studies and Research, Ain Shams University, Egypt
c
Egyptian Petroleum Research Institute, Nasr City 11727, Cairo, Egypt
d
Qarun Petroleum Company, Egypt

Received 26 August 2013; accepted 31 October 2013

KEYWORDS Abstract In this work three H2S scavengers were prepared by reacting monoethanolamine with
Hydrogen sulfide scavenger; formaldehyde in different ratios (1:1, 2:1 and 2:3) to give MF1, MF2 and MF3, respectively. The
Micellization; chemical structures of the prepared scavengers were confirmed by FT-IR spectroscopy. The effect
Thermodynamic parameters; of reaction time (the time required for completing the reaction between the scavenger and the H2S
Minimum surface area gas) has been studied for the three prepared scavengers. The effects of concentration and temper-
ature have been studied on the scavenging efficiency of H2S using three prepared products and
two commercial products EPRI-710 and EPRI-730. The surface and thermodynamic parameters
of the prepared scavengers were determined at 25 C including, surface tension (c), and effective-
ness, maximum surface excess (Cmax) and minimum surface area (Amin). Also, the standard free
energy of micellization and adsorption was recorded. The results show that the efficiency of scav-
engers increased with increasing reaction time up to 50 min. Also, as concentration of scavengers
and temperature increased, the removal efficiency of the scavengers increased. By comparing the
efficiency of the prepared products with the commercial products EPRI-710 and EPRI 730, it
was found that, MF3 exhibited a similar efficiency comparing with the commercial scavenger EPRI
730 (currently used in the field) at different concentrations and temperatures.
ª 2014 Production and hosting by Elsevier B.V. on behalf of Egyptian Petroleum Research Institute.

1. Introduction

* Corresponding author. The toxicity of hydrogen sulfide in hydrocarbon streams is well

Peer review under responsibility of Egyptian Petroleum Research known in the industry and considerable expense and efforts are
Institute. expended annually to remove hydrogen sulfide to a safe level
[1]. When the concentration of H2S exceeds 3 parts per million
(ppm) (v/v) in the gas phase, the oil well is deemed to be sour,
Production and hosting by Elsevier and precautions are necessary in the design and operation of

[Link]
1110-0621 ª 2014 Production and hosting by Elsevier B.V. on behalf of Egyptian Petroleum Research Institute.

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2 N.G. Kandile et al.

is promoted in the presence of sulfides. The atomic hydrogen

can diffuse into the metal, reduce ductility and increase suscep-
tibility to cracking. High strength metallic materials and hard
weld zones are prone to SSC [8]. Scavenging of hydrogen sulfide
is the preferred method for minimizing the corrosion and oper-
ational risks in offshore oil production [9]. The illustrated
methods in the case of removal of H2S gas are physical–
chemical treatment, cleaning, adsorption on particle surfaces
and absorption by liquid solvents [10]. The effects and perfor-
mance of H2S scavenger at various operational parameters
(i.e. type of crude, water cut, temperature, contact time and
flow pattern) are not completely understood. A laboratory test-
ing protocol and experimental equipment were designed and
constructed in order to: (1) evaluate the performance of H2S
scavengers under simulated multiphase flow field conditions,
and (2) facilitate the selection of commercial products to be
injected into oil lines [11]. Moreover, acid gas impurities must
be purified in order to meet the requirements of the gas
mixture sequential processing. Commercially alkanolamines
for the approach are monoethanolamine (MEA), diethanola-
mine (DEA), diisopropanolamine (DIPA), methyldiethanol-
amine (MDEA), and 2-amino-2-methyl-l-propanol (AMP).
Among these alkanolamines, MDEA as an absorption solvent
of acid gases is widely used today because it possesses charac-
teristics such as higher H2S selectivity, bigger absorption capac-
ity, lower regeneration energy, smaller hot-degradation and
Figure 1 Synthesis of H2S Scavengers; MF1, MF2 and MF3. low corrosion [12]. The present work reported the preparation
of H2S scavengers based on alkanolamines and evaluated its
reactivity as H2S scavenger.
production, transport, and storage equipment due to H2S tox-
icity, corrosion, plugging of reservoir formations, and increased 2. Materials and methods
sulfur content of the produced oil [2]. Arnold (1985) reported
that exposure to high concentrations of H2S, even for a brief
period, is extremely toxic to humans. The deleterious effects Technical grade of mono-, di- and tri-ethanol amine was pur-
of H2S have been recognized in a myriad of natural and indus- chased from Aldrich Co. Ltd. (UK). Formaldehyde solution
trial settings, including the oil and gas industry, where the (37%) was purchased from Aldrich Co. Ltd. (UK), (molecular
majority of H2S induced poisonings occur [3]. Human health weight 30.03 g/mol, density = 1.09 g/ml at 25 C). p-Toluene
effects of exposure to hydrogen sulfide, an irritant and an sulfonic acid was (p-TSA) purchased from Aldrich Co. Ltd.
asphyxiant, depend on the concentration of the gas and the (UK). Two blank commercial samples of H2S scavengers
length of exposure. About half of the population can smell EPRI-710 and EPRI-730 were submitted by Egyptian Petro-
H2S at concentrations as low as 8 parts per billion (ppb), and leum Research Institute (EPRI). Two types of sour crude oils
more than 90% can smell it at levels of 50 ppb. Hydrogen sul- (H2S concentration 4000 ppm and 14,000 ppm) were obtained
fide, however, is odorless at concentrations above 150 ppb, from North Qarun well (NQ3) and South West Qarun well
because it quickly impairs the olfactory senses. Prolonged expo- (SWQ3) respectively, Qarun Petroleum Company, Egypt.
sure to concentrations below150 ppb can also cause olfactory
fatigue [4]. At plants where hydrogen sulfide is removed from 2.1. Preparation of N,N-methylenebisoxazolidine (MF1), 1,3,5-
natural gas, sulfur dioxide (SO2) release may result. Sulfur is tris(2-hydroxyethyl-l,3,5-)-l,3,5-triazacyclohexane (MF2) and
often recovered from SO2 as a commercial by-product. Hydro- 1,7 dihydroxy-3,5-diazaheptan (MF3)
gen sulfide (H2S) dissolved in crude oil does not pose any dan-
ger, but, when it is produced at the wellhead in gaseous form, it In a 500 ml three-necked round flask equipped with a mechan-
poses serious occupational risks through possible leaks or ical stirrer, thermometer and a Dean–Stark connected to con-
blowouts [5]. The most important corrosive agents in primary denser, monoethanolamine reacted with formaldehyde
distillation plants are chlorides and H2S [6]. The internal corro- solution in ratios of 2:3, 1:1 and 2:1. Xylene 30% from the
sion of carbon steel in the presence of hydrogen sulfide repre- total content of reactants was added as an azeotropic solvent
sents a significant problem for both oil refineries and natural and the reaction was catalyzed by p-TSA (0.1%) of the total
gas treatment facilities [7]. At certain conditions H2S causes sul- reactant’s weight. The mixture was heated at 140 C with con-
fide stress cracking (SSC), which is defined as cracking of metal tinuous stirring until theoretical amount of water was col-
involving corrosion and tensile stress (residual and/or applied) lected. The solvent was distilled off and then the product
in the presence of water and H2S. Sulfide Stress Cracking (SSC) was purified [13,14].
is a form of hydrogen stress cracking (HSC) and involves The chemical structure of the prepared H2S Scavengers
embrittlement of the metal by atomic hydrogen that is pro- namely; MF1, MF2 and MF3 is shown in Fig. 1. The chemical
duced by acid corrosion on the metal surface. Hydrogen uptake structure was confirmed by the FTIR.

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Synthesis and evaluation of some amine compounds having surface active properties as H2S scavenger 3

2.2. Determination of H2S gas concentration 2.3. Surface tension measurements

The H2S concentration was measured using a gas chromato- Different molar concentrations of MF1, MF2 and MF3 were
graph (Shimadzu GC-4BM) equipped with a flame photomet- dissolved in double distilled water and their interfacial tensions
ric detector and a Teflon column (i.d., 3 mm; length, 6 m) were determined at 30 C using a Lecomte De Nouy tensiome-
packed with polyphenyl ether (5 rings) on 60–80 mesh 10% ter ring ‘‘Kruss model Gmbh’’. The instrument was daily regu-
Shimalite TPA. The column temperature, detector temperature lated using bi-distilled water (conductivity 1.1 · 106 ohm cm1
and injection temperature were 70, 230 and 130 C, respec- at 25 C) [16,17].
tively, and N2 was used as a carrier gas [15].

Figure 2 FTIR Spectra for (a) MF1, (b) MF2 and (c) MF3.

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4 N.G. Kandile et al.

The surface active properties of the prepared products, oxygen atoms are not in the hydroxyl, aldehyde or acid form.
maximum surface excess (Cmax), minimum surface area per The FTIR of MF2 is shown in Fig. 2b, the spectrum shows a
molecule (Amin), effectiveness pcmc, the free energy of micelliza- strong and broad band at 3350–3450 cm1 characteristic for
tion (DGmic) and the free energy of adsorption (DGads) were OH stretching vibration. Another band appeared at 2943 cm
1
calculated using the following equations [18]: characteristic for C–H stretching vibration. Also, the med-
Cmax ¼ ½1=RT½dc=dlncT ium band of C–N stretching vibration appeared at 1321 cm1.
The bands in Fig. 2c at 3494 and 3392 cm1 donated to the
N–H asymmetric and symmetric stretching vibration, respec-
Amin ¼ 1016 =½NA  Cmax 
tively to the secondary amine. The m N–H in plane bending
pcmc ¼ c0  ccmc vibration appears at 1604 cm1 and m C–N stretching vibration
appears at 1346 cm1. This meaning that, the H2O was
DGmic ¼ RT ln CMC removed as oxygen from the formaldehyde and two hydrogen
atoms from two molecules of the primary amine to form a pure
DGads ¼ DGmic  ½0:6022  pcmc  Amin  compound (MF3).

where, c0 is the surface tension measured for pure water at

appropriate temperature, ccmc is the surface tension at CMC, 3.1. Effect of reaction time on the efficiency of H2S scavenging
c is the surface or interfacial tension (mN/m), C is the concen-
tration of surfactant (mol/l), C is the surface excess concentra- Reaction time (the time required for completing the reaction
tion (mol/dm2), R is the molar gas constant (R = 8.314 J/ between the scavenger and the H2S gas) is one of the important
mol k), T is the absolute temperature = 333 K, Amin is the factors affecting the efficiency of the scavenging process in gen-
surface area per molecule of solute in square nanometers eral. Data illustrated in Table 1 for MF1, MF2 and MF3,
(nm2/molecule), NA is the Avogadro’s number (6.023 · 1023 showed that the H2S reading for NQ3 (4000 ppm) decreased
molecule/mole), DGmic is the free energy of micellization to 624, 495 and 356 ppm with increasing reaction time to
(kJ/mol), DGads is the free energy of adsorption (kJ/mol), 50 min. and the reading became fixed after 60 min at dose
and pcmc is the effectiveness of adsorption or surface pressure (500 ppm) and 40 C. The same behavior occurred for SWQ3
of surfactant. (14,000 ppm), which decreased to 5160, 4340 and 3760 ppm
and the reading became fixed after 60 min. at dose (500 ppm)
3. Results and discussion and 40 C. This may be due to the nature of the polar group
(hydrophilic part) in the scavenger which plays a main role
Three H2S scavengers were prepared from the reaction of in the scavenger of H2S. The most effective nonionic surfactant
monoethanolamine with formaldehyde in different ratios as H2S scavenger was ranked according to the heteroatoms
(2:3, 1:1 and 2:1) to give MF1, MF2 and MF3, respectively present in the molecules (N > O > S) [19] MF1 has 2 tertiary
[13,14]. nitrogen atoms and two oxygen atoms, MF2 has three nitro-
The infrared spectroscopy was used to confirm the chemical gen atoms and three OH groups, but MF3 has two secondary
structure of MF1, MF2 and MF3 as shown in Fig. 2. The spec- amines and two –OH groups. The latter structures of MF3
tra in Fig. 2a show a strong band at 1120 cm1 characteristic exhibited the maximum efficiency of the hydrogen sulfide scav-
for C–O stretch vibration. The disappearing bands at 1670– enging, this may be due to the secondary amine group which is
1820 cm1 of C‚O or at 3200–3600 cm1 of OH pointed to most effective than the tertiary amine group in the scavenging
no aldehyde, ester, alcohol or acid groups in the prepared mol- process. Accordingly, the increasing of the reaction time leads
ecule (MF1). On the other hand, also the band of NH stretch- to the increase in the chance of adsorption of the scavenger,
ing or bending vibration at 3300–3500 cm1 or 1600 cm1, which contains nitrogen atom on the gas/oil interface.
respectively disappeared. These features proved that the Thereby, the best results were obtained with MF3 (containing
obtained compound has tertiary nitrogen groups and the 2 nitrogen atoms).

Table 1 Effect of reaction time on H2S scavenging, for the prepared scavengers at 500 ppm and 40 C for NQ3 and SWQ3 crudes.
Reaction time, min MF1 MF2 MF3
Reading ppm Reading ppm Reading ppm Reading ppm Reading ppm Reading ppm
(NQ3) (SWQ3) (NQ3) (SWQ3) (NQ3) (SWQ3)
10 3820 10,200 2936 9340 2360 6950
20 2710 9480 2260 8260 1240 5820
30 2040 8450 1492 6430 824 4640
40 1320 6340 1080 5120 492 3980
50 624 5160 495 4340 356 3760
60 624 5158 495 4336 354 3760
70 624 5158 495 4336 354 3760
80 624 5158 495 4336 354 3760
90 624 5158 495 4336 354 3760
100 624 5158 495 4336 353 3760

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Synthesis and evaluation of some amine compounds having surface active properties as H2S scavenger 5

Table 2 Effect of dosage and temperature for MF1, MF2 and MF3 on H2S reduction of NQ3 crude.
Dose, ppm MF1 MF2 MF3 EPRI-710 EPRI-730
20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C
100 1150 998 789 693 1006 878 680 606 844 767 560 409 1000 885 685 600 840 760 555 400
200 1118 906 637 572 994 798 523 457 813 594 380 286 990 750 530 450 810 590 375 280
300 1102 818 540 480 968 702 440 368 790 520 309 221 960 665 445 360 785 515 300 215
400 1074 732 457 394 956 619 352 300 775 420 246 175 950 580 335 295 770 410 240 170
500 1058 624 383 336 938 495 297 244 763 356 215 129 930 549 290 240 760 350 210 125
600 1052 606 344 278 919 386 242 196 750 295 172 111 900 490 266 190 745 285 165 105
700 1047 594 293 238 910 334 188 150 744 253 117 84 890 465 248 145 740 245 110 80
800 1040 568 260 189 906 298 145 111 738 216 90 65 875 405 224 110 735 205 85 60
900 1034 551 220 152 906 284 100 71 731 183 47 27 865 370 198 70 726 175 42 20
1000 1034 538 184 113 906 278 80 46 731 180 20 8 865 330 180 40 726 170 15 5

Table 3 Effect of dosage and temperature for MF1, MF2 and MF3 on H2S reduction of SWQ3 crude.
Dose, ppm MF1 MF2 MF3 EPRI-710 EPRI-730
20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C 20 C 40 C 60 C 80 C
100 8400 6040 4980 4680 7200 5210 3740 3840 6480 4680 2930 2640 7950 5940 5360 4860 6330 4560 2780 2460
200 8000 5820 4750 4460 6830 5000 3520 3660 5870 4450 2710 2360 7690 5740 5080 4520 5740 4310 2550 2140
300 7690 5610 4510 4280 6410 4790 3300 3480 5280 4220 2480 2090 6310 5520 4710 4140 5160 4140 2310 1860
400 7220 5390 4270 4050 6020 4560 3080 3270 4810 3990 2260 1810 6080 5390 4320 3760 4710 3780 2180 1650
500 6840 5160 4030 3870 5590 4340 2890 3040 4260 3760 2030 1550 5870 5120 3940 3510 4160 3490 1920 1390
600 6390 4980 3890 3660 5190 4130 2680 2860 3810 3520 1840 1270 5620 4970 3650 3290 3740 3120 1690 1080
700 5910 4810 3680 3490 4740 3910 2470 2680 3490 3310 1660 980 5430 4800 3320 3060 3380 2940 1460 738
800 5580 4650 3480 3280 4410 3710 2280 2490 3100 3120 1480 760 5250 4610 3140 2880 3040 2790 1210 642
900 5360 4470 3290 3120 4220 3490 2060 2310 2870 2930 1290 530 5160 4430 2960 2690 2790 2640 1160 370
1000 5210 4290 3110 2930 4080 3280 1880 2140 2680 2740 1210 360 5110 4270 2910 2610 2620 2580 986 280

3.2. Effect of the chemical dosage and temperature on the H2S oil could reduce H2S in the treated gas. The reaction rate of
scavenging the tertiary amine is lower than that of the secondary and pri-
mary amines. As rules, MF1 and MF2 belong to the tertiary
Among the most important parameters governing the effi- amines, while MF3 belongs to the secondary amines. Accord-
ciency of the prepared scavengers are the scavenger concentra- ingly, the tertiary and secondary amines are suitably used for
tion and temperature. The effect of temperature and the total acid gas CO2 and H2S removal from the industrial
concentration of the prepared scavengers MF1, MF2 and gas streams [16]. Where, the temperature exhibited an acceler-
MF3 on the H2S reduction readings are shown in Tables 2 ation effect on the physicochemical absorption of H2S.
and 3. The results showed that, there is a correspondent Increase in temperature, resulted in increasing of H2S removed
decrease in the H2S reading values of the prepared scavengers from the gas stream [20]. This behavior was remarked in this
with the increase in H2S concentration (ppm). As a result, the study and also the maximum scavenging efficiency was
reduction of H2S gas may be attributed to two reasons; the first obtained by MF3. This finding proved that, the primary amine
is the increase of the collision factors between the H2S gas and is most effective than the secondary or tertiary amine.
the scavengers and the second is the increase of scavenger mol- Moreover, when we compare the efficiency of the prepared
ecules adsorption on the water /oil or oil/gas interface. There- products with the commercial products (EPRI 710 and EPRI
fore, increasing of the scavenger concentration in the treated

Figure 3 Effect of temperature on the H2S reading for MF1, Figure 4 Effect of temperature on the H2S reading for MF1,
MF2 and MF3 at dose 500 ppm for NQ3 crude. MF2 and MF3 at dose 500 ppm for SWQ3 crude.

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6 N.G. Kandile et al.

Table 4 Surface tension and thermodynamic properties for the prepared H2S scavengers at 25 C.
Scavenger CMC, mol dm3 c,mN/m Cmax1010, mol/cm2 Amin,nm2 p,mN/m DGmic,kJ /mol DGad,kJ /mol
2
MF3 1.44 · 10 50.7 1.56 10.62 21.3 10.5 10.36
MF2 2.57 · 102 40.22 2.38 6.97 31.7 9.06 8.93
MF1 3.44 · 102 27.3 3.09 5.35 44.7 8.34 8.20

Figure 5 Log c against tension for the prepared H2S scavengers at 25 C.

730), it was found that; MF3 exhibited a similar efficiency scavenging process was found. This means that the maximum
comparing with the currently used scavengers EPRI 730 [21] enrichment of the scavenger molecules on the interface was
at different concentrations and temperatures. By inspection exhibited with the scavenger, which has the smallest Amin. Also
of the obtained data shown in Figs. 3 and 4, it was found that a reversible proportion between Amin and Cmax was noticed in
with the increase of the temperature from 20 to 80 C, the H2S Fig. 5, the individual scavenger MF1 exhibited a lower Amin
removal efficiency was increased. This may be due to the and higher Cmax among MF2and MF3 scavengers. These
decrease in the solubility of H2S gas in the crude oil and evap- results of surface active properties for those products are con-
orate to the gas phase. Consequently, the increase of the tem- sisted with the emulsion stability for them.
perature leads to the decline of solubility of the acid gas (H2S) The more DGads value, indicates that the scavenger mol-
in the liquid phase. Therefore, the H2S gas was liberated into ecules adsorbed strongly on the interface. Generally, DGads
the gas phase. Accordingly, possibility of collision chance is slightly greater than DGmic, which mean that the molecules
between H2S and the scavenger molecules will be increased. prefer to adsorb on the interface than to make micelles. There-
This reason causes increase in the H2S removal efficiency of fore, maximum DGad. (10.36 kJ/mol) was obtained with
the scavengers with temperature. MF3 which exhibited the maximum efficiency.

3.3. Surface active properties of the prepared scavengers MF1,

MF2 and MF3 4. Conclusion

The surface active properties of MF1, MF2 and MF3 at 30 C In this study, the preparation of H2S scavengers MF1, MF2
are listed in Table 4 and illustrated in Fig. 5. From these data, and MF3 is reported. Evaluation of the efficiency of these
it was obvious that, the surface tension (c) was 50.7, 40.22, and compounds for scavenging H2S gas was carried out and prom-
27.3 (mN1/m) against MF1, MF2 and MF3, respectively. ising results were obtained. Compound MF3 showed the high-
Accordingly, the lowering of c depends on the concentration est scavenging efficiency of H2S gas. For SWQ3 sour crude, the
of the surfactant (scavenger) on the bulk of the solvent which three prepared products MF1, MF2 and MF3 achieved scav-
determines the reduction in c, as given by the Gibbs adsorp- enging efficiency of 79.1%, 84.7% and 97.4% respectively at
tion equation [18]. This finding meaning that, MF3 has greater dose 1000 ppm and temperature 80 C. Meanwhile the com-
surface active properties among the other scavengers (MF1 mercial products EPRI 710 and EPRI 730 achieved under
and MF2). This property puts MF3 in the former situation same conditions, scavenging efficiency of 81.4% and 98.0%
in the scavenging process. respectively. Where for NQ3 sour crude, the prepared products
By inspection of the data listed in Table 4, a clear relation MF1, MF2 and MF3 achieved under same conditions, scav-
between the surface active properties and the efficiency of H2S enging efficiency of 97.2%, 98.9% and 99.8% respectively

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Synthesis and evaluation of some amine compounds having surface active properties as H2S scavenger 7

and the commercial products EPRI 710 and EPRI 730 [9] Krishnaswamy Rajagopal, Roge Rio Lacerda, Ivan
achieved under same conditions, scavenging efficiency of Slobodcicov, Eugenio Campagnolo, Chem. Eng. Commun.
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