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The Structural Characterization of Saturate, Aromatic, Resin, and

Asphaltene Fractions of Batiraman Crude Oil

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DOI: 10.1080/10916460903330361

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The Structural Characterization

of Saturate, Aromatic, Resin, and
Asphaltene Fractions of Batiraman Crude
Oil
a a a a
S. Akmaz , O. Iscan , M. A. Gurkaynak & M. Yasar
a
Department of Chemical Engineering , University of Istanbul ,
Avcilar , Istanbul , Turkey
Published online: 07 Feb 2012.

To cite this article: S. Akmaz , O. Iscan , M. A. Gurkaynak & M. Yasar (2011) The Structural
Characterization of Saturate, Aromatic, Resin, and Asphaltene Fractions of Batiraman Crude Oil,
Petroleum Science and Technology, 29:2, 160-171, DOI: 10.1080/10916460903330361

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 Petroleum Science and Technology, 29:160–171, 2011
Copyright © Taylor & Francis Group, LLC
ISSN: 1091-6466 print/1532-2459 online
DOI: 10.1080/10916460903330361

The Structural Characterization of Saturate,

Aromatic, Resin, and Asphaltene Fractions
of Batiraman Crude Oil

S. AKMAZ,1 O. ISCAN,1 M. A. GURKAYNAK,1 AND

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M. YASAR1
1
Department of Chemical Engineering, University of Istanbul, Avcilar,
Istanbul, Turkey

Abstract The structural characterization of fractions of Batiraman crude oil, which

is the heavy crude oil from a field in the southeastern part of Turkey, was investigated.
Batiraman crude oil and its saturate, aromatic, resin, and asphaltene (SARA) fractions
were seperated. Treatment of crude oil with n-heptane provided the separation of
asphaltene. Maltene was collected by evaporating the n-heptane from the filtrate.
Then, maltene was separeted into saturates, aromatics, and resins by SARA technique.
Maltene was separated into saturate, aromatic, and resin fractions using column
chromatography. SARA fractions were quantified on a weight percent basis. Fractions
of Batiraman crude oil were characterized by elemental analysis, proton nuclear
magnetic resonance (1 H NMR) analysis, electrospray ionization mass spectrometry
(ESI-MS), and Fourier transform infrared (FTIR) spectroscopy techniques.

Keywords Batiraman crude oil, ESI-MS, FTIR, 1 H NMR, maltene, SARA

Crude oil is composed of paraffinic and aromatic hydrocarbon molecules containing

variable amounts of sulfur, oxygen, nitrogen, and trace amounts of metals such as nickel,
vanadium, iron, and copper (Speight, 2001; Yasar et al., 2001; Simanzhenkov and Idem,
2003). Chemical composition of crude oils differs according to location and age of the
field. Heavy crude oils contain higher complex hydrocarbon molecules, heteroatoms,
and metal contents compared with lighter crude oils. In these circumstances, processing
is more difficult for heavy crude oils. At current rates in the refining industry, light
crude oil reserves are decreasing rapidly. It is therefore necessary to characterize heavy
crude oil for converting heavy petroleum into more valuable products. Crude oils have a
complex chemical structure that is composed of a specific mixture of chemical compound
types. Different techniques are used to fractionate for the crude oils (Speight, 2001). The
saturates, aromatics, resins, and asphaltenes (SARA) technique is the most widely used
method to separate crude oils into major four fractions (Fan and Buckley, 2002; Klein
et al., 2006; Peralta-Martinez et al., 2008).
The saturate fraction mostly contains aliphatic compounds. The aromatic fraction
consists of aromatic groups with aliphatic side chains. Resin is a heavier fraction than

Address correspondence to Solmaz Akmaz, Department of Chemical Engineering, University

of Istanbul, Avcilar, 34320, Istanbul, Turkey. E-mail: solmaz@istanbul.edu.tr

160
 Structural Characterization of Batiraman Crude Oil 161

aromatics and saturates. Asphaltene is insoluble in n-alkane solvents and the most com-
plex fraction of crude oils. In these circumstances higher asphaltene content in crude oil
causes processing problems during refining operations (Ali et al., 1989; Gray, 1994; Fan
and Buckley, 2002).
Many reseachers have investigated structure of crude oil’s fractions. Elemental anal-
ysis, nuclear magnetic resonance (NMR) analysis, and Fourier transform infrared spec-
troscopy (FTIR) techniques are important analytical tools for the characterization of crude
oil fractions such as saturates, aromatics, resins, and asphaltenes. Elemental analysis
is used to determine carbon, hydrogen, oxygen, nitrogen, and sulfur; NMR is used
to determine the distribution of hydrogen and carbon according to structural type, and
Fourier transform infrared spectroscopy (FTIR) is used to determine functional groups
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in the fractions of crude oils (Ali et al., 1989; Rudzinski et al., 2000). Aske et al. (2001)
investigated 18 crude oils and its fractions by FTIR. Buenrostro-Gonzalez et al. (2001)
separated four Mexican oils into SARA fractions and analyzed resins and asphaltenes,
which are problematic fractions in oils. Peralta-Martinez et al. (2008) determined the
presence of carbonyl groups in the resin and asphaltene fractions of Mexican vacuum
residua using FTIR. Gel permeation chromatography (GPC) and electrospray ionization
mass spectrometry (ESI-MS) were used for determination of the molecular weight of
fractions of crude oils (Buenrostro-Gonzalez et al., 2001; Buch et al., 2003). Porter and
Mayer (2004) used Electrospray ionization mass spectrometry (ESI-MS) to analyze the
resin fraction from several crude oils. They obtained mass spectra of the polar constituents
of resins and made comparisons between them.
Understanding the molecular structure of heavy crude oils would provide to convert
crude oils into more valuable products during refinary processes. In this study, Turkish
crude oil (Batiraman) was investigated. Structural analysis of the asphaltene fraction of
Batiraman crude oil was investigated in our previous papers (Yasar et al., 2007, 2009).
Saturate, aromatic, and resin fractions were obtained from Batiraman crude oil. The ob-
tained fractions were investigated using elemental analysis, 1 H NMR, FTIR spectroscopy,
and ESI-MS. Combining structural analysis results obtained from elemental analysis,
FTIR, 1 H NMR, and ESI-MS, the possible hypothetical molecular structure for saturate,
aromatic, resin fractions was proposed. The possible hypothetical molecular structure for
the asphaltene fraction was proposed in our previous work (Yasar et al. 2009).

1. Experimental Methods

1.1. Asphaltene Precipitation

Batiraman crude oil was provided by Turkish Petroleum Corporation (TPAO). The prepa-
ration of asphaltene was described in our previous paper (Yasar et al., 2007, 2009;
ASTM D 6560). Atmospheric crude oil residue was obtained by removing the distillates
boiling up to 350ıC using atmospheric distillation. Treatment of atmospheric crude oil
residue with n-heptane provided the separation of asphaltene. Residue was added to
n-heptane in a 1:40 weight ratio. The mixture was stirred for 1 hr at 60ıC and was
continuous stirred for 4 hr at ambient temperature. The solution was then left to stand
overnight prior to filtering. Boiling heptane was used to verify the absence of maltene
in the asphaltene fraction. Also, asphaltene was purified with hot toluene by extraction.
Toluene was evaporated using a vacuum evaporator and asphaltene was dried in vacuum
oven.
 162 S. Akmaz et al.

1.2. SARA
Treatment of Batiraman crude oil with n-heptane provided the separation of asphaltene.
Maltene was collected by evaporating the n-heptane from the filtrate. Maltene was
separated into saturates, aromatics, and resins using the SARA technique after precipiting
asphaltene. Separation of maltene was carried out by column chromatography using the
following method. First, 10 g of maltene was dissolved in 100 mL heptane and was
applied to the top of a 4-cm-internal-diameter and 60-cm-long glass column packed with
silica gel (Baker, 40-140 mesh). The column was prewetted with about 300 mL of n-
heptane and the saturates fraction was eluted from the column by 1,000 mL n-heptane,
1,000 mL of a 50/50 vol% mixture of heptane and toluene, followed by 500 mL of
toluene to elute the aromatic fraction and 1,000 mL of a 50/25/25 vol% mixture of
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methanol, toluene, and petroleum ether followed by 500 mL of petroleum ether to elute
the resin fraction. Finally, solvents were removed using a vacuum evaporator. SARA
fractions were quantified on a weight percent basis (Yasar et al., 2000).

1.3. Analytical Chemistry

A Thermo Finnigan Flash Model EA 1112 elemental analyzer was used for the analysis
of Batiraman crude oil fractions for total carbon, hydrogen, sulfur, and nitrogen content.
The distribution of hydrogen and carbon according to structural type in the fractions was
investigated by 1 H NMR. 1 H NMR spectra were recorded in the pulse Fourier transform
mode using a Bruker spectrometer operating at 500 MHz for 1 H NMR spectra. Proton
types were assigned based on shifts noted in the literature (Speight, 2001; Akmaz, 2006).
FTIR spectra of crude oil fractions were recorded on a Perkin Elmer FTIR spectrometer.
The spectra of fractions were acquired using attenuated total reflectance (ATR).
The average molar mass of saturate, aromatic, and resin fractions was determined
using ESI-MS. All mass spectra of the fractions were obtained using a Finnigan iontrap
mass spectrometer equipped with Ion Max API source. From the ESI-MS spectral data,
the number average molecular mass of each fraction was calculated by taking the highest
average 155 mass values and multiplying them by its relative intensities.

2. Results and Discussion

Chemical analysis of Batiraman crude oil and Batiraman asphaltene was investigated
in our previous works (Yasar et al., 2007, 2009). The results of the fractionation and
characterization of Batiraman crude oil are given in Table 1. Batiraman crude oil, which
is a heavy crude oil, had high amounts of asphaltene (28%), resin (27%), and aromatic
fractions (26%). Karacan and Kok (1997) used the same crude oil in their work and their
asphaltene content was 29%. The fractions of Batiraman crude oil were characterized
by elemental analysis, 1 H NMR, and FTIR. The average molecular weight of saturate,
aromatic, and resin fractions was determined by ESI-MS. Molecular weight of Batiraman
asphaltene fraction was determined by GPC in our previous works (Yasar et al., 2007,
2009).
The elemental analysis results indicated that the hydrogen content of the asphaltene
fraction was the lowest, followed by aromatics, resin, and saturate fractions. The results
of hydrogen/carbon (H/C) ratios showed that saturate fractions has higher H/C ratio
than aromatics, resin, and asphaltene fractions. The H/C ratio of the asphaltene fraction
was the lowest. However, in our work, the H/C ratio of resin fraction was higher than
 Structural Characterization of Batiraman Crude Oil 163

Table 1
Chemical analysis of fractions of Batiraman crude oil

Analysis Asphaltene Saturate Aromatics Resin

% Weight of fraction 28 19 26 27
% Carbon 79.23 85.26 81.71 74.55
% Hydrogen 7.23 13.45 9.38 8.98
% Nitrogen 1.66 <1 <1 <1
% Oxygen 3.05 <1 <1 10.18
% Sulfur 8.83 0.81 8.28 6.29
H/C 1.09 1.89 1.38 1.45
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Mn 1,010 432 284 1,057

Proton NMR
% HMethyl 11.26 28.68 29.67 21.88
% HMethylene 36.14 70.22 37.25 56.53
% HNaftenic 26.11 — 12.02 —
% HAlfa 23.43 0.95 12.53 15.75
% HAromatic 3.07 0.14 8.53 5.83
CA 33 5 8 24
Cs 34 26 11 41
Fa 0.49 0.15 0.44 0.37

the aromatics, fraction, whereas the H/C ratio of saturate, aromatic, resin and asphaltene
fractions of Arabian heavy oil and Maya crude oil showed an increasing trend in Ali et al.
(1989) and Rudzinski et al. (2000). The H/C ratio suggests that the saturate fraction has
a less condensed aromatic ring. The saturate fraction contains mostly aliphaltic chains.
Sulfur contents of fractions are shown in Table 1. According to the elemental analysis
data for the fractions of Batiraman crude oil, asphaltene contains the highest sulfur amount
(8.83%) and the saturates contain the lowest sulfur amount (0.81%). This result supports
the fact that sulfur is mostly found in the polynuclear aromatic rings rather than in the
paraffinic chains (Rudzinski et al., 2000).
The 1 H NMR spectra results are shown in Figures 1–4. The distribution of hydrogen
according to structural type in the fractions of Batiraman crude oil listed in Table 1 was
determined by 1 H NMR spectra using the procedure of Speight (2001). The saturate
fraction contains a high amount of methylene hydrogen. Approximately all of the hy-
drogens in the saturate fraction are formed as methylene and methyl hydrogens (70.22,
and 28.68%, respectively). The saturate fraction consists of a very small amount of
aromatics and ˛-hydrogen. The 1 H NMR spectra results support the H/C ratio results
that Batiraman asphaltene contains more condensed aromatic rings and the saturates
have the mostly long paraffinic chains. Asphaltene, resin, and aromatic fractions consist
of 23.43, 15.75, and 12.53% ˛-hydrogen, respectively. These ˛-hydrogen levels indicate
that the branching is highest for asphaltene. The amount of ˛-hydrogen is the lowest in
the saturate fraction.
ESI-MS was used to determine the average molecular weight for the saturate, aro-
matic, and resin fractions. Mass spectras of fractions are shown in Figures 5–7. Average
molecular weight was calculated by using mass spectra. The results are listed in Table 1.
According to these results, the aromatic fraction was the smallest fraction followed by
 164 S. Akmaz et al.
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Figure 1. 1 H-NMR spectrum of Batiraman saturate fraction.

saturates. As shown in Table 1, the molecular weight of the resin fraction was higher
than the other fractions. Therefore, the reproducibility of the molecular measurement of
Batiraman crude oil was checked. Standard devision was less than 5% for all fractions.
The expected result was that the molecular weight of asphaltene might be higher than
resin. The molecular weight of asphaltene was determined by GPC in our previous work
(Yasar et al., 2007, 2009).
The carbon distribution in atoms per fraction calculated from 1 H-NMR, elemental
analysis, and molecular weight results is listed in Table 2. The aromaticity factor, fa ,
is the ratio of aromatic carbons to the total number of saturated and aromatic carbons.

Figure 2. 1 H-NMR spectrum of Batiraman aromatic fraction.

 Structural Characterization of Batiraman Crude Oil 165
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Figure 3. 1 H-NMR spectrum of Batiraman resin fraction.

The aromaticity factor calculated from elemental analysis, 1 H -NMR, and the number
average molecular weight (Mn) measurement is listed in Table 1. Batiraman asphaltene
(0.49) possessed the highest aromaticity, followed by aromatics (0.44), resin (0.37), and
saturates (0.15) asphaltenes.
FTIR spectroscopy was used to determine the functional group types in the fractions
of Batiraman crude oil. The asphaltene fraction of Batiraman crude oil was investigated
in our previous work (Yasar et al., 2009). Figure 8 shows that FTIR spectra of all
fractions revealed strong absorption near 2,920, 2,850, 1,455, 1,375, and 730 cm 1
because of the CH2 and CH3 groups. The presence of the bands at near 1,600 and
810 cm 1 in the spectra of aromatic, resin, and asphaltene fractions showed the proof of

Figure 4. 1 H-NMR spectrum of Batiraman asphaltene fraction.

 166 S. Akmaz et al.
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Figure 5. ESI-MS spectra of Batiraman saturate fraction.

the aromaticity. The saturate fraction has dominant aliphatic hyrdrocarbons as indicated
by the complete presence of absorbance near 2,920, 2,850, 1,450, 1,375, and 730 cm 1
and the absence of absorption near 1,600 cm 1 , which is the characteristic band for
aromaticity (Ali et al., 1989). CDO and C–O absorption bands are also evident in the
spectra at near 1,695–1,710 and 1,032 cm 1 and these bands appeared in the spectra of as-
phaltene, resin, and aromatic fractions. Ali et al. (1989) investigated functional groups of

Figure 6. ESI-MS spectra of Batiraman aromatic fraction.

 Structural Characterization of Batiraman Crude Oil 167
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Figure 7. ESI-MS spectra of Batiraman resin fraction.

Table 2
Distribution of carbon atoms of fractions of Batiraman crude oil
and average structural parameters

Parameter Asphaltene Saturate Aromatics Resin

CT (total carbon atoms per 67 31 19 65

molecule)
CS (total saturated carbon atoms 34 26 8 34
per molecule)
CSA (total saturated carbon atoms 9 <1 2 7
to an aromatic ring)
CA (total aromatic carbons per 33 5 8 24
molecule)
CP (peripheral carbon in a 11 <1 4 13
condensed aromatic sheet)
CI (internal carbon in a 22 2 4 11
condensed aromatic sheet)
CMy (total paraffinic methylene 13 20 5 27
carbon atoms per molecule)
CMe (total paraffinic methyl 3 6 3 7
carbon atoms per molecule)
CN (total naphthenic carbon 10 — 2 —
atoms per molecule)
RA (aromatic rings per molecule) 12 1 3 7
 168 S. Akmaz et al.
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Figure 8. Bands of FTIR spectra of Batiraman crude oil fractions.

Arabian heavy crude oil fractions using FTIR, which showed absorption near 2,900,
2,850, 1,470, and 1,390 cm 1 because of CH2 and CH3 groups; 1,620, 870, 817, and
750 cm 1 because of aromaticity; and 1,700 and 1,035 cm 1 because of CDO and C–O
groups. Aske et al. (2001) also determined the carbonyl peak at around 1,710 cm 1 . Ali
et al. (1989) concluded that the absorbance at 1,032 cm 1 may also be present because
of SDO groups. Peralta-Martinez et al. (2008) determined similar absorbtion bands for
FTIR spectra of fractions of Mexican vacuum residua. The FTIR spectra of Batiraman
crude oil fractions are similar to FTIR spectras of crude oil fractions investigated by Ali
et al. (1989), Peralta-Martinez et al. (2008), Aske et al. (2001), and Buenrostro-Gonzalez
(2001).
Combining structural analysis results obtained from elemental analysis, FTIR, 1 H
NMR, and ESI-MS of fractions, the possible hypothetical molecular structure for saturate,
aromatic, and resin fractions is represented as in Figures 9–11. The possible hypothetical
molecular structure for the asphaltene fraction (Figure 12) was proposed in our previous
work (Yasar et al., 2009).

Figure 9. Hypothetical structure for saturate fraction from Batiraman crude oil.
 Structural Characterization of Batiraman Crude Oil 169

Figure 10. Hypothetical structure for aromatic fraction from Batiraman crude oil.
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Figure 11. Hypothetical structure for resin fraction from Batiraman crude oil.

Figure 12. Hypothetical structure for asphaltene from Batiraman crude oil.
 170 S. Akmaz et al.

3. Conclusions
The high content of asphaltene and resin supported that Batiraman crude oil was a
heavy crude oil. 1 H-NMR, elemental analysis, and ESI-MS provided the determination
of structural parameters of fractions. FTIR spectra of fractions identified CDC, CDO,
CH2 , and CH3 groups. Hypothetical structures for four fractions were proposed. The
saturate fraction of Batiraman crude oil mostly contained long aliphatic compounds.
The aromatic fraction consisted of aromatic groups with aliphatic side chains. Resin
was composed of fused aromatic rings with branched paraffins and polar compounds.
Asphaltene was the most complex fraction. The present study has provided insight into
the chemical structure of Batiraman crude oil.
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Acknowledgments
This work was supported by the Research Fund of Istanbul University, Project No. 958.

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