Petroleum and Coal

Review Open Access

On the Importance of Mesophase State on Coke Structure

Alexandra Boytsova1, Sergey Strokin*1, Jorge Ancheyta2

1 Peter the Great St. Petersburg Polytechnic University, Polytechnicheskaya street 29, 195251, Saint
Petersburg, Russia
2 Instituto Mexicano del Petróleo, Eje Central Lázaro Cárdenas Norte 152, Col. San Bartolo Atepe-

huacan, México City 07730, México

Received May 27, 2020; Accepted August 6, 2020

Abstract
Different literature sources on the topic of carbon mesophases were reviewed and analyzed.
Information about structure of coke and mesophases, properties of basic structural units, mechanism
and chemistry of formation, industrial application and recent developments in carbon science was
discussed. It was found that the development of mesophase state of pitch determines the coke
structure.
Keywords: Carbon mesophase; Semi-coke; Coke structure; Liquid crystals.

1. Introduction
Carbon materials are widely used in modern life. They play an important role in various
industrial spheres, such as metallurgy, building, atomic power engineering, nanotechnology.
Delayed cokes of petroleum (petcoke) are used in production of carbon anodes, which are
central to the aluminum industry. Moderation of nuclear reactions is partially provided with
graphite rods. Carbon fibers are used as components for different products from sports equip-
ment to details of passenger jets. Unique physical, chemical and structural features of carbon
materials explain their popularity.
The main feedstocks for carbon materials manufacturing are pitches and cokes, which are
basically products of oil and coal refinery. The application of final product of coking absolutely
depends on the coke composition, which can be either isotropic or anisotropic. Structure type
is somehow determined by the ability of cokes to graphitize, or to form graphene layers situ-
ated parallel to each other. If the graphitization degree is low, the structural unit of coke is a
grain. Carbon grains with a size of up to 10 μm form isotropic structure (fine and medium-
grained coke). High-extent graphitization provides the formation of anisotropic needle cokes
with long thin grains (>60 μm length) [1].
The percentage of impurities, such as sulfur, in pitches and cokes used in production of
carbon materials, is proportional to the one found in parent oil. Impurities influence the quality
of resultant materials. High content of sulfur, for example, leads to corrosion of electrode pins,
premature cure of rubber and, what is vitally important, restrains the graphitization process.
It should be considered that petroleum industry has reached the stage where mining of heavy
sulfurous oils is quite common. Processing of heavy oils is troublesome and needs high capital
outlays, but due to depletion of light oil deposits new methods for heavy oil refining should be
developed [2]. This fact preconditions the importance of understanding of carbon structure
formation during carbonization processes.
Various research papers containing information about carbon structure have been reported
in the literature. Most of them concluded that coke texture strongly depends on mesophase
state of pitch development under heat treatment, and in this respect information about struc-
ture of mesophases, mechanism and chemistry of formation and some recent developments

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and examples of industrial application are presented. Then the aim of the present work is to
review the available information and discuss all of these aspects.
2. Theoretical aspects
2.1. Structure of mesophases
The process of formation of cokes with
anisotropic features incudes some im-
portant stages. When pitches, which are
optically isotropic, are heated, their soften-
ing and transmission to a liquid-like state is
observed [1]. As is normal for liquids, the
viscosity of the feedstocks rapidly de-
creases until the whole system suddenly so-
lidifies and forms a semi-coke that forms
graphite layers with interlayer spacing of
3.354 Å if the heat treatment temperature
is increased (Figure 1) [3].
Figure 1. Scheme of hexagonal unit cell of graphite [1]

The optical anisotropy of coke was described by various scientists who independently in-
vestigated polished surfaces of cokes and coke-like materials. Still, their developments did not
suggest any explanation for the process of formation of anisotropic structure which is a vital
aspect of carbon industry.
A tremendous contribution to understand
the formation of graphitizable carbons was
made by Brooks and Taylor [4]. They re-
searched the structure of coal and oil feed-
stocks on different stages of carbonization.
It was taken into account that substances
which form graphitizing carbons were
reached in polynuclear aromatic compounds.
The growth and appearance of spherical bod-
ies with dmin = 0,1 μm in the plastic carbo-
naceous material was reported (Figure 2).
The size of spheres increased until a three-
dimensional mosaic formation was reached,
that remained as solidified semi-coke.
Figure 2. Spheres at an intermediate stage of de-
velopment. The grey matrix is pitch-like material
Observations of spheres were done by
(P). The spheres are in random orientations. A few means of electron diffraction microscopy and
show almost total absorption of polarized light polarized light absorption. The described dif-
(arrowed). Reflected polarized light [4] fraction patterns observed on different sec-
tions of spheres (Figure 3) were not those
observed for crystalline materials but still indicated a considerable degree of order. After an-
alyzing the diffraction patterns the authors came to the conclusion that the kind of order
existed in spheres varied from lamellar (at the center) to radial (at the surface), as observed
in Figure 4. A response to surface tension forces seems to be due to spherical shape and the
surface tension effects can be seen as further evidence in the coalescence of two spheres, and
subsequently returning to spherical shape. A characteristic molecular orientation at their sur-
faces seems to be exhibited by the spheres, thus having many of liquid crystals characteristics [5].
The boundary condition seems to achieve in different spheres (small, large, and composite),
and at the pitch and mosaic mesophase interface, the surface with uniform molecular arrange-
ment, in which aromatic planes edges are perpendicular to interface.

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Figure 3. Variation in electron diffraction patterns over disk of sphere, oriented with lamellae parallel to
beam [4]

Single mesophase spheres prepared by

thin sectioning were studied by Augie et al.
by means of transmission electron micros-
copy [6]. The observed lattice fringes showed
a peculiar order of disk-like molecules, they
were stacked in long distorted columns, and
their optical diffraction pattern obtained with
a laser beam displayed a good parallelism of
the carbon layers (Figure 5). Such an organ-
ization of molecules is reminiscent of smectic
properties. When the spheres coalesce,
Figure 4. The model of mesophase suggested by
some disclinations are produced at the
Brooks and Taylor [4]
spheres’ boundaries. Also, the nematic order
destroys and replace the short-range pecu-
liar order [3]. So that, it can be stated that
mesophases have discotic, aromatic, ne-
matic properties with transient smectic be-
havior.
The formation of mesophase is neither a
process of crystallization, nor a precipitation
reaction, but it is a process of molecular self-
assembly, which is an important property of
macromolecules [7].
The polarity possessed in spherical
mesophases results from π-π interactions
between polynuclear aromatic type of mole-
cules which are recurring units of carbona-
ceous liquid crystals [8].
Figure 5. a) Transmission electron micrograph of
a thin section of a single mesophase sphere; b)
drawing of the thin area, showing columns [6]

2.2. Mechanism of mesophase formation

The initial stage of mesophase spheres formation is their nucleation owed to pitch volatiles
physical distillation with maximum molecular weight (MW) of 400 and the molecules thermal
polymerization in the range of 400-1100 MW. The average molecular weight (AMW) of the
isotropic phase is increased by both distillation and polymerization, which results in the initial

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development of long-range molecular order in the pitch. In the coalesced mesophase and
mesophase spheres, polymerization of the 400-1100 MW molecules causes a temporary in-
crease in the mesophase AMW. The transfer due to stirring and generated gas percolation of
similar size molecules from the isotropic phase reestablishes molecular equilibrium in
mesophase. The transfer of these smaller pitch molecules, which are unreacted original pitch
components, provokes the growth of mesophase spheres and coalesced mesophase. The lack
of reactivity of the largest molecules in the mesophase also contributes to the constant MW
distribution [8].
2.3. Coalescence
Coalescence of spheres leads to the formation of larger regions of extended order bulk
mesophases (Figures 6 and 7). Due to multiple acts of coalescence, the formation of bulk
mesophases is possible through the whole volume of a pitch sample. These margins possess
regions with almost constant parallel orientation of carbon layers. The larger the bulk
mesophases, the more graphitizable the semi-coke produced as a result of carbonization.
However, real pitch samples often contain insoluble impurities, which aggregate on the surface
of mesophases and might either modify the final coke structure or prevent individual
mesophases from coalescence. As a result, spheres adhere to each other and produce mul-
ticrystalline mesophase with different orientation of layers in individual regions. Obviously, a
single mesophase system is much more ordered than a multicrystalline one and its ability to
graphitize is higher.

Figure 7. Model of process of mesophase coales-

cence suggested by Brooks and Taylor [4]

Figure 6. Growth and coalescence of mesophases

into bulk mesophase system [8]

2.4. Properties of structural units

From the moment of mesophase nucleation the polymerization reactions occur in and be-
tween planes of mesogens, resulting in increasing of molecular weight of structural units [8].
The average molecular weight of mesophase components was calculated by Greinke during
the process of carbonization of residuum obtained from catalytic cracking of petroleum distil-
lates and residues. It was observed that molecules with molecular weight less than 400 dis-
tilled quickly. The content of components with MW of 1200 greatly increased, resulting in AMW
reaching the value of more than 800 (Figure 8).
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Figure 8. Molecular weight distributions obtained from Gel Permeation Chromatography curves of a pe-
troleum pitch as a function of heat treatment at 400°C [8]

Numerous researches were done to determine the type of chemical bonds formed by
polymerization of pitch molecules. Delhaes et al. [9] using diamagnetic susceptibility measure-
ments, have shown that the polymerized molecules in mesophase pitch do not possess too
highly condensed pitch monomers by single chemical bond. Later, application of depolymeri-
zation reaction of p-toluene-sulfonic acid to mesophases exhibited that chemical bonds in
polymerized and dimerized molecules were proposed by aryl-aryl bridges with smaller amount
of methylene bridges. Thermal cracking and gas formation studies of alkyl groups on aromatic
molecules with molecular weight higher than 400 have indicated that the side chains break at
the alpha position to the aromatic ring, which leads to aryl-aryl bridges formation in the pitch
dimers and not methylene bridges [8].
2.5. Chemistry of mesophase formation
Various analysis methods may be used to obtain enough information about the pitch com-
position, e.g. chromatographic analysis, mass spectrometry and nuclear magnetic resonance.
The abundance of chemical compounds of pitch might produce multiple chemical reactions, so
the complexity of composition of feedstocks is a stumbling block to understanding the chem-
istry of conversion of pitches to cokes. This is why observation of general properties of pitch
is more beneficial than specific molecular analysis [10].
The influence of asphaltenes on mesophase development was investigated by Eser and
Jenkins [11-12]. It was concluded that feedstocks asphaltene does not appear to be critically
important for the determination of mesophase development degree. However, the feedstocks
asphaltene fractions have a controlling influence in determining the mesophase development
degree during the feedstocks carbonization. The mesophase development degree during the
feedstock asphaltenes carbonization is dependent on the asphaltenes chemical constitution.
particularly, the asphaltenes hydrogen aromaticity seems to be a multifaceted parameter in
reflecting the structural differences among the asphaltenes, which are critically substantial for
the mesophase development. The mesophase development degree increased steadily with the
enhanced hydrogen aromaticity of the asphaltenes of various sources (residue from vacuum
distillation, bottoms from catalytic cracking, etc.)
By means of electron spin resonance, the presence of unpaired electrons in carbonizing
pitches was appointed, which probably indicates the formation of free radicals [13-14]. Free
radicals production is enhanced by alkyl, naphthenic, phenolic, carboxylic and other groups
and heteroatoms (sulfur, oxygen, nitrogen). Existence of free radicals increases the reactivity
of the mesophase systems, resulting in chemical reactions that lead to molecular growth in

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pitches in particular. The velocity of those reactions depends on reactivity of radicals. The
faster the polymerization reactions occur, the greater molecules appear at low temperatures,
which also increases the viscosity of the system. The resultant coke optical structure depends
directly on the rheological properties of the preceding mesophase [15]. Highly viscous
mesophases are unable to coalesce, and optical texture of resultant coke is smaller. Marsh
and Walker [10] made an important conclusion that it is difficult to determine the quantity of
compounds required to keep the balance between the carbonization rate, controlled by the
reactivity of components of carbonizing systems, and the viscosity of the resultant pitch.
Highly reactive and viscous pitches produce non-graphitizable semi-cokes and cause solidifi-
cation even before formation of mesophases. The polymerization reactions can be moderated
by hydrogen-donor molecules. Transferring hydrogen atoms to active free radicals stabilizes them
and allows to reach lower viscosity at higher temperatures, promoting graphitizability [16-19].
It was reported by Marsh et al. [20] that the rate of carbonization is connected with the
optical size of produced coke. Some volatile compounds remain in the system or transform
due to thermolysis, decreasing its viscosity and promoting the formation of cokes with large
optical texture.
The parameter of pressure affects the carbonization process. A closed system preventing
loss of volatile materials is created by the effect of a pressurized carbonization. The normally
lost material as volatiles in open systems is now preserved and its effect by reducing turbu-
lence and bubble formation, is to improve the resultant optical textures size. Such an effect
was reported when the applied gas pressure reached 150 bar. But higher pressures (300 bar)
provide the enhancement of viscosity and this prevents the coalescence of mesophase [21].
It was analyzed by Marsh and Latham [21] that pitch material can be basically separated
into three groups of components:
• Low molecular weight fraction, which decreases viscosity (solvent) and either becomes in-
corporated into mesophase or volatilizes
• Higher molecular weight fraction – the main material for pitch formation
• An insoluble in benzene and tetrahydrofuran fraction, which gives isotropic carbons when
carbonized separately
• The formation of quinoline-insoluble fraction during thermal processes was also considered.
By individual carbonizing of fractions a conclusion was made: low molecular weight fraction
not only provides physical fluidity of system, but also chemical stability. Its carbonization
result was coke with the largest optical texture which was even bigger than that one of carbon
produced from parent pitch. It also was noticed by Kakuta et al. [22] that the low aromaticity
saturate fraction produces a coke with a needle structure.
There exist a great variety of pitches with high content of impurities which can be converted
into carbons of low economical and industrial value, and production of such pitches is expand-
ing due to depletion of light oil deposits. However, most industrial spheres need to imply cokes
of high purity and long-flow anisotropy. Three main ways of improving the quality of the re-
sultant coke are:
1. To extract separate fractions and produce isotropic and anisotropic cokes from components
of one parent pitch
2. To add materials that up-grade the quality of the resultant coke
3. To modify the chemical composition by alkylation, hydrogenation etc.
The separation of parent feedstocks into benzene-soluble (BS) and benzene-insoluble frac-
tions (BI) an attempts for co-carbonization of blends of these fractions was reported in the
literature [23-26]. Certain fractions were also hydrogenated or alkylated and the resulting al-
kylated fractions were hydrogenated. They investigated the ability of blends of fractions to co-
carbonize in order to obtain needle-coke structure. The following conclusions were pointed
out:
1. Co-carbonization compatibility of solvent refined coal with benzene insoluble fractions were
significantly improved by hydrogenation, which give isotropic coke

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2. Co-carbonization compatibility of BS fractions is destroyed by alkylation, which suggests

that pitches poor compatibility could be associated with alkylation in constituent pitch mol-
ecules
3. The compatibility is restored by hydrogenation of the alkylated material
Impact of catalysts on carbonization process was observed by Mochida et al. [27] Their
experiment with carbonization of sulfur containing pitch in the presence of aluminum chloride
showed an improvement of optical structure.
Kumar and Srivastava [28] investigated the influence of transition metals, Co and Ni in
particular, on the mesophase formation. The time of thermal treatment to form mesophase
pitch was reported to be reduced due to acceleration of polymerization reactions. The addition
of Co and Ni salt catalysts improved the crystal assembly of mesophase.
A spinnable mesophase pitch could be produced from aromatic hydrocarbons by using
HF/BF3 as a condensation catalyst (Figure 9) [29].

Figure 9. Catalytic condensation of aromatic hydrocarbon with HF/BF 3 [29]

3. Industrial application
3.1. From theory to reality
Understanding the theoretical aspects of formation of carbon structure made a significant
impact on the industry of carbon and graphite. Scientifically reasonable methods of modera-
tion of different processes are now applied and new processes were also created.
Development of production of spinnable mesophase pitch from pure aromatic hydrocarbons
with the aid of HF/BF3 is one of the most tremendous achievement in studies of carbon
mesophase. Those pitches are spinned into carbon fibers with very high Young’s modulus and
thermal conductivity. Carbon fibers are used in construction technology, improving structural
stability due to[30]:
• High strength
• Stiffness
• Tensile and compressive strengths balance, and their very light weight
Consideration of mesophase formation is vital for modeling of processes of delayed coking [30].
The commercial value of green coke (graphitizable carbon produced as result of delayed cok-
ing) depends on the size of optical texture. There are two qualities of commercial green
coke[1]:
• Regular coke, with coarse-grained mosaics of 10 μm diameter or medium-flow anisotropy
with less than 30 μm length
• Needle coke, with acicular flow domain anisotropy of >60 μm length).

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The calcined regular cokes are the filler cokes in anode production for aluminum industry,
while needle cokes are filler cokes in manufacturing of high-performance graphite electrodes
for steel production.
Mesophase pitch is suitable as solid lubricant, which is employed for bearings and friction
parts working at severe conditions. MoS 2 and graphite are used dispersed in mineral oil and
grease as solid lubricants; but, graphite possesses unsatisfactory adhesion and malleability.
Mesophase pitch keeps its liquid state up to 450oC, that provides a graphitizable carbon film
on the metal surface at high yield. Blending of the mesophase pitch with graphite powder
improves lubrication. Mesophase pitch is also useful as a high temperature liquid lubricant
(300-400oC) [31].
Solvent fractioning of pitch matrix allows to separate the mesophase spherules or meso-
carbon microbeads (MCMB) [32]. These spherules are excellent raw material for high density
carbon materials, column-packing materials [33] and super-active carbon [34], while MCMB are
applied as Li-ion battery anode material [35].
3.2. Recent developments in studies of carbon mesophase materials
The rheological properties of mesophase pitch and coal mixtures were reported at temper-
atures up to 873 K. To observe the effect of coal particles on foaming and on the development
of pores in activated carbon discs (ACD) during carbonization, quench tests were conducted .
High coal-to-pitch ratios caused increases of the viscosity of the mixture under low-press [36]
ure foaming process, provoking two effects: limited growth of large bubbles and stronger
carbon monoliths. The highest strength ACD (56 ± 3 MPa compressive strength) was achieved
with a pitch-to-coal mass ratio of 1:2 (0.91g/cm3 bulk density and 579 ± 37 m2/g surface
area), whereby it was shown that the coal particles can stabilize bubble growth in an effective
way during the mesophase pitch foaming and carbonization. In addition, both the bubble
growth and ACD strength can be altered by adjusting the blend viscosity of pitch and coal with
the addition of coal to the blend. From these results, it is anticipated that the activated carbon
discs exhibit great potential for their application as gas storage and separation materials, since
they possess high strength and high volumetric adsorption capability.
A petroleum pitch of naphthenic nature was separated in three fraction by sequential ex-
traction with heptane and toluene[37]:
• Heptane-soluble (HS)
• Heptane insoluble/toluene-soluble (HITS)
• Toluene-insoluble (TI)
HITS resulted adequate and superior to HS and TI for the preparation of mesophase pitch
with the following characteristics:
• Large domain structure
• Low softening point
• High H/C molar ratio
• Carbon residue and ordered microcrystal structure
The results indicated the following behavior for the three components:
• HS, possessing rich alkyl chains, could enhance the carbonization by means of breaking of
chains at the beginning of the reaction
• HITS, having abundant naphthenic structures, was more prone to mitigate the carboniza-
tion via hydrogen transfer reaction during the aromatic molecules aggregation
• TI, as initial nucleus with small size, could initiate the mesophase spheres generation
The effect of asphaltenes in petroleum feeds (internally present and externally added) on
mesophase formation and structure of semi-coke was also reported in the literature [38]. The
results indicate that the increased asphaltenes content impacts on the semi-coke texture. For
instance, a feedstock with asphaltenes content of 10.44 wt% yielded flow-type coalescence,
while a feedstock with asphaltenes content of 24.57 wt%, resulted in a mosaic-type texture
in the pitch. When part of these asphaltenes was removed from the feedstock, the resulting
oil produced semi-cokes with large size mesophase domains.

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Boytsova et al. [39] investigated the gasification of asphaltenes from Yarega heavy oil under
different pressures in steam atmosphere. Two types of cokes were obtained as result of py-
rolysis. The first one had big pore size and crumble structure. The second one presented dense
spherical carbon particles with properties probably reminiscent of mesophases and signifi-
cantly lower content of impurities than that of parent crude oil.
Mesophase pitches from different petroleum were chemically activated to produce appro-
priate activated carbons to be used as electrodes in supercapacitors [40]. The effects of acti-
vating agent (NaOH, LiOH, and KOH), ratio of alkaline hydroxide-to-pitch, and temperature of
activation on the properties of the obtained activated carbons were the following:
• LiOH exhibited poor efficiency as activating agent.
• NaOH and KOH produced activated carbons with more suitable properties, that is high ap-
parent surface area and pore volume.
• The higher the KOH-to-pitch ratio the higher the chemical attack on the carbon.
• Increased KOH-to-pitch ratio produced higher burn offs and porosity development.
• Activation of petroleum pitch with 5:1 KOH-to-carbon ratio produced very high apparent
surface areas.
• The higher the activation temperature the higher the burn off, with minor differences as
compared with using different amounts of activating agent.
During the synthesis of carbon foams using an asphaltene pitch from Avgamasya in Turkey
as a carbon precursor, it was found that initial nitrogen pressure, foaming temperature, pres-
sure release time and inorganic content of the natural pitch affect in a considerable manner
the physical properties and microstructure of carbon foams. The asphaltite inorganic compo-
nents may act as filler, and thus be responsible of the enhancement of density and compres-
sive strength. The substantial increase in the compressive strength of asphaltite foams can be
then attributed to carbonization [41-42].
4. Perspectives on the study of mesophase formation
From the literature reports, it has been recognized that the carbonaceous mesophase plays
an important role as a precursor for manufacturing carbon fibers and other valuable materials.
The main definition of mesophase is that it is a high molecular weight planar aromatic com-
pound with considerable molecular order. Mesophase is a general term used to describe to
various intermediate phases which can be formed by the liquid crystalline materials.
Particularly, asphaltene fraction has been found to represent a high percentage of conver-
sion into mesophase, being the best precursor to produce mesophase the fraction of asphal-
tenes carbonized at 400°C.
It is also reported that carbonaceous mesophase appears during the thermal treatment of
crude oil in the range of 350 to 500°C as optically anisotropic spheres surrounded by an
isotropic liquid matrix. The onset of mesophase is of high interest in hydrogen addition pro-
cesses, because this phase can coalesce to form larger mesophase domains, which eventually
deposit as coke, thus producing reactor internals fouling.
Being asphaltenes closely related to mesophase, characterization of asphaltenes is very
useful to understand its mechanisms formation. But not only asphaltenes characterization is
important, but also the properties of asphaltenes fractions than can be divided by using dif-
ferent solver proportions (e.g. heptane and toluene). For instance, it has been reported that
the least soluble asphaltene fraction has more complex structures than other fractions, the
average number of carbons per alkyl side chain of the fractions is higher than that found in
unfractionated asphaltenes.
By thermal analysis of the two main polar components of a heavy crude oil, it was found
that asphaltenes formed 47wt% of coke during cracking reaction, while resins only 9 wt% of
coke, being wider the temperature range for resins to react as compared with that of asphal-
tenes. From this experimental results, it can be stated that asphaltenes contribute to the
generation of free radicals and that condensation reactions take please at high temperature.

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In summary, to get more insights on carbon mesophase mechanism formation, separation of

asphaltenes from crude oils, fractionation of the separated fractions, and their detailed char-
acterization is recommended.
5. Conclusion
From the analysis of the literature, the following conclusions can be pointed out:
• The development of mesophase state of carbon materials is a complex process that depends
on a variety of physical and chemical factors
• Understanding the stages of mesophase formation and the influence of temperature, pres-
sure and chemical composition is fundamental for choosing the feedstocks and methods of
processing in order to obtain carbons with certain structure
• Asphaltenes fraction is responsible for about 50 % of coke formation during cracking reaction
• Not only asphaltenes content but also asphaltenes properties are important to understand
the mechanisms of mesophase formation
• It has been recognized that fractionation of asphaltenes is also important to study to carry
out, since depending on the solubility the separated fractions they exhibit different struc-
tures that influence in different manner on mesophase formation
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To whom correspondence should be addressed: Sergey Strokin, Peter the Great St. Petersburg Polytechnic Uni-
versity, Polytechnicheskaya street 29, 195251, Saint Petersburg, Russia

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