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HUNGARIAN JOURNAL
OF INDUSTRY AND CHEMISTRY

VESZPRÉM
Vol. 40(1) pp. 25–31 (2012)

APPLICATION OF IMPROVED BIO-PARAFFINS IN DIESEL FUELS

T. KASZA1, CS. TÓTH2, J. HANCSÓK2

1MOL Hungarian Oil and Gas Plc., Százhalombatta, HUNGARY
2University of Pannonia, MOL Department of Hydrocarbon and Coal Processing, 10 Egyetem Str., Veszprém, HUNGARY

E-mail: hancsokj@almos.uni-pannon.hu

Bio-paraffin containing mixtures produced from different natural triglycerides (conventional and improved vegetable
oils, used cooking oils and fats, etc.) have high cetane number (95-105 units), but their freezing points are high (between
+15 and +32°C). This property can be improved by catalytic hydroisomerization. Products obtained over 0.5% Pt/SAPO-11
catalysts (T = 280–380°C; P = 20–80 bar; LHSV = 0.25–4.0 h-1; apparent contact time: between 1/3 and 4.0 h (at
LHSV = 3.0 h-1; H2/feedstock = 400 Nm

3/m3) had CFPP values of +5°C; -20°C and -32°C. At the same time, there was
decreased cetane number of the isomerates (87, 70 and 65 unit, respectively) relative to the feedstock. These biogasoils
are suitable for bio-components of premium quality diesel fuel or for the improvement of cetane number. They can also
reduce the density of low grade components providing some economic savings and some flexibility to refineries.

Keywords: biogasoils, biofuels, cetane number, cold flow properties

Introduction

The energy demand of the world is continuously
increasing because of the industrial development and
the population growth. Because of these and the
environmental advantages, the importance of different
bio fuels is significant nowadays [1–3] through the
energy policy of the European Union. Its aim is to
decrease the energy and oil dependency. To inspire the
utilization of bio fuels 2003/30/EC, and then 2009/28/EC
directives were created specifying the recommended
and compulsory share of bio-components in the
transportation fuels.

Currently, mainly the biodiesels (mixtures of methyl
esters) are used as Diesel fuel blending components,
which have numerous performance disadvantages; for
example, their oxidation and heat stability is poor
because of the great number of olefinic bonds [3–10].
Water content and the hydrolysis of ester bonds brings
about corrosion problems [3, 7, 8] resulting in poor
storage stability [3–6]. In addition, because of the good
conductivity, corrosion may damage the metallic parts.
Furthermore, the solving nature may cause
compatibility problems with plastic construction
materials [7–12]. Due to these disadvantages, the
maintenance costs are higher, and the lifetime of the
engine is shorter [10]. Because of the lower energy
content the fuel consumption is higher [9–13]. The
combustion characteristics differ from those of diesel
fuels (ignition delay, adiabatic flame temperature,
radiation heat loss, etc.), the NOx emission is higher
[9, 13–16], and the aldehyde emission is also higher
[13]. In addition, the cold filter plugging point is higher
[10, 15]. They have inadequate compatibility with

lubricating oils [10]. The after-treatment catalysts may
be damaged by alkali and/or alkaline earth metals and
phosphorus present in fatty oils [7]. The production costs
are also higher than for diesel fuels [6, 17, 18]. For these
reasons, car manufacturers recommend the blending
concentration of the fatty acid methyl esters by 7.0 v/v%
in the European Union in accordance with the EN
590:2009 standard. At the same time, up to 2020 the
European Union prescribed to use 10% of bio origin
components in fuels.

Accordingly, the production of fuels having a
preferable chemical structure from different triglyceride
containing feedstocks (e.g. oils of conventional and
ennobled plants, used frying oils and animal fats, algae
oils, fats from meat and leather industry, so called
brown grease from the sewage farms, etc.) has an
important role in reaching the purposes of the
mentioned directives [19].

A promising solution is the fuel purpose catalytic
hydrogenation of these triglycerides. The utilization of
these products is already supported by the CWA
15940:2009 standard. For this mainly sulfided transition
metal(s) (Ni, Co, Mo, W) containing catalysts having
high heteroatom removal activity are suggested [19–24].

During the catalytic hydrogenation of triglycerides,
mainly normal paraffins and some iso-paraffins generate
beside the formation of propane, carbon oxides (CO2,
CO), water, and oxygenic compounds according to
Figure 1 [19].

There are two main approaches to the hydrogenation
of triglycerides: co-processing or stand-alone catalytic
conversion. The co-processing systems require only
slight changes in the existing HDS units, which cost
only a few percent of refinery installation costs.

CH C

O R2

C
O

CH2 O R1

CH2 C

O R3

catalyst

H2, T, P
n-paraffins i-paraffins+

By-products: CO + CO2 + CH4 + C3H8 + H2O
+ oxygen containing products

Figure 1: General reaction scheme of the hydrogenation
of triglycerides

During the co-processing of gasoil – triglyceride

mixtures in a two-step process biogasoil containing
gasoils can be produced with improved cetane number
and suitable cold flow properties [20]. In the case of
stand-alone systems the investment costs are higher
compared to co-processing systems, but there is higher
control on the process and higher product quality can be
realized [21]. In this study biogasoils produced in such a
stand-alone system are considered. The stand-alone
produced, stabilized biogasoils have good heat and storage
stability and outstanding cetane number (95-105). But
their freezing points are high (between +15 and +32°C);
accordingly to their cold filter plugging points (CFPP),
they cannot satisfy either the summer grade
specification of the temperate zone (at most +5°C) or
the winter grade specifications (at most – 20°C).
Therefore their molecular structure has to be modified
in order to that the CFPP value fulfill the standard
specification.

For this purpose, the most suitable technology is the
isomerization as the freezing point of the branching
paraffins is lower by 20–40°C than that of the normal
paraffins having the same carbon number. To reach
favourable yields, high activity and selectivity catalysts
should be used. These kinds of catalysts can be the 10-
member-ring zeolites (e.g. ZSM-22, ZSM-23) and zeolite
analogues (SAPO-11, SAPO-31, SAPO-41) containing
different noble metals (Pt, Pd) [25–27].

During the hydroisomerization, the convenient
selection of the operational parameters is very important
because of the favourable yield and composition, as wel
as because of the disadvantageous effects on the catalyst
activity. Accordingly, the goal of our experiments was
the investigation of the effects of the process parameters
(temperature: 280–400°C, pressure: 5–80 bar, liquid
hourly space velocity (LHSV): 0.5-4.0 h-1, H2/
hydrocarbon ratio: 200–800 Nm3/m3) on the yield and
product quality during the isomerization of normal
paraffin mixture produced from sunflower oil.
Furthermore, we compared the performance properties
of the produced biogasoils with those of fossil gasoils.

Experimental Section

Apparatus

The experiments were carried out in an apparatus
containing a tubular down-flow reactor of 100 cm3
effective volume. It contains all the equipment and

devices applied in the reactor system of an industrial
heterogeneous catalytic plant [3]. The experiments were
carried out in continuous operation with steady-state
activity catalyst.

Materials

During our heterogenic catalytic experiments, a normal
paraffin mixture (CFPP = 23°C; hydrocarbons: C17-:
6.3%, i-C17: 0.3%, n-C17: 46.7%, i-C18: 0.4%, n-C18:
43.3%, C19+: 2.0%, content of oxygenic compounds:
0.06%, oxygen content : 68 mg/kg) produced with high
yield (84.8%; which is relatively high regarding the
theoretically highest yield, which is about 86.2% in the
case of sunflower oil, which could change as a function of
the oleic acid composition of the used triglyceride) from
Hungarian sunflower oil over commercial hydrotreating
NiMo/Al2O3 catalysts was used as a base feedstock. The
0.5% Pt/SAPO-11 catalyst was prepared as described
and characterized according to HU 225 912 patent.

Methods

The properties of the feedstock and the products were
analyzed according to EU and ASTM standards and GC
(Shimadzu 2010 GC) and GC-MS (HP 6980A). The
oxygen content of the feedstock and products was
determined by CHNS/O analysis.

The crystal structure of the catalyst and its change
during the experiments were determined by X-ray
diffraction (XRD). XRD data were collected by
Siemens D500 equipment, Philips PW 1730/10 (PW
1050/70 goniometer) diffractometer, CuKα (40 kV,
35 mA) ray were applied. The XRD characterization of
the obtained powder confirmed that it was SAPO-11.
The synthesized SAPO-11 microporous molecular sieve
was impregnated with Pt(NH3)4Cl2 solution. The
platinum content was determined according to the UOP-
274 standard. The platinum dispersion was determined
by H2 chemisorption [29], which was 91%. The surface
properties of the catalyst were determined by ASAP
2000 equipment (Micromeritics) (pore range of 1.7–300 nm)
and mercury penetration method using CARLO-ERBA
equipment (pore range 7.5–15000 nm). The specific
surface area of the catalyst was 100.1 m2/g. The acidity
was determined by ammonium adsorption, which was
0.66 mmol NH3/g. Prior to the activity measurements
the catalysts were pre-treated in situ, as described in our
earlier publication [3].

Results and Discussion

The experiments were carried out in a wide range of
process parameters (T = 280–380°C; P = 20–80 bar;
LHSV = 0.25–4.0 h-1; apparent contact time: between 1/3
and 4.0 h (at LHSV = 3.0 h-1). Our aim was to find a
combination where the liquid yield is at least 90%
similarly to the industrially required yield. It is

necessary to avoid the fast deactivation because of the
significant cracking and industrially at least 90–95%
liquid yield is required. According to our pre-
experiments using practically heteroatom free (lower
than 10 mgS/kg) feedstocks, it was concluded that the
increase of the platinum content increased the isoparaffin
content of the products significantly up to 0.5%. It was
because the increase of the number of the hydrogenation-
dehydrogenation active sites promoted the isomerization
reactions and the prompt hydrogenation of the
intermediate carbenium ions as a consequence inhibited
their cracking. The further increase of the platinum
content had only insignificant effects [30, 31].
Consequently, the platinum content of the applied
Pt/SAPO-11 was 0.5%.

Product yield and composition

During the systematic isomerization of the practically
heteroatom-free normal paraffin mixture, the products
were separated to gas and liquid phases. The gas
products taken from the top of the separator contained
mainly hydrogen and light hydrocarbons generated in
the hydrocracking reactions. These hydrocarbons were
mainly normal and isobutane (higher than 40% of the
light hydrocarbons) which could be used in the oil
industry for several purposes (e.g. LPG production,
alkylation of i-C4 with olefins, dehydrogenation of i-C4
to isobutylene, etc.) [32]. The target product contained
the C11 and heavier hydrocarbons beside which C5-C10
valuable side products were also generated in a small
quantity.

The yield of the target products decreased by
increasing the temperature; this effect was intensified by
decreasing the LHSV (Figure 2). The reason of this was
that the chain breaking of the unstable carbenium ions
could happen easily at higher temperature on the
catalyst surface; furthermore, the lower the flow rate of
the molecule was the higher the contact time was and
the higher the possibility of the cracking was.

100

270 290 310 330 350 370 390 410

P
ro

du
ct

y
ie

ld
, %

Temperature, °C

LSHV = 0.5 1/h
LSHV = 0.75 1/h
LSHV = 1.0 1/h
LSHV = 2.0 1/h
LSHV = 4.0 1/h

Figure 2: Product yields as a function of the

temperature and the LHSV
(P = 40 bar, H2/feedstock ratio = 400 Nm3/m3)

The yield of the products decreased by decreasing

the pressure in the investigated pressure range
(20–80 bar) because the partial pressure of the
hydrocarbons increased resulting in a lower degree of
hydrogenation of the instable carbenium ions, thus

increasing the possibility of the cracking. The product
yield also decreased by decreasing the hydrogen/
hydrocarbon ratio similarly to the decrease of the total
pressure, because of the rising cracking. It was
especially dominant below 400 Nm3/m3.

Increasing the contact time by reacting again and
again the paraffin rich mixture at 360°C, 40 bar, and
LHSV of 3.0 h-1, (where the cracking selectivity is
relatively low) the yield continuously decreased, since
more and more polybranched paraffins were generated
(see Figure 6), which are more susceptible to cracking
than normal and monobranched paraffins.

The isoparaffin content of the product increased
significantly above 300°C by increasing the temperature,
but it started to decrease at about 360°C partly because
of the thermodynamic inhibition (as the isomerization
reactions are exothermic), partly because of the better
approach of the thermodynamic equilibrium, and partly
because of the cracking reactions (Figure 3).

0
10
20
30
40
50
60
70
80
90

270 290 310 330 350 370 390 410

Is
op

ar
af

fi
n

co
nt

en
t,

Temperature, °C

LSHV = 0.5 1/h
LSHV = 0.75 1/h
LSHV = 1.0 1/h
LSHV = 2.0 1/h
LSHV = 4.0 1/h

Figure 3: The isoparaffin content of the products as a

function of the temperature and LSHV
(P = 40 bars, H2/feedstock ratio = 400 Nm3/m3)

Up to about 360°C, mainly (>85%) mono branched

paraffins were generated, whose significant part (>98%)
was mono-methyl-paraffins. It was because, in the case
of the 10-member ring zeolites, only a small amount of
isoparaffins having alkyl chain of more than one carbon
number can form due to the steric inhibition [33]. Their
freezing points are more favourable than those of the
normal paraffins, and their cetane number is high enough
(Figure 4).

100

120

4 6 8 10 12 14 16 18 20 22 24

C
et

an
e

nu
m

be
r

Carbon number

n-paraffins

mono-branched paraffins

multi-branched paraffins

Figure 4: Cetane number of the paraffins as a function

of the carbon number [34]

However, above 360°C a significant amount (15–35%)

of multi-branched paraffins formed, which also have
favourable cold flow properties, but their cetane number

is low (e.g. 2,2,4,4,6,8,8-heptamethylnonane: freezing
point: 0°C, cetane number: 15 unit). This effect was
increased by decreasing the LHSV (Fig. 3).

Up to 340°C, the concentration of isoparaffins
increased by decreasing the pressure to 20 bar, because
by decreasing the hydrogen pressure the conversion of
hydrocarbons could be increased. But above 360°C the
increase of the pressure to 50 bar was favourable,
because the partial pressure of the hydrogen could roll
back the cracking reactions (Figure 5).

0 10 20 30 40 50 60 70 80 90

Is
op

ar
af

fi
n

co
nt

en
t,

Pressure, bar

320°C 340°C 360°C 380°C 400°C

Figure 5: The isoparaffin content of the products as a

function of the pressure and the temperature
(LHSV = 1.0 h-1, H2/feedstock ratio = 400 Nm3/m3)

At 360°C, which was favourable regarding both the

yield and the isoparaffins content, at least 400 Nm3/m3
H2/feedstock volume ratio was necessary to reach a high
isoparaffin content. In the case of lower values, the
concentration of the isoparaffins was decreased by the
hydrocracking reactions.

Increasing the apparent contact time (number of runs
multiplied by 1/LHSV), the isoparaffin content of the
product continuously increased by reacting again and
again the paraffin rich mixture in the reactor (at 360°C,
40 bar and LHSV of 3.0 h-1). At the apparent contact
time of 2.0 h [= 6 x 1/(3.0 h-1)] the isoparaffin content
exceeded 90%. Further increase of the conversion
increased only the concentration of polybranched
paraffins (Fig. 6).

9.77

7.10

4.25

3.18
2.64 2.38

2.06 1.85 1.56 1.41 1.29 1.21

100

0.33 0.67 1.00 1.33 1.67 2.00 2.33 2.67 3.00 3.33 3.67 4.00

Is
op

ar
af

fin
c

on
te

nt
o

f t
he

p
ro

du
ct

, %

Apparent contact time, h

Concentration of monobranched paraffins, %
Concentration fo polybranched paraffins, %
Ratio of mono/polybranched paraffins

Figure 6: The mono- and polybranched isoparaffin in
the products as a function of the apparent contact time

Performance properties

The cold filter plugging point (CFPP) of the products
having gasoil boiling range decreased by increasing the

concentration of the isoparaffins. At relatively low
conversion of n-paraffins (<30%), the CFPP decreased
only some units (Figure 7). It was because the resolvent
effect of isoparaffins could not inhibit the formation and
growing of n-paraffin crystals. At higher conversion,
not only the higher isoparaffin concentration improved
the value of CFPP, but the formation of lower carbon
number molecules generating mainly at higher than
70% of conversion by the cracking of polybranched
paraffins. Accordingly, the CFPP value of the products
can satisfy not only the winter specification of the
temperature zone, but the specification valid in the
arctic zone (-20°C; -26°C; -32°C and -38°C) as well.

-50

-40

-30

-20

-10

100

110

0 10 20 30 40 50 60 70 80 90 100

C
ol

d
fi

lt
er

p
lu

gg
in

g
po

in
t,

°
C

C
et

an
e

nu
m

be
r

Conversion of n-paraffins, %

Cetane number

Cold filter plugging point, °C

Figure 7: The cold filter plugging point and the cetane
number of the products as a function of the n-paraffin

conversion
(T = 360°C; P = 40 bar; H2/feedstock ratio = 400 Nm3/m3)

The cetane number of the products decreased as a

function of the conversion (Fig. 7) relative to that of the
feedstock (101 unit), as the mono-methyl paraffins and
polybranched paraffins have lower cetane numbers
(60–75 and 40–65 unit, respectively) than those of the
normal paraffins (90–110 unit) [34]. The cetane numbers
of the products having improved cold flow properties
(satisfying at least the summer grade specification) were
between 65-86 unit, which is significantly higher than
the specified value (51 unit) of the current Diesel fuel
standard (EN 590:2009 + A1:2010).

While the viscosity of the obtained biogasoils was in
the range of 2.5–3.5 mm2/s meeting the specification,
the density could not provide direct blending as it was in
the range of 0.772–0.782 g/cm3 underachieving the
expected 0.820 g/cm3 (Figure 8).

0,764

0,766

0,768

0,770

0,772

0,774

0,776

0,778

0,780

0,782

0,784

2,0

2,5

3,0

3,5

4,0

4,5

0 20 40 60 80 100

D
en

si
ty

, g
/c

m
3

K
in

em
at

ic
v

is
co

si
ty

,
m

m
2 /

Conversion of n-paraffins, %

Viscosity (40°C)
Density (40°C)

Figure 8: The viscosity and density of the products as a

function of the n-paraffin conversion
(T = 360°C; P = 40 bar; H2/feedstock ratio = 400 Nm3/m3)

Utilization possibilities of biogasoils

Since biogasoils consist of purely normal and isoparaffins,
they have more preferable chemical structures than
biodiesels. Accordingly, they can eliminate the above
disadvantages having an important role in reaching the
purposes of the mentioned directives.

Furthermore, these products are excellent Diesel fuel
blending components, as they are practically free of
sulfur and aromatic compounds, and burn exceptionally
clearly. Accordingly, biogasoils can be used for premium
quality diesel fuels or using these low density products
could provide some economic savings and some
flexibility for crude refineries in case of blending of
gasoils having high aromatic content and low cetane
number.

We note that during the production of these
improved products the yield decreases. Furthermore, the
usability of isoparaffin rich Jet and gasoline fractions
has to be considered as well.

Biogasoils as blending components of premium quality
diesel fuels

Regarding the production costs, the feedstock price
(Figure 9) of biogasoils, which is the most significant
cost of bio-fuels, can be lower than that of biodiesels
since (as it was mentioned) they can be produced from a
broader base of feedstock. On the other hand, the
installation cost of a biogasoil plant can be higher than
that of a biodiesel plant because of the relatively high
price of the hydrogenation catalysts and the pressurized
equipment. Regarding the operational costs, the hydrogen
consumption represents one of the highest items in the
case of biogasoils. However, because of the high
exothermic nature of the hydrogenation reactions,
biogasoil production has a net steam production
capability, which can be utilized effectively in a
refinery. To sum it up, biogasoils can be competitive
with biodiesels regarding only the costs, while they
excel those performance properties.

200

400

600

800

1000

1200

1400

1600

1800

2000

M
on

fl
y

pr
ic

e
of

v
eg

et
ab

le
o

ils
, $

/m
3

Sunflower oil
Rapeseed oil
Palm oil
Soybean oil

Figure 9: The monthly price of vegetable oils [35]

Comparing only the current product price of

biogasoils with that of low sulphur diesel gasoils
(950-1050 $/t), biogasoils can hardly compete because of

the high feedstock price (800–1400 $/m3 ≈ 850–1450 $/t).
Considering the performance properties as well, the
competitiveness of biogasoils seems to be more
favorable, since the production of gasoils with CFPP
value of -20°C or lower can be realized with some yield
loss and significant extra costs. In addition to the
production of gasoils with biodiesel content, the CFPP
value can be a further challenge (CFPP of biodiesels is
in the range of -5°C and +5°C depending on the
feedstock) [6]. Consequently, a high amount of
additives has to be used. On the other hand, biogasoils
having low density and excellent cold flow properties
may have a positive effect on the cold flow properties of
gasoils, therefore, they might improve the economy of
premium gasoil production.

Biogasoils used for quality improvement of gasoils
having low cetane number and high density

In order to increase the profitability refineries try to
increase the distillate yield, especially the diesel yield.
Some of the easier options are that the refineries can
consider crude selection, cut points, operating modes,
and catalysts. For further distillate yield improvement,
such technologies should be used that break or crack
larger, higher boiling point components into smaller,
lower boiling point components. These options require
capital investment and higher operating costs [36, 37].

As an alternative option, many European refineries
try to change the FCC unit for increased distillate
production using new catalyst formulations with better
cracking capabilities [37]. However, the blending of
light cycle oil (LCO) having gasoil boiling range into
diesel pool requires further processing as it generally
has a high aromatic content (65–75%), low cetane
number (15–25), and a relatively high sulfur content
(100–1000 mg/kg). During the processing of relatively
low value (650–700 $/t) LCO, the hydrogen consumption
is significant (20–25 kg/t); the cetane number can be
improved reasonably up to about 30–35 unit. In the case
of biogasoil production, hydrogen consumption is
similar, approximately 20–25 kg/t as a function of the
feedstock composition, but the cetane number is in the
range of 65–86 unit.

Experiments showed that during the blending of
biogasoils into gasoils the physical-chemical properties
and the cetane number change almost linearly as a
function of the biogasoil content in the gasoil [38].
These data correlated well with our results. We used
an obtained biogasoil product (CFPP = -12°C; cetane
number: 74.3) and a conventional light cyclic oil. The
main properties of the blended mixture are
summarized in Table 1.

As the data of Table 1 show different blends
obtained by the admixture of a low density, high cetane
number biogasoil and a high density, low cetane number
light cyclic oil meets the specification of the diesel
standard.

Table. 1. Main properties and the estimated production cost of mixtures of a biogasoil and a light cyclic oil

Biogasoil and light cyclic oil mixtures
Property Biogasoil

80:20 60:40 50:50 40:60 20:80
Hydrotreated

LCO

Density, g/cm3 0.777 0.808 0.838 0.854 0.869 0.899 0.930
Cetane number 74.3 65.8 57.3 53.1 48.9 40.4 32.0

CFPP, °C -12 -9 -6 -4 -3 0 3
Production cost, $/t 1500 1350 1200 1125 1050 900 750

The CFPP value of the obtained mixture was more

favourable than that of the LCO. Accordingly, the
quality of the LCO improved with biogasoil can be a
suitable gasoil blending component. Mixtures containing
40-60% biogasoil as a blending component have a
production cost – depending on the price of the
feedstock – competitive with the production cost of
diesel fuels.

Conclusion

The 0.5%Pt/SAPO-11 catalyst is suitable for the
isomerization of normal paraffin-rich mixtures produced
from natural triglycerides in order to improve the cold
flow properties. The products have outstanding cetane
number and are excellent Diesel fuel blending
components, as they are practically free of sulphur and
aromatic compounds, and burn exceptionally clearly.

Accordingly, they are suitable for bio-components of
premium quality diesel fuel. Using these biogasoils for
the improvement of cetane number and the reductions in
density could provide some economic savings and some
flexibility to refineries (e.g. economical application of
light cyclic oil of FCC units).

Acknowledgement

This work was supported by the European Union and
co-financed by the European Social Fund in the frame
of the TÁMOP-4.2.1/B-09/1/KONV-2010-0003 and
TÁMOP-4.2.2/B-10/1-2010-0025 projects.

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