Microsoft Word - A_57_Kasza_R.doc

HUNGARIAN JOURNAL
OF INDUSTRIAL CHEMISTRY

VESZPRÉM
Vol. 39(1) pp. 121-126 (2011)

INVESTIGATION OF FUEL COMPONENTS PRODUCED BY THE
ISOMERIZATION OF BIO-PARAFFIN MIXTURES

T. KASZA, J. HANCSÓK

University of Pannonia, MOL Department of Hydrocarbon and Coal Processing, HUNGARY
E-mail: hancsokj@almos.uni-pannon.hu

The importance of biofuels becomes more acute, especially in the European Union. Beside them, the biogasoil is a promising
product that is a fuel with high isoparaffin content in the gas oil boiling range, which can be produced by the catalytic
hydrogenation of different natural triglycerides. In order to improve the cold flow properties of mixtures consist of mainly
normal paraffins they have to be isomerized. In this paper the isomerization of paraffin mixture consists of only normal
and iso-paraffin was studied on 0.5% Pt/SAPO-11 catalyst at 300–380 °C temperature, 40 bar pressure, 0.5–4.0 h-1 of
liquid space velocity and 400 Nm3/m3 of H2/feed ratio. It was found that CFPP value of the products can be tailored
between -7 °C and -15 °C at a gas oil yield of 85–95%. During the conversion 2–5% of bio-jet fuel was obtained with
CFPP value of between -55 °C and -45 °C. Bio-naphtha also formed with a yield of 2–5.5%, which can be used as a
feedstock of naphtha isomerization. All of the products are free of aromatics, sulphur and nitrogen content, so they are
environmentally sound blending component.

Keywords: biogasoil, bio-jet fuel, bio-naphtha, isomerization, Pt/SAPO-11

Introduction

In the last decade, the express population growth of the
world and the increase of the living standard in the
developing countries have increased significantly the
energy demand of the World. Besides, the demand of
fuels has constantly extended. In the developed
countries of the World environmental regulations were
made to protect the environment and to stimulate the
economy. Because of these effects and environmental
advantages the role of bio-fuels has become more and
more important [1-5]. Bio-fuels are materials which are
suitable for carrying energy and drive engines, and are
produced by different ways from different biomass such
as agricultural products and/or wastes.

Because of the several disadvantages of the currently
used bio-fuels and those production technologies and of
the different demands and incentives the research,
development and market introduction of second or new
generation bio-fuels came into front in European Union
[6-8], USA [9] and on other part of the world [10].
Accordingly products of different composition have to
be produced.

Because of these in the last few years intensive
research-development activity started in the field of
production and utilization of Diesel fuels produced from
natural triglycerides via thermal or mainly catalytic
processes. Beside these bio-fuels one of the most
promising one is the so-called biogasoil, which can be
produced from natural triglycerides by catalytic
hydrogenation (Fig. 1) [11-15].

Figure 1: Reaction scheme of the biogasoil production

During the catalytic hydrogenation – as a function of

the catalyst and process parameters – normal paraffins
form which carbon number is the same or shorter by one
than that of the carbon number of the fatty acid of the
triglyceride [13, 16]. The concentration of iso-paraffins
– as a function of the catalyst and process parameters –
generally do not exceed 30%; often less than 10% [13].
The concentration of the intermediate oxygenic
compounds (e.g. mono and diglycerides, carboxyl acids,
esters, etc.) is often below 0.5% over the high activity
heteroatom removal catalysts [14].

As a feedstock of biogasoils not only soy, palm,
coconut, rapeseed and sunflower oils are suitable (which
are cultivated currently in large quantities for biodiesel
production), but the waste triglycerides such as used
cooking oils, waste animal fats, greases from meat and
leather processing industry, brown greases of sewage
farms, saturated fatty acids of palm oil production, as

122

well. In the last few years, in order to broad the feedstock
supply the cultivation of such oil plants started which
can subsist on unarable lands or salt water coasts, as
well (jatropha, mahua, karanja, neem, jupati [17-19]).
Furthermore the production of algae and fungal oils are
intensively researched, as well [19-23].

The second step of the biogasoil production is the
isomerization of paraffin rich mixture to improve the
cold flow properties. During this process branched
hydrocarbons form from linear paraffins, which freezing
point is lower by 20–30 °C than that of the convenient
normal paraffins (Fig. 2), while their cetane number is
still higher than it is specified in the current Diesel
standard (Fig. 3) [24].

-10 -5

18
28

-46

-26

-10

6
18

-70 -69

-31
-20

-7

-100

-80

-60

-40

-20

Carbon number

F
re

ez
in

g
po

in
t,°

normal paraffin
2-methyl-paraffin
5-methyl-paraffin

1312 16 18 20

Figure 2: Freezing point of some iso and normal
paraffin as a function of the carbon number

100

120

5 10 15 20 25

C
et

an
e

nu
m

be
r

Carbon number

Paraffins

Olefins Isoparaffins

Mono-ring
aromatics

Mono-ring
naphthenes

Decalines

Naphthalines

Tetralines

Figure 3: Cetane number of different hydrocarbons as a

function of carbon number

During the catalytic hydroisomerization hydro-
cracking reactions also take place in different measure
as a function of the applied catalyst and process
parameters. During these reactions smaller molecule
mass hydrocarbons form which have different number
of branching. In the research field of isomerization of
bioparaffins only a few research paper were published.
These have not discussed the yield of the products and
those performance properties in detail and with academic
depth.

Accordingly the aim of our present contribution was
the conversion of hydrocarbon mixture produced from
sunflower oil in order to be suitable to use in Diesel

engines as fuel or blending component. During this we
investigated the change of yield and composition of the
product over Pt/SAPO-11 catalyst found to be favourable
in our pre-experiments.

Experimental

During the experiments the process temperature was
varied between 300 and 380 °C, while liquid hourly
space velocity (LHSV) was changed between 0.5 and
4.0 h-1. The process pressure was 40 bar which was
found to be favourable in our experiments over 0.5%
Pt/SAPO-11 catalyst [11, 15]. Applying lower pressure
resulted loss of yield and catalyst deactivation because
of the intensifying cracking reactions, while the use of
higher pressure did not have further beneficial effect on
the product yield and composition.

The value of the H2/feedstock ratio was unchanged;
it was 400 Nm3/m3. During our pre-experiments it was
found that the utilization of lower amount of hydrogen
causes the increase of the cracking reactions which led
to the decrease of the isoparaffin content of the product.
The utilization of higher amount of hydrogen/feedstock
ratio – higher than 400 Nm3/m3 – is unfavourable
regarding economical aspects; moreover it could retard
the degree of the isomerization [11, 15].

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 [13]. The experiments were
carried out in continuous operation with steady-state
activity catalyst.

Materials and methods

Table 1 contains the properties of paraffin mixture
produced from sunflower oil used as feedstock. The
properties of the feedstock and the products were
determined according to the test methods specified in
EN 590:2009 Diesel fuel standard. The hydrocarbon
composition was measured by Shimadzu 2010 GC using
Zebron DB-1HT (30 m x 0.32 mm x 0.1 μm) column.

The catalysts were prepared as described and
characterized according to HU 225 912 patent. The
crystal structure and the purity of the catalyst were
determined by X-ray diffraction (XRD). 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 of the catalyst was
determined according to UOP-274 standard.

123

Table 1: The main properties of the feedstock

Properties Value
Density at 40°C, g/cm3 0.7697
Kinematical viscosity, 40°C, mm2/s 3.714
Cold filter plugging point, °C +23
Flash point, °C 50
Sulphur content, mg/kg 3.4
Nitrogen content, mg/kg 2.3
Acid number, mg KOH/g 1.9
Iodine number, g I2/g <1

C17- 7.0
n-C17 46.8
i-C17 0.8
n-C18 42.9
i-C18 0.9

Paraffin content, %

C18+ 1.7

The dispersity of the platinum was determined by H2

chemisorption, which was 91%. The BET surface area of
the catalyst was 100.1 m2/g. The acidity of the catalyst
determined by NH3 adsorption was 0.66 mmol NH3/g.
Prior to activity measurements the catalysts were pretreated
in situ, as described in our earlier publication [11].

Results and discussion

The products obtained during the isomerization of the
paraffin rich feedstock were the mixtures of liquid and gas
phase hydrocarbons. The gas products were generated
by the hydrocracking side reactions. They contained
mainly butane and isobutane (more than 40% of the gas
phase). These can be used for several purposes in a
refinery e.g. LPG production, alkylation of i-C4 with
olefins, dehydrogenation of i-C4 to isobutylene, etc.

The liquid products were the mixtures of iso and
normal paraffins. These were separated by distillation to
gasoline (C5-C9 hydrocarbons; B.P.: 40–160 °C) and jet
fuel fraction (C10-C13 hydrocarbons; B.P.: 160–240 °C)
as valuable side product and to the gas oil boiling range
(C14-C22 hydrocarbons; B.P.: 240–360 °C) main product.

The yields of products

The yield of the liquid product mixtures decreased by
increase of the level of the conversion (by increasing the
temperature and by decreasing the LHSV) (Fig. 4). The
reason of this was that the carbenium ions generated on
the surface of the catalyst during the isomerization,
having lower stability than that of the saturated
hydrocarbons, could be cracked more easily at higher
temperature [25]. In the investigated process parameter
range, the yield of the product exceeded 85% in every
case.

100

310 320 330 340 350 360 370 380 390

L
iq

ui
d

pr
od

uc
t

yi
el

d,
%

Temperature, °C

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

Figure 4: Product yields as a function of temperature
and LHSV (P = 40 bar; H2/HC ratio = 400 Nm

3/m3)

The composition of the products

By increase the temperature up to about 360 °C the
isoparaffin content of the products increased significantly,
namely the degree of isomerization increased. However,
at about 360 °C it reached a maximum, and then started
to decrease. It was partly because of the thermodynamic
inhibition (namely the isomerization is an exothermic
reaction) and partly because of the increase of the cracking
reactions (Fig. 5). Cracking reactions not only decreased
the yield of isoparaffins, but caused coke formation, that
decreased the activity of catalyst, as well.

300 310 320 330 340 350 360 370 380 390

Is
op

ar
af

fi
n

co
nt

en
t,

Temperature, °C

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

Figure 5: Isoparaffin content of the products as a

function of temperature and LHSV
(P = 40 bar; H2/HC ratio = 400 Nm

3/m3)

The carbon number based fraction distribution and

the faction composition of some products are given in
Fig. 6. It presents well that the share of C14-C19+ fractions
decreased while that of C3-C13 fractions increased by the
increase of the conversion. Methane and ethane were
not found in gas products. It suggested that cracking of
hydrocarbons occurred by beta cracking, wherein
cracked products having at least three carbon number
(Table 2) [25]. The distribution of cracked products was
not similar to that of the theoretical, modal cracked
product distribution, it was shifted toward to lighter
hydrocarbons. It indicated that the secondary cracking
of long chain hydrocarbons took place as well.

124

Figure 6: Hydrocarbon composition of the feedstock and products obtained at LHSV of 4.0, 2.0 and 0.75 h-1

respectively (Upper number in the bubble is isoparaffin content of the given carbon number fraction; while lower
value is the ratio of mono and multibranched isoparaffins of the given carbon number fraction;

T = 360 °C; P = 40 bar; H2/HC ratio = 400 Nm
3/m3); * - can not be measured, or no such a compound.

Table 2: Five types of β-cracking

Type NCAmin Example

A ≥8

B1 ≥7

B2 ≥7

C ≥6

D ≥5

NCAmin: Minimal carbon number of carbenium ion

The isoparaffin content and the ratio of mono/multi

branched paraffins of the different fractions obtained at
LHSV of 0.75 h-1 are presented in Fig 6. It can be seen
well that concentration of isoparaffins formed from the
dominant fractions (n-C15 – n-C18) and the ratio of
mono/multi branched paraffins were significantly higher
than those of the lower molecule weight hydrocarbons.

The reason of these effects was the special pore
structure of Pt/SAPO-11 catalyst. Namely, during the
isomerization of paraffins over SAPO-11 catalyst, mainly
mono and multi branched methyl paraffins form. Their
cracking could happen via C and D type beta cracking
(Table 2), because between the branchings of these
multibranced paraffins have at least 3 or 4 carbon number
distance [25]. Accordingly during the cracking of mono-

methyl paraffins two normal paraffins form, while from
dibranched paraffins a normal and an isoparaffin generate.

Investigation of the performance properties

The cold filter plugging point (CFPP) of diesel fuels is an
importance performance property, because at decreased
temperature the precipitated paraffin crystals can cause
operational disorders or unserviceability of the fuel
supply system.

The CFPP values of the products decreased by the
increase of the temperature and the decrease of the LHSV.
Its reason was mainly the increase of the isoparaffin
content of the products. The lower molecule weight
compound formed in the cracking reactions also improved
the CFPP value, as they have lower freezing point.
Accordingly, at the favourable operational parameters
(T = 360 °C, p = 40 bar, LHSV = 0.75–1.0 h-1 and
H2/feedstock ratio of 400 Nm

3/m3) the CFPP value of
the products was between -11 and -15 °C.

By the increase of the conversion the concentration
of the multibranched paraffins increased. It had a positive
effect on the cold flow properties of the products.
However, another important performance property, the
cetane number varied somewhat unfavourably.
Consequently during the catalytic conversion the cetane
number of the products decreased relative to that of the
feedstock (101 unit) as a function of the conversion.
However, products obtained at the favourable process
parameters still had a cetane number of 76–88. These
exceed significantly the standard value of 51.

125

Investigation of side products

During the isomerization about 1–3% of side-product
having jet fuel boiling range was formed. In case of this
fraction the key characteristics are the crystallization
point and the smoke point. The obtained jet fuel fractions
had an isoparaffin content of 40–70%, wherein 5–20%
was the concentration of multi-branched isoparaffins.
Consequently these fractions had a crystallization point
of between -55 °C and -50 °C, so they could satisfy the
standard value of at most -40 °C or -50 °C values. Since
they are free of aromatics, sulphur and nitrogen they burn
cleanly.

At the investigated parameter ranges 3–7% of light
hydrocarbons having gasoline boiling range also formed
in the cracking reactions. In case of this fraction the key
characteristics is the octane number. In spite of that this
fraction contained about 40–50% of isoparaffins, the
octane number was low, because they were mainly
mono-branched isoparaffins. We note that the multi-
branched paraffins having high octane number cannot
be formed over SAPO-11 catalyst because of the special
pore structure. However these fractions were free of
sulphur, aromatics, benzene and olefins, so they are good
feedstock for naphtha isomerization plants.

The obtained propane-butane fraction can be used as
heating gas, or might be used in alkylation plants because
of its high isobutene content.

Summary

During our experiments the production possibilities of
biogasoil with good cold flow properties was investigated
using a mixture of n-paraffins over Pt/SAPO-11 catalyst.

Based on the results it was found that up to a limit
the increase of the temperature and decrease of the LHSV
were favourable for the conversion of n-paraffins.
Regarding the yield, the CFPP value and cetane number
of the products the most favourable parameter combination
was the temperature of 360 °C, pressure of 40 bar, 1.0 h-1
of LHSV and 400 Nm3/m3 H2/feedstock ratio.

At the favourable process parameters product had high
yield (95.4%) and high iso-paraffin content (68.0%).
At this parameter combination the CFPP of the product
was favourable (-11 °C), which satisfy the summer
grade quality (+5 °C) of diesel standard, and with some
addition can satisfy the winter grade specification (-20 °C),
as well. The cetane number of this practically heteroatom
and aromatic free product was about 77 unit, which is
significantly higher than that is specified in the Diesel
fuel standard (51).

The jet fuel boiling range side-products had perfect
freezing point (between -55 and -50 °C), and they can
satisfy all of the specification of the standard. The
gasoline boiling range compounds can be converted to
excellent quality gasoline blending compounds by
isomerization.

Acknowledgement

We acknowledge the financial support of this work by
the Hungarian State and the European Union under the
TAMOP-4.2.1/B-09/1/KONV-2010-0003 and the
TAMOP-4.2.2/B-10/1-2010-0025 projects.

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/ENU (Use these settings to create Adobe PDF documents best suited for high-quality prepress printing. Created PDF documents can be opened with Acrobat and Adobe Reader 5.0 and later.)
>>
/Namespace [
(Adobe)
(Common)
(1.0)
]
/OtherNamespaces [
<<
/AsReaderSpreads false
/CropImagesToFrames true
/ErrorControl /WarnAndContinue
/FlattenerIgnoreSpreadOverrides false
/IncludeGuidesGrids false
/IncludeNonPrinting false
/IncludeSlug false
/Namespace [
(Adobe)
(InDesign)
(4.0)
]
/OmitPlacedBitmaps false
/OmitPlacedEPS false
/OmitPlacedPDF false
/SimulateOverprint /Legacy
>>
<<
/AddBleedMarks false
/AddColorBars false
/AddCropMarks false
/AddPageInfo false
/AddRegMarks false
/ConvertColors /ConvertToCMYK
/DestinationProfileName ()
/DestinationProfileSelector /DocumentCMYK
/Downsample16BitImages true
/FlattenerPreset <<
/PresetSelector /MediumResolution
>>
/FormElements false
/GenerateStructure false
/IncludeBookmarks false
/IncludeHyperlinks false
/IncludeInteractive false
/IncludeLayers false
/IncludeProfiles false
/MultimediaHandling /UseObjectSettings
/Namespace [
(Adobe)
(CreativeSuite)
(2.0)
]
/PDFXOutputIntentProfileSelector /DocumentCMYK
/PreserveEditing true
/UntaggedCMYKHandling /LeaveUntagged
/UntaggedRGBHandling /UseDocumentProfile
/UseDocumentBleed false
>>
]
>> setdistillerparams
<<
/HWResolution [2400 2400]
/PageSize [612.000 792.000]
>> setpagedevice