Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
1
HYDROCARBON COMPOSITION AND METHOD FOR
PRODUCING A HYDROCARBON COMPOSITION
FIELD OF THE INVENTION
The present disclosure relates to a hydrocarbon composition and to a
method for producing a hydrocarbon composition.
BACKGROUND
Isomerization refers to a chemical process by which a compound is
transformed into one or more of its isomeric forms, i.e. forms having the same
chemical composition but a different structure or configuration and possibly
dif-
ferent physical and chemical properties. For example, branched-chain hydrocar-
bons are better motor fuels than their straight-chain isomers. The
isomerization
of straight-chain hydrocarbons to their corresponding branched-chain isomers
represents an example of isomerization reactions of great industrial
importance.
Isomerized hydrocarbon compositions with a lowered aromatic con-
tent are commercially available in a chain length of C7-C14. The
dearomatization
method used for obtaining these highly isomerized hydrocarbon compositions is
hydrogenation. In these compositions the aromatic content is 1 ppm.
A method for obtaining isomerized hydrocarbon fractions is disclosed
in a patent application W02015/101837, including a chain length of C14-C15.
SUMMARY
An object is to provide a hydrocarbon composition with extremely low
aromatics content. The objects are achieved by a method, composition, and use
thereof, as defined herein.
An exemplary method is based on conducting hydrodeoxygenation
and optionally isomerization of raw material, wherein the method further com-
prises one or more solvent extraction steps and optionally hydrogenation to re-
move aromatic and/or naphthenic hydrocarbons from the material. The original
aromatic and/or naphthenic content of the raw material is less than 2 vol-%.
In
the method, the aromatic and/or naphthenic content is reduced by more than
45%, preferably by more than 60%. An exemplary composition contains hydro-
carbons produced by said method, wherein the total aromatic and/or naphthenic
hydrocarbon content of the composition is less than a predefined low value,
and
C15-C20 i-paraffins are the main fraction of the hydrocarbon content of the
com-
position, weight basis.
Date Recue/Date Received 2020-09-11
la
According to one particular aspect, the invention relates to a method
for producing hydrocarbons with a very low aromatics and/or naphthenics con-
tent, the method comprising
conducting hydrodeoxygenation and optionally isomerization of raw
material having an aromatics and/or naphthenics content of less than 2 vol-%,
wherein the method further comprises one or more solvent extraction steps and
optionally a hydrogenation step to remove aromatic and/or naphthenic hydro-
carbons from the material,
thereby reducing the aromatics and/or naphthenics content of the ma-
terial by more than 45%, to produce hydrocarbons with an aromatics and/or
naphthenics content of less than 10 000 ppm, volume basis.
According to another particular aspect, the invention relates to a hy-
drocarbon composition produced by a method as defined herein, wherein the to-
tal aromatic and/or naphthenic hydrocarbon content of the composition is less
than 10 000 ppm, volume basis.
According to another particular aspect, the invention relates to the use
of a composition as defined herein in a coating, paint, lacquer, varnish,
polish, ink,
adhesive, sealant, resin, plastic, catalyst, cleaning composition, peroxide
desensi-
tizer, pigment dispersion, carrier fluid for an active ingredient,
antioxidant, bio-
cide, insecticide, air freshener, crop protection composition, detergent,
grease
removal composition, dry cleaning composition, cosmetic, personal care composi-
tion, pharmaceutical, extender in a dental impression material, vaccine, food
in-
gredient, flavour composition, fragrance, natural oil extraction, oil field
chemical,
drilling mud composition, extraction process composition, plasticizer for
elasto-
mer, paper processing chemical, lubricant, functional fluid, transformer oil,
metal
working composition, rolling or cutting fluid, water treatment composition,
wood
treatment composition, construction chemical, mould release material,
explosive,
mining chemical, solvent extraction composition, fuel component, heating oil,
lamp oil, or a combination thereof.
Date Recue/Date Received 2020-09-11
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DETAILED DESCRIPTION OF EMBODIMENTS
The following embodiments are exemplary. Although the specification
may refer to "an", "one", or "some" embodiment(s) in several locations, this
does
not necessarily mean that each such reference is to the same embodiment(s), or
that the feature only applies to a single embodiment. Single features of
different
embodiments may also be combined to provide other embodiments. Furthermore,
words "comprising", "containing" and "including" should be understood as not
lim-
iting the described embodiments to consist of only those features that have
been
mentioned and such embodiments may contain also features/structures that have
not been specifically mentioned.
An embodiment discloses a method for dearomatization and/or
denaphthenization of raw material to produce a hydrocarbon product. The method
is based on the use of hydrodeoxygenation and solvent extraction, and
optionally
isomerization and hydrogenation, in combination. This means that the method
comprises the consecutive method steps of hydrodeoxygenation and solvent ex-
traction, and possibly isomerization and hydrogenation. The method may further
comprise a step of separating different hydrocarbon fractions by
fractionation. The
method steps may be carried out in one or multiple reactors.
The order of said method steps may differ from the one given above. For
example, 1st step may be solvent extraction, 2nd step may be hydrogenation,
and 3rd
step may be solvent extraction, or Pt step may be hydrogenation, and 2" step
may
be solvent extraction.
In an embodiment, one or more of said method steps may be performed
simultaneously.
A highly isomerized hydrocarbon product with very low aromatic (or
naphthenic) content may be produced with a process combining hydrodeoxygena-
tion, isomerization and solvent extraction (and optionally hydrogenation
and/or
fractionation).
The method may be carried out in one or multiple reactors.
The feedstock/raw material for the process may be paraffinic hydrocar-
bon, isoparaffinic hydrocarbon, natural gas, biogas, coal, diesel and/or
naphtha or
it may be of renewable and/or biological origin, such as vegetable oil,
hydrotreated
vegetable oil, animal fat, fish fat, microbial oil, algae oil and/or any other
suitable
natural or biological oil, such as natural waste oil or natural residue oil.
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Solvent extraction provides an effective and inexpensive method for ar-
omatics and/or naphthenics removal. The method enables further removal of aro-
matics and/or naphthenics from a raw material having a low aromatics and/or
naphthenics content.
Paraffins arranged in straight chains may be referred to as normal par-
affins i.e. n-paraffins, and paraffins arranged in branched chains may be
referred to
as isoparaffins i.e i-paraffins. A composition produced by the method may
contain
n- and i-paraffins in different ratios depending on the processing parameters.
An embodiment discloses a hydrocarbon composition A and a method
to for producing the hydrocarbon composition A. The hydrocarbon composition
A
contains mainly C5-C10 i- and/or n-paraffins. In the method for producing the
hy-
drocarbon composition A, the steps of hydrodeoxygenation, isomerization and
sol-
vent extraction are combined with a fractionation step where i- and n-
paraffins are
separated. The end product obtained contains over 90 wt-% C5-C10 i- and/or n-
paraffins.
Another embodiment discloses a hydrocarbon composition B and a
method for producing the hydrocarbon composition B. The hydrocarbon composi-
tion B contains over 80 wt-% C10-C20 i-paraffins and less than 20 wt-% n-paraf-
fins. In the method for producing the hydrocarbon composition B, the steps of
hy-
drodeoxygenation, isomerization and solvent extraction may be combined with a
fractionation step. End products with a variable content of C14-C20 paraffins
(over
80 wt-% of i-paraffins) are obtained. The fractionated end products may be,
for
example, mainly C10-C15 paraffins, mainly C14-C16 paraffins, mainly C15-C18
par-
affins and/or mainly C17-C18 paraffins.
In an embodiment, a composition is disclosed containing highly isomer-
ized hydrocarbons, wherein the total aromatic and/or naphthenic hydrocarbon
content of the composition is less than a predefined low value, and i-
paraffins are
the main fraction of the hydrocarbon content of the composition.
In an embodiment, the total aromatic and/or naphthenic hydrocarbon
content of the composition is less than 10 000 ppm, preferably 4000 ppm or
less,
more preferably 2000 ppm or less, yet more preferably 1600 ppm or less, yet
more
preferably 1200 ppm or less, yet more preferably 1000 ppm or less, yet more
pref-
erably 500 ppm or less, yet more preferably 100 ppm or less, yet more
preferably
50 ppm or less, yet more preferably 30 ppm or less, most preferably about 20
ppm,
volume basis.
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In an embodiment, the hydrocarbon composition is produced from re-
newable and/or biological raw material. The renewable and/or biological raw ma-
terial comprises at least one of vegetable oil, animal fat, fish fat,
microbial oil, algae
oil, natural waste oil, and or natural residue oil.
The hydrocarbons may be C15-C20 hydrocarbons or C5-C10 hydrocar-
bons.
In an embodiment, the composition comprises 80 wt-% C10-C20 i-par-
affins or more, preferably about 93 wt-%, based on the total weight of the
compo-
sition, and 20 wt-% C10-C20 n-paraffins or less, based on the total weight of
the
composition. C14-C20 paraffins, C10-C15 paraffins, C14-C16 paraffins, C15-C18
paraffins or C17-C18 paraffins are the main fraction of the hydrocarbon
content of
the composition. The total i-paraffinic content of the composition is more
than 80
wt-%, based on the total weight of the composition. The total n-paraffinic
content
of the composition is less than 20 wt-%, based on the total weight of the
composi-
tion.
In an embodiment, the composition comprises about 90 wt-% C5-C10
and/or n-paraffins, based on the total weight of the composition.
In an embodiment, the hydrocarbon composition is produced by a pro-
cess comprising hydrodeoxygenation and optionally isomerization of raw
material,
comprising at least one step of solvent extraction, and optional steps of
hydrogena-
tion and/or fractionation. The original aromatie/naphthenic content of the raw
material/feedstock is less than 2 vol-%. In the method, the original
aromatic/naph-
thenic content is reduced by more than 45%, preferably by more than 60%.
In an embodiment, the composition is suitable for use as a solvent or a
solvent component.
In an embodiment, the composition is in liquid form.
In an embodiment, the composition is an emulsion.
In an embodiment, the composition may be used in a coating, paint, lac-
quer, varnish, polish, ink, adhesive, sealant, resin, plastic, catalyst,
cleaning compo-
sition, peroxide desensitizer, pigment dispersion, carrier fluid for an active
ingre-
dient, antioxidant, biocide, insecticide, air freshener, crop protection
composition,
detergent, grease removal composition, dry cleaning composition, cosmetic, per-
sonal care composition, pharmaceutical, extender in a dental impression
material,
vaccine, food ingredient, flavour composition, fragrance, natural oil
extraction, oil
field chemical, drilling mud composition, extraction process composition,
plasti-
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cizer for elastomer, paper processing chemical, lubricant, functional fluid,
trans-
former oil, metal working composition, rolling or cutting fluid, water
treatment
composition, wood treatment composition, construction chemical, mould release
material, explosive, mining chemical, solvent extraction composition, fuel
compo-
s .. nent, heating oil, lamp oil, or a combination thereof.
In an embodiment, the method for producing the hydrocarbon compo-
sition comprises conducting hydrodeoxygenation and optionally isomerization of
raw material, wherein the method further comprises a step of solvent
extraction
and optionally hydrogenation. The method may further comprise conducting sep-
to aration of the resulting material, wherein the separation may include
fractionation
or any other suitable separation method. The method may be carried out in one
or
multiple reactors.
In an embodiment, the solvent used in the solvent extraction includes
at least one of N-methyl-2-pyrrolidone (NMP), furfural, dimethyl formamide
(DMF), DMSO (dimethylsulphoxide), DMI (dimethyl isosorbide), polar solvent, ar-
omatic solvent, dipolar aprotic solvent, ionic liquid, deep eutectic solvent,
sulpholane, glycol, and phenol.
A composition comprising highly isomerized hydrocarbons as used
herein refers to a composition where the degree of isomerization is high. For
0)(-
ample, the composition may comprise a high weight percentage of i-paraffins
com-
pared to the weight percentage of normal paraffins (n-paraffins), so that the
main
fraction of the composition comprises i-paraffins. However, it is also
possible that
the composition comprises an equal or higher weight percentage of n-paraffins
compared to the weight percentage of i-paraffins. It is also possible that the
coin-
position comprises a high weight percentage of i-paraffins but no n-paraffins,
or
vice versa.
According to an exemplary aspect, provided is a method for producing
the composition comprising said paraffins. The method can comprise hydrotreat-
ing a raw material of renewable/biological origin to obtain a hydrotreated
product
comprising n-paraffins and isomerizing the hydrotreated product to obtain an
isomerizecl product comprising i-paraffins and separation of said composition
by
solvent extraction and possibly fractionation.
Example 1
A trace amount of aromatics from the composition B containing approx-
imately 90 wt-% i-paraffins and 0,31 vol-% aromatic compounds were extracted
with two different solvents, according to a 4-step-working procedure. The
chosen
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solvents were N-methyl-2-pyrrolidone (NMP) and dimethylformamide (DMF). 10
vol-% distilled water was added in both solvents to increase the efficiency.
100 ml
of the composition B was extracted three times with the solvent in a 1:1
composi-
tion B to solvent ratio. A mixing time of 2 min was used in each step. A 500
mL glass
separation funnel was used. After mixing, the extract was centrifuged to
separate
the extract. Table 1 illustrates the aromatic contents (in vol-%) of samples
ex-
tracted in 3-step solvent extraction followed by a washing step with water as
ana-
lyzed by using a NM77 method (UV spectrophotometric detection method). N MP=
N-methyl-2-pyrrolidone, DMF=dimethylformamide.
Table 1
NMP DMF
Non-extracted composition B 0,31 0,31
Extract after step 1 0,2 0,16
Extract after step 3 0,12 0,16
Extract after step 3, washed with F120 0,12 0,16
As can be seen from Table 1, both the tested solvents clearly reduced
the amount of aromatic residues in the composition B. Already a single step
solvent
extraction procedure reduced the amount of aromatics in the composition B by
35% in case of NMP, and by 48% in case of DMF. After three solvent extraction
steps, NMP showed to be more effective leading to a 61% reduction in the
aromatic
content of the composition B.
Thus, liquid-liquid extraction (solvent extraction) may be applied for
the separation of aromatics and/or naphthenics from the compositions A and/or
B. Solvents suitable for the extraction of the aromatic/naphthenic compounds
from
the compositions A and/or B may include, for example, N-methyl-2-pyrrolidone
(NMP), furfural, dimethyl formamide (DMF), DMSO (dimethylsulphoxide), DMI (di-
methyl isosorbide), and/or phenol. Water or some other co-solvent, such as
alco-
ho], may be used to enhance the separation process of the aromatics from the
com-
position. Also certain ionic liquids and/or deep eutectic solvents, such as
choline
chloride, may be used to remove aromatics from the composition.
In an embodiment, the method comprises performing the consecutive
(and/or simultaneous) steps of hydrodeoxygenation, and optionally
isomerization
and hydrogenation, and one or more solvent extraction steps until the
aromatics
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and/or naphthenics content of the material is reduced by more than 45%; for ex-
ample, several consecutive solvent extraction steps may be required until the
de-
sired reduction of 45% in the aromatics and/or naphthenics content of the
material
is achieved and hydrocarbons are produced with an aromatics and/or naphthenics
content of less than 10 000 ppm, preferably 4000 ppm or less, more preferably
2000 ppm or less, yet more preferably 1600 ppm or less, yet more preferably
1200
ppm or less, yet more preferably 1000 ppm or less, yet more preferably 500 ppm
or less, yet more preferably 100 ppm or less, yet more preferably 50 ppm or
less,
yet more prefer-ably 30 ppm or less, most preferably about 20 ppm, volume
basis
It will be obvious to a person skilled in the art that, as the technology
advances, the inventive concept can be implemented in various ways. The inven-
tion and its embodiments are not limited to the examples described above but
may
vary within the scope of the claims.
