Note: Descriptions are shown in the official language in which they were submitted.
lZ8632i
F-3513 AN OXYGENATE CONVERSION PROCESS
This invention relates to an oxygenate conversion process
using a zeolite catalyst.
Zeolitic materials, both natural and synthetic, have been
demonstrated in the past to have catalytic properties for various
types of hydrocarbon conversion. Certain zeolitic materials are
ordered, porous crystalline aluminosilicates having a definite
crystalline structure as determined by X-ray diffraction, within
which there are a large number of smaller cavities which may be
interconnected by a number of still smaller channels or pores.
These cavities and pores are uniform in size within a specific
zeolitic material. Since the dimensions of these pores are such as
to accept for adsorption molecules of certain dimensions while
rejecting those of larger dimensions, these materials have come to
be known as "molecular sieves" and are utilized in a variety of ways
to take advantage of these properties.
Such molecular sieves, both natural and synthetic, include
a wide variety of positive ion-containing crystalline
aluminosilicates. These aluminosilicates can be described as a
rigid three-dimensional framework of Siû4 and A104 in which the
tetrahedra are cross-linked by the sharing of oxygen atoms whereby
the ratio of the total aluminum and silicon atoms to oxygen atoms is
1:2. The electrovalence of the tetrahedra containing aluminum is
balanced by the inclusion in the crystal of a cation, for example an
alkali metal or an alkaline earth metal cation. This can be
expressed wherein the ratio of aluminum to the number of various
cations, such as Ca/2, Sr/2, Na, K or Li, is equal to unity. One
type of cation may be exchanged either entirely or partially with
another type of cation utilizing ion exchange techniques in a
conventional manner. By means of such cation exchange, it has been
possible to vary the properties of a given aluminosilicate by
~ suitable selection of the cation.
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lZ86321
F-3513 --2--
Prior art techniques have resulted in the formation of a
great variety of synthetic zeolites. The zeolites have come to be
designated by letter or other convenient symbols, as illustrated by
zeolite A (U. S. Patent 2,882,243), zeolite X (U. 5. Patent
2,882,244), zeolite Y (U. S. Patent 3,130,ûû7), zeolite ZK-5 (U. S.
Patent 3,247,195), zeolite ZK-4 (U. S. Patent 3,314,752), zeolite
ZSM-5 (U. S. Patent 3,7û2,886), zeolite ZSM-ll (U. S. Patent
3,7û9,979), zeolite ZSM-12 (U. S. Patent 3,832,449), zeolite ZSM-2û
(U. S. Patent 3,972,983), ZSM-35 (U. S. Patent 4,û16,245), ZSM-38
(U. S. Patent 4,û46,859), and zeolite ZSM-23 (U. S. Patent
4,076,842).
The SiO2/A12û3 ratio of a given zeolite is often
variable. For example, zeolite X can be synthesized with
Siû2/A1203 ratios of from 2 to 3; zeolite Y, from 3 to about
6. In some zeolites, the upper limit of the SiO2/A12û3 ratio
is unbounded. ZSM-5 is one such example wherein the
Siû2/A1203 ratio is at least 5 and up to infinity. U. S.
Patent 3,941,871 (Re. 29,948) discloses a porous crystalline
silicate made from a reaction mixture containing no deliberately
added alumina in the recipe and exhibiting the X-ray diffraction
pattern characteristic of ZSM-5.
The present invention relates to the use of a novel porous
crystalline zeolite, designated as "ZSM-58", having an X-ray
diffraction pattern exhibiting values substantially as set forth in
Table 1 below in the conversion of oxygenates to hydrocarbons.
Accordingly, the invention resides in a process for
converting a feedstock comprising organic compounds selected from
the group consisting of alcohol, carbonyl, ether and mixtures
thereof to conversion product comprising hydrocarbon compounds,
which comprises contacting said feedstock at conversion conditions
with a catalyst composition comprising a crystalline zeolite
characterized by an X-ray diffraction pattern exhibiting values
substantially as set forth in Table 1 of the specification.
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lZ~3~i3~1
F-3513 -3-
The zeolite used in the present process, ZSM-58 is
( described in more detail in our copending Canadian Patent
Application No.500,708.
In the as-synthesized form, ZSM-58 has a formula, on an
anhydrous basis and in terms of moles of oxides per lOû moles of
silica, as follows:
(0.1-2.0)R20: (0.02-l.O)M2~nO: (0.1-2)A1203:(100)5iO2
wherein M is an alkali or alkaline earth metal, n is the valence of
M, and R is an organic cation of a methyltropinium salt. The
typical X-ray diffraction pattern intensities for ZSM-58 are shown
in Table 1 below.
TABLE 1
Interplanar
Relative Intensitv, I/Io
13.7û + û.20 W
11.53 + 0.20 W-VS
lû.38 + 0.20 W
7.82 + 0.14 W-VS
6.93-6.79 + 0.14 W-VS
6.19 + 0.14 W-VS
5.94 + 0.12 W-M
5.77 + û.12 VS
5.22 + 0.12 W
5.18 + û.lû VS
4.86 + û.09 M-S
4.72 + O.û8 S
4.57 + 0.08 W
4.51 + û.û8 S
4.43 + 0.08 W
4.19 + 0.08 W
4.15 + 0.08 . M
4.00 + 0.07 W
3.97 + û.07 W
3.89 + O.û7 W
3.84 + 0.07 M
3.81 + 0.07 W-M
3.59 + 0.06 W
3.46 + 0.06 W-M
3.41 + 0.06 S-VS
3.36 + 0.06 S-VS
3.32 + 0.06 M-S
3.29 + 0.05 W
3.17 + 0.05 W-M
3.û7 + û.û5 W-M
3.05 + 0.05 W-M
3 01 + O.û5 W-M
: 2 88 + 0.05 W
2 85 + 0.05 W
2 75 + 0.05 W
: 2.67 + 0.04 W
. 2.60 + 0.04 W
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F-3513
These values were determined by standard techniques. The
radiation was the K-alpha doublet of copper and a diffractometer
equipped with a scintillation counter and an associated computer was
used. The peak heights, I, and the positions as a function of 2
theta, where theta is the Bragg angle, were determined using
algorithms on the computer associated with the spectrometer. From
these, the relative intensities, lOû I/Io, where Io is the
intensity of the strongest line or peak, and d (obs.) the
interplanar spacing in Angstrom Units (A), corresponding to the
recorded lines, were determined. In Table 1, the relative
intensities are given in terms of the symbols W-weak, M=medium,
S=strong and VS=very strong. In terms of intensities, these may be
generally designated as follows:
~ = O - 20
M = 20 - 40
5 = 40 - 60
VS = 60 - 100
It should be understood that this X-ray diffraction pattern is
characteristic of all the species of ZSM-58 compositions. The
sodium form as well as other cationic forms reveal substantially the
same pattern with some minor shifts in interplanar spacing and
variation in relative intensity. Other minor variations can occur,
depending on the silicon to aluminum ratio of the particular sample,
as well as its degree of thermal treatment. Multiplets may be
observed in the typical X-ray pattern for ZSM-58 at d-spacing values
of 6.93-6.79 + 0.14, 4.86 ~ 0.09, 3.41 + 0.06, 3.07 + 0.05 and 3.01
+ 0.05 Pngstroms.
ZSM-58 is thermally stable and exhibits molecular shape
selective properties as indicated by sorption tests.
The crystalline silicate ZSM-58 can be prepared from a
reaction mixture containing sources of an alkali or alkaline earth
metal oxide, an oxide of aluminum, an oxide of silicon, an organic
cation of a methyltropinium salt, e.g. halide, hydroxide, sulfate,
etc., and water, said reaction mixture having a composition, in
terms of mole ratios of oxides, within the following ranges:
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l2~3al
F-3513
--5--
Reactants Use~ul Preferred
sio~/A123 50-1000 70-500
H207SiO2 5-200 10-100
OH-/SiO2 0-2.0 0.10-1.0
M/SiO2 0.01-3.0 0.10-1.0
R/SiO2 0.01-2.0 0.10-0.50
wherein R and M are as above defined.
Crystallization of ZSM-5a can be carried out under either
static or stirred conditions in a suitable reactor vessel, such as
for example, polypropylene jars or teflon lined or stainless steel
autoclaves. The total useful range of temperatures for
crystallization is from 80C to 225C for a time sufficient for
crystallization to occur at the t~mperature used, e.g. from 24 hours
to 60 days. Thereafter, the crystals are separated from the liquid
and recovered. The reaction mixture can be prepared utilizing
materials which supply the appropriate oxides. Such materials may
include sodium silicate, silica hydrosol, silica gel, silicic acid,
sodium hydroxide, a source of aluminum, and the methyltropinium salt
directing agent. The methyltropinium salt may be synthesized by
selective methylation of 3-tropanol at the bridgehead nitrogen.
This salt has the following formula:
F+ F
¦H3CNCH3 CHOH ¦ X~
H2C - CH - CH2 ¦
wherein X is an anion, such as, for example, a halide (e.g. iodide,
chloride or bromide), nitrate, hydroxide, sulfate, bisulfate and
perchlorate.
It should be realized that the reaction mixture oxides can
be supplied by more than one source. The reaction mixture can be
prepared either batchwise or continuously. Crystal size and
~ crystallization time of the new crystalline material will vary with
; the nature of the reaction mixture employed and the crystallization
conditions.
lZ863~
F-3 Sl 3 --6--
In all cases, synthesis of the ZSM-58 crystals is
facilitated by the presence of at least 0.01 percent, preferably
0.10 percent and still more preferably l percent, seed crystals
(based on total weight) of crystalline product.
The crystals prepared by the instant method can be shaped
into a wide variety of particle sizes. Generally speaking, the
particles can be in the form of a powder, a granule, or a molded
product, such as an extrudate having particle size sufficient to
pass through a 2 mesh (Tyler) screen and be retained on a 400 mesh
(Tyler) screen. In cases where the catalyst is molded, such as by
extrusion, the crystals can be extruded before drying or partially
dried and then extruded.
The original alkali or alkaline earth metal cations of the
as synthesized ZSM-58 can be replaced in accordance with techniques
well known in the art, at least in part, by ion exchange with other
cations. Preferred replacing cations include metal ions, hydrogen
ions, hydrogen precursor, e.g. ammonium, ions and mixtures thereof.
Particularly preferred cations are those which render the ZSM-58
catalytically active, especially for certain hydrocarbon conversion
reactions. These include hydrogen, rare earth metals and metals of
Groups IIA, IIIA, IVA, IB, IIB, IIIB, IVB and VIII of the Periodic
Table of the Elements.
Typical ion exchange technique would be to contact the
synthetic ZSM-58 with a salt of the desired replacing cation or
cations. Examples of such salts include the halides, e.g.
chlorides, nitrates and sulfates.
The crystalline silicate of the present invention can be
used either in the alkali or alkaline earth metal form, e.g. the
sodium or potassium form; the ammonium form; the hydrogen form or
another univalent or multivalent cationic form. ~hen used as a
catalyst, ZSML58 will be subjected to thermal treatment to remove
part or all o~ ~ny organlc constltuent.
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12~36321
F-3513 _7_
The crystalline silicate can also be used as a catalyst in
intimate combination with a hydrogenating component such as
tungsten, vanadium, molybdenum, rhenium, nickel, cobalt, chromium,
manganese, or a noble metal such as platinum or palladium where a
hydrogenation-dehydrogenation function is to be performed. Such
component can be exchanged into the composition to the extent
aluminum is in the structure, impregnated therein or intimately
physically admixed therewith. Such component can be impregnated in ~ -
or on to it such as for example, by, in the case of platinum,
treating the ZSM-58 with a solution containing a platinum
metal-containing ion. Thus, suitable platinum compounds include
chloroplatinic acid, platinous chloride and various compounds
containing the platinum amine complex.
The above crystalline silicate, especially in its metal,
hydrogen and ammonium forms can be beneficially converted to another
form by thermal treatment. This thermal treatment is generally
performed by heating one of these forms at a temperature of at least
37ûC for at least 1 minute and generally not longer than 2û hours.
While subatmospheric pressure can be employed for the thermal
treatment, atmospheric pressure is desired for reasons of
convenience. The thermal treatment can be performed at a
temperature up to about 925C. The thermally treated product is
particularly useful in the catalysis of certain hydrocarbon
conversion reactions.
The new silicate, when employed as a catalyst in an organic
compound conversion process should be dehydrated, at least
partially. This can be done by heating to a temperature in the
range of 200C to 595C in an inert atmosphere, such as air,
nitrogen, etc. and at atmospheric, subatmospheric or
superatmospheric pressures for between 30 minutes and 48 hours.
Dehydration can also be performed at room temperature merely by
placing ZSM-58 in a vacuum, but a longer time is required to obtain
, a sufficient amount of dehydration.
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lZ~3~3,_1
F-3513 -8-
In accordance with the present invention, ZSM-58 is used as
a catalyst in the conversion of organic oxygenates selected from
alcohols, carbonyls, ethers and mixtures thereof to hydrocarbons.
Feedstock alcohols will be aliphatic alcohols of from 1 to 6 carbon
atoms, preferably from 1 to 3 carbon atoms, e.g., methanol and
ethanol. Feedstock carbonyls will be lower aliphatic carbonyls,
such as, for example, acetone. Feedstock ethers will be lower
aliphatic ethers of up to 6 carbon atoms, e.g., from 2 to 6 carbon
atoms, such as dimethylether, n-propyl ether, p-dioxane, trioxane
and hexose.
The product of such oxygenate conversion will be
predominantly hydrocarbons including olefins of from 2 to 5 or more
carbon atoms with C2 olefins usually less than about 10% of the
total and C5+ olefins usually less than about 15~ of the total.
Aromatic hydrocarbons, such as durene, are also produced. C2,
C~ and C4 olefins are desired chemical products, and C5+
products are valuable as gasoline components. In general, the
reaction conditions employed will be a temperature of from 15û to
600C, a pressure of from 50 to 5065 kPa (0.5 to 50 atmospheres) and
a weight hourly space velocity of from 0.5 to 100/hr. 1.
As in the case of many catalytic uses, it is desirable to
incorporate the ZSM-58 with another material resistant to the
temperatures and other conditions employed in organic conversion
processes. Such materials include active and inactive materials and
synthetic or naturally occurring zeolites as well as inorganic
materials such as clays, silica and/or metal oxides such as alumina.
The latter may be either naturally occurring or in the form of
gelatinous precipitates or gels including mixtures of silica and
metal oxides. Use of a material in conjunction with the ZSM-58
crystal, i.e. combined therewith, which is active, tends to change
the conversion and/or selectivity of the catalyst in certain
. .
12~363~1
f-3513 _9_
organic conversion processes. Inactive materials suitably serve as
diluents to control the amount of conversion in a given process so
that products can be obtained economically and orderly without
employing other means for controlling the rate of reaction. These
materials may be incorporated into naturally occurring clays, e.g.
bentonite and kaolin, to improve the crush strength of the catalyst
under commercial operating conditions. Said materials, i.e. clays,
oxides, etc., function as binders for the catalyst. It is desirable
to provide a catalyst having good crush strength because in
commercial use it is desirable to prevent the catalyst from breaking
down into powder-like materials. These clay binders have been
employed normally only for the purpose of improving the crush
strength of the catalyst.
Naturally occurring clays which can be composited with the
new crystal include the montmorillonite and kaolin family, which
families include the subbentonites, and the kaolins commonly known
as Dixie, McNamee, Georgia and Florida clays or others in which the
main mineral constituent is halloysite, kaolinite, dickite, nacrite,
or anauxite. Such clays can be used in the raw state as originally
mined or initially subjected to calcination, acid treatment or
chemical modification. Binders useful for compositing with the
present crystal also include inorganic oxides, notably alumina.
In addition to the foregoing materials, the ZSM-58 crystal
can be composited with a porous matrix material such as
silica-alumina, silica-magnesia, silica-zirconia, silica-thoria,
silica- beryllia, silica-titania as well as ternary compositions
such as silica-alumina-thoria, silica-alumina-zirconia
silica-alumina-magnesia and silica-magnesia-zirconia.
rhe relative proportions of finely divided crystalline
material and inorganic oxide matrix vary widely, with the crystal
content ranging from 1 to 90 percent by weight and more usually,
particularly when the composite is prepared in the form of beads, in
the range of 2 to 80 weight percent of the composite.
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lZ13~3;~1
F-3513 10
In order to more fully illustrate the nature of the
invention and the manner of practicing same, the following
examples are presented. In the examples, whenever sorption
data are set forth for comparison of sorptive capacities for
cyclohexane and/or n-hexane, they were determined as follows:
A weighed sample of the calcined ZSM-58 adsorbant was
contacted with the desired pure adsorbate vapor in an
adsorption chamber, evacuated to less than 1 mm and contacted
with 80 mm Hg of n-hexane or cyclohexane vapor, pressures less
than the vapor-liquid equilibrium pressure of the respective
adsorbate at 90C. The pressure was kept constant (within
about + û.5 mm) by addition of adsorbate vapor controlled by a
manostat during the adsorption period, which did not exceed
about 8 hours. As adsorbate was adsorbed by the ZSM-58, the
decrease in pressure caused the manostat to open a valve which
admitted more adsorbate vapor to the chamber to restore the
above control pressures. Sorption was complete when the
pressure change was not sufficient to activate the manostat.
The increase in weight was calculated as the adsorption
capacity of the sample in g/lûû 9 of calcined adsorbant.
When Alpha Value is examined, it is noted that the
Alpha Value is an approximate indication of the catalytic
cracking activity of the catalyst compared to a standard
catalyst and it gives the relative rate constant (rate of
normal hexane conversion per volume of catalyst per unit
time). It i5 based on the activity of the highly active
silica-alum~na cracking catalyst taken as an Alpha of 1 (Rate
Constant = û.016 sec 1). The Alpha Test is described in U.S.
Patent 3,354,078 and in The Journal of Catalysis, Vol. IY, pp.
522-529 (August 1965). It is noted that intrinsic rate
constants for many acid-catalyzed reactions are proportional to
the Alpha Value for a particular crystalline silicate catalyst,
~ ~ i.e. the rates for toluene disproportionation, xylene; isomerization, alkene conversion and methanol conversion (see
~'The Active Site of Acidic Aluminosilicate Catalysts,~' Nature,
Vol. 3C9, No. 5969, pp. 589-591, 14 June 1984).
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F-3513 --11--
EXAMPLES 1 - 6
Six separate synthesis reaction mixtures were prepared with
compositions indicated in Table 2. The mixtures were prepared with
silica sol (30 percent SiO2), NaA102, NaOH, a methyltropinium
salt, i.e. iodide, and water. The mixtures were maintained at 160C
for 4 days in a stainless steel, stirred (40û rpm) autoclave at
autogenous pressure. Solids were separated from any unreacted
components by filtration and then water washed, followed by drying
at 110C. The product crystals were analyzed by X-ray diffraction
and chemical analysis. The product of Example 1 was found to be
crystalline ZSM-58 with a trace of unidentified second component
impurity. The products from Examples 2-6 proved to be 100 percent
crystalline ZSM-58.
The X-ray diffraction pattern of the Example 4 crystals,
after calcination at 538C for 17 hours in air, is set forth as
illustration in Table 3. ûther properties of each crystalline
product are presented in Table 4. In the latter table, compositions
are calculated on the basis of 100 (Siû2 + A102) tetrahedra.
The as-synthesized ZSM-58 from these examples contains from 3.8 to
5.0 methyltropinium cations per 100 tetrahedra.
TAaLE 2
Mixture Composition (mole ratios)
Example SiO2 H2o ûH- Na~ R*
A1203 SiO2 SiO2 sio2 SiO2
`~ ~ 1 300 40 0.30 0.31 0.25
2 200 40 0.30 0.31 0.25
3 90 40 0.40 0.42 0.25
4 90 40 0.30 0.32 0.25
go 40 0.30 0.32 0.25
6 70 40 0.30 0.33 0.25
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;~ ~ *R = methyltropinium cation.
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12~3~;32!~
--12-
F-3513
TAO~E 3
ObservedRelative
d(A) 2 ThetaIntensity
13.57425 6.511 7.4
11.44933 7.721 51.2
10.29541 8.588 4.1
7.76959 11.389 53.6
6.89736 12.834 60.1
6.84556 12.932 33.0
6.15999 14.378 57.8
5 91115 14.987 19.5
5 74071 15.435 85.8
5.16339 17.173 100.0
4.84326 18.317 51.9
4.70389 18.865 56.0
4.52632 19.612 20.3
4.49392 19.755 51.7
4.41905 20.093 4.7
4.13559 21.486 26.0
3 98517 22.307 11.8
3 96826 22.404 8.9
3.87191 22.969 17.1
3.82281 23.268 30.6
3.80712 23.365 25.6
3.57841 24.882 16.2
3.44668 25.849 35.2
3.38811 26.303 96.5
3.35769 26.546 86.7
3.34862 26.619 80.8
3.30859 26.947 66.2
3.28346 27.158 9.1
3.16039 28.237 23.3
3.06246 29.159 26.8
3.06070 29.176 31.2
3.03737 29.406 22.7
2.99654 29.816 25.2
2.98814 29.901 21.2
2.87045 31.158 4.1
2.84237 31.473 5.1
2.66429 33.638 5.5
2.58922 34.643 4.8
2.50349 35.869 4.3
2.48809 36.099 6.3
2.43821 36.863 9.0
2.42105 37.134 14.9
2.39052 37.626 5.8
2.35412 38.230 2.8
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12~6321
F-3513 --13--
TABLE 3
(Continued)
Observed Relative
d(A) 2 Theta Intensity
-
2.33296 38.591 4.3
2.30029 39.161 16.7
2.23686 40.319 2.4
2.23188 40.413 1.9
2.21126 40.807 3.2
2.16400 41.739 1.7
2.11106 42.836 1.4
2.07314 43.660 3.0
2.03910 44.427 0.3
1.97783 45.880 11.4
1.95022 46.568 4.4
1.93214 47.030 3.9
1 9150} 47.476 3.7
1 83810 49.594 6.4
1.83554 49.667 5.5
TA8LE 4
COMPOSITION
Moles C Moles ,oer Mole A1203 Al Na+ N+ R
Example Mole N N2 Na20 SiO2 lOOTd lOOTd lTd lOOTd
_
1 9.5 4.09 0.85 223 0.89 0.76 3.6 3.8
2 11.2 2.43 0.74140 1.4 1.0 3.4 4.2
3 9.6 1.85 0.13 83 2.4 0.30 4.4 4.7
4 10.2 1.69 0.1278 2.5 0.30 4.2 4.8
10.8 1.77 0.25 85 2.3 0.58 4.1 4.9
6 9.6 1.50 0.1062 3.1 0.30 4.7 5.0
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12~3~3~1
F-3513 --14--
EXAMPLE 7
A sample of the Example 4 product crystals, having been
calcined in nitrogen for 4 hours at 500C, ammonium exchanged and
then converted to the hydrogen form, was subjected to the sorption
test. Significant n-hexane, i.e. 8 weight percent at 9ûC, was
sorbed while only minimal cyclohexane (about 1 weight percent at
9ûC) sorbed at 8û torr hexane partial pressure. This indicates
molecular shape selectivity for the ZSM-58 of this invention.
EXAM~LE 8
The sample of Example 4 product used for sorption
evaluation was evaluated in the Alpha Test. Its Alpha Value proved
to be 13 at 538C.
lZ~3~1
F-3 513 --15--
EXAMPLE 9
A feedstock comprising methanol was passed over 1.0
gram of hydrogen-form ZSM-58 product of Example 7 at conversion
conditions including atmospheric pressure, 371C and 4 hr 1
WHSV. Conversion of the methanol was 100% with reaction
product components listed below:
Component wt. %
lo Methane 2.6
Ethane 1.5
Ethylene 5.2
Propane 14.8
Propylene 15.8
i-Butane 1.7
n-Butane 2.1
Butenes 24.8
C5 Paraffins & Olefins (P&0) 1.2
C6 P&0 14.7
C7 P&û 7.7
C8 P&0 5.9
Cg P&0 0.7
Benzene 0.1
Toluene 0 3
Xylenes 0.6
Cg Aromatics 0.3
The product from this conversion reaction demonstrates
utility for manufacture of a wide range of useful products.
For instance, 4.1 wt. % Cl-C2 paraffins, useful as fuel
gas, were formed. The product included 18.6 wt. % C3-C4
paraffins, useful as LPG, and 45.8 wt. % C2-C4 olefins,
useful as petrochemicals. The product also contained 31.5 wt.
% C5 + gasoline components.
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