CA1286321C - Oxygenate conversion process - Google Patents

Abstract

AN OXYGENATE CONVERSION PROCESS

ABSTRACT

A process for converting a feedstock comprising organic compounds selected from the group consisting of alcohol, carbonyl, ether and mixtures thereof to a conversion product comprising hydrocarbon compounds comprises contacting the feedstock at conversion conditions with a catalyst composition comprising a crystalline zeolite having a distinctive X-ray diffraction pattern and designated as ZSM-58.

Description

lZ8632i 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 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 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.

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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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 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.

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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 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 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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lZ13~3Zl 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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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 (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 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 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 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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Claims (2)

1. 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:

2). The process of claim 1 wherein said conversion conditions include a temperature of 150-600°C, a pressure of 50-5065 kPa, and a weight hourly space velocity of 0?5-100.