WO2005016855A2 - Supported ionic liquid and the use thereof in the disproportionation of isopentane - Google Patents

Supported ionic liquid and the use thereof in the disproportionation of isopentane Download PDF

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Publication number
WO2005016855A2
WO2005016855A2 PCT/US2004/021041 US2004021041W WO2005016855A2 WO 2005016855 A2 WO2005016855 A2 WO 2005016855A2 US 2004021041 W US2004021041 W US 2004021041W WO 2005016855 A2 WO2005016855 A2 WO 2005016855A2
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accordance
catalyst system
ionic liquid
support
group
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WO2005016855A3 (en
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Bruce B. Randolph
Edward L. Sughrue
Glenn W. Dodwell
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ConocoPhillips Co
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ConocoPhillips Co
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
    • B01J31/0294—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate by polar or ionic interaction with the substrate, e.g. glass
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • B01J31/30—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
    • C07C6/10—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond in hydrocarbons containing no six-membered aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/52—Isomerisation reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/64—Pore diameter
    • B01J35/647—2-50 nm
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica

Definitions

  • the invention relates to catalyst systems useful in hydrocarbon upgrading processes and to methods for their use.
  • this invention relates to processes for the disproportionation of a C 5 paraffin. It is known that ionic liquids can be used in various hydrocarbon conversion processes. However, we have found an ionic liquid dispersed on a support having an average pore diameter greater than about 225 angstroms is unexpectedly effective at disproportionating isopentane.
  • the inventive catalyst system comprises an ionic liquid dispersed on a support having an average pore diameter greater than about 225 angstroms.
  • the inventive catalyst system can be used in the disproportionation of a C 5 paraffin by contacting a C 5 paraffin, under conversion conditions, with the inventive catalyst system.
  • the hydrocarbon feed stream ofthe process of this invention can be any hydrocarbon-containing mixture that comprises at least one C 5 paraffin such as n-pentane, 2-methylbutane, neopentane, or mixtures thereof, and an initiator selected from the group consisting of an olefin, alkyl halides, and combinations thereof.
  • the olefin or alkyl halide preferably has in the range of from 2 to 20 carbon atoms per molecule, more preferably has in the range of from 3 to 6 carbon atoms per molecule, and most preferably has in the range of from 4 to 5 carbon atoms per molecule.
  • the feed contains more than about 50 weight-percent C 5 paraffin, preferably about 60-100 weight percent C 5 paraffin, and more preferably about 75 - 90 weight percent C 5 paraffin.
  • the feed can contain other hydrocarbons that do not interfere with the process of this invention, i.e. minor amounts of other alkanes, such as n-butane, isobutane, n- hexane and the like, and alkenes (monoolefins).
  • the inventive catalyst system comprises, consists of, or consists essentially of an ionic liquid dispersed on a support having an average pore diameter greater than about 225 angstroms, preferably greater than about 250 angstroms, and more preferably greater than about 275 angstroms.
  • the support preferably has a surface area less than about 700 m per gram and is preferably non-crystalline.
  • the support is most preferably a silica.
  • the ionic liquid comprises, consists of, or consists essentially of a cation and an anion.
  • the cation is preferably selected from the group consisting of ions defined by the formulas:
  • Ri, R 2 , R 3 , R 5 , R ⁇ and R 7 are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule;
  • R 4 , R 8 , R 9 , Rio, Rn, R ⁇ 2 , R ⁇ 3 , R ⁇ 4 , R ⁇ 5 , R ⁇ 6 , R ⁇ , R ⁇ 8 and R 19 are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule, and hydrogen.
  • the anion is selected from the group consisting of halides of: Group IIIA metals, copper, zinc, iron, phosphorus and combinations thereof.
  • the anion is selected from the group consisting of chlorides of aluminum, gallium, copper, zinc, and iron; fluorides of phosphorus and boron, and combinations thereof.
  • the inventive process comprises, consists of, or consists essentially of, a) contacting, under conversion conditions, the hydrocarbon feed stream with the inventive catalyst system; and b) withdrawing a product stream comprising a C 4 paraffin which is preferably isobutane and at least one C 6 paraffin which is preferably a hexane isomer.
  • the conversion conditions include a temperature in the range of from about 37.7°C to about 537.7°C (about 100°F to about 1000°F), preferably in the range of from about 60°C to about 121 °C (about 140°F to about 250°F), and more preferably in the range of from about 65.5°C to about 104°C (about 150°F to about 220°F).
  • a temperature in the range of from about 37.7°C to about 537.7°C (about 100°F to about 1000°F), preferably in the range of from about 60°C to about 121 °C (about 140°F to about 250°F), and more preferably in the range of from about 65.5°C to about 104°C (about 150°F to about 220°F).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

A catalyst system containing an ionic liquid dispersed on a support having an average pore diameter greater than about 225Å is disclosed. The catalyst system is employed in a process to disproportionate a C5 paraffin.

Description

SUPPORTED IONIC LIQUID AND THE USE THEREOF LN THE DISPROPORTIONATION OF ISOPENTANE The invention relates to catalyst systems useful in hydrocarbon upgrading processes and to methods for their use. In another aspect, this invention relates to processes for the disproportionation of a C5 paraffin. It is known that ionic liquids can be used in various hydrocarbon conversion processes. However, we have found an ionic liquid dispersed on a support having an average pore diameter greater than about 225 angstroms is unexpectedly effective at disproportionating isopentane. The phrases "consists essentially of and "consisting essentially of do not exclude the presence of other steps, elements, or materials that are not specifically mentioned in this specification, as long as such steps, elements or materials, do not affect the basic and novel characteristics ofthe invention, additionally, they do not exclude impurities normally associated with the elements and materials used. The above terms and phrases are intended for use in areas outside of U.S. jurisdiction. Within the U.S. jurisdiction the above terms and phrases are to be applied as they are construed by U.S. courts and the U.S. Patent Office. It is desirable to provide an improved supported ionic liquid which when used in the disproportionation of a C5 paraffin results in increased product formation. Again it is desirable to provide an improved process for the disproportionation of a C5 paraffin in which the yield of disproportionation products is increased. The inventive catalyst system comprises an ionic liquid dispersed on a support having an average pore diameter greater than about 225 angstroms. The inventive catalyst system can be used in the disproportionation of a C5 paraffin by contacting a C5 paraffin, under conversion conditions, with the inventive catalyst system. Other objects and advantages of the invention will become apparent from the detailed description and the appended claims. The hydrocarbon feed stream ofthe process of this invention can be any hydrocarbon-containing mixture that comprises at least one C5 paraffin such as n-pentane, 2-methylbutane, neopentane, or mixtures thereof, and an initiator selected from the group consisting of an olefin, alkyl halides, and combinations thereof. The olefin or alkyl halide preferably has in the range of from 2 to 20 carbon atoms per molecule, more preferably has in the range of from 3 to 6 carbon atoms per molecule, and most preferably has in the range of from 4 to 5 carbon atoms per molecule. Generally, the feed contains more than about 50 weight-percent C5 paraffin, preferably about 60-100 weight percent C5 paraffin, and more preferably about 75 - 90 weight percent C5 paraffin. The feed can contain other hydrocarbons that do not interfere with the process of this invention, i.e. minor amounts of other alkanes, such as n-butane, isobutane, n- hexane and the like, and alkenes (monoolefins). The inventive catalyst system comprises, consists of, or consists essentially of an ionic liquid dispersed on a support having an average pore diameter greater than about 225 angstroms, preferably greater than about 250 angstroms, and more preferably greater than about 275 angstroms. The support preferably has a surface area less than about 700 m per gram and is preferably non-crystalline. The support is most preferably a silica. The ionic liquid comprises, consists of, or consists essentially of a cation and an anion. The cation is preferably selected from the group consisting of ions defined by the formulas:
Figure imgf000003_0001
Figure imgf000003_0002
Figure imgf000004_0001
and combinations of any two or more thereof wherein: Ri, R2, R3, R5, Rό and R7 are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule; R4, R8, R9, Rio, Rn, Rι2, Rι3, Rι4, Rι5, Rι6, Rπ, Rι8 and R19 are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule, and hydrogen. The anion is selected from the group consisting of halides of: Group IIIA metals, copper, zinc, iron, phosphorus and combinations thereof. More preferably, the anion is selected from the group consisting of chlorides of aluminum, gallium, copper, zinc, and iron; fluorides of phosphorus and boron, and combinations thereof. The ionic liquid preferably has the general formula Ri R2 R3 N H + Aln wherein n = 1, 2, or 3; and more preferably has the general formula (CH3)3 N H +A12 Cl7 ". The inventive process comprises, consists of, or consists essentially of, a) contacting, under conversion conditions, the hydrocarbon feed stream with the inventive catalyst system; and b) withdrawing a product stream comprising a C4 paraffin which is preferably isobutane and at least one C6 paraffin which is preferably a hexane isomer. The conversion conditions include a temperature in the range of from about 37.7°C to about 537.7°C (about 100°F to about 1000°F), preferably in the range of from about 60°C to about 121 °C (about 140°F to about 250°F), and more preferably in the range of from about 65.5°C to about 104°C (about 150°F to about 220°F). The following examples are presented to further illustrate this invention and are not to be construed as unduly limiting its scope. EXAMPLE I For Inventive Run 1, 7.38 grams of A1C1 were mixed with 2.71 grams of trimethylammonium chloride (N(CH3)3:HCI) (at approximately 2 equivalents A1C1 and 1 equivalent (N(CH3)3:HC1)) to form an ionic liquid. A 1.98 gram quantity of silica spheres, having a surface area greater than about 400 m2/g, a pore volume of 3.0 cc/g, and an average pore diameter of 308 A , were added to the ionic liquid along with 17.01 grams of the inert support Alundum alumina to form a mixture. The mixture was then charged to a reactor. An isopentane feed was charged to the reactor at varying reactor temperatures and liquid hourly space velocities. Results of such are presented in Table 1.
Figure imgf000006_0001
The data in Table I demonstrate that a catalyst system including an ionic liquid dispersed on silica spheres having an average pore diameter greater than about 225A (specifically, 308A) results in significant isopentane conversion, with even higher conversions at reactor temperatures in excess of 65.5 °C (150T). For Runs 2 through 5, the catalysts were made from about 2 equivalents A1C13 and about 1 equivalent N(CH3)3:HC1 to generate an ionic liquid to which silica supports were added, as shown in Table II. An isopentane feed comprising about 98.2 - 98.4 wt. % isopentane, about 0.8 - 1.4 wt. % C5 = ; ~ 0.2 wt. % neo C5 = and about 0.13 - 0.15 wt. % C4 paraffins, was charged to each reactor at an LHSV of 2 hr."1. Results ofthe conversions are presented in Table II. TABLE II
Figure imgf000007_0001
The data in Table II demonstrate that ionic liquid catalyst systems which have silica supports with higher average pore diameters result in higher isopentane conversion as compared to ionic liquid catalyst systems which have lower average pore diameter silica supports. For Inventive Run 6, 2.19 grams of N(CH3)3:HC1 were added to 7.92 grams of GaCl3 to form an ionic liquid. A 2.05 gram quantity of silica spheres, having a surface area greater than about 400 m /g, a pore volume of 3.0 cc/g, and an average pore diameter of 308 A , were added to the ionic liquid along with 17.94 grams of Alundum alumina to form a mixture. The mixture was then charged to a reactor. An isopentane feed, as shown in Table HI, was charged to the reactor. Results of such are presented in Table ILL TABLE III
Figure imgf000008_0001

Claims

C L A I M S
1. A catalyst system comprising an ionic liquid dispersed on a support having an average pore diameter greater than about 225 A.
2. A catalyst system in accordance with claim 1, wherein said support has a surface area less than about 700 m /gram.
3. A catalyst system in accordance with claim 1, wherein said support is non-crystalline.
4. A catalyst system in accordance with claim 1, wherein said support is non-crystalline and has a surface area less than about 700 m2/gram.
5. A catalyst system in accordance with claim 1, wherein said support is silica.
6. A catalyst system in accordance with claim 1, wherein said ionic liquid comprises a cation and an anion; wherein said cation is selected from the group consisting of ions defined by the formulas:
Figure imgf000009_0001
Figure imgf000009_0002
and combinations of any two or more thereof, wherein: Ri, R2, R3, R5, R6, and R7 are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule; 4> Rβ, R°> RiO) ib Ri2, i3» RH, ι5) Rι6; i7j i8> and R]9 are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule, and hydrogen; and wherein said anion is selected from the group consisting of halides of: Group IIIA metals, copper, zinc, iron and phosphorus.
7. A catalyst system in accordance with claim 6, wherein said anion is selected from the group consisting of A1C14 ", A12C17 ", Al3Clι0 ", GaCLf, Ga2Cl7 ",
Ga3Clιo", CuCl2 ", Cu2Cl3 ", Cu3Cl4 ", ZnCl3\ FeCl3 ", FeCl4 ", Fe3Cl7 ", PF6 ", and BF4 ".
8. A catalyst system in accordance with claim 6, wherein said ionic liquid has the formula R1R2R3NH+A12C17 ".
9. A catalyst system in accordance with claim 6, wherein said ionic liquid has the formula (CH3)3NH+Ai2ClJ.
10. A catalyst system in accordance with claim 1, wherein a Group VIII metal compound is dispersed in said ionic liquid.
11. A catalyst system in accordance with claim 10, wherein said Group VIII metal compound comprises a platinum compound.
12. A process comprising: a) contacting, under conversion conditions, a hydrocarbon feed stream comprising a C5 paraffin and an initiator with a catalyst system comprising an ionic liquid dispersed on a support; and b) withdrawing a product stream comprising a C4 paraffin and at least one C6 paraffin.
13. A process in accordance with claim 12, wherein said support has an average pore diameter greater than about 225 A.
14. A process in accordance with claim 12, wherein said support has a surface area less than about 700 m2/gram.
15. A process in accordance with claim 12, wherein said support is non-crystalline.
16. A process in accordance with claim 12, wherein said support is non-crystalline, has an average pore diameter greater than about 225 A, and has a surface area less than about 700 m2/gram.
17. A process in accordance with claim 12, wherein said support is silica.
18. A process in accordance with claim 12, wherein said ionic liquid comprises a cation and an anion; wherein said cation is selected from the group consisting of ions defined by the formulas:
Figure imgf000011_0001
Figure imgf000011_0002
and combinations of any two or more thereof, wherein: Ri, R , R3, R5, R , and R7 are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule; R4, R&, R9, Rio, Rib Rπ> Ri3> Ri4, ι5> Ri6,
Figure imgf000012_0001
Ri8> ar»d Rι are selected from saturated and unsaturated hydrocarbons containing from 1 to 7 carbon atoms per molecule, and hydrogen; and wherein said anion is selected from the group consisting of halides of: Group IIIA metals, copper, zinc, iron and phosphorus.
19. A process in accordance with claim 18, wherein said anion is selected from the groups consisting of AlCLf, A12C17 ", Al3Clιo", GaClJ, Ga2OJ, Ga3Clι0\ CuClJ, Cu2Cl3 ", Cu3Cι4-, ZnCLJ, FeCl3\ FeCLf, Fe3Cl7\ PF6 ", and BF4\
20. A process in accordance with claim 18, wherein said ionic liquid has the formula R, R2R3NH+A12C17 ".
21. A process in accordance with claim 18, wherein said ionic liquid has the formula (CH3)3NH+A12C1 .
22. A process in accordance with claim 12, wherein said hydrocarbon feed stream comprises at least 50 weight-% isopentane, based on the total weight of said hydrocarbon feed stream.
23. A process in accordance with claim 12, wherein said hydrocarbon feed stream comprises in the range of from about 50 to about 95 weight-% isopentane, based on the total weight of said hydrocarbon feed stream.
24. A process in accordance with claim 12, wherein said hydrocarbon feed stream comprises in the range of from about 80 to about 98.5 weight- % isopentane, based on the total weight of said hydrocarbon feed stream.
25. A process in accordance with claim 12, wherein said conversion conditions include a temperature in the range of from about 37.7 °C to about 537.7°C (about 100°F to about 1000°F).
26. A process in accordance with claim 12, wherein said conversion conditions include a temperature in the range of from about 60 °C to about 121 °C (about 140°F to about 250°F).
27. A process in accordance with claim 12, wherein said conversion conditions include a temperature in the range of from about 65.5 °C to about 104°C (about 150°F to about 220°F).
28. A process in accordance with claim 12, wherein said C4 paraffin of said product stream is isobutane and said C6 paraffin of said product stream is a hexane isomer.
29. A process in accordance with claim 12, wherein said initiator is selected from the group consisting of: 1) an olefin having in the range of from 2 to 20 carbon atoms per molecule, 2) an alkyl halide wherein said alkyl halide has in the range of from 2 to 20 carbon atoms per molecule, and combinations thereof
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US12172148B2 (en) 2011-10-19 2024-12-24 Sud Chemie, Inc. Catalyst composition for selective hydrogenation with improved characteristics
US12172147B2 (en) 2011-10-19 2024-12-24 Sud Chemie, Inc. Catalyst composition for selective hydrogenation with improved characteristics

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