CA2547187A1 - Zirconia containing support material for catalysts - Google Patents

Zirconia containing support material for catalysts Download PDF

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Publication number
CA2547187A1
CA2547187A1 CA002547187A CA2547187A CA2547187A1 CA 2547187 A1 CA2547187 A1 CA 2547187A1 CA 002547187 A CA002547187 A CA 002547187A CA 2547187 A CA2547187 A CA 2547187A CA 2547187 A1 CA2547187 A1 CA 2547187A1
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Prior art keywords
catalyst
palladium
support material
gold
composition
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CA002547187A
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French (fr)
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CA2547187C (en
Inventor
Tao Wang
Leslie E. Wade
Victor Wong
David M. Lowe
Alfred Hagemeyer
Jun Han
Valery Sokolovskii
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Celanese International Corp
Original Assignee
Celanese International Corporation
Tao Wang
Leslie E. Wade
Victor Wong
David M. Lowe
Alfred Hagemeyer
Jun Han
Valery Sokolovskii
Symyx Technologies, Inc.
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Application filed by Celanese International Corporation, Tao Wang, Leslie E. Wade, Victor Wong, David M. Lowe, Alfred Hagemeyer, Jun Han, Valery Sokolovskii, Symyx Technologies, Inc. filed Critical Celanese International Corporation
Publication of CA2547187A1 publication Critical patent/CA2547187A1/en
Application granted granted Critical
Publication of CA2547187C publication Critical patent/CA2547187C/en
Expired - Fee Related legal-status Critical Current
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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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/48—Silver or gold
    • B01J23/52—Gold
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/007—Mixed salts
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • 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
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • 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
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • B01J37/18—Reducing with gases containing free hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
    • C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
    • 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
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/396—Distribution of the active metal ingredient
    • B01J35/397—Egg shell like
    • 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
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/396—Distribution of the active metal ingredient
    • B01J35/398—Egg yolk like
    • 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
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/396—Distribution of the active metal ingredient
    • B01J35/399—Distribution of the active metal ingredient homogeneously throughout the support particle
    • 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
    • B01J35/61—Surface area
    • B01J35/612—Surface area less than 10 m2/g
    • 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
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • 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
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention addresses at aeast four different aspects relating to catalyat structure, method of making those catalysts and methods of using those catalysts for making allcenyl alkanoates. Separately or together in combination, the various aspects of the invention are directed at improving the production of alkenyl alkanoates and VA in particular, including reduction of by-products and improved production efficiency. A first aspect of the presente invention pertains to a unique palladium/gold catalyst or pre-catalyst (optionally calcined) that includes rhodium or another metal. A
second aspect pertains to a palladium/gold catalyst or precatalyst at is based on a layered support material where one layer of the support materiel is substantially free of catalytic components. A third aspect pertains to a palladium/gold catalyst or precatalysts on a zirconia containing support material. A fourth aspect pertains to a palladium gold catalyst or pre-catalyst that is produced from substantially chloride free catalytic components.

Claims (52)

1. A method of producing a catalyst or pre-catalyst suitable for assisting in the production of alkenyl alkanoates, comprising:
contacting palladium and gold precursors to a zirconia containing support material; and reducing at least the palladium precursor by contacting a reducing environment to the zirconia containing support material.
2. The method of claim 1, wherein the zirconia containing support material has a BET
surface area of between about 5 m2/g and about 300 m2/g.
3. The method of either claims 1 or 2, wherein the zirconia containing support material has a particle size of between 5 µm and about 10 mm.
4. The method of any of claims 1-3, further comprising calcining the contacted zirconia containing support material in a non-reducing atmosphere before the reducing step.
5. The method of any of claims 1-4, wherein the contacting step comprises impregnating the zirconia containing support material with palladium and gold precursors.
6. The method of any of claims 1-5, wherein the impregnating step comprises sequentially impregnating palladium and gold precursors onto the zirconia containing support material.
7. The method of any of claims 1-6, wherein the calcining step occurs before the impregnation of the gold precursor.
8. The method of any of claims 1-7, further comprising at least one fixing step utilizing a fixing agent.
9. The method of any of claims 1-8, wherein the reducing step occurs before the impregnating of the gold precursor.
10. The method of any of claims 1-9, wherein the impregnating step comprises co-impregnating palladium and gold precursors.
11. The method of any of claims 1-10, wherein the impregnating step comprises impregnating the zirconia containing support material with water soluble, substantially chloride free precursor solutions.
12. The method of any of claims 1-11, wherein the substantially chloride free precursors of palladium comprise Pd(NH3)2(NO2)2, Pd(NH3)4(OH)2, Pd(NH3)4(NO3)a, Pd(N03)2, Pd(NH3)4(OAc)2, Pd(NH3)2(OAc)2, Pd(OAc)2 in KOH or NMe4OH or NaOH, Pd(NH3)4(HCO3)2, palladium oxalate or combinations thereof.
13. The method of any of claims 1-12, wherein the substantially chloride free precursors of gold comprise KAuO2, NaAuO2, NMe4AuO2, Au(OAc)3 in KOH or NMe4OH, HAu(NO3)4 in nitric acid or combinations thereof.
14. The method of any of claims 1-13, wherein the impregnating step comprises impregnating the zirconia containing support material with chloride containing precursor solutions and following by a fixing step comprising fixing with a fixing agent.
15. The method of any of claims 1-14, wherein the contacting step further comprises contacting a third component precursor.
16. The method of any of claims 1-15, wherein the third component precursor comprises W, Ni, Nb, Ta, Ti, Zr, Y, Re, Os, Fe, Cu, Co, Zn, In, Sn, Ce, Ge, Rh, Ga and combinations thereof.
17. The method of any of claims 1-16, wherein the contacting step comprises contacting the third component and palladium in a third component to palladium atomic ratio of between about 0.01 and about 0.5.
18. The method of any of claims 1-17, wherein the calcining step comprises heating the contacted zirconia containing support material at a temperature between about 200°C and about 700°C.
19. The method of any of claims 1-18, wherein the zirconia containing support material comprises a layered support material.
20. The method of any of claims 1-19, wherein the layered support material comprises an outer layer with a thickness of between about 5 and about 300 microns.
21. The method of any of claims 1-20, further comprising contacting an alkali metal acetate to the zirconia containing support material.
22. The method of any of claims 1-21, wherein the alkali metal acetate is potassium acetate.
23. The method of any of claims 1-22, wherein the potassium acetate is present in an amount of between about 10 and 70 grams per liter of catalyst
24. The method of any of claims 1-23, wherein the contacting step comprises contacting between about 1 to about 10 grams of palladium, and about 0.5 to about 10 grams of gold per liter of catalyst, with the amount of gold being from about 10 to about 125 wt% based on the weight of palladium.
25. The method of any of claims 1-24, wherein the atomic ratio of gold to palladium is between about 0.50 and about 1.00.
26. The method of any of claims 1-25, wherein the steps of the method result in a shell catalyst or pre-catalyst, an egg yolk catalyst or pre-catalyst, an egg white catalyst or pre-catalyst, or an all-throughout catalyst or pre-catalyst.
27. The method of any of claims 1-26, wherein the steps of the method result in a shell catalyst or pre-catalyst, the shell results from a layered support material, physical shell formation or chemical shell formation.
28. The method of any of claims 1-27, wherein the shell has thickness between about 5 and about 300 microns.
29. A composition for catalyzing the production of an alkenyl alkanoates, comprising:
a zirconia containing support material with at least palladium and gold contacted thereon to forth a catalyst or pre-catalyst.
30. The composition of claim 29, wherein the zirconia containing support material comprises a layered support material.
31. 2930The composition of any of claims 29-31, wherein the palladium and gold have been calcined.
32. The composition of any of claims 29-32, wherein the palladium and gold have been reduced.
33. The composition of any of claims 29-33, wherein the gold has not been calcined before being reduced.
34. The composition of any of claim 29-33, wherein the gold has not been reduced.
35. The composition of any of claims 29-34, wherein the catalyst or pre-catalyst comprises a third component.
36. The composition of any of claims 29-35, wherein the third component is selected from W, Ni, Nb, Ta, Ti, Zr, Y, Re, Os, Fe, Cu, Co, Zn, In, Sn, Ce, Ge, Rh, Ga and combinations thereof.
37. The composition of any of claims 29-36, wherein the third component to palladium atomic ratio of between about 0.01 and about 0.5.
38. The composition of any of claims 29-37, wherein the catalyst or pre-catalyst comprises between about 1 to about 10 grams of palladium, and about 0.5 to about 10 grams of gold per liter of catalyst, with the amount of gold being from about 10 to about 125 wt% based on the weight of palladium.
39. The composition of any of claims 29-38, wherein the catalyst or pre-catalyst comprises an alkali metal acetate.
40. The composition of any of claims 29-39, wherein the alkali metal acetate is potassium acetate.
41. The composition of any of claims 29-40, wherein the potassium acetate is present in an amount of between about 10 and 70 grams per liter of catalyst.
42. The composition of any of claims 29-41, wherein the catalyst or pre-catalyst comprises a shell catalyst or pre-catalyst, an egg yolk catalyst or pre-catalyst, an egg white catalyst or pre-catalyst, or an all-throughout catalyst or pre-catalyst.
43. The composition of any of claims 29-42, wherein the zirconia support material comprises particle support material or a ground support material.
44. A method of producing alkenyl alkanoates, comprising:
contacting a feed comprising an alkene, an alkanoic acid and an oxidizer to a catalyst or pre-catalyst comprising palladium and gold on a zirconia containing support material.
45. The method of claim 44, wherein the alkene is ethylene, the alkanoic acid is acetic acid and the oxidizer is an oxygen containing gas.
46. The method of either claims 44 or 45, wherein the catalyst or pre-catalyst comprises a third component.
47. The method of any of claims 44-46, wherein the third component is selected from W, Ni, Nb, Ta, Ti, Zr, Y, Re, Os, Fe, Cu, Co, Zn, In, Sn, Ce, Ge, Rh, Ga and combinations thereof.
48. The method of any of claims 44-47, wherein the catalyst or pre-catalyst comprises a third component and palladium in a third component to palladium atomic ratio of between about 0.01 and about 0.5.
49. The method of any of claims 44-48, wherein the catalyst or pre-catalyst comprises between about 1 to about 10 grams of palladium, and about 0.5 to about 10 grams of gold per liter of catalyst, with the amount of gold being from about 10 to about 125 wt% based on the weight of palladium.
50. The method of any of claims 44-49, wherein the zirconia containing support material comprises a layered support material.
51. The method of any of claims 44-50, wherein the zirconia containing support material comprises silica, alumina, silica-alumina, titania, niobia, silicates, aluminosilicates, titanates, spinel, silicon carbide, silicon nitride, carbon, steatite, bentonite, clays, metals, glasses, quartz, pumice, zeolites, non-zeolitic molecular sieves, or combinations thereof.
52. The method of any of claims 44-51, wherein the catalyst or pre-catalyst is a shell catalyst or pre-catalyst, an egg yolk catalyst or pre-catalyst, egg white catalyst or pre-catalyst, or an all throughout catalyst or pre-catalyst.
CA2547187A 2003-12-19 2004-11-19 Zirconia containing support material for catalysts Expired - Fee Related CA2547187C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US53148603P 2003-12-19 2003-12-19
US60/531,486 2003-12-19
PCT/US2004/039039 WO2005061107A1 (en) 2003-12-19 2004-11-19 Zirconia containing support material for catalysts

Publications (2)

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CA2547187A1 true CA2547187A1 (en) 2005-07-07
CA2547187C CA2547187C (en) 2010-11-02

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EP (1) EP1694436A1 (en)
JP (1) JP4772695B2 (en)
KR (1) KR100886048B1 (en)
CN (1) CN100457257C (en)
AU (1) AU2004305515C1 (en)
BR (1) BRPI0417185A (en)
CA (1) CA2547187C (en)
NO (1) NO20062531L (en)
NZ (1) NZ547072A (en)
PL (1) PL215127B1 (en)
RU (2) RU2006119185A (en)
UA (1) UA96563C2 (en)
WO (1) WO2005061107A1 (en)
ZA (1) ZA200604362B (en)

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CA2547187C (en) 2010-11-02
CN1894035A (en) 2007-01-10
RU2006119185A (en) 2007-12-20
NO20062531L (en) 2006-07-03
BRPI0417185A (en) 2007-03-06
PL380021A1 (en) 2006-12-11
JP4772695B2 (en) 2011-09-14
EP1694436A1 (en) 2006-08-30
AU2004305515A1 (en) 2005-07-07
KR20060103514A (en) 2006-10-02
PL215127B1 (en) 2013-10-31
AU2004305515B2 (en) 2008-08-28
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