WO1999043430B1 - Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions - Google Patents

Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions

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Publication number
WO1999043430B1
WO1999043430B1 PCT/US1999/003402 US9903402W WO9943430B1 WO 1999043430 B1 WO1999043430 B1 WO 1999043430B1 US 9903402 W US9903402 W US 9903402W WO 9943430 B1 WO9943430 B1 WO 9943430B1
Authority
WO
WIPO (PCT)
Prior art keywords
oxidation catalyst
noble metal
promoter
catalyst
atoms
Prior art date
Application number
PCT/US1999/003402
Other languages
French (fr)
Other versions
WO1999043430A1 (en
WO1999043430A8 (en
WO1999043430A9 (en
Inventor
Jerry R Ebner
Mark A Leiber
Kam-To Wan
Anthony Woods
Peter E Rogers
Original Assignee
Monsanto Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to AU27707/99A priority Critical patent/AU761345B2/en
Priority to EA200000869A priority patent/EA200000869A1/en
Priority to IL13808199A priority patent/IL138081A0/en
Priority to SK1256-2000A priority patent/SK12562000A3/en
Priority to KR1020007009463A priority patent/KR20010041349A/en
Priority to JP2000533219A priority patent/JP2002504427A/en
Priority to HU0101891A priority patent/HUP0101891A3/en
Priority to CA002321923A priority patent/CA2321923C/en
Priority to BRPI9908252-7A priority patent/BRPI9908252B1/en
Priority to EP99908217A priority patent/EP1060017A1/en
Publication of WO1999043430A1 publication Critical patent/WO1999043430A1/en
Publication of WO1999043430B1 publication Critical patent/WO1999043430B1/en
Publication of WO1999043430A8 publication Critical patent/WO1999043430A8/en
Publication of WO1999043430A9 publication Critical patent/WO1999043430A9/en

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Classifications

    • 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
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • 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
    • B01J21/18—Carbon
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Abstract

This invention relates to an improved catalyst, comprising a carbon support having a noble metal at its surface, for use in catalyzing liquid phase oxidation reactions, especially in an acidic oxidative environment and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; a process for the preparation of the improved catalyst; a liquid phase oxidation process using such a catalyst wherein the catalyst exhibits improved resistance to noble metal leaching, particularly in acidic oxidative environments and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; and a liquid phase oxidation process in which N-(phosphonomethyl)iminodiacetic acid (i.e., 'PMIDA') or a salt thereof is oxidized to form N-(phosphonomethyl)glycine (i.e., 'glyphosate') or a salt thereof using such a catalyst wherein the oxidation of the formaldehyde and formic acid by-products into carbon dioxide and water is increased.

Claims

AMENDED CLAIMS
[received by the International Bureau on 07 September 1999 (07.09.99); original claims 1, 4, 11, 18, 25, 38, 43, 50, 63, 68, 75, 88, 95, 125,
134-139, 146, 151 and 158 amended; remaining claims unchanged (15 pages)]
1. An oxidation catalyst comprising a non-graphitic carbon support having a noble metal at a surface of the non- graphitic carbon support, the catalyst being characterized as yielding no more than about 0.7 mmole of carbon monoxide per gram of catalyst when a dry sample of the catalyst in a helium atmosphere is heated from about 20 to about 900"C at a rate of about 10°C per minute, and then at about 900°C for about 30 minutes.
2. The oxidation catalyst of claim 1 wherein said carbon monoxide yield is no greater than about 0.5 mmole of carbon monoxide per gram of catalyst.
3. The oxidation catalyst of claim 1 wherein said carbon monoxide yield is no greater than about 0.3 mmole of carbon monoxide per gram of catalyst.
4. An oxidation catalyst comprising a non-graphitic carbon support having a noble metal and a promoter at a surf ce of the non-graphitic carbon suppor , the catalyst being characterized as yielding no more than about 0.7 mmole of carbon monoxide per gram of catalyst when a dry sample of the catalyst, after being heated at a temperature of about 500°C for about 1 hour in a hydrogen atmosphere and before being exposed to an oxidant following the heating in the hydrogen atmosphere, is heated in a helium atmosphere from about 20 to about 900βC at a rate of about 10°C per minute, and then at about 900°C for about 30 minutes.
5. The oxidation catalyst of claim 4 wherein at least 0.05% by weight of the catalyst consists of at least one promoter .
142
6. The oxidation catalyst of claim 4 wherein the promoter is more easily oxidized than the noble metal.
7. The oxidation catalyst of claim 4 wherein the promoter comprises a metal selected from the group consisting of tin, bismuth, lead, cadmium, magnesium, manganese, nickel, aluminum, cobalt, titanium, antimony, selenium, iron, rhenium, cerium, zinc, and zirconium.
8. The oxidation catalyst of claim 4 wherein the promoter comprises tin.
9. The oxidation catalyst of claim 4 wherein the promoter comprises iron.
10. The oxidation catalyst of claim 4 wherein the promoter comprises titanium.
11. The oxidation catalyst of claim 4 wherein at least two promoters are at the surface of the non-graphitic carbon support .
12. The oxidation catalyst of claim 11 wherein the promoters comprise iron and tin.
13. The oxidation catalyst of claim 4 wherein noble metal atoms at the surface are alloyed with the promoter.
14. The oxidation catalyst of claim 4 wherein a majority of the noble metal atoms at the surface are alloyed with the promoter,
15. The oxidation catalyst of claim 4 wherein substantially all of the noble metal atoms at the surface are alloyed with the promoter.
16. The oxidation catalyst of claim 4 wherein said carbon monoxide yield is no greater than about 0.5 mmole of carbon monoxide per gram of catalyst .
17. The oxidation catalyst of claim 4 wherein said carbon monoxide yield is no greater than about 0.3 mmole of carbon monoxide per gram of catalyst.
18. An oxidation catalyst comprising a non-graphitic carbon support having a noble metal, carbon, aid oxygen at a surface of the non-graphitic carbon support, wherein the ratio of carbon atoms to oxygen atoms at the surface is at least about 30:1 as measured by x-ray photoelectron spectroscopy.
19. The oxidation catalyst of claim 18 wherein said ratio of carbon atoms to oxygen atoms is at least about 40:1.
20. The oxidation catalyst of claim 18 wherein said ratio of carbon atoms to oxygen atoms is at least about 50:1.
21. The oxidation catalyst of claim 18 wherein said ratio of carbon atoms to oxygen atoms is at least about 60:1.
22. The oxidation catalyst of claim 18 wherein the ratio of oxygen atoms to noble metal atoms at the surface is less than 7:1 as measured by x-ray photoelectron spectroscopy.
144
23. The oxidation catalyst of claim 22 wherein said ratio of oxygen atoms to noble metal atoms is lees than about
6:1.
24. The oxidation catalyst of claim 22 wherein said ratio of oxygen atoms to noble metal atoms is less than about 5:1.
25. An oxidation catalyst comprising a non-graphitic carbon support having a noble metal, a promoter, carbon, and oxygen at a surface of the non-graphitic carbon support, wherein the catalyst is characterized as having a ratio of carbon atoms to oxygen atoms of at least about 30:1 at the surface as measured by x-ray photoelectron spectroscopy after the catalyst is heated at a temperature of about 500°C for about 1 hour in a hydrogen atmosphere and before the catalyst is exposed to an oxidant following the heating in the hydrogen atmosphere.
26. The oxidation catalyst of claim 25 wherein said ratio of carbon atoms to oxygen atoms is at least about 40:1.
27. The oxidation catalyst of claim 25 wherein said ratio of carbon atoms to oxygen atoms is at least about 50:1.
28. The oxidation catalyst of claim 25 wherein said ratio of carbon atoms to oxygen atoms is at least about 60:1.
29. The oxidation catalyst of claim 25 wherein the catalyst is further characterized as having a ratio of oxygen atoms to noble metal atoms at the surface which is less than 7;l after the catalyst is heated at a temperature of about 500"C for about 1 hour in a hydrogen atmosphere and before the
145
38. The oxidation catalyst of claim 25 wherein at least two promoters are at the surface of the non-graphitic carbon support .
39. The oxidation catalyst of claim 38 wherein the promoters comprise iron and tin.
40. The oxidation catalyst of claim 25 wherein noble metal atoms at the surface are alloyed with the promoter.
41. The oxidation catalyst of claim 25 wherein a majority of the noble metal atoms at the surface are alloyed with the promoter.
42. The oxidation catalyst of claim 25 wherein substantially all of the noble metal atoms at the surface are alloyed with the promoter.
43. An oxidation catalyst comprising a non-graphitic carbon support comprising: a noble metal at a surface of the non-graphitic carbon support ; and a surface layer which (a) has a thickness of about 50 A as measured inwardly from the surface, and (b) comprises oxygen and carbon, the ratio of carbon atoms to oxygen atoms in the surface layer being at least about 30:1.
44. The oxidation catalyst of claim 43 wherein said ratio of carbon atoms to oxygen atoms is at least about 40:1.
45. The oxidation catalyst of claim 43 wherein said ratio of carbon atoms to oxygen atoms is at least about 50:1.
146
46. The oxidation catalyst of claim 43 wherein said ratio of carbon atoms to oxygen atoms is at least about 60:1.
47. The oxidation catalyst of claim 43 wherein the ratio of oxygen atoms to noble metal atoms in the surface layer is less than 7:1 as measured by x-ray photoelectron spectroscopy.
48. The oxidation catalyst of claim 47 wherein said ratio of oxygen atoms to noble metal atoms is less than about 6:1.
49. The oxidation catalyst of claim 47 wherein said ratxo of oxygen atoms to noble metal atoms is less than about 5:1.
50. An oxidation catalyst comprising a non-graphitic carbon support comprising: a noble metal and a promoter at a surface of the non- graphitic carbon support, and a surface layer having a thickness of about 50 A as measured inwardly from the surface and comprising carbon and oxygen, wherein the catalyst is characterized as having a ratio of carbon atoms to oxygen atoms in the surface layer of least about 30:1 as measured by x-ray photoelectron spectroscopy after the catalyst is heated at a temperature of about 500°C for about 1 hour in a hydrogen atmosphere and before the catalyst is exposed to an oxidant following the heating in the hydrogen atmosphere.
51. The oxidation catalyst of claim 50 wherein said ratio of carbon atoms to oxygen atoms is at least about 40:1.
147 of tin, bismuth, lead, cadmium, magnesium, manganese, nickel, aluminum, cobalt, titanium, antimony, selenium, iron, rhenium, cerium, zinc, and zirconium.
60. The oxidation catalyst of claim 50 wherein the promoter comprises tin.
61. The oxidation catalyst of claim 50 wherein the promoter comprises iron.
62. The oxidation catalyst of claim 50 wherein the promoter comprises titanium.
63. The oxidation catalyst of claim 50 wherein at least two promoters are at the surface of the non-graphitic carbon support .
64. The oxidation catalyst of claim 63 wherein the promoters comprise iron and tin,
65. The oxidation catalyst of claim 50 wherein noble metal atoms at the surface are alloyed with the promoter.
66. The oxidation catalyst of claim 50 wherein a majority of the noble metal atoms at the surface are alloyed with the promoter.
67. The oxidation catalyst of claim 50 wherein substantially all of the noble metal atoms at the surface are alloyed with the promoter.
68. An oxidation catalyst prepared by a process comprising depositing a noble metal at a surface of a non- graphitic carbon
148 support, and then heating the surface at a temperature greater than about 500°C.
69. The oxidation catalyst of claim 68 wherein at least 0.05% by weight of the catalyst consists of at least one promoter.
70. The oxidation catalyst of claim 69 wherein the promoter is more easily oxidized than the noble metal.
71. The oxidation catalyst of claim 69 wherein the promoter comprises a metal selected from the group consisting of tin, bismuth, lead, cadmium, magnesium, manganese, nickel, aluminum, cobalt, titanium, antimony, selenium, iron, rhenium, cerium, zinc, and zirconium.
72. The oxidation catalyst of claim 69 wherein the promoter comprises tin.
73. The oxidation catalyst of claim 69 wherein the promoter comprises iron.
74. The oxidation catalyst of claim 69 wherein the promoter comprises titanium.
75. The oxidation catalyst of claim 69 wherein at least two promoters are at the surface of the non-graphitic carbon support .
76. The oxidation catalyst of claim 75 wherein the promoters comprise iron and tin.
149
87. The oxidation catalyst of claim 85 wherein said reducing environment comprises H2.
88. An oxidation catalyst prepared by a process comprising depositing a noble metal at a surface of a non- graphitic carbon support, and then heating the surface at a temperature of at least about 400°C, wherein before the noble metal deposition, the non-graphitic carbon support has carbon and oxygen at the surface of the non-graphitic carbon support in amounts such that the ratio of carbon atoms to oxygen atoms at the surface is at least about 20:1 as measured by x-ray photoelectron spectroscopy.
89. The oxidation catalyst of claim 88 wherein at least 0.05% by weight of the catalyst consists of at least one promoter .
90. The oxidation catalyst of claim 89 wherein the promoter is more easily oxidizied than the noble metal.
91. The oxidation catalyst of claim 89 wherein the promoter comprises a metal selected from the group consisting of tin, bismuth, lead, cadmium, magnesium, manganese, nickel, aluminum, cobalt, titanium, antimony, selenium, iron, rhenium, cerium, zinc, and zirconium.
92. The oxidation catalyst of claim 89 wherein the promoter comprises tin.
93. The oxidation catalyst of claim 89 wherein the promoter comprises iron.
150
94. The oxidation catalyst of claim 89 wherein the promoter comprises titanium.
95. The oxidation catalyst of claim 89 wherein at least two promoters are at the surface of the non-graphitic carbon support .
96. The oxidation catalyst of claim 95 wherein the promoters comprise iron and tin.
97. The oxidation catalyst of claim 89 wherein noble metal atoms at the surface are alloyed with the promoter,
98. The oxidation catalyst of claim 89 wherein a majority of the noble metal atoms at the surface are alloyed with the promoter.
99. The oxidation catalyst of claim 89 wherein substantially all of the noble metal atoms at the surface are alloyed with the promoter.
100. The oxidation catalyst of claim 88 wherein said temperature is at least about 500σC.
101. The oxidation catalyst of claim 88 wherein said temperature is from about 550 to about 1,200°C.
102. The oxidation catalyst of claim 88 wherein said temperature is from about 550 to about 900°C.
103. The oxidation catalyst of claim 88 wherein the heating is conducted in a non-oxidizing environment.
151
120. The oxidation catalyst of claim 112 wherein noble metal atoms at the surface are alloyed with the promoter.
121. The oxidation catalyst of claim 112 wherein a majority of the noble metal atoms at the surface are alloyed with the promoter.
122. The oxidation catalyst of claim 112 wherein substantially all of the noble metal atoms at the surface are alloyed with the promoter.
123. The oxidation catalyst of claim 111 wherein the reducing environment comprises ammonia.
124. The oxidation catalyst of claim 111 wherein the reducing environment comprises NaBH4.
125. A process for the preparation of an oxidation catalyst, the process comprising depositing a noble metal at a surface of a non-graphitic carbon support, and then heating the surface at a temperature greater than about 500°C.
126. The process of claim 125 wherein said temperature is from about 550 to about 1,200°C.
127. The process of claim 125 wherein said temperature is from about 550 to about 900βC,
128. The process of claim 125 wherein said heating is conducted in a non-oxidizing environment.
152
129. The process of claim 128 wherein said temperature is from about 550 to about 1 200°C.
130. The process of claim 128 wherein the non-oxidizing environment consists essentially of at least one gas selected from the group consisting of N2 and the noble gases.
131. The process of claim 128 wherein the non-oxidizing environment comprises a reducing environment .
132. The process of claim 131 wherein said temperature is from about 550 to about 1,200°C.
133. The process of claim 131 wherein the reducing environment comprises H2.
134. The process of claim 125 further comprising exposing the surface of the non-graphitic carbon support to ammonia .
135. The process of claim 125 further comprising contacting the surface of the non-graphitic carbon support with a solution comprising ammonium ions .
136. The process of claim 135 wherein the surface of the non-graphitic carbon support is contacted with a solution comprising ammonium ions after the noble metal is deposited at the surface.
137. The process of claim 125 further comprising contacting the surface of the non-graphitic carbon support with NaBH4.
153
138. The process of claim 125 further comprising removing oxygen from the surface of the non-graphitic carbon support before the noble metal is deposited at the surface.
139. The process of claim 125 wherein the noble metal is deposited at the surface of the non-graphitic carbon support using a noble metal precursor which comprises the noble metal in an oxidation state which is less than the maximum oxidation state of the noble metal .
140. The process of claim 125 wherein at least 0.05% by weight of the catalyst consists of at least one promoter.
141. The process of claim 140 wherein the promoter is more easily oxidized than the noble metal.
142. The process of claim 140 wherein the promoter comprises a metal selected from the group consisting of tin, bismuth, lead, cadmium, magnesium, manganese, nickel, aluminum, cobalt, titanium, antimony, selenium, iron, rhenium, cerium, zinc, and zirconium.
143. The process of claim 140 wherein the promoter comprises tin.
144. The process of claim 140 wherein the promoter comprises iron.
145. The process of claim 140 wherein the promoter comprises titanium.
146. The process of claim 140 wherein at least two promoters are deposited at the surface of the non-graphitic carbon support .
147. The process of claim 146 wherein the promoters comprise iron and tin.
148. The process of claim 140 wherein noble metal atoms at the surface are alloyed with the promoter.
149. The process of claim 140 wherein a majority of the noble metal atoms at the surface are alloyed with the promoter.
150. The process of claim 140 wherein substantially all of the noble metal atoms at the surface are alloyed with the promoter.
151. A process for the preparation of an oxidation catalyst from a non-graphitic carbon support having carbon and oxygen at a surface of the non-graphitic carbon support, the process comprising depositing a noble metal at the surface, and then heating the surface at a temperature of at least about 400°C, wherein the ratio of carbon atoms to oxygen atoms at the surface of the non-graphitic carbon support being at least about 20:1 as measured by x-ray photoelectron spectroscopy before the noble metal deposition.
152. The process of claim 151 wherein at least 0.05% by weight of the catalyst consists of at least one promoter.
153. The process of claim 152 wherein the promoter is more easily oxidized than the noble metal.
155
154. The process of claim 152 wherein the promoter comprises a metal selected from the group consisting of tin, bismuth, lead, cadmium, magnesium, manganese, nickel, aluminum, cobalt, titanium, antimony, selenium, iron, rhenium, cerium, zinc, and zirconium.
155. The process of claim 152 wherein the promoter comprises tin.
156. The process of claim 152 wherein the promoter comprises iron.
157. The process of claim 152 wherein the promoter comprises titanium.
158. The process of claim 152 wherein at least two promoters are deposited at the surface of the non-graphitic carbon support .
159. The process of claim 158 wherein the promoters comprise iron and tin.
160. The process of claim 152 wherein noble metal atoms at the surface are alloyed with the promoter.
161. The process of claim 152 wherein a majority of the noble metal atoms at the surface are alloyed with the promoter.
162. The process of claim 152 wherein substantially all of the noble metals at the surface are alloyed with the promoter.
156
PCT/US1999/003402 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions WO1999043430A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
AU27707/99A AU761345B2 (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
EA200000869A EA200000869A1 (en) 1998-02-25 1999-02-17 DEEPLY RESTORED OXIDATION CATALYST AND ITS APPLICATION FOR CATALYTIC LIQUID-PHASE OXIDATION REACTIONS
IL13808199A IL138081A0 (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
SK1256-2000A SK12562000A3 (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
KR1020007009463A KR20010041349A (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
JP2000533219A JP2002504427A (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use to catalyze liquid phase oxidation reactions
HU0101891A HUP0101891A3 (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
CA002321923A CA2321923C (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
BRPI9908252-7A BRPI9908252B1 (en) 1998-02-25 1999-02-17 process for the preparation of n- (phosphonomethyl) glycine or an n- (phosphonomethyl) glycine salt
EP99908217A EP1060017A1 (en) 1998-02-25 1999-02-17 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US7598898P 1998-02-25 1998-02-25
US60/075,988 1998-02-25
US09/248,655 1999-02-11
US09/248,655 US6417133B1 (en) 1998-02-25 1999-02-11 Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions

Publications (4)

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WO1999043430A1 WO1999043430A1 (en) 1999-09-02
WO1999043430B1 true WO1999043430B1 (en) 1999-11-04
WO1999043430A8 WO1999043430A8 (en) 1999-12-02
WO1999043430A9 WO1999043430A9 (en) 2000-01-27

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EP (1) EP1060017A1 (en)
JP (1) JP2002504427A (en)
KR (1) KR20010041349A (en)
CN (2) CN1962673B (en)
AR (3) AR013023A1 (en)
AU (1) AU761345B2 (en)
BR (2) BR9917783B1 (en)
CA (2) CA2610653C (en)
CZ (1) CZ20003020A3 (en)
EA (1) EA200000869A1 (en)
HU (1) HUP0101891A3 (en)
ID (1) ID26942A (en)
IL (1) IL138081A0 (en)
MX (2) MX270262B (en)
PL (1) PL342499A1 (en)
SK (1) SK12562000A3 (en)
TR (1) TR200002459T2 (en)
WO (1) WO1999043430A1 (en)
ZA (1) ZA991496B (en)

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