AP919A - Metal chelate complexes for foming oxidation catalyst. - Google Patents
Metal chelate complexes for foming oxidation catalyst. Download PDFInfo
- Publication number
- AP919A AP919A APAP/P/1999/001455A AP9901455A AP919A AP 919 A AP919 A AP 919A AP 9901455 A AP9901455 A AP 9901455A AP 919 A AP919 A AP 919A
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- ARIPO
- Prior art keywords
- group
- complex
- metal
- amino
- recited
- Prior art date
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- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 66
- 230000003647 oxidation Effects 0.000 title claims abstract description 62
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 55
- 239000002184 metal Substances 0.000 title claims abstract description 53
- 239000013522 chelant Substances 0.000 title claims abstract description 31
- 239000003054 catalyst Substances 0.000 title abstract description 27
- 239000003446 ligand Substances 0.000 claims abstract description 83
- 125000001424 substituent group Chemical group 0.000 claims abstract description 40
- 125000004429 atom Chemical group 0.000 claims abstract description 26
- 150000002367 halogens Chemical class 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 15
- 150000003624 transition metals Chemical class 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 150000004697 chelate complex Chemical class 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- -1 amino, substituted amino Chemical group 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 230000001590 oxidative effect Effects 0.000 claims description 32
- 238000010525 oxidative degradation reaction Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 238000005304 joining Methods 0.000 claims description 9
- 239000000470 constituent Substances 0.000 claims description 7
- 150000004696 coordination complex Chemical class 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 150000002978 peroxides Chemical class 0.000 claims description 6
- 230000000536 complexating effect Effects 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 229910052713 technetium Inorganic materials 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 abstract description 3
- 239000012190 activator Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 47
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- 125000005647 linker group Chemical group 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 239000007800 oxidant agent Substances 0.000 description 30
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 150000004985 diamines Chemical class 0.000 description 21
- 125000004043 oxo group Chemical group O=* 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 19
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 150000002500 ions Chemical class 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
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- 238000006467 substitution reaction Methods 0.000 description 15
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- 229910021645 metal ion Inorganic materials 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
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- 239000002253 acid Substances 0.000 description 12
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 241000894007 species Species 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 150000001540 azides Chemical class 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 9
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 9
- 238000012512 characterization method Methods 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000010933 acylation Effects 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 8
- 230000015556 catabolic process Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 238000005710 macrocyclization reaction Methods 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000006555 catalytic reaction Methods 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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- 230000003197 catalytic effect Effects 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- 150000002466 imines Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- MLVIMJJNLIMRCJ-UHFFFAOYSA-N 2,4-diamino-2,4-dimethylpentan-3-one Chemical compound CC(C)(N)C(=O)C(C)(C)N MLVIMJJNLIMRCJ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
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- 150000002690 malonic acid derivatives Chemical class 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
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- 238000006798 ring closing metathesis reaction Methods 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 5
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- CJXQAYQWVNXIQE-UHFFFAOYSA-N 2,2-dimethylpropanedioyl dichloride Chemical compound ClC(=O)C(C)(C)C(Cl)=O CJXQAYQWVNXIQE-UHFFFAOYSA-N 0.000 description 4
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 4
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
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- ZJKGRSJMFDIRPX-UHFFFAOYSA-N 5-methyl-3-nitropyridin-2-amine Chemical compound CC1=CN=C(N)C([N+]([O-])=O)=C1 ZJKGRSJMFDIRPX-UHFFFAOYSA-N 0.000 description 3
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- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
- C07F15/0026—Osmium compounds without a metal-carbon linkage
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- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
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- B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
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- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/10—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/825—Osmium
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/828—Platinum
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
-
- 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
-
- 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
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/681,237 US5847120A (en) | 1996-07-22 | 1996-07-22 | Long-lived homogenous oxidation catalysts |
| PCT/US1997/012803 WO1998003263A1 (en) | 1996-07-22 | 1997-07-21 | Long-lived homogenous oxidation catalysts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9901455A0 AP9901455A0 (en) | 1999-03-31 |
| AP919A true AP919A (en) | 2000-12-29 |
Family
ID=24734398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1999/001455A AP919A (en) | 1996-07-22 | 1997-07-21 | Metal chelate complexes for foming oxidation catalyst. |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US5847120A (de) |
| EP (1) | EP0914206B1 (de) |
| JP (2) | JP2000515152A (de) |
| KR (1) | KR100491450B1 (de) |
| CN (1) | CN1121906C (de) |
| AP (1) | AP919A (de) |
| AT (1) | ATE229372T1 (de) |
| AU (1) | AU729102B2 (de) |
| BR (1) | BR9710513B1 (de) |
| CA (1) | CA2261589C (de) |
| DE (1) | DE69717819T2 (de) |
| DK (1) | DK0914206T3 (de) |
| ES (1) | ES2188969T3 (de) |
| IL (1) | IL128150A0 (de) |
| NO (1) | NO326043B1 (de) |
| NZ (1) | NZ333797A (de) |
| OA (1) | OA10960A (de) |
| PL (1) | PL187534B1 (de) |
| PT (1) | PT914206E (de) |
| WO (1) | WO1998003263A1 (de) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6054580A (en) * | 1996-07-22 | 2000-04-25 | Carnegie Mellon University | Long-lived homogenous amide containing macrocyclic compounds |
| US5847120A (en) * | 1996-07-22 | 1998-12-08 | Carnegie Mellon University | Long-lived homogenous oxidation catalysts |
| US5876625A (en) * | 1996-07-22 | 1999-03-02 | Carnegie Mellon University | Metal ligand containing bleaching compositions |
| WO1998058735A1 (en) * | 1997-06-20 | 1998-12-30 | Carnegie Mellon University | Homogeneous oxidation catalysis using metal complexes |
| WO1999052631A1 (en) * | 1998-04-15 | 1999-10-21 | Shell Internationale Research Maatschappij B.V. | CATALYST SYSTEM FOR α-OLEFIN OLIGOMERIZATION |
| US6861262B2 (en) | 2000-03-03 | 2005-03-01 | Quest Diagnostics Investments Incorporated | Composition and method for detecting an adulterant in an aqueous sample |
| GB0020846D0 (en) * | 2000-08-23 | 2000-10-11 | Unilever Plc | Ligands for bleaching compositions and synthesis thereof |
| US6797196B2 (en) | 2001-01-10 | 2004-09-28 | Kao Corporation | Bleaching formulation |
| GB0118936D0 (en) * | 2001-08-02 | 2001-09-26 | Unilever Plc | Improvements relating to colour-safe fabric treatment compositions |
| BR0211875A (pt) * | 2001-08-02 | 2004-09-21 | Unilever Nv | Composições compreendendo complexo de metal de tetraamido macrocìclico como catalisador de alvejamento |
| GB0205276D0 (en) * | 2002-03-06 | 2002-04-17 | Unilever Plc | Bleaching composition |
| GB0205278D0 (en) * | 2002-03-06 | 2002-04-17 | Unilever Plc | Composition comprising macrocyclic tetra-amido N-donor metal-ligand complex as bleaching catalyst |
| DE10227774A1 (de) * | 2002-06-21 | 2004-01-08 | Degussa Ag | Verwendung von Übergangsmetallkomplexen mit stickstoffhaltigen mehrzähnigen Liganden als Bleichkatalysator und Bleichmittelzusammensetzung |
| US7060818B2 (en) * | 2003-02-21 | 2006-06-13 | Carnegie Mellon University | Synthesis of macrocyclic tetraamido compounds and new metal insertion process |
| US7989647B2 (en) | 2005-03-03 | 2011-08-02 | South Dakota Soybean Processors, Llc | Polyols derived from a vegetable oil using an oxidation process |
| CN100412080C (zh) * | 2005-04-06 | 2008-08-20 | 友达光电股份有限公司 | 有机金属络合物及包括它的有机发光二极管和显示器 |
| WO2008018856A2 (en) * | 2005-06-21 | 2008-02-14 | Crosslink Polymer Research | Signal activated decontaminating coating |
| EP1933941A2 (de) | 2005-08-25 | 2008-06-25 | Philip R. Houle | Behandlungssysteme zur abgabe von sensibilisatorlösungen |
| US7744749B2 (en) * | 2005-09-08 | 2010-06-29 | Saudi Arabian Oil Company | Diesel oil desulfurization by oxidation and extraction |
| US8715489B2 (en) * | 2005-09-08 | 2014-05-06 | Saudi Arabian Oil Company | Process for oxidative conversion of organosulfur compounds in liquid hydrocarbon mixtures |
| US20090288946A1 (en) * | 2008-05-23 | 2009-11-26 | Lumimove, Inc. Dba Crosslink | Electroactivated film with layered structure |
| US8722881B2 (en) * | 2009-10-13 | 2014-05-13 | Board Of Trustees Of The University Of Arkansas | Method of synthesis of tetradentate amide macrocycle ligand and its metal-complex |
| US8584757B2 (en) | 2010-04-21 | 2013-11-19 | Halliburton Energy Services, Inc. | Method and composition for treating fluids before injection into subterranean zones |
| US20150342839A1 (en) | 2010-04-21 | 2015-12-03 | Oraceutica LLC | Compositions and methods for whitening teeth |
| RU2012149460A (ru) | 2010-04-21 | 2014-05-27 | ДИСКУС ДЕНТАЛ, ЭлЭлСи | Способ одновременной чистки и отбеливания зубов |
| US8888489B2 (en) | 2012-10-23 | 2014-11-18 | Oraceutical Llc | Method of simultaneously cleaning and whitening teeth |
| US9320580B2 (en) | 2013-04-21 | 2016-04-26 | Oraceutical Llc | Hand-held tooth whitening instrument with applicator reservoir for whitening composition and methods of using same |
| US10048269B2 (en) | 2014-07-25 | 2018-08-14 | SeLux Diagnostics, Inc. | Assay methods involving dissociable nanoparticles |
| WO2016171572A1 (en) * | 2015-04-24 | 2016-10-27 | Auckland Uniservices Limited | Oxidation method |
| AR104940A1 (es) | 2015-06-10 | 2017-08-23 | Chemsenti Ltd | Método para generar dióxido de cloro |
| AR104939A1 (es) | 2015-06-10 | 2017-08-23 | Chemsenti Ltd | Método oxidativo para generar dióxido de cloro |
| WO2017015145A2 (en) | 2015-07-17 | 2017-01-26 | SeLux Diagnostics, Inc. | Dissociable transition-metal nanoparticles |
| CA3036495A1 (en) | 2015-09-25 | 2017-03-30 | Carnegie Mellon University | Oxidation catalysts based on macrocyclic compounds |
| WO2017100442A1 (en) | 2015-12-08 | 2017-06-15 | SeLux Diagnostics, Inc. | Nanoparticle amplifiers and uses thereof |
| EP3845663A1 (de) | 2016-01-21 | 2021-07-07 | Selux Diagnostics Inc. | Verfahren für schnelltest auf antimikrobielle suszeptibilität |
| RU2653989C2 (ru) * | 2016-04-26 | 2018-05-16 | Федеральное Государственное Бюджетное Научное Учреждение Уфимский Федеральный Исследовательский Центр Российской Академии Наук (Уфиц Ран) | Катализатор для получения 3-(3-фенилпроп-2-ин-1-ил)-1,3-оксазолидина |
| WO2018119439A1 (en) | 2016-12-23 | 2018-06-28 | SeLux Diagnostics, Inc. | Methods for improved rapid antimicrobial susceptibility testing |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4577042A (en) * | 1983-03-17 | 1986-03-18 | California Institute Of Technology | Homogeneous coordination compounds as oxidation catalysts |
| US4758682A (en) * | 1983-03-17 | 1988-07-19 | California Institute Of Technology | Homogeneous coordination compounds as oxidation catalysts |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4952289A (en) * | 1988-05-09 | 1990-08-28 | Aquanautics Corporation | Macrocyclic amine complexes for ligand extraction and generation |
| US4987227A (en) * | 1988-10-21 | 1991-01-22 | The Research Foundation Of State University Of New York | Polyazamacrocycles and their metal complexes |
| US5021595A (en) * | 1990-03-02 | 1991-06-04 | Exxon Chemical Patents Inc. | Transition metal catalyst composition for olefin polymerization |
| US5847120A (en) * | 1996-07-22 | 1998-12-08 | Carnegie Mellon University | Long-lived homogenous oxidation catalysts |
-
1996
- 1996-07-22 US US08/681,237 patent/US5847120A/en not_active Expired - Lifetime
-
1997
- 1997-07-21 DE DE69717819T patent/DE69717819T2/de not_active Expired - Lifetime
- 1997-07-21 EP EP97938014A patent/EP0914206B1/de not_active Expired - Lifetime
- 1997-07-21 PL PL97331315A patent/PL187534B1/pl not_active IP Right Cessation
- 1997-07-21 JP JP10507184A patent/JP2000515152A/ja not_active Withdrawn
- 1997-07-21 WO PCT/US1997/012803 patent/WO1998003263A1/en not_active Ceased
- 1997-07-21 IL IL12815097A patent/IL128150A0/xx unknown
- 1997-07-21 CA CA002261589A patent/CA2261589C/en not_active Expired - Lifetime
- 1997-07-21 DK DK97938014T patent/DK0914206T3/da active
- 1997-07-21 CN CN97198097A patent/CN1121906C/zh not_active Expired - Lifetime
- 1997-07-21 BR BRPI9710513-9A patent/BR9710513B1/pt not_active IP Right Cessation
- 1997-07-21 AP APAP/P/1999/001455A patent/AP919A/en active
- 1997-07-21 AU AU40436/97A patent/AU729102B2/en not_active Expired
- 1997-07-21 ES ES97938014T patent/ES2188969T3/es not_active Expired - Lifetime
- 1997-07-21 KR KR10-1999-7000527A patent/KR100491450B1/ko not_active Expired - Fee Related
- 1997-07-21 PT PT97938014T patent/PT914206E/pt unknown
- 1997-07-21 AT AT97938014T patent/ATE229372T1/de not_active IP Right Cessation
- 1997-07-21 NZ NZ333797A patent/NZ333797A/en not_active IP Right Cessation
-
1998
- 1998-05-12 US US09/076,410 patent/US6100394A/en not_active Expired - Lifetime
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1999
- 1999-01-20 OA OA9900011A patent/OA10960A/en unknown
- 1999-01-21 NO NO19990268A patent/NO326043B1/no not_active IP Right Cessation
-
2006
- 2006-08-02 JP JP2006210959A patent/JP2007016036A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4577042A (en) * | 1983-03-17 | 1986-03-18 | California Institute Of Technology | Homogeneous coordination compounds as oxidation catalysts |
| US4758682A (en) * | 1983-03-17 | 1988-07-19 | California Institute Of Technology | Homogeneous coordination compounds as oxidation catalysts |
Also Published As
| Publication number | Publication date |
|---|---|
| US5847120A (en) | 1998-12-08 |
| DK0914206T3 (da) | 2003-04-07 |
| NO326043B1 (no) | 2008-09-08 |
| DE69717819T2 (de) | 2003-07-10 |
| HK1020176A1 (en) | 2000-03-31 |
| ATE229372T1 (de) | 2002-12-15 |
| EP0914206A1 (de) | 1999-05-12 |
| JP2000515152A (ja) | 2000-11-14 |
| CA2261589A1 (en) | 1998-01-29 |
| DE69717819D1 (de) | 2003-01-23 |
| IL128150A0 (en) | 1999-11-30 |
| US6100394A (en) | 2000-08-08 |
| NO990268L (no) | 1999-03-22 |
| ES2188969T3 (es) | 2003-07-01 |
| EP0914206B1 (de) | 2002-12-11 |
| AU4043697A (en) | 1998-02-10 |
| KR100491450B1 (ko) | 2005-05-25 |
| PL331315A1 (en) | 1999-07-05 |
| NZ333797A (en) | 2000-06-23 |
| CN1230903A (zh) | 1999-10-06 |
| OA10960A (en) | 2001-10-29 |
| CA2261589C (en) | 2002-10-01 |
| WO1998003263A1 (en) | 1998-01-29 |
| AP9901455A0 (en) | 1999-03-31 |
| AU729102B2 (en) | 2001-01-25 |
| KR20000067993A (ko) | 2000-11-25 |
| PT914206E (pt) | 2003-04-30 |
| CN1121906C (zh) | 2003-09-24 |
| BR9710513B1 (pt) | 2010-10-19 |
| BR9710513A (pt) | 2002-03-05 |
| JP2007016036A (ja) | 2007-01-25 |
| NO990268D0 (no) | 1999-01-21 |
| PL187534B1 (pl) | 2004-07-30 |
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