BRPI0721051B1 - complexos catalíticos à base de rutênio e reciláveis, assim como seu processo de síntese - Google Patents
complexos catalíticos à base de rutênio e reciláveis, assim como seu processo de síntese Download PDFInfo
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- BRPI0721051B1 BRPI0721051B1 BRPI0721051A BRPI0721051A BRPI0721051B1 BR PI0721051 B1 BRPI0721051 B1 BR PI0721051B1 BR PI0721051 A BRPI0721051 A BR PI0721051A BR PI0721051 A BRPI0721051 A BR PI0721051A BR PI0721051 B1 BRPI0721051 B1 BR PI0721051B1
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- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 8
- 230000015572 biosynthetic process Effects 0.000 title description 29
- 238000003786 synthesis reaction Methods 0.000 title description 29
- 230000003197 catalytic effect Effects 0.000 title description 25
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title description 6
- 229910052707 ruthenium Inorganic materials 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000000460 chlorine Substances 0.000 claims description 31
- -1 tetrafluoroborate Chemical compound 0.000 claims description 29
- 239000011230 binding agent Substances 0.000 claims description 14
- 239000012041 precatalyst Substances 0.000 claims description 13
- NJNNQEXHOIGLJK-UHFFFAOYSA-N 3-ethenyl-4-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=C(N)C=C1C=C NJNNQEXHOIGLJK-UHFFFAOYSA-N 0.000 claims description 11
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 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 2
- 239000003550 marker Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 229910017048 AsF6 Inorganic materials 0.000 claims 1
- 241000238102 Scylla Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- 150000001408 amides Chemical class 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000012327 Ruthenium complex Substances 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 150000003303 ruthenium Chemical class 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 238000005649 metathesis reaction Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VRBHURBJIHILRI-UHFFFAOYSA-N 1H-inden-1-ylidene Chemical group C1=CC=C2[C]C=CC2=C1 VRBHURBJIHILRI-UHFFFAOYSA-N 0.000 description 3
- WPWWHXPRJFDTTJ-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzamide Chemical compound NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F WPWWHXPRJFDTTJ-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000010668 complexation reaction Methods 0.000 description 3
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical compound CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- IUYZPYVWJWHHFD-UHFFFAOYSA-N n-(3-ethenyl-4-propan-2-yloxyphenyl)-2,2,2-trifluoroacetamide Chemical compound CC(C)OC1=CC=C(NC(=O)C(F)(F)F)C=C1C=C IUYZPYVWJWHHFD-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- LSMWOQFDLBIYPM-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-2h-imidazol-1-ium-2-ide Chemical compound CC1=CC(C)=CC(C)=C1N1[C-]=[N+](C=2C(=CC(C)=CC=2C)C)CC1 LSMWOQFDLBIYPM-UHFFFAOYSA-N 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 229910021135 KPF6 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 238000005865 alkene metathesis reaction Methods 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZZCRYUHDWGSHJW-UHFFFAOYSA-O n-(3-ethenyl-4-propan-2-yloxyphenyl)-4-pyridin-1-ium-1-ylbutanamide Chemical compound C1=C(C=C)C(OC(C)C)=CC=C1NC(=O)CCC[N+]1=CC=CC=C1 ZZCRYUHDWGSHJW-UHFFFAOYSA-O 0.000 description 2
- FSHNMTMNNCZFID-UHFFFAOYSA-N n-(3-ethenyl-4-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC=C(NC(C)=O)C=C1C=C FSHNMTMNNCZFID-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- VBJIFLOSOQGDRZ-UHFFFAOYSA-N (2-chloro-2,2-difluoroacetyl) 2-chloro-2,2-difluoroacetate Chemical compound FC(F)(Cl)C(=O)OC(=O)C(F)(F)Cl VBJIFLOSOQGDRZ-UHFFFAOYSA-N 0.000 description 1
- JNPGUXGVLNJQSQ-BGGMYYEUSA-M (e,3r,5s)-7-[4-(4-fluorophenyl)-1,2-di(propan-2-yl)pyrrol-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)N1C(C(C)C)=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C1 JNPGUXGVLNJQSQ-BGGMYYEUSA-M 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- SBPIDKODQVLBGV-UHFFFAOYSA-N 1h-imidazole;pyridine Chemical compound C1=CNC=N1.C1=CC=NC=C1 SBPIDKODQVLBGV-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical compound NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UTCWESKNHLBRDD-UHFFFAOYSA-N 3-chloro-2,2,3,3-tetrafluoropropanoyl chloride Chemical compound FC(F)(Cl)C(F)(F)C(Cl)=O UTCWESKNHLBRDD-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- LMWVVWHQIZVNIB-UHFFFAOYSA-N CC(C)OC1=C(C=C(C=C1)NC(=O)C(=O)N)C=C Chemical compound CC(C)OC1=C(C=C(C=C1)NC(=O)C(=O)N)C=C LMWVVWHQIZVNIB-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 101100537098 Mus musculus Alyref gene Proteins 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 101150095908 apex1 gene Proteins 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940000489 arsenate Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010814 metallic waste Substances 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GHCYKINLFBHAHJ-UHFFFAOYSA-N n,n'-bis(3-ethenyl-4-propan-2-yloxyphenyl)oxamide Chemical compound C1=C(C=C)C(OC(C)C)=CC=C1NC(=O)C(=O)NC1=CC=C(OC(C)C)C(C=C)=C1 GHCYKINLFBHAHJ-UHFFFAOYSA-N 0.000 description 1
- YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 1
- PZUGJLOCXUNFLM-UHFFFAOYSA-N n-ethenylaniline Chemical compound C=CNC1=CC=CC=C1 PZUGJLOCXUNFLM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- MYHOHFDYWMPGJY-UHFFFAOYSA-N pentafluorobenzoyl chloride Chemical compound FC1=C(F)C(F)=C(C(Cl)=O)C(F)=C1F MYHOHFDYWMPGJY-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- 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
- 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
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0610478A FR2909381A1 (fr) | 2006-11-30 | 2006-11-30 | Complexes de rethenium et utilisation de tels complexes pour la metathese d'olefines |
| FR0610478 | 2006-11-30 | ||
| FR0700634A FR2909382B1 (fr) | 2006-11-30 | 2007-01-30 | Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines |
| FR0700634 | 2007-01-30 | ||
| PCT/EP2007/063062 WO2008065187A1 (fr) | 2006-11-30 | 2007-11-30 | Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0721051A2 BRPI0721051A2 (pt) | 2014-07-29 |
| BRPI0721051B1 true BRPI0721051B1 (pt) | 2017-05-09 |
Family
ID=39186057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0721051A BRPI0721051B1 (pt) | 2006-11-30 | 2007-11-30 | complexos catalíticos à base de rutênio e reciláveis, assim como seu processo de síntese |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8394965B2 (enExample) |
| EP (2) | EP2476688B1 (enExample) |
| JP (1) | JP5284269B2 (enExample) |
| CN (1) | CN103601758B (enExample) |
| BR (1) | BRPI0721051B1 (enExample) |
| CA (1) | CA2671082A1 (enExample) |
| FR (1) | FR2909382B1 (enExample) |
| IN (1) | IN2009KN02409A (enExample) |
| WO (1) | WO2008065187A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5602161B2 (ja) | 2009-02-03 | 2014-10-08 | イデニク プハルマセウティカルス，インコーポレイテッド | ホスフィナートルテニウム錯体 |
| EP2255877B1 (en) | 2009-05-07 | 2014-09-24 | Umicore AG & Co. KG | Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands |
| BR112013002329A2 (pt) | 2010-07-30 | 2016-05-24 | Centre Nat Rech Scient | catalisadores de metátese estáveis e altamente ajustáveis |
| IN2014CN00746A (enExample) | 2011-07-12 | 2015-04-03 | Basf Se | |
| US8993819B2 (en) | 2011-07-12 | 2015-03-31 | Basf Se | Process for preparing cycloheptene |
| WO2013010676A2 (en) | 2011-07-20 | 2013-01-24 | Ecole Nationale Superieure De Chimie De Rennes | Supported ionic liquid phase catalyst |
| PL230302B1 (pl) | 2012-02-27 | 2018-10-31 | Apeiron Synthesis Spolka Z Ograniczona Odpowiedzialnoscia | Katalizatory metatezy zawierające grupy oniowe |
| GB201204715D0 (en) | 2012-03-18 | 2012-05-02 | Croda Int Plc | Metathesis of olefins using ruthenium-based catalytic complexes |
| MX356142B (es) | 2012-06-13 | 2018-05-16 | Basf Se | Metodo para producir cetonas macrociclicas. |
| JP6092379B2 (ja) | 2012-06-29 | 2017-03-08 | アペイロン シンセシス エス アー | 金属錯体、その適用、及びメタセシス反応の実施方法 |
| FR2992642B1 (fr) * | 2012-06-29 | 2015-06-19 | Novance | Procede de synthese d’acides insatures biosources |
| FR2999184B1 (fr) * | 2012-12-12 | 2015-01-09 | Ecole Nationale Superieure De Chimie De Rennes | Complexes de ruthenium comprenant un diaminocarbene n-heterocyclique insature dissymetrique |
| FR3003564B1 (fr) * | 2013-03-19 | 2015-03-06 | Arkema France | Procede de metathese comprenant l'extraction de l'ethylene forme au moyen d'une membrane |
| PL3008078T3 (pl) | 2013-06-12 | 2019-06-28 | Trustees Of Boston College | Katalizatory do wydajnej, Z-selektywnej metatezy |
| GB201322936D0 (en) | 2013-12-23 | 2014-02-12 | Croda Int Plc | Polyurethane |
| GB201322933D0 (en) | 2013-12-23 | 2014-02-12 | Croda Int Plc | A polyol |
| MX2018006241A (es) | 2015-11-18 | 2018-11-09 | Provivi Inc | Produccion de derivados de olefina grasa via metatesis de olefina. |
| EP3376859B1 (en) | 2015-11-18 | 2021-01-06 | Provivi, Inc. | Microorganisms for the production of insect pheromones and related compounds |
| PL3386936T3 (pl) * | 2015-12-10 | 2024-10-07 | Umicore Ag & Co. Kg | Katalizatory metatezy olefin |
| AR110606A1 (es) | 2016-06-06 | 2019-04-17 | Provivi Inc | Producción semi-biosintética de alcoholes grasos y aldehídos grasos |
| PL3538508T3 (pl) | 2016-11-09 | 2021-10-25 | Verbio Vereinigte Bioenergie Ag | Kompleksy rutenu przydatne do katalizowania reakcji metatezy |
| WO2018150379A2 (en) | 2017-02-17 | 2018-08-23 | Provivi, Inc. | Synthesis of pheromones and related materials via olefin metathesis |
| FR3063290A1 (fr) | 2017-02-24 | 2018-08-31 | Stratoz | Procede de synthese de pheromones |
| EP3635124A4 (en) | 2017-05-17 | 2021-03-31 | Provivi, Inc. | MICRO-ORGANISMS INTENDED FOR THE PRODUCTION OF INSECT PHEROMONES AND ASSOCIATED COMPOUNDS |
| CN107641165B (zh) * | 2017-08-08 | 2020-05-08 | 上海克琴科技有限公司 | 钌金属催化剂DREAM-2nd及其在烯烃关环复分解和双环戊二烯聚合反应中的应用 |
| WO2019110658A1 (de) | 2017-12-08 | 2019-06-13 | Arlanxeo Deutschland Gmbh | Verfahren zur herstellung von nitrilkautschuken mit ruthenium-komplexkatalysatoren |
| US11891517B2 (en) | 2020-03-10 | 2024-02-06 | Exxonmobil Chemical Patents Inc. | Wax compositions comprising linear olefin dimers or hydrogenated variants thereof and methods for production thereof |
| GB202104081D0 (en) | 2021-03-24 | 2021-05-05 | Croda Int Plc | Coatings, adhesives and elastomers utilising acetoacetate end-capped polyol |
| GB202104089D0 (en) | 2021-03-24 | 2021-05-05 | Croda Int Plc | Elastomeric polymer compositions and rail track structures and systems comprimising the same |
| GB202104083D0 (en) | 2021-03-24 | 2021-05-05 | Croda Int Plc | Coatings, adhesives and elastomers utilising acetoacetate end-capped polyol derived from thermoplastic polyesters |
| US11596612B1 (en) | 2022-03-08 | 2023-03-07 | PTC Innovations, LLC | Topical anesthetics |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287201A (en) * | 1980-03-03 | 1981-09-01 | Merck & Co., Inc. | Anovulatory method and chicken feed compositions |
| JP2632248B2 (ja) * | 1992-09-01 | 1997-07-23 | ファイザー・インク． | 抗菌活性を有する４−ヒドロキシクマリン誘導体 |
| DE60140455D1 (de) | 2000-08-10 | 2009-12-24 | Trustees Boston College | Wiederverwendbare methathese-katalysatoren |
| EP1455937B1 (en) * | 2001-11-15 | 2018-04-11 | Materia, Inc. | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
| PL199412B1 (pl) * | 2002-10-15 | 2008-09-30 | Boehringer Ingelheim Int | Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania |
| DE10335417A1 (de) * | 2003-08-02 | 2005-02-17 | Arlt, Dieter, Prof. Dr. | Verfahren zur Herstellung von Metathesekatalysatoren |
| JP5406525B2 (ja) * | 2005-07-04 | 2014-02-05 | ツァナン・サイテック・カンパニー・リミテッド | ルテニウム錯体配位子、ルテニウム錯体、固定化ルテニウム錯体触媒及びその調製方法と用途 |
-
2007
- 2007-01-30 FR FR0700634A patent/FR2909382B1/fr not_active Expired - Fee Related
- 2007-11-30 US US12/517,322 patent/US8394965B2/en active Active
- 2007-11-30 WO PCT/EP2007/063062 patent/WO2008065187A1/fr not_active Ceased
- 2007-11-30 IN IN2409KON2009 patent/IN2009KN02409A/en unknown
- 2007-11-30 EP EP11192598.8A patent/EP2476688B1/fr active Active
- 2007-11-30 EP EP07847578.7A patent/EP2097431B1/fr active Active
- 2007-11-30 JP JP2009538722A patent/JP5284269B2/ja not_active Expired - Fee Related
- 2007-11-30 CN CN201310436838.0A patent/CN103601758B/zh not_active Expired - Fee Related
- 2007-11-30 BR BRPI0721051A patent/BRPI0721051B1/pt not_active IP Right Cessation
- 2007-11-30 CA CA002671082A patent/CA2671082A1/fr not_active Abandoned
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2013
- 2013-02-13 US US13/736,236 patent/US8586757B2/en active Active
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| Publication number | Publication date |
|---|---|
| US20100087644A1 (en) | 2010-04-08 |
| US8394965B2 (en) | 2013-03-12 |
| WO2008065187A1 (fr) | 2008-06-05 |
| IN2009KN02409A (enExample) | 2015-08-07 |
| FR2909382B1 (fr) | 2009-01-23 |
| EP2097431B1 (fr) | 2015-03-25 |
| BRPI0721051A2 (pt) | 2014-07-29 |
| FR2909382A1 (fr) | 2008-06-06 |
| US8586757B2 (en) | 2013-11-19 |
| CN103601758B (zh) | 2017-09-08 |
| JP5284269B2 (ja) | 2013-09-11 |
| CA2671082A1 (fr) | 2008-06-05 |
| EP2476688B1 (fr) | 2017-06-14 |
| CN103601758A (zh) | 2014-02-26 |
| JP2010511017A (ja) | 2010-04-08 |
| EP2476688A1 (fr) | 2012-07-18 |
| US20130144060A1 (en) | 2013-06-06 |
| EP2097431A1 (fr) | 2009-09-09 |
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