CA2671082A1 - Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines - Google Patents
Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines Download PDFInfo
- Publication number
- CA2671082A1 CA2671082A1 CA002671082A CA2671082A CA2671082A1 CA 2671082 A1 CA2671082 A1 CA 2671082A1 CA 002671082 A CA002671082 A CA 002671082A CA 2671082 A CA2671082 A CA 2671082A CA 2671082 A1 CA2671082 A1 CA 2671082A1
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- CA
- Canada
- Prior art keywords
- formula
- compound according
- meets
- compound
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 230000003197 catalytic effect Effects 0.000 title description 22
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title description 8
- 229910052707 ruthenium Inorganic materials 0.000 title description 8
- 238000005865 alkene metathesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000003446 ligand Substances 0.000 claims abstract description 28
- -1 C1-C6 perhaloalkyl Chemical class 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 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 abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 239000003550 marker Substances 0.000 claims abstract description 5
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 3
- 125000000129 anionic group Chemical group 0.000 claims abstract description 3
- 150000001450 anions Chemical group 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 150000002576 ketones Chemical class 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 27
- 238000003786 synthesis reaction Methods 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 26
- 150000001408 amides Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 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
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 229910017048 AsF6 Inorganic materials 0.000 claims description 2
- 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
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 238000004587 chromatography analysis Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- 238000005649 metathesis reaction Methods 0.000 description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000012327 Ruthenium complex Substances 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- 239000000243 solution Substances 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
- 230000000694 effects Effects 0.000 description 8
- 150000003303 ruthenium Chemical class 0.000 description 8
- 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
- 238000004064 recycling Methods 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 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
- 239000012074 organic phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- 229910014211 My O Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 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
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- MFGJWGZXHCDWLT-UHFFFAOYSA-N n-(3-ethenyl-4-propan-2-yloxyphenyl)-2,3,4,5,6-pentafluorobenzamide Chemical compound C1=C(C=C)C(OC(C)C)=CC=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F MFGJWGZXHCDWLT-UHFFFAOYSA-N 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
- 230000009257 reactivity Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 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
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 1
- GPQXCSVEZHPWMA-UHFFFAOYSA-N 1-fluoro-2h-pyridine Chemical compound FN1CC=CC=C1 GPQXCSVEZHPWMA-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 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 1
- KVIFXWNDSNHROF-UHFFFAOYSA-N 2-chloro-n-(3-ethenyl-4-propan-2-yloxyphenyl)-2,2-difluoroacetamide Chemical compound CC(C)OC1=CC=C(NC(=O)C(F)(F)Cl)C=C1C=C KVIFXWNDSNHROF-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229910021135 KPF6 Inorganic materials 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 150000002739 metals Chemical class 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
- VDCVNGOVUXDMBE-UHFFFAOYSA-O n-(3-ethenyl-4-propan-2-yloxyphenyl)-2,2-difluoro-2-(3-methylimidazol-3-ium-1-yl)acetamide Chemical compound C1=C(C=C)C(OC(C)C)=CC=C1NC(=O)C(F)(F)[N+]1=CN(C)C=C1 VDCVNGOVUXDMBE-UHFFFAOYSA-O 0.000 description 1
- 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 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 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
- 239000012071 phase 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000002699 waste material Substances 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 |
|---|---|---|---|
| FR0610478 | 2006-11-30 | ||
| FR0610478A FR2909381A1 (fr) | 2006-11-30 | 2006-11-30 | Complexes de rethenium et utilisation de tels complexes pour la metathese d'olefines |
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2671082A1 true CA2671082A1 (fr) | 2008-06-05 |
Family
ID=39186057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002671082A Abandoned CA2671082A1 (fr) | 2006-11-30 | 2007-11-30 | Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8394965B2 (OSRAM) |
| EP (2) | EP2476688B1 (OSRAM) |
| JP (1) | JP5284269B2 (OSRAM) |
| CN (1) | CN103601758B (OSRAM) |
| BR (1) | BRPI0721051B1 (OSRAM) |
| CA (1) | CA2671082A1 (OSRAM) |
| FR (1) | FR2909382B1 (OSRAM) |
| IN (1) | IN2009KN02409A (OSRAM) |
| WO (1) | WO2008065187A1 (OSRAM) |
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 |
| CA2806754C (en) | 2010-07-30 | 2020-04-07 | Ecole Nationale Superieure De Chimie De Rennes | Ruthenium compounds as metathesis catalysts |
| US8993819B2 (en) | 2011-07-12 | 2015-03-31 | Basf Se | Process for preparing cycloheptene |
| JP5916855B2 (ja) | 2011-07-12 | 2016-05-11 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | シクロヘプテンの製造法 |
| 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 |
| CN104379547B (zh) | 2012-06-13 | 2017-05-17 | 巴斯夫欧洲公司 | 制备大环酮的方法 |
| CN104350060B (zh) | 2012-06-29 | 2017-09-12 | 阿派朗合成公司 | 金属络合物、其应用和进行复分解反应的方法 |
| 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 |
| EP3008078B1 (en) | 2013-06-12 | 2018-12-19 | Trustees of Boston College | Catalysts for efficient z-selective metathesis |
| GB201322933D0 (en) | 2013-12-23 | 2014-02-12 | Croda Int Plc | A polyol |
| GB201322936D0 (en) | 2013-12-23 | 2014-02-12 | Croda Int Plc | Polyurethane |
| HUE053613T2 (hu) | 2015-11-18 | 2021-07-28 | Provivi Inc | Mikroorganizmusok rovarferomonok és kapcsolódó vegyületek elõállítására |
| AU2016357756B2 (en) | 2015-11-18 | 2021-09-30 | Provivi, Inc. | Production of fatty olefin derivatives via olefin metathesis |
| WO2017100585A1 (en) * | 2015-12-10 | 2017-06-15 | Materia, Inc. | Olefin metathesis catalysts |
| JP2019517797A (ja) | 2016-06-06 | 2019-06-27 | プロヴィヴィ インコーポレイテッド | 脂肪アルコールおよび脂肪アルデヒドの半生合成的生産 |
| HUE069420T2 (hu) | 2016-11-09 | 2025-03-28 | Verbio Ver Bioenergie Ag | Metatézisreakciók katalizálására hasznosító ruténiumkomplexek |
| JP7153937B2 (ja) | 2017-02-17 | 2022-10-17 | プロビビ インコーポレイテッド | オレフィンメタセシスによるフェロモンおよび関連材料の合成方法 |
| FR3063290A1 (fr) | 2017-02-24 | 2018-08-31 | Stratoz | Procede de synthese de pheromones |
| US11104921B2 (en) | 2017-05-17 | 2021-08-31 | Provivi, Inc. | Microorganisms for the production of insect pheromones and related 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 |
| JP7248677B2 (ja) | 2017-12-08 | 2023-03-29 | アランセオ・ドイチュランド・ゲーエムベーハー | ルテニウム錯体触媒を使用してニトリルゴムを製造するためのプロセス |
| CN115427513A (zh) | 2020-03-10 | 2022-12-02 | 埃克森美孚化学专利公司 | 包含线性烯烃二聚体或者其氢化变体的蜡组合物及其生产方法 |
| GB202104083D0 (en) | 2021-03-24 | 2021-05-05 | Croda Int Plc | Coatings, adhesives and elastomers utilising acetoacetate end-capped polyol derived from thermoplastic polyesters |
| 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 |
| US11596612B1 (en) | 2022-03-08 | 2023-03-07 | PTC Innovations, LLC | Topical anesthetics |
Family Cites Families (7)
| 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 |
| EP0658158A1 (en) | 1992-09-01 | 1995-06-21 | Pfizer Inc. | 4-hydroxy coumarin derivatives with antibacterial activity |
| CA2419485C (en) | 2000-08-10 | 2007-10-30 | The Trustees Of Boston College | Recyclable metathesis catalysts |
| WO2003044060A2 (en) * | 2001-11-15 | 2003-05-30 | 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 |
| EP2886549A1 (en) * | 2005-07-04 | 2015-06-24 | Zannan Scitech Co., Ltd. | Ruthenium complex ligand, ruthenium complex and the use of the complex as a catalyst in olefin metathesis reactions |
-
2007
- 2007-01-30 FR FR0700634A patent/FR2909382B1/fr not_active Expired - Fee Related
- 2007-11-30 CA CA002671082A patent/CA2671082A1/fr not_active Abandoned
- 2007-11-30 IN IN2409KON2009 patent/IN2009KN02409A/en unknown
- 2007-11-30 US US12/517,322 patent/US8394965B2/en 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 EP EP11192598.8A patent/EP2476688B1/fr active Active
- 2007-11-30 EP EP07847578.7A patent/EP2097431B1/fr active Active
- 2007-11-30 WO PCT/EP2007/063062 patent/WO2008065187A1/fr not_active Ceased
- 2007-11-30 BR BRPI0721051A patent/BRPI0721051B1/pt not_active IP Right Cessation
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2013
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|---|---|
| US20100087644A1 (en) | 2010-04-08 |
| JP5284269B2 (ja) | 2013-09-11 |
| US8586757B2 (en) | 2013-11-19 |
| BRPI0721051A2 (pt) | 2014-07-29 |
| EP2476688A1 (fr) | 2012-07-18 |
| FR2909382B1 (fr) | 2009-01-23 |
| US20130144060A1 (en) | 2013-06-06 |
| US8394965B2 (en) | 2013-03-12 |
| EP2097431B1 (fr) | 2015-03-25 |
| EP2097431A1 (fr) | 2009-09-09 |
| CN103601758A (zh) | 2014-02-26 |
| CN103601758B (zh) | 2017-09-08 |
| IN2009KN02409A (OSRAM) | 2015-08-07 |
| JP2010511017A (ja) | 2010-04-08 |
| EP2476688B1 (fr) | 2017-06-14 |
| BRPI0721051B1 (pt) | 2017-05-09 |
| FR2909382A1 (fr) | 2008-06-06 |
| WO2008065187A1 (fr) | 2008-06-05 |
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