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 |
|---|---|---|---|
| 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 (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 (enExample) |
| EP (2) | EP2097431B1 (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 |
|---|---|---|---|---|
| EP2803658A1 (en) | 2009-02-03 | 2014-11-19 | IDENIX Pharmaceuticals, Inc. | Phosphinate ruthenium complexes |
| 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 |
| JP6290195B2 (ja) | 2012-06-13 | 2018-03-07 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 大環状ケトンの製造方法 |
| 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 |
| WO2014201300A1 (en) | 2013-06-12 | 2014-12-18 | Trustees Of Boston College | Catalysts for efficient z-selective metathesis |
| 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 |
| CN108473390B (zh) | 2015-11-18 | 2022-08-09 | 普罗维维公司 | 通过烯烃复分解生产脂肪烯烃衍生物 |
| HUE053613T2 (hu) | 2015-11-18 | 2021-07-28 | Provivi Inc | Mikroorganizmusok rovarferomonok és kapcsolódó vegyületek elõállítására |
| WO2017100585A1 (en) * | 2015-12-10 | 2017-06-15 | Materia, Inc. | Olefin metathesis catalysts |
| AR110606A1 (es) | 2016-06-06 | 2019-04-17 | Provivi Inc | Producción semi-biosintética de alcoholes grasos y aldehídos grasos |
| US10688481B2 (en) | 2016-11-09 | 2020-06-23 | Ximo Ag | Ruthenium complexes useful for catalyzing metathesis reactions |
| HUE073559T2 (hu) | 2017-02-17 | 2026-01-28 | Provivi Inc | Feromonok és kapcsolódó anyagok szintézise olefin-metatézisen keresztül |
| FR3063290A1 (fr) | 2017-02-24 | 2018-08-31 | Stratoz | Procede de synthese de pheromones |
| JP7216018B2 (ja) | 2017-05-17 | 2023-01-31 | プロヴィヴィ インコーポレイテッド | 昆虫フェロモンの生成のための微生物及び関連する化合物 |
| 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 |
| KR102702569B1 (ko) | 2017-12-08 | 2024-09-06 | 아란세오 도이치란드 게엠베하 | 루테늄 착물 촉매를 사용하여 니트릴 고무를 생성하기 위한 방법 |
| 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 |
| 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 |
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 |
| 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 |
| ATE448019T1 (de) | 2000-08-10 | 2009-11-15 | Trustees Boston College | Wiederverwendbare methathese-katalysatoren |
| US6620955B1 (en) * | 2001-11-15 | 2003-09-16 | Richard L. Pederson | 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 |
| RU2435778C2 (ru) * | 2005-07-04 | 2011-12-10 | Заннан Сайтех Ко., Лтд. | Лиганд комплекса рутения, комплекс рутения, катализатор комплекса рутения и способы его получения и применения |
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2007
- 2007-01-30 FR FR0700634A patent/FR2909382B1/fr not_active Expired - Fee Related
- 2007-11-30 EP EP07847578.7A patent/EP2097431B1/fr active Active
- 2007-11-30 US US12/517,322 patent/US8394965B2/en active Active
- 2007-11-30 IN IN2409KON2009 patent/IN2009KN02409A/en unknown
- 2007-11-30 JP JP2009538722A patent/JP5284269B2/ja not_active Expired - Fee Related
- 2007-11-30 CA CA002671082A patent/CA2671082A1/fr not_active Abandoned
- 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
- 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
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| Publication number | Publication date |
|---|---|
| CN103601758B (zh) | 2017-09-08 |
| JP2010511017A (ja) | 2010-04-08 |
| CN103601758A (zh) | 2014-02-26 |
| EP2097431B1 (fr) | 2015-03-25 |
| BRPI0721051A2 (pt) | 2014-07-29 |
| EP2476688A1 (fr) | 2012-07-18 |
| FR2909382A1 (fr) | 2008-06-06 |
| EP2097431A1 (fr) | 2009-09-09 |
| US20130144060A1 (en) | 2013-06-06 |
| US8394965B2 (en) | 2013-03-12 |
| WO2008065187A1 (fr) | 2008-06-05 |
| BRPI0721051B1 (pt) | 2017-05-09 |
| US8586757B2 (en) | 2013-11-19 |
| IN2009KN02409A (enExample) | 2015-08-07 |
| US20100087644A1 (en) | 2010-04-08 |
| JP5284269B2 (ja) | 2013-09-11 |
| FR2909382B1 (fr) | 2009-01-23 |
| EP2476688B1 (fr) | 2017-06-14 |
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