ES2217245T3 - Nuevo catalizador saleno quiral y metodos de obtencion de compuestos quirales a partir de epoxidos racemicos utilizando el nuevo catalizador. - Google Patents
Nuevo catalizador saleno quiral y metodos de obtencion de compuestos quirales a partir de epoxidos racemicos utilizando el nuevo catalizador.Info
- Publication number
- ES2217245T3 ES2217245T3 ES02743918T ES02743918T ES2217245T3 ES 2217245 T3 ES2217245 T3 ES 2217245T3 ES 02743918 T ES02743918 T ES 02743918T ES 02743918 T ES02743918 T ES 02743918T ES 2217245 T3 ES2217245 T3 ES 2217245T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- chiral
- catalyst
- obtaining
- boron
- 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.)
- Expired - Lifetime
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 201
- 150000001875 compounds Chemical class 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 10
- 229910052796 boron Inorganic materials 0.000 claims abstract description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- -1 phosphoryl group Chemical group 0.000 claims abstract description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003172 aldehyde group Chemical group 0.000 claims abstract description 7
- 125000004429 atom Chemical group 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000468 ketone group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 7
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 5
- 125000004185 ester group Chemical group 0.000 claims abstract description 5
- 125000001033 ether group Chemical group 0.000 claims abstract description 5
- 125000000879 imine group Chemical group 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 5
- 125000000101 thioether group Chemical group 0.000 claims abstract description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 3
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 3
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 3
- 125000000854 selenoether group Chemical group 0.000 claims abstract description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 38
- 239000011780 sodium chloride Substances 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 35
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006460 hydrolysis reaction Methods 0.000 claims description 17
- 229910015900 BF3 Inorganic materials 0.000 claims description 16
- 230000007062 hydrolysis Effects 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 230000000707 stereoselective effect Effects 0.000 claims description 11
- 150000000180 1,2-diols Chemical class 0.000 claims description 10
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- KTNDYCJNKWCSKC-UHFFFAOYSA-K [B+3].C(CC)O.[F-].[F-].[F-] Chemical compound [B+3].C(CC)O.[F-].[F-].[F-] KTNDYCJNKWCSKC-UHFFFAOYSA-K 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 150000003346 selenoethers Chemical class 0.000 claims description 2
- MJCYPBSRKLJZTB-UHFFFAOYSA-N trifluoroborane;dihydrate Chemical compound O.O.FB(F)F MJCYPBSRKLJZTB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- DVJSDNKGCNXYQR-UHFFFAOYSA-N CO.[B] Chemical compound CO.[B] DVJSDNKGCNXYQR-UHFFFAOYSA-N 0.000 claims 1
- GIYJCMBFHXKECH-UHFFFAOYSA-N [B].CC(O)=O Chemical compound [B].CC(O)=O GIYJCMBFHXKECH-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- HVABKWYVQHSGHW-UHFFFAOYSA-N boron;ethanamine Chemical compound [B].CCN HVABKWYVQHSGHW-UHFFFAOYSA-N 0.000 claims 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims 1
- KWGASIUWELSTHP-UHFFFAOYSA-N boron;phenol Chemical compound [B].OC1=CC=CC=C1 KWGASIUWELSTHP-UHFFFAOYSA-N 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- JUYWKECPOZQAQT-UHFFFAOYSA-N methyl(sulfanylidene)borane Chemical compound CB=S JUYWKECPOZQAQT-UHFFFAOYSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- 230000000052 comparative effect Effects 0.000 description 44
- 150000002924 oxiranes Chemical class 0.000 description 38
- 230000003287 optical effect Effects 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000003446 ligand Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 230000009257 reactivity Effects 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000001994 activation Methods 0.000 description 16
- 230000006340 racemization Effects 0.000 description 16
- 238000003756 stirring Methods 0.000 description 14
- BRLQWZUYTZBJKN-GSVOUGTGSA-N (+)-Epichlorohydrin Chemical compound ClC[C@@H]1CO1 BRLQWZUYTZBJKN-GSVOUGTGSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- FYNXDGNCEBQLGC-LOYHVIPDSA-N 2,4-ditert-butyl-6-[[(1R,2R)-2-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]cyclohexyl]iminomethyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=N[C@H]2[C@@H](CCCC2)N=CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O FYNXDGNCEBQLGC-LOYHVIPDSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 7
- 238000004508 fractional distillation Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
- 235000013373 food additive Nutrition 0.000 description 3
- 239000002778 food additive Substances 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- FYNXDGNCEBQLGC-KYJUHHDHSA-N 2,4-ditert-butyl-6-[[(1S,2S)-2-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]cyclohexyl]iminomethyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=N[C@@H]2[C@H](CCCC2)N=CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O FYNXDGNCEBQLGC-KYJUHHDHSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-VKHMYHEASA-N (-)-Epichlorohydrin Chemical compound ClC[C@H]1CO1 BRLQWZUYTZBJKN-VKHMYHEASA-N 0.000 description 1
- BMRWNKZVCUKKSR-SCSAIBSYSA-N (R)-butane-1,2-diol Chemical compound CC[C@@H](O)CO BMRWNKZVCUKKSR-SCSAIBSYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-BYPYZUCNSA-N (S)-butane-1,2-diol Chemical compound CC[C@H](O)CO BMRWNKZVCUKKSR-BYPYZUCNSA-N 0.000 description 1
- AWMVMTVKBNGEAK-MRVPVSSYSA-N (S)-styrene oxide Chemical compound C1O[C@H]1C1=CC=CC=C1 AWMVMTVKBNGEAK-MRVPVSSYSA-N 0.000 description 1
- SFXNZFATUMWBHR-UHFFFAOYSA-N 2-morpholin-4-yl-2-pyridin-3-ylacetonitrile Chemical compound C=1C=CN=CC=1C(C#N)N1CCOCC1 SFXNZFATUMWBHR-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KQLBEMXDVMXJMY-UHFFFAOYSA-K C[B+3]=S.[F-].[F-].[F-] Chemical compound C[B+3]=S.[F-].[F-].[F-] KQLBEMXDVMXJMY-UHFFFAOYSA-K 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- GAZUWKXRTMWZDJ-UHFFFAOYSA-K [B+3].[F-].[F-].[F-].Oc1ccccc1 Chemical compound [B+3].[F-].[F-].[F-].Oc1ccccc1 GAZUWKXRTMWZDJ-UHFFFAOYSA-K 0.000 description 1
- KWZNMNHMFKPHBS-UHFFFAOYSA-N [B].FP(F)(F)=O Chemical compound [B].FP(F)(F)=O KWZNMNHMFKPHBS-UHFFFAOYSA-N 0.000 description 1
- IVNLGOHTAQHXDP-UHFFFAOYSA-K [F-].[F-].[F-].C(C)(=O)O.[B+3] Chemical compound [F-].[F-].[F-].C(C)(=O)O.[B+3] IVNLGOHTAQHXDP-UHFFFAOYSA-K 0.000 description 1
- PCBWXDJXIIOMSL-UHFFFAOYSA-K [F-].[F-].[F-].C(C)N.[B+3] Chemical compound [F-].[F-].[F-].C(C)N.[B+3] PCBWXDJXIIOMSL-UHFFFAOYSA-K 0.000 description 1
- VIAZSEYHFKDLSH-UHFFFAOYSA-K [F-].[F-].[F-].CO.[B+3] Chemical compound [F-].[F-].[F-].CO.[B+3] VIAZSEYHFKDLSH-UHFFFAOYSA-K 0.000 description 1
- IEUHHDADYONAKC-UHFFFAOYSA-K [F-].[F-].[F-].O1CCCC1.[B+3] Chemical compound [F-].[F-].[F-].O1CCCC1.[B+3] IEUHHDADYONAKC-UHFFFAOYSA-K 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- LVZGQWKTUCVPBQ-UHFFFAOYSA-N acetic acid;trifluoroborane Chemical compound CC(O)=O.FB(F)F LVZGQWKTUCVPBQ-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- AOBOMOUUYYHMOX-UHFFFAOYSA-N diethylboron Chemical compound CC[B]CC AOBOMOUUYYHMOX-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- DPDXVBIWZBJGSX-XUTVFYLZSA-N isoboonein Chemical compound C1C(=O)OC[C@@H]2[C@@H](C)[C@@H](O)C[C@@H]21 DPDXVBIWZBJGSX-XUTVFYLZSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
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- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- 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
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/403—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing iron group metals or copper
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/48—Ring-opening reactions
- B01J2231/482—Ring-opening reactions asymmetric reactions, e.g. kinetic resolution of racemates
- B01J2231/485—Ring-opening reactions asymmetric reactions, e.g. kinetic resolution of racemates kinetic resolution of epoxide racemates
- B01J2231/487—Ring-opening reactions asymmetric reactions, e.g. kinetic resolution of racemates kinetic resolution of epoxide racemates by hydrolysis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/75—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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/0252—Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde
-
- 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
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
-
- 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
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/64—Molybdenum
-
- 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
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| KR2001037081 | 2001-06-27 | ||
| KR20010037081 | 2001-06-27 | ||
| KR2002035467 | 2002-06-24 | ||
| KR1020020035467A KR100368002B1 (en) | 2001-06-27 | 2002-06-24 | Chiral salen catalyst and process for preparing chiral compounds from racemic epoxy compounds using the same |
Publications (1)
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| ES2217245T3 true ES2217245T3 (es) | 2004-11-01 |
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| CN1281320C (zh) | 2001-04-18 | 2006-10-25 | 住友化学工业株式会社 | 络合物催化剂、该络合物催化剂的制造方法以及使用该络合物催化剂的醇衍生物的制造方法 |
| DE10130229A1 (de) * | 2001-06-22 | 2003-01-02 | Celanese Ventures Gmbh | Non-Metallocene, Verfahren zur Herstellung von diesen und deren Verwendung zur Polymerisation von Olefinen |
| US6639087B2 (en) * | 2001-08-22 | 2003-10-28 | Rhodia Pharma Solutions Inc. | Kinetic resolution method |
| UA79300C2 (en) * | 2002-08-12 | 2007-06-11 | Janssen Pharmaceutica Nv | N-aryl piperidine substituted biphenylcarboxamides as inhibitors of apolipoprotein b secretion |
| EP1469006A3 (de) * | 2003-02-12 | 2005-03-16 | Bayer Chemicals AG | Verfahren zur Reduktion von Ketocarbonsäureestern |
| ATE338050T1 (de) * | 2003-02-12 | 2006-09-15 | Saltigo Gmbh | Verfahren zur asymmetrischen hydrierung von ketocarbonsäureestern |
| TWI258478B (en) | 2003-10-31 | 2006-07-21 | Arena Pharm Inc | Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof |
| US7304172B2 (en) * | 2004-10-08 | 2007-12-04 | Cornell Research Foundation, Inc. | Polycarbonates made using highly selective catalysts |
| PE20060949A1 (es) | 2004-12-23 | 2006-10-11 | Arena Pharm Inc | Derivados fusionados de pirazol como agonistas del receptor de niacina |
| US8207365B2 (en) * | 2005-03-14 | 2012-06-26 | Georgia Tech Research Corporation | Polymeric salen compounds and methods thereof |
| WO2007089022A1 (ja) * | 2006-02-01 | 2007-08-09 | Sumitomo Chemical Company, Limited | 光学活性なアルコール化合物の製造方法 |
| US7906667B2 (en) | 2006-02-01 | 2011-03-15 | Sumitomo Chemical Company, Limited | Method for producing optically active alcohol compound |
| US20090286968A1 (en) | 2008-04-25 | 2009-11-19 | Auburn University | 2-Quinoxalinol Salen Compounds and Uses Thereof |
| WO2009137540A1 (en) | 2008-05-09 | 2009-11-12 | Cornell University | Polymers of ethylene oxide and carbon dioxide |
| CN101328264B (zh) * | 2008-07-10 | 2010-12-15 | 浙江大学 | 用离子液体支载催化剂制备聚碳酸酯的方法 |
| SG10201701421PA (en) | 2008-08-22 | 2017-04-27 | Novomer Inc | Catalysts and methods for polymer synthesis |
| NO2337809T3 (enExample) | 2008-09-08 | 2017-12-30 | ||
| EP2342258B1 (en) | 2008-09-17 | 2015-11-11 | Novomer, Inc. | Purification of polycarbonates |
| CA2742119C (en) | 2008-11-01 | 2018-05-29 | Novomer, Inc. | Polycarbonate block copolymers |
| CN102665406B (zh) | 2009-12-24 | 2016-03-09 | 诺沃梅尔公司 | 合成多环胍化合物的方法 |
| JP2013539802A (ja) | 2010-09-14 | 2013-10-28 | ノボマー， インコーポレイテッド | ポリマー合成の触媒および方法 |
| CN101967165B (zh) * | 2010-09-21 | 2012-09-05 | 中国科学院上海有机化学研究所 | 桥链双希夫碱-钴络合物及其合成方法和用途 |
| CN103228137B (zh) | 2010-09-22 | 2018-11-27 | 沙特阿美技术公司 | 取代的水杨醛衍生物的合成 |
| HUE036462T2 (hu) | 2011-05-09 | 2018-07-30 | Saudi Aramco Tech Co | Polimer készítmények és eljárások |
| CN102295579B (zh) * | 2011-06-22 | 2014-05-21 | 安庆金泉药业有限公司 | 一种(r)-4-氰基-3-羟基丁酸乙酯的合成工艺 |
| IN2014CN01299A (enExample) | 2011-07-25 | 2015-04-24 | Novomer Inc | |
| US9403861B2 (en) | 2011-12-11 | 2016-08-02 | Novomer, Inc. | Salen complexes with dianionic counterions |
| CN102580777B (zh) * | 2011-12-19 | 2013-11-20 | 浙江大学 | 负载型salen锰配合物催化剂及其制备方法和应用 |
| WO2013096602A1 (en) | 2011-12-20 | 2013-06-27 | Novomer, Inc. | Methods for polymer synthesis |
| CN103301882B (zh) * | 2012-03-16 | 2015-04-22 | 中国科学院大连化学物理研究所 | 一种用于拆分外消旋环氧烷烃的催化剂及其应用 |
| EP2838954B1 (en) | 2012-04-16 | 2024-09-18 | Saudi Aramco Technologies Company | Adhesive compositions and methods |
| JP6527080B2 (ja) | 2012-05-24 | 2019-06-05 | サウジ アラムコ テクノロジーズ カンパニー | ポリカーボネートポリオール組成物および方法 |
| JP6313305B2 (ja) | 2012-08-24 | 2018-04-18 | サウジ アラムコ テクノロジーズ カンパニー | 金属錯体 |
| CN108715630A (zh) | 2012-11-07 | 2018-10-30 | 沙特阿美技术公司 | 高强度聚氨酯泡沫组合物及方法 |
| US10308759B2 (en) | 2014-04-03 | 2019-06-04 | Saudi Aramco Technologies Company | Aliphatic polycarbonate polyol compositions |
| CN104610263B (zh) * | 2014-09-17 | 2016-06-29 | 成都理工大学 | 手性咪唑啉酮-酚 |
| CN104356098A (zh) * | 2014-11-10 | 2015-02-18 | 舒兰市金马化工有限公司 | 一种手性环氧氯丙烷的制备方法 |
| CN104607250B (zh) * | 2015-02-02 | 2016-11-30 | 舒兰市金马化工有限公司 | 一种多面体低聚倍半硅氧烷树枝状大分子催化剂及其应用 |
| CN104804044A (zh) * | 2015-03-10 | 2015-07-29 | 沈阳化工大学 | Ru(II)-Salen金属配合物及其制备方法 |
| CN107226797B (zh) * | 2016-08-29 | 2019-05-17 | 沈阳金久奇科技有限公司 | 一种手性化合物2，2-二甲基-3-(环氧乙烷-2-基)丙酸甲酯的制备方法 |
| JP2021522355A (ja) | 2018-04-18 | 2021-08-30 | サウジ アラムコ テクノロジーズ カンパニー | ポリ（アルキレンカーボネート）ポリマーの末端基異性化 |
| CN111097529B (zh) * | 2018-10-25 | 2023-05-02 | 中国石油化工股份有限公司 | 高性能纳米笼限域催化剂、制备方法及应用 |
| WO2020028606A1 (en) | 2018-08-02 | 2020-02-06 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| MA53727A (fr) | 2018-09-24 | 2021-12-29 | Saudi Aramco Tech Co | Copolymères séquencés de polycarbonate et procédés associés |
| EP4359460A1 (en) | 2021-06-23 | 2024-05-01 | Saudi Aramco Technologies Company | Polyol compositions and methods |
| CN117658953A (zh) * | 2023-12-04 | 2024-03-08 | 上海中化科技有限公司 | 手性环氧化合物、手性β-内酯及聚羟基脂肪酸酯的制备方法 |
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| US566393A (en) * | 1896-08-25 | Andrew fyrberg | ||
| US5637739A (en) | 1990-03-21 | 1997-06-10 | Research Corporation Technologies, Inc. | Chiral catalysts and catalytic epoxidation catalyzed thereby |
| DE4435158A1 (de) * | 1994-09-30 | 1996-04-04 | Degussa | Verfahren zur Herstellung von Salcomin |
| US6262278B1 (en) * | 1995-03-14 | 2001-07-17 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| US5665890A (en) * | 1995-03-14 | 1997-09-09 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| US6521561B1 (en) * | 1998-05-01 | 2003-02-18 | President And Fellows Of Harvard College | Main-group metal based asymmetric catalysts and applications thereof |
| US6720434B2 (en) * | 2000-05-24 | 2004-04-13 | Rstech Co., Ltd. | Process for preparing chiral compounds from recemic epoxides by using chiral salen catalysts |
| CA2489593C (en) * | 2002-06-13 | 2009-09-29 | Teva Pharmaceutical Industries Ltd | Epimerization of analogs of vitamin d |
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| CN1463272A (zh) | 2003-12-24 |
| AU2002345388A1 (en) | 2003-03-03 |
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| EP1292602B1 (en) | 2004-04-07 |
| WO2003002582A1 (en) | 2003-01-09 |
| JP3968076B2 (ja) | 2007-08-29 |
| EP1292602A1 (en) | 2003-03-19 |
| JP2004521740A (ja) | 2004-07-22 |
| CN1233648C (zh) | 2005-12-28 |
| US6884750B2 (en) | 2005-04-26 |
| DE60200346T2 (de) | 2005-03-24 |
| ATE263626T1 (de) | 2004-04-15 |
| DE60200346D1 (de) | 2004-05-13 |
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