DE19521340A1 - Verfahren zur Herstellung von Hydroxybiarylphosphanen und neue Verbindungen aus dieser Stoffgruppe - Google Patents
Verfahren zur Herstellung von Hydroxybiarylphosphanen und neue Verbindungen aus dieser StoffgruppeInfo
- Publication number
- DE19521340A1 DE19521340A1 DE19521340A DE19521340A DE19521340A1 DE 19521340 A1 DE19521340 A1 DE 19521340A1 DE 19521340 A DE19521340 A DE 19521340A DE 19521340 A DE19521340 A DE 19521340A DE 19521340 A1 DE19521340 A1 DE 19521340A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- alkyl
- different
- same
- alkoxy
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 15
- 239000000126 substance Substances 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 53
- OMDCSPXITNMPHV-UHFFFAOYSA-N 2h-oxaphosphinine Chemical compound O1PC=CC=C1 OMDCSPXITNMPHV-UHFFFAOYSA-N 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- -1 1-phenylnaphthyl Chemical group 0.000 claims description 31
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 30
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000012074 organic phase Substances 0.000 claims description 15
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- 239000004305 biphenyl Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004437 phosphorous atom Chemical group 0.000 claims description 11
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical group C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 8
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 8
- 150000005840 aryl radicals Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052744 lithium Chemical group 0.000 claims description 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 150000003738 xylenes Chemical class 0.000 claims description 4
- 229910052783 alkali metal Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 101150034533 ATIC gene Proteins 0.000 claims 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 150000002902 organometallic compounds Chemical class 0.000 description 15
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 229940078552 o-xylene Drugs 0.000 description 11
- UBEUAZASIHVFOB-UHFFFAOYSA-N 6-chlorobenzo[c][2,1]benzoxaphosphinine Chemical compound C1=CC=C2P(Cl)OC3=CC=CC=C3C2=C1 UBEUAZASIHVFOB-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 229950011260 betanaphthol Drugs 0.000 description 6
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- ZOGYOOUMDVKYLM-UHFFFAOYSA-N phosphane phosphorous acid Chemical compound P.OP(O)O ZOGYOOUMDVKYLM-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FFRRWYBYHUHBRJ-UHFFFAOYSA-N 2-(2-diphenylphosphanylphenyl)-6-phenylphenol Chemical group OC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FFRRWYBYHUHBRJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- DTKMKZYEOXZPQZ-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=C[C-]=C1 DTKMKZYEOXZPQZ-UHFFFAOYSA-M 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RMZSHINKYBUAAS-UHFFFAOYSA-N 1-(2-dicyclohexylphosphanylphenyl)naphthalen-2-ol Chemical compound OC1=CC=C2C=CC=CC2=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 RMZSHINKYBUAAS-UHFFFAOYSA-N 0.000 description 1
- UFBBLPOVLLKPOF-UHFFFAOYSA-N 1-(2-diphenylphosphanylphenyl)naphthalen-2-ol Chemical compound OC1=CC=C2C=CC=CC2=C1C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UFBBLPOVLLKPOF-UHFFFAOYSA-N 0.000 description 1
- RKMPHIQXDRZGPJ-UHFFFAOYSA-N 1-[2-(2-cyclohexylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-ol Chemical group OC1=CC=C2C=CC=CC2=C1C(C1=CC=CC=C1C=C1)=C1PC1=CC=CC=C1C1CCCCC1 RKMPHIQXDRZGPJ-UHFFFAOYSA-N 0.000 description 1
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YAWGDHITVCZXQZ-UHFFFAOYSA-N 2-(2-diphenylphosphanylnaphthalen-1-yl)phenol Chemical compound OC1=CC=CC=C1C1=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC2=CC=CC=C12 YAWGDHITVCZXQZ-UHFFFAOYSA-N 0.000 description 1
- RTFMVYDUGUHDJT-UHFFFAOYSA-N 2-(2-diphenylphosphanylphenyl)phenol Chemical group OC1=CC=CC=C1C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RTFMVYDUGUHDJT-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- OGYLYDJDYRFALF-UHFFFAOYSA-N 2-[2-(5h-benzo[b]phosphindol-1-yl)phenyl]phenol Chemical group OC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=C1C1=CC=CC=C1P2 OGYLYDJDYRFALF-UHFFFAOYSA-N 0.000 description 1
- RSTGAYUHHLSABS-UHFFFAOYSA-N 2-[2-[2-(2-methoxyphenyl)phenyl]phosphanylphenyl]phenol Chemical group COC1=CC=CC=C1C1=CC=CC=C1PC1=CC=CC=C1C1=CC=CC=C1O RSTGAYUHHLSABS-UHFFFAOYSA-N 0.000 description 1
- YKTCURWYELMHHJ-UHFFFAOYSA-N 2-[2-[2-(2-methylphenyl)phenyl]phosphanylphenyl]phenol Chemical group CC1=CC=CC=C1C1=CC=CC=C1PC1=CC=CC=C1C1=CC=CC=C1O YKTCURWYELMHHJ-UHFFFAOYSA-N 0.000 description 1
- HNMNCKZOBHXCSV-UHFFFAOYSA-N 2-[2-bis(3-fluorophenyl)phosphanylnaphthalen-1-yl]phenol Chemical compound OC1=CC=CC=C1C1=C(P(C=2C=C(F)C=CC=2)C=2C=C(F)C=CC=2)C=CC2=CC=CC=C12 HNMNCKZOBHXCSV-UHFFFAOYSA-N 0.000 description 1
- OIHANGGOESCJBV-UHFFFAOYSA-N 2-[2-di(propan-2-yl)phosphanylphenyl]phenol Chemical group CC(C)P(C(C)C)C1=CC=CC=C1C1=CC=CC=C1O OIHANGGOESCJBV-UHFFFAOYSA-N 0.000 description 1
- FFYRVIODLLQJBT-UHFFFAOYSA-N 2-[3-(2-methoxyphenyl)-2-phosphanylnaphthalen-1-yl]phenol Chemical compound COC1=C(C=CC=C1)C=1C(=C(C2=CC=CC=C2C=1)C1=C(C=CC=C1)O)P FFYRVIODLLQJBT-UHFFFAOYSA-N 0.000 description 1
- TZATUPLHDXUMDO-UHFFFAOYSA-N 2-[3-(2-methylphenyl)-2-phosphanylnaphthalen-1-yl]phenol Chemical compound CC1=C(C=CC=C1)C=1C(=C(C2=CC=CC=C2C=1)C1=C(C=CC=C1)O)P TZATUPLHDXUMDO-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- FNGXTZFCSAZIIY-UHFFFAOYSA-N 5-chloronaphtho[2,1-c][2,1]benzoxaphosphinine Chemical compound C1=CC=C2P(Cl)OC3=CC=C(C=CC=C4)C4=C3C2=C1 FNGXTZFCSAZIIY-UHFFFAOYSA-N 0.000 description 1
- KDXZQAGKGPCJBV-UHFFFAOYSA-N 6-chloronaphtho[2,1-c][1,2]benzoxaphosphinine Chemical compound C1=CC2=CC=CC=C2C2=C1P(Cl)OC1=CC=CC=C12 KDXZQAGKGPCJBV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GDQVRTXTGHTUKO-UHFFFAOYSA-N C1=CC=C2C(=C1)C=C(C(=C2C3=CC=CC=C3O)P)C4=CC=C(C=C4)F Chemical compound C1=CC=C2C(=C1)C=C(C(=C2C3=CC=CC=C3O)P)C4=CC=C(C=C4)F GDQVRTXTGHTUKO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PZIIGUMPOSVMSD-UHFFFAOYSA-M [Br-].C1=CC=C2C([Mg+])=CC=CC2=C1 Chemical compound [Br-].C1=CC=C2C([Mg+])=CC=CC2=C1 PZIIGUMPOSVMSD-UHFFFAOYSA-M 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- SHAKXLPGFQFNJG-UHFFFAOYSA-M magnesium;1,3-bis(trifluoromethyl)benzene-5-ide;bromide Chemical compound [Mg+2].[Br-].FC(F)(F)C1=C[C-]=CC(C(F)(F)F)=C1 SHAKXLPGFQFNJG-UHFFFAOYSA-M 0.000 description 1
- FCPRDUXJWIUVPZ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=CC=[C-]1 FCPRDUXJWIUVPZ-UHFFFAOYSA-M 0.000 description 1
- YAMQOOCGNXAQGW-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC=[C-]1 YAMQOOCGNXAQGW-UHFFFAOYSA-M 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical class C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C07C45/505—Asymmetric hydroformylation
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5068—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure >P-Hal
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5081—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure >P-Het, Het being an heteroatom different from Hal or Metal
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19521340A DE19521340A1 (de) | 1995-06-12 | 1995-06-12 | Verfahren zur Herstellung von Hydroxybiarylphosphanen und neue Verbindungen aus dieser Stoffgruppe |
| IN791CA1996 IN188603B (enExample) | 1995-06-12 | 1996-05-01 | |
| EP96108972A EP0748811A1 (de) | 1995-06-12 | 1996-06-05 | Verfahren zur Herstellung von Hydroxybiarylphosphanen und neue Verbindungen aus dieser Stoffgruppe |
| BR9602731A BR9602731A (pt) | 1995-06-12 | 1996-06-11 | Processo para a preparação de hidroxibiarilfosfinas e hidroxibiarilfosfina assim obtidas |
| US08/661,629 US5789623A (en) | 1995-06-12 | 1996-06-11 | Process for the preparation of hydroxybiarylphosphines and novel compounds of this group of substances |
| JP8149469A JPH093081A (ja) | 1995-06-12 | 1996-06-11 | ヒドロキシビアリールホスフィンの製造方法及びこの物質のグループに属する新規化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19521340A DE19521340A1 (de) | 1995-06-12 | 1995-06-12 | Verfahren zur Herstellung von Hydroxybiarylphosphanen und neue Verbindungen aus dieser Stoffgruppe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19521340A1 true DE19521340A1 (de) | 1996-12-19 |
Family
ID=7764184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19521340A Withdrawn DE19521340A1 (de) | 1995-06-12 | 1995-06-12 | Verfahren zur Herstellung von Hydroxybiarylphosphanen und neue Verbindungen aus dieser Stoffgruppe |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5789623A (enExample) |
| EP (1) | EP0748811A1 (enExample) |
| JP (1) | JPH093081A (enExample) |
| BR (1) | BR9602731A (enExample) |
| DE (1) | DE19521340A1 (enExample) |
| IN (1) | IN188603B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0850946A1 (de) * | 1996-12-24 | 1998-07-01 | Ciba SC Holding AG | Cyclische Phosphinsäurederivate als Stabilisatoren |
| US20040224364A1 (en) * | 2003-05-09 | 2004-11-11 | Rieke Metals, Inc. | Organo-zinc compounds |
| DE102005030400A1 (de) * | 2005-06-27 | 2006-12-28 | Archimica Gmbh | Verfahren zur Herstellung von Arylaminen, Arylethern und Arylthioethern |
| DE102005045132A1 (de) * | 2005-09-22 | 2007-03-29 | Archimica Gmbh | Verfahren zur Herstellung von 2-Arylcarbonylverbindungen, 2-Arylestern und 2-Arylnitrilen sowie ihrer heteroaromatischen Analoga |
| US8272987B2 (en) * | 2009-10-15 | 2012-09-25 | GM Global Technology Operations LLC | Single planetary, single motor/generator hybrid powertrain with three or more operating modes |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0503884A1 (en) * | 1991-03-12 | 1992-09-16 | Takasago International Corporation | Optically active diphenylphosphino-binaphtyl compounds and catalytic transition metal complexes thereof |
| WO1993005090A1 (en) * | 1991-08-29 | 1993-03-18 | Basf Corporation | Environmental etch resistant, two-component, coating composition, method of coating therewith, and coating obtained therefrom |
| EP0614901A1 (en) * | 1993-03-12 | 1994-09-14 | Mitsubishi Gas Chemical Company, Inc. | Phosphine compound and transition metal-phosphine complex containing the same as ligand |
| EP0614903A2 (en) * | 1993-03-12 | 1994-09-14 | Takasago International Corporation | Phosphine compounds, complexes containing the phosphine compounds as ligands, process for producing optically active aldehydes using the phosphine compounds, or complexes, and 4-[(R)-1' formylethyl]azetidin-2-one derivatives |
| EP0614870A2 (en) * | 1993-03-12 | 1994-09-14 | Mitsubishi Gas Chemical Company, Inc. | Process for producing optically active aldehydes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5530150A (en) * | 1993-03-12 | 1996-06-25 | Takasago International Corporation | Phosphine compound, complex containing the phosphine compound as ligand, process for producing optically active aldehyde using the phosphine compound or the complex, and 4-[(R)-1'-formylethyl]azetidin-2-one derivatives |
| US5523437A (en) * | 1993-10-07 | 1996-06-04 | Sumitomo Chemical Co., Ltd. | Tertiary phosphine compound and transition metal complex comprising the same as ligand |
-
1995
- 1995-06-12 DE DE19521340A patent/DE19521340A1/de not_active Withdrawn
-
1996
- 1996-05-01 IN IN791CA1996 patent/IN188603B/en unknown
- 1996-06-05 EP EP96108972A patent/EP0748811A1/de not_active Withdrawn
- 1996-06-11 JP JP8149469A patent/JPH093081A/ja active Pending
- 1996-06-11 BR BR9602731A patent/BR9602731A/pt not_active IP Right Cessation
- 1996-06-11 US US08/661,629 patent/US5789623A/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0503884A1 (en) * | 1991-03-12 | 1992-09-16 | Takasago International Corporation | Optically active diphenylphosphino-binaphtyl compounds and catalytic transition metal complexes thereof |
| WO1993005090A1 (en) * | 1991-08-29 | 1993-03-18 | Basf Corporation | Environmental etch resistant, two-component, coating composition, method of coating therewith, and coating obtained therefrom |
| EP0614901A1 (en) * | 1993-03-12 | 1994-09-14 | Mitsubishi Gas Chemical Company, Inc. | Phosphine compound and transition metal-phosphine complex containing the same as ligand |
| EP0614903A2 (en) * | 1993-03-12 | 1994-09-14 | Takasago International Corporation | Phosphine compounds, complexes containing the phosphine compounds as ligands, process for producing optically active aldehydes using the phosphine compounds, or complexes, and 4-[(R)-1' formylethyl]azetidin-2-one derivatives |
| EP0614870A2 (en) * | 1993-03-12 | 1994-09-14 | Mitsubishi Gas Chemical Company, Inc. | Process for producing optically active aldehydes |
Non-Patent Citations (8)
| Title |
|---|
| J. Chem. Soc., Chem. Comm. (1995), (15) 1533-34 * |
| J. Org. Chem. (1993) 58 (7), 1945-8 * |
| J. Organomet. Chem. (1995) 499 (1-2), 167-71 * |
| JACS (1993) 115 (15), 7033-34 * |
| JP 05255353 A (= CA 120:218 162) * |
| Tetrahedron Letters (1994) 35 (13), 2023-26 * |
| Tetrahedron Letters (1994) 35 (43), 7981-82 * |
| Zh. Obshch. Khim. (1972), 42(1),93-6 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US5789623A (en) | 1998-08-04 |
| IN188603B (enExample) | 2002-10-19 |
| JPH093081A (ja) | 1997-01-07 |
| BR9602731A (pt) | 1998-09-08 |
| EP0748811A1 (de) | 1996-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: CELANESE CHEMICALS EUROPE GMBH, 60439 FRANKFURT, D |
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| 8127 | New person/name/address of the applicant |
Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH, 65929 FRANKF |
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| 8127 | New person/name/address of the applicant |
Owner name: ARCHIMICA GMBH, 65929 FRANKFURT, DE |
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| 8130 | Withdrawal |