CA2339165A1 - Preparation of organolithium and organophosphorus derivatives - Google Patents
Preparation of organolithium and organophosphorus derivatives Download PDFInfo
- Publication number
- CA2339165A1 CA2339165A1 CA002339165A CA2339165A CA2339165A1 CA 2339165 A1 CA2339165 A1 CA 2339165A1 CA 002339165 A CA002339165 A CA 002339165A CA 2339165 A CA2339165 A CA 2339165A CA 2339165 A1 CA2339165 A1 CA 2339165A1
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- Prior art keywords
- compound
- general formula
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- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 86
- 125000001979 organolithium group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 241
- 238000000034 method Methods 0.000 claims abstract description 208
- 230000008569 process Effects 0.000 claims abstract description 195
- 238000006243 chemical reaction Methods 0.000 claims abstract description 90
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 18
- 150000001768 cations Chemical class 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 45
- -1 dialkylamido Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 19
- 229910052744 lithium Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000006138 lithiation reaction Methods 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000003880 polar aprotic solvent Substances 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910004786 P-Li Inorganic materials 0.000 claims 1
- 229910004796 P—Li Inorganic materials 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 28
- 239000003054 catalyst Substances 0.000 abstract description 24
- 150000001340 alkali metals Chemical group 0.000 abstract description 17
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 8
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 39
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 37
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 34
- 238000004679 31P NMR spectroscopy Methods 0.000 description 33
- 150000003839 salts Chemical class 0.000 description 32
- 239000011734 sodium Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 26
- 229910052708 sodium Inorganic materials 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 24
- 239000002184 metal Substances 0.000 description 24
- 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 23
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 23
- 239000002253 acid Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 239000007788 liquid Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000007334 copolymerization reaction Methods 0.000 description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- PFCFKYSBIQBHAO-UHFFFAOYSA-N lithium;methoxybenzene Chemical compound [Li+].COC1=CC=CC=[C-]1 PFCFKYSBIQBHAO-UHFFFAOYSA-N 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229960004132 diethyl ether Drugs 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- ZDTNZJURPVUXPE-UHFFFAOYSA-N n-[bis[(2-methoxyphenyl)methyl]phosphanyl]-n-ethylethanamine Chemical compound C=1C=CC=C(OC)C=1CP(N(CC)CC)CC1=CC=CC=C1OC ZDTNZJURPVUXPE-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ITHPEWAHFNDNIO-UHFFFAOYSA-N triphosphane Chemical compound PPP ITHPEWAHFNDNIO-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- OKUDBXZACZBZJE-UHFFFAOYSA-N bis(2-methoxyethoxy)aluminum;sodium Chemical compound [Na].COCCO[Al]OCCOC OKUDBXZACZBZJE-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229940052303 ethers for general anesthesia Drugs 0.000 description 3
- ONOOVWPSEXAGAB-UHFFFAOYSA-N ethoxy-bis[(2-methoxyphenyl)methyl]phosphane Chemical compound C=1C=CC=C(OC)C=1CP(OCC)CC1=CC=CC=C1OC ONOOVWPSEXAGAB-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- AEOFYYUGLYQJHY-UHFFFAOYSA-N n-diphenylphosphanyl-n-ethylethanamine Chemical compound C=1C=CC=CC=1P(N(CC)CC)C1=CC=CC=C1 AEOFYYUGLYQJHY-UHFFFAOYSA-N 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 3
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 102220231544 rs281865209 Human genes 0.000 description 3
- BSFVCIYREAMMOJ-UHFFFAOYSA-N tris[(2-methoxyphenyl)methyl]phosphane Chemical group COC1=CC=CC=C1CP(CC=1C(=CC=CC=1)OC)CC1=CC=CC=C1OC BSFVCIYREAMMOJ-UHFFFAOYSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- ZIQNZEFIQWBNHV-UHFFFAOYSA-N 3,3-bis(bromomethyl)pentane Chemical compound CCC(CC)(CBr)CBr ZIQNZEFIQWBNHV-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XNZKCTXYNYAHQX-UHFFFAOYSA-N [3-[bis[(2-methoxyphenyl)methyl]phosphanyl]-2,2-dimethylpropyl]-bis[(2-methoxyphenyl)methyl]phosphane Chemical compound COC1=CC=CC=C1CP(CC(C)(C)CP(CC=1C(=CC=CC=1)OC)CC=1C(=CC=CC=1)OC)CC1=CC=CC=C1OC XNZKCTXYNYAHQX-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- BACGWSQQIAEILW-UHFFFAOYSA-N dibutyl(ethoxy)phosphane Chemical compound CCCCP(OCC)CCCC BACGWSQQIAEILW-UHFFFAOYSA-N 0.000 description 2
- FSMCRRSYPLYKAC-UHFFFAOYSA-N dibutylphosphane;sodium Chemical compound [Na].CCCCPCCCC FSMCRRSYPLYKAC-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- JCRCPEDXAHDCAJ-UHFFFAOYSA-N ethoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OCC)C1=CC=CC=C1 JCRCPEDXAHDCAJ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
-
- 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
- C07F9/504—Organo-phosphines containing a P-P bond
-
- 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
- C07F9/5077—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-Metal, including R2P-M+
-
- 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
- C07F9/5086—Preparation; Separation; Purification; Stabilisation from phosphonium salts as starting materials
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O
Landscapes
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98306254 | 1998-08-05 | ||
| EP98306254.8 | 1998-08-05 | ||
| EP98203587 | 1998-10-23 | ||
| EP98203587.5 | 1998-10-23 | ||
| PCT/EP1999/005748 WO2000008030A2 (en) | 1998-08-05 | 1999-08-03 | Preparation of organolithium and organophosphorus derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2339165A1 true CA2339165A1 (en) | 2000-02-17 |
Family
ID=26150804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002339165A Abandoned CA2339165A1 (en) | 1998-08-05 | 1999-08-03 | Preparation of organolithium and organophosphorus derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US6548708B1 (enExample) |
| EP (2) | EP1671976B1 (enExample) |
| JP (2) | JP5283807B2 (enExample) |
| CN (1) | CN1311791A (enExample) |
| AT (1) | ATE325126T1 (enExample) |
| AU (1) | AU746518B2 (enExample) |
| CA (1) | CA2339165A1 (enExample) |
| DE (1) | DE69931165T2 (enExample) |
| WO (1) | WO2000008030A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6548708B1 (en) * | 1998-08-05 | 2003-04-15 | Sri International | Preparation of biphosphine ligands for incorporation into catalytic complexes |
| DE102005005946A1 (de) * | 2005-02-10 | 2006-08-17 | Basf Ag | Verfahren zur Herstellung tertiärer Phosphine |
| EP2213643A1 (en) | 2009-01-28 | 2010-08-04 | Hexion Specialty Chemicals Research Belgium S.A. | Process for the preparation of an allyl aryl ether by catalytic o-allylation |
| JP6068482B2 (ja) * | 2011-09-30 | 2017-01-25 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 精製プロセス |
| CN105111235B (zh) * | 2015-08-14 | 2017-04-19 | 张玉清 | 一种烷基二苯基膦及制备烷基二苯基膦联产烷基苯的方法 |
| CN108586528B (zh) * | 2018-02-08 | 2020-03-24 | 新乡市润宇新材料科技有限公司 | 一种2，2′-双二苯基膦基-1，1′-联萘的合成方法 |
| JP2022078365A (ja) * | 2019-03-25 | 2022-05-25 | 丸善石油化学株式会社 | リン化合物の製造方法 |
| CN110669071B (zh) * | 2019-10-10 | 2022-03-29 | 黄河三角洲京博化工研究院有限公司 | 一种聚酮配体1,3-双[双(2-甲氧基苯基)膦基]丙烷的合成方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3131204A (en) | 1962-02-09 | 1964-04-28 | Grace W R & Co | Novel diquaternary aminophosphonium compounds |
| US3099691A (en) * | 1962-07-24 | 1963-07-30 | American Cyanamid Co | Preparation of organic phosphines from phosphorus, an alkyl halide and an organic lithium or sodium compound |
| IL27446A (en) | 1966-03-22 | 1972-04-27 | Ceskoslovenska Akademie Ved | Method of producing substituted aluminium hydrides |
| JPS4747014B1 (enExample) | 1970-03-17 | 1972-11-27 | ||
| US4006187A (en) | 1971-10-06 | 1977-02-01 | Lithium Corporation Of America | Preparation of aryllithium compounds by metalation |
| CH651051A5 (en) * | 1982-02-05 | 1985-08-30 | Hoffmann La Roche | Phosphorus compounds |
| DE3480845D1 (de) | 1983-04-06 | 1990-02-01 | Shell Int Research | Verfahren zur herstellung von polyketonen. |
| US4698447A (en) * | 1986-03-14 | 1987-10-06 | American Cyanamid Company | Process for producting 10-phenyl-10H-phenoxaphoshine |
| IE60363B1 (en) | 1986-05-27 | 1994-07-13 | Shell Int Research | Process for the preparation of polymers |
| CA1331201C (en) | 1987-04-08 | 1994-08-02 | Johannes Adrianus Van Doorn | Preparation of substituted diaryl phosphides |
| EP0290075A3 (en) | 1987-05-08 | 1989-02-22 | Shell Internationale Researchmaatschappij B.V. | Novel diaryl phosphides |
| EP0294000A2 (en) | 1987-06-05 | 1988-12-07 | Shell Internationale Researchmaatschappij B.V. | Novel diaryl phosphides |
| NL8800349A (nl) | 1988-01-12 | 1989-09-01 | Shell Int Research | Bereiding van fosfiden. |
| EP0364046A3 (en) | 1988-10-12 | 1991-03-27 | Shell Internationale Researchmaatschappij B.V. | Preparation of tetraaryldiphosphines |
| DE3911230A1 (de) | 1989-04-07 | 1990-10-11 | Hoechst Ag | Verfahren zur herstellung von alkylphosphonigsaeurediestern und/oder dialkylphosphinigsaeureestern |
| AU1926292A (en) | 1991-04-29 | 1992-12-21 | Fmc Corporation | Aryllithium process |
| US5288912A (en) * | 1993-02-12 | 1994-02-22 | Eastman Kodak Company | Process for the preparation of lithium diarylphosphides and alkylated derivatives thereof |
| JPH0747014A (ja) * | 1994-07-06 | 1995-02-21 | Suzuno Kasei Kk | カートリッジ式棒状化粧品繰出容器 |
| DE19526464C1 (de) | 1995-07-20 | 1997-03-06 | Hoechst Ag | Chirale tertiäre Phosphine und Verfahren zu ihrer Herstellung |
| DE69727460T2 (de) * | 1996-04-04 | 2004-07-01 | Bp Chemicals Ltd. | Eine verbindung, die in einer katalytischen zusammensetzung verwendbar ist |
| US6548708B1 (en) * | 1998-08-05 | 2003-04-15 | Sri International | Preparation of biphosphine ligands for incorporation into catalytic complexes |
| US6437164B1 (en) * | 1999-01-06 | 2002-08-20 | Yoshitomi Fine Chemicals, Ltd. | Process for the preparation of phosphonite compounds |
-
1999
- 1999-03-08 US US09/762,264 patent/US6548708B1/en not_active Expired - Lifetime
- 1999-08-03 AT AT99939459T patent/ATE325126T1/de not_active IP Right Cessation
- 1999-08-03 JP JP2000563663A patent/JP5283807B2/ja not_active Expired - Lifetime
- 1999-08-03 DE DE69931165T patent/DE69931165T2/de not_active Expired - Lifetime
- 1999-08-03 EP EP05019845.6A patent/EP1671976B1/en not_active Expired - Lifetime
- 1999-08-03 WO PCT/EP1999/005748 patent/WO2000008030A2/en not_active Ceased
- 1999-08-03 EP EP99939459A patent/EP1102771B1/en not_active Expired - Lifetime
- 1999-08-03 CN CN99809327A patent/CN1311791A/zh active Pending
- 1999-08-03 AU AU53743/99A patent/AU746518B2/en not_active Ceased
- 1999-08-03 CA CA002339165A patent/CA2339165A1/en not_active Abandoned
-
2003
- 2003-01-15 US US10/346,297 patent/US6720442B2/en not_active Expired - Lifetime
-
2004
- 2004-01-15 US US10/758,831 patent/US7067701B2/en not_active Expired - Lifetime
-
2011
- 2011-06-15 JP JP2011133748A patent/JP5421328B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000008030A2 (en) | 2000-02-17 |
| US20040147785A1 (en) | 2004-07-29 |
| US6720442B2 (en) | 2004-04-13 |
| DE69931165D1 (de) | 2006-06-08 |
| DE69931165T2 (de) | 2007-02-01 |
| EP1671976B1 (en) | 2014-12-03 |
| EP1671976A1 (en) | 2006-06-21 |
| JP2011201918A (ja) | 2011-10-13 |
| CN1311791A (zh) | 2001-09-05 |
| EP1102771B1 (en) | 2006-05-03 |
| JP5421328B2 (ja) | 2014-02-19 |
| AU5374399A (en) | 2000-02-28 |
| ATE325126T1 (de) | 2006-06-15 |
| JP5283807B2 (ja) | 2013-09-04 |
| AU746518B2 (en) | 2002-05-02 |
| WO2000008030A3 (en) | 2000-05-25 |
| US6548708B1 (en) | 2003-04-15 |
| EP1102771A2 (en) | 2001-05-30 |
| JP2002522441A (ja) | 2002-07-23 |
| US20030109754A1 (en) | 2003-06-12 |
| US7067701B2 (en) | 2006-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |