SK286152B6 - Spôsob prípravy acylfosfínov, acylfosfínoxidov a acylfosfínsulfidov - Google Patents

Spôsob prípravy acylfosfínov, acylfosfínoxidov a acylfosfínsulfidov Download PDF

Info

Publication number: SK286152B6
Authority: SK; Slovakia
Prior art keywords: alkyl; carbon atoms; reaction; phenyl; formula
Prior art date: 1998-11-30

Application number

SK727-2001A

Other languages

English (en)

Slovak (sk)

Other versions

SK7272001A3 (en

Inventor

David George Leppard

Eugen Eichenberger

Ren Kaeser

Gebhard Hug

Urs Schwendimann

Original Assignee

Ciba Specialty Chemicals Holding Inc.

Priority date (The priority date 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 date listed.)

1998-11-30

Filing date

1999-11-20

Publication date

2008-04-07

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25690294&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK286152(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-11-20 Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.

2001-12-03 Publication of SK7272001A3 publication Critical patent/SK7272001A3/sk

2008-04-07 Publication of SK286152B6 publication Critical patent/SK286152B6/sk

Links

150000003568 thioethers Chemical class 0.000 title claims abstract 4
238000004519 manufacturing process Methods 0.000 title description 3
-1 phosphorus halides Chemical class 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 60
238000006243 chemical reaction Methods 0.000 claims abstract description 50
239000000203 mixture Substances 0.000 claims abstract description 45
238000002360 preparation method Methods 0.000 claims abstract description 35
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 22
150000001875 compounds Chemical class 0.000 claims abstract description 22
229910052744 lithium Inorganic materials 0.000 claims abstract description 22
229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052749 magnesium Inorganic materials 0.000 claims abstract description 16
239000011777 magnesium Substances 0.000 claims abstract description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 14
150000001340 alkali metals Chemical class 0.000 claims abstract description 14
239000011593 sulfur Substances 0.000 claims abstract description 14
229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 12
239000011574 phosphorus Substances 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
150000004820 halides Chemical class 0.000 claims abstract description 10
239000000543 intermediate Substances 0.000 claims abstract description 10
239000003054 catalyst Substances 0.000 claims abstract description 9
238000002955 isolation Methods 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 52
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 27
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 20
235000010290 biphenyl Nutrition 0.000 claims description 19
239000004305 biphenyl Substances 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
239000000460 chlorine Chemical group 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 9
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
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 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000006839 xylylene group Chemical group 0.000 claims description 3
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
101150065749 Churc1 gene Proteins 0.000 claims description 2
102100038239 Protein Churchill Human genes 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
230000003647 oxidation Effects 0.000 abstract description 7
238000007254 oxidation reaction Methods 0.000 abstract description 7
239000003999 initiator Substances 0.000 abstract description 5
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
238000003756 stirring Methods 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 20
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
150000004763 sulfides Chemical class 0.000 description 16
238000001816 cooling Methods 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
125000001424 substituent group Chemical group 0.000 description 14
UKRQMDIFLKHCRO-UHFFFAOYSA-N 2,4,6-trimethylbenzoyl chloride Chemical compound CC1=CC(C)=C(C(Cl)=O)C(C)=C1 UKRQMDIFLKHCRO-UHFFFAOYSA-N 0.000 description 13
239000012300 argon atmosphere Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
229910000073 phosphorus hydride Inorganic materials 0.000 description 10
239000000047 product Substances 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000002390 rotary evaporation Methods 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 8
239000011521 glass Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000006277 sulfonation reaction Methods 0.000 description 8
238000001704 evaporation Methods 0.000 description 7
238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
239000007858 starting material Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
NDXRPDJVAUCBOH-UHFFFAOYSA-N 2,6-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(OC)=C1C(Cl)=O NDXRPDJVAUCBOH-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
SUEDCWGEKSLKOM-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-diphenylphosphorylmethanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SUEDCWGEKSLKOM-UHFFFAOYSA-N 0.000 description 3
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000001502 aryl halides Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
HXGDTGSAIMULJN-UHFFFAOYSA-N acenaphthylene Chemical compound C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
150000003003 phosphines Chemical class 0.000 description 2
238000006552 photochemical reaction Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
AJZYRHXRWZWBAH-UHFFFAOYSA-N 2,2-dichloroethylphosphane Chemical compound PCC(Cl)Cl AJZYRHXRWZWBAH-UHFFFAOYSA-N 0.000 description 1
JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 1
PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
WINBXTGLYQAOHN-UHFFFAOYSA-N CN(C)P(Cl)(Cl)(Cl)N(C)C Chemical compound CN(C)P(Cl)(Cl)(Cl)N(C)C WINBXTGLYQAOHN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000208202 Linaceae Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
HGBBFIVJLKAPGV-UHFFFAOYSA-N [(2,4-dipentoxyphenyl)-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CCCCCOC1=CC(OCCCCC)=CC=C1P(=O)(C(=O)C=1C(=CC(C)=CC=1C)C)C(=O)C1=C(C)C=C(C)C=C1C HGBBFIVJLKAPGV-UHFFFAOYSA-N 0.000 description 1
DNRISHWSPBDRTH-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-phenylphosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(Cl)C=CC=C1Cl DNRISHWSPBDRTH-UHFFFAOYSA-N 0.000 description 1
ZJWYMRUZYLNKIY-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4-dipentoxyphenyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound CCCCCOC1=CC(OCCCCC)=CC=C1P(=O)(C(=O)C=1C(=CC=CC=1OC)OC)C(=O)C1=C(OC)C=CC=C1OC ZJWYMRUZYLNKIY-UHFFFAOYSA-N 0.000 description 1
UXKGRRXMDPANPL-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-phenylphosphinothioyl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=S)(C=1C=CC=CC=1)C(=O)C1=C(OC)C=CC=C1OC UXKGRRXMDPANPL-UHFFFAOYSA-N 0.000 description 1
QISAYNXDUCNISJ-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-phenylphosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(OC)C=CC=C1OC QISAYNXDUCNISJ-UHFFFAOYSA-N 0.000 description 1
UZCSKSWDKYZTLJ-UHFFFAOYSA-N [ethyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC=1C=C(C)C=C(C)C=1C(=O)P(=O)(CC)C(=O)C1=C(C)C=C(C)C=C1C UZCSKSWDKYZTLJ-UHFFFAOYSA-N 0.000 description 1
YCWCHTSVGBYYIC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphinothioyl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=S)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C YCWCHTSVGBYYIC-UHFFFAOYSA-N 0.000 description 1
BUGGIVLTKSDWAW-UHFFFAOYSA-N [tert-butyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C(C)(C)C)C(=O)C1=C(C)C=C(C)C=C1C BUGGIVLTKSDWAW-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthalene Natural products C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000008378 aryl ethers Chemical class 0.000 description 1
150000004792 aryl magnesium halides Chemical class 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
HTJAVJQJNIBGMU-UHFFFAOYSA-N bis(2-methylphenyl)phosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C(=CC=CC=1)C)C1=CC=CC=C1C HTJAVJQJNIBGMU-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
CUIWZLHUNCCYBL-UHFFFAOYSA-N decacyclene Chemical compound C12=C([C]34)C=CC=C4C=CC=C3C2=C2C(=C34)C=C[CH]C4=CC=CC3=C2C2=C1C1=CC=CC3=CC=CC2=C31 CUIWZLHUNCCYBL-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000597 dioxinyl group Chemical group 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
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 description 1
VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical group C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
NMJASRUOIRRDSX-UHFFFAOYSA-N tert-butyl(dichloro)phosphane Chemical compound CC(C)(C)P(Cl)Cl NMJASRUOIRRDSX-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
125000005580 triphenylene group Chemical group 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- 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
- C07F9/5036—Phosphines containing the structure -C(=X)-P or NC-P
- 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
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)

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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK727-2001A 1998-11-30 1999-11-20 Spôsob prípravy acylfosfínov, acylfosfínoxidov a acylfosfínsulfidov SK286152B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH237698		1998-11-30
CH243498		1998-12-08
PCT/EP1999/008968 WO2000032612A1 (en)	1998-11-30	1999-11-20	Process for preparing acylphosphines and derivatives

Publications (2)

Publication Number	Publication Date
SK7272001A3 SK7272001A3 (en)	2001-12-03
SK286152B6 true SK286152B6 (sk)	2008-04-07

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ID=25690294

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SK727-2001A SK286152B6 (sk)	1998-11-30	1999-11-20	Spôsob prípravy acylfosfínov, acylfosfínoxidov a acylfosfínsulfidov

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Country	Link
US (3)	US6888031B1 (zh)
EP (1)	EP1135399B2 (zh)
JP (1)	JP4265871B2 (zh)
KR (1)	KR100653117B1 (zh)
CN (1)	CN1211388C (zh)
AT (1)	ATE221893T1 (zh)
AU (1)	AU760237B2 (zh)
CA (1)	CA2349637C (zh)
CZ (1)	CZ302512B6 (zh)
DE (1)	DE69902485T3 (zh)
ES (1)	ES2180347T5 (zh)
SK (1)	SK286152B6 (zh)
TW (1)	TW492972B (zh)
WO (1)	WO2000032612A1 (zh)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69902485T3 (de) *	1998-11-30	2007-03-15	Ciba Speciality Chemicals Holding Inc.	Verfahren zur herstellung von acylphosphinen und derivaten
GB2360283B (en) *	2000-02-08	2002-08-21	Ciba Sc Holding Ag	Monoacylarylphosphines and acylphosphine oxides and sulphides
GB2365430B (en) *	2000-06-08	2002-08-28	Ciba Sc Holding Ag	Acylphosphine photoinitiators and intermediates
EP1423757B1 (en) *	2001-08-21	2009-04-29	Ciba Holding Inc.	Bathochromic mono- and bis-acylphosphine oxides and sulfides and their use as photoinitiators
DE10206117A1 (de)	2002-02-13	2003-08-14	Basf Ag	Acyl- und Bisacylphosphinderivate
DE10244684A1 (de)	2002-09-24	2004-04-01	Basf Ag	Verfahren zur Herstellung von Acylphosphinoxiden
US7230137B2 (en) *	2002-12-04	2007-06-12	Ciba Specialty Chemicals Corp.	Process for the synthesis of cycloorganylphosphanes and di(alkyli metal/alkaline earth metal) oligophosphanediides
DE10315671A1 (de) *	2003-04-04	2004-10-14	Basf Ag	Verfahren zur Herstellung von Acylphosphinoxid-Feststoffen
AU2004262586A1 (en) *	2003-07-18	2005-02-17	Ciba Specialty Chemicals Holding Inc.	Process for preparing acylphosphanes and derivatives thereof
TW200523265A (en) *	2003-07-31	2005-07-16	Basf Ag	A process for the preparation of acylphosphines
US7687657B2 (en)	2004-11-23	2010-03-30	Ciba Speciality Chemicals Corporation	Process for preparing acylphosphanes and derivatives thereof
JP5234912B2 (ja) *	2005-01-17	2013-07-10	チバホールディングインコーポレーテッド	アシルホスファン、並びにこれらの酸化物及び硫化物の製造方法
DE102005005946A1 (de) *	2005-02-10	2006-08-17	Basf Ag	Verfahren zur Herstellung tertiärer Phosphine
KR101648996B1 (ko)	2008-11-03	2016-08-17	바스프 에스이	광개시제 혼합물
JP5951479B2 (ja) *	2009-04-20	2016-07-13	イーティーエイチ・チューリッヒ	ポリマーナノ粒子
CN102875598B (zh) *	2011-07-11	2016-09-07	深圳市有为化学技术有限公司	(二苯膦氧基)(均三甲苯基)甲酮和(苯膦氧基)双(均三甲苯基甲酮)的制备方法
CN102875597B (zh) *	2011-07-11	2017-05-03	深圳市有为化学技术有限公司	芳香酮膦氧杂化型化合物
CN102675365A (zh) *	2012-05-16	2012-09-19	湖北固润科技股份有限公司	一种紫外光引发剂xbpo合成方法
GB201213163D0 (en)	2012-07-24	2012-09-05	Lambson Ltd	Photopolymerisation processes and novel compounds therefor
ES2720760T3 (es)	2012-10-01	2019-07-24	Eth Zuerich	Un procedimiento para la preparación de acilofosfanos
WO2014140356A1 (en)	2013-03-15	2014-09-18	Freefly Systems Inc.	Method for enabling manual adjustment of a pointing direction of an actively stabilized camera
CN104592298B (zh) *	2014-12-31	2016-07-06	湖北固润科技股份有限公司	一种酰基膦高效光引发剂及其制备方法
CN105541913B (zh) *	2015-12-03	2017-08-25	天津久日新材料股份有限公司	一种2,4,6‑三甲基苯甲酰基二苯基氧化膦的制备方法
CN105732710A (zh) *	2016-03-16	2016-07-06	三峡大学	一种光引发剂联苯基四(2,4,6-三甲基苯甲酰基)氧化膦的制备方法及其应用
CN105732709A (zh) *	2016-03-16	2016-07-06	三峡大学	一种光引发剂2,4,6-三甲基苯甲酰二环己基氧膦，制备方法及其应用
CN107304220B (zh) *	2016-04-22	2020-03-31	江苏英力科技发展有限公司	一种“一锅法”合成2,4,6-三甲基苯甲酰基-二苯基氧化膦的方法
EP3296301A1 (en) *	2016-09-19	2018-03-21	ETH Zürich	A versatile process for the preparation of acylphosphines
JP6916484B2 (ja) *	2017-03-28	2021-08-11	国立大学法人千葉大学	アシルホスフィンの製造方法
EP3409680B1 (en)	2017-05-30	2021-01-06	IGM Group B.V.	Synthesis of bis(acyl)phosphines by activation of unreactive metal phosphides
EP3539924A1 (en) *	2018-03-14	2019-09-18	ETH Zurich	Novel vinyl phosphines and photo-initiators obtainable therefrom
CN110734461A (zh) *	2018-07-20	2020-01-31	深圳市有为化学技术有限公司	化合物2,4,6-三甲基苯甲酰基二苯基氧化膦的制备
EP3892625A4 (en) *	2018-12-07	2021-11-24	Anqing Lighting Optoelectronics Technology Co., Ltd	ACYLPHOSPHINE OXIDE COMPOUND AND RELATED PREPARATION PROCESS
CN111138491B (zh) *	2019-12-31	2022-08-05	天津久日新材料股份有限公司	一种制备光引发剂tpo同时副产氯苄的方法
CN111087425B (zh)	2020-01-10	2022-04-19	天津大学	一种大粒度苯基双(2,4,6-三甲基苯甲酰基)氧化膦晶型及其结晶方法
CN112279940B (zh) *	2020-04-17	2023-06-27	山东科技大学	一种酰基膦光引发剂及其制备方法
CN112159429B (zh) *	2020-10-29	2022-06-21	天津久日新材料股份有限公司	一种双(2,4,6-三甲基苯甲酰基)苯基氧化膦的制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0007086B1 (de)	1978-07-14	1982-02-10	BASF Aktiengesellschaft	Lichthärtbare Form-, Tränk- und Überzugsmassen sowie daraus hergestellte Formkörper
DE2909994A1 (de)	1979-03-14	1980-10-02	Basf Ag	Acylphosphinoxidverbindungen, ihre herstellung und verwendung
DE3020092A1 (de)	1980-05-27	1981-12-10	Basf Ag, 6700 Ludwigshafen	Acylphosphinverbindungen und ihre verwendung
DE3034697A1 (de)	1980-09-15	1982-05-06	Basf Ag, 6700 Ludwigshafen	Acylphosphinsulfidverbindungen, ihre herstellung und verwendung
DE3443221A1 (de)	1984-11-27	1986-06-05	ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld	Bisacylphosphinoxide, ihre herstellung und verwendung
US5218009A (en) *	1989-08-04	1993-06-08	Ciba-Geigy Corporation	Mono- and di-acylphosphine oxides
RU2091385C1 (ru)	1991-09-23	1997-09-27	Циба-Гейги АГ	Бисацилфосфиноксиды, состав и способ нанесения покрытий
ZA941879B (en)	1993-03-18	1994-09-19	Ciba Geigy	Curing compositions containing bisacylphosphine oxide photoinitiators
TW381106B (en) *	1994-09-02	2000-02-01	Ciba Sc Holding Ag	Alkoxyphenyl-substituted bisacylphosphine oxides
WO1996007662A1 (en) *	1994-09-08	1996-03-14	Ciba Specialty Chemicals Holding Inc.	Novel acylphosphine oxides
TW323274B (zh) *	1994-10-13	1997-12-21	Ciba Sc Holding Ag
DE69902485T3 (de) *	1998-11-30	2007-03-15	Ciba Speciality Chemicals Holding Inc.	Verfahren zur herstellung von acylphosphinen und derivaten
GB2360283B (en) *	2000-02-08	2002-08-21	Ciba Sc Holding Ag	Monoacylarylphosphines and acylphosphine oxides and sulphides

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US7094931B2 (en)	2006-08-22
CZ20011875A3 (cs)	2001-09-12
ES2180347T3 (es)	2003-02-01
TW492972B (en)	2002-07-01
KR20010093124A (ko)	2001-10-27
DE69902485T3 (de)	2007-03-15
JP2002531460A (ja)	2002-09-24
DE69902485T2 (de)	2003-05-08
ATE221893T1 (de)	2002-08-15
EP1135399B1 (en)	2002-08-07
CA2349637C (en)	2008-12-23
CN1211388C (zh)	2005-07-20
SK7272001A3 (en)	2001-12-03
US6888031B1 (en)	2005-05-03
EP1135399A1 (en)	2001-09-26
JP4265871B2 (ja)	2009-05-20
CN1328564A (zh)	2001-12-26
US20060128959A1 (en)	2006-06-15
CA2349637A1 (en)	2000-06-08
DE69902485D1 (de)	2002-09-12
US20040248855A1 (en)	2004-12-09
ES2180347T5 (es)	2007-04-01
AU1384500A (en)	2000-06-19
KR100653117B1 (ko)	2006-12-21
WO2000032612A1 (en)	2000-06-08
CZ302512B6 (cs)	2011-06-29
AU760237B2 (en)	2003-05-08
US7214830B2 (en)	2007-05-08
EP1135399B2 (en)	2006-08-09

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Publication	Publication Date	Title
SK286152B6 (sk)	2008-04-07	Spôsob prípravy acylfosfínov, acylfosfínoxidov a acylfosfínsulfidov
KR101083980B1 (ko)	2011-11-22	아실포스판 및 이의 유도체의 제조방법
EP1814891B1 (en)	2011-01-26	Bisacylphosphanes and their use as photoinitiators; process for preparing acylphosphanes
Pietrusiewicz et al.	1989	Optically active phosphine oxides. 8: Synthesis of nonsymmetrical 1, 2-diphosphinylethenes and related systems
US3004980A (en)	1961-10-17	Thiophosphoric acid esters
Toyota et al.	2001	Preparation and 31P NMR study of some low‐coordinated organophosphorus compounds bearing the 2, 4‐di‐t‐butyl‐6‐isopropylphenyl group
MXPA01005323A (en)	2002-02-26	Process for preparing acylphosphines and derivatives
US4670601A (en)	1987-06-02	Process for the preparation of bifunctional tertiary aromatic phosphine sulfides
US3156739A (en)	1964-11-10	Manufacture of olefins
US3270095A (en)	1966-08-30	Fluoro-chloro substituted phosphorus containing esters
CA2510473C (en)	2012-02-21	Process for the preparation of phosphitylation agents