JP6490717B2 - ジメチルアミノブタン、トリエチルアミン又はトリエタノールアミンを使用した有機モノホスファイトの塩素含有量の低減方法 - Google Patents
ジメチルアミノブタン、トリエチルアミン又はトリエタノールアミンを使用した有機モノホスファイトの塩素含有量の低減方法 Download PDFInfo
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- JP6490717B2 JP6490717B2 JP2016568535A JP2016568535A JP6490717B2 JP 6490717 B2 JP6490717 B2 JP 6490717B2 JP 2016568535 A JP2016568535 A JP 2016568535A JP 2016568535 A JP2016568535 A JP 2016568535A JP 6490717 B2 JP6490717 B2 JP 6490717B2
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- 238000000034 method Methods 0.000 title claims description 85
- 239000000460 chlorine Substances 0.000 title claims description 58
- 229910052801 chlorine Inorganic materials 0.000 title claims description 56
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 title claims description 52
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 title claims description 12
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 title claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 102
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 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 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 1
- -1 3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl Chemical group 0.000 description 57
- 239000007787 solid Substances 0.000 description 25
- 239000003446 ligand Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000011261 inert gas Substances 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 238000011049 filling Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 150000002903 organophosphorus compounds Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000007037 hydroformylation reaction Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- BBSPXGJFFPPTPZ-UHFFFAOYSA-N tert-butyl [2-tert-butyl-6-(3-tert-butyl-2-dichlorophosphanyloxy-5-methoxyphenyl)-4-methoxyphenyl] carbonate Chemical compound C(OC(C)(C)C)(OC1=C(C=C(C=C1C(C)(C)C)OC)C1=C(C(=CC(=C1)OC)C(C)(C)C)OP(Cl)Cl)=O BBSPXGJFFPPTPZ-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000004255 ion exchange chromatography Methods 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CWHIYHOQEQFVHN-UHFFFAOYSA-N tert-butyl [2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)-4-methoxyphenyl] carbonate Chemical compound C(OC(C)(C)C)(OC1=C(C=C(C=C1C(C)(C)C)OC)C1=C(C(=CC(=C1)OC)C(C)(C)C)O)=O CWHIYHOQEQFVHN-UHFFFAOYSA-N 0.000 description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- 125000006707 (C3-C12) heterocycloalkyl group Chemical group 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- JJNVYXHIEDMRIX-UHFFFAOYSA-N 3,3-ditert-butyl-2-(2-hydroxyphenyl)-5,5-dimethoxycyclohexen-1-ol Chemical compound C(C)(C)(C)C1(C(=C(CC(C1)(OC)OC)O)C=1C(=CC=CC1)O)C(C)(C)C JJNVYXHIEDMRIX-UHFFFAOYSA-N 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 1
- CMZYGFLOKOQMKF-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-3,5-dimethylbenzene Chemical group CC1=CC(C)=CC(C=2C=C(C)C=C(C)C=2)=C1 CMZYGFLOKOQMKF-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ZZZRZBIPCKQDQR-UHFFFAOYSA-N 2,4-ditert-butyl-6-methylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O ZZZRZBIPCKQDQR-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- XBDTZNMRTRPDKH-UHFFFAOYSA-N 2-(2-hydroxy-3,5-dimethylphenyl)-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(C=2C(=C(C)C=C(C)C=2)O)=C1 XBDTZNMRTRPDKH-UHFFFAOYSA-N 0.000 description 1
- IZUHTIIVAKICLD-UHFFFAOYSA-N 2-(2-hydroxyphenyl)phenol pyridine Chemical compound C=1(C(=CC=CC1)C=1C(=CC=CC1)O)O.N1=CC=CC=C1 IZUHTIIVAKICLD-UHFFFAOYSA-N 0.000 description 1
- CBYWHFTZNVZQHV-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)-4-methoxyphenol Chemical compound CC(C)(C)C1=CC(OC)=CC(C=2C(=C(C=C(OC)C=2)C(C)(C)C)O)=C1O CBYWHFTZNVZQHV-UHFFFAOYSA-N 0.000 description 1
- GXGUNEKFCHJBLU-UHFFFAOYSA-N 3,5-ditert-butyl-2-(2,4-ditert-butyl-6-hydroxyphenyl)phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(O)=C1C1=C(O)C=C(C(C)(C)C)C=C1C(C)(C)C GXGUNEKFCHJBLU-UHFFFAOYSA-N 0.000 description 1
- MIHQWNKDHBLQEZ-UHFFFAOYSA-N 3-tert-butyl-2-methylphenol Chemical compound CC1=C(O)C=CC=C1C(C)(C)C MIHQWNKDHBLQEZ-UHFFFAOYSA-N 0.000 description 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
- AESQDCMZHBUWPN-UHFFFAOYSA-N 4h-1,3,2-dioxaphosphinine Chemical compound C1OPOC=C1 AESQDCMZHBUWPN-UHFFFAOYSA-N 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- SVNCDHBIQPXHHA-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphate Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(=O)(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C SVNCDHBIQPXHHA-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 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
- 239000002274 desiccant Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- NPXUKNQBFIIIDW-UHFFFAOYSA-N dichlorophosphinite Chemical compound [O-]P(Cl)Cl NPXUKNQBFIIIDW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 239000003344 environmental pollutant Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
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- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003041 laboratory chemical Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
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- 231100000719 pollutant Toxicity 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
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- 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
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- PQXSRBUXVJIPDU-UHFFFAOYSA-N toluene;trichlorophosphane Chemical compound ClP(Cl)Cl.CC1=CC=CC=C1 PQXSRBUXVJIPDU-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/062—Organo-phosphoranes without P-C bonds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- 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
- C07F9/6571—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 and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
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- C—CHEMISTRY; METALLURGY
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- 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 System
- C07F9/02—Phosphorus compounds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
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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 System
- 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
- C07F9/6571—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 and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
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- 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 System
- 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
- C07F9/6571—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 and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65748—Esters of oxyacids of phosphorus the cyclic phosphorus atom belonging to more than one ring system
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- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
ヒドロホルミル化において、これらの化合物は、顕著な役割を果たす(R.Franke,D.Selent,A.Borner:Applied Hydroformylation.Chem.Rev.,2012,DOI:10.1021/cr3001803)。
及びR10は、−(C1−C12)アルキルである。
及びTは、−CH3、−CF3、−CH2C6H5から選択され、
及びQは、−(C1−C12)−アルキル、−C(CH3)3から選択され、
及びVは、−CH2CH2COCH3、−C(CH3)3、−C6H5から選択され、
及びWは、−Me、−CH2CH3、−CH2CH2CH3、−CH2−シクロ−C3H5、−CH(CH3)2、−シクロ−C6H11、−C(CH3)3、−CH2C6H5、−CH2C6H3−2,4−(CH3)2から選択され、
及びX及びYはそれぞれ独立して、−(C1−C12)−アルキル、−(C6−C20)−アリール、−(C6−C20)−アリール−(C1−C12)−アルキル、−(C1−C12)−アルキル−O−(C6−C20)−アリールから選択される。
及びZは、−(C1−C12)−アルキル−、−(C6−C20)−アリール−、−(C6−C20)−アリール−(C6−C20)−アリール−から選択され、
ならびに記載のアルキル、シクロアルキル及びアリール基は、置換されてもよく、
該方法は、
a)芳香族化合物、アルコール類、アセトン、酢酸エチル、アセトニトリル、エーテル、水から選択される第1の溶媒を含む第1の溶液中に、部分的にまたは完全に有機モノホスファイトを溶解する工程であって、
ここでの該第1の溶液がジメチルアミノブタン又はトリエチルアミン又はトリエタノールアミンを含む工程と、
c)精製された有機モノホスファイトを沈殿させる工程とを含む。
b)芳香族化合物、C5−C10−アルカン、アルコール類、アセトン、酢酸エチル、アセトニトリル、エーテル、水から選択される第2の溶媒を含む第2の溶液に第1の溶液を導入する工程を含む。
本方法の一変形例では、有機モノホスファイトは、一般式I、II、III及びIV:
及びWは−CH3であり、
及びQは−C(CH3)3である。
本方法の一変形例では、Zは以下である。
本発明に関連して報告する総塩素含有量は、Wickbold法:DIN51408に準拠したサンプル調製及びDIN EN ISO10304に準拠したイオンクロマトグラフィーによる測定値によって判定される。
反応スキーム:
tert−ブチル(3,3’−ジ−tert−ブチル−2’−ヒドロキシ−5,5’−ジメトキシ−[1,1’−ビフェニル]−2−イル)カーボネートの三塩化リンとの反応:
tert−ブチル(3,3’−ジ−tert−ブチル−2’−((ジクロロホスフィノ)オキシ)−5,5’−ジメトキシ−[1,1’−ビフェニル]−2−イル)カーボネートの3,3’,5,5’−テトラメチル−(1,1’−ビフェニル)−2,2’−ジオールとの反応
tert−ブチル(3,3’−ジ−tert−ブチル−2’−ヒドロキシ−5,5’−ジメトキシ−[1,1’−ビフェニル]−2−イル)カーボネートの2−クロロ−4,4,5,5−テトラフェニル−1,3,2−ジオキサホスホランとの反応
tert−ブチル(3,3’−ジ−tert−ブチル−2’−((ジクロロホスフィノ)オキシ)−5,5’−ジメトキシ−[1,1’−ビフェニル]−2−イル)カーボネートの2,2’−ビフェノールとの反応
tert−ブチル(3,3’−ジ−tert−ブチル−2’−((ジクロロホスフィノ)オキシ)−5,5’−ジメトキシ−[1,1’−ビフェニル]−2−イル)カーボネートの3,3,5,5−テトラ−tert−ブチルビフェノールとの反応
tert−ブチル(3,3’−ジ−tert−ブチル−2’−((ジクロロホスフィノ)オキシ)−5,5’−ジメトキシ−[1,1’−ビフェニル]−2−イル)カーボネートの3,3−ジ−tert−ブチル−5,5−ジメトキシビフェノールとの反応
tert−ブチル(3,3’−ジ−tert−ブチル−2’−((ジクロロホスフィノ)オキシ)−5,5’−ジメトキシ−[1,1’−ビフェニル]−2−イル)カーボネートの2,4−ジメチルフェノールとの反応
塩素の減量
実施例8:(XI)の塩素還元
a)トルエン−DMAB/アセトニトリル−DMAB
二重のWickbold法による塩素決定の結果:65/65mg/kg(ppm)
b)トルエン−DMAB/アセトニトリル
二重のWickbold法による塩素決定の結果:75/80mg/kg(ppm)
排気と不活性ガスの充填を繰り返した 2Lのシュレンクフラスコ中で、当初1.1重量%の塩素濃度を有する189.6gの粗配位子(XI)を760mLの脱気したトルエン及び165mLのN,N’−ジメチルアミノブタン中で撹拌しながら105℃まで加熱した。撹拌中の約10分間、この温度を維持した。
Wickbold法による塩素結果:<10mg/kg(ppm)
排気と不活性ガスの充填を繰り返した 100mLのシュレンクフラスコ中で、当初1.1重量%の塩素濃度を有する10.06gの(XI)を計量し、45mLの脱気したトルエンと混合した。この懸濁液を102℃まで加熱し、撹拌しながら20分間放置した。この過程で主要な留分は溶解した。ごく少量の粒子だけが溶け残った。その後、わずかに濁った溶液に加熱濾過を施し、透明な濾過物を室温で減圧下にて乾燥状態まで濃縮した。
Wickbold法による塩素結果:120mg/kg(ppm)
a)0℃の脱気したエタノール+1%の脱気した水+5%の脱気したDMABを使用した精製作業
精製作業のため、最初に、300mLの脱気したエタノール及び15mLの脱気したN,N’−ジメチルアミノブタンを当初1.3%の塩素濃度を有する粗配位子(XV)に撹拌しながら添加して、混合物を2時間撹拌した。その後、3mLの脱気したDI水を添加して、混合物を0℃まで冷却し、2時間撹拌した。次に、固体を濾過によって分離し、40mLの脱気した冷エタノールで2回洗浄して乾燥させた。
二重のWickbold法による塩素決定の結果:20/20mg/kg(ppm)
収量:68.9%に相当する68.01g。
b)水/アセトニトリル/N,N’−ジメチルアミノブタン(10:10:1)を使用した精製作業
更なる精製作業のため、当初1.3重量%の塩素濃度を有する粗配位子(XV)を40mLの脱気したACN及び4mLの脱気したN,N’−ジメチルアミノブタン(5%)に撹拌しながら溶解させた。その後室温にて一晩撹拌した。最初の沈殿は、約1時間後に観察された。翌朝、40mLの脱気したDI水を混合物に添加した。混合物を30分間撹拌した。次に、この固体を濾過によって分離し、少し脱気した水で洗浄し乾燥させた。
二重のWickbold法による塩素決定の結果:50/55mg/kg(ppm)
収量:64.02%に相当する16.6g。
DMAB:ジメチルアミノブタン
Claims (12)
- 一般式I、II、III及びIVのうち1つの有機モノホスファイト中の塩素含有量を低減する方法であって、
及びQは、−(C1−C12)−アルキル、−C(CH3)3から選択され、
及びWは、−Me、−CH2CH3、−CH2CH2CH3、−CH2−シクロ−C3H5、−CH(CH3)2、−シクロ−C6H11、−C(CH3)3、−CH2C6H5、−CH2C6H3−2,4−(CH3)2から選択され、
及びX及びYはそれぞれ独立して、−(C1−C12)−アルキル、−(C6−C20)−アリール、−(C6−C20)−アリール−(C1−C12)−アルキル、−(C1−C12)−アルキル−(C6−C20)−アリールから選択され、
及びZは、−(C1−C12)−アルキル−、−(C6−C20)−アリール−、−(C6−C20)−アリール−(C6−C20)−アリールから選択され、
ならびに記載のアルキル、シクロアルキル及びアリール基は、置換されてもよく、
該方法は、
a)芳香族化合物、アルコール類、アセトン、酢酸エチル、アセトニトリル、エーテル、水から選択される第1の溶媒を含む第1の溶液中に、部分的にまたは完全に有機モノホスファイトを溶解する工程であって、
ここで前記第1の溶液はジメチルアミノブタン又はトリエチルアミン又はトリエタノールアミンを含む工程と、
b)芳香族化合物、C 5 −C 10 −アルカン、アルコール類、アセトン、酢酸エチル、アセトニトリル、エーテル、水から選択される第2の溶媒を含む第2の溶液に、前記a)工程で得られた部分的にまたは完全に有機モノホスファイトを溶解した溶液を導入する工程と、
c)精製された有機モノホスファイトを沈殿させる工程とを含む、方法。 - 前記第1の溶液はジメチルアミノブタンを含む、請求項1に記載の方法。
- 前記第1の溶媒は酢酸エチル、アニソール、オルト−キシレン、トルエン、アセトン、メタノール、エタノール、プロパノール、イソプロパノール、アセトニトリル、水から選択される、請求項1又は2に記載の方法。
- 前記第1の溶媒はトルエンである、請求項1〜3のいずれか一項に記載の方法。
- 前記第2の溶媒は酢酸エチル、アニソール、オルト−キシレン、トルエン、アセトン、メタノール、エタノール、プロパノール、イソプロパノール、アセトニトリル、テトラヒドロフラン、ジエチルエーテル、グリコール、C5−C10−アルカン、水から選択される、請求項1〜4のいずれか一項に記載の方法。
- 前記第2の溶媒はアセトニトリルである、請求項1〜5のいずれか一項に記載の方法。
- 前記第2の溶液はジメチルアミノブタン又はトリエチルアミンを含む、請求項1〜6のいずれか一項に記載の方法。
- 前記有機モノホスファイトはプロセス工程a)において前記第1の溶液に完全に溶解される、請求項1〜7のいずれか一項に記載の方法。
- 前記精製された有機モノホスファイトは<200ppmの塩素含有量を有する、請求項1〜8のいずれか一項に記載の方法。
- 前記プロセス工程a)で得られた溶液がプロセス工程b)において前記第2の溶液に導入される前に、前記第2の溶液を−10℃〜80℃の範囲の温度にする、請求項1〜9のいずれか一項に記載の方法。
- 式中、
R1、R2、R3、R4、R5、R6、R7、及びR8はそれぞれ独立して、−H、−(C1−C12)−アルキル、−O−(C1−C12)−アルキル、−O−(C6−C20)−アリール、−(C6−C20)−アリールから選択され、
及びWは−CH3であり、
及びQは−C(CH3)3である、請求項1〜10のいずれか一項に記載の方法。 - 式中、Zは次式であり、
式中、R11、R12、R13、R14、R15、R16、R17、R18はそれぞれ独立して、−H、−(C1−C12)−アルキル、−O−(C1−C12)−アルキル、−O−(C6−C20)−アリール、−(C6−C20)−アリール、−ハロゲン、−COO−(C1−C12)−アルキル、−CONH−(C1−C12)−アルキル、−(C6−C20)−アリール−CON[(C1−C12)−アルキル]2、−CO−(C1−C12)−アルキル、−CO−(C6−C20)−アリール、−COOH、−OH、−SO3H、−SO3Na、−NO2、−CN、−NH2、−N[(C1−C12)−アルキル]2から選択される、請求項1〜11のいずれか一項に記載の方法。
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DE102014209533.6A DE102014209533A1 (de) | 2014-05-20 | 2014-05-20 | Gemische von Monophosphitligand und deren Verwendung zur Katalyse einer Hydroformylierungsreaktion |
DE102014209536.0A DE102014209536A1 (de) | 2014-05-20 | 2014-05-20 | Herstellung qualitativ hochwertiger Oxo-Alkohole aus unsteten Rohstoffquellen |
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DE102014209534.4A DE102014209534A1 (de) | 2014-05-20 | 2014-05-20 | Neue Monophosphitliganden mit einer Carbonat-Gruppe |
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DE102015202722.8A DE102015202722A1 (de) | 2014-05-20 | 2015-02-16 | Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Monophosphit-Gemischen |
PCT/EP2015/059290 WO2015176929A1 (de) | 2014-05-20 | 2015-04-29 | Verfahren zur reduzierung des chlorgehalts von organomonophosphiten unter verwendung von dimethylaminobutan, triethylamin oder triethanolamin |
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US (2) | US9751904B2 (ja) |
EP (3) | EP3145940B1 (ja) |
JP (1) | JP6490717B2 (ja) |
KR (1) | KR101898369B1 (ja) |
CN (1) | CN106414467A (ja) |
ES (3) | ES2724352T3 (ja) |
PL (1) | PL3145940T4 (ja) |
SG (1) | SG11201609677WA (ja) |
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DE102014201756A1 (de) | 2014-01-31 | 2015-08-06 | Evonik Degussa Gmbh | Reinigung chlorverschmutzter Organophosphorverbindungen |
DE102014202500A1 (de) | 2014-02-12 | 2015-08-13 | Evonik Degussa Gmbh | Verfahren zur Reduzierung des Chlorgehalts von Organobisphosphiten |
EP3029013B1 (de) * | 2014-12-04 | 2018-06-13 | Evonik Degussa GmbH | Monophosphite mit Struktureinheit 4,4,5,5-Tetraphenyl-1,3,2-dioxaphospholan als Liganden für Hydroformylierungskatalysatoren |
DE102015207864A1 (de) | 2015-04-29 | 2016-11-03 | Evonik Degussa Gmbh | Neue Monophosphitverbindungen mit einer Ethergruppe |
DE102015207860A1 (de) | 2015-04-29 | 2016-11-03 | Evonik Degussa Gmbh | Neue Monophosphitverbindungen mit einer Methylgruppe |
EP3147291A1 (de) | 2015-09-28 | 2017-03-29 | Evonik Degussa GmbH | Verfahren zur reduzierung des chlorgehalts von organotetraphosphiten |
EP3176174A1 (de) * | 2015-12-03 | 2017-06-07 | Evonik Degussa GmbH | Verfahren zur reduzierung des chlorgehalts von organotetraphosphiten |
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FR2259104B1 (ja) * | 1974-01-25 | 1976-11-26 | Rhone Poulenc Ind | |
US4835299A (en) | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
EP0592364B1 (de) * | 1992-10-05 | 2001-07-11 | Ciba SC Holding AG | Verfahren zur Stabilisierung dreiwertiger Phosphorverbindungen mit Aminen |
US5440067A (en) | 1994-11-18 | 1995-08-08 | E. I. Dupont De Nemours And Company | Catalyzed gas phase isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
US5449807A (en) | 1994-11-18 | 1995-09-12 | E. I. Du Pont De Nemours And Company | Catalyzed vapor phase hydrocyanation of diolefinic compounds |
US5962744A (en) | 1998-03-27 | 1999-10-05 | The Research Foundation Of State University Of New York | Process for hydrocarbonylations in supercritical carbon dioxide |
DE19853748A1 (de) * | 1998-11-21 | 2000-05-25 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellungh chiraler Aldehyde |
US6380421B1 (en) * | 1999-09-20 | 2002-04-30 | E. I. Du Pont De Nemours And Company | Multidentate phosphite ligands, catalytic compositions containing such ligands and catalytic processes utilizing such catalytic compositions |
DE19953058A1 (de) | 1999-11-03 | 2001-05-10 | Basf Ag | Phosphite |
DE102004049339A1 (de) | 2004-10-08 | 2006-04-13 | Basf Ag | Verfahren zur Reinigung von phosphorhaltigen Chelat-Liganden |
GB0519651D0 (en) | 2005-09-27 | 2005-11-02 | Univ Nottingham | Ferrocenyl phosphite ligands for asymmetric catalysis and a method for their production |
DE102006058682A1 (de) | 2006-12-13 | 2008-06-19 | Evonik Oxeno Gmbh | Bisphosphitliganden für die übergangsmetallkatalysierte Hydroformylierung |
DE102008043584A1 (de) | 2008-11-07 | 2010-05-12 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 6-Chlorodibenzo(d,f) (1,3,2)-dioxaphosphepin |
DE102011002640B4 (de) | 2011-01-13 | 2021-10-07 | Evonik Operations Gmbh | Verfahren zur Aufreinigung von Biphephos |
DE102011085883A1 (de) * | 2011-11-08 | 2013-05-08 | Evonik Oxeno Gmbh | Neue Organophosphorverbindungen auf Basis von Anthracentriol |
US9108988B2 (en) * | 2011-12-30 | 2015-08-18 | Basf Se | Method of purifying organic diphosphite compounds |
KR101645351B1 (ko) | 2011-12-30 | 2016-08-03 | 바스프 에스이 | 유기 디포스파이트 화합물의 정제 방법 |
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EP3145941A1 (de) | 2017-03-29 |
ES2772074T3 (es) | 2020-07-07 |
US20170088570A1 (en) | 2017-03-30 |
KR101898369B1 (ko) | 2018-09-12 |
TW201607953A (zh) | 2016-03-01 |
ES2715677T3 (es) | 2019-06-05 |
US9840524B2 (en) | 2017-12-12 |
WO2015176929A1 (de) | 2015-11-26 |
EP3145940A1 (de) | 2017-03-29 |
TW201602126A (zh) | 2016-01-16 |
SG11201609677WA (en) | 2016-12-29 |
EP3145938B1 (de) | 2018-12-26 |
KR20170007428A (ko) | 2017-01-18 |
US9751904B2 (en) | 2017-09-05 |
PL3145940T3 (pl) | 2019-05-31 |
EP3145938A1 (de) | 2017-03-29 |
ES2724352T3 (es) | 2019-09-10 |
PL3145940T4 (pl) | 2019-05-31 |
CN106414467A (zh) | 2017-02-15 |
TW201609778A (zh) | 2016-03-16 |
US20170121355A1 (en) | 2017-05-04 |
WO2015176927A1 (de) | 2015-11-26 |
EP3145940B1 (de) | 2018-12-12 |
WO2015176928A1 (de) | 2015-11-26 |
EP3145941B1 (de) | 2019-12-18 |
JP2017515874A (ja) | 2017-06-15 |
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