WO2003045919A2 - Process for the synthesis of amine ethers from secondary amino oxides and uses - Google Patents
Process for the synthesis of amine ethers from secondary amino oxides and uses Download PDFInfo
- Publication number
- WO2003045919A2 WO2003045919A2 PCT/EP2002/012957 EP0212957W WO03045919A2 WO 2003045919 A2 WO2003045919 A2 WO 2003045919A2 EP 0212957 W EP0212957 W EP 0212957W WO 03045919 A2 WO03045919 A2 WO 03045919A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- carbon atoms
- substituted
- phenyl
- hydrogen
- Prior art date
Links
- -1 amine ethers Chemical class 0.000 title claims abstract description 136
- 238000000034 method Methods 0.000 title claims abstract description 46
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 36
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 32
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 29
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 18
- 239000011368 organic material Substances 0.000 claims abstract description 4
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- 239000002243 precursor Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 158
- 229910052739 hydrogen Inorganic materials 0.000 claims description 102
- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical group 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 150000004694 iodide salts Chemical class 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 125000005466 alkylenyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000004305 biphenyl Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000006193 alkinyl group Chemical group 0.000 claims description 4
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical class [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 claims description 3
- 229910001867 inorganic solvent Inorganic materials 0.000 claims description 3
- 239000003049 inorganic solvent Substances 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical class [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 150000002431 hydrogen Chemical class 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 23
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 22
- 239000012258 stirred mixture Substances 0.000 description 21
- 239000008346 aqueous phase Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 18
- 230000008034 disappearance Effects 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 229940093499 ethyl acetate Drugs 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- 150000001721 carbon Chemical group 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 229910002651 NO3 Inorganic materials 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000019502 Orange oil Nutrition 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000010502 orange oil Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- 0 *C(*(C(*N1)(N)N)ON)(C1=O)N Chemical compound *C(*(C(*N1)(N)N)ON)(C1=O)N 0.000 description 4
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 description 4
- AQKZSTFCPAOFIV-UHFFFAOYSA-N 2-[(4-ethylphenoxy)methyl]oxirane Chemical compound C1=CC(CC)=CC=C1OCC1OC1 AQKZSTFCPAOFIV-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ITSBEHFZMYOGTA-UHFFFAOYSA-N 8,10-diethyl-9-hydroxy-3,3,8,10,11-pentamethyl-1,5-dioxa-9-azaspiro[5.5]undecane Chemical compound CC1C(C)(CC)N(O)C(CC)(C)CC11OCC(C)(C)CO1 ITSBEHFZMYOGTA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 125000001436 propyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- TYQJCMXOYINYLF-UHFFFAOYSA-N 9-hydroxy-3,3,8,8,10,10-hexamethyl-1,5-dioxa-9-azaspiro[5.5]undecane Chemical compound O1CC(C)(C)COC11CC(C)(C)N(O)C(C)(C)C1 TYQJCMXOYINYLF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical class CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
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- BUZHLYBJNNZTPL-UHFFFAOYSA-N pentane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CC(C(O)=O)CC(O)=O BUZHLYBJNNZTPL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- OBMLOTDECOTAGU-UHFFFAOYSA-M tetradodecylazanium;iodide Chemical compound [I-].CCCCCCCCCCCC[N+](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC OBMLOTDECOTAGU-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- WKSYTZHMRBAPAO-UHFFFAOYSA-M tetraethylphosphanium;iodide Chemical compound [I-].CC[P+](CC)(CC)CC WKSYTZHMRBAPAO-UHFFFAOYSA-M 0.000 description 1
- RLKUIQAEJXADLH-UHFFFAOYSA-M tetrahexadecylazanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[N+](CCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC RLKUIQAEJXADLH-UHFFFAOYSA-M 0.000 description 1
- VRKHAMWCGMJAMI-UHFFFAOYSA-M tetrahexylazanium;iodide Chemical compound [I-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC VRKHAMWCGMJAMI-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- KGPZZJZTFHCXNK-UHFFFAOYSA-M tetraoctylazanium;iodide Chemical compound [I-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC KGPZZJZTFHCXNK-UHFFFAOYSA-M 0.000 description 1
- JTFPRVNRGNKAAV-UHFFFAOYSA-M tetraoctylphosphanium;iodide Chemical compound [I-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC JTFPRVNRGNKAAV-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- KZLXBZDNRACERI-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC KZLXBZDNRACERI-UHFFFAOYSA-M 0.000 description 1
- RRIQOXRRSJKRFR-UHFFFAOYSA-M trimethyl(octyl)azanium;iodide Chemical compound [I-].CCCCCCCC[N+](C)(C)C RRIQOXRRSJKRFR-UHFFFAOYSA-M 0.000 description 1
- XQLLUORERPKHEM-UHFFFAOYSA-M trimethyl(phenyl)phosphanium;iodide Chemical compound [I-].C[P+](C)(C)C1=CC=CC=C1 XQLLUORERPKHEM-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RGBJYTMHKCMMOJ-UHFFFAOYSA-M trioctyl(propyl)azanium;iodide Chemical compound [I-].CCCCCCCC[N+](CCC)(CCCCCCCC)CCCCCCCC RGBJYTMHKCMMOJ-UHFFFAOYSA-M 0.000 description 1
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
- IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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
- 125000002948 undecyl group Chemical class [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
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
Definitions
- the instant invention pertains to a process for preparing amine ethers, e.g. N-hydro- carbyloxy substituted hindered amine compounds, by the reaction of the corresponding N- oxyl intermediate with a hydrocarbon in presence of an organic hydroperoxide and an iodide catalyst.
- amine ethers e.g. N-hydro- carbyloxy substituted hindered amine compounds
- Unites States Patent No 5,374,729 describes a process for the preparation of N- methoxy derivatives of hindered amines from the reaction of the corresponding N-oxyl compound with methyl radicals produced from dimethyl sulfoxide by decomposing aqueous hydrogen peroxide in presence of a metal salt or by thermal decomposition of di-tert.butyl peroxide.
- the aliphatic hydrocarbon compound may be any compound selected from alkane, alkene, alkyne, or cyclic or polycyclic analogues thereof, and optionally may be substituted, e.g. by aryl, halogen, alkoxy etc., provided that an aliphatic CH (or CH 2 , CH 3 ) moiety is contained.
- E' is C1-C36 alkyl; C3-C1 Q alkenyl; C2-C18 alkinyl; C5-C18 cycloalkyl; C5-C18 cycloalkenyl; a radical of a saturated or unsaturated aliphatic bicyclic or tricyclic hydrocarbon of 7 to 12 carbon atoms; C2-C7alkyl or C ⁇ -Cyalkenyl substituted by halogen, CrC 8 alkoxy or phenoxy; C 4 -C 12 heterocycloalkyl; C -C 12 heterocycloalkenyl; C7-C15 aralkyl or-C 4 -C 12 heteroaralkyl, each of which is unsubstituted or substituted by C1-C4 alkyl or phenyl; or E' is a radical of formula (VII) or (VIII)
- T' is tertiary C 4 -C ⁇ 8 alkyl or phenyl, each of which are unsubstituted or substituted by halogen,
- R 2 5 s OH, C C ⁇ 8 alkoxy, benzyloxy, N(R 18 ) 2 ; which process comprises reacting a N-oxyl hindered amine of formula III or Ilia
- cycloalkyl examples include cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, dimethylcyclopentyl and methylcyclohexyl.
- Gi and G 2 and/or G 3 and G forming, together with the linking carbon atom, a C 3 - C 12 cycloalkyl radical, preferably form a C 5 -C 12 cycloalkyl radical, especially cyclopentylene, cyclohexylene or cycloheptylene.
- Z is O or NR 8 ;
- Rg, R ⁇ o > R11, i2 > R 1 3 and R 14 are independently hydrogen, phenyl, or C ⁇ -C ⁇ 8 alkyl;
- the sterically hindered aminoxides also referred to as N-oxyl educts for the instant process which include compounds of formulae B, III or Ilia, are largely known in thaart; they may be prepared by oxidation of the corresponding N-H hindered amine with a suitable oxygen donor, e.g. by the reaction of the corresponding N-H hindered amine with hydrogen peroxide and sodium tungstate as described by E. G. Rozantsev et al., in Synthesis, 1971 , 192; or with tert-butyl hydroperoxide and molybdenum (VI) as taught in United States Patent No. 4,691 ,015, or obtained in analogous manner.
- a suitable oxygen donor e.g. by the reaction of the corresponding N-H hindered amine with hydrogen peroxide and sodium tungstate as described by E. G. Rozantsev et al., in Synthesis, 1971 , 192; or with tert-butyl
- the preferred amount of hydrocarbon for the instant process depends to some extent on the relative number of reactive hydrogens on the hydrocarbon reactant and the hindered amine nitroxyl compound.
- the reaction is typically carried out with a ratio of 1 to 100 moles of hydrocarbon per mole of nitroxyl moiety with the preferred ratio being 1 to 50 moles per mole of nitroxyl moiety, and the most preferred ratio being 1 to 30 moles of hydrocarbon per mole of nitroxyl moiety.
- the organic hydroperoxide used in the process of present invention can be of the formula R-OOH, wherein R usually is a hydrocarbon containing 1-18 carbon atoms.
- the organic hydroperoxide preferably is a peroxoalcohol containing 3-18 carbon atoms.
- R is often aliphatic, preferably C C ⁇ 2 alkyl.
- Most preferred organic hydroperoxide is tert.butyl hydroperoxide.
- the reaction is preferably run at 0° to 100°C; more preferably at 20° to 100°C, especially in the range 20-80°C.
- Ar is C 6 -C 0 aryl or C 5 -C 9 heteroaryl
- G 55 is H, CH 3 or phenyl
- G 6 6 is -CN or a group of the formula -COOR 4 or -CH 2 -O-G 4 ;
- L is a carbon centered radical formed from propane, butane, pentane, 2,2-dimethyl-propane, xylene.
- a solvent may be used, especially if the hydrocarbon, such as the compound of of formula IV or V, is a solid at the temperature of the reaction or if the catalyst is not very soluble in the hydrocarbon.
- Inert solvents should have less active carbon-hydrogen bonds; typical inert solvents are acetonitrile, aromatic hydrocarbons like benzene, chlorobenzene, CCI 4 , alcohols (e.g. methanol, ethanol, ethylene glycol, ethylene glycol monomethyl ether), or, especially for reactions with activated hydrocarbons like alkylated aromats or alkenes, also alkanes like hexane, decane etc., or mixtures thereof.
- Inorganic solvents such as water are possible as well.
- the reaction can be carried out in one liquid phase or in separate phases.
- the iodide catalyst may be selected from any iodide compound, including organic and inorganic iodide compounds. Examples are alkaline or alkaline earth metal iodides, or onium iodides such as ammonium or phosphonium or sulfonium iodides. Suitable metal iodides are, inter alia, those of lithium, sodium, potassium, magnesium or calcium.
- onium iodides which are soluble in organic solvents.
- Suitable onium iodides embrace quaternary ammonium , phosphonium or sulfonium iodides.
- the structure of the onium cation is less important provided the solubility in organic solvents is high enough; the latter can be increased by increasing the hydrophobicity of the hydrocarbon residues attached to the onium cation.
- Some readily available materials are tetra-CrC 12 alkylated ammonium iodides and/or the following compounds:
- the onium iodides can be bound to an organic or inorganic polymer backbone, rendering a homogeneous or heterogenous catalytic system.
- the instant process can be run in air or in an inert atmosphere such a nitrogen or argon.
- the instant process can be run under atmospheric pressure as well as under reduced or elevated pressure. Elevated pressure can especially be useful in reactions with a hydrocarbon, which is gaseous under atmospheric pressure and the reaction temperature; in this case, pressure/temperature conditions are advantageous where the hydrocarbon forms a liquid phase or is at least partially dissolved in a suitable solvent.
- a second variation of the instant process is to simultaneously add separate solutions of the hydroperoxide and the nitroxyl compound to a mixture of the hydrocarbon, cosolvent (if used) and catalyst.
- the nitroxyl compound may be dissolved in water or the alcohol solvent used in the reaction. Some of the nitroxyl compound may be introduced into the reaction mixture prior to starting the peroxide addition, and all of the nitroxyl compound should be added prior to completing the peroxide addition.
- R 2 is hydrogen, alkyl of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms; n is 1 to 4;
- R 3 is alkyl of 1 to 18 carbon atoms, alkoxycarbonylalkylenecarbonyl of 4 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, glycidyl, 2,3-dihydroxypropyl, 2-hydroxy or 2- (hydroxymethyl) substituted alkyl of 3 to 12 carbon atoms which alkyl is interrupted by oxygen, an acyl radical of an aliphatic or unsaturated aliphatic carboxylic or carbamic acid containing 2 to 18 carbon atoms, an acyl radical of a cycloaliphatic carboxylic or carbamic acid containing 7 to 12 carbon atoms, or acyl radical of an aromatic acid containing 7 to 15 carbon atoms;
- p 1 to 3
- R is hydrogen, alkyl of 1 to 18 carbon atoms or acyl of 2 to 6 carbon atoms
- R 5 is hydrogen, alkyl of 1 to 18 carbon atoms, an acyl radical of an aliphatic or unsaturated aliphatic carboxylic or carbamic acid containing 2 to 18 carbon atoms, an acyl radical of a cycloaliphatic carboxylic or carbamic acid containing 7 to 12 carbon atoms, an acyl radical of an aromatic carboxylic acid containing 7 to 15 carbon atoms, or R 4 and R 5 together are -(CH 2 )5CO-, phthaloyl or a divalent acyl radical of maleic acid;
- R 6 is alkoxy of 1 to 18 carbon atoms, alkenyloxy of 2 to 18 carbon atoms, -NHalkyl of 1 to 18 carbon atoms or -N(alkyl) 2 of 2 to 36 carbon atoms,
- R 6 is a tetravalent alkoxy radical of a saturated or unsaturated aliphatic tetraol containing 4 to 18 carbon atoms
- R 9 is oxygen, or R g is nitrogen substituted by either hydrogen, alkyl of 1 to 12 carbon atoms or Ti
- R 10 is hydrogen or methyl
- Rn and R 12 are independently hydrogen or the group T 2
- R 3 is hydrogen, phenyl, straight or branched alkyl of 1 to 12 carbon atoms, alkoxy of 1 to 12 carbon atoms, straight or branched alkyl of 1 to 4 carbon atoms substituted by phenyl, cycloalkyl of 5 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms, alkenyl of 2 to 12 carbon atoms, glycidyl, allyloxy, straight or branched hydroxyalkyl of 1 to 4 carbon atoms, or silyl or silyloxy substituted three times independently by hydrogen, by phenyl, by alkyl of 1 to 4 carbon atoms or by alkoxy of 1 to 4 carbon atoms;
- R ⁇ is hydrogen or silyl substituted three times independently by hydrogen, by phenyl, by alkyl of 1 to 4 carbon atoms or by alkoxy of 1 to 4 carbon atoms;
- h 0 to 4.
- k 0 to 5;
- x is 3 to 6;
- y is 1 to 10;
- z is an integer such that the compound has a molecular weight of 1000 to 4000 amu, e.g. z may be from the range 3-10;
- R 15 is morpholino, piperidino, 1-piperizinyl, alkylamino of 1 to 8 carbon atoms, especially branched alkylamino of 3 to 8 carbon atoms such as tert-octylamino, -N(alkyl)T 1 with alkyl of 1 to 8 carbon atoms, or -N(alkyl) 2 of 2 to 16 carbon atoms,
- R 16 is hydrogen, acyl of 2 to 4 carbon atoms, carbamoyl substituted by alkyl of 1 to 4 carbon atoms, s-triazinyl substituted once by chlorine and once by R 15 , or s-triazinyl substituted twice by R 15 with the condition that the two R 15 substituents may be different;
- R 17 is chlorine, amino substituted by alkyl of 1 to 8 carbon atoms or by T ⁇ -N(alkyl)T- ⁇ with alkyl of 1 to 8 carbon atoms, -N(alkyl) 2 of 2 to 16 carbon atoms, or the group T 3
- R s is hydrogen, acyl of 2 to 4 carbon atoms, carbamoyl substituted by alkyl of 1 to 4 carbon atoms, s-triazinyl substituted twice by -N(alkyl) 2 of 2 to 16 carbon atoms or s-triazinyl substituted twice by -N(alkyl)T ⁇ with alkyl of 1 to 8 carbon atoms;
- R14, d,h, k, m, q, and Ti have the same meanings as in formulas (1) to (15);
- R 19 is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, glycidyl, 2,3-dihydroxypropyl, 2-hydroxy or 2-(hydroxymethyl) substituted alkyl of 3 to 12 carbon atoms which alkyl is interrupted by oxygen, an acyl radical of an aliphatic or unsaturated aliphatic carboxylic or carbamic acid containing 2 to 18 carbon atoms, an acyl radical of a cycloaliphatic carboxylic or carbamic acid containing 7 to 12 carbon atoms, or acyl radical of an aromatic acid containing 7 to 15 carbon atoms;
- R 20 is alkylene of 2 to 18 carbon atoms, a divalent acyl radical of an aliphatic or unsaturated aliphatic dicarboxylic or dicarbamic acid containing 2 to 18 carbon atoms, a divalent acyl radical of a cycloaliphatic dicarboxylic or dicarbamic acid containing 7 to 12 carbon atoms, or a divalent acyl radical of an aromatic dicarboxylic acid containing 8 to 15 carbon atoms;
- R 2 3 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 2 to 6 carbon atoms;
- R 24 is alkylene of 2 to 18 carbon atoms, a divalent acyl radical of an aliphatic or unsaturated aliphatic dicarboxylic or dicarbamic acid containing 2 to 18 carbon atoms, a divalent acyl radical of a cycloaliphatic dicarboxylic or dicarbamic acid containing 7 to 12 carbon atoms, or a divalent acyl radical of an aromatic dicarboxylic acid containing 8 to 15 carbon atoms;
- R 2 5 is alkoxy of 1 to 18 carbon atoms, alkenyloxy of 2 to 18 carbon atoms, -NHalkyl of 1 to 18 carbon atoms or -N(alkyl) 2 of 2 to 36 carbon atoms,
- R 26 is alkylenedioxy of 2 to 18 carbon atoms, alkenylenedioxy of 2 to 18 carbon atoms, -NH-alkylene-NH- of 2 to 18 carbon atoms or -N(alkyI)-alkylene-N(alkyl)- of 3 to 18 carbon atoms.
- E is a carbon centered radical formed preferably from a C -Cnphenylalkane, especially toluene, ethylbenzene, isopropylbenzene; or C 5 -C ⁇ 2 cycloalkane, especially cyclohexene; or C 5 -C 12 cycloalkene, especially cyclohexene; or C 3 -C 8 alkene, especially propene; or a benzene which is substituted by C ⁇ -C alkyl and a further substituent selected from CrC alkoxy, glycidyl or glycidyloxy.
- Products of the present process can be employed with advantage for stabilizing organic material against the damaging effect of light, oxygen and/or heat, especially for stabilizing synthetic organic polymers or compositions containing them. They are notable for high thermal stability, substrate compatibility and good persistence in the substrate.
- thermoplastic polymers of most importance in present compositions are polyolefines and their copolymers, thermoplastic polyolefin (TPO), thermoplastic polyurethan (TPU), thermoplastic rubber (TPR), polycarbonate, such as in item 19 above, and blends, such as in item 28 above.
- TPO thermoplastic polyolefin
- TPU thermoplastic polyurethan
- TPR thermoplastic rubber
- polycarbonate such as in item 19 above
- blends such as in item 28 above.
- PE polyethylene
- PP polypropylene
- PC polycarbonate
- the regulator/initiator compound is present in an amount of from 0.01 mol-% to 30 mol-% , more preferably in an amount of from 0.1 mol-% to 20 mol-% and most preferred in an amount of from 0.5 mol-% to 10 mol-% based on the monomer or monomer mixture.
- the reaction mixture is cooled down to 25°C and stirred with 61 g of an aqueous solution of Na 2 SO 3 (10%) until the disappearance of excess t-butylhydroperoxide.
- the aqueous phase is then separated and washed with ethylbenzene.
- the combined organic phases are washed with brine, dried over MgSO 4 , filtered, and the solvent is distilled off on a rotary-evaporator.
- the crude product is purified by flash-chromatography (silica gel, hexane : ethylacetate 9 : 1), yielding 5 g (60 % of theory) of a yellow oil.
- Example 2 Example 1 is repeated except that 32 mmol of 2,2,6,6-Tetramethylpiperidine-N- oxide are replaced by the equivalent amount of 2,2,6,6-Tetramethylpiperidine-4-one-N-oxide,
- a stirred mixture of 0.5g (3.2 mmol) TEMPO, 1.14 g (6.4 mmol) of 2-(4-ethyl-phenoxymethyl)- oxirane, 0.0118 g (0.032 mmol) of tetrabutylammoniumiodide and 0.62 g (4.8 mmol) of t- butylhydroperoxid (70% aqueous solution) is brought to 60°C. The temperature is maintained at 60°C for 4 hours until all of the TEMPO has reacted. The reaction mixture is cooled down to 25°C and stirred with 20g of a 10% aqueous Na 2 SO 3 solution until the disappearance of excess t-butylhydroperoxide.
- aqueous phase is then separated and washed with ethylbenzene.
- the combined organic phases are passed through a plug of silica gel, washed with brine, dried over MgSO 4 , filtered and the solvent distilled off on a rotary-evaporator, yielding 0.9 g of a colorless oil.
- Quantitative HPLC-analysis reveals a product-concentration of 65% w/w, corresponding to an overall yield of 54.8%.
- Example 5 A mixture of 4 mmol) of the product of Example 5 and 0.2 g Pd on charcoal (10%) in 10 ml of methanol is hydrogenated at 25°C and 4 bar of hydrogen. Filtration and evaporation of the solvent yields the title product as a slightly orange oil.
- the temperature is maintained at 60°C for another 24 hours, cooled down to 25°C and stirred with 120 g of a 10% aqueous Na 2 SO 3 solution until the disappearance of excess t-butylhydroperoxide.
- the aqueous phase is then separated and washed with ethylbenzene.
- the combined organic phases are washed with brine, dried over MgSO 4 , filtered and the solvent distilled off on a rotary-evaporator.
- the crude product is purified by flash-chromatography (silica gel, hexane : Ethylacetate 9 : 1), yielding the title product as a yellow oil.
- the reaction mixture is cooled down to 25°C and stirred with 47g of an aqueous 10% Na 2 SO 3 solution until the disappearance of excess t-butylhydroperoxide.
- the aqueous phase is then separated and washed with cyclohexane.
- the combined organic phases are washed with brine, dried over MgSO 4 , filtered and the solvent distilled off on a rotary-evaporator, yielding 12.2 g of a brownish oil partially crystallizing at low temperature.
- the title product is obtained as an off-white solid, mp 106°C - 110°C.
- reaction mixture is cooled down to 25°C and stirred with 18.9 g of an aqueous 10% Na 2 SO 3 solution until the disappearance of excess t-butylhydroperoxide.
- the aqueous phase is then separated and washed with cyclohexane.
- the combined organic phases are washed with brine, dried over MgSO 4 , filtered and the solvent distilled off on a rotary-evaporator, yielding 1.1 g g of a reddish solid.
- Purification by flash-chromatography (silica gel, hexane : ethylacetate 9 : 1) yields the title product as a white solid, mp 86°C - 90°C.
- reaction mixture is cooled down to 25°C and stirred with 132 g of an aqueous 10% Na 2 SO 3 solution until the disappearance of excess t-butylhydroperoxide.
- the aqueous phase is then separated and washed with cyclohexane.
- the combined organic phases are washed with brine, dried over MgSO 4 , filtered and the solvent distilled off on a rotary-evaporator, yielding 10 g of a reddish oil.
- Purification by flash-chromatography (silica gel, hexane : ethylacetate 9 : 1 ) yields the title product as a yellowish oil.
- Example 14 Preparation of the compound of Example 1 with the catalyst Bu 4 NI generated in situ from Bu 4 NCI / Nal; yield determination by HPLC
- Example 15 Preparation of the compound of Example 12 using immobilized onium iodide. This allows the catalyst be filtered off after the reaction.
- the reaction mixture is cooled down to 25°C and the catalyst filtered off.
- the filtrate is stirred with 57 g of an aqueous 10% Na 2 SO 3 solution until the disappearance of excess t- butylhydroperoxide.
- the aqueous phase is then separated and washed with cyclohexane.
- the combined organic phases are washed with brine, dried over MgSO 4 , filtered and the solvent distilled off on a rotary-evaporator, yielding 10.7 g (94% of theory) of the title product as a slightly orange oil.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02787731A EP1463717A2 (en) | 2001-11-26 | 2002-11-19 | Process for the synthesis of amine ethers from secondary amino oxides and uses |
BR0214429-8A BR0214429A (en) | 2001-11-26 | 2002-11-19 | Process for Synthesis of Amine Ethers from Secondary Amino Oxides and Uses |
KR10-2004-7007982A KR20040058329A (en) | 2001-11-26 | 2002-11-19 | Process for the synthesis of amine ethers from secondary amino oxides and uses |
CA002464107A CA2464107A1 (en) | 2001-11-26 | 2002-11-19 | Process for the synthesis of amine ethers from secondary amino oxides and uses |
JP2003547371A JP2005516905A (en) | 2001-11-26 | 2002-11-19 | Synthetic methods and uses of amine ethers from secondary amino oxides |
MXPA04004694A MXPA04004694A (en) | 2001-11-26 | 2002-11-19 | Process for the synthesis of amine ethers from secondary amino oxides. |
AU2002352057A AU2002352057A1 (en) | 2001-11-26 | 2002-11-19 | Process for the synthesis of amine ethers from secondary amino oxides and uses |
US10/496,773 US20050104042A1 (en) | 2001-11-26 | 2002-11-19 | Process for the synthesis of amine ethers from secondary amino oxides |
Applications Claiming Priority (2)
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EP01811143.5 | 2001-11-26 | ||
EP01811143 | 2001-11-26 |
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WO2003045919A2 true WO2003045919A2 (en) | 2003-06-05 |
WO2003045919A3 WO2003045919A3 (en) | 2004-04-29 |
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PCT/EP2002/012957 WO2003045919A2 (en) | 2001-11-26 | 2002-11-19 | Process for the synthesis of amine ethers from secondary amino oxides and uses |
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US (1) | US20050104042A1 (en) |
EP (1) | EP1463717A2 (en) |
JP (1) | JP2005516905A (en) |
KR (1) | KR20040058329A (en) |
CN (1) | CN100349870C (en) |
AU (1) | AU2002352057A1 (en) |
BR (1) | BR0214429A (en) |
CA (1) | CA2464107A1 (en) |
MX (1) | MXPA04004694A (en) |
TW (1) | TW200407307A (en) |
WO (1) | WO2003045919A2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005090307A1 (en) * | 2004-03-15 | 2005-09-29 | Ciba Specialty Chemicals Holding Inc. | A process for the synthesis of amine ethers |
WO2006048389A1 (en) * | 2004-11-02 | 2006-05-11 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of n-alkoxyamines |
WO2008003602A1 (en) * | 2006-07-05 | 2008-01-10 | Ciba Holding Inc. | Process for the preparation of sterically hindered nitroxyl ethers |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4873612B2 (en) * | 2005-12-20 | 2012-02-08 | 株式会社Adeka | Method for producing hindered amine compound |
CN101484422B (en) * | 2006-07-05 | 2012-07-11 | 西巴控股有限公司 | Process for the preparation of sterically hindered nitroxyl ethers |
ATE449072T1 (en) * | 2006-07-05 | 2009-12-15 | Basf Se | METHOD FOR PRODUCING STERICALLY HINDERED NITROXYL ETHER |
WO2009070693A2 (en) * | 2007-11-28 | 2009-06-04 | Sirion Therapeutics, Inc | Modulators of ocular oxidative stress |
WO2009076631A1 (en) * | 2007-12-12 | 2009-06-18 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
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US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
GB2335190A (en) * | 1998-03-09 | 1999-09-15 | Ciba Geigy Ag | 1-Alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators |
WO2001092228A2 (en) * | 2000-05-26 | 2001-12-06 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of amine ethers from secondary amino oxides |
Family Cites Families (7)
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US5374729A (en) * | 1992-05-07 | 1994-12-20 | Ciba-Geigy Corporation | Process for preparing N-methoxy derivatives of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 2,2,6,6-tetramethyl-4-piperidone |
SG74700A1 (en) * | 1998-02-25 | 2000-08-22 | Ciba Sc Holding Ag | Preparation of sterically hindered amine ethers |
ITMI980366A1 (en) * | 1998-02-25 | 1999-08-25 | Ciba Spec Chem Spa | PREPARATION OF STERICALLY PREVENTED AMINE ETHERS |
US6211378B1 (en) * | 1998-10-13 | 2001-04-03 | Ciba Specialty Chemicals Corporation | Process for the synthesis of 4-substituted N-[(alk-2-en-1-yl)oxy]-and N-aralkyloxy-2,2,6,6-tetraalkylpiperidines |
US6166212A (en) * | 1999-05-20 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Process for the synthesis of N-(hydroxyalkoxy) substituted hindered amine stabilizers |
US6271377B1 (en) * | 1999-02-25 | 2001-08-07 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
US6841668B2 (en) * | 2002-04-11 | 2005-01-11 | Ciba Specialty Chemicals Corporation | Polyoxometalate catalysts for the preparation of sterically hindered N-substituted aryloxyamines |
-
2002
- 2002-11-04 TW TW091132520A patent/TW200407307A/en unknown
- 2002-11-19 WO PCT/EP2002/012957 patent/WO2003045919A2/en active Application Filing
- 2002-11-19 CN CNB028234219A patent/CN100349870C/en not_active Expired - Fee Related
- 2002-11-19 US US10/496,773 patent/US20050104042A1/en not_active Abandoned
- 2002-11-19 EP EP02787731A patent/EP1463717A2/en not_active Withdrawn
- 2002-11-19 CA CA002464107A patent/CA2464107A1/en not_active Abandoned
- 2002-11-19 JP JP2003547371A patent/JP2005516905A/en active Pending
- 2002-11-19 KR KR10-2004-7007982A patent/KR20040058329A/en not_active Application Discontinuation
- 2002-11-19 BR BR0214429-8A patent/BR0214429A/en not_active IP Right Cessation
- 2002-11-19 MX MXPA04004694A patent/MXPA04004694A/en active IP Right Grant
- 2002-11-19 AU AU2002352057A patent/AU2002352057A1/en not_active Abandoned
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US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
GB2335190A (en) * | 1998-03-09 | 1999-09-15 | Ciba Geigy Ag | 1-Alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators |
WO2001092228A2 (en) * | 2000-05-26 | 2001-12-06 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of amine ethers from secondary amino oxides |
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AHN K-H ET AL: "OXIDATION OF ENOLATE ANION BY HYPERVALENT IODINE COMPOUNDS: SYNTHESIS OF ALPHA-TEMPO CARBONYL COMPOUND, A NEW LIVING RADICAL POLYMERIZATION INITIATOR" SYNTHETIC COMMUNICATIONS, MARCEL DEKKER, INC., BASEL, CH, vol. 29, no. 24, 1999, pages 4361-4366, XP000942767 ISSN: 0039-7911 * |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005090307A1 (en) * | 2004-03-15 | 2005-09-29 | Ciba Specialty Chemicals Holding Inc. | A process for the synthesis of amine ethers |
JP2007529467A (en) * | 2004-03-15 | 2007-10-25 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Synthesis method of amine ether |
WO2006048389A1 (en) * | 2004-11-02 | 2006-05-11 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of n-alkoxyamines |
JP2008519003A (en) * | 2004-11-02 | 2008-06-05 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Method for synthesizing N-alkoxyamine |
EP2993168A1 (en) | 2004-11-02 | 2016-03-09 | Basf Se | Process for the synthesis of n-alkoxyamines |
WO2008003602A1 (en) * | 2006-07-05 | 2008-01-10 | Ciba Holding Inc. | Process for the preparation of sterically hindered nitroxyl ethers |
Also Published As
Publication number | Publication date |
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CN100349870C (en) | 2007-11-21 |
TW200407307A (en) | 2004-05-16 |
JP2005516905A (en) | 2005-06-09 |
AU2002352057A1 (en) | 2003-06-10 |
BR0214429A (en) | 2004-11-03 |
WO2003045919A3 (en) | 2004-04-29 |
US20050104042A1 (en) | 2005-05-19 |
AU2002352057A8 (en) | 2003-06-10 |
CN1592740A (en) | 2005-03-09 |
CA2464107A1 (en) | 2003-06-05 |
MXPA04004694A (en) | 2004-08-19 |
EP1463717A2 (en) | 2004-10-06 |
KR20040058329A (en) | 2004-07-03 |
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