WO2008003602A1 - Process for the preparation of sterically hindered nitroxyl ethers - Google Patents
Process for the preparation of sterically hindered nitroxyl ethers Download PDFInfo
- Publication number
- WO2008003602A1 WO2008003602A1 PCT/EP2007/056292 EP2007056292W WO2008003602A1 WO 2008003602 A1 WO2008003602 A1 WO 2008003602A1 EP 2007056292 W EP2007056292 W EP 2007056292W WO 2008003602 A1 WO2008003602 A1 WO 2008003602A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- alkyl
- hydrogen
- substituted
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- -1 nitroxyl ethers Chemical class 0.000 title claims description 176
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 89
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 144
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- 239000003054 catalyst Substances 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 150000002576 ketones Chemical class 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 150000001299 aldehydes Chemical class 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 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 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052797 bismuth Inorganic materials 0.000 claims description 5
- 125000005594 diketone group Chemical group 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- 125000006193 alkinyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005466 alkylenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical group CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 3
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 claims description 2
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- ZINWPIUEIVPAIN-UHFFFAOYSA-N pentane-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)C(C(O)=O)CC(O)=O ZINWPIUEIVPAIN-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims 1
- SVWNWENIKZQJLL-UHFFFAOYSA-N 1-(cyclohexen-1-yloxy)-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1OC1=CCCCC1 SVWNWENIKZQJLL-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 4
- 239000003063 flame retardant Substances 0.000 abstract description 3
- 150000001728 carbonyl compounds Chemical class 0.000 abstract description 2
- 230000009931 harmful effect Effects 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000012074 organic phase Substances 0.000 description 41
- 239000000203 mixture Substances 0.000 description 38
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 229910052938 sodium sulfate Inorganic materials 0.000 description 27
- 235000002639 sodium chloride Nutrition 0.000 description 26
- 235000011152 sodium sulphate Nutrition 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- 239000011780 sodium chloride Substances 0.000 description 20
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 229910000029 sodium carbonate Inorganic materials 0.000 description 17
- 239000012071 phase Substances 0.000 description 16
- 235000010323 ascorbic acid Nutrition 0.000 description 15
- 229960005070 ascorbic acid Drugs 0.000 description 15
- 239000011668 ascorbic acid Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 12
- 239000013065 commercial product Substances 0.000 description 12
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003444 phase transfer catalyst Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- BVWHOCIBGVSRSY-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-propoxypiperidin-4-ol Chemical compound CCCON1C(C)(C)CC(O)CC1(C)C BVWHOCIBGVSRSY-UHFFFAOYSA-N 0.000 description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 4
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- ILLXRYVHDVZNQZ-UHFFFAOYSA-N 1-ethoxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CCON1C(C)(C)CC(O)CC1(C)C ILLXRYVHDVZNQZ-UHFFFAOYSA-N 0.000 description 3
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-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
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000001402 nonanoyl 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])[H] 0.000 description 1
- 125000005187 nonenyl group Chemical class C(=CCCCCCCC)* 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- JZZRXECTAQPLNI-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O.CCCCC=O JZZRXECTAQPLNI-UHFFFAOYSA-N 0.000 description 1
- 125000006194 pentinyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group 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
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical class CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-N sodium;2-[dodecanoyl(methyl)amino]acetic acid Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC(O)=O KSAVQLQVUXSOCR-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 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
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 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
- 125000005065 undecenyl group Chemical class C(=CCCCCCCCCC)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07786819A EP2035381B1 (en) | 2006-07-05 | 2007-06-25 | Process for the preparation of sterically hindered nitroxyl ethers |
DE602007011607T DE602007011607D1 (en) | 2006-07-05 | 2007-06-25 | METHOD FOR THE PRODUCTION OF STERRICALLY PREVENTED NITROXYL ETHER |
US12/308,519 US8471031B2 (en) | 2006-07-05 | 2007-06-25 | Process for the preparation of sterically hindered nitroxyl ethers |
CN2007800252119A CN101484422B (en) | 2006-07-05 | 2007-06-25 | Process for the preparation of sterically hindered nitroxyl ethers |
MX2008016304A MX2008016304A (en) | 2006-07-05 | 2007-06-25 | Process for the preparation of sterically hindered nitroxyl ethers. |
CA2655690A CA2655690C (en) | 2006-07-05 | 2007-06-25 | Process for the preparation of sterically hindered nitroxyl ethers |
AT07786819T ATE493387T1 (en) | 2006-07-05 | 2007-06-25 | METHOD FOR PRODUCING STERICALLY HINDERED NITROXYL ETHER |
JP2009517147A JP5307002B2 (en) | 2006-07-05 | 2007-06-25 | Method for producing sterically hindered nitroxyl ether |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06116619.5 | 2006-07-05 | ||
EP06116619 | 2006-07-05 | ||
EP07102895.5 | 2007-02-22 | ||
EP07102895 | 2007-02-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008003602A1 true WO2008003602A1 (en) | 2008-01-10 |
Family
ID=38606619
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/056292 WO2008003602A1 (en) | 2006-07-05 | 2007-06-25 | Process for the preparation of sterically hindered nitroxyl ethers |
Country Status (10)
Country | Link |
---|---|
US (1) | US8471031B2 (en) |
EP (1) | EP2035381B1 (en) |
JP (1) | JP5307002B2 (en) |
KR (1) | KR101468481B1 (en) |
AT (1) | ATE493387T1 (en) |
CA (1) | CA2655690C (en) |
DE (1) | DE602007011607D1 (en) |
MX (1) | MX2008016304A (en) |
TW (1) | TWI428321B (en) |
WO (1) | WO2008003602A1 (en) |
Cited By (8)
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WO2010023115A1 (en) * | 2008-08-28 | 2010-03-04 | Basf Se | Stabilisers for inanimate organic materials |
WO2011086114A1 (en) | 2010-01-15 | 2011-07-21 | Basf Se | Phospho-substituted alkoxyamine compounds |
WO2011107515A2 (en) | 2010-03-05 | 2011-09-09 | Basf Se | Sterically hindered amines |
WO2011120947A1 (en) | 2010-03-30 | 2011-10-06 | Basf Se | End-functionalized polymers |
WO2012052377A1 (en) | 2010-10-20 | 2012-04-26 | Basf Se | Sterically hindered amine light stabilizers with mixed functionalization |
WO2013095912A1 (en) * | 2011-12-19 | 2013-06-27 | Rohm And Haas Company | Improved method for the preparation of n-oxyl hindered amine inhibitors |
WO2013136285A1 (en) | 2012-03-16 | 2013-09-19 | Basf Se | Nor-hals compounds as flame retardants |
WO2023194065A1 (en) * | 2022-04-04 | 2023-10-12 | Zedda Innovation Consulting | Process for the preparation of sterically hindered nitroxyl ethers |
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Publication number | Priority date | Publication date | Assignee | Title |
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CA2654837C (en) * | 2006-07-05 | 2015-11-24 | Ciba Holding Inc. | Process for the preparation of sterically hindered nitroxyl ethers |
JP5224497B2 (en) * | 2007-02-22 | 2013-07-03 | 株式会社Adeka | Resin composition |
WO2011068110A1 (en) | 2009-12-01 | 2011-06-09 | 三菱レイヨン株式会社 | Method of producing a polymer using monomers having a piperidine skeleton, and molded body |
KR101921776B1 (en) | 2011-05-30 | 2018-11-23 | 미쯔비시 케미컬 주식회사 | Molding material and molding |
EP2716666B1 (en) | 2011-05-31 | 2017-11-15 | Mitsubishi Chemical Corporation | Curing composition and polymer |
ES2806550T3 (en) * | 2012-03-16 | 2021-02-18 | Basf Se | NOR-HALS compounds as flame retardants |
EP2789609A1 (en) * | 2013-04-11 | 2014-10-15 | Bruker Biospin (SAS) | Highly efficient polarizing agents for dynamic nuclear polarization |
EP3237382A1 (en) | 2014-12-22 | 2017-11-01 | 3M Innovative Properties Company | Sterically hindered alkyl and oxyalkyl amine light stabilizers |
WO2016105990A1 (en) | 2014-12-22 | 2016-06-30 | 3M Innovative Properties Company | Sterically hindered amine and oxyalkyl amine light stabilizers |
US20170283444A1 (en) | 2014-12-22 | 2017-10-05 | 3M Innovative Properties Company | Sterically hindered amine and oxyalkyl amine light stabilizers |
US20170305855A1 (en) | 2014-12-22 | 2017-10-26 | 3M Innovative Properties Company | Sterically hindered amine and oxyalkyl amine light stabilizers |
CN107922680A (en) * | 2015-12-14 | 2018-04-17 | 株式会社藤仓 | Fire retardant resin composition, metal cable and Connectorized fiber optic cabling and products formed using the fire retardant resin composition |
JP6943386B2 (en) * | 2017-04-28 | 2021-09-29 | 山田 健一 | Method for detecting radicals derived from lipids and compounds derived from radicals |
JP7356698B2 (en) * | 2019-06-21 | 2023-10-05 | 学校法人五島育英会 | Compounds, methods for producing compounds, methods for producing polymers, polymers |
CN112250668A (en) * | 2020-10-10 | 2021-01-22 | 利安隆凯亚(河北)新材料有限公司 | Preparation method of N-alkoxy hindered amine light stabilizer and intermediate thereof |
CN113413569B (en) * | 2021-05-31 | 2022-08-16 | 广东邦普循环科技有限公司 | Fire extinguishing agent capable of extinguishing aluminum slag combustion and preparation method and application thereof |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
EP0389419A1 (en) * | 1989-03-21 | 1990-09-26 | Ciba-Geigy Ag | Non-migrating 1-hydrocarbyloxy hindered amine compounds as polymer stabilizers |
EP0569334A1 (en) * | 1992-05-07 | 1993-11-10 | Ciba-Geigy Ag | Process for preparing N-methoxy derivatives of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 2,2,6,6-tetramethyl-4-piperidone |
DE10008367A1 (en) * | 1999-02-25 | 2000-08-31 | Ciba Sc Holding Ag | New 1-alkoxy-substituted hindered 2,2,6,6-tetramethylpiperidine group-containing amines useful as stabilizers for (thermoplastic) polymers, coatings, color photographic materials and printing inks |
WO2001092228A2 (en) * | 2000-05-26 | 2001-12-06 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of amine ethers from secondary amino oxides |
WO2003045919A2 (en) * | 2001-11-26 | 2003-06-05 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of amine ethers from secondary amino oxides and uses |
WO2005005388A1 (en) * | 2003-07-14 | 2005-01-20 | Ciba Specialty Chemicals Holding Inc. | Hydrogen peroxide catalyzed process for the preparation of sterically hindered n-hydrocarbyloxyamines |
WO2005090307A1 (en) * | 2004-03-15 | 2005-09-29 | Ciba Specialty Chemicals Holding Inc. | A process for the synthesis of amine ethers |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7361755B2 (en) * | 2001-12-21 | 2008-04-22 | Ciba Specialty Chemicals Corporation | Transition-metal-catalyzed process for the conversion of alkenes to sterically hindered substituted n-alkoxyamines |
-
2007
- 2007-06-25 WO PCT/EP2007/056292 patent/WO2008003602A1/en active Application Filing
- 2007-06-25 AT AT07786819T patent/ATE493387T1/en not_active IP Right Cessation
- 2007-06-25 JP JP2009517147A patent/JP5307002B2/en active Active
- 2007-06-25 DE DE602007011607T patent/DE602007011607D1/en active Active
- 2007-06-25 MX MX2008016304A patent/MX2008016304A/en active IP Right Grant
- 2007-06-25 EP EP07786819A patent/EP2035381B1/en active Active
- 2007-06-25 CA CA2655690A patent/CA2655690C/en active Active
- 2007-06-25 US US12/308,519 patent/US8471031B2/en active Active
- 2007-07-03 TW TW096124199A patent/TWI428321B/en active
-
2008
- 2008-12-15 KR KR1020087030517A patent/KR101468481B1/en active IP Right Grant
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
EP0389419A1 (en) * | 1989-03-21 | 1990-09-26 | Ciba-Geigy Ag | Non-migrating 1-hydrocarbyloxy hindered amine compounds as polymer stabilizers |
EP0569334A1 (en) * | 1992-05-07 | 1993-11-10 | Ciba-Geigy Ag | Process for preparing N-methoxy derivatives of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 2,2,6,6-tetramethyl-4-piperidone |
DE10008367A1 (en) * | 1999-02-25 | 2000-08-31 | Ciba Sc Holding Ag | New 1-alkoxy-substituted hindered 2,2,6,6-tetramethylpiperidine group-containing amines useful as stabilizers for (thermoplastic) polymers, coatings, color photographic materials and printing inks |
WO2001092228A2 (en) * | 2000-05-26 | 2001-12-06 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of amine ethers from secondary amino oxides |
WO2003045919A2 (en) * | 2001-11-26 | 2003-06-05 | Ciba Specialty Chemicals Holding Inc. | Process for the synthesis of amine ethers from secondary amino oxides and uses |
WO2005005388A1 (en) * | 2003-07-14 | 2005-01-20 | Ciba Specialty Chemicals Holding Inc. | Hydrogen peroxide catalyzed process for the preparation of sterically hindered n-hydrocarbyloxyamines |
WO2005090307A1 (en) * | 2004-03-15 | 2005-09-29 | Ciba Specialty Chemicals Holding Inc. | A process for the synthesis of amine ethers |
Non-Patent Citations (7)
Title |
---|
CARL G. JOHNSON, SIGALIT CARON, NEIL V. BLOUGH: "Combined liquid chromatography/mass spectrometry of the radical adducts of a fluorescamine-derivatized nitroxide", ANAL. CHEM., vol. 68, 1996, pages 867 - 872, XP002425023 * |
DEREK H. R. BARTON, BEATRICE M. CHABOT, BIN HU: "The functionalization of saturated hydrocarbons. Part 34. A study on the mechanisn of TEMPO trapping in GIF-type systems", TETRAHEDRON, vol. 52, no. 31, 1996, pages 10301 - 10312, XP004104017 * |
JOSEPH E. BABIARZ, GLEN T. CUNKLE, ANTHONY D. DEBELLIS, DAVID EVELAND, STEPHEN D. PASTOR, SAI P. SHUM: "The thermal reaction of sterically hindered nitroxyl radicals with allylic and benzylic substrates: Experimental and computational evidence for divergent mechanisms", J. ORG. CHEM., vol. 67, 2002, pages 6831 - 6834, XP002456581 * |
MARIUS G. IVAN, J. C. SCAIANO: "A new approach for the detection of carbon-centered radicals in enzymatic processes using prefluorescent probes", PHOTOCHEMISTRY AND PHOTOBIOLOGY, vol. 78, no. 4, 2003, pages 416 - 417, XP002456429 * |
PATRICIA CARLONI, ROBERTO VIANELLI, LUCEDIO GRECI: "Reactions of an indolinonic nitroxide with superoxide radical anion in the presence of alkylhalides. Unexpected formation of a reduced transport product", J. HETEROCYCLIC CHEM., vol. 40, 2003, pages 459 - 464, XP002380865 * |
TAN REN, YOU-CHENG LIU, QING-XIANG GUO: "Selective oxyfunctionalization of ketones using 1-oxopiperidinium salt", BULL. CHEM. SOC. JPN., vol. 69, 1996, pages 2935 - 2941, XP002084451 * |
TSUTOMU INOKUCHI, KEIICHI NAKAGAWA, SIGERU TORII: "One-pot conversion of primary alcohols to alpha-oxygenated alkanals with TEMPO in combination with molecular oxygen and ruthenium complex", TETRAHEDRON LETTERS, vol. 36, no. 18, 1995, pages 3223 - 3226, XP004028231 * |
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US20100249401A1 (en) | 2010-09-30 |
TW200812964A (en) | 2008-03-16 |
EP2035381B1 (en) | 2010-12-29 |
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JP2009541428A (en) | 2009-11-26 |
JP5307002B2 (en) | 2013-10-02 |
ATE493387T1 (en) | 2011-01-15 |
DE602007011607D1 (en) | 2011-02-10 |
MX2008016304A (en) | 2009-01-16 |
KR20090024707A (en) | 2009-03-09 |
CA2655690A1 (en) | 2008-01-10 |
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US8471031B2 (en) | 2013-06-25 |
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