CA1154777A - Methode d'obtention de 2-aryl-2h-benzotriazoles - Google Patents

Methode d'obtention de 2-aryl-2h-benzotriazoles

Info

Publication number: CA1154777A
Authority: CA; Canada
Prior art keywords: tert; hydrogen; carbon atoms; hydroxy; formula
Prior art date: 1975-05-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000249843A

Other languages

English (en)

Inventor

Charles E. Ziegler

Hans J. Peterli

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-05-14

Filing date

1976-04-08

Publication date

1983-10-04

1976-04-08 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1983-10-04 Application granted granted Critical

1983-10-04 Publication of CA1154777A publication Critical patent/CA1154777A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 59
238000004519 manufacturing process Methods 0.000 title claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 73
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 50
239000003054 catalyst Substances 0.000 claims abstract description 48
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
DSZOTMKIKJOOPG-UHFFFAOYSA-N (2-nitrophenyl)-phenyldiazene Chemical class [O-][N+](=O)C1=CC=CC=C1N=NC1=CC=CC=C1 DSZOTMKIKJOOPG-UHFFFAOYSA-N 0.000 claims abstract description 22
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 22
229910052763 palladium Inorganic materials 0.000 claims abstract description 21
239000003513 alkali Substances 0.000 claims abstract description 17
229910052799 carbon Inorganic materials 0.000 claims abstract description 13
229910000510 noble metal Inorganic materials 0.000 claims abstract description 10
239000012298 atmosphere Substances 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 82
-1 carboxyethyl Chemical group 0.000 claims description 65
229910052801 chlorine Inorganic materials 0.000 claims description 53
239000000460 chlorine Substances 0.000 claims description 50
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 45
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 43
150000002431 hydrogen Chemical group 0.000 claims description 33
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
239000012964 benzotriazole Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
229910052703 rhodium Inorganic materials 0.000 claims description 12
239000010948 rhodium Substances 0.000 claims description 12
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
DRPPFIRCBMBJCM-UHFFFAOYSA-N 4-methyl-2-[(2-nitrophenyl)diazenyl]phenol Chemical compound CC1=CC=C(O)C(N=NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 DRPPFIRCBMBJCM-UHFFFAOYSA-N 0.000 claims description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000003610 charcoal Substances 0.000 claims description 6
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 6
229910052697 platinum Inorganic materials 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
HOWCUYQDKCPWDV-UHFFFAOYSA-N 2-[(2-nitrophenyl)diazenyl]-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N=NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 HOWCUYQDKCPWDV-UHFFFAOYSA-N 0.000 claims description 4
238000001914 filtration Methods 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
230000000737 periodic effect Effects 0.000 claims description 3
IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 claims description 2
UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
HHUOYYNHGMRSIF-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)-6-[(2-nitrophenyl)diazenyl]phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N=NC=2C(=CC=CC=2)[N+]([O-])=O)=C1O HHUOYYNHGMRSIF-UHFFFAOYSA-N 0.000 claims 3
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 2
229910017052 cobalt Inorganic materials 0.000 claims 2
239000010941 cobalt Substances 0.000 claims 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 2
229910052750 molybdenum Inorganic materials 0.000 claims 2
239000011733 molybdenum Substances 0.000 claims 2
229910052759 nickel Inorganic materials 0.000 claims 2
HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
239000002585 base Substances 0.000 claims 1
OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 abstract description 19
230000009467 reduction Effects 0.000 abstract description 19
239000006227 byproduct Substances 0.000 abstract description 4
239000000243 solution Substances 0.000 description 24
238000006722 reduction reaction Methods 0.000 description 19
230000000875 corresponding effect Effects 0.000 description 15
239000012043 crude product Substances 0.000 description 11
229960004592 isopropanol Drugs 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
150000004707 phenolate Chemical class 0.000 description 4
KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012535 impurity Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
RPNNPZHFJPXFQS-UHFFFAOYSA-N methane;rhodium Chemical compound C.[Rh] RPNNPZHFJPXFQS-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000006476 reductive cyclization reaction Methods 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000013019 agitation Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
125000006606 n-butoxy group Chemical group 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000011946 reduction process Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000005406 washing Methods 0.000 description 2
FRBUNLLUASHNDJ-UHFFFAOYSA-N (2-nitrophenyl)hydrazine Chemical compound NNC1=CC=CC=C1[N+]([O-])=O FRBUNLLUASHNDJ-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 1
MIMONXWGQIJLGP-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(5-chloro-2-nitrophenyl)diazenyl]phenol Chemical compound [N+](=O)([O-])C1=C(C=C(C=C1)Cl)N=NC1=C(C(=CC(=C1)C(C)(C)C)C(C)(C)C)O MIMONXWGQIJLGP-UHFFFAOYSA-N 0.000 description 1
AHRMZVUDBZEZKW-UHFFFAOYSA-N 2-(2-phenylhydrazinyl)aniline Chemical class NC1=CC=CC=C1NNC1=CC=CC=C1 AHRMZVUDBZEZKW-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
JKFZLMPBXBMSPD-UHFFFAOYSA-N 2-butan-2-yl-4-tert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=CC=C1O JKFZLMPBXBMSPD-UHFFFAOYSA-N 0.000 description 1
MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
AYTSDBGAHOKDHJ-UHFFFAOYSA-N 2-nitrobenzenediazonium Chemical class [O-][N+](=O)C1=CC=CC=C1[N+]#N AYTSDBGAHOKDHJ-UHFFFAOYSA-N 0.000 description 1
GGLOSSFVOIXPQY-UHFFFAOYSA-N 2-tert-butyl-6-[(5-chloro-2-nitrophenyl)diazenyl]-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(N=NC=2C(=CC=C(Cl)C=2)[N+]([O-])=O)=C1O GGLOSSFVOIXPQY-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
PWOSZSKROANIMX-UHFFFAOYSA-N ClC1=CC(=C(N)C=C1)[N+](=O)[O-].[N+](=O)([O-])C1=C(N)C=CC=C1 Chemical compound ClC1=CC(=C(N)C=C1)[N+](=O)[O-].[N+](=O)([O-])C1=C(N)C=CC=C1 PWOSZSKROANIMX-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
BPAUORSLTVXEBC-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC1N)S(=O)(=O)O.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1N.C(CCC)OC1=CC(=C(N)C=C1)[N+](=O)[O-].[N+](=O)([O-])C=1C=C(C(=O)OCCCCCCCC)C=CC1N Chemical compound [N+](=O)([O-])C=1C=C(C=CC1N)S(=O)(=O)O.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1N.C(CCC)OC1=CC(=C(N)C=C1)[N+](=O)[O-].[N+](=O)([O-])C=1C=C(C(=O)OCCCCCCCC)C=CC1N BPAUORSLTVXEBC-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
150000001565 benzotriazoles Chemical class 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical group 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
229910052920 inorganic sulfate Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
FZZMDWLROBNSRG-UHFFFAOYSA-N n-phenyliminonitramide Chemical compound [O-][N+](=O)N=NC1=CC=CC=C1 FZZMDWLROBNSRG-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 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
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
229940093932 potassium hydroxide Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
238000011282 treatment Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA000249843A 1975-05-14 1976-04-08 Methode d'obtention de 2-aryl-2h-benzotriazoles Expired CA1154777A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US57738475A	1975-05-14	1975-05-14
US577,384		1975-05-14
US663,330		1976-03-03
US66333076A	1976-03-04	1976-03-04

Publications (1)

Publication Number	Publication Date
CA1154777A true CA1154777A (fr)	1983-10-04

Family

ID=27077226

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000249843A Expired CA1154777A (fr)	1975-05-14	1976-04-08	Methode d'obtention de 2-aryl-2h-benzotriazoles

Country Status (2)

Country	Link
CA (1)	CA1154777A (fr)
IT (1)	IT1071652B (fr)

1976
- 1976-04-08 CA CA000249843A patent/CA1154777A/fr not_active Expired
- 1976-05-13 IT IT2324176A patent/IT1071652B/it active

Also Published As

Publication number	Publication date
IT1071652B (it)	1985-04-10

Legal Events

Date	Code	Title	Description
2000-10-04	MKEX	Expiry

Publication	Publication Date	Title
US4230867A (en)	1980-10-28	Process for the production of 2-aryl-2H-benzotriazoles
CA1062266A (fr)	1979-09-11	Procede pour la production de 2-aryl-2h-benzotriazoles
US4275004A (en)	1981-06-23	High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes
US4347180A (en)	1982-08-31	High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes
US6605727B2 (en)	2003-08-12	Processes for the preparation of benzotriazole UV absorbers
US4219480A (en)	1980-08-26	Process for the production of 2-aryl-2H-benzotriazoles
US4141903A (en)	1979-02-27	Process for the production of 2-aryl-2H-benzotriazoles
US4642350A (en)	1987-02-10	Novel process for preparation of benzotriazoles using aryldiols and quinones
DE2454889A1 (de)	1975-05-28	Verfahren zur herstellung von 2(2-hydroxyphenyl)-benztriazolen
US5675015A (en)	1997-10-07	Process for the preparation of benzotriazole derivatives
CA1154777A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
JPS6036429B2 (ja)	1985-08-20	２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法
US5739348A (en)	1998-04-14	Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process
US5104992A (en)	1992-04-14	Method of preparing 2-phenyl benezothriazoles
JPS6036431B2 (ja)	1985-08-20	２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法
JPS6036430B2 (ja)	1985-08-20	２‐アリール‐２ｈ‐ベンゾトリアゾール類の製造方法
US5436322A (en)	1995-07-25	Azo coupling of 2-nitroanilines with 2,4,-disbustituted phenols
US5187289A (en)	1993-02-16	Method of preparing 2-phenyl benzotriazoles
JPS6036432B2 (ja)	1985-08-20	２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法
US3733338A (en)	1973-05-15	1-oxo-isochromenes
CA1154778A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
US4980505A (en)	1990-12-25	Organic synthesis
CA1241659A (fr)	1988-09-06	Methode de preparation de 2-phenylbenzotriazole
CA1154779A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
US3116330A (en)	1963-12-31	Nu-aminophenylethyl-2, 2-diphenyl-alkylamines