CA1154778A - Methode d'obtention de 2-aryl-2h-benzotriazoles - Google Patents

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

Info

Publication number: CA1154778A
Authority: CA; Canada
Prior art keywords: hydrogen; tert; carbon atoms; benzotriazole; hydroxy
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

CA000250324A

Other languages

English (en)

Inventor

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

1976-04-15

Publication date

1983-10-04

1976-04-15 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 CA1154778A publication Critical patent/CA1154778A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 66
238000004519 manufacturing process Methods 0.000 title claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 74
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 74
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 56
239000003054 catalyst Substances 0.000 claims abstract description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
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 25
229910052763 palladium Inorganic materials 0.000 claims abstract description 25
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 19
229910000510 noble metal Inorganic materials 0.000 claims abstract description 18
229910052799 carbon Inorganic materials 0.000 claims abstract description 15
239000012298 atmosphere Substances 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 81
-1 carboxyethyl Chemical group 0.000 claims description 73
229910052801 chlorine Inorganic materials 0.000 claims description 50
125000000217 alkyl group Chemical group 0.000 claims description 49
239000000460 chlorine Substances 0.000 claims description 47
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 39
150000002431 hydrogen Chemical group 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 18
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 17
239000012964 benzotriazole Substances 0.000 claims description 14
239000002270 dispersing agent Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229910052703 rhodium Inorganic materials 0.000 claims description 14
239000010948 rhodium Substances 0.000 claims description 14
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
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
239000007858 starting material Substances 0.000 claims description 12
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 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
150000004707 phenolate Chemical class 0.000 claims description 9
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
238000001914 filtration Methods 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
229910052697 platinum Inorganic materials 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
239000003610 charcoal Substances 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
230000000737 periodic effect Effects 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 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-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
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
239000000203 mixture Substances 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
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 4
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
QXCQDFIVJBXXKE-UHFFFAOYSA-N (2-pentylphenyl)-phenyldiazene Chemical compound CCCCCC1=CC=CC=C1N=NC1=CC=CC=C1 QXCQDFIVJBXXKE-UHFFFAOYSA-N 0.000 claims 1
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 1
NOBOUFIZFNCGNZ-UHFFFAOYSA-N 2-tert-butyl-6-[(3-chloro-3-methyl-6-nitrocyclohexa-1,5-dien-1-yl)diazenyl]phenol Chemical compound CC(C)(C)C1=CC=CC(N=NC=2C(=CCC(C)(Cl)C=2)[N+]([O-])=O)=C1O NOBOUFIZFNCGNZ-UHFFFAOYSA-N 0.000 claims 1
208000036366 Sensation of pressure Diseases 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 28
230000009467 reduction Effects 0.000 abstract description 25
239000006227 byproduct Substances 0.000 abstract description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
238000006722 reduction reaction Methods 0.000 description 26
239000000243 solution Substances 0.000 description 21
239000000543 intermediate Substances 0.000 description 20
230000000875 corresponding effect Effects 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000012670 alkaline solution Substances 0.000 description 10
239000012043 crude product Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
239000000194 fatty acid Substances 0.000 description 9
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 8
235000014113 dietary fatty acids Nutrition 0.000 description 7
229930195729 fatty acid Natural products 0.000 description 7
229920001223 polyethylene glycol Polymers 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000003513 alkali Substances 0.000 description 5
125000000129 anionic group Chemical group 0.000 description 5
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
239000011707 mineral Substances 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229940068917 polyethylene glycols Drugs 0.000 description 5
239000001593 sorbitan monooleate Substances 0.000 description 5
229940035049 sorbitan monooleate Drugs 0.000 description 5
235000011069 sorbitan monooleate Nutrition 0.000 description 5
CIVLEPQUPHSEBS-UHFFFAOYSA-N 2-[(2-nitrophenyl)diazenyl]phenol Chemical compound OC1=CC=CC=C1N=NC1=CC=CC=C1[N+]([O-])=O CIVLEPQUPHSEBS-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000002091 cationic group Chemical group 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
239000000463 material 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
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000011084 recovery Methods 0.000 description 3
238000006476 reductive cyclization reaction Methods 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
AYTSDBGAHOKDHJ-UHFFFAOYSA-N 2-nitrobenzenediazonium Chemical class [O-][N+](=O)C1=CC=CC=C1[N+]#N AYTSDBGAHOKDHJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
239000002202 Polyethylene glycol Substances 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
238000010521 absorption reaction Methods 0.000 description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
150000008052 alkyl sulfonates Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
238000002955 isolation Methods 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
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 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000344 soap Substances 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
238000005406 washing Methods 0.000 description 2
238000009736 wetting 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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
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 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
LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-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
NJOXSODFMZIZJD-UHFFFAOYSA-N 4-methyl-2-phenyldiazenylphenol Chemical compound CC1=CC=C(O)C(N=NC=2C=CC=CC=2)=C1 NJOXSODFMZIZJD-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004215 Carbon black (E152) Substances 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
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
235000021360 Myristic acid Nutrition 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 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
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
150000001565 benzotriazoles Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
229940095643 calcium hydroxide Drugs 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
150000001735 carboxylic acids Chemical class 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
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
229960003887 dichlorophen Drugs 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000006182 dimethyl benzyl group Chemical group 0.000 description 1
238000009826 distribution Methods 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 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
239000007850 fluorescent dye Substances 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000008040 ionic compounds Chemical class 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
125000006178 methyl benzyl group Chemical group 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 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
239000003921 oil Substances 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
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000002002 slurry 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
239000000600 sorbitol Substances 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000250324A 1975-05-14 1976-04-15 Methode d'obtention de 2-aryl-2h-benzotriazoles Expired CA1154778A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US57738375A	1975-05-14	1975-05-14
US577,383		1975-05-14
US66979276A	1976-03-23	1976-03-23
US669,792		1991-03-15

Publications (1)

Publication Number	Publication Date
CA1154778A true CA1154778A (fr)	1983-10-04

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ID=27077225

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Application Number	Title	Priority Date	Filing Date
CA000250324A Expired CA1154778A (fr)	1975-05-14	1976-04-15	Methode d'obtention de 2-aryl-2h-benzotriazoles

Country Status (2)

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CA (1)	CA1154778A (fr)
IT (1)	IT1071651B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4990623A (en) *	1986-07-28	1991-02-05	Berenbaum Morris B	Sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazoles and/or sulfonated aromatic formaldehyde condensates

1976
- 1976-04-15 CA CA000250324A patent/CA1154778A/fr not_active Expired
- 1976-05-13 IT IT2324076A patent/IT1071651B/it active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4990623A (en) *	1986-07-28	1991-02-05	Berenbaum Morris B	Sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazoles and/or sulfonated aromatic formaldehyde condensates

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Publication number	Publication date
IT1071651B (it)	1985-04-10

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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
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
EP0419412B1 (fr)	1993-11-10	Procédé pour la préparation de benzotriazoles
US4999433A (en)	1991-03-12	Process for the preparation of benzotriazole derivatives
CA1154778A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
US4642350A (en)	1987-02-10	Novel process for preparation of benzotriazoles using aryldiols and quinones
US4001266A (en)	1977-01-04	Process for the manufacture of 2-(2-hydroxyphenyl)benztriazoles
JPS6036429B2 (ja)	1985-08-20	２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法
CH615427A5 (en)	1980-01-31	Process for the preparation of 2-aryl-2H-benzotriazoles
US3230259A (en)	1966-01-18	Preparation of o-phenylenediamines
US5675015A (en)	1997-10-07	Process for the preparation of benzotriazole derivatives
US4220788A (en)	1980-09-02	Process for the preparation of 2-aryl-2H-benzotriazoles
EP0380840B1 (fr)	1995-05-17	Procédé de préparation de phényl-2 benzotriazoles
CA1073463A (fr)	1980-03-11	Procede pour la production de 2-aryl-2h-benzotriazoles
US5739348A (en)	1998-04-14	Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process
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
CA1154779A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
US2605282A (en)	1952-07-29	Process for production of beta-(3, 4-dihydroxyphenyl)-alanine
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
CA1154777A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
DE2609530B1 (de)	1977-08-04	Verfahren zur herstellung von hydrazobenzol
US5101031A (en)	1992-03-31	Preparation of 2,4,5-triamino-6-hydroxypyrimidine by catalytic hydrogenation of 2,4-diamino-6-hydroxy-5-nitroso-pyrimidine

CA1154778A - Methode d'obtention de 2-aryl-2h-benzotriazoles - Google Patents

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Applications Claiming Priority (4)

Publications (1)

Family

ID=27077225

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Cited By (1)

Cited By (1)

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