DE2620897A1 - Verfahren zur herstellung von 2-aryl-2h-benzotriazolen - Google Patents
Verfahren zur herstellung von 2-aryl-2h-benzotriazolenInfo
- Publication number
- DE2620897A1 DE2620897A1 DE19762620897 DE2620897A DE2620897A1 DE 2620897 A1 DE2620897 A1 DE 2620897A1 DE 19762620897 DE19762620897 DE 19762620897 DE 2620897 A DE2620897 A DE 2620897A DE 2620897 A1 DE2620897 A1 DE 2620897A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- tert
- chlorine
- hydroxy
- butyl
- Prior art date
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- -1 carboxyethyl Chemical group 0.000 claims description 47
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 229910052763 palladium Inorganic materials 0.000 claims description 19
- 239000003513 alkali Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 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 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
- 229910000510 noble metal Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 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
- 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 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 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 238000006722 reduction reaction Methods 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- DSZOTMKIKJOOPG-UHFFFAOYSA-N (2-nitrophenyl)-phenyldiazene Chemical class [O-][N+](=O)C1=CC=CC=C1N=NC1=CC=CC=C1 DSZOTMKIKJOOPG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 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 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 150000002085 enols Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000004707 phenolate Chemical class 0.000 description 3
- 238000006476 reductive cyclization reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- POSPYBFZFFJFKJ-UHFFFAOYSA-N (1-methylcyclohexa-2,4-dien-1-yl)-phenyldiazene Chemical compound CC1(CC=CC=C1)N=NC1=CC=CC=C1 POSPYBFZFFJFKJ-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-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
- 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
- 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 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
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 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
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-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
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- FSGTULQLEVAYRS-UHFFFAOYSA-N 4,5-dichloro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O FSGTULQLEVAYRS-UHFFFAOYSA-N 0.000 description 1
- ZZNAYFWAXZJITH-UHFFFAOYSA-N 4-amino-3-nitrobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1[N+]([O-])=O ZZNAYFWAXZJITH-UHFFFAOYSA-N 0.000 description 1
- BBELMWNCSCNWAO-UHFFFAOYSA-N 4-butoxy-2-nitroaniline Chemical compound CCCCOC1=CC=C(N)C([N+]([O-])=O)=C1 BBELMWNCSCNWAO-UHFFFAOYSA-N 0.000 description 1
- RUQAPQLDPWSAQM-UHFFFAOYSA-N 4-ethyl-2-nitroaniline Chemical compound CCC1=CC=C(N)C([N+]([O-])=O)=C1 RUQAPQLDPWSAQM-UHFFFAOYSA-N 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-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
- LEIKNYPPYVXJIC-UHFFFAOYSA-N C1(O)=CC(O)=CC=C1.C(CCCCCCCCCCC)C1=CC=C(C=C1)O Chemical compound C1(O)=CC(O)=CC=C1.C(CCCCCCCCCCC)C1=CC=C(C=C1)O LEIKNYPPYVXJIC-UHFFFAOYSA-N 0.000 description 1
- ZJXOJOXHDMKTTC-UHFFFAOYSA-N CC(C)(C)C1(C=CC=CC1)N=NC1=CC=CC(C(C)(C)C)=C1 Chemical compound CC(C)(C)C1(C=CC=CC1)N=NC1=CC=CC(C(C)(C)C)=C1 ZJXOJOXHDMKTTC-UHFFFAOYSA-N 0.000 description 1
- HZTDANDTIGENDC-UHFFFAOYSA-N CC(C)(C)CC(C)(C)C1(C=CC=CC1)N=NC1=CC=CC=C1 Chemical compound CC(C)(C)CC(C)(C)C1(C=CC=CC1)N=NC1=CC=CC=C1 HZTDANDTIGENDC-UHFFFAOYSA-N 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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000001174 ascending effect Effects 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000356 contaminant Substances 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000000605 extraction Methods 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
- 239000012535 impurity Substances 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 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
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
- VBCWAVLAZJEGCS-UHFFFAOYSA-N octyl 4-amino-3-nitrobenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 VBCWAVLAZJEGCS-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
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229930195143 oxyphenol Natural products 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000007793 ph indicator Substances 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 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
- 239000012429 reaction media Substances 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000010802 sludge 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
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57738475A | 1975-05-14 | 1975-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2620897A1 true DE2620897A1 (de) | 1976-11-25 |
Family
ID=24308475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762620897 Ceased DE2620897A1 (de) | 1975-05-14 | 1976-05-12 | Verfahren zur herstellung von 2-aryl-2h-benzotriazolen |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS6036430B2 (enExample) |
| BE (1) | BE841769A (enExample) |
| BR (1) | BR7603024A (enExample) |
| CH (1) | CH615166A5 (enExample) |
| DE (1) | DE2620897A1 (enExample) |
| ES (1) | ES447874A1 (enExample) |
| FR (1) | FR2311011A1 (enExample) |
| GB (1) | GB1494824A (enExample) |
| NL (1) | NL7605203A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0380840A1 (en) * | 1989-01-31 | 1990-08-08 | Chemipro Kasei Kaisha, Ltd. | Method of preparing 2-phenylbenzotriazoles |
| EP0380839A1 (en) * | 1989-01-31 | 1990-08-08 | Chemipro Kasei Kaisha, Ltd. | Method of preparing 2-phenylbenzotriazoles |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6471862A (en) * | 1987-09-11 | 1989-03-16 | Chemipro Kasei Kaisha Ltd | Production of 2-phenylbenzotriazole |
| DE58907083D1 (de) * | 1988-09-28 | 1994-04-07 | Ciba Geigy | Verfahren zur Herstellung von Benztriazolderivaten. |
| DE59003447D1 (de) * | 1989-09-20 | 1993-12-16 | Ciba Geigy | Verfahren zur Herstellung von Benztriazolen. |
| CN112538055A (zh) * | 2020-12-11 | 2021-03-23 | 西安凯立新材料股份有限公司 | 一种苯并三唑类紫外线吸收剂的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2130322A1 (de) * | 1970-06-19 | 1972-03-16 | Ciba Geigy Ag | Lichtschutzmittel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978074A (en) * | 1973-11-21 | 1976-08-31 | Uniroyal Inc. | Method of making hydroxyarylbenzotriazoles and their N-oxides |
-
1976
- 1976-05-12 CH CH593776A patent/CH615166A5/de not_active IP Right Cessation
- 1976-05-12 DE DE19762620897 patent/DE2620897A1/de not_active Ceased
- 1976-05-13 BE BE166974A patent/BE841769A/xx not_active IP Right Cessation
- 1976-05-13 ES ES447874A patent/ES447874A1/es not_active Expired
- 1976-05-13 GB GB1968676A patent/GB1494824A/en not_active Expired
- 1976-05-13 BR BR7603024A patent/BR7603024A/pt unknown
- 1976-05-13 FR FR7614392A patent/FR2311011A1/fr active Granted
- 1976-05-14 NL NL7605203A patent/NL7605203A/xx not_active Application Discontinuation
- 1976-05-14 JP JP5519676A patent/JPS6036430B2/ja not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2130322A1 (de) * | 1970-06-19 | 1972-03-16 | Ciba Geigy Ag | Lichtschutzmittel |
Non-Patent Citations (2)
| Title |
|---|
| Bull.Soc.Chem.Fr., 8, 1971, 2917 * |
| Houben-Weyl: Methoden der organischen Chemie, Bd. IV/1c, 1980, S. 15 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0380840A1 (en) * | 1989-01-31 | 1990-08-08 | Chemipro Kasei Kaisha, Ltd. | Method of preparing 2-phenylbenzotriazoles |
| EP0380839A1 (en) * | 1989-01-31 | 1990-08-08 | Chemipro Kasei Kaisha, Ltd. | Method of preparing 2-phenylbenzotriazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2311011A1 (fr) | 1976-12-10 |
| BR7603024A (pt) | 1977-05-31 |
| JPS51138677A (en) | 1976-11-30 |
| CH615166A5 (en) | 1980-01-15 |
| ES447874A1 (es) | 1977-07-16 |
| GB1494824A (en) | 1977-12-14 |
| NL7605203A (nl) | 1976-11-16 |
| BE841769A (fr) | 1976-11-16 |
| FR2311011B1 (enExample) | 1978-05-19 |
| JPS6036430B2 (ja) | 1985-08-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4230867A (en) | Process for the production of 2-aryl-2H-benzotriazoles | |
| EP0363318B1 (de) | Verfahren zur Herstellung von Benztriazolderivaten | |
| DE2620897A1 (de) | Verfahren zur herstellung von 2-aryl-2h-benzotriazolen | |
| US4141903A (en) | Process for the production of 2-aryl-2H-benzotriazoles | |
| DE2620970A1 (de) | Verfahren zur herstellung von 2-aryl-2h-benzotriazolen | |
| US4219480A (en) | Process for the production of 2-aryl-2H-benzotriazoles | |
| DE2454889A1 (de) | Verfahren zur herstellung von 2(2-hydroxyphenyl)-benztriazolen | |
| EP0457730B1 (de) | Verfahren zur Herstellung von Alkylydroxyanilino-triazinthioderivaten | |
| DE2165554A1 (de) | Verfahren zur herstellung von 1,2,4triazin-5-on-derivaten | |
| DE2621006A1 (de) | Verfahren zur herstellung von 2-aryl-2h-benzotriazolen | |
| DE68922714T2 (de) | Verfahren zur Herstellung von 2-Phenylbenzotriazolen. | |
| DE2609530C2 (de) | Verfahren zur Herstellung von Hydrazobenzolen | |
| DE2620896A1 (de) | Verfahren zur herstellung von 2-aryl-2h-benzotriazolen | |
| DE3017542A1 (de) | Verfahren zur herstellung von 2-trifluormethylanilin | |
| DE3035792C2 (de) | Verfahren zur Herstellung von 2-Oxodihydrobenzo[d][1,3]-oxazinen und deren Verwendung zur Herstellung von o-Aminobenzylalkoholen | |
| EP0034836B1 (de) | Verfahren zum Herstellen von Nitroazobenzolen | |
| CA1154778A (en) | Process for the production of 2-aryl-2h- benzotriazoles | |
| CA1154777A (en) | Process for the production of 2-aryl-2h- benzotriazoles | |
| DE1229537B (de) | Verfahren zur Herstellung von 3, 4-Dihydro-1, 3-benzoxazinonen-(2) | |
| CA1154779A (en) | Process for the production of 2-aryl-2h- benzotriazoles | |
| CH401079A (de) | Verfahren zur Herstellung einer Aminobenzolverbindung mit mindestens einer metasubstituierten Methylensulfonyläthanolgruppe | |
| AT248441B (de) | Verfahren zur Herstellung von neuen Salicylsäurederivaten | |
| AT220149B (de) | Verfahren zur Herstellung von Aryloxymethyl-2-oxazolidinonen | |
| DE2140787C3 (de) | Verfahren zur Herstellung von aromatischen Diaminen | |
| DE2532124B2 (de) | Verfahren zur Herstellung von 4-Amino-morpholin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |