JPS6036432B2 - ２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法 - Google Patents

２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法

Info

Publication number: JPS6036432B2
Authority: JP; Japan
Prior art keywords: hydroxy; benzotriazole; alkaline; catalyst; aryl
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

JP5519876A

Other languages

English (en)

Japanese (ja)

Other versions

JPS51138679A (en

Inventor

ハワード・エル・ホワイト

カシミール・ヴイ・クロリウスキー

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.)

Novartis AG

Original Assignee

Ciba Geigy AG

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

1976-05-14

Publication date

1985-08-20

1976-05-14 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1976-11-30 Publication of JPS51138679A publication Critical patent/JPS51138679A/ja

1985-08-20 Publication of JPS6036432B2 publication Critical patent/JPS6036432B2/ja

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 20
239000003054 catalyst Substances 0.000 claims description 78
238000000034 method Methods 0.000 claims description 69
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 58
239000000047 product Substances 0.000 claims description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
-1 alicyclic amine Chemical class 0.000 claims description 49
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
150000001412 amines Chemical class 0.000 claims description 41
238000006722 reduction reaction Methods 0.000 claims description 41
238000006243 chemical reaction Methods 0.000 claims description 39
229910000564 Raney nickel Inorganic materials 0.000 claims description 38
238000005984 hydrogenation reaction Methods 0.000 claims description 37
239000003960 organic solvent Substances 0.000 claims description 28
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 17
150000004707 phenolate Chemical class 0.000 claims description 16
230000008569 process Effects 0.000 claims description 15
239000012964 benzotriazole Substances 0.000 claims description 14
238000001914 filtration Methods 0.000 claims description 14
229910052759 nickel Inorganic materials 0.000 claims description 14
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 13
239000012043 crude product Substances 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
239000002270 dispersing agent Substances 0.000 claims description 12
229930195733 hydrocarbon Natural products 0.000 claims description 11
150000002430 hydrocarbons Chemical class 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
239000004215 Carbon black (E152) Substances 0.000 claims description 9
238000006476 reductive cyclization reaction Methods 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 6
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
238000007796 conventional method Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
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 claims description 4
239000000126 substance Substances 0.000 claims description 4
229910052799 carbon Inorganic materials 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
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
239000011651 chromium Substances 0.000 claims description 2
229910052750 molybdenum Inorganic materials 0.000 claims description 2
239000011733 molybdenum Substances 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
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
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
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 55
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 35
230000009467 reduction Effects 0.000 description 35
DSZOTMKIKJOOPG-UHFFFAOYSA-N (2-nitrophenyl)-phenyldiazene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=NC1=CC=CC=C1 DSZOTMKIKJOOPG-UHFFFAOYSA-N 0.000 description 34
239000000543 intermediate Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 21
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 18
229910052500 inorganic mineral Inorganic materials 0.000 description 18
239000011707 mineral Substances 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
239000007868 Raney catalyst Substances 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 14
230000002829 reductive effect Effects 0.000 description 14
239000002253 acid Substances 0.000 description 13
239000002002 slurry Substances 0.000 description 13
239000007864 aqueous solution Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
238000012360 testing method Methods 0.000 description 10
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 9
238000007363 ring formation reaction Methods 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
239000003513 alkali Substances 0.000 description 8
235000015096 spirit Nutrition 0.000 description 8
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 7
235000014113 dietary fatty acids Nutrition 0.000 description 7
239000000194 fatty acid Substances 0.000 description 7
229930195729 fatty acid Natural products 0.000 description 7
239000012535 impurity Substances 0.000 description 7
239000000080 wetting agent Substances 0.000 description 7
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
150000004665 fatty acids Chemical class 0.000 description 6
239000000463 material Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229920001223 polyethylene glycol Polymers 0.000 description 6
239000001593 sorbitan monooleate Substances 0.000 description 6
229940035049 sorbitan monooleate Drugs 0.000 description 6
235000011069 sorbitan monooleate Nutrition 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
238000005406 washing Methods 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
238000007429 general method Methods 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000011260 aqueous acid Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000008096 xylene Substances 0.000 description 3
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HWKBCQRRNIJFFS-UHFFFAOYSA-N 1-nitro-6-phenyldiazenylcyclohexa-2,4-dien-1-ol Chemical compound [O-][N+](=O)C1(O)C=CC=CC1N=NC1=CC=CC=C1 HWKBCQRRNIJFFS-UHFFFAOYSA-N 0.000 description 2
GUTIRSJPHXTNAH-UHFFFAOYSA-N 2-[(2-nitrophenyl)diazenyl]-4,6-dipentylphenol Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)N=NC1=C(C(=CC(=C1)CCCCC)CCCCC)O GUTIRSJPHXTNAH-UHFFFAOYSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
230000002378 acidificating effect Effects 0.000 description 2
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
229960003237 betaine Drugs 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000003093 cationic surfactant Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
238000003912 environmental pollution Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
159000000011 group IA salts Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
QVRVXSZKCXFBTE-UHFFFAOYSA-N n-[4-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-2-(2-fluoroethoxy)-5-methylbenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCCCNC(=O)C1=CC(C)=CC=C1OCCF QVRVXSZKCXFBTE-UHFFFAOYSA-N 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
150000003139 primary aliphatic amines Chemical class 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000005619 secondary aliphatic amines Chemical class 0.000 description 2
238000000926 separation method 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
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
150000003852 triazoles Chemical class 0.000 description 2
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
IDLWSCOEZKCGDN-UHFFFAOYSA-N (1-nitrocyclohexa-2,4-dien-1-yl)hydrazine Chemical compound NNC1(CC=CC=C1)[N+](=O)[O-] IDLWSCOEZKCGDN-UHFFFAOYSA-N 0.000 description 1
VCCPFNMAICRKLQ-UHFFFAOYSA-N (3-methylphenyl)-phenyldiazene Chemical group CC1=CC=CC(N=NC=2C=CC=CC=2)=C1 VCCPFNMAICRKLQ-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-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
YLIVWUAQJLBXKC-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)-1-nitro-6-phenyldiazenylcyclohexa-2,4-dien-1-ol Chemical group [N+](=O)([O-])C1(C(C=C(C=C1C(C)(C)CC)C(C)(C)CC)N=NC1=CC=CC=C1)O YLIVWUAQJLBXKC-UHFFFAOYSA-N 0.000 description 1
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 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
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 description 1
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 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
TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
GTLMTHAWEBRMGI-UHFFFAOYSA-N 2-cyclohexyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C2CCCCC2)=C1 GTLMTHAWEBRMGI-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 1
MLBVGIVHTILOIG-UHFFFAOYSA-N 4-methyl-1-nitro-6-phenyldiazenylcyclohexa-2,4-dien-1-ol Chemical compound [O-][N+](=O)C1(O)C=CC(C)=CC1N=NC1=CC=CC=C1 MLBVGIVHTILOIG-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
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
241001279686 Allium moly Species 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
241000252233 Cyprinus carpio Species 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
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound 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
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
229930006000 Sucrose Natural products 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-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
239000002250 absorbent Substances 0.000 description 1
230000032900 absorption of visible light Effects 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000007513 acids Chemical class 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
150000004996 alkyl benzenes 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
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000002280 amphoteric surfactant Substances 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
238000005282 brightening Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000002826 coolant 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
229930003836 cresol Natural products 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000010408 film Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
239000013462 industrial intermediate Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229940102253 isopropanolamine Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-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
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000004987 o-phenylenediamines Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
229940117986 sulfobetaine Drugs 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000010409 thin film Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
238000013022 venting Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
229910052726 zirconium Inorganic materials 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)
Catalysts (AREA)
Springs (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP5519876A 1975-05-14 1976-05-14 ２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法 Expired JPS6036432B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US57738675A	1975-05-14	1975-05-14
US577386		1975-05-14

Publications (2)

Publication Number	Publication Date
JPS51138679A JPS51138679A (en)	1976-11-30
JPS6036432B2 true JPS6036432B2 (ja)	1985-08-20

Family

ID=24308487

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5519876A Expired JPS6036432B2 (ja)	1975-05-14	1976-05-14	２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法

Country Status (9)

Country	Link
JP (1)	JPS6036432B2 (fr)
BE (1)	BE841771A (fr)
BR (1)	BR7603023A (fr)
CH (1)	CH615167A5 (fr)
DE (1)	DE2620896A1 (fr)
ES (2)	ES447876A1 (fr)
FR (1)	FR2311013A1 (fr)
GB (1)	GB1494826A (fr)
NL (1)	NL7605204A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0718087B2 (ja) *	1982-12-07	1995-03-01	コモンウエルス・サイエンテイフィック・アンド・インダストリアル・リサーチ・オーガニゼーション	ウール，染色されたウール，絹，ナイロンまたはこれらの混紡を光劣化から保護する方法および光劣化から保護されたウール，染色されたウール，絹，ナイロンまたはこれらの混紡
JPS6471862A (en) *	1987-09-11	1989-03-16	Chemipro Kasei Kaisha Ltd	Production of 2-phenylbenzotriazole
JPH02202879A (ja) *	1989-01-31	1990-08-10	Kemipuro Kasei Kk	２―フェニルベンゾトリアゾール類の製造法
JPH02202880A (ja) *	1989-01-31	1990-08-10	Kemipuro Kasei Kk	２―フェニルベンゾトリアゾール類の製造法
US5675015A (en) *	1996-03-07	1997-10-07	Eastman Kodak Company	Process for the preparation of benzotriazole derivatives
JP6131400B2 (ja) *	2013-01-29	2017-05-24	シプロ化成株式会社	ベンゾトリアゾール誘導体化合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH529815A (de) *	1970-06-19	1972-10-31	Ciba Geigy Ag	Verwendung von 2-(2'Hydroxyphenyl)-benztriazolverbindungen als Lichtschutzmittel
US3978074A (en) *	1973-11-21	1976-08-31	Uniroyal Inc.	Method of making hydroxyarylbenzotriazoles and their N-oxides

1976
- 1976-05-12 DE DE19762620896 patent/DE2620896A1/de not_active Ceased
- 1976-05-12 CH CH593976A patent/CH615167A5/de not_active IP Right Cessation
- 1976-05-13 BR BR7603023A patent/BR7603023A/pt unknown
- 1976-05-13 BE BE166976A patent/BE841771A/fr not_active IP Right Cessation
- 1976-05-13 GB GB1968876A patent/GB1494826A/en not_active Expired
- 1976-05-13 ES ES447876A patent/ES447876A1/es not_active Expired
- 1976-05-13 FR FR7614394A patent/FR2311013A1/fr active Granted
- 1976-05-13 ES ES447875A patent/ES447875A1/es not_active Expired
- 1976-05-14 JP JP5519876A patent/JPS6036432B2/ja not_active Expired
- 1976-05-14 NL NL7605204A patent/NL7605204A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2311013B1 (fr)	1978-05-19
FR2311013A1 (fr)	1976-12-10
CH615167A5 (en)	1980-01-15
ES447875A1 (es)	1977-07-16
BE841771A (fr)	1976-11-16
NL7605204A (nl)	1976-11-16
GB1494826A (en)	1977-12-14
JPS51138679A (en)	1976-11-30
DE2620896A1 (de)	1976-12-02
ES447876A1 (es)	1977-07-16
BR7603023A (pt)	1977-05-31

Publication	Publication Date	Title
US4230867A (en)	1980-10-28	Process for the production of 2-aryl-2H-benzotriazoles
US7799930B2 (en)	2010-09-21	1-alkyl-3-aminoindazoles
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
JPS6036432B2 (ja)	1985-08-20	２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法
CA2309461A1 (fr)	1999-05-14	Procede de preparation de derives de thiazolidinedione
JPS6036431B2 (ja)	1985-08-20	２‐アリール‐２ｈ‐ベンゾトリアゾールの製造法
US5571924A (en)	1996-11-05	Process for the preparation of 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
US4246196A (en)	1981-01-20	Diaminophenyl ureas
US5104992A (en)	1992-04-14	Method of preparing 2-phenyl benezothriazoles
JP4162274B2 (ja)	2008-10-08	ビス（２−ヒドロキシフェニル−３−ベンゾトリアゾール）メタン類の製造方法
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
EP0793659A1 (fr)	1997-09-10	Procede pour la preparation de 5-hydroxymethylthiazole
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
CA1073463A (fr)	1980-03-11	Procede pour la production de 2-aryl-2h-benzotriazoles
CA1241659A (fr)	1988-09-06	Methode de preparation de 2-phenylbenzotriazole
US4216340A (en)	1980-08-05	Preparation of 5-(2,4-difluorophenyl)salicylic acid and derivatives
CA1154779A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
US4118501A (en)	1978-10-03	Thiazolidine derivatives
US4138404A (en)	1979-02-06	Process for the preparation of oxadiazolines
EP0380839A1 (fr)	1990-08-08	Procédé de préparation de phényl-2 benzotriazoles
US3293260A (en)	1966-12-20	1-substituted cycloheptimidazol-2(1h)-one compounds
CA1154777A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles