CH618690A5 - - Google Patents

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Publication number: CH618690A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; tert; chlorine; hydrogen; alkyl
Prior art date: 1974-11-25

Application number

CH1512375A

Other languages

German (de)

English (en)

Inventor

Howard L White

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.)

1974-11-25

Filing date

1975-11-21

Publication date

1980-08-15

1975-11-21 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-08-15 Publication of CH618690A5 publication Critical patent/CH618690A5/de

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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 85
DSZOTMKIKJOOPG-UHFFFAOYSA-N (2-nitrophenyl)-phenyldiazene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=NC1=CC=CC=C1 DSZOTMKIKJOOPG-UHFFFAOYSA-N 0.000 claims description 61
125000004432 carbon atom Chemical group C* 0.000 claims description 60
239000003513 alkali Substances 0.000 claims description 45
229910052742 iron Inorganic materials 0.000 claims description 41
238000000034 method Methods 0.000 claims description 40
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 39
-1 carboxyethyl Chemical group 0.000 claims description 37
239000011701 zinc Substances 0.000 claims description 37
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 36
239000000460 chlorine Substances 0.000 claims description 31
229910052801 chlorine Inorganic materials 0.000 claims description 31
230000009467 reduction Effects 0.000 claims description 31
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
229910052725 zinc Inorganic materials 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
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 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
125000000753 cycloalkyl 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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
239000012454 non-polar solvent Substances 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
229910006069 SO3H Inorganic materials 0.000 claims 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 claims 1
239000003921 oil Substances 0.000 claims 1
239000000047 product Substances 0.000 description 55
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
239000012071 phase Substances 0.000 description 31
239000006227 byproduct Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 12
150000001204 N-oxides Chemical class 0.000 description 10
239000012535 impurity Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
235000015096 spirit Nutrition 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
230000035484 reaction time Effects 0.000 description 8
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 7
239000012452 mother liquor Substances 0.000 description 6
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 5
238000011109 contamination Methods 0.000 description 5
MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000002955 isolation Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
TUHVRBYGFUJORQ-UHFFFAOYSA-N 2-amino-4,6-bis(2-methylbutan-2-yl)phenol;hydrochloride Chemical compound Cl.CCC(C)(C)C1=CC(N)=C(O)C(C(C)(C)CC)=C1 TUHVRBYGFUJORQ-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical compound NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 3
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 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
239000006096 absorbing agent Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
230000007613 environmental effect Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
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
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 description 2
NLWDAUDWBLSJGK-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butyl-6-methylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O NLWDAUDWBLSJGK-UHFFFAOYSA-N 0.000 description 2
WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 2
QUDZAFKCASPJLX-UHFFFAOYSA-N 2-aminophenol;hydron;chloride Chemical compound Cl.NC1=CC=CC=C1O QUDZAFKCASPJLX-UHFFFAOYSA-N 0.000 description 2
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 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
QFTTTWKZLOQAFF-UHFFFAOYSA-N 3-octoxyphenol Chemical compound CCCCCCCCOC1=CC=CC(O)=C1 QFTTTWKZLOQAFF-UHFFFAOYSA-N 0.000 description 2
KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 2
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 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 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000003849 aromatic solvent Substances 0.000 description 2
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
239000000975 dye Substances 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000010408 film Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
FZZMDWLROBNSRG-UHFFFAOYSA-N n-phenyliminonitramide Chemical compound [O-][N+](=O)N=NC1=CC=CC=C1 FZZMDWLROBNSRG-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
RIKCMEDSBFQFAL-UHFFFAOYSA-N octyl 4-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(O)C=C1 RIKCMEDSBFQFAL-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000011946 reduction process Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
150000003613 toluenes Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
DNYCICZKXQGHBJ-UHFFFAOYSA-N 2,4-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(C(C)(C)CC(C)(C)C)=C1 DNYCICZKXQGHBJ-UHFFFAOYSA-N 0.000 description 1
WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 1
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-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
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
AYTSDBGAHOKDHJ-UHFFFAOYSA-N 2-nitrobenzenediazonium Chemical class [O-][N+](=O)C1=CC=CC=C1[N+]#N AYTSDBGAHOKDHJ-UHFFFAOYSA-N 0.000 description 1
IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
GGLOSSFVOIXPQY-UHFFFAOYSA-N 2-tert-butyl-6-[(5-chloro-2-nitrophenyl)diazenyl]-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(N=NC=2C(=CC=C(Cl)C=2)[N+]([O-])=O)=C1O GGLOSSFVOIXPQY-UHFFFAOYSA-N 0.000 description 1
WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
ZPAIMGRPEHRDLH-UHFFFAOYSA-N 3-(4-hydroxy-3-methylphenyl)propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC=C1O ZPAIMGRPEHRDLH-UHFFFAOYSA-N 0.000 description 1
YHMYLDCYUHBSNP-UHFFFAOYSA-N 4-butan-2-yl-2-tert-butylphenol Chemical compound CCC(C)C1=CC=C(O)C(C(C)(C)C)=C1 YHMYLDCYUHBSNP-UHFFFAOYSA-N 0.000 description 1
PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
ZUTYZAFDFLLILI-UHFFFAOYSA-N 4-sec-Butylphenol Chemical compound CCC(C)C1=CC=C(O)C=C1 ZUTYZAFDFLLILI-UHFFFAOYSA-N 0.000 description 1
ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
DCCUXLZKDYHPIO-UHFFFAOYSA-N 4-tert-butyl-2-[(2-nitrophenyl)diazenyl]phenol Chemical compound OC1=C(C=C(C=C1)C(C)(C)C)N=NC1=C(C=CC=C1)[N+](=O)[O-] DCCUXLZKDYHPIO-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-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
XEEYBQQBJWHFJM-BJUDXGSMSA-N Iron-55 Chemical compound [55Fe] XEEYBQQBJWHFJM-BJUDXGSMSA-N 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 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 description 1
KMUFWAPHDZTCMI-UHFFFAOYSA-N butyl 4-amino-3-nitrobenzoate Chemical compound CCCCOC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 KMUFWAPHDZTCMI-UHFFFAOYSA-N 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
230000015556 catabolic process Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002505 iron Chemical class 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
JQJCSZOEVBFDKO-UHFFFAOYSA-N lead zinc Chemical compound [Zn].[Pb] JQJCSZOEVBFDKO-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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
150000002894 organic compounds Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000010409 thin film Substances 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1512375A 1974-11-25 1975-11-21 CH618690A5 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US52717974A	1974-11-25	1974-11-25
US05/622,572 US4041044A (en)	1974-11-25	1975-10-15	Process for the production of 2-aryl-2H-benzotriazoles

Publications (1)

Publication Number	Publication Date
CH618690A5 true CH618690A5 (fr)	1980-08-15

Family

ID=27062349

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1512375A CH618690A5 (fr)	1974-11-25	1975-11-21

Country Status (5)

Country	Link
US (1)	US4041044A (fr)
CA (1)	CA1062266A (fr)
CH (1)	CH618690A5 (fr)
DE (1)	DE2551853A1 (fr)
GB (1)	GB1520798A (fr)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4219480A (en) *	1977-09-20	1980-08-26	Ciba-Geigy Corporation	Process for the production of 2-aryl-2H-benzotriazoles
US4278589A (en) *	1978-06-26	1981-07-14	Ciba-Geigy Corporation	2-[2-Hydroxy-3,5-di-(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole and stabilized compositions
US4226763A (en) *	1978-06-26	1980-10-07	Ciba-Geigy Corporation	2-[2-Hydroxy-3,5-di-(.alpha.,α-dimethylbenzyl)-phenyl]-2H-benzotriazole and stabilized compositions
US4275004A (en) *	1978-06-26	1981-06-23	Ciba-Geigy Corporation	High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes
US4283327A (en) *	1979-01-25	1981-08-11	Ciba-Geigy Corporation	2-(2-Hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole stabilized compositions
US4477614A (en) *	1979-01-25	1984-10-16	Ciba-Geigy Corporation	2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole stabilized compositions
EP0015230B1 (fr) *	1979-01-25	1983-02-23	Ciba-Geigy Ag	Polymère stabilisé contenant 2-(2-hydroxy,3,5-di-tert-octylphényl)-2H-benzotriazol comme stabilisateur de lumière
US4278590A (en) *	1979-08-20	1981-07-14	Ciba-Geigy Corporation	2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-Benzotriazole and stabilized compositions
US4315848A (en) *	1979-05-10	1982-02-16	Ciba-Geigy Corporation	2-[2-Hydroxy-3,5-di-(α,α-dimethylbenzyl)-phenyl]-2H-benzotriazole and stabilized compositions
US4347180A (en) *	1979-05-16	1982-08-31	Ciba-Geigy Corporation	High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes
US4383863A (en) *	1979-12-17	1983-05-17	Ciba-Geigy Corporation	2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole in stabilized photographic compositions
EP0031302A3 (fr) *	1979-12-21	1981-07-22	Ciba-Geigy Ag	Benzotriazoles absorbant les UV, procédé pour leur préparation et mélanges stabilisés
US4447511A (en) *	1981-03-06	1984-05-08	Ciba-Geigy Corporation	2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole in stabilized photographic compositions
CH647514A5 (de) *	1981-03-06	1985-01-31	Sandoz Ag	Verfahren zur herstellung von kondensierten triazolen.
US4709041A (en) *	1981-11-16	1987-11-24	Polaroid Corporation	2-(formylphenyl) benzotriazole intermediates
EP0130938B1 (fr) *	1983-06-01	1989-02-15	Ciba-Geigy Ag	Procédé de préparation de 2-arylbenzotriazoles
US5206378A (en) *	1987-08-12	1993-04-27	Elf Atochem North America, Inc.	Hydrazido functionalized 2-(2-hydroxyphenyl)-2h-benzotriazoles
US4981914A (en) *	1987-08-12	1991-01-01	Atochem North America, Inc.	Polymer bound UV stabilizers
US5096977A (en) *	1987-08-12	1992-03-17	Atochem North America, Inc.	Process for preparing polymer bound UV stabilizers
US4859759A (en) *	1988-04-14	1989-08-22	Kimberly-Clark Corporation	Siloxane containing benzotriazolyl/tetraalkylpiperidyl substituent
BR8907374A (pt) *	1989-02-13	1991-04-23	Atochem North America	Composto quimico
EP0424316A3 (en) *	1989-10-19	1991-09-25	Ciba-Geigy Ag	Purification of 2-aryl-2h-benzotriazoles
US5739348A (en) *	1996-10-23	1998-04-14	Eastman Kodak Company	Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process
US5683861A (en) *	1996-10-23	1997-11-04	Eastman Kodak Company	Benzotriazole-based UV absorbers and photographic elements containing them
EP0975421B1 (fr)	1997-04-15	2014-06-18	Basf Se	Preparation d'agents stabilisants peu pulverulents
US6251173B1 (en)	1999-10-29	2001-06-26	Lexmark International, Inc.	Ink compositions containing ultraviolet absorbers
WO2003104341A1 (fr) *	2001-05-10	2003-12-18	Lexmark International, Inc.	Compositions d'encres contenant des absorbeurs d'uv
WO2003011983A2 (fr) *	2001-08-01	2003-02-13	Lexmark International, Inc.	Compositions d'encre contenant des agents absorbant l'ultraviolet
CN110396070A (zh) *	2019-09-11	2019-11-01	广东工业大学	一种苯并三氮唑类紫外吸收剂的制备方法

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Publication number	Priority date	Publication date	Assignee	Title
US2501188A (en) *	1947-10-22	1950-03-21	American Cyanamid Co	2-(2'-methyl-4'-amino-5'-methoxyphenyl)-2, 1, 3 benzotriazole
DE1185610B (de) *	1956-12-14	1965-01-21	Geigy Ag J R	Verwendung von 2-Phenylbenzotriazol-verbindungen zum Schuetzen von organischen Stoffen gegen ultraviolette Strahlung
US3230194A (en) *	1961-12-22	1966-01-18	American Cyanamid Co	2-(2'-hydroxy-5'-tertiary-octylphenyl)-benzotriazole and polyolefins stabilized therewith
US3773751A (en) *	1969-09-08	1973-11-20	American Cyanamid Co	Synthesis of nitroaromatic-azophenols
CH529815A (de) *	1970-06-19	1972-10-31	Ciba Geigy Ag	Verwendung von 2-(2'Hydroxyphenyl)-benztriazolverbindungen als Lichtschutzmittel

1975
- 1975-10-15 US US05/622,572 patent/US4041044A/en not_active Expired - Lifetime
- 1975-11-19 DE DE19752551853 patent/DE2551853A1/de not_active Ceased
- 1975-11-21 GB GB47940/75A patent/GB1520798A/en not_active Expired
- 1975-11-21 CH CH1512375A patent/CH618690A5/de not_active IP Right Cessation
- 1975-11-24 CA CA240,240A patent/CA1062266A/fr not_active Expired

Also Published As

Publication number	Publication date
US4041044A (en)	1977-08-09
CA1062266A (fr)	1979-09-11
GB1520798A (en)	1978-08-09
DE2551853A1 (de)	1976-05-26

Legal Events

Date	Code	Title	Description
1988-07-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH618690A5 (fr)	1980-08-15
DE2855764C2 (fr)	1988-06-16
EP0574667A1 (fr)	1993-12-22	Procédé pour la préparation des dérivés 4-substitués de 2,2,6,6-tétraméthylpipéridine-N-oxyls
DE2500265C2 (de)	1985-03-28	Sulfone von Acrylsäurederivaten, Verfahren zu deren Herstellung und diese Verbindungen enthaltendes mikrobizides Mittel
EP0419412B1 (fr)	1993-11-10	Procédé pour la préparation de benzotriazoles
EP0031302A2 (fr)	1981-07-01	Benzotriazoles absorbant les UV, procédé pour leur préparation et mélanges stabilisés
DE2339240A1 (de)	1974-02-14	Metallextraktionsverfahren
DE2835846A1 (de)	1979-02-22	Verfahren zur herstellung von 2-aryl-2h-benzotriazolen
DE1076696B (de)	1960-03-03	Verfahren zur Herstellung fluorhaltiger Derivate des 1, 3, 5-Triazins
DE4318069C1 (de)	1994-03-31	Verfahren zur Herstellung von 5-Brom-6-methoxy-1-naphthoesäuremethylester
DE2247508A1 (de)	1973-04-05	Chelate zur bekaempfung von metallmangelerscheinungen bei pflanzen
CH615165A5 (en)	1980-01-15	Process for the preparation of 2-aryl-2H-benzotriazoles
DE69707008T2 (de)	2002-05-02	Synthese von jodpropargylcarbamat in wässriger lösung
EP0005172B1 (fr)	1981-04-29	Dérivés de la coumarine et leur application comme azurants pour matériaux organiques de poids moléculaire élevé
DE1266425C2 (de)	1975-11-20	Verfahren zur herstellung von anthrachinon-dispersionsfarbstoffen und deren verwendung
EP0212301A2 (fr)	1987-03-04	Procédé de préparation de 2-aminophényl-thioéthers
DE825413C (de)	1951-12-17	Verfahren zur Herstellung von quartaeren Sulfaten oder Sulfonaten von Pyrimidylaminochinolinen
EP0034836B1 (fr)	1983-07-13	Procédé de préparation de nitroazobenzènes
CH432542A (de)	1967-03-31	Verfahren zur Herstellung neuer Hydrazide
DE19904310A1 (de)	2000-08-03	Verfahren zur Herstellung heterocyclischer Verbindungen
DE2025860A1 (de)	1970-12-03	Verfahren zur Herstellung von hydroxybenzylsubstituierten Isocyanuraten
EP0865433B1 (fr)	2001-10-04	Procede pour reduire la quantite de sous-produits dans le carbendazim par addition d'agents de diazotation
DE3731860A1 (de)	1988-11-10	Verfahren zur herstellung von 2-aryl-2h-benzotriazolen
AT264531B (de)	1968-09-10	Verfahren zur Herstellung von 1,10-Phenanthrolinen
EP0704428A1 (fr)	1996-04-03	Procédé pour la préparation de Salcomin