DD284227A5 - Verfahren zur herstellung von benztriazolderivaten - Google Patents

Verfahren zur herstellung von benztriazolderivaten Download PDF

Info

Publication number: DD284227A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; butylamine; hydrogen; formula; phenyl
Prior art date: 1988-09-28

Application number

DD89332979A

Other languages

German (de)

English (en)

Inventor

Helmut Prestel

Klaus Mueller

Original Assignee

��`��@��k��

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.)

1988-09-28

Filing date

1989-09-26

Publication date

1990-11-07

1989-09-26 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1990-11-07 Publication of DD284227A5 publication Critical patent/DD284227A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 38
238000002360 preparation method Methods 0.000 title claims abstract description 12
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 3
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 43
239000003054 catalyst Substances 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
239000001257 hydrogen Substances 0.000 claims abstract description 27
150000001412 amines Chemical class 0.000 claims abstract description 24
150000001875 compounds Chemical class 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical group 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 7
238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 5
239000002904 solvent Substances 0.000 claims description 24
-1 azo compound Chemical class 0.000 claims description 22
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 20
239000008096 xylene Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 18
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 12
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 8
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 7
FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 7
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
KDSNLYIMUZNERS-UHFFFAOYSA-N isobutyl amine Natural products CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 5
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 3
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
229910052697 platinum Inorganic materials 0.000 abstract description 4
230000003197 catalytic effect Effects 0.000 abstract description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000000047 product Substances 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000002585 base Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
150000001565 benzotriazoles Chemical class 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000005695 dehalogenation reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003245 coal Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910000510 noble metal Inorganic materials 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
MIMONXWGQIJLGP-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(5-chloro-2-nitrophenyl)diazenyl]phenol Chemical compound [N+](=O)([O-])C1=C(C=C(C=C1)Cl)N=NC1=C(C(=CC(=C1)C(C)(C)C)C(C)(C)C)O MIMONXWGQIJLGP-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000005263 alkylenediamine group Chemical group 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000012964 benzotriazole Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000004611 light stabiliser Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
238000004904 shortening Methods 0.000 description 2
CFNRNHFKQPOFMH-UHFFFAOYSA-N (2-methylphenyl)-phenyldiazene Chemical compound CC1=CC=CC=C1N=NC1=CC=CC=C1 CFNRNHFKQPOFMH-UHFFFAOYSA-N 0.000 description 1
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 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
AGFWFPOJMXUXTJ-UHFFFAOYSA-N 2-(2h-benzotriazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC2=NNN=C12 AGFWFPOJMXUXTJ-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-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
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
KFJDQPJLANOOOB-UHFFFAOYSA-N 2h-benzotriazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=NNN=C12 KFJDQPJLANOOOB-UHFFFAOYSA-N 0.000 description 1
RAVQOTOHZRSUCO-UHFFFAOYSA-N 3-[3-tert-butyl-5-[(5-chloro-2-nitrophenyl)diazenyl]-4-hydroxyphenyl]propanoic acid Chemical compound [N+](=O)([O-])C1=C(C=C(C=C1)Cl)N=NC1=C(C(=CC(=C1)CCC(=O)O)C(C)(C)C)O RAVQOTOHZRSUCO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 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
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 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
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000000976 ink Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000002609 medium Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
VRBLLGLKTUGCSG-UHFFFAOYSA-N methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O VRBLLGLKTUGCSG-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000003415 peat Substances 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006476 reductive cyclization reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000004032 superbase Substances 0.000 description 1
150000007525 superbases Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

DD89332979A 1988-09-28 1989-09-26 Verfahren zur herstellung von benztriazolderivaten DD284227A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH359488		1988-09-28

Publications (1)

Publication Number	Publication Date
DD284227A5 true DD284227A5 (de)	1990-11-07

Family

ID=4259354

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89332979A DD284227A5 (de)	1988-09-28	1989-09-26	Verfahren zur herstellung von benztriazolderivaten

Country Status (12)

Country	Link
US (1)	US4999433A (fr)
EP (1)	EP0363318B1 (fr)
JP (1)	JP2824589B2 (fr)
KR (1)	KR0121756B1 (fr)
CN (1)	CN1031341C (fr)
BR (1)	BR8904898A (fr)
CA (1)	CA1337939C (fr)
DD (1)	DD284227A5 (fr)
DE (1)	DE58907083D1 (fr)
ES (1)	ES2062096T3 (fr)
MX (1)	MX169919B (fr)
RU (1)	RU2002742C1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5187289A (en) *	1989-01-31	1993-02-16	Chemipro Kasei Kaisha, Ltd.	Method of preparing 2-phenyl benzotriazoles
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
DE59003447D1 (de) *	1989-09-20	1993-12-16	Ciba Geigy	Verfahren zur Herstellung von Benztriazolen.
RU2126393C1 (ru) *	1992-02-05	1999-02-20	Циба Спешиалти Кемикэлс Холдинг Инк.	Замешенные бензотриазолы и стабилизированная композиция и покрывная система, их содержания
JP2705895B2 (ja) *	1993-12-28	1998-01-28	大阪精化工業株式会社	繊維材料用処理剤
US5670654A (en) *	1995-06-29	1997-09-23	Eastman Kodak Company	Method of synthesizing 2-(2'-hydroxyphenyl) benzotriazole compounds
US5571924A (en) *	1995-07-12	1996-11-05	Ciba-Geigy Corporation	Process for the preparation of benzotriazoles
US5675015A (en) *	1996-03-07	1997-10-07	Eastman Kodak Company	Process for the preparation of benzotriazole derivatives
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
EP0975421B1 (fr)	1997-04-15	2014-06-18	Basf Se	Preparation d'agents stabilisants peu pulverulents
KR100454807B1 (ko) *	1997-05-13	2004-12-23	삼성종합화학주식회사	벤조트리아졸계자외선흡수제의제조방법
US6251173B1 (en) *	1999-10-29	2001-06-26	Lexmark International, Inc.	Ink compositions containing ultraviolet absorbers
US6451887B1 (en) *	2000-08-03	2002-09-17	Ciba Specialty Chemicals Corporation	Benzotriazoles containing α-cumyl groups substituted by heteroatoms and compositions stabilized therewith
US6649770B1 (en)	2000-11-27	2003-11-18	Ciba Specialty Chemicals Corporation	Substituted 5-aryl-2-(2-hydroxyphenyl)-2H-benzotriazole UV absorbers, compositions stabilized therewith and process for preparation thereof
DE60107874T2 (de) *	2000-11-27	2005-05-19	Ciba Speciality Chemicals Holding Inc.	Substituierte 5-aryl- und 5-heteroaryl-2-(2-hydroxyphenyl)-2h-benzotriazolderivate als uv-absorbierende substanzen
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

Family Cites Families (8)

* Cited by examiner, † Cited by third party
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
CH615166A5 (en) *	1975-05-14	1980-01-15	Ciba Geigy Ag	Process for the preparation of 2-aryl-2H-benzotriazoles
CH615165A5 (en) *	1975-05-14	1980-01-15	Ciba Geigy Ag	Process for the preparation of 2-aryl-2H-benzotriazoles
DE2620970A1 (de) *	1975-05-14	1976-11-25	Ciba Geigy Ag	Verfahren zur herstellung von 2-aryl-2h-benzotriazolen
JPS52113973A (en) *	1976-03-19	1977-09-24	Kawaken Fine Chem Co Ltd	Synthesis of benzotriazole derivatives
JPS52113974A (en) *	1976-03-19	1977-09-24	Kawaken Fine Chem Co Ltd	Synthesis of benzotriazole derivatives
US4219480A (en) *	1977-09-20	1980-08-26	Ciba-Geigy Corporation	Process for the production of 2-aryl-2H-benzotriazoles
US4230867A (en) *	1977-11-25	1980-10-28	Ciba-Geigy Corporation	Process for the production of 2-aryl-2H-benzotriazoles

1989
- 1989-09-25 DE DE89810726T patent/DE58907083D1/de not_active Expired - Fee Related
- 1989-09-25 EP EP89810726A patent/EP0363318B1/fr not_active Expired - Lifetime
- 1989-09-25 ES ES89810726T patent/ES2062096T3/es not_active Expired - Lifetime
- 1989-09-26 CN CN89107469A patent/CN1031341C/zh not_active Expired - Fee Related
- 1989-09-26 CA CA000613306A patent/CA1337939C/fr not_active Expired - Fee Related
- 1989-09-26 US US07/412,370 patent/US4999433A/en not_active Expired - Lifetime
- 1989-09-26 DD DD89332979A patent/DD284227A5/de not_active IP Right Cessation
- 1989-09-27 MX MX017720A patent/MX169919B/es unknown
- 1989-09-27 KR KR1019890014050A patent/KR0121756B1/ko not_active Expired - Fee Related
- 1989-09-27 BR BR898904898A patent/BR8904898A/pt not_active IP Right Cessation
- 1989-09-27 RU SU894742065A patent/RU2002742C1/ru active
- 1989-09-28 JP JP1253715A patent/JP2824589B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CN1031341C (zh)	1996-03-20
BR8904898A (pt)	1990-05-08
DE58907083D1 (de)	1994-04-07
EP0363318A1 (fr)	1990-04-11
JPH02134370A (ja)	1990-05-23
KR0121756B1 (ko)	1997-11-27
CA1337939C (fr)	1996-01-16
EP0363318B1 (fr)	1994-03-02
RU2002742C1 (ru)	1993-11-15
ES2062096T3 (es)	1994-12-16
CN1041590A (zh)	1990-04-25
MX169919B (es)	1993-07-30
US4999433A (en)	1991-03-12
KR900004702A (ko)	1990-04-12
JP2824589B2 (ja)	1998-11-11

Legal Events

Date	Code	Title	Description
1995-06-22	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD284227A5 (de)	1990-11-07	Verfahren zur herstellung von benztriazolderivaten
DE2441650C3 (de)	1979-05-23	Verfahren zur Herstellung von halogenierten aromatischen primären Aminen
DE2549900C3 (de)	1981-02-05	Verfahren zur Herstellung chlorierter aromatischer Amine
DE2855764C2 (fr)	1988-06-16
DE1793658B2 (de)	1974-01-03	N1N1N1, Nr-Tetrakis-(p-phenyl) p-phenylendiamine und -benzidine. Ausscheidung aus: 1693218
EP0419412B1 (fr)	1993-11-10	Procédé pour la préparation de benzotriazoles
DE1768999C3 (de)	1978-04-27	Verfahren zur Herstellung von Nitro-p-phenylendiaminen
DE2615079A1 (de)	1976-10-28	Verfahren zur katalytischen reduktion von halogensubstituierten mononitroaromatischen kohlenwasserstoffen
DE2835846A1 (de)	1979-02-22	Verfahren zur herstellung von 2-aryl-2h-benzotriazolen
DE2620970C2 (fr)	1989-06-29
DE3725659A1 (de)	1989-02-16	Verfahren zur herstellung von mit fluor und gegebenenfalls zusaetzlich chlor substituierten benzotrifluoriden und neue benzotrifluoride
DE68922714T2 (de)	1995-09-14	Verfahren zur Herstellung von 2-Phenylbenzotriazolen.
CH615165A5 (en)	1980-01-15	Process for the preparation of 2-aryl-2H-benzotriazoles
EP0142788A1 (fr)	1985-05-29	Procédé de préparation de 3-acétylamino-aniline pur
DD242640A5 (de)	1987-02-04	Verfahren zur herstellung von p-aminophenolen durch elektrolyse
CH615166A5 (en)	1980-01-15	Process for the preparation of 2-aryl-2H-benzotriazoles
DE3504073C2 (fr)	1987-09-17
DD201894A5 (de)	1983-08-17	Verfahren zur herstellung von 2-(4-aminophenyl)5-aminobenzimidazol und seinen substituierten derivaten
EP0063298B1 (fr)	1984-02-22	Procédé de préparation de 1-alcoyl-amino-anthraquinones
WO1991000262A1 (fr)	1991-01-10	Procede de production de n-alkylanilines halogenes
DE2736228A1 (de)	1978-02-16	Reduktion und reduktive alkylierung von p-nitrosoarylaminen mit platinmetallsulfid-katalysatoren
DE2355917C3 (de)	1983-04-21	1,3-Bis(β-äthylhexyl)-5-nitro-5-methyl-hexahydropyrimidin-naphthalin-1,5-disulfonat und Verfahren zu seiner Herstellung
DE69702831T2 (de)	2001-04-05	Verfahren zur Reinigung von Ketosäuren
EP0760361B1 (fr)	2001-01-10	Procédé de déhalogénation sans racémisation d'arylalkylamines substituées par des halogènes
EP0034836B1 (fr)	1983-07-13	Procédé de préparation de nitroazobenzènes