CA1221701A - Preparation de 2-(2'-hydroxyphenyl)-benzotriazoles a partir de 2-nitro-2"-hydroxyazobenzenes - Google Patents

Preparation de 2-(2'-hydroxyphenyl)-benzotriazoles a partir de 2-nitro-2"-hydroxyazobenzenes

Info

Publication number: CA1221701A
Authority: CA; Canada
Prior art keywords: carbon atoms; hydrogen; alkyl; process according; formula
Prior art date: 1984-05-24
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

CA000455004A

Other languages

English (en)

Inventor

Alexander Davatz

Tibor Somlo

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-05-24

Filing date

1984-05-24

Publication date

1987-05-12

1984-05-24 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1984-05-24 Priority to CA000455004A priority Critical patent/CA1221701A/fr

1987-05-12 Application granted granted Critical

1987-05-12 Publication of CA1221701A publication Critical patent/CA1221701A/fr

Status Expired legal-status Critical Current

Links

FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title claims abstract 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
150000001875 compounds Chemical class 0.000 claims abstract description 21
-1 2-nitro-2'-hydroxyazobenzene com-pound Chemical class 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
239000003054 catalyst Substances 0.000 claims abstract description 10
CIVLEPQUPHSEBS-UHFFFAOYSA-N 2-[(2-nitrophenyl)diazenyl]phenol Chemical class OC1=CC=CC=C1N=NC1=CC=CC=C1[N+]([O-])=O CIVLEPQUPHSEBS-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052736 halogen Chemical group 0.000 claims description 11
150000002367 halogens Chemical group 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
239000000460 chlorine Chemical group 0.000 claims description 7
229910052801 chlorine Chemical group 0.000 claims description 7
FRASJONUBLZVQX-UHFFFAOYSA-N naphthoquinone group Chemical group C1(C=CC(C2=CC=CC=C12)=O)=O FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229930192627 Naphthoquinone Natural products 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
239000000758 substrate Substances 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
235000019441 ethanol Nutrition 0.000 claims 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
125000004663 dialkyl amino group Chemical group 0.000 claims 1
229960004756 ethanol Drugs 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
239000011368 organic material Substances 0.000 abstract description 2
239000003381 stabilizer Substances 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
229920000180 alkyd Chemical group 0.000 description 12
150000002431 hydrogen Chemical group 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
239000003638 chemical reducing agent Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
150000004054 benzoquinones Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000002791 naphthoquinones Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
CCTJHVLTAJTPBV-UHFFFAOYSA-N 2-chloro-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(Cl)=CC(=O)C2=C1 CCTJHVLTAJTPBV-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
150000004055 1,2-benzoquinones Chemical class 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
150000004057 1,4-benzoquinones Chemical class 0.000 description 1
YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
QSLFQVQZSKRPHS-UHFFFAOYSA-N 2-chloro-3-(dimethylamino)naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(N(C)C)=C(Cl)C(=O)C2=C1 QSLFQVQZSKRPHS-UHFFFAOYSA-N 0.000 description 1
PEXGTUZWTLMFID-UHFFFAOYSA-N 2-phenyldiazenylphenol Chemical class OC1=CC=CC=C1N=NC1=CC=CC=C1 PEXGTUZWTLMFID-UHFFFAOYSA-N 0.000 description 1
208000034723 Amelia Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
240000002132 Beaucarnea recurvata Species 0.000 description 1
208000006586 Ectromelia Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010024503 Limb reduction defect Diseases 0.000 description 1
206010034016 Paronychia Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000017899 Spathodea campanulata Nutrition 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
241000009298 Trigla lyra Species 0.000 description 1
235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
210000001217 buttock Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 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
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Landscapes

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

CA000455004A 1984-05-24 1984-05-24 Preparation de 2-(2'-hydroxyphenyl)-benzotriazoles a partir de 2-nitro-2"-hydroxyazobenzenes Expired CA1221701A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000455004A CA1221701A (fr)	1984-05-24	1984-05-24	Preparation de 2-(2'-hydroxyphenyl)-benzotriazoles a partir de 2-nitro-2"-hydroxyazobenzenes

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000455004A CA1221701A (fr)	1984-05-24	1984-05-24	Preparation de 2-(2'-hydroxyphenyl)-benzotriazoles a partir de 2-nitro-2"-hydroxyazobenzenes

Publications (1)

Publication Number	Publication Date
CA1221701A true CA1221701A (fr)	1987-05-12

Family

ID=4127923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000455004A Expired CA1221701A (fr)	1984-05-24	1984-05-24	Preparation de 2-(2'-hydroxyphenyl)-benzotriazoles a partir de 2-nitro-2"-hydroxyazobenzenes

Country Status (1)

Country	Link
CA (1)	CA1221701A (fr)

1984
- 1984-05-24 CA CA000455004A patent/CA1221701A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-05-24	MKEX	Expiry

Publication	Publication Date	Title
US4642350A (en)	1987-02-10	Novel process for preparation of benzotriazoles using aryldiols and quinones
US4230867A (en)	1980-10-28	Process for the production of 2-aryl-2H-benzotriazoles
KR870001382B1 (ko)	1987-07-24	트리아진유도체의 제조방법
EP0172413B1 (fr)	1993-06-16	Procédé pour la préparation de dérivés de la pipéridine
GB2063259A (en)	1981-06-03	Resorcinol derivatives
CA1047500A (fr)	1979-01-30	Synthese industrielle de (hydroxyphenyl-2)-2 benzotriazoles
CA1221701A (fr)	1987-05-12	Preparation de 2-(2'-hydroxyphenyl)-benzotriazoles a partir de 2-nitro-2"-hydroxyazobenzenes
US5086173A (en)	1992-02-04	Process for the preparation of alkylhydroxyanilinothiotriazine derivatives
US2952689A (en)	1960-09-13	Coumarin derivatives and their production
US2121723A (en)	1938-06-21	Aralkyl ethers
US4224451A (en)	1980-09-23	Process for the preparation of 2-aryl-2H-benzotriazoles
US5739348A (en)	1998-04-14	Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process
US4980512A (en)	1990-12-25	Preparation of 2-hydroxy-4-alkoxybenzophenones
US2559011A (en)	1951-07-03	Manufacture of n-allyl derivatives
US3036106A (en)	1962-05-22	Alkyl and acyl ferrocenes
US3291841A (en)	1966-12-13	Process for the preparation of benzyl ethers
US4892957A (en)	1990-01-09	Process for the preparation of a n-alkylated bipyrazoleanthrone
CA1241659A (fr)	1988-09-06	Methode de preparation de 2-phenylbenzotriazole
US2109458A (en)	1938-03-01	Aralkyl ethers of acyl-phenols
GB1561025A (en)	1980-02-13	Process for preparing 2 - alkoxy - 6 - bromo - naphthalenes
US2698329A (en)	1954-12-28	Trimethylenedioxybenzene and certain derivatives thereof
JPS61218577A (ja)	1986-09-29	２−（２′−ヒドロキシフエニル）ベンゾトリアゾ−ル類の製造方法
US3133928A (en)	1964-05-19	Certificate of correction
US3291842A (en)	1966-12-13	Method of preparing benzyl ethers
JPS601292B2 (ja)	1985-01-14	ジハイドロコエンザイムｑ類化合物の合成法