CH628020A5 - Process for preparing aminonitrophenols - Google Patents

Process for preparing aminonitrophenols Download PDF

Info

Publication number: CH628020A5
Authority: CH; Switzerland
Prior art keywords: mol; reduction; salt; compounds; polynitrophenol
Prior art date: 1976-04-06

Application number

CH421877A

Other languages

German (de)

English (en)

Inventor

Karl Dr Linhart

Adolf Dr Friedrich

Original Assignee

Bayer 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.)

1976-04-06

Filing date

1977-04-04

Publication date

1982-02-15

1977-04-04 Application filed by Bayer Ag filed Critical Bayer Ag

1982-02-15 Publication of CH628020A5 publication Critical patent/CH628020A5/de

Links

BLCZXLGRKKRKJJ-UHFFFAOYSA-N 3-amino-2-nitrophenol Chemical class NC1=CC=CC(O)=C1[N+]([O-])=O BLCZXLGRKKRKJJ-UHFFFAOYSA-N 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims description 30
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
-1 sulfide ions Chemical class 0.000 claims description 13
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical class OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 10
239000000243 solution Substances 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 5
239000000706 filtrate Substances 0.000 claims description 5
JCRIDWXIBSEOEG-UHFFFAOYSA-N 2,6-dinitrophenol Chemical class OC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O JCRIDWXIBSEOEG-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000001816 cooling Methods 0.000 claims description 3
238000001914 filtration Methods 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
230000000737 periodic effect Effects 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
150000003863 ammonium salts Chemical class 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
235000002639 sodium chloride Nutrition 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000000203 mixture Substances 0.000 description 5
PCBCIXWBAPIVDV-UHFFFAOYSA-N 2-chloro-4,6-dinitrophenol Chemical compound OC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O PCBCIXWBAPIVDV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
229920001021 polysulfide Polymers 0.000 description 4
239000005077 polysulfide Substances 0.000 description 4
150000008117 polysulfides Polymers 0.000 description 4
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 4
KESYALTWUAFAAC-UHFFFAOYSA-N 2,6-dinitro-4-chlorophenol Chemical compound OC1=C([N+]([O-])=O)C=C(Cl)C=C1[N+]([O-])=O KESYALTWUAFAAC-UHFFFAOYSA-N 0.000 description 3
VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000012535 impurity Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
BTJIUGUIPKRLHP-UHFFFAOYSA-M 4-nitrophenolate Chemical compound [O-]C1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-M 0.000 description 2
TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
229910052977 alkali metal sulfide Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000004763 sulfides Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
UWEZBKLLMKVIPI-UHFFFAOYSA-N 2,5-dinitrophenol Chemical compound OC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O UWEZBKLLMKVIPI-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 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
239000000975 dye Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 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
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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000286 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
125000004344 phenylpropyl group Chemical group 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

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

CH421877A 1976-04-06 1977-04-04 Process for preparing aminonitrophenols CH628020A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762614825 DE2614825C3 (de)	1976-04-06	1976-04-06	Verfahren zur Herstellung von Aminonitrophenolen

Publications (1)

Publication Number	Publication Date
CH628020A5 true CH628020A5 (en)	1982-02-15

Family

ID=5974575

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH421877A CH628020A5 (en)	1976-04-06	1977-04-04	Process for preparing aminonitrophenols

Country Status (9)

Country	Link
JP (1)	JPS52122327A (it)
BE (1)	BE853291A (it)
BR (1)	BR7702163A (it)
CH (1)	CH628020A5 (it)
DE (1)	DE2614825C3 (it)
ES (1)	ES457558A1 (it)
FR (1)	FR2347332A1 (it)
GB (1)	GB1512775A (it)
IT (1)	IT1073238B (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3002254A1 (de) *	1980-01-23	1981-07-30	Cassella Ag, 6000 Frankfurt	Verfahren zur herstellung von 2-amino-4-nitrophenol
DE4018335A1 (de) *	1990-06-08	1991-12-12	Wella Ag	Mittel zum faerben von haaren mit einem gehalt an 2-amino-4-halogen-6-nitrophenolen sowie 2-amino-4-fluor-6-nitrophenol
CN113372228B (zh) *	2021-06-08	2022-08-26	浙江鼎龙科技股份有限公司	一种2-氨基-6-氯-4-硝基苯酚的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2464194A (en) *	1945-05-05	1949-03-08	Gen Aniline & Film Corp	Reduction of nitrophenols
GB1001092A (en) *	1962-09-27	1965-08-11	Monsanto Chem Australia Ltd	Production of aminoquinolines
FR1534593A (fr) *	1966-09-02	1968-07-26	Merck & Co Inc	Réduction d'un composé nitrophénylique en composé aminophénylique

1976
- 1976-04-06 DE DE19762614825 patent/DE2614825C3/de not_active Expired
1977
- 1977-04-04 CH CH421877A patent/CH628020A5/de not_active IP Right Cessation
- 1977-04-04 IT IT4880177A patent/IT1073238B/it active
- 1977-04-04 GB GB1410777A patent/GB1512775A/en not_active Expired
- 1977-04-05 ES ES457558A patent/ES457558A1/es not_active Expired
- 1977-04-05 BR BR7702163A patent/BR7702163A/pt unknown
- 1977-04-05 JP JP3820577A patent/JPS52122327A/ja active Pending
- 1977-04-06 BE BE2055805A patent/BE853291A/xx not_active IP Right Cessation
- 1977-04-06 FR FR7710458A patent/FR2347332A1/fr active Granted

Also Published As

Publication number	Publication date
BE853291A (fr)	1977-10-06
GB1512775A (en)	1978-06-01
FR2347332B1 (it)	1983-09-09
DE2614825B2 (de)	1980-05-08
ES457558A1 (es)	1978-03-16
DE2614825A1 (de)	1977-10-13
DE2614825C3 (de)	1981-01-29
FR2347332A1 (fr)	1977-11-04
JPS52122327A (en)	1977-10-14
BR7702163A (pt)	1978-10-31
IT1073238B (it)	1985-04-13

Legal Events

Date	Code	Title	Description
1986-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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AT239243B (de)	1965-03-25	Verfahren zur Herstellung von 2, 3-Dicyan-1, 4-dithia-anthrahydrochinon und -anthrachinon
DE2758786A1 (de)	1979-07-12	Verfahren zur herstellung von bis-(amino-phenyl)-disulfiden
AT246117B (de)	1966-04-12	Verfahren zur Herstellung von 6,8-Dithiooctansäureamiden
CH594617A5 (en)	1978-01-13	Sulphonated di:styryl cpd. prodn. by anil synthesis
DE4201801A1 (de)	1992-07-30	Verfahren zum reinigen von roher 4,4'-diamino-1,1'-dianthrachinonyl-3,3'-disulfonsaeure und ihren salzen