SU1158038A3 - Method of obtaining 4-nitrodiphenylamine - Google Patents

Method of obtaining 4-nitrodiphenylamine Download PDF

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Publication number
SU1158038A3
SU1158038A3 SU833673464A SU3673464A SU1158038A3 SU 1158038 A3 SU1158038 A3 SU 1158038A3 SU 833673464 A SU833673464 A SU 833673464A SU 3673464 A SU3673464 A SU 3673464A SU 1158038 A3 SU1158038 A3 SU 1158038A3
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formula
mol
nitrodiphenylamine
yield
obtaining
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SU833673464A
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Russian (ru)
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Вилли Мюллер Эрнст
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Байер Аг (Инопредприятие)
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/24—Nitrogen compounds
    • B01J27/26—Cyanides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C07C211/55—Diphenylamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

СПОСОБ ПОЛУЧЕНИЯ 4-КИТРОДИФЕНИПАШНА формулы путем взаимодействи  4-нитрохлорбензола формулы ci с анилином фopмyJфII 40 W в среде органического растворител  в присутствии карбоната кали  и окиси меди (И), отличающййс   тем, что, с целью повыпени  выхода целевого продукта при одноел временном сокращении продолжитель00 ности процесса, последний провод т о в присутствии соли цези  со слабой органической или иеорг амической кис00 лотой. схMETHOD FOR OBTAINING 4-KITRODIFENIPASNA formula by reacting 4-nitrochlorobenzene of formula ci with an aniline formJFII 40 W in an organic solvent in the presence of potassium carbonate and copper oxide (I), characterized in that, to increase the yield of the target product with a single reduction In the process, the latter is carried out in the presence of a cesium salt with weak organic or high amic acid. sc

Description

1 Изобретение относитс  к способам получени  нитродифенипаминов,.в час кости к способам получени  4-нитродифениламина . Цель изобретени  - повышение выхода целевого продукта при одновременном сокращении продолжительности процесса. Пример 1. В 2-литровую тре горлую колбу, снабженную мешалкой и перегонным аппаратом с водоотделителем , при скорости перемешивани , равной 400 оборотам в минуту, подаю 1 моль 4-хлорнитробёнзола, 1,9 моль анилина, 1,25 моль сухого карбоната кали , 1/42 моль окиси меди (II), 1/950 моль сухого карбоната цези  и 1/10 моль ксилола. Реакционную смесь при перемешивании нагревают до 195°С. Содержимое колбы поддерживают приэтой тем пературе до тех пор, пока не выдел етс  10 - 10,5 мл воды и затем пробу -подвергают жидкостной хроматографии дл  определени  содержани  4-хлорнитробензола. Если это содержание составл ет менее 1,5% первоначального количества, реакцию прекращают путем охлаждени . В ином случае реакцию продолжают до 382 достижени  указанного количества. Обща  продолжительность реакции 5-6 ч. При добавл ют 50 мл воды и летучие компоненты отгон ют воц ным паром. Водную фазу содержимого колбы отдел ют, причем органическа  фаза при охлаждении затвердевает. Получают 216 г серо-зеленого вещества , содержащего согласно данным жидкоетной хроматографии 86 вес.% 4-нитродифениламина, что в пересчете на 4.-хлорнитробензол соответствует выходу, равному 87%. Пример 2. Повтор ют пример 1 с той разницей, что вместо карбоната цези  используют 1/930 моль цианида цези . Получают 4-нитродифениламин. Выход составл ет 88,7% (в пересчете на 4-хлорнитробензол). Пример 3. Повтор ют пример Iс той разницей, что используют 1,95 моль анилина, 1,3 моль карбоната кали , 1/45 моль окиси меди (II), 1/850 моль ацетата , 1/20 моль воды и 1/12 моль ксилола и отгон ют IIмл воды. При этом выход 4-нитродифениламина , в пересчете на 4-нитролорбензол , составл ет 89,2%.1 The invention relates to methods for producing nitrodiphenipamines, in an hour of the bone, to methods for producing 4-nitrodiphenylamine. The purpose of the invention is to increase the yield of the target product while reducing the duration of the process. Example 1. In a 2-liter three-flask flask equipped with a stirrer and a distillation apparatus with a water separator, at a stirring speed of 400 revolutions per minute, I fed 1 mol of 4-chloronitrobenzene, 1.9 mol of aniline, 1.25 mol of dry potassium carbonate, 1/42 mol of copper (II) oxide, 1/950 mol of dry cesium carbonate and 1/10 mol of xylene. The reaction mixture with stirring, is heated to 195 ° C. The contents of the flask are maintained at this temperature until 10 to 10.5 ml of water are released and then the sample is subjected to liquid chromatography to determine the content of 4-chloronitrobenzene. If this content is less than 1.5% of the initial amount, the reaction is stopped by cooling. Otherwise, the reaction is continued until 382 is reached. The total reaction time is 5-6 hours. With 50 ml of water is added and the volatile components are stripped off with steam. The aqueous phase of the contents of the flask is separated, and the organic phase solidifies upon cooling. 216 g of a gray-green substance are obtained, containing according to the data of liquid chromatography 86% by weight of 4-nitrodiphenylamine, which, in terms of 4.-chloronitrobenzene, corresponds to a yield equal to 87%. Example 2. Example 1 is repeated, with the difference that 1/930 moles of cesium cyanide are used instead of cesium carbonate. 4-nitrodiphenylamine is obtained. The yield is 88.7% (in terms of 4-chloronitrobenzene). Example 3. Example Ic is repeated, with the difference that 1.95 mol of aniline, 1.3 mol of potassium carbonate, 1/45 mol of copper (II) oxide, 1/850 mol of acetate, 1/20 mol of water and 1/12 are used. mole of xylene and distilled II ml of water. The yield of 4-nitrodiphenylamine, in terms of 4-nitrolorbenzene, is 89.2%.

Claims (1)

СПОСОБ ПОЛУЧЕНИЯ 4-НИТРО ДИФЕНИЛАМИНА формулы путем взаимодействия 4—нитрохлорбензола формулы ci с анилином формудаMETHOD FOR PRODUCING 4-NITRO DIPHENYLAMINE of the formula by reaction of 4-nitrochlorobenzene of the formula ci with aniline of the formula МН2 5MH 2 5 0 |с в среде органического растворителя — в присутствии карбоната калия и окиси меди (II), отличающийс я тем, что, с целью повыпения выхода целевого продукта при одновременном сокращении продолжительности процесса, последний проводят в присутствии соли цезия со слабой ,органической или неорганической кислотой.0 | s in an organic solvent medium - in the presence of potassium carbonate and copper (II) oxide, characterized in that, in order to increase the yield of the target product while reducing the duration of the process, the latter is carried out in the presence of a cesium salt with a weak, organic or inorganic acid . 1 1158038 21 1158038 2
SU833673464A 1982-12-14 1983-12-12 Method of obtaining 4-nitrodiphenylamine SU1158038A3 (en)

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DE19823246151 DE3246151A1 (en) 1982-12-14 1982-12-14 Process for the preparation of 4-nitrodiphenylamines

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SU833673464A SU1158038A3 (en) 1982-12-14 1983-12-12 Method of obtaining 4-nitrodiphenylamine

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JP (1) JPS59112947A (en)
KR (1) KR910002370B1 (en)
BR (1) BR8306844A (en)
CS (1) CS236898B2 (en)
DD (1) DD215536A5 (en)
DE (1) DE3246151A1 (en)
IN (1) IN160179B (en)
SU (1) SU1158038A3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2502724C1 (en) * 2012-10-22 2013-12-27 Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации Method of producing nitrodiphenylamines

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19942394C1 (en) 1999-09-06 2001-02-01 Bayer Ag Increasing the yield of nitrodiphenylamines in base/palladium-catalysed nitrohalobenzene/aromatic amine reactions by using a base which has been milled and optionally also dried
DE10005601A1 (en) 2000-02-09 2001-08-16 Bayer Ag Process for the preparation of aminodiphenylamines
DE10300125A1 (en) 2003-01-07 2004-07-15 Bayer Ag Process for the preparation of nitrodiphenylamines
DE10300126A1 (en) * 2003-01-07 2004-07-15 Bayer Aktiengesellschaft Process for the preparation of aminodiphenylamines

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL211629A (en) * 1955-12-07
DE1056619B (en) * 1956-11-29 1959-05-06 Bayer Ag Process for the preparation of 4-nitro-diarylamines
DE1090225B (en) * 1957-11-05 1960-10-06 Us Rubber Co Process for the preparation of p-nitrodiphenylamines
US3155727A (en) * 1960-07-25 1964-11-03 Goodyear Tire & Rubber Reaction of aromatic amines with para halo nitrobenzenes using copper cyanide condensation catalyst
US3313854A (en) * 1961-11-20 1967-04-11 Universal Oil Prod Co Preparation of para-nitrodiphenylamines utilizing a copper oxide catalyst
US3277175A (en) * 1963-11-26 1966-10-04 Eastman Kodak Co Preparation of p-nitrodiphenylamines
US4187248A (en) * 1977-11-23 1980-02-05 Monsanto Company Making a nitrodiarylamine by reacting an alkali metal salt of a formamide with a nitrohaloarene
US4187249A (en) * 1977-12-27 1980-02-05 Monsanto Company Promoting the reaction of sodium salts of formyl derivatives of aromatic amines to form nitrodiarylamines
US4209463A (en) * 1977-12-27 1980-06-24 Monsanto Company Promoting the formation of nitrodiarylamines from nitrohaloarenes, activated aryl amines and sodium carbonates
US4228103A (en) * 1978-03-13 1980-10-14 Monsanto Company Effecting condensation of nitrohaloarene and formyl derivative of a primary aromatic amine with alkali metal hydroxide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Патент US № 2927943, кл. 260-276, опублик. 1960. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2502724C1 (en) * 2012-10-22 2013-12-27 Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации Method of producing nitrodiphenylamines

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KR910002370B1 (en) 1991-04-20
JPS59112947A (en) 1984-06-29
DE3246151C2 (en) 1988-06-30
DD215536A5 (en) 1984-11-14
KR840007560A (en) 1984-12-08
CS236898B2 (en) 1985-05-15
DE3246151A1 (en) 1984-06-14
JPS6323184B2 (en) 1988-05-16
BR8306844A (en) 1984-07-24
IN160179B (en) 1987-06-27

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