SU1158038A3 - Способ получени 4-нитродифениламина - Google Patents
Способ получени 4-нитродифениламина Download PDFInfo
- 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
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formula
- mol
- nitrodiphenylamine
- yield
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 title claims description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims abstract description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 8
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000005751 Copper oxide Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910000431 copper oxide Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- XTCPEYCUFMHXBI-UHFFFAOYSA-N cesium;cyanide Chemical compound [Cs+].N#[C-] XTCPEYCUFMHXBI-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
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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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Inorganic Chemistry (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. сх
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%.
Claims (1)
- СПОСОБ ПОЛУЧЕНИЯ 4-НИТРО ДИФЕНИЛАМИНА формулы путем взаимодействия 4—нитрохлорбензола формулы ci с анилином формудаМН2 50 |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.1 1158038 2
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823246151 DE3246151A1 (de) | 1982-12-14 | 1982-12-14 | Verfahren zur herstellung von 4-nitrodiphenylaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1158038A3 true SU1158038A3 (ru) | 1985-05-23 |
Family
ID=6180570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833673464A SU1158038A3 (ru) | 1982-12-14 | 1983-12-12 | Способ получени 4-нитродифениламина |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS59112947A (ru) |
| KR (1) | KR910002370B1 (ru) |
| BR (1) | BR8306844A (ru) |
| CS (1) | CS236898B2 (ru) |
| DD (1) | DD215536A5 (ru) |
| DE (1) | DE3246151A1 (ru) |
| IN (1) | IN160179B (ru) |
| SU (1) | SU1158038A3 (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2502724C1 (ru) * | 2012-10-22 | 2013-12-27 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Способ получения нитродифениламинов |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942394C1 (de) | 1999-09-06 | 2001-02-01 | Bayer Ag | Verfahren zur Herstellung von Nitrodiphenylaminen |
| DE10005601A1 (de) | 2000-02-09 | 2001-08-16 | Bayer Ag | Verfahren zur Herstellung von Aminodiphenylaminen |
| DE10300125A1 (de) | 2003-01-07 | 2004-07-15 | Bayer Ag | Verfahren zur Herstellung von Nitrodiphenylaminen |
| DE10300126A1 (de) * | 2003-01-07 | 2004-07-15 | Bayer Aktiengesellschaft | Verfahren zur Herstellung von Aminodiphenylaminen |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL211629A (ru) * | 1955-12-07 | |||
| DE1056619B (de) * | 1956-11-29 | 1959-05-06 | Bayer Ag | Verfahren zur Herstellung von 4-Nitro-diarylaminen |
| DE1090225B (de) * | 1957-11-05 | 1960-10-06 | Us Rubber Co | Verfahren zur Herstellung von p-Nitrodiphenylaminen |
| 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 |
-
1982
- 1982-12-14 DE DE19823246151 patent/DE3246151A1/de active Granted
-
1983
- 1983-11-10 IN IN751/DEL/83A patent/IN160179B/en unknown
- 1983-11-29 KR KR1019830005642A patent/KR910002370B1/ko not_active Expired
- 1983-12-09 JP JP58231624A patent/JPS59112947A/ja active Granted
- 1983-12-12 CS CS839327A patent/CS236898B2/cs unknown
- 1983-12-12 DD DD83257811A patent/DD215536A5/de not_active IP Right Cessation
- 1983-12-12 SU SU833673464A patent/SU1158038A3/ru active
- 1983-12-13 BR BR8306844A patent/BR8306844A/pt not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 2927943, кл. 260-276, опублик. 1960. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2502724C1 (ru) * | 2012-10-22 | 2013-12-27 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Способ получения нитродифениламинов |
Also Published As
| Publication number | Publication date |
|---|---|
| CS236898B2 (en) | 1985-05-15 |
| IN160179B (ru) | 1987-06-27 |
| JPS59112947A (ja) | 1984-06-29 |
| BR8306844A (pt) | 1984-07-24 |
| JPS6323184B2 (ru) | 1988-05-16 |
| DE3246151A1 (de) | 1984-06-14 |
| KR840007560A (ko) | 1984-12-08 |
| DD215536A5 (de) | 1984-11-14 |
| KR910002370B1 (ko) | 1991-04-20 |
| DE3246151C2 (ru) | 1988-06-30 |
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