SU322986A1 - The method of producing cyclopropanecarboxylic acid esters - Google Patents
The method of producing cyclopropanecarboxylic acid estersInfo
- Publication number
- SU322986A1 SU322986A1 SU1482529A SU1482529A SU322986A1 SU 322986 A1 SU322986 A1 SU 322986A1 SU 1482529 A SU1482529 A SU 1482529A SU 1482529 A SU1482529 A SU 1482529A SU 322986 A1 SU322986 A1 SU 322986A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- cyclopropanecarboxylic acid
- acid esters
- acid
- cyclopropanecarboxylic
- producing
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение относитс к способу получени производных циклопропанкарбоновой кислоты , в частности сложных эфиров, которые могут найти применение как инсектициды.This invention relates to a process for the preparation of cyclopropanecarboxylic acid derivatives, in particular esters, which can be used as insecticides.
Известен способ получени сложных эфиров циклопропанкарбоновой кислоты путем ацилировани спиртов хлорангидридом циклопропанкарбоновой кислоты. По этому спосОбу из циклопропанкарбоновой кислоты первоначально получают ее хлорангидрид действием п тихлористого фосфора или хлористого тионила, обладающих высокой токсичностью.A known method for producing cyclopropanecarboxylic acid esters by acylating alcohols with cyclopropanecarboxylic acid chloride. In this way, cyclopropanecarboxylic acid is initially obtained by its acid chloride by the action of phosphorus pentachloride or thionyl chloride, which is highly toxic.
С целью упрощени процесса и увеличени выхода продукта, предлагаетс циклопропанкарбоновую кислоту подвергать реакции этерификации со спиртами в присутствии кислого катализатора, например ft-толуолсульфокислоты , в среде азеотропообразующего растворител , например толуола или четыреххлористого углерода, при температуре кипени реакционной смеси. Выход 60-70%.In order to simplify the process and increase the yield of the product, it is proposed to cyclopropanecarboxylic acid to undergo esterification reactions with alcohols in the presence of an acidic catalyst, for example, ft-toluene sulfonic acid, in an azeotropic solvent, such as toluene or carbon tetrachloride, at the boiling point of the reaction mixture. Yield 60-70%.
Пример 1. Метиловый эфир циклопропанкарбоновой кислоты. Смесь 8,6 г (0,1 моль) кислоты, 12 мм метанола, 30 мм четыреххлористого углерода и 0,05 г «-толуолсульфокислоты кип т т в течение 10 час. Нижний слой отдел ют, промывают водой и перегон ют. Выдел ют 7 г (70%) продукта, т. кип. 117- 118°С/755 мм рт. ст.; 1,4200, по литературным данным т. кип. 119°С/764 мм рт. ст.; п2рО 1,4186.Example 1. Methyl ester of cyclopropanecarboxylic acid. A mixture of 8.6 g (0.1 mol) of acid, 12 mm of methanol, 30 mm of carbon tetrachloride and 0.05 g of α-toluene sulfonic acid is boiled for 10 hours. The bottom layer is separated, washed with water and distilled. 7 g (70%) of product were isolated, t. Bales. 117- 118 ° C / 755 mm Hg. v .; 1,4200, according to literary data t. Kip. 119 ° C / 764 mm Hg v .; p2pO 1.4186.
Пример 2. Бутиловый эфир циклопропанкарбоновой кислоты. Смесь 8,6 г (0,1 моль) кислоты, 10 мм бутанола, 20 мм толуола и 0,1 г tt-толуолсульфокнслоты кип т т с водоотделителем до прекращени выделени воды (около 6 час). Затем смесь нейтрализуют 5%ным раствором бикарбоната натри и выдел ют 10 г (70%) продукта, т. кип. 72-73°С/ /16 мм рт. ст.; п 1° 1,4290, по литературным данным; т. кип. 175°С/759 мм рт. ст.; п 1,4285.Example 2. Cyclopropanecarboxylic butyl ester. A mixture of 8.6 g (0.1 mol) of acid, 10 mm of butanol, 20 mm of toluene and 0.1 g of tt-toluenesulfonic acid is boiled with a water separator until the evolution of water stops (about 6 hours). The mixture is then neutralized with a 5% sodium bicarbonate solution and 10 g (70%) of product are isolated, i.e. 72-73 ° С / / 16 mm Hg. v .; n 1 ° 1,4290, according to literary data; m.p. 175 ° C / 759 mm Hg. v .; P 1,4285.
Сложные эфиры: этиловый, амиловый, аллиловый и пропаргиловый,-получают аналогично примеру 2 с выходами соответственно 60; 75; 72 и 50%.Esters: ethyl, amyl, allyl and propargyl, - are obtained analogously to example 2 with the outputs, respectively, 60; 75; 72 and 50%.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1482529A SU322986A1 (en) | 1970-09-28 | 1970-09-28 | The method of producing cyclopropanecarboxylic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1482529A SU322986A1 (en) | 1970-09-28 | 1970-09-28 | The method of producing cyclopropanecarboxylic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU322986A1 true SU322986A1 (en) | 1976-01-15 |
Family
ID=20458297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1482529A SU322986A1 (en) | 1970-09-28 | 1970-09-28 | The method of producing cyclopropanecarboxylic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU322986A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0779269A1 (en) * | 1995-12-15 | 1997-06-18 | Bayer Ag | Process for the preparation of synthetic pyrethroids by azeotropic esterification |
-
1970
- 1970-09-28 SU SU1482529A patent/SU322986A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0779269A1 (en) * | 1995-12-15 | 1997-06-18 | Bayer Ag | Process for the preparation of synthetic pyrethroids by azeotropic esterification |
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