SU118816A1 - The method of obtaining alpha-chloro-beta-bromotrifluoropropionic acid and its esters - Google Patents
The method of obtaining alpha-chloro-beta-bromotrifluoropropionic acid and its estersInfo
- Publication number
- SU118816A1 SU118816A1 SU606106A SU606106A SU118816A1 SU 118816 A1 SU118816 A1 SU 118816A1 SU 606106 A SU606106 A SU 606106A SU 606106 A SU606106 A SU 606106A SU 118816 A1 SU118816 A1 SU 118816A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- chloro
- esters
- bromotrifluoropropionic
- beta
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title description 3
- 238000000034 method Methods 0.000 title description 2
- KJECGDPBGHLKRS-UHFFFAOYSA-N 3-bromo-2-chloro-2,3,3-trifluoropropanoic acid Chemical compound OC(=O)C(F)(Cl)C(F)(F)Br KJECGDPBGHLKRS-UHFFFAOYSA-N 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- NQCVURBKFRBHMV-UHFFFAOYSA-N 2-bromo-2-chloro-3,3,3-trifluoropropanoic acid Chemical compound OC(=O)C(Cl)(Br)C(F)(F)F NQCVURBKFRBHMV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Предлагаетс способ получени ранее не описанной в литературе а-хлор-Р-бромтрифторпропионовой кислоты и ее эфиров, заключающийс в том, что 1, 1, 2-трифтор-1-бром-2-хлорпентен-3 окисл ют щелочным перманганатом, а дл получени эфиров синтезированной таким образом хлорбромтрифторпропионовой кислоты ее этерифицируют соответствующим спиртом известным образом.A method is proposed for the preparation of a-chloro-P-bromotrifluoropropionic acid and its esters, which has not been previously described in literature, which consists in the fact that 1, 1, 2-trifluoro-1-bromo-2-chloropenten-3 is oxidized by alkaline permanganate, and the esters of chlorobromotrifluoropropionic acid thus synthesized are esterified with the appropriate alcohol in a known manner.
Исходный 1,- 1, 2-трифтор-1-бром-2-хлорпентен-3 можно получить по следующей схеме:The original 1, - 1, 2-trifluoro-1-bromo-2-chloropentene-3 can be obtained according to the following scheme:
CF, . CFCIEI cF.Br СРВгС1 2 11 ИЬ cF.Br - CFC1 - СН, - СНВг - СНз i -. CF2Br - CFC1 - СН СН-СНзCF, CFCIEI cF.Br СРВгС1 2 11 ИЬ cF.Br - CFC1 - СН, - СНВг - СНз i -. CF2Br - CFC1 - CH CH-CH3
Пример 1. Получение «-хлор-Р-бромтрифторпропионовой кислоты Сг2Вг - CF2C1 - СООН.Example 1. Preparation of "-chloro-P-bromotrifluoro-propionic acid Cr2Br - CF2C1 - COOH.
В трехгорлую кр глодонную колбу, снабженную обратным холодильником , мешалкой и капельной воронкой, загружают 150 г щелочного перманганата и 750 мл воды, а затем при энергичном перемещивании и нагревании раствора нри 60° к нему добавл ют по капл м в течение 8 час. 75 г 1, 1, 2-трифтор-1-бром-2-хлорпентена-3.150 g of alkaline permanganate and 750 ml of water are loaded into a three-necked kr gloton flask equipped with a reflux condenser, a stirrer and an addition funnel, and then added vigorously to the 60 ° C solution is added dropwise to it over 8 hours. 75 g 1, 1, 2-trifluoro-1-bromo-2-chloropentene-3.
После окончани реакции реакционную массу охлаждают до 10° и к ней добавл ют 400 мл 15%-ной серной кислоты, после чего в охлаждаемую лед ной водой массу пропускают из ловущки двуокись серы до ее полного обесцвечивани .After completion of the reaction, the reaction mass is cooled to 10 ° and 400 ml of 15% sulfuric acid is added to it, after which sulfur dioxide is passed into the mass cooled with ice water until it is completely discolored.
Затем в делительной воронке отдел ют не вступивший в реакцию исх одный 1, 1, 2-трифтор-1-бром-2-хлорпентен-3 в количестве 17 г а водныи раствор экстрагируют трем порци ми эфира по 50 мл в каждой й фирную выт жку сущат сульфатом натри , эфир отгон ют, а остаток фракционируют. После двухкратного фракционировани получают 20 г вещества с т. кип. 77-80 (5 мм). Выход 33%, счита на вступивщий в реакцию 1, 1, 2-трифтор-1-бром-2-хлорпентен-3Then, in a separating funnel, the unreacted raw material of 1, 1, 2-trifluoro-1-bromo-2-chloropentene-3 in an amount of 17 g is separated, and the aqueous solution is extracted with three 50 ml of ether each time. sodium sulfate, the ether is distilled off and the residue is fractionated. After twofold fractionation, 20 g of the substance with m.p. 77-80 (5 mm). Output 33%, calculated on entering into the reaction of 1, 1, 2-trifluoro-1-bromo-2-chloropenten-3
Q4QТ Т. найденный - 244; вычисленный - 241,5; 1,949; 1,4180. Найдено MR 31,2; вычислено MR., 30;2. Q4QT T. Found - 244; calculated - 241.5; 1,949; 1.4180. Found MR 31.2; calculated mr., 30; 2.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU606106K SU118817A1 (en) | 1958-08-18 | 1958-08-18 | The method of obtaining a mixture of trifluoroacrylic and alpha-ethyl-beta-ethoxytrifluoropropionic acid esters |
| SU606106A SU118816A1 (en) | 1958-08-18 | 1958-08-18 | The method of obtaining alpha-chloro-beta-bromotrifluoropropionic acid and its esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU606106A SU118816A1 (en) | 1958-08-18 | 1958-08-18 | The method of obtaining alpha-chloro-beta-bromotrifluoropropionic acid and its esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU118816A1 true SU118816A1 (en) | 1958-11-30 |
Family
ID=48390812
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU606106K SU118817A1 (en) | 1958-08-18 | 1958-08-18 | The method of obtaining a mixture of trifluoroacrylic and alpha-ethyl-beta-ethoxytrifluoropropionic acid esters |
| SU606106A SU118816A1 (en) | 1958-08-18 | 1958-08-18 | The method of obtaining alpha-chloro-beta-bromotrifluoropropionic acid and its esters |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU606106K SU118817A1 (en) | 1958-08-18 | 1958-08-18 | The method of obtaining a mixture of trifluoroacrylic and alpha-ethyl-beta-ethoxytrifluoropropionic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| SU (2) | SU118817A1 (en) |
-
1958
- 1958-08-18 SU SU606106K patent/SU118817A1/en active
- 1958-08-18 SU SU606106A patent/SU118816A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| SU118817A1 (en) | 1958-11-30 |
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