SU203664A1 - Method of producing monovinyl aceticene ethers containing two atom of oxygen in the molecule - Google Patents
Method of producing monovinyl aceticene ethers containing two atom of oxygen in the moleculeInfo
- Publication number
- SU203664A1 SU203664A1 SU1109100A SU1109100A SU203664A1 SU 203664 A1 SU203664 A1 SU 203664A1 SU 1109100 A SU1109100 A SU 1109100A SU 1109100 A SU1109100 A SU 1109100A SU 203664 A1 SU203664 A1 SU 203664A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- molecule
- aceticene
- oxygen
- atom
- ethers containing
- Prior art date
Links
- 150000002170 ethers Chemical class 0.000 title description 2
- 125000004429 atoms Chemical group 0.000 title 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 title 1
- 239000001301 oxygen Substances 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- -1 acetylene ethers Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- BLRXYTIIKIPJQL-UHFFFAOYSA-N dicarbide(1-) Chemical compound [C-]#C BLRXYTIIKIPJQL-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atoms Chemical group O* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Данное изобретение относитс к области получени моновнниловых ацетиленовых эфиров. Предлагаемый способ получени моновиниловых ацетиленовых эфиров, содержащих в молекуле два атома кислорода, состоит в том, что ацетиленид или алкилацетиленид натри подвергают взаимодействию с окисью этилена и винил-р-хлорэтиловым эфиром в среде жидкого аммиака. Пример 1. Синтез 1-винилокси,2-бутин-3, окси-Г-этана. К 24 г ацетиленида натри в 400 мл жидкого аммиака добавл ют по капл м 25 мл окиси этилена. Смесь перемешивают 2 час, затем прикапывают при перемешивании 60 г винил-|3-хлорэтилового эфира в 100 мл диэтилового эфира. Смесь оставл ют иа ночь в бане из сухого льда. Затем испар ют большую часть аммиака, добавл ют еше 200 мл диэтилового эфира и разлагают смесь водой. Органическую часть экстрагируют 200 мл эфира, сушат поташом. После удалени эфира при перегонке в вакууме выдел ют 17,5 г (25%) 1-винилокси, 2-бутин-З, окси-Гэтаиа с т. кии. 76-78С (15 мм рт. ст.); Лц 1,4522; df 0,9554; MRo найдено 39,61, вычислено 40,10. В ИК.-снектре обнарул ены частоты 1627, 1642, 3120 «, соответствующие винилокси1-руппе , и частота 3300 , соответствующа группе С СН. Пример 2. Синтез 1-винилокси, 2-октин-З, окси-Г-этана. Аналогично предыдущему оныту при взаимодействии 52 г бутилацетиленида натри , 25 мл окиси этилена и 60 г винил-рхлорэтилового эфира в 400 мл жидкого аммиака получают 32,5 г (30%) 1-винилокси, 2-октип-3,окси-Г-этана с т. кип. 97-98°С (1,5 мм рт. ст.); пп 1,4670; df 0,9294; MR с найдено 58,60, вычислено 59,16. Найдено, %: С 73,07; 73,41; Н 10,46; 10,36. ( T- О Вычислепо, %; С 73,42; Н 10,27. Строеппе подтверждено ИК-спектром. Вииилоксигруппе соответствуют частоты 1620, 1640, 3120 см . Группе соответствует частота 2120 см Предмет изобретени Снособ получени моновиниловых ацетиленовых эфиров, содержащих в молекуле два атома кислорода, отличающийс тем, что ацетиленид или алкилацетиленид натри подвергают взаимодействию с окисью этилена и винил-|3-хлорэтиловым эфиром в среде жидкого аммиака.This invention relates to the field of the preparation of monovnyl acetylene ethers. The proposed method for the preparation of monovinyl acetylenic ethers containing two oxygen atoms in a molecule is that sodium acetylide or sodium acetyl acetylide is reacted with ethylene oxide and vinyl-p-chloroethyl ether in liquid ammonia. Example 1. Synthesis of 1-vinyloxy, 2-butyn-3, hydroxy-G-ethane. 25 ml of ethylene oxide is added dropwise to 24 g of sodium acetylide in 400 ml of liquid ammonia. The mixture is stirred for 2 hours, then 60 g of vinyl 3-chloroethyl ether in 100 ml of diethyl ether are added dropwise with stirring. The mixture was left overnight in a dry ice bath. Then most of the ammonia is evaporated, more 200 ml of diethyl ether is added and the mixture is decomposed with water. The organic part is extracted with 200 ml of ether, dried with potash. After removal of the ether by distillation in vacuo, 17.5 g (25%) of 1-vinyloxy, 2-butine-3, hydroxy-Getaium with so-called tia was isolated. 76-78 ° C (15 mmHg); Lz 1.4522; df 0.9554; MRo found 39.61, calculated 40.10. In the IR-spectrum, frequencies 1627, 1642, 3120 “were detected, corresponding to the vinyloxy-group, and frequency 3300, corresponding to the group С СН. Example 2. Synthesis of 1-vinyloxy, 2-octin-3, hydroxy-G-ethane. Similarly to the previous process, by interaction of 52 g of sodium butylacetylenide, 25 ml of ethylene oxide and 60 g of vinyl-chloroethyl ether in 400 ml of liquid ammonia, 32.5 g (30%) of 1-vinyloxy, 2-octip-3, oxy-G-ethane are obtained with t. kip. 97-98 ° C (1.5 mm Hg. Art.); PP 1.4670; df 0.9294; MR with found 58.60, calculated 59.16. Found,%: C 73.07; 73.41; H 10.46; 10.36. (T-O Calculated,%; C 73.42; H 10.27. Stroippe is confirmed by IR spectrum. Wiiiloxy group corresponds to 1620, 1640, 3120 cm. Group corresponds to 2120 cm frequency. Subject of the invention. Method of obtaining monovinyl acetylene ethers containing in the molecule two oxygen atoms, characterized in that the acetylenide or sodium alkyl acetylenide is reacted with ethylene oxide and vinyl - 3-chloroethyl ether in liquid ammonia.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU203664A1 true SU203664A1 (en) |
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