SU218141A1 - METHOD OF OBTAINING AMINO ACETYLENE DI- OR TETRAVINYL ETHER - Google Patents
METHOD OF OBTAINING AMINO ACETYLENE DI- OR TETRAVINYL ETHERInfo
- Publication number
- SU218141A1 SU218141A1 SU1102916A SU1102916A SU218141A1 SU 218141 A1 SU218141 A1 SU 218141A1 SU 1102916 A SU1102916 A SU 1102916A SU 1102916 A SU1102916 A SU 1102916A SU 218141 A1 SU218141 A1 SU 218141A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetylene
- tetravinyl ether
- mol
- obtaining amino
- paraform
- Prior art date
Links
- VXAWCKIQYKXJMD-UHFFFAOYSA-N ethynamine Chemical compound NC#C VXAWCKIQYKXJMD-UHFFFAOYSA-N 0.000 title claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- -1 vinyloxyethyl Chemical group 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XYZOZJCEKYPOHC-UHFFFAOYSA-N 2-ethenoxy-N-(2-ethenoxyethyl)ethanamine Chemical compound C=COCCNCCOC=C XYZOZJCEKYPOHC-UHFFFAOYSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M Copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 229960000834 vinyl ether Drugs 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940052303 Ethers for general anesthesia Drugs 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N O-amino-Hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
Предложен способ получени аминоацетиле. новых ди- или тетравиниловых эфиров взаимодействием 1 или 2 моль дивинилового эфира ди-(оксиалкил)-амина с 1 моль параформом и ацетиленом в присутствии солей одновалентной меди при 60-80°С в автоклаве. Дл ускорени процесс ведут в среде инертного растворител , например диоксана.A method of producing aminoacetyl is proposed. new di- or tetravinyl ethers by reacting 1 or 2 mol of di- (oxyalkyl) -amine divinyl ether with 1 mol of paraform and acetylene in the presence of monovalent copper salts at 60-80 ° C in an autoclave. To accelerate the process, the process is conducted in an inert solvent, for example dioxane.
Полученные ненасыщенные аминоэфиры вл ютс высокореакционноспособными соединени ми и могут найти применение в органическом синтезе.The resulting unsaturated aminoethers are highly reactive compounds and can be used in organic synthesis.
Пример 1. 7,86 г (0,05 моль) дивинилового эфира диэтаноламина, 2,1 г (0,07 моль) параформа и 0,1 г CuCl в 30 мл диоксана нагревают при 70-75°С в однолитровом вращающемс автоклаве под давлением ацетилена (начальное давление 10 атм) в течение 3 час. Продукт фильтруют и перегон ют, получают 5,36 г ди-(винилоксиэтил)-пропин-2иламина; т. кип. 83°С (1,5 мм рт. ст.); По 1,4725; df 0,9539, MR о 57,28, вычислено 57 29Example 1. 7.86 g (0.05 mol) of diethanolamine divinyl ether, 2.1 g (0.07 mol) of paraform and 0.1 g of CuCl in 30 ml of dioxane are heated at 70-75 ° C in a one-liter rotating autoclave under pressure of acetylene (initial pressure 10 atm) for 3 hours. The product is filtered and distilled to give 5.36 g of di- (vinyloxyethyl) propyn-2-amine; m.p. 83 ° C (1.5 mmHg); At 1.4725; df 0.9539, MR about 57.28, calculated 57 29
Найдено, С 67,52; Н 8,66; N 7,49.Found, C 67.52; H 8.66; N 7.49.
CuHivNOa.CuHivNOa.
Пример 2. На стадии образовани ди-(винилоксиэтил )-пропин-2-иламина (см. пример 1) к реакционной массе в автоклаве добавл ют 5,02 г (0,32 моль) дивинилового эфира диэтаноламина, 0,96 г (0,032 моль) параформа , 0,1 г CuCl. Смесь нагревают при 75- 80°С без добавлени ацетилена в течение 3 час. Продукт фильтруют и перегонкой в вакууме выдел ют 5,64 г 1,4 (винилоксиэтил )-амино -бутина-2; т. кип. 181 °С (0,9 ммExample 2. At the stage of formation of di (vinyloxyethyl) propyn-2-ylamine (see Example 1), 5.02 g (0.32 mol) of diethanolamine divinyl ether, 0.96 g (0.032 g) were added to the reaction mass in the autoclave. mol) paraform, 0.1 g CuCl. The mixture is heated at 75-80 ° C without the addition of acetylene for 3 hours. The product is filtered and distillation under vacuum to isolate 5.64 g of 1,4 (vinyloxyethyl) amino-butin-2; m.p. 181 ° С (0,9 mm)
рт. ст.); По 1,4929; ,112; MRo 95,09; вычислено 95,142.Hg Art.); At 1.4929; , 112; MRo 95.09; calculated 95,142.
Найдено, С 65,72; Н 8,61; N 8,15.Found C, 65.72; H 8.61; N 8.15.
Вычислено, %: С 65,9; Н 8,79; N 7,9.Calculated,%: C 65.9; H 8.79; N 7.9.
Возвращают 2,7 г исходного ди-(винилоксиэтил )-пропин-2-иламина и 4,15 г дивинилового эфира диэтаноламина. Конверси 62о/о. Выход 68,1 о/оПредмет изобретени 2.7 g of the starting di- (vinyloxyethyl) -propin-2-ylamine and 4.15 g of divinyl ether of diethanolamine are returned. Conversion 62o / o. Output 68.1 o / o Item of the invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU218141A1 true SU218141A1 (en) |
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