SU338519A1 - METHOD OF OBTAINING 1-ACETYL CHLOROPRENE - Google Patents
METHOD OF OBTAINING 1-ACETYL CHLOROPRENEInfo
- Publication number
- SU338519A1 SU338519A1 SU1457424A SU1457424A SU338519A1 SU 338519 A1 SU338519 A1 SU 338519A1 SU 1457424 A SU1457424 A SU 1457424A SU 1457424 A SU1457424 A SU 1457424A SU 338519 A1 SU338519 A1 SU 338519A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloroprene
- acetyl
- obtaining
- chloride
- acetylchloroprene
- Prior art date
Links
- YACLQRRMGMJLJV-UHFFFAOYSA-N Chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 title description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N Chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000001588 bifunctional Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к получению 1-ацетилхлоропрена , пригодного дл получени полимеров и сополимеров, а также дл синтеза физиологически активных веществ. Способ получени 1-ацетилхлоропрена неизвестен . Указанное соединение не описано пи в патентной, ни в журнальной литературе. Предлагаемый способ основан на известной реа.кции ацетилхлорида в присутствии катализатора Фридел -Крафтса с олефинами среде органического растворител . Целью изобретени вл етс расширение ассортимента бифункциональных мономеров. По предлагаемому способу хлоропрен обрабатывают ацетилхлородом в присутствии катализатора Фридел -Крафтса при температуре (-50) - (-20) °С с последующим выделением целевого продукта известным методом. Желательно процесс проводить в среде органического растворител . Пример 1. В четырехтубусную круглодонную колбу, снабженную механической мещалкой , обратным холодильником, термометром и капельной воронкой, помещают 39,5 г (0,5 моль) ацетилхлорида, растворенного в 50 мл четыреххлористого углерода. При охлаждении к смеси прибавл ют 67 г (0,5 моль) хлористого алюмини так, чтобы температура смеси не была выше -5°С. Затем при (-5) - (-8) °С в течение 3 час прибавл ют 44 г ( 0,5 моль) хлоропрена. После чего содержание колбы обрабатывают смесью сол ной кислоты , эфира и льда. 1-Ацетилхлоропрен экстрагируют эфиром, промывают водой и 10%-ным раствором соды, высушивают хлористым кальцием, отгон ют эфир, а остаток разгон ют в вакууме. Выдел ют 34 г (52%) 1-ацетилхлоропрепа, т. кип. 65°С/Ьмм-по 1,5090,4° 1,1262. С 54,82; Н 6,03; С1 25,68; Найдено, %: MRn 34,57. С 55,17; Н 5,36; С1 27,21; Вычислено, % MRD 33,86. с.и-1): 3065; ИК-спектр (в 1646; С 0 1724. Пример 2. В услови х примера 1 реакцию провод т в метиленхлориде. Выход 1-ацетилхлоропрена 28,5%. Предмет и з о б р е т е « и 1.Способ получени 1-ацетилхлороирена, отличающийс тем, что хлоропреи подвергают взаимодействию с хлористым ацетилхлоридом в присутствии катализатора Фридел -Крафтса при температуре (-50) -(-20) °С, с последующим выделением целевого продукта известным методом.The invention relates to the preparation of 1-acetylchloroprene, suitable for the preparation of polymers and copolymers, as well as for the synthesis of physiologically active substances. The method of producing 1-acetylchloroprene is unknown. The specified connection is not described pi in the patent or in the journal literature. The proposed method is based on the known reactivation of acetyl chloride in the presence of a Friedel-Crafts catalyst with olefins in an organic solvent medium. The aim of the invention is to expand the range of bifunctional monomers. According to the proposed method, chloroprene is treated with acetyl chloride in the presence of the Friedel-Crafts catalyst at (-50) - (-20) ° C, followed by separation of the target product by a known method. It is desirable to carry out the process in the environment of an organic solvent. Example 1. In a four-tube round-bottomed flask equipped with a mechanical baffle, reflux condenser, thermometer, and addition funnel, 39.5 g (0.5 mol) of acetyl chloride dissolved in 50 ml of carbon tetrachloride are placed. While cooling, 67 g (0.5 mol) of aluminum chloride was added to the mixture so that the temperature of the mixture was no higher than -5 ° C. Then at (-5) - (-8) ° C, 44 g (0.5 mol) of chloroprene is added over 3 hours. After that, the contents of the flask are treated with a mixture of hydrochloric acid, ether and ice. 1-Acetylchloroprene is extracted with ether, washed with water and 10% soda solution, dried with calcium chloride, the ether is distilled off, and the residue is distilled in vacuo. 34 g (52%) of 1-acetylchloroprep, i.e., kip was isolated. 65 ° С / Ьмм-by 1.5090.4 ° 1.1262. C, 54.82; H 6.03; C1 25.68; Found%: MRn 34.57. C 55.17; H 5.36; C1, 27.21; Calculated% MRD 33.86. s.i-1): 3065; IR spectrum (in 1646; C 0 1724. Example 2. Under the conditions of example 1, the reaction was carried out in methylene chloride. The yield of 1-acetyl chloroprene was 28.5%. Subject and concern were "1. Preparation Method 1 -acetylchloroirene, characterized in that the chloroprenium is reacted with acetyl chloride in the presence of the Friedel-Crafts catalyst at (-50) - (- 20) ° C, followed by isolation of the target product by a known method.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU338519A1 true SU338519A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4560791A (en) * | 1982-09-30 | 1985-12-24 | International Flavors & Fragrances Inc. | Synthesis of triconjugated dienones and intermediates used in said process |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4560791A (en) * | 1982-09-30 | 1985-12-24 | International Flavors & Fragrances Inc. | Synthesis of triconjugated dienones and intermediates used in said process |
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