SU311896A1 - METHOD FOR OBTAINING DI ("- CARBOXYPHENYL) TETRAFTORHYDROCHINON ETHER - Google Patents
METHOD FOR OBTAINING DI ("- CARBOXYPHENYL) TETRAFTORHYDROCHINON ETHERInfo
- Publication number
- SU311896A1 SU311896A1 SU1432459A SU1432459A SU311896A1 SU 311896 A1 SU311896 A1 SU 311896A1 SU 1432459 A SU1432459 A SU 1432459A SU 1432459 A SU1432459 A SU 1432459A SU 311896 A1 SU311896 A1 SU 311896A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carboxyphenyl
- ether
- tetraftorhydrochinon
- obtaining
- tetrafluorohydroquinone
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 4
- ZSDAMBJDFDRLSS-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-diol Chemical compound OC1=C(F)C(F)=C(O)C(F)=C1F ZSDAMBJDFDRLSS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N Hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- -1 tetrafluorohydroquinone ester Chemical class 0.000 description 2
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к способу получени простого фторированного эфира, который может найти применение в синтезе полимеро-в. Известен способ конденсации калиевой соли фенола с галоидбензолом с получением соответствующих эфиров ароматического р да. Предлагаемый способ, использу известные методы органической химии, позвол ет получить неописанные в литературе соединени с повышенной термостойкостью по сравнению с термостойкостью известных соединений. Предлагаемый способ получени ди(п-карбоксифенилового ) эфира тетрафторгидрохинона заключаетс в том, что гексафторбензол подвергают конденсации С избытком калиевой соли л-оксибензойной кислоты прИ кипении в среде пол рного растворител . Полученную реакционную смесь обрабатывают водой , подкисл ют, осадок отфильтровывают, промывают и высушивают. Выход целевого продукта до 67%. Полученное соединение можно перевести в ди.хлорангидрид кислоты путем обработки эфира тетрафторгидрохинона, замешенного карбоксигруппами, п тихлористым фосфором при нагревании до прекрашени выделени хлористого водорода. кипении 2 час, разбавл ют 100 мл воды и подкисл ют сол ной кислотой. Осадок отфильтровывают , промывают водой и сушат. Выход ди-(/г-карбоксифенилового) эфира тетрафторгидрохинона 3,9 г (67%), т. 1ПЛ. 368- 370°С (очистка кислоты возгонкой в вакууме). Д и X л о р а Н г и д р и д кислоты. Смесь 2,9 г и ди-(п-карбоксифенилового) зфира тетрафторгидрохинона, 3,42 г п тихлористого фосфора нагревают при 140-150°С до прекрашени выделени хлористого водорода. Хлорокись водорода отгон ют, в вакууме отгон ют п тихлористый фосфор. Остаток кристаллизуют из гептана. пл. 158-160°С Выход 1,2 г (38%; Найдено, %: С1 15,20, 15,32. С2оН8Р4ОоС12 Вычислено %: С1 15,28. Предмет изобретени Способ получени ди(- 1-карбоксифеиилового ) эфира тетрафторгидрохинона, отличающийс тем, что калиевую соль «-оксибензойной кислоты подвергают конденсации с гексафторбензолом в среде пол рного растворител при температуре кипени реакционной массы с выделением целевого продукта известными приемами.The invention relates to a process for the preparation of a fluorinated ether, which can be used in the synthesis of polymers. A known method of condensation of the potassium salt of phenol with halobenzene to obtain the corresponding aromatic esters. The proposed method, using the known methods of organic chemistry, makes it possible to obtain compounds not described in the literature with increased heat resistance as compared with the heat resistance of known compounds. The proposed method for the preparation of tetrafluorohydroquinone di (p-carboxyphenyl) ether is that hexafluorobenzene is subjected to condensation. With an excess of the potassium salt of l-hydroxybenzoic acid, boiling in a polar solvent. The resulting reaction mixture is treated with water, acidified, the precipitate is filtered off, washed and dried. The yield of the target product to 67%. The compound obtained can be converted to acid d.chloride by treating tetrafluorohydroquinone ester, which is mixed with carboxy groups, with phosphorus chloride and with phosphorus when heated to stop the release of hydrogen chloride. The mixture is boiled for 2 hours, diluted with 100 ml of water and acidified with hydrochloric acid. The precipitate is filtered off, washed with water and dried. The yield of di - (/ g-carboxyphenyl) ether of tetrafluorohydroquinone is 3.9 g (67%), t. 1PL. 368-370 ° C (acid purification by sublimation in vacuum). D and X l about r and H g and d r and d acids. A mixture of 2.9 g and tetrafluorohydroquinone di- (p-carboxyphenyl) zfira, 3.42 g of phosphorus pentachloride is heated at 140-150 ° C until the evolution of hydrogen chloride ceases. Hydrogen oxide is distilled off, and phosphorus pentachloride is distilled off in vacuum. The residue is crystallized from heptane. square 158-160 ° C. Yield: 1.2 g (38%; Found: C1 15.20, 15.32. C2OH8P4OOC12 Calculated%: C1 15.28. Subject of the invention. Method of producing tetrafluorohydroquinone di (-1-carboxyfeiyl) ester, characterized in that the potassium salt of? -oxybenzoic acid is subjected to condensation with hexafluorobenzene in a polar solvent at the boiling point of the reaction mass, with isolation of the target product by known methods.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU311896A1 true SU311896A1 (en) |
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