SU389072A1 - METHOD OF MANUFACTURING OTHERRANGE Preparation of bisphenols by condensation of phenols with acetylene hydrocarbons. However, only phenyls of the dioxystilbene series and isopropyl'phenol dimers have been studied. The proposed method, based on a known reaction, allows one to obtain new compounds not described by IB - Google Patents

METHOD OF MANUFACTURING OTHERRANGE Preparation of bisphenols by condensation of phenols with acetylene hydrocarbons. However, only phenyls of the dioxystilbene series and isopropyl'phenol dimers have been studied. The proposed method, based on a known reaction, allows one to obtain new compounds not described by IB

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SU389072A1
SU389072A1 SU1676375A SU1676375A SU389072A1 SU 389072 A1 SU389072 A1 SU 389072A1 SU 1676375 A SU1676375 A SU 1676375A SU 1676375 A SU1676375 A SU 1676375A SU 389072 A1 SU389072 A1 SU 389072A1
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USSR - Soviet Union
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bisphenols
otherrange
dioxystilbene
phenyls
phenols
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SU1676375A
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Russian (ru)
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М. Удк
вители Институт нефтехимического синтеза А. В. Топчиева , Московский институт нефтехимической , газовой промышленности Губкина
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Priority to SU1676375A priority Critical patent/SU389072A1/en
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Publication of SU389072A1 publication Critical patent/SU389072A1/en

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40%) биофенола, т. .кип. 210-220°С/5 мм,  вл ющегос  смесью изомеров. При Перекристаллизации «з бензола получают  ,п-изомер в виде мелких кристаллов, т. пл. 143-144°С, выход 25%. Найдено, %: С 79,38; Н 6,19; мол. вес 232. ClgH,402. Вычислено, %: С 79,6; Н 6,2; мол. вес 226. Строение .би-сфенола подтверждено ИК-опектром . Пример 2. Синтез 1,2-быс-(оксифенил)npotneHa-2 . К 0,5 моль (47 г) фенола и 2 г сульфата ртути При 50°С и энергичном перемешивании добавл ют 0,11 моль (6 г) |пр0паргилового спирта и перемешивают 2 час при 50°С. Продукты реакции выдел ют, как в -примере 1. Выход 20%. Пример 3. Синтез 3-метил-1,3-быс-(оксифенил )-бутена-1. К 0,5 моль (47 г) фенола и 1,5 г эфирата фтористого бора ири 90°С и энергичном перемешивании добавл ют 0,1 моль (8,5 г) диметилэтинил1ка1рбоната в смеси с 0,22 моль (20 г) толуола и 0,5 моль (47 г) фенола и ировод т синтез в течение 1,5 час npHr90°C. Продукт реакции выдел ют, как в примере 1, нолуча  бисфенол в виде фракции с т. кип. 225-230°С/5 мм. После перекристаллизащии из бензола получают целевой продукт в виде белых кристаллов, т. пл. 181°С. Выход 55%. Найдено, %: С 80,47; Н 7,18; мол. .вес 256. Ci7Hi8O2. Вычислено, %: С 80,30; Н 7,09; мол. вес 254. Строение бисфенола подтверждено ИК-спекПример 4. Синтез 4-метил-2,4-бис- (окснфенил ) -пенте1на-2. К 0,53 моль (50 г) фенола и 50 г катионита КУ-2 при 90°С и энергичном перемешивании добавл ют 0,1 моль (8,5 г) диметилэтинилкарбинола в смеси с 0,53 моль (50 г) фенола и 0,22 моль (20 г) толуола, за.мен ют капельную воронку на обратный холодильник с ловушкой Дима-Старка и ведут конденсацию при температуре кинени  реакционной смеси () в течение 5-6 час дл  выделени  расчетного количества воды. Продукты отдел ют от катализатора, который дополнительно промывают эфиром, и обрабатывают вышеуказанным способом. Выход бисфенолов 35%Пример 5. Синтез 4-метил-2,4-бмс-(оксифенил )-нентена-2. К 0,585 моль (55 г) фенола и 27 г полифосфорной КИСЛОТЫ при 50°С и энергичном перемешивании дОбавл ют 0,075 моль диметилпропинилкарбйнола в смеси с 0,165 моль (15,5 г) фенола и перемешивают 1 час при 50°С. Продукты реакции выдел ют, как указано выше, и получают бисфенол в виде фракции с т. кип. 218-226°С/5 мм. При перекристаллизации из смеси бензол - гексан получают чистый бисфенол, т. пл. 72°С. Выход 27-30%. Найдено, %: С 80,39; Н 7,22; мол. вес 264. Ci8H2o02. Вычислено, %: С 80,70; Н 7,47; ,мол. вес 268. Строение бисфенола подтверждено ИК-спектром . Предмет изобретени  1.Способ получени  непредельных бисфенолов с двойной св зью в углеводородном мостике , отличающийс  тем, что фенол обрабатывают ацетиленовым спиртом в присутствии катализатора - сульфата ртути или кислотного катализатора, например серной кислоты, или их смеси при 40-100°С с последук щим выделением целевого продукта известными приемами. 2.Способ по п. 1, отличающийс  тем, что процесс ведут в среде органического растворител , например бензола. 3.Способ по пп. 1 и 2, отличающийс  тем, что процесс ведут при мол рном соотношении между фенолом и спиртом 2 : : 1.40%) biophenol, t. Kip. 210-220 ° C / 5 mm, which is a mixture of isomers. Upon recrystallization of “C benzene, the p-isomer is obtained in the form of small crystals, mp. 143-144 ° C, yield 25%. Found,%: C 79.38; H 6.19; a pier weight 232. ClgH, 402. Calculated,%: C 79.6; H 6.2; a pier weight 226. The structure of .bi-sphenol is confirmed by an IR spectrometer. Example 2. Synthesis of 1,2-bys- (hydroxyphenyl) npotneHa-2. To 0.5 mol (47 g) of phenol and 2 g of sulfate of mercury At 50 ° C and vigorous stirring, 0.11 mol (6 g) of <RTI ID = 0.0> p-argyl </ RTI> alcohol is added and stirred for 2 hours at 50 ° C. The reaction products are isolated as in Example 1. Yield 20%. Example 3. Synthesis of 3-methyl-1,3-bys- (hydroxyphenyl) -butene-1. To 0.5 mol (47 g) of phenol and 1.5 g of boron etherate etherate 90 ° C and 0.1 mol (8.5 g) of dimethylethynyl 1 -ka1-carbonate in a mixture with 0.22 mol (20 g) of toluene are added with vigorous stirring and 0.5 mol (47 g) of phenol and ipath synthesis for 1.5 hours npHr90 ° C. The reaction product is isolated as in example 1, but bisphenol in the form of a fraction with m.p. 225-230 ° C / 5 mm. After recrystallization from benzene, the desired product is obtained in the form of white crystals, mp. 181 ° C. Yield 55%. Found,%: C 80.47; H 7.18; a pier .weight 256. Ci7Hi8O2. Calculated,%: C, 80.30; H 7.09; a pier weight 254. The structure of bisphenol is confirmed by IR-spectrum. Example 4. Synthesis of 4-methyl-2,4-bis- (oxnphenyl) -pent1-2. To 0.53 mol (50 g) of phenol and 50 g of the cation exchanger KU-2 at 90 ° C and vigorous stirring are added 0.1 mol (8.5 g) of dimethylethynylcarbinol mixed with 0.53 mol (50 g) of phenol and 0.22 mol (20 g) of toluene, replace the dropping funnel on a reflux condenser with a Dima-Stark trap and condense at the kinani temperature of the reaction mixture () for 5-6 hours to isolate the calculated amount of water. The products are separated from the catalyst, which is further washed with ether, and treated in the above manner. The yield of bisphenols 35% Example 5. Synthesis of 4-methyl-2,4-bms- (hydroxyphenyl) -pentene-2. To 0.585 mol (55 g) of phenol and 27 g of polyphosphoric ACID, at 50 ° C and vigorous stirring, add 0.075 mol of dimethylpropynylcarbynol mixed with 0.165 mol (15.5 g) of phenol and stirred for 1 hour at 50 ° C. The reaction products are isolated, as indicated above, and bisphenol is obtained in the form of a fraction with m.p. 218-226 ° C / 5 mm. Upon recrystallization from a mixture of benzene - hexane, pure bisphenol is obtained, so pl. 72 ° C. The yield is 27-30%. Found,%: C 80.39; H 7.22; a pier weight 264. Ci8H2O02. Calculated,%: C, 80.70; H 7.47; supposedly weight 268. The structure of bisphenol is confirmed by the IR spectrum. The subject of the invention 1. A method for producing double bond unsaturated bisphenols in a hydrocarbon bridge, characterized in that phenol is treated with acetylene alcohol in the presence of a catalyst — mercury sulfate or an acid catalyst, for example sulfuric acid, or a mixture thereof at 40-100 ° C followed by the selection of the target product known techniques. 2. A method according to claim 1, characterized in that the process is conducted in an environment of an organic solvent, for example benzene. 3. Method according to paragraphs. 1 and 2, characterized in that the process is carried out at a molar ratio between phenol and alcohol 2:: 1.

SU1676375A 1971-06-17 1971-06-17 METHOD OF MANUFACTURING OTHERRANGE Preparation of bisphenols by condensation of phenols with acetylene hydrocarbons. However, only phenyls of the dioxystilbene series and isopropyl'phenol dimers have been studied. The proposed method, based on a known reaction, allows one to obtain new compounds not described by IB SU389072A1 (en)

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SU1676375A SU389072A1 (en) 1971-06-17 1971-06-17 METHOD OF MANUFACTURING OTHERRANGE Preparation of bisphenols by condensation of phenols with acetylene hydrocarbons. However, only phenyls of the dioxystilbene series and isopropyl'phenol dimers have been studied. The proposed method, based on a known reaction, allows one to obtain new compounds not described by IB

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SU1676375A SU389072A1 (en) 1971-06-17 1971-06-17 METHOD OF MANUFACTURING OTHERRANGE Preparation of bisphenols by condensation of phenols with acetylene hydrocarbons. However, only phenyls of the dioxystilbene series and isopropyl'phenol dimers have been studied. The proposed method, based on a known reaction, allows one to obtain new compounds not described by IB

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