SU1824389A1 - 2,4,5-trimethylbenzene-1,3-dicarbaldehyde used as intermediate product in synthesis of 2,4,5-trimethylbenzene-1,3-dinitriloxide, low-temperature curing agent for rubber-based polymer materials - Google Patents

2,4,5-trimethylbenzene-1,3-dicarbaldehyde used as intermediate product in synthesis of 2,4,5-trimethylbenzene-1,3-dinitriloxide, low-temperature curing agent for rubber-based polymer materials Download PDF

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SU1824389A1
SU1824389A1 SU914930157A SU4930157A SU1824389A1 SU 1824389 A1 SU1824389 A1 SU 1824389A1 SU 914930157 A SU914930157 A SU 914930157A SU 4930157 A SU4930157 A SU 4930157A SU 1824389 A1 SU1824389 A1 SU 1824389A1
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trimethylbenzene
dicarbaldehyde
synthesis
low
dinitriloxide
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SU914930157A
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Russian (ru)
Inventor
Lidiya I Samaraj
Viktor I Gorbatenko
Nina V Melnichenko
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Inst Orch Khim An Ussr
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Description

Изобретение относится к 2,4,5-триметилбензол-1,3-дикарбальдегиду формулы (I) в качестве промежуточного продукта для синтеза 2,4,5-триметилбензол-1,3-динитрилоксида формулы (II) - эффективного низкотемпературного отвердителя полимерных материалов на основе каучуков.The invention relates to 2,4,5-trimethylbenzene-1,3-dicarbaldehyde of the formula (I) as an intermediate for the synthesis of 2,4,5-trimethylbenzene-1,3-dinitrile oxide of the formula (II), an effective low-temperature hardener of polymeric materials on rubber based.

сн3 сн3 sun 3 sun 3

O=CH-^-CH3 O”-N=C-^-CH3 сн3 СН =о сн3 С=М-*О Целью изобретения является поиск путей синтеза новых исходных соединений для получения динитрилоксида формулы (II).O = CH - ^ - CH 3 O ”-N = C - ^ - CH 3 sn 3 CH = о sn 3 С = М- * О

Поставленная цель достигается предложенным ароматическим дикарбальдегидом формулы (I).This goal is achieved by the proposed aromatic dicarbaldehyde of the formula (I).

Изобретение иллюстрируется следующим примером.The invention is illustrated by the following example.

Пример. 2,4,5-Триметилбензол-1,3дикарбальдегид (I).Example. 2,4,5-Trimethylbenzene-1,3dicarbaldehyde (I).

К суспензии 72 г (0,4 мол) 1,3-бис(оксиметил)-2,4,5-триметилбензола в 1,5 л воды прибавляют 250 мл 25%-ного раствора серной кислоты. Затем при перемешивании небольшими порциями раствор 57 г (0,57 мол) окиси хрома СгОз в 100 мл воды. Реакционную смесь подогревают.до 40°С. после этого она самопроизвольно нагревается до 5255°С. Перемешивание продолжают до начала падения температуры (20-30 мин), после чего реакционную массу быстро охлаждают до 20°С. Осадок отфильтровывают, промывают на фильтре сначала 5%-ным раствором NaOH (около 500 мл), затем водой до нейтральной реакции. Полученный сырой продукт по данным ЖХ анализа содержит 65-70% основного продукта (в расчете на сухое вещество) и без дополнительной очистки может быть направлен на следующие стадии получения динитрилоксида (II). Для очистки диальдегида (I) сырой продукт обрабатывают 500 мд, эфирную вытяжку сушат над СаС1г. после упаривания растворителя получают соединение (I) с содержанием основного вещества 97% по данным ЖХ анаTo a suspension of 72 g (0.4 mol) of 1,3-bis (oxymethyl) -2,4,5-trimethylbenzene in 1.5 L of water, 250 ml of a 25% solution of sulfuric acid are added. Then, with stirring in small portions, a solution of 57 g (0.57 mol) of chromium oxide CrO3 in 100 ml of water. The reaction mixture is heated to 40 ° C. after that, it spontaneously heats up to 5255 ° C. Stirring is continued until the temperature drops (20-30 minutes), after which the reaction mass is rapidly cooled to 20 ° C. The precipitate is filtered off, washed on the filter, first with a 5% NaOH solution (about 500 ml), then with water until neutral. The obtained crude product according to LC analysis contains 65-70% of the main product (calculated on the dry matter) and without further purification can be sent to the following stages for the production of dinitrile oxide (II). To purify dialdehyde (I), the crude product is treated with 500 ppm, the ether extract is dried over CaCl. after evaporation of the solvent, compound (I) is obtained with a basic substance content of 97% according to LC ana

1824389 А1 лиза. Выход диальдегида (I) 63%. Т.,пл. 7072°С, ИК-спектр (СНС1з. см-1): 1700 (С=О). Найдено. %: С 75,31, Н 6,83. С11Н12О2.·Вычислено, %: С 74,98; Н 6,86.1824389 A1 Lisa. The yield of dialdehyde (I) 63%. T., pl. 7072 ° C, IR spectrum (CHC1.s. cm -1 ): 1700 (C = O). Found. %: C 75.31, H 6.83. С11Н12О2. · Calculated,%: С 74.98; H, 6.86.

Соединение (I) - бесцветное кристаллическое вещество, растворимое в большинстве органических растворителей, трудно . растворяется в гексане, не растворяется в воде. 10Compound (I), a colorless crystalline substance soluble in most organic solvents, is difficult. soluble in hexane, insoluble in water. 10

Таким образом, синтезированный препаративно простым и технологичным способомThus synthesized preparatively simple and technologically advanced way

2,4,5-триметилбензол-1,3-дикарбальдегид формулы (I) служит исходным материалом для получения важного в практическом пла не продукта - 2.4,5-триметилбензол-1,3-динитрилоксида формулы (II).2,4,5-trimethylbenzene-1,3-dicarbaldehyde of the formula (I) serves as a starting material for the production of an important product in practice - 2.4,5-trimethylbenzene-1,3-dinitrile oxide of the formula (II).

Claims (2)

Формула изобретенияClaim 2,4,5-Триметил бензол-1,3-дикарбальдегид формулы в качестве промежуточного продукта для синтеза 2,4,5-триметилбензол-1,3-динитрилоксида - низкотемпературного отвердителя полимерных материалов на основе 15 каучуков.2,4,5-Trimethylbenzene-1,3-dicarbaldehyde of the formula as an intermediate for the synthesis of 2,4,5-trimethylbenzene-1,3-dinitrile oxide, a low-temperature hardener of polymeric materials based on 15 rubbers. Редактор Т.Ходакова Editor T. Khodakova Составитель В.Горбатейко Техред М.Моргентал Корректор С.Лисина Compiled by V. Gorbateyko Tehred M. Morgenthal Corrector S. Lisina
Заказ 2213 Тираж ПодписноеOrder 2213 Circulation Subscription ВНИИПИ Государственного комитета по изобретениям и открытиям при ГКНТ СССР ·VNIIIPI of the State Committee for Inventions and Discoveries under the State Committee for Science and Technology of the USSR · 113035, Москва, Ж-35, Раушская наб., 4/5113035, Moscow, Zh-35, Raushskaya nab., 4/5 Производственно-издательский комбинат Патент, г. Ужгород, ул.Гагарина. 101Production and Publishing Plant Patent, Uzhhorod, Gagarin St. 101
SU914930157A 1991-04-22 1991-04-22 2,4,5-trimethylbenzene-1,3-dicarbaldehyde used as intermediate product in synthesis of 2,4,5-trimethylbenzene-1,3-dinitriloxide, low-temperature curing agent for rubber-based polymer materials SU1824389A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6252009B1 (en) 1999-02-24 2001-06-26 The Goodyear Tire & Rubber Company Process for curing acrylic polymers
US6355826B1 (en) 1997-09-17 2002-03-12 The Goodyear Tire & Rubber Company Synthesis of stable nitrile oxide compounds
RU2694261C1 (en) * 2018-04-23 2019-07-11 Общество с ограниченной ответственностью "Институт по проектированию производств органического синтеза" Method of producing di-n,n'-oxides of 2,4,6-trialkylbenzene-1,3-dicarboxylic acid dinitriles

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6355826B1 (en) 1997-09-17 2002-03-12 The Goodyear Tire & Rubber Company Synthesis of stable nitrile oxide compounds
US6252009B1 (en) 1999-02-24 2001-06-26 The Goodyear Tire & Rubber Company Process for curing acrylic polymers
RU2694261C1 (en) * 2018-04-23 2019-07-11 Общество с ограниченной ответственностью "Институт по проектированию производств органического синтеза" Method of producing di-n,n'-oxides of 2,4,6-trialkylbenzene-1,3-dicarboxylic acid dinitriles

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