SU799390A1

SU799390A1 - Method of producing potassium salt of bis /1-(4-sulfophenyl)-3-carboxypyrazolon-5/-trimethynoxanine

Info

Publication number: SU799390A1
Application number: SU802871501A
Authority: SU
Inventors: Л.М. Литвиненко; Т.Н. Соломойченко; В.А. Савелова; В.Г. Заславский; Ю.А. Васильев; В.И. Кучерявенко; Н.В. Баранова; А.В. Казымов; Л.Г. Федорина
Original assignee: Институт физико-органической химии и углехимии АН УССР
Priority date: 1980-01-18
Filing date: 1980-01-18
Publication date: 1991-02-23

Abstract

СПОСОБ ПОЛУЧЕНИЯ КАЛИЕВОЙ СОЛИ БИС['1-METHOD FOR OBTAINING POTASSIUM SALT BIS ['1-

Description

Изобретение иллюстрируется следующими примерами.The invention is illustrated by the following examples.

Пример 1. 0,9 г ацетата калия и 1,0 г 1-(4 -сульфофенил)-3-карбоксипиразолона-5 растворяют в 10 мл воды. Затем при 25°С, интенсивно перемешивая раствор, прибавляют 0,51 мл диэтилацеталя β-этоксиакролеина и вццерживают реакционную смесь 15 мин. Для полноты осаждения красителя при перемешивании прикапывают метанол (25 мп), вьщерживают 25 мин и продукт отфильтровывают.Example 1. 0.9 g of potassium acetate and 1.0 g of 1- (4-sulfophenyl) -3-carboxypyrazolone-5 are dissolved in 10 ml of water. Then at 25 ° C, while stirring the solution vigorously, 0.51 ml of β-ethoxyacrolein diethyl acetal is added and the reaction mixture is quenched for 15 minutes. To complete the precipitation of the dye with stirring, methanol (25 mp) is added dropwise, left for 25 minutes and the product is filtered off.

На фильтре краситель промывают метанолом (5 мл). Тщательно отжатую массу высушивают в сушильном шкафу в течение 24 ч.On the filter, the dye is washed with methanol (5 ml). Carefully pressed mass is dried in a drying cabinet for 24 hours

Выход 85,3%. Содержание основного вещества, определенное спектрофотометрическим методом, 99,6%,Yield 85.3%. The content of the basic substance, determined by the spectrophotometric method, 99.6%,

Пр им ер 2. 0,76 г ацетата калия и 0,84 г 1 — (4*-сульфофенил)-3карбоксипиразолона-5 растворяют в 5 мл воды. Затем при 20°,.интенсивно перемешивая раствор, прибавляют 0,51 мп диэтилацеталя р~этоксиакролеина и вьщерживают реакционную смесь 15 мин. Для полноты осаждения красителя при перемешивании прикапывают метанол (10 мп), вьщерживают 25 мин, и продукт отфильтровывают. Далее, как в примере 1.Aper 2. 2. 0.76 g of potassium acetate and 0.84 g of 1- (4 * -sulfophenyl) -3carboxypyrazolone-5 are dissolved in 5 ml of water. Then, at 20 ° C, stirring the solution vigorously, add 0.51 mp of diethyl acetal p ~ ethoxyacrolein and hold the reaction mixture for 15 minutes. To complete the precipitation of the dye with stirring, methanol (10 mp) is added dropwise, left for 25 minutes, and the product is filtered off. Further, as in example 1.

Выход 85,5%, Содержание основного вещества 99,4% (определено спектрофотометрическим способом), ιOutput 85.5%, Content of the main substance 99.4% (determined by spectrophotometric method), ι

Продукт представляет собой мелкокристаллический порошок коричневого цвета. Спектральные свойства: максимум поглощения в воде 539 нм, экстинция 7,640^4-.The product is a brown crystalline powder. Spectral properties: maximum absorption in water 539 nm, extinction 7,640 ^4- .

Предложенный способ позволяет повысить чистоту красителя с 95% до 99,4-99,6%, что является важным в производстве кино- и фотоматериалов, улучшить условия труда за счет снижения температуры процесса с 55-60^вС до 20-25°С и исключения высокотоксичного триэтиламина, сократить длительность конденсации с 4 ч до 15 мин.The proposed method allows to increase the purity of the dye from 95% to 99.4-99.6%, which is important in the production of film and photo materials, to improve working conditions by lowering the process temperature from 55-60 ⁱⁿ C to 20-25 ° C and elimination of highly toxic triethylamine, shorten the duration of condensation from 4 hours to 15 minutes.

Кроме того, предложенный способ позволяет получить краситель с высоким выходом, на 5% превышающим выход красителя по известному способу и сократить расход метанола в 3 раза.In addition, the proposed method allows to obtain a dye with a high yield, 5% higher than the yield of the dye by a known method and reduce the consumption of methanol by 3 times.

Claims

Process for the preparation of potassium salt of bis [Ί ~ (4 ~ -SULFOFENIL) -3-KARBOKSIPIRAZOLON-5] -TRIMETINOKSANINA condensation of 1- (4 -sulfofenil) -3-karboksipirazolona-5 β-etoksiakroleina diethyl acetal followed by methanol precipitation dye, wherein the fact that, in order to improve the quality of the target product while maintaining its yield, improving working conditions of the intensification of the process, condensation is carried out in an aqueous medium in the presence of potassium acetate at 20-25 ° C.

• Ζ *

salt of 1- (4 ⁽ α-sulfophenyl) -3-carboxypyrazolone-5 with β-phenoxyacrolein in absolute methanol in the presence of triethylamine and a 107% methanol solution of potassium acetate at 4050 ° C for 1.5-2 hours, followed by filtration and washing the target product with methanol and acetone.

The resulting dye is purified first by reprecipitation from a water-methanol solution with a 37% methanol solution of potassium acetate, then by recrystallization from methanol.

SC "„ 799390

3,799,390 l

The disadvantages of this method are the complexity of the technological process associated with the need for condensation at elevated temperatures and the use of highly toxic triethylamine and a large amount of methanol, the duration of condensation and the need for an additional purification step for the product, which complicates the process.

Also known is a method of producing a dye, which consists in condensing 1- (4'-sulfophenyl) -3-carboxy-5-15 pyrazolone with β-anilinoacrolein chloride salt in methyl alcohol in the presence of triethylamine at 4850 ° C, followed by cooling the reaction mixture, acidifying her, precipitation of the dye with ethanol or acetone, filtration, washing with ethanol or acetone and drying, the yield and purity of the target product are not specified.

The disadvantages of this method are associated with the complexity of the technology due to the need to carry out the process at elevated temperatures in the presence of highly toxic triethylamine. thirty

The closest to the technical essence of this invention technical solution is a method for producing dye (1) by condensation of 1- (4 * -sulfophenyl) -3-carboxypyrazolone-5 with diethyl acetal β-ethoxyacrolein in methanol in the presence of triethylamine at 55-6C ° С in for 4 h, followed by precipitation of the dye with methanol and purifying its cross-drawing “40

methanol from thallization.

The yield of the target product is 80.6%, purity - 95%.

The disadvantages of this method are the low quality of the dye, which deteriorates the quality of images on film and photo materials, the need to carry out the process at elevated temperatures using highly toxic triethylamine, which worsens working conditions and the duration of the process.

The aim of the invention is to improve the quality of the target product while maintaining its output, improving working conditions and intensification of the process.

This goal is achieved by the fact that in a known way condensation

lead in an aqueous medium in the presence of acetone or potassium at 20-25 ° C.