RU1781207C - Process for producing 0-nitrosoaniline - Google Patents

Abstract

Usage 1 Preparation of semiconductors for fine organic synthesis. The creature is invented. Reagent 1: o-phenylenediamine, B. F. Sat. Reagent 2: hydrogen peroxide, B F. H2U2 (30% solution), Reaction conditions: temperature 5-10 ° C, medium ethanol, catalyst molybdis sodium; the molar ratio of phenylenediamine is hydrogen peroxide: molybdate Na ethyl alcohol 1: 4: 5.1: 0.024.

Description

The invention relates to the field of synthesis of an organic compound of formula 1

OS

NH7 N0

which is used for the synthesis of quinoxaline series compounds used as acaricidal and nematicidal preparations

Until now, there was no technological method for the production of nitrosoaniline, which prevented its widespread use in production. This compound was first isolated as a by-product by heating benzofuroxane with triphenylphosphigum

Closest to the proposed one is a method for preparing the base of rosoyaylin by oxidation of o-phenylenediamine with potassium peroxide. The yield in the atom of the case was 38%. In this work, the synthesis of o-nitrosoaniline was carried out in an inert atmosphere, at 25 ° С, with the presence of 18-crown-6-ether. In this case, o-nitroaniline (28%) and 2,2-diaminoazobenzene were obtained as the main by-products (26%), which forced the clasters to apply the chromato-haphic method of separation of products. An attempt to simplify this method was unsuccessful. Tek when passing oxygen through a benzene solution of o-phzchylenediamine in the presence of KOH led to a 10% yield of o-nitrosoaniline. Thus, this method is not technological because the synthesis conditions are used specifically (inert atmosphere, the presence of crown ether) and the formation of by-products from which can only be separated by chromatography

The aim of the present invention is to increase the yield and to create a new, more technologically advanced method for the synthesis of nitrosoaniline. This goal is achieved by the fact that 30% hydrogen peroxide is used as an oxidite and the process is carried out in ethanol in the presence of sodium molybdate at a temperature of 5-10 ° C and a molar ratio of phenylenediamine, hydrogen peroxide of sodium molybdate and ethyl alcohol 1: 4-0.024 5 ,1.

PRI me R 1. Obtaining o-nitrosoznil and n and.

1.08 g (0.01 m) of o-phenklendiimine is dissolved in 30 ml of alcohol, and with vigorous stirring at a temperature of 5-10 ° C, 0.05 g of Na2Mo04 dissolved in a 2 are added.

YU

ml of 30% hydrogen peroxide. After that, the reaction mixture was kept for 6 hours at the indicated temperature, poured into 200 ml of water and extracted with ether. The ether extract is washed with 0.01 N. 5 with HCI and the ether was evaporated. Obtain 0.62 g (52%) of o-nitrosoaniline Tm. 78 ° C, mp. 78 S.

Driven by the effect of quantitative

Peroxide

hydrogen 2.1 ml (0.04 mol)

The optimum reaction time is 6 hours.

Claims (1)

The claims A method of producing o-nitrosoaniline by oxidation of o-phenylenediamine reagents to achieve the goal with 10 acidic compounds, and the oxidation of o-phenylenediamine with peroxide so that, in order to increase the yield of target hydrogen in the presence of sodium molybdate product and simplification of technology, in (tab. 1-4). As an oxidizing agent use 30% As can be seen from the table. 1,2,3 optimal hydrogen peroxide, and the process is conducted in a medium containing reagents containing 0.01 mol of о-фе-15 ethyl alcohol in the presence of nylenediamine molybdate and sodium at 5-10 ° С and a molar ratio of Ethyl alcohol of 30 ml (0, 51 mol) of phenylenediamine, hydrogen peroxide, Sodium Molybdate Molybdate and Ethyl Alcohol sodium 0.05 g mol) 1: 4: 0.024: 5.1. Table 1 The effect of temperature, hydrogen peroxide concentration, and the amount of solvent (alcohol) on the yield of o-nitrosoaniline. Peroxide hydrogen 2.1 ml (0.04 mol) The optimum reaction time is 6 hours. The claims Table 2 The effect of the amount of sodium molybdate on the output of o-nitrosoaniline Table 3 The effect of the amount of hydrogen peroxide on the output of o-nitrosoaniline Effect of reaction time on the yield of o-nitrosoaniline Table 4