SU1735293A1 - Method for producing 2-hexyltetrahydrothiophene - Google Patents

Abstract

The invention relates to sulfur-containing heterocyclic compounds, namely to 2-hectyltetrahydrothiophene synthon in the synthesis of the extractant chemical elements. The purpose of the invention is to increase the yield of the target product and simplify the process. The method for preparing 2-hexyltetrahydrothiophene is carried out as follows. A reaction mixture consisting of tetrahydrothiophene hexene-1 and tertiary butylene peroxide in a molar ratio of 4: 1: 0.05-0.1, respectively, is placed in a stainless steel autoclave. The autoclave is kept at 130-150 ° C for 1.5-2.5 hours. After completion of the reaction, the autoclave is cooled and the reaction mixture is subjected to vacuum distillation. 2-hexyltetrahydrotiophen is obtained. The yield is 85-90% versus 50% of the prototype, the synthesis is carried out in one stage and the method is simple in hardware design. 1 tab. cl

Description

This invention relates to a new process for the preparation of 2-hexyltetrahydrothiophene of the formula

SxC6Hn

which is synthon in the synthesis of 2-hexyltetrahydrosulfone extractant for extracting and separating color, rare and trace elements.

A known method for producing 2-hexyltetrahydrothiophene by reacting Na2S with 1,4-dibromodecane in an alcohol solution with heating. The yield of the target product is 50%.

This method has the following disadvantages: a low yield of the target product, the inaccessibility of the original 1,4-dibromodecan, which is synthesized in three stages.

The aim of the invention is to increase the yield of the target product and simplify the process.

This goal is achieved by reacting tetrahydrothiophene with hexene-1 in the presence of tertiary butyl peroxide at a molar ratio of initial reagents equal to 4: 1: 0.05-0.1

Vj

SO 1SL Yu O

J

accordingly, the temperature is 130-150 ° C for 1.5-2.5 hours. The yield is 85- 90%.

EXAMPLE 1 88 g (1 mol) of tetrahydrothiophene, 21 g (0.25 mol) of 1-hexene-1, 11.7 g (0.08 mol) of tertiary butyl peroxide are charged to the autoclave. The reaction mixture is sealed, placed in a thermostat and maintained at a temperature of 130 ° C for 2.5 hours. The autoclave is cooled, the resulting reaction mass is subjected to vacuum distillation. 38.7 g of 2-hexyltetrahydrothiophene are obtained. The yield is 90% on the converted hexene-1. Batch of 92/2 ° С / mm, Po20 1.4843, d420 0.8960. PMR spectrum: 3.17M (1H, CH-cycle); 2.73M (2H, CH2-cycle); 1.86-2.15M (4H "-CH2 cycle); 1.40M (2H CH-CH zam.); 0.84T (3N CH3). Mass spectrum,% of maximum peak: 41 (9.1); 45 (5.7); 65 (5.4); 87 (100.0); 129 (10.4); 172 (11.6).

The remaining examples are tabulated.

From the above examples, it can be seen that the highest yield of 2-hexyltetrahydrothiophene is achieved under the following conditions:

0

five

0

five

the molar ratio of tetrahydrothiophen: hexene 1: PTB 4: 1: 0.05-0.1, temperature 130-150 ° C, reaction time 1.5-2.5 hours. The yield is 90-95%. Outside the specified values (examples 4,5,8,9,12 and 13) the yield of the target product falls.

Compared with the known method of producing 2-hexyltetrahydrothiophene, the proposed method provides a higher yield of the product, the synthesis is carried out in one stage, the method is quite simple in instrumentation.

Claims (1)

Invention Formula The method of producing 2-hexyltetrahydrothiophene, characterized in that, in order to increase the yield of the target product and simplify the process, the tetrahydrothiophene is reacted with 1-hexene in the presence of tertiary butyl peroxide at a molar ratio of starting reagents of 4: 1: 0.05 -0.1 respectively, the temperature of 130-150 ° C for 1.5-2.5 hours