SU1325047A1 - Method of producing higher alkylimidazolines - Google Patents

Abstract

The invention relates to heterocyclic compounds, in particular to the preparation of higher alkyl imidazolines (AID), intermediates for the synthesis of cationic surfactants. Simplification of the process is achieved by using other reagents that are processed under different conditions. Synthesis of AIS is carried out from the corresponding carboxylic acid and monoethanolamine in the presence of acetonitrile at a molar ratio of 1: 1.1: (2.5-10) at 250-270 ° C and in the presence of zinc chloride or tetrabutylammonium chloride. The method does not require the use of special equipment operating under vacuum, and allows an increase in the AID yield up to 99%. SL 00 to SP 4

Description

one

The invention relates to a method for producing higher alkyl / 1 azolines, which can be used as intermediates for the synthesis of cationic surfactants, corrosion inhibitors.

The purpose of the invention is to simplify the process for producing higher alkyl imidazolines.

The goal is achieved by reacting the corresponding higher carboxylic acid with monoethanolamine in the presence of

acetonitrile at 250-270 C, as a quality, 5 amine 67.1 (1,1); Myristic acid catalyst is used zinc chloride or tetrabutylammonium chloride, and carboxylic acid, acetonitrile and monoethanolamine are taken in a ratio of 1: 2.5-10: 1.1.

Example 1. In an autoclave, made of stainless steel, with a capacity of I l load components, g (mol): acetonitrile D10,5 (10); monoethanol amine 67.1 (1,1); lauric acid 200.3 (1), zinc chloride 3.5. The mixture of reagents is heated and kept at 250 ° C for 1.3 hours, after which the reaction mass is discharged and filtered to separate the catalyst. The filtrate is then transferred to a distillation flask and a light fraction containing g is distilled off: g: acetonitrile 370.5 monoethanolamine 7.6; water 17.6; acetic acid causes a significant improvement in process performance.

on acid 58.5. 218.4 g 2-undecylide c. nolamine (1.1 M) for this synthesis of midazoline (yield 97.5%) and 5 g laury is optimal. An increase in its new acid, remaining in the bottom, is washed on the filter with 50 ml of hexane to remove the acid. The resulting product The proposed method receive has so pl. 81-82 ° C and bk.172-174 / 40 alkylimidazolines with a carbon length of 4 mm Hg. (Literature 82 and 173 chains in the alkyl radical of 8-24 atomic mm Hg, respectively). mov.

Example 2. In the apparatus, analogue. The implementation of the method does not require that the special apparatus described in example 1 is loaded, the components are compressed, g (mol): acetonitrile g operating under vacuum, and allows 410.5 (10) monoethanolamine 67.1 (1.1); achieve yields of alkylimidazolines to caprinic acid 172.3 (G); tetra- 99% for 60-80 minutes. butylammonium chloride 3. The mixture of reagents is heated and maintained at 270 ° C for 1 hour. Then the reaction mass is discharged and filtered to separate the catalyst. The filtrate is transferred to a distillation flask and a light fraction containing g is distilled off, g: acetonitrile, 370.03; monoethanolamine 6.95; water 17.75; acetic acid 59,16. 193.3 g of 2-nonylimidazoline (98.6% yield) and 2.41 g of caproic acid remaining in the bottom are washed

Claims (2)

Invention Formula 50 A method of producing higher alkylimidazolines by reacting the corresponding higher aliphatic carboxylic acid with an amine with heating. 55 in the presence of a catalyst, characterized in that, in order to simplify the process technology, monoethanolamine is used as the amine and the process is carried out in the presence of 30A7 on the filter 50 ml of hexane for beats; acid acids. The resulting product has a mp. 71 ° C and a bp. 160-162 ° C / 8mmHg , (lit. 71 and 161-162 C / 8 mm Hg, respectively). When the amount of the starting acetonitrile is reduced four times, a decrease in the yield of alkylimide Q dazoline by 25Z is observed. Example2. The autoclave, made of stainless steel, with a capacity of 1 l load the components, g / mol: acetonitrile 102,63 (2,5); monostanolta 228.38 (1); zinc chloride 2. The mixture of reagents is heated and maintained at 250 C for 1.3 hours, after which the reaction mass is discharged and filtered to separate the catalyst. Then, the filtrate is transferred to a distillation flask and a light fraction of C, containing, g; acetonitrile 71.43; monosanolamine 20.74; water 13.68; acetic acid 45.6. 191.52 g of 2-tridecylimidazoline (76% yield) and 54.8 g of myristic acid remaining in the bottom are washed on the filter with 200 ml of hexane to remove the acid. The resulting product has so pl. 87-88 C and so Kip. 178-180 ° / 2 mm Hg (lit. data 87-88 and 179-180 C / 2 mm Hg, respectively). The molar ratio for monoethane causes a significant improvement in process performance. nolamine (1.1 M) for this synthesis is optimal. Increasing it by the proposed method is obtained by alkyl imidazolines with a carbon chain length in the alkyl radical of 8-24 atoms.  The implementation of the method does not require the use of special equipment operating under vacuum, and allows yields of alkylimidazolines up to 99% within 60-80 minutes. Invention Formula  The implementation of the method does not require the use of special equipment g operating under vacuum, and allows yields of alkylimidazolines up to 99% within 60-80 minutes. A method of producing higher alkylimidazolines by reacting the corresponding higher aliphatic carboxylic acid with an amine with heating. 55 in the presence of a catalyst, characterized in that, in order to simplify the process technology, monoethanolamine is used as the amine and the process is carried out in the presence of  1325047 acetonitrile at 250-270 ° C and mol p-10: 1.1, and carboxylic acid as a catalyst; Zinc chloride or tetra-: acetonitrile: monoethanolamine 1: 2.5 - butylammonium chloride is used.