The isolation and purification of n-(hexyloxymethyl)caprolactam

 

(57) Abstract:

The invention relates to a method of isolation and purification N-(hexyloxymethyl)caprolactam (CREPA), with insect - and aerorepublica activity. N-(hexyloxymethyl)caprolactam is produced by interaction of N-methylacetoacetate with excess hexanol in the presence of catalytic amount of concentrated hydrochloric acid. Isolation and purification of akrep is achieved in one stage by boiling the reaction mixture with aqueous alkali at atmospheric pressure with simultaneous distillation of hexanol in the form of an azeotrope with water.

The invention relates to a method of isolation and purification N-(hexyloxymethyl)caprolactam with protecting and aerorepublica activity.

N-(hexyloxymethyl)caprolactam is the technical name for akrep and is a highly effective repellent for protecting humans from the bites of blood-sucking insects and ticks.

Akrep registered for cutaneous application. In this regard, there are restrictions on the content of impurities: the content of caprolactam and hexanol should not exceed 0.5% each (TU 2386-003. 00209266-94).

According to the method of N-(hexyloxymethyl)caprolactam get vzaimodejstvie hydrochloric acid. Next, perform the isolation and purification of the obtained N-(hexyloxymethyl)caprolactam from unreacted caprolactam and excess hexanol. To this reaction mass is diluted with water, neutralized with sodium hydroxide solution and extracted with benzene. The benzene extract was separated and washed with water to dissolve the unreacted caprolactam. Then hold distillation of benzene at atmospheric pressure and the vacuum distillation of hexanol, after which the product is subjected to vacuum distillation.

The disadvantage of this method of isolation and purification of akrep is a large amount of water leaching from equally good solubility of caprolactam in both water and in the organic phase. For more effective cleaning of caprolactam are forced to use benzene, which is highly toxic solvent and applies to flammable liquids. In addition, the vacuum distillation of a significant number of hexanol requires a powerful system to capture relatively low-boiling hexanol-1 to avoid losses. The need for regeneration of benzene and hexanol leads to considerable complication of the technological scheme.

To address these shortcomings Fredericton, and hexanol.

This is achieved by azeotropic distillation of hexanol with water directly from the reaction mass the stage of receiving akrep, excluding the extraction of the organic phase with benzene at atmospheric pressure in the presence of alkali. When using the separation vessel for collecting stratifying the azeotrope hexanol water it becomes possible to return the distillation of water in the reaction mass. When it was unexpectedly found that N-(hexyloxymethyl)caprolactam sustainable boiling with aqueous solutions of alkalis, whereas the caprolactam is hydrolyzed to 6-aminocaproic acid.

Thus, if the reaction mass stage receiving akrep be boiled with aqueous sodium hydroxide solution, the water layer moves the hydrolysis product of caprolactam sodium salt of 6-aminocaproic acid, and hexanol Argonauts in the form of water azeotrope.

The organic layer VAT residue represents the target product - akrep.

The selection of CREPA, thus, is held in one technological stage, boiling of the reaction mixture with odnowionym solution. There is no need for high-vacuum distillation of the final product.

Example. A mixture of 143 g (1 is the significance of 3 hours. Then the reaction mass is neutralized with 0.5 ml of 40% sodium hydroxide solution and washed with 700 ml of water. To the organic layer, add 700 ml of water and 100 ml of 40% aqueous caustic soda solution. The reaction mass is boiled away azeotropic mixture of hexanol with water. After separation of the azeotrope hexanol layer divert and water return in cubic Process is carried out until the content of hexanal and caprolactam <0.5% of each (according to GC).

After the process is finished, the reaction mass is then cooled, the aqueous layer was separated. The organic layer was washed with 1 l of water (with the addition of NaCl) and vacuum drying at a temperature of 60-90oC.

Obtain 205 g of the product containing 97% of the basic substance, 0.4% hexanol, 0.3% caprolactam and 0.5% moisture.

The isolation and purification of N-(hexyloxymethyl)caprolactam obtained by the interaction of the N-methylacetoacetate with excess hexanol, from caprolactam and hexanol, wherein the process is carried out in one stage by boiling the reaction mixture with aqueous alkali at atmospheric pressure with simultaneous distillation of hexanol in the form of an azeotrope with water.

 

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