SU1046239A1 - Process for stabilizing beta-ionone - Google Patents

Description

The invention relates to a method of stabilizing fragrant substances, specifically to a method of stabilizing -io non. (i-ionon 4- (2,6,6-trimethyl-l-cyclohexenyl) -3-butene-2-one) is contained in the essential oil from Boronia megastigma and is the most important component of fragrant substances and perfume compositions. It has a strong analgesic 1 and epithelial 2 action. However, the problem of protecting it from oxidation, the presence of double bonds in the p-ionone molecule has still not been solved, leading to a high oxidation rate of the last GB. The known method of stabilization of fb-ionone is that (b-ionone is injected with a stabilizer hydroquinone 4. However, hydroquinone does not always meet the needs of the industry without providing the necessary storage times for the / ionon. I The disadvantage of using hydroquino is its toxicity is 5 J, which does not allow the use of the latter in C4 fragrant compositions. The purpose of the invention is to increase the shelf life of p-ionone. The goal is achieved by using 0.3-0.9 wt.% 3.5 as a stabilizer. -di-tert-butylpyrocatechol. Stabilization p-Catechine additives are studied using three methods of oxidation. The first method. The oxidation of an ionon is carried out on a gasometric unit to determine the amount of absorbed oxygen. The solution (α-inone in chlorobenzene with a concentration of 0.4 mol / L, containing 0.10, 9% by weight of 3.5 di-tert-butyl pyrocate quina, is placed in a thermostatted cell.The oxidation is carried out with pure oxygen at 60 ° C, atmospheric pressure and vigorous stirring of the solution with a magnetic stirrer. The amount of absorbed oxygen is measured by reducing the volume of oxygen in the gas burette of the installation. At the end of the braking period f, the time is taken, after which 0.02 ml of Og has been absorbed, which is 0.05% of the initial concentration of the p-ionon. The second method. The oxidation is carried out under conditions of accelerated aging, i.e. in a thin layer (layer thickness is about 2 mm). The amount of lb-iono is determined spectrophotometrically (absorption band in the region of 296 nm). The third method. The oxidation is carried out under conditions close to the conditions of natural storage (without solvent, room temperature, sample volume 10 ml). The analysis is similar to the second method. The control is the oxidation of p-ionone with oxygen or oxygen-containing gas in the presence of stabilizing, r-1 additives - known inhibitors of the oxidation of edible fats, such as ionol 2, santohin 3 or without them. Example 1 “According to the first method, a solution of p-ionone in chlorobenzene (4 ml, 0.4 mol / l) is oxidized with oxygen at atmospheric pressure and stirring in the presence of 0.3 wt.% (3,5-di-tert -butylpyrocatechol. The stabilizing effect is also achieved by using compound 1 in amounts of 0.45% and 0.9% by weight (Table 1). Example 2. According to the third method, k / g-ionone (without solvent) 0 is added. 1% by weight of compound 1 and left for long-term storage at room temperature. After b months, the amount of i-ionone left unoxidized is determined by spectrophotometry. The test control was also carried out in the presence of the compound G2J and without a stabilizing additive.The test results are given in Table 3, P p. the thickness of the layer left mm. At the same time, under the same conditions, the same amount of i-ionone is oxidized, but with stabilizer additives. The results are shown in Table 2. The dependence of the oxidation induction period ° C) is shown in table.1. Table 1

3,5-di-tert-butylpyrocatechin 1

4.5

0.3 6.0

0.45 The results of the oxidation of i-ionone in the presence of stabilized additives during storage in a thin layer (can

3,5-Di-tert-butylpyr. Oxidation of p-ion in the presence of stabilizing additives during prolonged storage (concentration 3, 5-Di-tert-butyl pyrocate. Thus, the introduction of the proposed additive contributes to an increase in the oxidation induction period of

qi-ionone 4.88 mol / l, storage time 6 months; are given in table. 3,

Table 3 concentration / i-Aono a 4.88 mol / l additive concentration 0.2 wt.% Is given in table 2. Table 2 bav / ynnogo / 5-ionone at elevated temperature from 15 minutes to 11-12 hours (Table 1) and a decrease in the loss of li-ionone from 32% (when oxidized in the absence of an additive) to 2.5% when oxidized in the presence of 3,5-di-tert-butylpyrocatechin.

The advantage of the proposed method is also the higher efficiency of the stabilizing additive in comparison with hydroquinone. Thus, during the oxidation of J-ionone in the absence of an additive, a polo. Wine of a substance dies in 20 days. In the presence of hydroquinone, 20% of the f-ionone is oxidized over the same period, and in the presence of the proposed 3,5-di-tert-butylpyrocatechine, only 8%, i.e., the effectiveness of the latter is 2.5 times as high.

Thus, the use of the proposed invention allows to increase the storage period of b-ionone by 2.5 times, which is equivalent to an increase in the volume of its production.

In addition, the advantage of this method is the non-toxicity of the stabilizing additive. If hydroquinone, as already mentioned, is a rather toxic compound Sj, then the introduction of a phenolic compound (a pyrocatechin hydroquinone, etc.) into the м 1 molecule of the bulky tert-butyl substituents drastically reduced the toxicity of the compound. Thus, with the introduction of intraperitoneally in Tvine-30 to outbred white mice, di-tert-butylpyrocatechol derivatives were completely non-toxic, and the dose range of 400-800 mg / kg.

Claims (1)

(1> 4) (5?) METHOD FOR STABILIZING β — IONA against thermal oxidative degradation, including the addition of a stabilizer, characterized in that, in order to increase the shelf life, 0.3-0.9 wt.% 3.5 are used as a stabilizer -di-tert-butylpyrocatechol.