A method for increasing conversion of ethyl vanillin-beta-d-glucoside in sidestream smoke

Abstract

The present application belongs to the technical field of tobacco, and discloses a method for improving the conversion rate of ethyl vanillin-beta-D-glucoside in sidestream smoke. In the method, ethyl vanillin-beta-D-glucoside and a certain amount of intumescent flame retardant are mixed and then added to the combustion position of a cigarette. The method can significantly improve the conversion rate of ethyl vanillin-beta-D-glucoside in sidestream smoke into ethyl vanillin.

Description

Technical Field

[0001] This invention belongs to the field of tobacco technology, and specifically relates to a method for improving the conversion rate of ethyl vanillin-β-D-glucoside in sidestream smoke. Background Technology

[0002] Adding flavoring to cigarettes is quite complex. A cigarette stick consists of burning parts such as tobacco and cigarette paper, non-burning parts such as the filter, and mouth-contact parts such as the tobacco tow and binding paper. The intensity of the flavorings and fragrances added to different parts of the cigarette stick will vary depending on the consumer's sense of smell and taste. If flavorings and fragrances are added to cigarettes at inappropriate locations, it can lead to low utilization rates, short-lasting aroma, low flavoring efficiency, or even no flavoring effect at all. Currently, determining the optimal location or method for adding flavorings and fragrances to cigarettes to maximize their effect mainly relies on the experience of product developers and repeated smoking tests, which is time-consuming and labor-intensive. CN114903206A discloses a method for determining the addition method of synthetic sweeteners in cigarettes. This method determines the addition method of synthetic sweeteners in cigarettes based on their thermal decomposition temperature and boiling point. Based on the boiling point of synthetic sweeteners, this method provides theoretical guidance and a basis for the precise addition of flavorings and fragrances. Aside from sensory experience, there is currently no objective theoretical basis or method for determining how to efficiently use EVG in cigarettes.

[0003] Patent US0555599 describes the addition of ethyl vanillin-β-D-glucoside (EVG) to cigarette paper to create flavored cigarettes. These cigarettes have no milky aroma before smoking, but a milky aroma can be smelled during smoking. This milky aroma is actually the aroma of ethyl vanillin. Anhui Agricultural Sciences, 2012, 40(6):3562-3564 conducted research on the application of ethyl vanillin in low-tar cigarettes and found that it has an aroma compensation effect. Chemical Industry Management, 2019, (14):20-22 synthesized ethyl vanillin-β-D-glucoside and used a thermal decomposition-GC / MS system to conduct targeted thermal decomposition analysis at 250℃, 300℃, 400℃, 600℃, and 900℃. The results showed that the aroma substances produced by the pyrolysis of this glycoside gradually increased with the increase of heating temperature. These aroma substances endow tobacco with a rich sweet aroma and enhance its fragrance. Patent CN108445105A established and further optimized a method for detecting ethyl vanillin-β-D-glucoside in cigarette paper.

[0004] When cigarettes are smoked, the aroma in the mainstream smoke provides a pleasant smell for the smoker, while the aroma in the sidestream smoke provides a pleasant smell for non-smokers in the surrounding area, creating a better environment for them. CN113100469A discloses the contribution of EVG addition methods to the aroma in both the main and sidestream smoke. EVG itself has no aroma, but a milky aroma can be smelled when inhaled; this milky aroma is actually the aroma of ethyl vanillin. In actual tobacco consumption, a higher content of ethyl vanillin in the sidestream smoke can bring a greater sense of pleasure to both the smoker and the surrounding non-smokers. Therefore, improving the conversion rate of EVG in sidestream smoke is a problem that needs to be solved.

[0005] In view of this, the present invention is hereby proposed. Summary of the Invention

[0006] This invention proposes a method to improve the conversion rate of EVG to ethyl vanillin in side-flow flue gas, in order to solve the current problems of precise EVG flavoring and EVG conversion rate.

[0007] The technical solution of the present invention is as follows:

[0008] A method for improving the EVG conversion rate in sidestream flue gas involves mixing EVG with a certain amount of intumescent flame retardant and adding the mixture to the combustion section of a cigarette.

[0009] Preferably, the intumescent flame retardant is ammonium polyphosphate.

[0010] Preferably, the amount of EVG added to a cigarette is 0.2–0.8 mg / cigarette.

[0011] Preferably, the amount of ammonium polyphosphate added is such that its mass ratio to the added EVG is 1:(0.5-3.0).

[0012] Preferably, the burning part is tobacco and / or cigarette paper.

[0013] The beneficial effects of this invention are:

[0014] This invention involves mixing a certain amount of intumescent flame retardant and EVG and adding it to the tobacco and / or cigarette paper in the combustion section of a cigarette. This significantly increases the EVG content in the sidestream smoke, thereby significantly improving the conversion rate of EVG to ethyl vanillin in the sidestream smoke. When the amount of EVG added to the cigarette is less than 0.2 mg / cigarette, the increase in the EVG conversion rate in the sidestream smoke is not significant; when the amount of EVG added to the cigarette is greater than 0.8 mg / cigarette, the conversion rate of EVG to ethyl vanillin in the sidestream smoke decreases. When the mass ratio of ammonium polyphosphate to added EVG is greater than 2:1, the increase in the conversion rate of EVG to ethyl vanillin in the sidestream smoke is not significant; when the mass ratio of ammonium polyphosphate to added EVG is less than 1:3, the effect of ammonium polyphosphate is not significant, and the increase in the conversion rate of EVG to ethyl vanillin in the sidestream smoke is also not significant. Attached Figure Description

[0015] Figure 1 This is a schematic diagram of EVG combustion or thermal decomposition. Detailed Implementation

[0016] The technical solutions of the present invention are described in detail below through embodiments. These embodiments are merely exemplary and can only be used to explain and illustrate the technical solutions of the present invention, and should not be construed as limiting the technical solutions of the present invention. In the embodiments of this application, unless specific technologies or conditions are specified, they are carried out in accordance with existing technologies or conditions in the field. Materials or equipment whose manufacturers are not specified are all conventional products that can be obtained by purchase.

[0017] Comparative Example 1: Conversion rate of EVG in main and sidestream flue gas

[0018] EVG solution was uniformly added to cigarette tobacco and cigarette paper using a flavoring injection machine, with 0.2 mg, 0.4 mg, and 0.8 mg of EVG added to each cigarette, respectively. The cigarettes were smoked under standard conditions using an RM200 20-channel automatic smoking machine. Particulate matter in the mainstream smoke was captured using a 44 mm Cambridge filter. Ethyl vanillin was extracted from the Cambridge filter three times (15 mL each time) using dichloromethane as the extractant. The extracts were combined, moderately concentrated, transferred to a 10 mL volumetric flask, and diluted to the mark with chromatographic dichloromethane. After filtration, the sample solution was obtained. The concentration and content of EVG in the sample were calculated based on the standard curve, and the conversion rate of EVG to EVG in the mainstream smoke was calculated, as shown in Table 1.

[0019] Table 1. Conversion rate of EVG to ethyl vanillin in mainstream flue gas

[0020]

[0021] As shown in Table 1, when EVG is added to tobacco, the conversion rate of EVG to ethyl vanillin in mainstream smoke is relatively high, with conversion rates of 1.38%, 1.25%, and 1.49% at the three dosage levels, respectively. Table 1 also shows that when EVG is added to cigarette paper, the conversion rate of EVG to ethyl vanillin in mainstream smoke is relatively low.

[0022] The conversion rate of EVG to ethyl vanillin in the sidestream flue gas was calculated and is shown in Table 2.

[0023] Table 2. Conversion rate of EVG to ethyl vanillin in sidestream flue gas

[0024]

[0025] As shown in Table 2, when EVG is added to cigarette paper, the conversion rate of EVG to ethyl vanillin in the sidestream smoke is relatively high, with conversion rates of 4.32%, 5.12%, and 6.75% at the three dosage levels, respectively. Table 2 also shows that when EVG is added to tobacco shreds, the conversion rate of EVG to ethyl vanillin in the sidestream smoke is relatively low.

[0026] Example 1: Effect of ammonium polyphosphate on the conversion rate of EVG to ethyl vanillin in mainstream flue gas and the effect of ammonium polyphosphate on the conversion rate of EVG to ethyl vanillin in sidestream flue gas.

[0027] A 1:1 mass ratio mixture of EVG and ammonium polyphosphate was uniformly added to cigarette tobacco and cigarette paper using a flavoring injection machine, with 0.4 mg of EVG added to each cigarette. The cigarettes were smoked under standard conditions using an RM200 20-channel automatic smoking machine. Particulate matter in the mainstream smoke was captured using a 44 mm Cambridge filter. Ethyl vanillin was extracted from the Cambridge filter three times (15 mL each time) using dichloromethane as the extractant. The extracts were combined, moderately concentrated, transferred to a 10 mL volumetric flask, and diluted to the mark with chromatographic dichloromethane. After filtration, the sample solution was obtained. The concentration and content of ethyl vanillin in the sample were calculated based on the standard curve, and the conversion rate of EVG to ethyl vanillin in the mainstream smoke was calculated, as shown in Table 3.

[0028] Table 3. Conversion rate of EVG to ethyl vanillin in mainstream flue gas

[0029]

[0030] As shown in Table 3, a 1:1 mass ratio mixture of EVG and ammonium polyphosphate was uniformly added to cigarette tobacco and cigarette paper, respectively, with 0.4 mg of EVG added per cigarette. The conversion rates of ethyl vanillin in the EVG from the two types of EVG were 0.87% and 0.46%, respectively. Compared with Comparative Example 1 (see Table 1), the addition of ammonium polyphosphate reduced the conversion rate of EVG to ethyl vanillin in mainstream smoke when added to tobacco; similarly, the addition of ammonium polyphosphate also reduced the conversion rate of EVG to ethyl vanillin in mainstream smoke when added to cigarette paper. This indicates that the addition of ammonium polyphosphate reduces the conversion rate of EVG to ethyl vanillin in mainstream smoke, regardless of whether the EVG is added to tobacco or cigarette paper.

[0031] The conversion rate of EVG to ethyl vanillin in the side-flow flue gas was measured and is shown in Table 4.

[0032] Table 4. Conversion rate of EVG to ethyl vanillin in sidestream flue gas

[0033]

[0034] As shown in Table 4, a 1:1 mass ratio mixture of EVG and ammonium polyphosphate was uniformly added to cigarette tobacco and cigarette paper, with 0.4 mg of EVG added per cigarette. The conversion rates of EVG to ethyl vanillin for both types of cigarettes were 4.98% and 7.19%, respectively. It can be seen that, compared to Comparative Example 1 (see Table 2), the addition of ammonium polyphosphate increased the conversion rate of EVG to ethyl vanillin in the sidestream smoke for both the tobacco and cigarette paper. This indicates that the addition of ammonium polyphosphate increases the conversion rate of EVG to ethyl vanillin in the sidestream smoke, regardless of whether the EVG is added to tobacco or cigarette paper.

[0035] Comparative Example 2: The effect of the amount of EVG added after the addition of ammonium polyphosphate on the conversion rate of EVG to ethyl vanillin in mainstream flue gas and the effect of the amount of EVG added on the conversion rate of EVG to ethyl vanillin in sidestream flue gas.

[0036] A 1:1 mass ratio mixture of EVG and ammonium polyphosphate was uniformly added to cigarette tobacco and cigarette paper using a flavoring injection machine, with 0.1 mg of EVG and 0.1 mg of ammonium polyphosphate added to each cigarette. The cigarettes were smoked under standard conditions using an RM200 20-channel automatic smoking machine. Particulate matter in the mainstream smoke was captured using a 44 mm Cambridge filter. Ethyl vanillin was extracted from the Cambridge filter three times (15 mL each time) using dichloromethane as the extractant. The extracts were combined, moderately concentrated, transferred to a 10 mL volumetric flask, and diluted to the mark with chromatographic dichloromethane. The solution was then filtered to obtain the sample solution. The concentration and content of ethyl vanillin in the sample were calculated based on the standard curve. The conversion rate of EVG to ethyl vanillin in the main sidestream smoke was also calculated, as shown in Tables 5 and 6.

[0037] Table 5. Conversion rate of EVG to ethyl vanillin in mainstream flue gas

[0038]

[0039] Table 6. Conversion rate of EVG to ethyl vanillin in sidestream flue gas

[0040]

[0041] As can be seen from Tables 5 and 6, when the amount of EVG and ammonium polyphosphate added to each cigarette is 0.1 mg, the conversion rate of EVG to ethyl vanillin in the sidestream smoke is actually lower than that of EVG to ethyl vanillin in the mainstream smoke.

[0042] When the amount of EVG and ammonium polyphosphate added to each cigarette was 1.0 mg, the conversion rate of EVG to EVG in the main sidestream smoke was measured, as shown in Tables 7 and 8.

[0043] Table 7 Conversion rate of EVG to ethyl vanillin in mainstream flue gas

[0044]

[0045] Table 8. Conversion rate of EVG to ethyl vanillin in sidestream flue gas

[0046]

[0047] As can be seen from Tables 7 and 8, when the amount of EVG and ammonium polyphosphate added to each cigarette is 1.0 mg, the conversion of EVG to ethyl vanillin in the sidestream smoke is relatively low, which is not as high as the conversion rate of EVG to ethyl vanillin in the mainstream smoke.

[0048] Comparative Example 3: Effect of ammonium polyphosphate addition on the conversion rate of EVG to ethyl vanillin in sidestream flue gas.

[0049] The mixed solution of EVG and ammonium polyphosphate was uniformly added to cigarette tobacco and cigarette paper using a flavoring injection machine. The amount of EVG added to each cigarette was 0.4 mg, and the amount of ammonium polyphosphate added was 1.2 mg; that is, the mass ratio of ammonium polyphosphate to EVG was 3:1. Other procedures were the same as in Comparative Example 2. The conversion rate of EVG to ethyl vanillin in the main sidestream flue gas was measured and is shown in Tables 9 and 10.

[0050] Table 9. Conversion rate of EVG to ethyl vanillin in mainstream flue gas

[0051]

[0052] Table 10 Conversion rate of EVG to ethyl vanillin in sidestream flue gas

[0053]

[0054] As can be seen from Tables 9 and 10, the amount of EVG added to each cigarette is 0.4 mg, and the amount of ammonium polyphosphate added is 1.2 mg. That is, when the mass ratio of ammonium polyphosphate to EVG is 3:1, the conversion rate of EVG to ethyl vanillin in the sidestream smoke is low, and the conversion rate of EVG to ethyl vanillin in the mainstream smoke is also low.

[0055] When the amount of EVG added to each cigarette is 0.4 mg and the amount of ammonium polyphosphate added is 0.1 mg, that is, when the mass ratio of ammonium polyphosphate added to EVG is 1:4, the conversion rate of EVG to EVG in the main sidestream flue gas is measured, as shown in Tables 11 and 12.

[0056] Table 11 Conversion rate of EVG to ethyl vanillin in mainstream flue gas

[0057]

[0058] Table 12 Conversion rate of EVG to EVG in sidestream flue gas

[0059]

[0060] As can be seen from Tables 11 and 12, the amount of EVG added to each cigarette is 0.4 mg, and the amount of ammonium polyphosphate added is 0.1 mg. That is, when the mass ratio of ammonium polyphosphate to EVG is 1:4, the conversion rate of EVG to ethyl vanillin in the sidestream smoke is close to that without the addition of ammonium polyphosphate.

[0061] The above descriptions are merely some embodiments of the present invention. Those skilled in the art can make various modifications and improvements without departing from the inventive concept of the present invention, and these all fall within the scope of protection of the present invention.

Claims

1. A method of increasing the conversion of EVG to ethyl vanillin in sidestream smoke, characterized in that, EVG and a certain amount of intumescent flame retardant are mixed and added to the burning part of the cigarette; The intumescent flame retardant is ammonium polyphosphate; The amount of EVG added in the cigarette is 0.4 mg / cigarette; The amount of ammonium polyphosphate added is 1:1 in mass ratio with the added EVG.

2. The method of claim 1, wherein, The burning part is tobacco and / or cigarette paper.

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