A multi-component composite refined product of clove by dry distillation, its preparation method and application

Abstract

This invention discloses a multi-component refined compound of clove obtained by dry distillation, its preparation method, and its application. The preparation method involves: placing clove powder in a high-temperature dry distillation reactor for localized puffing reaction to obtain eugenol; mixing the puffed clove powder with a composite solvent and then repeatedly heating and extracting the mixture to obtain a precursor of the refined compound; centrifuging the precursor and collecting the supernatant to obtain the final product. This method, through localized puffing reaction, significantly increases the bulkiness of the clove powder, effectively enhancing the release of aroma compounds such as eugenol, acetyleugenol, and caryophyllene from the clove; using this refined compound as a flavoring agent in heated non-combustible cigarettes effectively improves the richness and fullness of the smoke.

Description

Technical Field

[0001] This invention relates to a multi-component compound refined from cloves, specifically to a dry distillation multi-component compound refined from cloves, its preparation method, and its application, belonging to the field of fragrance and flavor technology. Background Technology

[0002] Heated cigarettes primarily work by heating tobacco leaves at a low temperature. The tobacco leaf is precisely heated using temperature control technology to achieve the ideal temperature for releasing the aromatic compounds and nicotine, thus producing smoke. This method heats the tobacco leaves to a level sufficient to release their flavor without igniting them. Its taste is closest to traditional cigarettes and is expected to be the first to be accepted by smokers. Comparative analysis of heated cigarettes and traditional cigarettes reveals that the fundamental sensory difference lies in their different heating temperatures. Traditional cigarettes involve combustion, with aroma compounds arising from the transfer of these compounds within the tobacco itself and the complex thermal decomposition reactions during combustion. Whether through the transfer of aroma compounds or thermal decomposition, the aroma compounds primarily originate from the pyrolysis / distillation zone of the cigarette during combustion, at temperatures ranging from approximately 250 to 600°C. Heated cigarettes, on the other hand, involve heating, not combustion, with heating temperatures generally not exceeding 300°C. The internal temperature of the cigarette is even lower. Therefore, compared to traditional cigarettes, heated cigarettes, due to their lower temperature, do not reach the aroma-producing temperature of traditional cigarettes, resulting in significantly less aroma richness. Consequently, external extracts are needed to enhance the smoke quality.

[0003] In addition to tobacco flavor, heated cigarette products have added a series of characteristic flavors such as cocoa, coffee, mint, fruit, and clove in terms of smoke characteristics. Clove flavor, in particular, is very popular among consumers in Indonesia.

[0004] Currently, common extraction methods for clove extract include solvent extraction and distillation. CN110025010A describes mixing clove powder with an ethanol solution, followed by ultrasonic treatment, flash extraction, and filtration. The mixture is then concentrated until all ethanol is removed and freeze-dried to obtain the clove extract. CN 107802676B describes refluxing the clove extract three times with 10 times its volume of 75% ethanol, each extraction lasting one hour. The extracts are collected and combined, the ethanol is recovered until no alcohol odor remains, and the extract is filtered, concentrated, and then vacuum-dried to obtain the clove extract.

[0005] In summary, the clove extract obtained by traditional methods has a slightly weak spicy characteristic and lacks the characteristic aroma of clove, which cannot meet the requirements of flavoring for heated cigarettes. Therefore, the market urgently needs a flavoring for heated cigarettes that is rich in aroma and has a distinct fragrance. Summary of the Invention

[0006] In view of the problems existing in the prior art, the first objective of the present invention is to provide a dry distillation clove multi-component composite refined product. Based on the synergistic effect between the components, the refined product not only ensures that it has obvious clove aroma characteristics, but also significantly increases the content and variety of aroma substances. Compared with clove powder and existing clove flavorings, its richness and fullness are significantly improved.

[0007] The second objective of this invention is to provide a method for preparing a multi-component composite refined product of dry distilled cloves. This method first involves a localized expansion reaction, where the clove powder is heated at 100–200°C for a period of time to induce localized expansion of the internal structure of the clove powder, significantly increasing its fluffiness and thereby enhancing the release of aroma-producing substances such as eugenol, acetyleugenol, and caryophyllene from the clove. Then, the dry distilled clove powder is extracted multiple times using a composite solvent and followed by centrifugation to obtain a clove refined product with rich aroma and distinct fragrance.

[0008] The third objective of this invention is to provide an application of a dry-distilled clove multi-component compound refinement as a flavoring agent for heated tobacco products. Based on the excellent technical effects of this compound refinement, its application as a flavoring agent in heated tobacco products can effectively improve the sensory quality of heated tobacco products. GC-MS testing shows that the total amount of aroma compounds in this refinement is greater than 15, with approximately 10 being the main aroma compounds. Sensory analysis indicates that heated tobacco products using this invention produce a slightly cool and bitter smoke with a rich and complex aroma, exhibiting a distinct clove flavor characteristic.

[0009] To achieve the above-mentioned technical objectives, the present invention provides a method for preparing a multi-component composite refined product of clove by dry distillation, comprising: placing clove powder in a high-temperature dry distillation reactor for local expansion reaction to obtain dry distilled eugenol; mixing the dry distilled clove powder with a composite solvent evenly and then performing multiple heating extractions, combining the extracts to obtain a precursor of the refined product; centrifuging the precursor of the refined product and collecting the supernatant to obtain the final product.

[0010] As a preferred embodiment, the conditions for the localized expansion reaction are: in a closed environment, the reaction is carried out at 100–200°C for 0.5–1 hour.

[0011] As a preferred embodiment, the composite solvent is at least two of ethanol, propanol, deionized water, ethyl acetate, and butyl acetate.

[0012] As a preferred embodiment, when the composite solvent is a binary mixed solvent, its mass ratio is 8-60:40-92.

[0013] As a preferred embodiment, when the binary mixed solvent is an alcohol and an ester, the mass ratio of alcohol to ester is 40-60:40-60.

[0014] As a preferred embodiment, when the binary mixed solvent is an alcohol and water, the mass ratio of alcohol to water is 8-12:88-92.

[0015] As a preferred embodiment, when the composite solvent is a ternary mixed solution, its mass ratio is 20-30:1-8:60-70. More preferably, the ternary mixed solution is composed of an alcohol, water, and an ester.

[0016] Since there are many types of aroma compounds in dry-distilled clove powder, the composite solvent of this invention must be used in accordance with the above requirements to ensure that alkenes, phenols, esters and aldehydes are completely extracted.

[0017] As a preferred embodiment, the mass ratio of the dry distilled clove powder to the composite solvent is 1:6 to 10.

[0018] As a preferred embodiment, the heating extraction is performed 2 to 5 times.

[0019] As a preferred embodiment, the heating extraction process is as follows: the mixture of dry distilled clove powder and compound solvent is heated from room temperature to 60-80°C, and refluxed for 0.5-1 hour under stirring, and repeated 2-5 times.

[0020] As a preferred embodiment, the centrifugal separation conditions are: centrifugation at 3000-4000 rpm for 5-10 minutes at room temperature.

[0021] The present invention also provides a dry distillation clove multi-component composite refined product, obtained by any of the preparation methods described above.

[0022] As a preferred embodiment, the main components of the multi-component composite refined product, in descending order of mass percentage, are eugenol, benzyl acetate, methyl n-pentyl ketone, and methyl salicylate.

[0023] This invention also provides an application of a dry-distilled clove multi-component compound refined product as a flavoring agent for heated non-combustible cigarettes.

[0024] Compared with the prior art, the beneficial technical effects of the technical solution of the present invention are as follows:

[0025] 1) The clove multi-component compound refined product provided by the present invention, based on the synergistic effect between the components, not only ensures that it has obvious clove aroma characteristics, but also greatly increases the content and variety of aroma substances. Compared with clove powder and existing clove flavorings, its richness and thickness are significantly improved.

[0026] 2) The preparation method provided by the present invention firstly involves a local expansion reaction, heating at 100-200°C for a period of time to induce local expansion of the internal structure of clove powder, which significantly increases the fluffiness of clove powder and thus improves the release of aroma substances such as eugenol, acetyleugenol and caryophyllene in clove. Then, the clove powder is extracted and dry-distilled multiple times with a composite solvent, and then separated by centrifugation to obtain a clove refined product with rich aroma and obvious fragrance.

[0027] 3) Based on the excellent technical effects of the above-mentioned multi-component compound refined product, the technical solution provided by the present invention can be used as a flavoring agent in heated cigarettes, which can effectively improve the sensory quality of heated cigarettes. According to GC-MS testing, the total amount of aroma substances in the refined product is greater than 15 kinds, and the main aroma substances are about 10 kinds. According to sensory test analysis, the smoke of heated cigarettes using the refined product of the present invention is slightly cool and bitter, with a rich and rich aroma and high richness, and has obvious clove flavor characteristics. Attached Figure Description

[0028] Figure 1 This is a GC-MS image of the aroma components in the clove extract obtained in Example 3 of the present invention;

[0029] Figure 1 In the given list, 1 is β-caryophyllene; 2 is lanthene; 3 is piperonol; 4 is eugenol; 5 is acetyleugenol; 6 is methyl salicylate; 7 is methyl n-pentyl ketone; 8 is benzyl acetate; 9 is benzaldehyde; and 10 is m-methoxybenzaldehyde. Detailed Implementation

[0030] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making inventive steps are within the scope of protection of the present invention.

[0031] Example 1

[0032] This embodiment provides a multi-component composite refined product of clove obtained by dry distillation, the preparation method of which is as follows:

[0033] 100g of clove powder was placed in a high-temperature dry distillation reactor, heated at 100℃ in a sealed container for 1 hour to carry out a localized puffing reaction. After cooling to room temperature, 80g of dry distilled clove powder was obtained. The dry distilled clove powder was extracted by reflux at 60℃ for 0.5 hours with a mixed solvent of ethanol:water:ethyl acetate = 25:5:70, wherein the ratio of dry distilled clove powder to the mixed solvent was 1:6. The resulting extract was placed in a centrifuge bottle and subjected to solid-liquid separation at room temperature. After centrifugation, the supernatant was collected to obtain the refined clove product.

[0034] Clove extract was added to heated cigarettes at a dosage of 0.2%. Based on GB 5604.4—2005 "Cigarettes Part 4: Sensory Technical Requirements", a tasting evaluation was conducted, and the evaluation results are shown in Table 1.

[0035] Example 2

[0036] 100g of clove powder was placed in a high-temperature dry distillation reactor, and heated at 150℃ in a sealed environment for 40 minutes to carry out a localized puffing reaction. After cooling to room temperature, 70g of dry distilled clove powder was obtained. The dry distilled clove powder was then extracted by reflux at 75℃ for 1 hour using a mixed solvent of ethanol:ethyl acetate = 40:60, with a clove powder to mixed solvent ratio of 1:8. The resulting extract was placed in a centrifuge bottle for solid-liquid separation at room temperature. After centrifugation, the supernatant was collected to obtain the refined clove product.

[0037] Clove extract was added to heated cigarettes at a dosage of 0.2%. Based on GB 5604.4—2005 "Cigarettes Part 4: Sensory Technical Requirements", a tasting evaluation was conducted, and the evaluation results are shown in Table 1.

[0038] Example 3

[0039] 100g of clove powder was placed in a high-temperature dry distillation reactor, and heated at 200℃ in a sealed environment for 30 minutes to carry out a localized puffing reaction. After cooling to room temperature, 60g of dry distilled clove powder was obtained. The dry distilled clove powder was extracted by reflux at 80℃ for 0.5h with a mixed solvent of ethanol:water = 90:10, wherein the ratio of dry distilled clove powder to mixed solvent was 1:10. The obtained extract was placed in a centrifuge bottle and subjected to solid-liquid separation at room temperature. After centrifugation, the supernatant was collected to obtain the refined clove product.

[0040] Clove extract was added to heated cigarettes at a dosage of 0.2%. Based on GB 5604.4—2005 "Cigarettes Part 4: Sensory Technical Requirements", a tasting evaluation was conducted, and the evaluation results are shown in Table 1.

[0041] Comparative Example 1

[0042] This comparative example is exactly the same as Example 3, except that the clove powder does not undergo a localized puffing reaction.

[0043] Clove extract was added to heated cigarettes at a dosage of 0.2%. Based on GB 5604.4—2005 "Cigarettes Part 4: Sensory Technical Requirements", a tasting evaluation was conducted, and the evaluation results are shown in Table 1.

[0044] To better reflect the superior technical effects of the above-mentioned refined product, a blank control was also conducted, and the evaluation results are shown in Table 1.

[0045] Table 1

[0046]

[0047] As shown in Table 1, the refined products provided by this invention all exhibit distinct clove flavor characteristics. Furthermore, with increasing local puffing temperature, the aroma of the refined products becomes increasingly rich, the spiciness gradually becomes more pronounced, and the bitterness gradually decreases. In particular, compared to the refined product obtained in Comparative Example 1, Example 3 not only significantly improves the intensity of the aroma but also reduces unpleasant odors such as spiciness and bitterness. Further, this invention also conducted GC-MS testing on the refined product obtained in Example 3. The test results show that the refined product contains β-caryophyllene, lanthanide, piperine, eugenol, acetyleugenol, methyl salicylate, methyl n-pentyl ketone, benzyl acetate, benzaldehyde, and m-methoxybenzaldehyde. It is precisely based on these abundant aroma-producing substances that the technical effect of rich and pronounced aroma in heated cigarette smoke is achieved.

Claims

1. A method for preparing a multi-component composite refined product of clove by dry distillation, characterized in that, include: Clove powder was placed in a high-temperature dry distillation reactor for localized puffing reaction to obtain dry distilled eugenol; the dry distilled clove powder was mixed evenly with a composite solvent and then subjected to multiple heating extractions, and the extracts were combined to obtain a purified precursor; the purified precursor was centrifuged and the supernatant was collected to obtain the product.

2. The method for preparing a multi-component composite refined product of clove by dry distillation according to claim 1, characterized in that: The conditions for the localized expansion reaction are: in a closed environment, the reaction is carried out at 100-200°C for 0.5-1 hour.

3. The method for preparing a multi-component composite refined product of clove by dry distillation according to claim 1, characterized in that: The composite solvent is at least two of ethanol, propanol, deionized water, ethyl acetate, and butyl acetate.

4. The method for preparing a multi-component composite refined product of clove by dry distillation according to claim 3, characterized in that: When the composite solvent is a binary mixed solvent, its mass ratio is 8-12:88-92; when the composite solvent is a ternary mixed solution, its mass ratio is 20-30:1-8:60-70.

5. The method for preparing a multi-component composite refined product of clove by dry distillation according to claim 1, characterized in that: The mass ratio of the dry distilled clove powder to the compound solvent is 1:6 to 10; the number of heating extractions is 2 to 5.

6. The method for preparing a multi-component composite refined product of clove by dry distillation according to claim 1, characterized in that: The heating extraction process is as follows: the mixture of dry distilled clove powder and compound solvent is heated from room temperature to 60-80°C, and then refluxed for 0.5-1 hour under stirring, and repeated 2-5 times.

7. The method for preparing a multi-component composite refined product of clove by dry distillation according to claim 1, characterized in that: The centrifugation conditions are as follows: centrifugation at 3000-4000 rpm for 5-10 minutes at room temperature.

8. A multi-component refined compound of clove obtained by dry distillation, characterized in that: Obtained by the preparation method according to any one of claims 1 to 7.

9. The clove multi-component composite refined product by dry distillation according to claim 8, characterized in that: The main components of the multi-component composite refined product, in descending order of mass percentage, are eugenol, benzyl acetate, methyl n-pentyl ketone, and methyl salicylate.

10. An application of a multi-component refined compound of cloves obtained by dry distillation, characterized in that: As a flavoring agent for heated tobacco products.

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