METHOD FOR EXTRACTING TAR AROMA COMPONENTS FROM WITHIN CIGARETTE BUTTS AND APPLICATION THEREOF IN CIGARETTES

Abstract

The present disclosure provides a method for extracting tar aroma components from a cigarette butt and use of the tar aroma components in a cigarette. The method includes the following steps: (1) adding the cigarette butt to an extraction solvent, and carrying out ultrasound-assisted extraction to obtain an extraction solution; (2) centrifuging the extraction solution, and carrying out vacuum distillation on the supernatant to obtain a concentrated extractum; and (3) carrying out molecular distillation on the concentrated extractum, and collecting a light fraction of the molecular distillation to obtain the tar aroma components. In the present disclosure, the cigarette butt is used as a raw material, through the ultrasound-assisted extraction and separation by the molecular distillation to extract the tar, harmful substances in the tar are removed, and the aroma components are retained. The tar aroma components are applied to a heat-not-burn cigarette, so that the aroma, smoke and taste characteristics of the heat-not-burn cigarette are improved, and the problems of insipidness and uneven aroma release of the heat-not-burn cigarette are solved effectively.

Claims

1. A method for extracting tar aroma components from a cigarette butt, comprising the following steps: (1) adding the cigarette butt to an extraction solvent, and carrying out ultrasound-assisted extraction to obtain an extraction solution, the extraction solvent is at least one of methanol, anhydrous ethanol, petroleum ether and dichloromethane, the ultrasound-assisted extraction is carried out with an ultrasound power of 60-120 W for 5-30 min; (2) centrifuging the extraction solution, and carrying out vacuum distillation on the supernatant to obtain a concentrated extractum; and (3) carrying out two-stage molecular distillation on the concentrated extractum, and mixing light fractions of the first-stage molecular distillation and a second-stage molecular distillation to obtain the tar aroma components, wherein the first-stage molecular distillation is carried out at a heating temperature of 50-80° C. under a pressure of 100-200 Pa at a feed rate of 300-600 mL/h and a film wiping speed of 200-300 rpm; wherein the second-stage molecular distillation is carried out at a heating temperature of 90-110° C. under a pressure of 40-60 Pa at a feed rate of 300-600 mL/h and a film wiping speed of 200-300 rpm.

2. The method according to claim 1, wherein in the step (1), a ratio of the cigarette butt to the extraction solvent is 1 g:5-20 ml.

3. The method according to claim 1, wherein in the step (2), the centrifuging is carried out at 500-2000 r/min for 1-3 min; and the vacuum distillation is carried out at a temperature of 25-45° C. under a vacuum degree of 0.06-0.08 Mpa.

4. (canceled)

5. The method according to claim 1, further comprising a step of pretreating the cigarette butt.

6. Tar aroma components prepared by the method according to claim 1.

7. A flavor, containing the tar aroma components according to claim 6.

8. Use of the tar aroma components according to claim 6 in preparation of a cigarette.

9. The use according to claim 8, wherein the cigarette is a heat-not-burn cigarette.

10. The use according to claim 8, wherein the tar aroma components are added to a filter and a reconstituted tobacco blend of the cigarette.

11. (canceled)

12. (canceled)

13. (canceled)

14. (canceled)

15. The method according to claim 5, wherein the pretreating specifically comprises: tearing off outer wrapping paper from the cigarette butt, and cutting a tow into small segments with a length of less than 1 cm.

16. Use of the flavor according to claim 7 in preparation of a heat-not-burn cigarette.

17. The use according to claim 10, wherein the amount of the tar aroma components added is 2-5% of the weight of the reconstituted tobacco blend of the cigarette.

18. Tar aroma components prepared by the method according to claim 2.

19. Tar aroma components prepared by the method according to claim 3.

20. Tar aroma components prepared by the method according to claim 4.

21. Tar aroma components prepared by the method according to claim 5.

Description

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0031] The present disclosure will be described in detail in conjunction with specific examples. The following examples are only explanations for those skilled in the art to understand the technical solution of the present disclosure and to realize or use the present disclosure, and are not intended to limit the protection range of the present disclosure.

[0032] Unless otherwise specified, the raw materials and equipment used in the present disclosure are those available from the market or commonly used in the art.

[0033] The methods in the examples, unless otherwise specified, are conventional methods in the art.

Example 1 Extraction of Tar Aroma Components from Cigarette Butt

[0034] A method for extracting tar aroma components from a cigarette butt included the following steps:

[0035] (1) pretreating of the cigarette butt: outer wrapping paper of the cigarette butt was torn off, and a tow was cut into small segments with a length of less than 1 cm;

[0036] (2) 100 g of the pretreated cigarette butt was added to 1 L of petroleum ether, and ultrasound-assisted extraction was carried out with an ultrasound power of 100 W for 20 min to obtain an extraction solution;

[0037] (3) the extraction solution was centrifuged at 1000 r/min for 2 min, and vacuum distillation was carried out on the supernatant at 30° C. under 0.07 Mpa to obtain a concentrated extractum; and

[0038] (4) two-stage molecular distillation was carried out on the concentrated extractum, wherein first-stage molecular distillation was carried out at a heating temperature of 60° C. under a pressure of 150 Pa at a feed rate of 400 mL/h and a film wiping speed of 250 rpm; and second-stage molecular distillation was carried out at a heating temperature of 100° C. under a pressure of 50 Pa at a feed rate of 400 mL/h and a film wiping speed of 250 rpm; and light fractions of the first-stage molecular distillation and the second-stage molecular distillation were mixed.

[0039] The light fraction was detected by GC/MS. Components in the light fraction were furfural, furfuryl alcohol, ethylene glycol diacetate, 1-(1,3-dioxolan-2-yl)acetone, 4-cyclopentene-1,3-dione, methylcyclopentenolone, nicotine, 2-acetylfuran, 2(5H)-furanone, 5-methylfurfural, 3-methyl-2-cyclopenten-1-one, methylcyclopentenolone, benzyl alcohol, 2,3-dimethyl-2-cyclopentenone, ethylcyclopentenolone, 5-hydroxymethylfurfural, vanillin, megastigmatrienone A, 2,4,4-trimethylpentane-1,3-diyl bis(2-methylpropionate), farnesol, phthalic acid 1-butyl 2-isobutyl ester, scopoletin and tributyl prop-1-ene-1,2,3-tricarboxylate.

[0040] GC/MS conditions:

[0041] HP 6890/5973 GC-MS

[0042] (1) GC Conditions:

[0043] Chromatographic column: ULTRA2 (50 m×0.2 mm i.d×0.33 μm d.f.)

[0044] Detector: MS

[0045] Carrier gas, flow rate: He, 0.6 ml/min

[0046] Temperature of injection port: 290° C.

[0047] Temperature program: 80° C. (1 min) 2° C./min.fwdarw.280° C. (10 min)

[0048] Split ratio, injection volume: 1:10, 2 μl

[0049] (2) GC/MS Conditions:

[0050] GC conditions: the same as above

[0051] Temperature of transfer line: 230° C.

[0052] Temperature of ion source: 230° C.

[0053] Ionization energy: 70 eV

[0054] Mass range: 30-350 u

[0055] Carrier gas: He

[0056] MS spectra: NIST Library

Example 2 Use of Tar Aroma Components in Cigarette

[0057] The light fraction prepared in Example 1 was added to a condensation auxiliary material in an amount of 3% (by mass) of an HnB reconstituted tobacco blend to prepare an HnB sample A with tar aroma components.

[0058] The light fraction prepared in Example 1 was added to a reconstituted tobacco blend in an amount of 2% (by mass) of the HnB reconstituted tobacco blend to prepare an HnB sample B with tar aroma components.

[0059] The light fraction prepared in Example 1 was added to a filter auxiliary material in an amount of 5% (by mass) of the HnB reconstituted tobacco blend to prepare an HnB sample C with tar aroma components.

[0060] After the cigarette samples prepared by the above solution and a cigarette without the tar aroma components were equilibrated in a constant-temperature and constant-humidity environment of (20±1°) C. and (60±3)% RH for 24 h, 10 or more smoking evaluators were organized to perform sensory evaluation on the cigarette samples with reference to Tobacco in processing-Sensory evaluation methods (YC/T 415-2011). The evaluation results are shown in Table 1.

TABLE-US-00001 TABLE 1 Sensory evaluation results HnB HnB HnB Control sample sample sample Evaluation sample sample A B C Aroma Quality of 5.0 5.5  5.25  5.25 characteristics aroma Quantity of 5.0 5.5 5.5 5.5 aroma Stability 4.0  4.25  4.25  4.25 Offensive 5.0  5.25  5.25 5.5 odor Plumpness of 4.0 5.5 5.0 5.5 aroma Smoke Concentration 5.0 5.5 5.5 6.0 characteristics Strength 5.0 5.5 5.5 6.0 Harshness 5.0 5.5 5.5 5.5 Agglomeration 5.0 5.5 5.5 5.5 Stability 4.0  4.25  4.25  4.25 Taste Irritancy 5.0 5.5 5.5  5.25 characteristics Dry feeling 5.0 5.5 5.5 5.5 Clean degree 5.0 5.5 5.5 5.5 Sweet 4.0 5.0 5.0 5.5 aftertaste

[0061] As shown in Table 1, compared with the control group, after the tar aroma components prepared in the example of the present disclosure was added, the smoke characteristics, the aroma characteristics and the taste characteristics of heat-not-burn cigarettes were improved to different degrees. The quantity of aroma and the plumpness of aroma of the cigarettes were improved significantly, and the other aroma characteristics were also improved. The concentration and strength of the smoke were increased, and the harshness and agglomeration were also improved. The irritancy was reduced, the dry feeling was decreased, and the sweet aftertaste was increased significantly. After the tar aroma components prepared in the example of the present disclosure was added, the problems of insipidness and insufficient plumpness of aroma of the heat-not-burn cigarettes were solved effectively.

Example 3 Selection of Conditions for Preparation Method

[0062] 1. Selection of Extraction Solvent

[0063] Methanol, dichloromethane, anhydrous ethanol, glycerin, petroleum ether and polyethylene glycol 400 were respectively used to carry out ultrasound-assisted extraction on the pretreated discarded cigarette butt, wherein a ratio of material to liquid was 1:10 (g/mL), and the ultrasound-assisted extraction was carried out once with a ultrasound-assisted extraction power of 100 W for 20 min. The effects of different solvents on extraction effects (the amount of component extracted from per g of cigarette butt) were compared and analyzed. The detection results are shown in Table 2. As can be seen from Table 2, the anhydrous ethanol had the best extraction effects.

TABLE-US-00002 TABLE 2 Extraction effects of different organic solvents (mg/g) Extraction solvent Holding Dichlorom Anhydrous Petroleum Polyethylene No. time/min Component Methanol ethane ethanol Glycerin ether glycol 400 1 11.087 Furfural 0.95 0.87 1.06 0.32 0.87 0.27 2 11.963 Furfuryl alcohol 1.02 0.99 1.13 0.28 0.88 0.25 3 12.428 Ethylene glycol 0.48 0.43 0.52 0.14 0.39 0.11 diacetate 4 13.016 1-(1,3-dioxolan-2-yl) 0.45 0.43 0.51 0.15 0.43 0.12 acetone 5 13.258 4-cyclopentene-1,3- 0.43 0.42 0.51 0.16 0.44 0.14 dione 6 14.240 Methylcyclopentenolone 0.37 0.41 0.44 0.12 0.36 0.11 7 14.406 Nicotine 2.15 2.16 2.44 0.66 2.06 0.52 8 14.446 2-acetylfuran 0.27 0.25 0.28 0.08 0.31 / 9 14.646 2(5H)-furanone 0.41 0.42 0.42 0.11 0.43 0.24 10 16.934 5 -methylfurfural 1.30 1.47 1.56 0.43 1.44 0.36 11 17.051 3 -methyl-2-cyclopenten- 0.82 0.81 0.87 0.26 0.80 0.18 1-one 12 20.257 Methyleyelopentenolone 1.73 1.38 1.67 0.47 1.52 0.31 13 20.545 Benzyl alcohol 0.43 0.41 0.48 0.14 0.43 0.13 14 20.745 2,3-dimethyl-2-cyclopentenone 1.10 1.10 1.27 0.39 1.13 0.32 15 24.792 Ethylcyclopentenolono 0.51 0.46 0.53 0.18 0.44 0.14 16 30.262 5-hydroxymethylfurfural 1.24 1.15 1.33 0.45 1.13 0.32 17 37.938 Vanillin 0.67 0.61 0.68 0.24 0.64 0.14 18 45.367 Megastigmatrienone A 1.02 0.84 0.99 0.34 0.91 0.22 19 45.820 2,4,4-trimethylpentane- 0.52 0.52 0.58 0.21 0.51 0.15 1,3-diyl bis(2-methylpropionate) 20 56.972 Farnesol 0.44 0.41 0.46 0.16 0.39 0.11 21 58.684 Phthalic acid 1-butyl 0.70 0.68 0.76 0.26 0.65 0.16 2-isobutyl ester 22 59.096 Scopoletin 0.63 0.59 0.61 0.24 0.59 0.13 23 64.684 Tributyl prop- 0.57 0.54 0.60 0.16 0.53 0.11 1-ene-1,2,3-tricarboxylate Total amount 18.19 17.35 19.70 5.95 17.28 4.54

[0064] 2. Selection of Ultrasound-Assisted Extraction Time

[0065] 100 g of the pretreated discarded cigarette butt was added to 1 L of anhydrous ethanol, ultrasound-assisted extraction was carried out with an ultrasound power of 100 W for 2 min, 5 min, 10 min, 20 min, 30 min and 40 min, respectively, and the extraction effects were tested. The test results are shown in Table 3. As can be seen from Table 3, the ultrasound-assisted extraction for 10 min had the best extraction effects.

TABLE-US-00003 TABLE 3 Extraction effects of different ultrasound-assisted extraction times (mg/g) Holding Extraction solvent No. time Component 2 min 5 min 10 min 20 min 30 min 40 min 1 11.087 Furfural 0.32 0.74 1.06 1.03 1.05 0.62 2 11.963 Furfuryl alcohol 0.39 0.84 1.13 1.09 0.97 0.58 3 12.428 Ethylene glycol 0.21 0.41 0.52 0.49 0.51 0.34 diacetate 4 13.016 1-(1,3-dioxolan-2-yl) 0.17 0.34 0.51 0.48 0.49 0.32 acetone 5 13.258 4-cyclopentene-1,3- 0.18 0.37 0.51 0.49 0.43 0.38 dione 6 14.240 Methylcyclopentenolone 0.17 0.34 0.44 0.43 0.38 0.27 7 14.406 Nicotine 0.79 1.72 2.44 2.17 1.92 0.78 8 14.446 2-acetylfuran 0.13 0.23 0.28 0.28 0.42 0.16 9 14.646 2(5H)-furanone 0.16 0.34 0.42 0.43 0.43 0.24 10 16.934 5-methylfurfural 0.58 1.24 1.56 1.52 1.52 0.64 11 17.051 3-methyl-2-cyclopenten- 0.38 0.76 0.87 0.86 0.83 0.57 1-one 12 20.257 Methylcyclopentenolone 0.61 1.30 1.67 1.73 1.56 0.72 13 20.545 Benzyl alcohol 0.18 0.39 0.48 0.49 0.43 0.28 14 20.745 2,3-dimethyl-2- 0.45 0.94 1.27 1.11 0.98 0.57 cyclopentenone 15 24.792 Ethylcyclopentenolone 0.23 0.42 0.53 0.50 0.45 0.31 16 30.262 5-hydroxymethylfurfural 0.48 1.01 1.33 1.24 1.10 0.67 17 37.938 Vanillin 0.27 0.49 0.68 0.71 0.64 0.38 18 45.367 Megastigmatrienone A 0.38 0.77 0.99 1.02 0.90 0.45 19 45.820 2,4,4-trimethylpentane- 0.22 0.44 0.58 0.55 0.49 0.36 1,3-diyl bis(2-methylpropionate) 20 56.972 Farnesol 0.16 0.35 0.46 0.43 0.38 0.28 21 58.684 Phthalic acid 1-butyl 0.29 0.54 0.76 0.71 0.63 0.36 2-isobutyl ester 22 59.096 Scopoletin 0.26 0.48 0.61 0.62 0.63 0.34 23 64.684 Tributyl 0.24 0.47 0.60 0.57 0.60 0.35 prop-1-ene-1,2,3- tricarboxylate Total amount 7.25 14.93 19.70 18.93 17.76 9.97

Example 4

[0066] A method for extracting tar aroma components from a cigarette butt included the following steps:

[0067] (1) pretreating of the cigarette butt: outer wrapping paper of the cigarette butt was torn off, and a tow was cut into small segments with a length of less than 1 cm;

[0068] (2) 100 g of the pretreated cigarette butt was added to 500 mL of anhydrous ethanol and ultrasound-assisted extraction was carried out with an ultrasound power of 60 W for 10 min to obtain an extraction solution;

[0069] (3) the extraction solution was centrifuged at 500 r/min for 3 min, and vacuum distillation was carried out on the supernatant at 25° C. under 0.08 Mpa to obtain a concentrated extractum; and

[0070] (4) two-stage molecular distillation was carried out on the concentrated extractum, wherein first-stage molecular distillation was carried out at a heating temperature of 50° C. under a pressure of 200 Pa at a feed rate of 600 mL/h and a film wiping speed of 300 rpm; and second-stage molecular distillation was carried out at a heating temperature of 90° C. under a pressure of 60 Pa at a feed rate of 600 mL/h and a film wiping speed of 300 rpm; and light fractions of the first-stage molecular distillation and the second-stage molecular distillation were mixed.

Example 5

[0071] A method for extracting tar aroma components from a cigarette butt included the following steps:

[0072] (1) pretreating of the cigarette butt: outer wrapping paper of the cigarette butt was torn off, and a tow was cut into small segments with a length of less than 1 cm.

[0073] (2) 100 g of the pretreated cigarette butt was added to 2 L of anhydrous ethanol and ultrasound-assisted extraction was carried out with an ultrasound power of 120 W for 10 min to obtain an extraction solution.

[0074] (3) the extraction solution was centrifuged at 2000 r/min for 1 min, and vacuum distillation was carried out on the supernatant at 45° C. under 0.06 Mpa to obtain a concentrated extractum.

[0075] (4) two-stage molecular distillation was carried out on the concentrated extractum, wherein first-stage molecular distillation was carried out at a heating temperature of 80° C. under a pressure of 100 Pa at a feed rate of 300 mL/h and a film wiping speed of 200 rpm; and second-stage molecular distillation was carried out at a heating temperature of 110° C. under a pressure of 40 Pa at a feed rate of 300 mL/h and a film wiping speed of 200 rpm; and light fractions of the first-stage molecular distillation and the second-stage molecular distillation were mixed.

Example 6

[0076] This example was different from Example 5 in that: in the step (4), one-stage molecular distillation was carried out on the concentrated extractum, wherein the molecular distillation was carried out at a heating temperature of 80° C. under a pressure of 100 Pa at a feed rate of 300 mL/h and a film wiping speed of 200 rpm, thereby obtaining a light fraction. The rest were the same as the steps in the method in Example 5.

[0077] The light fraction prepared in this example was added to a reconstituted tobacco blend in an amount of 3% (by mass) of the HnB reconstituted tobacco blend to prepare an HnB sample 6 #.

Example 7

[0078] This example was different from Example 5 in that: in the step (4), one-stage molecular distillation was carried out on the concentrated extractum, wherein the molecular distillation was carried out at a heating temperature of 110° C. under a pressure of 40 Pa at a feed rate of 300 mL/h and a film wiping speed of 200 rpm, thereby obtaining a light fraction. The rest were the same as the steps in the method in Example 5.

[0079] The light fractions prepared in Examples 4-7 were tested for their types and contents thereof. The test results showed that the types and contents of the light fractions prepared in Examples 4-5 were greater than those of the light fractions prepared in Examples 6-7.

[0080] The light fractions prepared in Examples 4-7 were respectively added to a reconstituted tobacco blend in an amount of 3% (by mass) of the HnB reconstituted tobacco blend to prepare an HnB sample 4 #, an HnB sample 5 #, an HnB sample 6 #and an HnB sample 7 #. After the cigarette samples were equilibrated in a constant-temperature and constant-humidity environment of (20±1°) C. and (60±3)% RH for 24 h, 20 or more smoking evaluators were organized to perform sensory evaluation on the cigarette samples with reference to Tobacco in processing-Sensory evaluation methods (YC/T 415-2011). The evaluation results are shown in Table 4.

TABLE-US-00004 TABLE 4 Sensory evaluation results HnB HnB HnB HnB sample sample sample sample Evaluation sample 4# 5# 6# 7# Aroma Quality of 5.50 5.75 5.25 5.25 characteristics aroma Quantity of 5.25 5.50 5.00 5.25 aroma Stability 4.25 4.50 4.25 4.25 Offensive 5.25 5.25 5.00 5.00 odor Plumpness of 5.25 5.50 5.00 5.25 aroma Smoke Concentration 5.50 5.50 5.25 5.25 characteristics Strength 5.50 5.75 5.25 5.50 Harshness 5.25 5.25 5.00 5.00 Agglomeration 5.50 5.50 5.25 5.25 Stability 4.50 4.50 4.25 4.25 Taste Irritancy 5.50 5.75 5.25 5.50 characteristics Dry feeling 5.50 5.75 5.25 5.25 Clean degree 5.50 5.50 5.25 5.25 Sweet 5.00 5.00 5.00 5.00 aftertaste

[0081] As can be seen from the results in Table 4, after the light fractions prepared in the examples of the present disclosure were added to the cigarette, the aroma characteristics, the smoke characteristics and the taste characteristics of the cigarette were improved to different degrees, and the problems of insipidness and insufficient plumpness of aroma of the heat-not-burn cigarettes were solved effectively.

[0082] The above are only examples of the present application, and the protection scope of the present application is not limited by these specific examples, but is determined by the claims of the present application. For those skilled in the art, various modifications and variations can be made to the present application. Any modification, equivalent replacement or improvement made within the technical ideas and principle of the present application shall fall within the protection scope of the present application.