CN111035054B - Method for preparing tar extract with aroma characteristics from waste cigarette butts and application of tar extract in cigarettes - Google Patents

Method for preparing tar extract with aroma characteristics from waste cigarette butts and application of tar extract in cigarettes Download PDF

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CN111035054B
CN111035054B CN201911179300.XA CN201911179300A CN111035054B CN 111035054 B CN111035054 B CN 111035054B CN 201911179300 A CN201911179300 A CN 201911179300A CN 111035054 B CN111035054 B CN 111035054B
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cigarette
tar extract
tar
cigarette butts
waste
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CN111035054A (en
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李力群
柴颖
郭春生
张峻松
陈晨
纪旭东
叶亚军
王旭东
乔月梅
李瑞丽
梁淼
张文洁
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Inner Mongolia Kunming Cigarettes Co ltd
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    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/24Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B3/00Preparing tobacco in the factory
    • A24B3/12Steaming, curing, or flavouring tobacco
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B3/00Preparing tobacco in the factory
    • A24B3/14Forming reconstituted tobacco products, e.g. wrapper materials, sheets, imitation leaves, rods, cakes; Forms of such products

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

The invention provides a method for preparing tar extract with aroma characteristics from waste cigarette butts, which comprises the following steps: (1) adding the waste cigarette butts into an organic solvent for ultrahigh pressure extraction to obtain an extracting solution; (2) centrifuging the extracting solution, and distilling and concentrating the supernatant under reduced pressure to obtain the tar extract. The method takes the waste cigarette butts as raw materials, utilizes organic solvent ultrahigh-pressure extraction and centrifugal separation, and reduced pressure distillation and concentration to remove the organic solvent, retains the components with aroma characteristics, is applied to the heating non-combustible cigarettes, improves the aroma, smoke and taste characteristics of the heating non-combustible cigarettes, and effectively solves the problem of low smoke taste of the heating non-combustible cigarettes. According to the invention, the tar extract with higher extraction rate is obtained from the waste cigarette butts by optimizing the condition of organic solvent ultrahigh-pressure extraction. The invention takes the waste cigarette butts as raw materials, which not only can avoid the pollution of the cigarette butts to the environment, but also can utilize the byproduct tar after the cigarette is burnt and smoked.

Description

Method for preparing tar extract with aroma characteristics from waste cigarette butts and application of tar extract in cigarettes
Technical Field
The invention relates to a method for preparing tar extract with aroma characteristics from waste cigarette butts and application of the tar extract in cigarettes, belonging to the technical field of tobacco technology.
Background
The cigarette butt refers to the residual part of the cigarette after burning and smoking, mainly consists of outer tipping paper and fiber tows wrapped by forming paper, and tar and other harmful particles in particulate matters of main stream smoke are mainly trapped in the cigarette butt. A large amount of cigarettes are consumed in China every year, and accordingly a large amount of waste cigarette butts are produced, so that the environment is greatly polluted. Meanwhile, the waste cigarette butts contain a large amount of tar substances, and the cigarette tar not only contains aroma components which have positive effects on sensory quality, such as alcohols, ketones, furans, pyrazines, esters and the like, but also contains nicotine which can improve the physiological satisfaction of consumers, and also contains harmful substances which have obvious negative effects on sensory effects, such as amines, aldehydes and the like. Therefore, the waste cigarette butts are used as raw materials, tar substances with aroma characteristics are extracted, the pollution of the waste cigarette butts to the environment can be avoided, the effective components of the waste cigarette butts can be recycled, and the method has important significance for circular economy and sustainable development.
In recent years, new tobacco products such as electronic cigarettes and non-burning cigarettes have been rapidly developed. A heated non-burning cigarette is a low temperature cigarette that heats tobacco leaves just enough to emit a flavor without igniting the tobacco leaves. In general, when ordinary cigarettes are smoked, a large number of harmful substances are generated at a high temperature of 350 ℃ to 600 ℃, and when low-temperature cigarettes are all at a temperature below 300 ℃, the harmful substances are reduced. Compared with the traditional cigarette, the cigarette which is not burnt after being heated has low heating temperature and less harmful substance release, but has the problems of light smoke taste, weak cigarette fragrance, unbalanced fragrance release and the like which are not easy to be accepted by smokers.
CN109959649A discloses a cigarette tar extract with chemiluminescence property, and the preparation method of the cigarette tar extract comprises the following steps: adding reagent into cigarette tar for extraction to obtain cigarette tar extract. The cigarette tar can be prepared by the following steps: smoking the cigarette, filtering the generated smoke, and collecting the smoke particle phase substances to obtain the cigarette tar. In the patent, the cigarette tar extract is prepared by ultrasonic extraction in an open system under natural light conditions, so that the contained luminescent substance has stable property and is insensitive to factors such as illumination, oxygen, temperature and the like; the extract has wide luminescence response range to medium pH value, and can generate chemiluminescence reaction under acidic, neutral or alkaline conditions. In the patent, the cigarette tar is the tar in the smoke particulate matter, and the prepared tar extract has a luminous property, and does not relate to the extraction of the tar in the waste cigarette butts to obtain the extract with a fragrance characteristic.
CN102559388A discloses a tobacco essential oil, a preparation method thereof and an application thereof in cigarettes, wherein the tobacco essential oil is prepared by the following steps: waste and inferior tobacco powder → organic solvent extraction → essential oil crude extract → water vapor introduction → condensation → oil-water separation → tobacco essential oil. The tobacco essential oil of the invention is added into the cut tobacco of the cigarette as a flavoring agent, which can increase the herbal fragrance of the cigarette, improve the quality of the fragrance of the cigarette, reduce the stimulation and the miscellaneous gas of the tobacco and soften the smoke. The patent takes waste and inferior tobacco powder generated in the cigarette production process as a raw material, the waste and inferior tobacco powder does not contain tar components, and the patent does not relate to a preparation method of tar extract.
Disclosure of Invention
The invention aims to provide a method for preparing tar extract with aroma characteristics from waste cigarette butts and application of the tar extract in cigarettes. The method takes the waste cigarette butts as raw materials, adopts the ultrahigh pressure extraction and reduced pressure distillation methods to obtain the tar extract with the aroma characteristics, and applies the tar extract containing the aroma characteristics to cigarettes, so that the aroma of the cigarettes can be improved.
The waste cigarette butts are discarded by people on the roadside or cigarette ends such as an ashtray, and the cigarette butts are wide in raw material source and low in cost; the invention selects the cigarette end with yellow color, and the tar content is higher.
In a first aspect, the present invention provides a method of preparing a tar extract having aromatic properties from waste cigarette butts, the method comprising the steps of:
(1) adding the waste cigarette butts into an organic solvent for ultrahigh pressure extraction to obtain an extracting solution;
(2) centrifuging the extracting solution, and distilling and concentrating the supernatant under reduced pressure to obtain the tar extract.
Preferably, in the step (1), the ratio of the waste cigarette butts to the organic solvent is 1g: 5-25 mL;
preferably, the organic solvent is at least one of methanol, ethanol, petroleum ether, n-hexane, dichloromethane and ethyl acetate.
Preferably, in the step (1), the pressure of the ultrahigh-pressure extraction is 100-700 MPa, the pressure maintaining time is 3-35 min, and the pressure relief time is 5-20 s.
Preferably, in the step (2), the rotation speed of the centrifugation is 500-2000 r/min, and the time is 1-3 min.
Preferably, in the step (2), the temperature of the reduced pressure distillation is 30-50 ℃, and the pressure is 0.1-5 mmH.
Preferably, the method further comprises the step of pre-treating the waste cigarette butts;
preferably, the pretreatment specifically comprises the following steps: and tearing off the wrapping paper of the waste cigarette butts, and cutting the tows into small sections with the length less than 1 cm.
In a second aspect, the invention also provides a tar extract prepared by the method.
In a third aspect, the invention also provides the application of the tar extract in preparing a perfume, wherein the tar extract is used as a perfuming component in the perfume.
In a fourth aspect, the invention also provides application of the tar extract in preparing cigarettes.
Preferably, the tar extract is added into cigarette auxiliary materials or cigarette secondary cut tobacco, and the addition amount of the tar extract is 2-5% of the weight of the cigarette;
preferably, the cigarette is a cigarette which is not burnt under heating
The invention has the beneficial effects that:
(1) the method utilizes the organic solvent ultrahigh-pressure extraction and reduced pressure distillation separation, removes harmful substances in the waste cigarette butt tar, retains the components with the aroma characteristics, is applied to the heating non-combustion cigarettes, improves the aroma, smoke and taste characteristics of the heating non-combustion cigarettes, and effectively solves the problem of low cigarette taste of the heating non-combustion cigarettes.
(2) According to the invention, the tar extract with higher extraction rate is obtained from the waste cigarette butts by optimizing the condition of organic solvent ultrahigh-pressure extraction. The invention takes the waste cigarette butts as raw materials, which not only can avoid the pollution of the cigarette butts to the environment, but also can utilize the byproduct tar after the cigarette is burnt and smoked.
Detailed Description
The present invention is described in detail with reference to specific examples, which are provided to facilitate the understanding of the technical solutions of the present invention by those skilled in the art, and the implementation or use of the present invention is not limited by the description of the present invention.
In the present invention, the raw materials and equipment used are commercially available or commonly used in the art, if not specified.
The methods in the examples are conventional in the art unless otherwise specified.
Example 1Preparation of Tar extract
A method of preparing a tar extract having aromatic properties from waste cigarette butts comprising the steps of:
(1) pretreatment of waste cigarette butts: tearing off tipping paper of the waste cigarette butts, and cutting the fiber tow part into small sections with the length of less than 1 cm;
(2) putting 100g of pretreated waste cigarette butts and 1L of 75% (v/v) ethanol solution into an ultrahigh pressure PE bag for mixing, putting the PE bag into a high-pressure kettle, pressurizing to 300MPa, keeping for 10min, and releasing pressure for 10s to obtain an extracting solution;
(3) centrifuging the extractive solution at 1000r/min for 2min, and concentrating the supernatant by vacuum distillation at 35 deg.C under 2mmH until no fraction is distilled out to obtain tar extract.
Performing GC/MS detection on the obtained tar extract, wherein the obtained tar extract comprises the components of furfural, furfuryl alcohol, ethylene glycol diacetate, 1- (1, 3-dioxolane-2-yl) acetone, 4-cyclopentene-1, 3-dione, methyl cyclopentenolone, nicotine, 2-acetylfuran, 2(5H) -furanone, 5-methylfuran aldehyde, 3-methyl-2-cyclopentene-1-one, methyl cyclopentenolone, benzyl alcohol, 2, 3-dimethyl-2-cyclopentenolone, ethyl cyclopentenolone, 5-hydroxymethyl furfural, vanillin, megastigmatrienone A, 2,4, 4-trimethylpentane-1, 3-diylbis (2-methylpropionate), Farnesol, 1-butyl-2-isobutyl phthalate, scopoletin, tributylprop-1-ene-1, 2, 3-tricarboxylate and tributyl citrate.
Wherein, the GC/MS conditions are as follows:
HP6890-5973 gas chromatography-mass spectrometer
(1) GC conditions were as follows:
a chromatographic column: ULTRA2(50m × 0.2mm i.d × 0.33 μm d.f.)
A detector: MS (Mass Spectrometry)
Carrier gas, flow rate: he, 0.6ml/min
Sample inlet temperature: 290 deg.C
Temperature rising procedure: 80 deg.C (1min)2 deg.C/min → 280 deg.C (10min)
Split ratio, sample injection amount: 1:10, 2. mu.l
(2) GC/MS conditions:
GC conditions were as follows: same as above
Transmission line temperature: 230 deg.C
Ion source temperature: 230 deg.C
Ionization energy: 70eV
Mass number range: 30 to 350u
Carrier gas: he (He)
MS spectrogram: NIST library
Example 2Aroma-producing properties of cigarette tar extracts
The tar extract obtained in example 1 was added to a filter auxiliary material of a cigarette that was not burned under heating at an addition ratio of 3% by weight of the cigarette, to prepare a cigarette sample a that was not burned under heating (HnB sample a).
The tar extract obtained in example 1 was added to a condensed auxiliary material for a non-burning, heated cigarette at an addition ratio of 2% by weight of the non-burning, heated cigarette, to prepare a non-burning, heated cigarette sample B (HnB sample B).
The tar extract obtained in example 1 was added to reconstituted tobacco shreds of a non-burning, heated cigarette at an addition ratio of 3% by weight of the non-burning, heated cigarette, to prepare a non-burning, heated cigarette sample C (HnB sample C).
After the cigarette samples prepared by the scheme and the cigarettes without the tar extracts are balanced for 24 hours in a constant-temperature and constant-humidity environment with the temperature of (20 +/-1) DEG and the relative humidity of (60 +/-3)%, sensory evaluation is carried out on HnB cigarette samples by referring to a tobacco product sensory evaluation method (YC/T415-.
TABLE 1 sensory evaluation results of cigarettes with different addition amounts of tar extract
Figure BDA0002290822020000061
As shown in Table 1, compared with a control group, the cigarette fragrance plumpness of the cigarette which is not combusted by heating is obviously improved, and the fragrance amount and the fragrance quality are improved; the concentration and the strength are increased, and the agglomeration property of the smoke is improved; the irritation is reduced, the moistening feeling is enhanced, and the sweet feeling is improved. After the tar extract prepared by the invention is added, the characteristics of smoke, aroma and taste of the cigarette which is not burnt after being heated can be effectively improved.
Example 3Selection of preparation Process conditions
1. Selection of ultra-high pressure extraction pressure
20g of pretreated waste cigarette butts and 200mL of 75% (v/v) ethanol solution are mixed and added into a high-pressure PE bag, the waste cigarette butts are extracted at 200MPa, 300MPa, 400MPa and 500MPa respectively, the extraction time is 10min, the pressure relief time is 10S, the influence of different pressures on the extraction effect is analyzed in a comparative way, and the detection result of the extracting solution is shown in Table 2. As is clear from Table 2, the 75% (v/v) aqueous ethanol solution was most effective in extracting the tar extract at 300 MPa.
TABLE 2 extraction Effect (mg/g) under different pressures
Figure BDA0002290822020000071
2. Selection of dwell time
20g of pretreated waste cigarette butts and 200mL of 75% (v/v) ethanol aqueous solution are mixed and added into a high-pressure PE bag, the waste cigarette butts are respectively extracted for 6min, 8min, 10min and 12min under the pressure of 300MPa, the pressure relief time is 10S, the influence of different extraction times on the extraction effect is analyzed in a comparative manner, and the detection result of the extracting solution is shown in Table 3. As can be seen from Table 3, the extraction efficiency was the best when the pressure was maintained for 10 min.
TABLE 3 extraction Effect (mg/g) for different dwell times
Figure BDA0002290822020000081
The above description is only an example of the present application, and the protection scope of the present application is not limited by these specific examples, but is defined by the claims of the present application. Various modifications and changes may occur to those skilled in the art to which the present application pertains. Any modification, equivalent replacement, improvement, etc. made within the technical idea and principle of the present application should be included in the protection scope of the present application.

Claims (5)

1. A method of preparing a tar extract having aromatic properties from waste cigarette butts, the method comprising the steps of:
(1) pretreatment of waste cigarette butts: tearing off tipping paper of the waste cigarette butts, and cutting the fiber tow part into small sections with the length of less than 1 cm;
(2) putting 100g of pretreated waste cigarette butts and 1L of 75% (v/v) ethanol solution into an ultrahigh pressure PE bag for mixing, putting the PE bag into a high-pressure kettle, pressurizing to 300MPa, keeping for 10min, and releasing pressure for 10s to obtain an extracting solution;
(3) centrifuging the extractive solution at 1000r/min for 2min, distilling the supernatant under reduced pressure at 35 deg.C under 2mmH to obtain tar extract;
the tar extract is used for being added into cigarette auxiliary materials or cigarette reconstituted tobacco, wherein the cigarette is a cigarette which is not combusted by heating.
2. A tar extract made by the method of claim 1.
3. Use of the tar extract of claim 2 for the preparation of cigarettes.
4. The application of claim 3, wherein the tar extract is added into cigarette auxiliary materials or cigarette re-making tobacco shreds, and the addition amount of the tar extract is 2-5% of the weight of the cigarette.
5. The use according to claim 4, wherein the cigarette is a heat non-combustible cigarette.
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0280935A2 (en) * 1987-02-28 1988-09-07 Messer Griesheim Gmbh Process for extracting organic substances from solids
CN101438855A (en) * 2008-11-27 2009-05-27 河南中烟工业公司 Maillard reaction product under ultra-high pressure condition and use thereof in tobacco
CN102952638A (en) * 2012-11-13 2013-03-06 广东中烟工业有限责任公司 Preparation method and application of tobacco endogenous spice of Boshan aromatic tobacco
CN102952639A (en) * 2012-11-13 2013-03-06 广东中烟工业有限责任公司 Preparation method of tobacco endogenous perfume and application thereof
CN107653064A (en) * 2017-09-27 2018-02-02 湖北中烟工业有限责任公司 A kind of inoxidizability is strong, the preparation method and applications of high fragrance Rome yellow chamomile fermentation absolute oil
CN108004024A (en) * 2018-01-16 2018-05-08 武汉黄鹤楼香精香料有限公司 A kind of ginkgo leaf cigarette is applied with quick-fried pearl essential oil and preparation method thereof and in cigarette
CN109938396A (en) * 2019-03-28 2019-06-28 江西中烟工业有限责任公司 A kind of preparation method of tobacco endogenous Maillard reaction flavor and the application in new tobacco products

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0280935A2 (en) * 1987-02-28 1988-09-07 Messer Griesheim Gmbh Process for extracting organic substances from solids
CN101438855A (en) * 2008-11-27 2009-05-27 河南中烟工业公司 Maillard reaction product under ultra-high pressure condition and use thereof in tobacco
CN102952638A (en) * 2012-11-13 2013-03-06 广东中烟工业有限责任公司 Preparation method and application of tobacco endogenous spice of Boshan aromatic tobacco
CN102952639A (en) * 2012-11-13 2013-03-06 广东中烟工业有限责任公司 Preparation method of tobacco endogenous perfume and application thereof
CN107653064A (en) * 2017-09-27 2018-02-02 湖北中烟工业有限责任公司 A kind of inoxidizability is strong, the preparation method and applications of high fragrance Rome yellow chamomile fermentation absolute oil
CN108004024A (en) * 2018-01-16 2018-05-08 武汉黄鹤楼香精香料有限公司 A kind of ginkgo leaf cigarette is applied with quick-fried pearl essential oil and preparation method thereof and in cigarette
CN109938396A (en) * 2019-03-28 2019-06-28 江西中烟工业有限责任公司 A kind of preparation method of tobacco endogenous Maillard reaction flavor and the application in new tobacco products

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
烟草香味成分的超高压萃取;付瑜 等;《烟草科技》;20081231;第31-36页 *
烟蒂回收利用研究;黄登峰;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20130215;第B027-744页 *

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