EP1782702B1 - Verfahren zur herstellung von regeneriertem tabakmaterial - Google Patents

Verfahren zur herstellung von regeneriertem tabakmaterial Download PDF

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Publication number
EP1782702B1
EP1782702B1 EP05748851A EP05748851A EP1782702B1 EP 1782702 B1 EP1782702 B1 EP 1782702B1 EP 05748851 A EP05748851 A EP 05748851A EP 05748851 A EP05748851 A EP 05748851A EP 1782702 B1 EP1782702 B1 EP 1782702B1
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EP
European Patent Office
Prior art keywords
adsorbent
amount
extract
extract solution
tsnas
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
Application number
EP05748851A
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English (en)
French (fr)
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EP1782702A1 (de
EP1782702A4 (de
Inventor
Shigenobu c/o JAPAN TOBACCO INC. TATSUOKA
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Japan Tobacco Inc
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Japan Tobacco Inc
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Publication of EP1782702A4 publication Critical patent/EP1782702A4/de
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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific substances
    • A24B15/245—Nitrosamines
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B3/00—Preparing tobacco in the factory
    • A24B3/14—Forming reconstituted tobacco products, e.g. wrapper materials, sheets, imitation leaves, rods, cakes; Forms of such products

Definitions

  • the present invention relates to a method of manufacturing a regenerated tobacco material.
  • Tobacco materials such as natural tobacco leaves, cut tobacco, midribs, stems and roots contain various components including nicotine, nitrosamines, hydrocarbons and proteins.
  • these components extracted from a natural tobacco material, are put back to a regenerated tobacco web manufactured from a residue of the extraction.
  • Some of these natural tobacco material components should desirably be reduced in amount or removed, while other ones should not be removed or even increased in amount, for a reason of smoking flavor or some other reason.
  • US 2002/134394 discloses a method for reducing nitrosamine content in tobacco by extraction with an aqueous solvent and activated charcoal or a resin and regenerating said tobacco.
  • WARFIELD "Research proposal: technology for TSNA removal from tobacco extracts” LEGACY TOBACCO DOCUMENTS LIBRARY, 1 February 2002 (2002-02-01), pages 1-6 : discloses a method to remove the TSNA form tobacco extract without removing nicotine in a large extent by adjusting the pH to 1-2 and then 4-5, which corresponds to the pKa of the nitrosamines.
  • U.S. Patent 5,810,020 discloses that nitrosamines are removed by a liquid-liquid extraction treatment using a great amount of crown ether.
  • Nitrosamines, TSNAs in particular, contained in natural tobacco materials are substances which should desirably be eliminated.
  • TSNAs are similar in structure to nicotine, which is a useful component, and therefore it is very difficult to remove TSNAs selectively without removing nicotine.
  • the present invention provides a method of manufacturing a regenerated tobacco material using an extract solution obtained by extraction from a natural tobacco material with an aqueous extracting solvent, and an extraction residue.
  • the inventors of the present invention pay attention to a highly hydrophobic adsorbent such as activated carbon as simple means for separating nicotine and TSNAs in an extract solution obtained from a natural tobacco material by extraction with an aqueous extracting solvent.
  • a strongly hydrophobic adsorbent such as activated carbon has a tendency of adsorbing TSNAs together with nicotine.
  • the inventors of the present invention has found that TSNAs can be significantly removed while suppressing the amount of adsorption of nicotine to a minimum level by controlling the adsorption time and the amount of the adsorbent employed. The present invention is based on these findings.
  • a method of manufacturing a regenerated tobacco material comprising (a) extracting a natural tobacco material with an aqueous extracting solvent to obtain an extract solution containing components of the natural tobacco material, and an extraction residue, (b) subjecting the extract solution to an adsorption separation operation using an adsorbent to reduce an amount of nitrosamines, (c) preparing a regenerated tobacco web using the extraction residue, and (d) adding at least a part of the extract solution, in which the amount of nitrosamines has been reduced, to the regenerated tobacco web, wherein the adsorbent is a strongly hydrophobic adsorbent, and the adsorption separation operation is carried out within 5-30 minutes, using the strongly hydrophobic adsorbent in an amount corresponding to 10 to 110% of the weight of soluble components in the extract solution.
  • the single figure is a flow diagram illustrating a method of manufacturing a regenerated tobacco material according to an embodiment of the present invention.
  • the present invention is a method of manufacturing a regenerated tobacco material by substantially removing TSNAs (N'-nitrosonornicotine (NNN), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), N'-nitrosoanatabine (NAT), etc.) from an extract solution obtained by extracting a natural tobacco material with an aqueous extracting solvent while suppressing loss of nicotine as much as possible, and adding the extract solution to a regenerated tobacco web prepared by using the extraction residue.
  • TSNAs N'-nitrosonornicotine
  • NNK 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
  • NAT N'-nitrosoanatabine
  • FIG. 1 is a flow diagram illustrating a method of manufacturing a regenerated tobacco material according to an embodiment of the present invention.
  • a natural tobacco material 11 is subjected to an extraction treatment S1 by mixing and stirring the natural tobacco material 11 and an extracting solvent 12.
  • the natural tobacco material 11 tobacco leaves, cut tobacco, midribs, stems, roots and a mixture of these can be used.
  • an aqueous solvent can be used.
  • the aqueous extracting solvent such as water may be alkaline or acidic. It is also possible to use, as the aqueous extracting solvent, a mixture of water and a water-miscible organic solvent as well. Examples of such an organic solvent are alcohols such as ethanol.
  • the extraction treatment S1 is carried out usually at a temperature of 50 to 100°C for 5 minutes to 6 hours.
  • the extraction mixture obtained is subjected to a separation operation S2 such as filtration to separate it into an extract solution 13 and an extraction residue 14.
  • the extract solution 13 contains watersoluble components in the natural tobacco material, such as nicotine and TSNAs.
  • the extraction residue 14 consists essentially of fibers.
  • a regenerated tobacco web 15 is manufactured by an ordinary method, using the extraction residue 14.
  • the regenerated tobacco web 15 may be partially or entirely constituted by the extraction residue 14.
  • the extract solution 13 obtained from the separation operation S2 is subjected to an adsorption treatment operation S4 using a strongly hydrophobic adsorbent.
  • the adsorption separation operation S4 can be carried out by bringing the extract solution 13 into contact with the strongly hydrophobic adsorbent.
  • the strongly hydrophobic adsorbent is an adsorbent generally known to have a high hydrophobicity. Examples thereof are activated carbon, a styrene-based porous resin, and an adsorbent in which a modifying group that further enhances the hydrophobic property (hydrophobic group), for example, bromine, is introduced to a styrene-based porous resin.
  • a modifying group that further enhances the hydrophobic property for example, bromine
  • the contact between the extract solution 13 and the strongly hydrophobic adsorbent can be achieved by adding particles of the strongly hydrophobic adsorbent to the extract 13, followed by stirring.
  • the contact between the extract 13 and the strongly hydrophobic adsorbent can be achieved by passing the extract solution 13 through an adsorbent bed filled with particles of the strongly hydrophobic adsorbent.
  • the amount of the strongly hydrophobic adsorbent used is that corresponds to 10 to 110% of the weight of the soluble components in the extract solution 13. If the amount of the strongly hydrophobic adsorbent is less than 10%, TSNAs in the extract solution cannot be sufficiently removed. On the other hand, if the amount of the adsorbent exceeds 110%, the amount of nicotine adsorbed significantly increases. It is preferable that the amount of the strongly hydrophobic adsorbent correspond to 10 to 50% of the weight of the soluble components in the extract 13. It should be noted that the amount of the soluble components in the extract can be determined by the freeze-dry method.
  • the contact time between the extrac solution 13 and the strongly hydrophobic adsorbent is 5-30 minutes. When the contact time is within 5-30 minutes, TSNAs can be eliminated while significantly suppressing the adsorption of nicotine.
  • the contact time is preferably 5 to 60 minutes, and more preferably, 5 to 30 minutes.
  • the pH value of the extract when brought into contact with the strongly hydrophobic adsorbent is preferably more than 2 but less than 10, and more preferably, more than 4 but less than 10 in the present invention.
  • the pH value can be adjusted by adding acid or alkali.
  • the temperature of the extract solution is preferably 0 to 100°C, and more preferably 20 to 60°C.
  • the extract that has been subjected to adsorption/separation is separated (S5) from the strongly hydrophobic adsorbent (spent adsorbent 17).
  • this separation can be carried out by filtration.
  • the contact between the extract and the strongly hydrophobic adsorbent is carried out by passing the extract through the strongly hydrophobic adsorbent bed, the extract after the adsorption process is, needless to mention, is flowed out of the bed of the strongly hydrophobic adsorbent in the state separated from the adsorbent.
  • the thus obtained extract 16 already subjected to the adsorption treatment is added (S5) partially or entirely to the regenerated tobacco web 15 after concentrating or without concentrating the extract, and thus a regenerated tobacco material 18 can be obtained.
  • a cigarette manufactured using the regenerated tobacco material 18 thus obtained exhibits a significantly reduced amount of TSNAs in the smoke when it is burned.
  • the amount of TSNAs was measured according to the method of measuring TSNAs in the cut tobacco of Arista (Official Method T-309, Determination of Nitrosamines in Whole Tobacco, made by the Department of Health, dated December 31, 1999). More specifically, for the measurement, the tobacco extract or adsorbent-treated liquid was subjected to LC-MS/MS. The amount of nicotine was measured by a method incompliance with German Institute for Normalization DIN 10373. More specifically, sodium hydroxide was added to the tobacco extract or adsorbent-treated liquid to make it alkaline, and then hexane was further added thereto. The resultant was mixed to make nicotine to transfer to the hexane phase, and the hexane phase alone was subjected to GC/FID for measurement.
  • activated carbon (average particle diameter: 1100 ⁇ m; specific surface area: 1638 m 2 /g) was added to the extract solution (pH: 6.0) in amounts (%) indicated in TABLE 1 with respect to the amount of soluble components of the extract solution, stirred for time periods (adsorption treatment times) indicated in TABLE 1 at a temperature of 25°C, and then filtrated.
  • the total amount of TSNAs and amount of nicotine contained in the extract solution (filtrate) after the adsorption treatment were analyzed. The results are also indicated in TABLE 1.
  • TABLE 1 further indicates the rate of change in total TSNA and nicotine.
  • TABLE 1 Amount of adsorbent (%) Adsorption treatment time (min) Total amount of TSNAs ( ⁇ g/g) Amount of nicotine (mg/g) Rate of change in total TSNAs (a) Rate of change in nicotine (b) Difference (a-b) Untreated - - 30.5 23.4 - - - Ex. 1 13 15 11.8 17.2 -61% -26% -35% Ex. 2 13 30 10.0 16.4 -67% -30% -37% Ex. 3 13 60 8.9 14.1 -71% -39% -31% Ex.
  • the extracts subjected to the adsorption treatment in Examples 1 - 3 and 5 - 6 were added to the regenerated tobacco webs, respectively, preparing regenerated tobacco materials.
  • Example 11 is a comparative example
  • the extracts subjected to the adsorption treatment in Examples 9 - 11 were added to the regenerated tobacco webs, respectively, preparing regenerated tobacco materials.
  • Examples 12 - 14 (example 14 is a comparative example)
  • the extracts subjected to the adsorption treatment in Examples 12 - 14 were added to the regenerated tobacco webs, respectively, preparing regenerated tobacco materials.
  • the cut tobacco was extracted in accordance with the procedures of Examples 1 - 8, and the extracts thus obtained were adjusted to a pH of 2.0 or 10.0 by adding acid (acetic acid) or alkali (sodium hydroxide).
  • the extracts were treated with activated carbon used in Examples 12 - 14 under respective conditions indicated in TABLE 4.
  • the results of the analysis of the total amount of TSNAs and amount of nicotine contained in the extract (filtrate) after the adsorption treatment were also indicated in TABLE 4.
  • Examples 21 - 38 (examples 23, 24, 27-29, 34 and 38 are comparative examples)
  • Examples 39 - 47 (examples 41, 44 and 47 are comparative examples)
  • the present invention it is possible to separate nicotine and TSNAs from an extract solution obtained from a natural tobacco material in a relatively simple manner, and to manufacture a regenerated tobacco material substantially freed of TSNAs while suppressing the loss of nicotine as much as possible.

Claims (6)

  1. Verfahren zur Herstellung eines regenerierten Tabakmaterials, umfassend:
    (a) Extrahieren eines natürlichen Tabakmaterials mit einem wässrigen Extraktionslösungsmittel, um eine Bestandteile des natürlichen Tabakmaterials enthaltende Extraktlösung und einen Extraktrückstand zu erhalten;
    (b) die Extraktionslösung wird einem Adsorptionstrennungsprozess unter Verwendung eines Adsorbens unterzogen, um einen Anteil an Nitrosaminen zu verringern;
    (c) Herstellen einer regenerierten Tabakmatrix unter Verwendung des Extraktionsrückstandes; und
    (d) Hinzufügen wenigstens eines Teils der Extraktlösung, in welcher der Anteil an Nitrosaminen verringert wurde, zur regenerierten Tabakmatrix,
    wobei das Adsorbens ein stark hydrophobes Adsorbens ist, und der Adsorptionstrennungsvorgang 5 bis 30 Minuten lang unter Verwendung des stark hydrophoben Adsorbens in einer Menge ausgeführt wird, die 10 bis 110 Gew.-% an löslichen Bestandteilen der Extraktlösung entspricht.
  2. Verfahren nach Anspruch 1, wobei das Adsorbens ein Styrol-basiertes poröses Harz, ein aktivierter Kohlenstoff oder ein Adsorbens ist, in welchem eine hydrophobe Gruppe an eine Oberfläche des Adsorbens gebunden ist.
  3. Verfahren nach Anspruch 1, wobei das stark hydrophobe Adsorbens in einer Menge eingesetzt wird, die 15 bis 60 Gew.-% der löslichen Bestandteile der Extraklösung entspricht.
  4. Verfahren nach Anspruch 1, wobei der pH-Wert der Extraktlösung über 2, jedoch unter 10 liegt.
  5. Verfahren nach Anspruch 1, wobei der pH-Wert des Extraktes über 4, jedoch unter 10 liegt.
  6. Verfahren nach Anspruch 1, wobei der Adsorbtionstrennungsprozess bei einer Temperatur von 0 bis 100°C durchgeführt wird.
EP05748851A 2004-06-16 2005-06-09 Verfahren zur herstellung von regeneriertem tabakmaterial Not-in-force EP1782702B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004178665 2004-06-16
PCT/JP2005/010586 WO2005122803A1 (ja) 2004-06-16 2005-06-09 再生タバコ材の製造方法

Publications (3)

Publication Number Publication Date
EP1782702A1 EP1782702A1 (de) 2007-05-09
EP1782702A4 EP1782702A4 (de) 2009-11-11
EP1782702B1 true EP1782702B1 (de) 2011-04-20

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Application Number Title Priority Date Filing Date
EP05748851A Not-in-force EP1782702B1 (de) 2004-06-16 2005-06-09 Verfahren zur herstellung von regeneriertem tabakmaterial

Country Status (6)

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EP (1) EP1782702B1 (de)
JP (1) JP4408289B2 (de)
AT (1) ATE505960T1 (de)
DE (1) DE602005027581D1 (de)
RU (1) RU2336789C1 (de)
WO (1) WO2005122803A1 (de)

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WO2007032433A1 (ja) * 2005-09-15 2007-03-22 Japan Tobacco Inc. 再生タバコ材の製造方法
EP1951074B1 (de) * 2005-11-07 2014-07-02 Swedish Match North Europe AB Verfahren für die herstellung von nikotin mit reduziertem gehalt an nitrosaminen
JP2008125498A (ja) * 2006-11-27 2008-06-05 Tetsuro Asao タバコ葉の製造方法
US9049886B2 (en) * 2007-01-26 2015-06-09 Philip Morris Usa Inc. Methods and apparatus for the selective removal of constituents from aqueous tobacco extracts
CN101940361B (zh) * 2010-10-11 2012-09-19 广东中烟工业有限责任公司 一种从废次烟叶中提取烟叶有效成分的方法
EP2526787A1 (de) 2011-05-26 2012-11-28 Philip Morris Products S.A. Verfahren zur Verringerung der Bildung von tabakspezifischen Nitrosaminen in Tabakhomogenaten
CN102920012B (zh) * 2012-09-03 2016-04-20 上海聚华科技股份有限公司 通过烟叶再造烟草梗丝的方法
CN102907760A (zh) * 2012-09-03 2013-02-06 上海聚华科技股份有限公司 调控烟草物化学成分的方法
WO2014141201A2 (en) 2013-03-15 2014-09-18 Fall Safall Method of reducing tobacco-specific nitrosamines
CN103393210B (zh) * 2013-04-17 2015-09-30 杭州利群环保纸业有限公司 改善造纸法再造烟叶抽吸品质的方法
WO2014196033A1 (ja) * 2013-06-05 2014-12-11 日本たばこ産業株式会社 たばこ原料の製造方法
RU2639111C1 (ru) 2014-02-26 2017-12-19 Джапан Тобакко Инк. Способ экстракции придающего аромат компонента и способ получения элемента композиции предпочитаемого изделия
KR101851090B1 (ko) 2014-02-26 2018-04-20 니뽄 다바코 산교 가부시키가이샤 담배 원료의 제조 방법
CA2940690C (en) * 2014-02-26 2019-01-22 Japan Tobacco Inc. Extraction method of flavor constituent and manufacturing method of composition element of favorite item
CN104172462B (zh) * 2014-08-13 2016-03-30 安徽中烟工业有限责任公司 一种造纸法再造烟叶中烟梗提取液的纯化方法
CN104705779B (zh) * 2015-01-28 2016-08-17 中国烟草总公司郑州烟草研究院 一种改善梗丝品质的加工方法
CN105077571A (zh) * 2015-09-01 2015-11-25 广西中烟工业有限责任公司 酶解萃取-美拉德反应复合技术制备烟草薄片的方法
US11419360B2 (en) * 2015-09-08 2022-08-23 Philip Morris Products S.A. Method of producing high tensile strength homogenized tobacco material
CN107802024B (zh) * 2017-10-25 2020-04-28 江苏中烟工业有限责任公司 一种含吸附剂的低温卷烟用烟芯材料的制备方法
WO2023119517A1 (ja) * 2021-12-22 2023-06-29 日本たばこ産業株式会社 漂白されたたばこ残渣およびその製造方法、再生たばこ材料およびその製造方法、並びにたばこ製品
WO2023119516A1 (ja) * 2021-12-22 2023-06-29 日本たばこ産業株式会社 たばこ香味液の製造方法、たばこ香味液、再生たばこ材料、およびたばこ製品

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Also Published As

Publication number Publication date
EP1782702A1 (de) 2007-05-09
DE602005027581D1 (de) 2011-06-01
RU2336789C1 (ru) 2008-10-27
JPWO2005122803A1 (ja) 2008-04-10
WO2005122803A1 (ja) 2005-12-29
JP4408289B2 (ja) 2010-02-03
RU2006143197A (ru) 2008-06-20
ATE505960T1 (de) 2011-05-15
EP1782702A4 (de) 2009-11-11

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