EP4691272A1 - Tobacco extract and method for producing same, tobacco material, tobacco rod, flavor inhaler, and smokeless tobacco - Google Patents

Tobacco extract and method for producing same, tobacco material, tobacco rod, flavor inhaler, and smokeless tobacco

Info

Publication number
EP4691272A1
EP4691272A1 EP23931940.3A EP23931940A EP4691272A1 EP 4691272 A1 EP4691272 A1 EP 4691272A1 EP 23931940 A EP23931940 A EP 23931940A EP 4691272 A1 EP4691272 A1 EP 4691272A1
Authority
EP
European Patent Office
Prior art keywords
tobacco
extract
neophytadiene
tobacco extract
alkanes
Prior art date
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.)
Pending
Application number
EP23931940.3A
Other languages
German (de)
French (fr)
Inventor
Yoshinobu SHIRAHASHI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Japan Tobacco Inc
Original Assignee
Japan Tobacco Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
Publication of EP4691272A1 publication Critical patent/EP4691272A1/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10Chemical features of tobacco products or tobacco substitutes
    • A24B15/16Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
    • 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
    • A24B15/26Use of organic solvents for extraction
    • 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
    • A24B15/28Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/32Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds

Definitions

  • the present invention relates to a tobacco extract and method for producing the same, a tobacco material, a tobacco rod, a flavor inhaler, and a smokeless cigarette.
  • Neophytadiene a volatile component that is contained in large amounts in leaf tobacco, is a diterpenoid having a molecular weight of 278.5.
  • Neophytadiene is a liquid at room temperature, and is odorless on its own, but is known as a major component of burning cigarette smoke.
  • Neophytadiene is also known as an additive for electronic cigarettes that improves taste and promotes a tobacco-like flavor (PTL 1 and 2).
  • PTL 3 through 6 are known as methods for extracting and purifying neophytadiene from leaf tobacco.
  • a problem with these methods is that large amounts of consumable materials are required, such as organic solvents and stationary phases in chromatography.
  • alkanes are major constituents of the wax component of the epicuticle, the outermost layer covering the leaf, and are contained in amounts of 5 to 10 mg per 1,000 square centimeters of leaf tobacco.
  • the method disclosed in NPL 1, for example, is known as a method for extracting and purifying alkanes from leaf tobacco. In this method, however, a broad range of components such as nicotine are eluted, and these components are thus still left over by the final step. Specifically, even though the resulting extract is generally evaluated on the basis of purity, undetectable contamination such as that noted above may still be a concern in methods of purification for achieving high purity.
  • neophytadiene- or alkane-containing extracts are not readily obtained efficiently from raw tobacco material in a simple manner, and further improvements are needed.
  • An object of the present invention is to provide: a method for producing a tobacco extract that allows neophytadiene- or alkane-containing extracts of high purity to be efficiently obtained from tobacco raw material in a simple manner; a tobacco extract produced by the method; a tobacco material comprising the tobacco extract; a tobacco rod; a flavor inhaler; and a smokeless cigarette.
  • the present invention can provide: a method for producing a tobacco extract that allows a neophytadiene- or alkane-containing extract of high purity to be efficiently obtained from tobacco raw material in a simple manner; a tobacco extract produced by the method; a tobacco material comprising the tobacco extract; a tobacco rod; a flavor inhaler; and a smokeless cigarette.
  • the method for producing the tobacco extract according to the present embodiment comprises the following steps: step 1 for preparing tobacco raw material; step 2 for subjecting the tobacco raw material to solid-liquid extraction using an aprotic solvent to remove the solids and obtain an organic phase; step 3 for removing the aprotic solvent from the organic phase to obtain a residue; and step 4 for distilling the residue at reduced pressure to obtain a tobacco extract comprising neophytadiene and a tobacco extract comprising alkanes.
  • the crude extract obtained from the tobacco raw material is distilled at reduced pressure, making it possible to control the amounts of the organic solvent and stationary phase that are used, and allowing tobacco-derived pigments and alkaloids that are a concern during the purification process to be removed in advance.
  • the method thus allows an extract comprising highly pure neophytadiene or alkanes to be efficiently obtained from tobacco raw material in a simple manner.
  • the method according to the present embodiment can furthermore comprise other steps besides said steps 1 through 4.
  • step 5 for subjecting the organic phase obtained in step 2 to liquid-liquid extraction using water or an aqueous solution of an acid to remove the aqueous phase can furthermore be included between steps 2 and 3.
  • step 6 for subjecting the organic phase obtained in step 2 or in step 5 to normal phase chromatography using n-hexane as the mobile phase can furthermore be included between steps 2 and 3.
  • a flowchart showing an example of a method according to the present embodiment is shown in Fig. 1 . The steps of the method according to the present embodiment will be described in detail below, but the method according to the present embodiment is not limited thereto.
  • the tobacco raw material is prepared in this step.
  • the tobacco raw material is not particularly limited, provided that it contains tobacco components; leaf tobacco can be used, for example.
  • types of tobacco leaf include, but are not particularly limited to, flue-cured (yellow), burley, orient, or native varieties, and other Nicotiana tabacum and Nicotiana rustica varieties. These leaf tobacco varieties may be used alone or in combinations of two or more. Of these, at least one leaf tobacco selected from the group consisting of flue-cured and burley varieties is preferred , and flue-cured is more preferred, because of the greater neophytadiene and alkane content.
  • the form of the leaf tobacco is not particularly limited, but is preferably a fine-ground leaf tobacco in the interests of better extraction efficiency. Solids discarded as waste material during the leaf tobacco expansion process or leaf tobacco dust discarded from leaf tobacco raw material factories may also be used as leaf tobacco.
  • the tobacco raw material is subjected to solid-liquid extraction using an aprotic solvent to remove the solids and obtain an organic phase in this step.
  • aprotic solvent to remove the solids and obtain an organic phase in this step.
  • neophytadiene and alkanes contained in the tobacco raw material are extracted in the form of a crude extract.
  • Water-insoluble organic solvents are preferred, and C5-6 hydrocarbons are more preferred, as the aprotic solvent serving as the extraction solvent.
  • hexane or heptane is preferred as the aprotic solvent.
  • the aprotic solvent is preferably added in an amount of 100 parts by weight or more, and more preferably 300 to 1000 parts by weight, per 100 parts by weight tobacco raw material.
  • the extraction can be effected by stirring, for example, the aprotic solvent containing the tobacco raw material.
  • the extraction temperature is preferably between 20 and 50°C, while the extraction time is preferably 5 minutes or more, and more preferably 3 hours or more. Solids (extracted residue) can be eliminated by, for example, being filtered using a stainless steel mesh to separate the organic phase and the solids.
  • the organic phase of step 2 is subjected to liquid-liquid extraction using water or an aqueous solution of an acid to remove the aqueous phase.
  • this step is optional and, if implemented, is carried out between step 2 and step 3 described below.
  • this step is preferably included in the method according to the present embodiment because alkaloids such as nicotine can be more effectively removed via this step.
  • the aqueous solution of an acid is preferably an aqueous solution of sulfuric acid, citric acid, or oxalic acid.
  • the pH of the aqueous solution of an acid is preferably less than 7, more preferably 3 or less, and even more preferably between 1 and 3, in the interests of ensuing that alkaloids such as nicotine more easily migrate to the aqueous layer.
  • the pH of the aqueous solution of an acid in the present specification is the value measured using a benchtop pH meter (tradename, by HORIBA).
  • the water is preferably added in an organic phase (step 2) to water volume ratio (organic phase:water) of 1 to 100:100, and more preferably 10 to 100:100.
  • the extraction solvent is an aqueous solution of an acid
  • the aqueous solution of an acid is preferably added in an organic phase (step 2) to acid aqueous solution ratio (organic phase:acid aqueous solution) of 1 to 1000:100, and more preferably 10 to 500:100, although the amount will depend on the pH of the aqueous solution of an acid.
  • the liquid-liquid extraction can be effected by stirring the mixture.
  • the extraction can be effected in batch mode using a stirring device, or can be effected in continuous mode using a counter-current distribution extractor such as a mixer-settler or a multi-stage liquid-liquid extraction column.
  • the extraction temperature is preferably between 0 and 30°C, while the extraction time is preferably 1 to 60 minutes.
  • a salt such as sodium chloride may also be added to the mixture during the liquid-liquid extraction.
  • a desiccant such as anhydrous sodium sulfate may be added to the extraction liquid obtained via the isolation and removal of the aqueous phase to dehydrate the extraction liquid.
  • this step the organic phase obtained in step 2 or in step 5 is subjected to normal phase chromatography using n-hexane as the mobile phase.
  • this step is optional and, if implemented, is carried out between step 2 (or step 5, if implemented) and step 3 described below.
  • this step is preferably included in the method according to the present embodiment because impurities can be more effectively removed via this step.
  • a "flavor inhaler” refers to an article with which a user inhales flavor.
  • Flavour inhalers are broadly divided into “combusted flavor inhalers,” in which flavor is produced via combustion, and “non-combusted flavor inhalers,” in which flavor is produced without burning.
  • Non-combusted flavor inhalers are furthermore broadly divided into “heat-not-burn flavour inhalers,”in which flavor is produced via heating, and “non-combusted/non-heated flavor inhalers,” in which flavor is produced without being heated.
  • a combination of a device for generating an aerosol such as a heating device or an atomizing device
  • a heat-not-burn flavor inhaler is referred to as a heat-not-burn flavor inhalation system.
  • Fig. 2 shows an embodiment of a heat-not-burn flavor inhaler according to the present embodiment.
  • the heat-not-burn flavor inhaler 20 comprises: a tobacco rod 20A; a cylindrical cooling portion 20B having a perforation in the perimeter; and a filter portion 20C.
  • the heat-not-burn flavour inhaler 20 may have other members.
  • the axial length of the heat-not-burn flavor inhaler 20 is not particularly limited, but is preferably 40 mm to 90 mm, more preferably 50 mm to 75 mm, and even more preferably 50 mm to 60 mm.
  • the cooling portion 20B is preferably composed of a cylindrical member.
  • the cylindrical member may be, for example, a paper tube 23 that is obtained by processing cardboard into a cylindrical shape.
  • the cooling portion 20B may also be formed by a sheet which is a thin material that is creased and then fluted, gathered and folded in order to form channels. Examples of such materials that can be used include sheet materials selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate, and aluminum foil.
  • the total surface area of the cooling portion 20B is prepared, as appropriate, taking into account the cooling efficiency, but can be 300 to 1000 mm 2 /mm, for example.
  • the cooling portion 20B is preferably provided with a perforations 24.
  • the perforation 24 allows external air to be introduced into the cooling segment 20B during inhalation. As a result, the aerosol vaporized component that is generated when the tobacco rod 20A is heated will come into contact with the external air and cool off, and will thus become liquefied to form an aerosol.
  • the diameter of the perforation 24 (length across) is not particularly limited, but may be 0.5 mm to 1.5 mm, for example.
  • the number of perforations 24 is not particularly limited, and may be one or more. Multiple perforations 24 may be provided on the circumference of the cooling portion 20B, for example.
  • the cooling portion 20B may be formed into a rod shape having an axial length of 7 to 28 mm, for example.
  • the axial length of the cooling portion 20B may be 20 mm, for example.
  • the cooling portion 20B has a substantially circular axial cross-sectional shape, which can be 5 to 10 mm in diameter.
  • the cooling portion can be approximately 7 mm in diameter, for example.
  • the configuration of the filter portion 20C is not particularly limited, but may be composed of one or more filling layers.
  • the outside of the filling layer may be wrapped with one or more sheets of wrapper.
  • the ventilation resistance of the filter portion 20 may be modified, as appropriate, depending on, for example, the amount and material of the filler with which the filter portion 20C is filled.
  • the ventilation resistance can be increased by increasing the amount of cellulose acetate fibers with which the filter portion 20C is filled.
  • the packing density of cellulose acetate fibers may be 0.13 to 0.18 g/cm 3 .
  • the ventilation resistance is the value determined using a ventilation resistance analyzer (trade name: SODIMAX, by SODIM).
  • the circumferential length of the filter portion 20C is not particularly limited, but is preferably 16 to 25 mm, more preferably 20 to 24 mm, and even more preferably 21 to 23 mm.
  • the filter portion 20C can have an axial (horizontal direction in Fig. 2 ) length of 4 to 10 mm, which can be selected so as to result in a ventilation resistance of 15 to 60 mmH 2 O per segment.
  • the axial length of the filter portion 20C is preferably 5 to 9 mm, and more preferably 6 to 8 mm.
  • the cross-sectional shape of the filter portion 20C is not particularly limited, but may be circular, elliptical, or polygonal, for example. Fragrance-containing destructible capsules, fragrance beads, and fragrances can also be directly added to the filter portion 20C.
  • the filter portion 20C may comprise a center hole portion as the first segment 25.
  • the center hole portion may be composed of a first filling layer 25a having one or more hollow portions, and an inner plug wrapper (inside rolling paper) 25b that covers the filling layer.
  • the center hole portion has the function of increasing the strength of the mouthpiece portion.
  • the shape of the center hole portion may be retained by means of thermoforming, without the inner plug wrapper 25b being provided.
  • the first segment 25 and the second segment 26 are connected by an outer plug wrapper (outer rolling paper )27.
  • the outer plug wrapper 27 may be cylindrical paper, for example.
  • the tobacco rod 20A, cooling portion 20B, and the connected first segment 25 and second segment 26 can be connected by means of mouthpiece lining paper 28. These connections may be formed, for example, by coating the inside surface of the mouthpiece lining paper 28 with a glue such as a vinyl acetate-based glue, and wrapping the three members noted above. These members may also be connected by multiple separate connections with a plurality of lining papers.
  • the heating device 10 comprises: a body 11, a heater 12, a metal tube 13, a battery unit 14, and a control unit 15.
  • the body 11 has a tubular recess 16, where the heater 12 and metal tube 13 are disposed at positions facing the tobacco rod 20A inserted therein.
  • the heater 12 can be a heater employing electrical resistance, where heating by the heater 12 is effected by the supply of electrical power from the battery unit 14 per commands from the control unit 15, which controls the temperature. Heat emitted from the heater 12 is transferred through the highly thermoconductive metal tube 13 to the tobacco rod 20A.
  • Fig. 3 depicts an embodiment in which the heating device 10 heats the tobacco rod 20A from the outside, but the rod may also be heated from the inside.
  • the heating temperature of the heating device 10 is not particularly limited, but is preferably 400°C or below, more preferably 150 to 400°C, and even more preferably 200 to 350°C. The heating temperature refers to the temperature of the heater of the heating device 10.
  • Fig. 4 is shows one embodiment of the non-combusted/non-heated flavor inhaler according to the present embodiment.
  • the non-combusted/non-heated flavor inhaler 30 has a power source unit 30D, a cartridge 30E, and a tobacco capsule 30F.
  • the non-combusted/non-heated flavor inhaler 30 has a shape extending from the undrawn end u (upstream) towards the drawing end d (downstream).
  • the cartridge 30E is attachable to, and detachable from, the power source unit 30D.
  • the tobacco capsule 30F is also attachable to, and detachable from, the cartridge 30E.
  • Fig. 5 shows an example of a tobacco capsule 30F.
  • the tobacco capsule 30F is a tobacco rod that has a flavor source 300 inside.
  • the flavor source 300 comprises the tobacco material according to the present embodiment.
  • the tobacco capsule 30F is connected to the cartridge 30E. Specifically, a portion of the tobacco capsule 30F is housed within the cartridge 30E.
  • the tobacco capsule 30F has: a housing 310 in which the flavor source 300 is housed; a mesh 320; a non-woven fabric 330; and a cap 340.
  • the aerosol atomized by the atomization unit 220 described below is introduced through the mesh 320 into the housing 310 and comes into contact with the flavor source 300, thereby allowing flavor to be added to the aerosol.
  • the aerosol is then drawn through the non-woven fabric 330 by the user.
  • the aerosol can be flavored without heating the flavor source 300. Also, essentially no aerosol is generated from the flavor source 300.
  • the length of the tobacco capsule 30F (housing 310) is preferably 40 mm or less, and more preferably 25 mm or less, in the direction in which the aerosol flows.
  • the length is also preferably 1 mm or more, and more preferably 5 mm or more, in the direction in which the aerosol flows.
  • the maximum length of the housing 310 of the tobacco capsule 30F (housing 310) is preferably 20 mm or less, and more preferably 10 mm or less, in the direction perpendicular to the direction in which the aerosol flows.
  • the maximum length of the tobacco capsule 30F (housing 310) is also preferably 1 mm or less, and more preferably 3 mm or less, in the direction perpendicular to the direction in which the aerosol flows.
  • the tobacco-containing flavor source 300 is composed of raw material pieces for flavoring the aerosol.
  • the lower limit of the size of the raw material pieces is preferably 0.2 to 1.2 mm, and more preferably 0.2 to 0.7 mm.
  • Examples of raw material pieces constituting the flavor source 300 that can be used include: cut tobacco comprising the tobacco extract according to the present embodiment; tobacco material according to the present embodiment that has been molded in the form of granules.
  • the flavor source 300 may include plants other than tobacco (such as mint or herbs) and flavor such as menthol.
  • the tobacco-containing flavor source 300 may furthermore comprising tobacco may comprise taste quality materials.
  • taste quality materials include ingredients that are sweet, sour, salty, savory, bitter, tart, rich, pungent, harsh, or astringent.
  • Saccharides, sugar alcohols, and sweeteners, etc. may be cited as examples of ingredients exhibiting sweetness.
  • Monosaccharides, disaccharides, oligosaccharides, and polysaccharides, etc. may be cited as examples of saccharides.
  • Natural sweeteners and synthetic sweeteners, etc. may be cited as examples of sweeteners.
  • the raw material pieces are obtained via sifting in accordance with JIS Z 8815 using a stainless steel sieve per JIS Z 8801, for example.
  • raw material pieces are sifted over a 20-minute period by means of drying and mechanical shaking using a stainless steel sieve having 0.71 mm openings to obtain raw material pieces passing through the stainless sieve having 0.71 mm openings.
  • the raw material pieces are then sifted over a 20-minute period by means of drying and mechanical shaking using a stainless steel sieve having 0.212 mm openings to remove raw material pieces passing through the stainless sieve having 0.212 mm openings.
  • raw material pieces constituting the flavor source 300 are raw material pieces that pass through a stainless steel sieve of a specified upper limit (0.71 mm openings) and that do not pass through a stainless steel sieve of a specified lower limit (0.212 mm openings).
  • the lower limit of the size of the raw material pieces constituting the flavor source 300 is thus defined by the openings of the stainless sieve of the specified lower limit.
  • the lower limit of the size of the raw material pieces constituting the flavor source 300 is thus also defined by the openings of the stainless sieve of the specified upper limit.
  • the amount of the loaded flavor source 300 housed in the housing 310 is preferably 300 mg or more, and more preferably 350 mg or more, in the interests of good flavour.
  • the power source unit 30D has a battery 110.
  • the battery 110 may be a disposable type battery or a rechargeable type battery.
  • the initial output voltage of the battery 110 is preferably in the range of 1.2 V to 4.2 V.
  • the battery 110 capacity is also preferably in the range of 100 mAh to 1000 mAh.
  • FIG. 7 shows a cross-sectional view of an example of a cartridge 30E
  • Fig. 8 shows the internal structure.
  • the cartridge 30E comprises a reservoir 210, an atomization unit 220, a flow path-forming element 230, an outer frame 240, and an end cap 250.
  • the cartridge 30E has a first flow path 200X, disposed downstream of the atomization unit 220, as the aerosol flow path.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

Provided is a method for producing a tobacco extract, the method making it possible to efficiently obtain an extract containing high-purity neofitadiene or alkane from a tobacco raw material, with a simple process. The method for producing a tobacco extract includes: a step 1 of preparing a tobacco raw material; a step 2 of subjecting the tobacco raw material to solid-liquid extraction using an aprotic solvent and removing solid components to obtain an organic phase; a step 3 of removing the aprotic solvent from the organic phase to obtain a residue; and a step 4 of subjecting the residue to vacuum distillation to obtain a tobacco extract containing neofitadiene and a tobacco extract containing alkane.

Description

    TECHNICAL FIELD
  • The present invention relates to a tobacco extract and method for producing the same, a tobacco material, a tobacco rod, a flavor inhaler, and a smokeless cigarette.
  • BACKGROUND ART
  • Neophytadiene, a volatile component that is contained in large amounts in leaf tobacco, is a diterpenoid having a molecular weight of 278.5. Neophytadiene is a liquid at room temperature, and is odorless on its own, but is known as a major component of burning cigarette smoke. Neophytadiene is also known as an additive for electronic cigarettes that improves taste and promotes a tobacco-like flavor (PTL 1 and 2).
  • The methods disclosed In PTL 3 through 6, for example, are known as methods for extracting and purifying neophytadiene from leaf tobacco. For the purposes of industrialized mass production, however, a problem with these methods is that large amounts of consumable materials are required, such as organic solvents and stationary phases in chromatography. There is furthermore no step for effectively eliminating alkaloids such as nicotine or pigments, and there is thus a need to figure out how to lower the content of these components prior to the final purification step.
  • On the other hand, alkanes are major constituents of the wax component of the epicuticle, the outermost layer covering the leaf, and are contained in amounts of 5 to 10 mg per 1,000 square centimeters of leaf tobacco. The method disclosed in NPL 1, for example, is known as a method for extracting and purifying alkanes from leaf tobacco. In this method, however, a broad range of components such as nicotine are eluted, and these components are thus still left over by the final step. Specifically, even though the resulting extract is generally evaluated on the basis of purity, undetectable contamination such as that noted above may still be a concern in methods of purification for achieving high purity.
  • CITATION LIST PATENT LITERATURE
  • NON-PATENT LITERATURE
  • 1.Agricultural and Biological Chemistry, 44(9), 2110-2124, 1980
  • SUMMARY OF INVENTION TECHNICAL PROBLEM
  • In the conventional methods noted above, neophytadiene- or alkane-containing extracts are not readily obtained efficiently from raw tobacco material in a simple manner, and further improvements are needed.
  • An object of the present invention is to provide: a method for producing a tobacco extract that allows neophytadiene- or alkane-containing extracts of high purity to be efficiently obtained from tobacco raw material in a simple manner; a tobacco extract produced by the method; a tobacco material comprising the tobacco extract; a tobacco rod; a flavor inhaler; and a smokeless cigarette.
  • SOLUTION TO PROBLEM
  • The present invention includes the following embodiments.
    1. [1] A method for producing a tobacco extract, comprising:
      • step 1 for preparing tobacco raw material;
      • step 2 for subjecting the tobacco raw material to solid-liquid extraction using an aprotic solvent to remove the solids and obtain an organic phase;
      • step 3 for removing the aprotic solvent from the organic phase to obtain a residue; and
      • step 4 for distilling the residue at reduced pressure to obtain a tobacco extract comprising neophytadiene and a tobacco extract comprising alkanes.
    2. [2] The method according to [1], wherein the aprotic solvent is a water-insoluble organic solvent.
    3. [3] The method according to [2], wherein the water-insoluble organic solvent is a C5-6 hydrocarbon.
    4. [4] The method according to any of [1] through [3], further comprising step 5, between step 2 and step 3, for subjecting the organic phase to liquid-liquid extraction using water or an aqueous solution of an acid to remove the aqueous phase.
    5. [5] The method according to [4], wherein the aqueous solution of an acid is an aqueous solution of sulfuric acid, citric acid, or oxalic acid.
    6. [6] The method according to [4] or [5], wherein the pH of the aqueous solution of the acid is less than 7.
    7. [7] The method according to any of [1] through [6], further comprising step 6, between step 2 and step 3, for subjecting the organic phase obtained in step 2 or in step 5 to normal phase chromatography using n-hexane as the mobile phase.
    8. [8] A tobacco extract comprising neophytadiene or alkanes produced by the method according to any of [1] through [7].
    9. [9] The tobacco extract according to [8], wherein the tobacco extract comprising neophytadiene comprises 80% by weight or more of neophytadiene.
    10. [10] The tobacco extract according to [8], wherein the tobacco extract comprising neophytadiene comprises 90% by weight or more of neophytadiene.
    11. [11] The tobacco extract according to [8], wherein the tobacco extract comprising alkanes comprises 50% by weight or more of alkanes.
    12. [12] The tobacco extract according to [8], wherein the alkanes have 25 to 35 carbons.
    13. [13] A tobacco material comprising the tobacco extract according to any of [8] through [12].
    14. [14] The tobacco material according to [13], which is a tobacco flavoring agent, a tobacco sheet, or cut tobacco.
    15. [15] The tobacco material according to [13] or [14], comprising 3500 ppm or more of neophytadiene and 5000 ppm or more of alkanes.
    16. [16] A tobacco rod comprising the tobacco material according to any of [13] through [15].
    17. [17] A flavor inhaler comprising the tobacco rod according to [16].
    18. [18] The flavor inhaler according to [17], which is a heat-not-burn flavor inhaler or a non-burning-non-heated flavor inhaler.
    19. [19] A smokeless cigarette comprising the tobacco material according to any of [13] through [15].
    ADVANTAGEOUS EFFECTS OF INVENTION
  • The present invention can provide: a method for producing a tobacco extract that allows a neophytadiene- or alkane-containing extract of high purity to be efficiently obtained from tobacco raw material in a simple manner; a tobacco extract produced by the method; a tobacco material comprising the tobacco extract; a tobacco rod; a flavor inhaler; and a smokeless cigarette.
  • BRIEF DESCRIPTION OF DRAWINGS
    • Fig. 1 is a flowchart showing an example of a method according to the present embodiment.
    • Fig. 2 is a schematic diagram showing an example of a heat-not-burn flavor inhaler according to the embodiment.
    • Fig. 3 is a schematic diagram showing an example of a heat-not-burn flavor inhalation system according to the present embodiment.
    • Fig. 4 is a schematic diagram showing an example of a non-combusted/non-heated flavor inhaler according to the embodiment.
    • Fig. 5 is a schematic diagram showing an example of a capsule for the non-combusted/non-heated flavor inhaler according to the present embodiment.
    • Fig. 6 is a schematic diagram showing an example of a power source unit for the non-burning-non-heated flavor inhaler according to the present embodiment.
    • Fig. 7 is a schematic diagram showing an example of a cartridge for the non-combusted/non-heated flavor inhaler according to the present embodiment.
    • Fig. 8 is a schematic diagram showing an example of a cartridge for the non-combusted/non-heated flavor inhaler according to the present embodiment.
    • Figure 9 is a chromatogram of the organic phase 1 obtained in step 2 of Example 1.
    • Figure 10 is a chromatogram of the organic phase 3 obtained in step 6 of Example 1.
    • Figure 11 is a chromatogram of a fraction obtained at a heating temperature 125°C in step 4 of Example 1.
    • Figure 12 is a chromatogram of a fraction obtained at a heating temperature 160°C in step 4 of Example 1.
    • Figure 13 is a chromatogram of the residue obtained in step 4 of Example 1.
    DESCRIPTION OF EMBODIMENTS [Method for producing tobacco extract]
  • The method for producing the tobacco extract according to the present embodiment comprises the following steps: step 1 for preparing tobacco raw material; step 2 for subjecting the tobacco raw material to solid-liquid extraction using an aprotic solvent to remove the solids and obtain an organic phase; step 3 for removing the aprotic solvent from the organic phase to obtain a residue; and step 4 for distilling the residue at reduced pressure to obtain a tobacco extract comprising neophytadiene and a tobacco extract comprising alkanes.
  • In the method for producing a tobacco extract according to the present embodiment, the crude extract obtained from the tobacco raw material is distilled at reduced pressure, making it possible to control the amounts of the organic solvent and stationary phase that are used, and allowing tobacco-derived pigments and alkaloids that are a concern during the purification process to be removed in advance. The method thus allows an extract comprising highly pure neophytadiene or alkanes to be efficiently obtained from tobacco raw material in a simple manner.
  • The method according to the present embodiment can furthermore comprise other steps besides said steps 1 through 4. For example, step 5 for subjecting the organic phase obtained in step 2 to liquid-liquid extraction using water or an aqueous solution of an acid to remove the aqueous phase can furthermore be included between steps 2 and 3. Step 6 for subjecting the organic phase obtained in step 2 or in step 5 to normal phase chromatography using n-hexane as the mobile phase can furthermore be included between steps 2 and 3. A flowchart showing an example of a method according to the present embodiment is shown in Fig. 1. The steps of the method according to the present embodiment will be described in detail below, but the method according to the present embodiment is not limited thereto.
  • (Step 1)
  • The tobacco raw material is prepared in this step. The tobacco raw material is not particularly limited, provided that it contains tobacco components; leaf tobacco can be used, for example. Examples of types of tobacco leaf include, but are not particularly limited to, flue-cured (yellow), burley, orient, or native varieties, and other Nicotiana tabacum and Nicotiana rustica varieties. These leaf tobacco varieties may be used alone or in combinations of two or more. Of these, at least one leaf tobacco selected from the group consisting of flue-cured and burley varieties is preferred , and flue-cured is more preferred, because of the greater neophytadiene and alkane content. The form of the leaf tobacco is not particularly limited, but is preferably a fine-ground leaf tobacco in the interests of better extraction efficiency. Solids discarded as waste material during the leaf tobacco expansion process or leaf tobacco dust discarded from leaf tobacco raw material factories may also be used as leaf tobacco.
  • (Step 2)
  • The tobacco raw material is subjected to solid-liquid extraction using an aprotic solvent to remove the solids and obtain an organic phase in this step. Through this step, neophytadiene and alkanes contained in the tobacco raw material are extracted in the form of a crude extract. Water-insoluble organic solvents are preferred, and C5-6 hydrocarbons are more preferred, as the aprotic solvent serving as the extraction solvent. Specifically, hexane or heptane is preferred as the aprotic solvent.
  • The aprotic solvent is preferably added in an amount of 100 parts by weight or more, and more preferably 300 to 1000 parts by weight, per 100 parts by weight tobacco raw material. The extraction can be effected by stirring, for example, the aprotic solvent containing the tobacco raw material. The extraction temperature is preferably between 20 and 50°C, while the extraction time is preferably 5 minutes or more, and more preferably 3 hours or more. Solids (extracted residue) can be eliminated by, for example, being filtered using a stainless steel mesh to separate the organic phase and the solids.
  • (Step 5)
  • In this step, the organic phase of step 2 is subjected to liquid-liquid extraction using water or an aqueous solution of an acid to remove the aqueous phase. In the method according to the present embodiment, this step is optional and, if implemented, is carried out between step 2 and step 3 described below. However, this step is preferably included in the method according to the present embodiment because alkaloids such as nicotine can be more effectively removed via this step. The aqueous solution of an acid is preferably an aqueous solution of sulfuric acid, citric acid, or oxalic acid. The pH of the aqueous solution of an acid is preferably less than 7, more preferably 3 or less, and even more preferably between 1 and 3, in the interests of ensuing that alkaloids such as nicotine more easily migrate to the aqueous layer. The pH of the aqueous solution of an acid in the present specification is the value measured using a benchtop pH meter (tradename, by HORIBA).
  • When the extraction solvent is water, the water is preferably added in an organic phase (step 2) to water volume ratio (organic phase:water) of 1 to 100:100, and more preferably 10 to 100:100. When the extraction solvent is an aqueous solution of an acid, the aqueous solution of an acid is preferably added in an organic phase (step 2) to acid aqueous solution ratio (organic phase:acid aqueous solution) of 1 to 1000:100, and more preferably 10 to 500:100, although the amount will depend on the pH of the aqueous solution of an acid. The liquid-liquid extraction can be effected by stirring the mixture. For example, the extraction can be effected in batch mode using a stirring device, or can be effected in continuous mode using a counter-current distribution extractor such as a mixer-settler or a multi-stage liquid-liquid extraction column. The extraction temperature is preferably between 0 and 30°C, while the extraction time is preferably 1 to 60 minutes. A salt such as sodium chloride may also be added to the mixture during the liquid-liquid extraction. A desiccant such as anhydrous sodium sulfate may be added to the extraction liquid obtained via the isolation and removal of the aqueous phase to dehydrate the extraction liquid.
  • (Step 6)
  • In this step, the organic phase obtained in step 2 or in step 5 is subjected to normal phase chromatography using n-hexane as the mobile phase. In the method according to the present embodiment, this step is optional and, if implemented, is carried out between step 2 (or step 5, if implemented) and step 3 described below. However, this step is preferably included in the method according to the present embodiment because impurities can be more effectively removed via this step.
  • The organic phase obtained in step 2 or step 5 can be concentrated using an evaporator, for example, prior to the normal phase chromatography. No particular limitations are imposed on the normal phase chromatography, but commercially available silica gel (Wakosil C-300, by FUJIFILM Wako Chemicals) can be used, for example. Isolation can be effected under the following conditions, for example, when using normal phase chromatography.
    • Column: Silica gel column chromatography (approximately 60 mm x 180 mm)
    • Mobile phase: n-hexane
    When isolation is effected under the above conditions, fractions can be eluted using the mobile phase in an amount ranging from the same amount to twice the amount of the volume of the silica gel that is used, and the fractions can be recovered to obtain the organic phase following the normal phase chromatography. (Step 3)
  • In this step, the aprotic solvent is removed from the organic phase obtained in step 2, step 5, or step 6 to obtain a residue. The aprotic solvent can be removed using an evaporator, for example.
  • (Step 4)
  • In this step, the residue obtained in step 3 is distilled at reduced pressure. As a result, a tobacco extract containing neophytadiene is obtained in the form of a fraction, and an extract containing alkanes is obtained in the form of residue. The distillation at reduced pressure can be effected, for example, using a glass tube oven or a short-path evaporator. The pressure in reduced-pressure distillation is preferably between 20 and 1000 Pa, in terms of absolute pressure. The temperature in reduced-pressure distillation is preferably between 120°C and 230°C, depending on the pressure during distillation. For example, if the pressure in reduced-pressure distillation is 20 Pa, in terms of absolute pressure, the temperature in the reduced-pressure distillation can be between 120°C and 150°C. If the pressure in reduced-pressure distillation is 1000 Pa, in terms of absolute pressure, the temperature in the reduced-pressure distillation can be between 190°C and 230°C. The duration of the reduced-pressure distillation will depend on the device or on the pressure and temperature during distillation, but is preferably between 1 minute and 6 hours, and more preferably between 5 minutes and 3 hours.
  • [Tobacco extract]
  • The tobacco extract according to the present embodiment is produced by the method for producing a tobacco extract according to the present embodiment, and comprises neophytadiene or alkanes. As noted above, the tobacco extract containing neophytadiene is obtained in the form of a fraction in the reduced-pressure distillation of step 4, and the tobacco extract comprising alkanes is obtained in the form of residue in the reduced-pressure distillation of step 4. The alkanescan be C25-35 alkanes. The tobacco extract according to the present embodiment is produced by the method for producing a tobacco extract according to the embodiment and thus is of high purity and has a low content of alkaloids such as nicotine or pigments.
  • The tobacco extract comprising neophytadiene according to the present embodiment preferably comprises 80% by weight or more, 90% by weight or more, even more preferably 95% by weight or more, and in particular preferably 97% by weight or more of neophytadiene. The tobacco extract comprising neophytadiene according to the present embodiment also preferably comprises 1% by weight or less, more preferably 0.1% by weight or less, and even more preferably zero nicotine.
  • The tobacco extract comprising alkanes according to the present embodiment preferably comprises 50% by weight or more, and in particular preferably 55% by weight or more of alkanes. The tobacco extract comprising alkanes according to the present embodiment also preferably comprises 1% by weight or less, more preferably 0.1% by weight or less, and even more preferably zero nicotine. The content of neophytadiene and alkanes in the tobacco extracts can be determined by GC-MS analysis.
  • [Tobacco material]
  • The tobacco material according to the present embodiment comprises the tobacco extract according to the present embodiment. The tobacco material according to the present embodiment can comprise, for example, 3500 ppm or more of neophytadiene and 5000 ppm or more of alkanes. The tobacco material according to the present embodiment is not particularly limited, provided that it includes the tobacco extract according to the present embodiment, where examples include tobacco flavoring agents such as liquid flavoring, tobacco sheets, and cut tobacco.
  • Tobacco sheets are obtained by molding a composition that includes aged tobacco leaf, for example, into the form of a sheet. There is no particular limitation as to the aged tobacco leaf used in the tobacco sheet, but aged tobacco leaf which has been de-stemmed and separated into lamina and midrib may be cited, for example. Aged tobacco leaf refers to tobacco leaves that have been treated, such as by being cured, and stored over the long-term in warehouses. In the present embodiment, "sheet" means a material having a pair of substantially parallel main faces and side faces. The tobacco sheet may be molded by well-known methods such as sheet-forming, casting, or rolling. Details on various types of tobacco sheets molded by such methods are disclosed in "Dictionary of Tobacco, Tobacco Academic Studies Center, March 31, 2009". The way in which the tobacco extract according to the present embodiment is added to the tobacco sheet is not limited.
  • For example, the tobacco extract according to the present embodiment may be dissolved in a solvent to prepare a tobacco flavoring agent in the form of a liquid, which may be used to spray or impregnate the finished tobacco sheet, or the tobacco extract according to the present embodiment may be added while the tobacco sheet is formed. Papermaking methods, for example, involves a process in which water-soluble components are extracted from aged tobacco leaf and separated into an aqueous extract and residue, a mixture of the fibrillated residue and pulp is made into paper, and a concentrate of the aqueous extract is added to the sheet that has been made, but the tobacco extract according to the present embodiment can be added to the aqueous extract. Casting methods involve a process in which a mixture is produced by mixing water, pulp, a binder, and ground aged tobacco, and the mixture is cast, but the tobacco extract according to the present embodiment can be added to the mixture. Rolling methods involve a process in which a mixture is produced by mixing water, pulp, a binder, and ground aged tobacco, and the mixture is rolled between a plurality of calendaring rolls, but the tobacco extract according to the present embodiment can be added to the mixture.
  • Furthermore, as disclosed in WO 2014/104078 A1 , ground aged tobacco and a binder can be mixed, the resulting mixture can be sandwiched between non-woven fabric, and the laminate can be molded into a given shape by thermal fusion to obtain a non-woven tobacco sheet. In this method,the tobacco extract according to the present embodiment can be added to the mixture.
  • The tobacco sheet may comprise an aerosol-generating substrate. The type of aerosol-generating substrate is not particularly limited, and extracts, or constituents thereof, from a variety of natural substances can be selected, depending on the intended application. Specific examples of aerosol-generating substrates can include polyhydric alcohols (such as glycerol, propylene glycol, sorbitol, xylitol, and erythritol), triacetin, 1,3-butanediol, or mixtures thereof. The content of the aerosol generating-substrate can be adjusted to varying amounts, depending on how it will be used in the tobacco product. For example, when the tobacco sheet contains an aerosol-generating substrate, the content of the aerosol generating-substrate is usually 5% by weight or more, preferably 10% by weight or more, and more preferably 15% by weight or more, and is usually 50% by weight or less, preferably 40% by weight or less, and more preferably 25% by weight or less, relative to the total weight of the tobacco sheet, in the interests of achieving good flavor.
  • Examples of cut tobacco include: aged tobacco leaf that has been cut to a predetermined size; the above tobacco sheet which has been cut to a predetermined sizes; or mixtures thereof. The size is not limited, and may be, for example, a width of 0.5 to 2 mmm and a length of 3 to 10 mm. Cut tobacco of this size is preferred when objects described below are to be filled with filler. Other examples of cut tobacco include strand types, where processed tobacco leaf is cut to a width of 0.5 to 2.0 mm and to a length that is longer than that of the cut tobacco noted above, and preferably about the same as that of the wrapper. The tobacco extract according to the present embodiment may be added to the cut tobacco or may be added to the uncut raw material.
  • The cut tobacco may also comprise the aerosol-generating substrate. When the cut tobacco contains an aerosol-generating substrate, the content of the aerosol generating-substrate is usually 5% by weight or more, preferably 10% by weight or more, and more preferably 15% by weight or more, and is usually 50% by weight or less, preferably 40% by weight or less, and more preferably 25% by weight or less, relative to the total weight of the cut tobacco, in the interests of generating enough aerosol and achieving good flavor.
  • [Tobacco rod, flavor inhaler]
  • The tobacco rod according to the present embodiment comprises the tobacco material according to the present embodiment. The flavor inhaler according to the present embodiment comprises the tobacco rod according to the present embodiment. The flavor inhaler according to the present embodiment is a heat-not-burn flavor inhaler or a non-combusted/non-heated flavor inhaler.
  • In the present embodiment, a "flavor inhaler" refers to an article with which a user inhales flavor. Flavour inhalers are broadly divided into "combusted flavor inhalers," in which flavor is produced via combustion, and "non-combusted flavor inhalers," in which flavor is produced without burning. Non-combusted flavor inhalers are furthermore broadly divided into "heat-not-burn flavour inhalers,"in which flavor is produced via heating, and "non-combusted/non-heated flavor inhalers," in which flavor is produced without being heated. A combination of a device for generating an aerosol (such as a heating device or an atomizing device) and a heat-not-burn flavor inhaler is referred to as a heat-not-burn flavor inhalation system.
  • (Heat-not-burn flavor inhaler)
  • Fig. 2 shows an embodiment of a heat-not-burn flavor inhaler according to the present embodiment. As shown in Figure 2, the heat-not-burn flavor inhaler 20 comprises: a tobacco rod 20A; a cylindrical cooling portion 20B having a perforation in the perimeter; and a filter portion 20C. The heat-not-burn flavour inhaler 20 may have other members. The axial length of the heat-not-burn flavor inhaler 20 is not particularly limited, but is preferably 40 mm to 90 mm, more preferably 50 mm to 75 mm, and even more preferably 50 mm to 60 mm. The circumferential length of the heat-not-burn flavor inhaler is preferably 16 mm to 25 mm, more preferably 20 mm to 24 mm, and even more preferably 21 mm to 23 mm. In an exemplary mode which may be cited, the length of the tobacco rod 20A is 20 mm, the length of the cooling segment 20B is 20 mm, and the length of the filter segment 20C is 7 mm. The length of the individual members can be modified, as appropriate, depending on manufacturability and required quality, for example. A first segment 25 is disposed in the embodiment shown in Fig. 2, but this need not be so disposed, and another option is for just a second segment 26 to be disposed downstream of the cooling portion 20B.
  • (1) Tobacco rod portion 20A
  • A sheet or cut tobacco containing the tobacco extract according to the present embodiment can be used as tobacco filler 21 in the tobacco rod 20A. The method for packing the tobacco filler 21 inside the wrapper 22 is not particularly limited but, for example, the tobacco filler 21 may be enclosed inside the wrapper 22, or the tobacco filler 21 may be packed inside a cylindrically shaped wrapper 22. Tobacco that is longer in the longitudinal direction, so as to be rectangularly shaped, may be packed in such a way that the pieces of tobacco, in the longitudinal direction, are randomly oriented in any direction in the wrapper 22, or may be packed while oriented in the axial direction of the tobacco rod 20A, or in a direction perpendicular thereto. The tobacco rod 20A is heated, so that the tobacco component, aerosol-generating substrate, and water included in the tobacco filler 21 are vaporized and are ready to be inhaled.
  • (2) Cooling portion 20B
  • The cooling portion 20B is preferably composed of a cylindrical member. The cylindrical member may be, for example, a paper tube 23 that is obtained by processing cardboard into a cylindrical shape. The cooling portion 20B may also be formed by a sheet which is a thin material that is creased and then fluted, gathered and folded in order to form channels. Examples of such materials that can be used include sheet materials selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate, and aluminum foil. The total surface area of the cooling portion 20B is prepared, as appropriate, taking into account the cooling efficiency, but can be 300 to 1000 mm2/mm, for example. The cooling portion 20B is preferably provided with a perforations 24. The perforation 24 allows external air to be introduced into the cooling segment 20B during inhalation. As a result, the aerosol vaporized component that is generated when the tobacco rod 20A is heated will come into contact with the external air and cool off, and will thus become liquefied to form an aerosol. The diameter of the perforation 24 (length across) is not particularly limited, but may be 0.5 mm to 1.5 mm, for example. The number of perforations 24 is not particularly limited, and may be one or more. Multiple perforations 24 may be provided on the circumference of the cooling portion 20B, for example.
  • The cooling portion 20B may be formed into a rod shape having an axial length of 7 to 28 mm, for example. The axial length of the cooling portion 20B may be 20 mm, for example. The cooling portion 20B has a substantially circular axial cross-sectional shape, which can be 5 to 10 mm in diameter. The cooling portion can be approximately 7 mm in diameter, for example.
  • (3) Filter portion
  • The configuration of the filter portion 20C is not particularly limited, but may be composed of one or more filling layers. The outside of the filling layer may be wrapped with one or more sheets of wrapper. The ventilation resistance of the filter portion 20 may be modified, as appropriate, depending on, for example, the amount and material of the filler with which the filter portion 20C is filled. For example, when the filler is cellulose acetate fibers, the ventilation resistance can be increased by increasing the amount of cellulose acetate fibers with which the filter portion 20C is filled. When the filler is cellulose acetate fibers, the packing density of cellulose acetate fibers may be 0.13 to 0.18 g/cm3. The ventilation resistance is the value determined using a ventilation resistance analyzer (trade name: SODIMAX, by SODIM).
  • The circumferential length of the filter portion 20C is not particularly limited, but is preferably 16 to 25 mm, more preferably 20 to 24 mm, and even more preferably 21 to 23 mm. The filter portion 20C can have an axial (horizontal direction in Fig. 2) length of 4 to 10 mm, which can be selected so as to result in a ventilation resistance of 15 to 60 mmH 2 O per segment. The axial length of the filter portion 20C is preferably 5 to 9 mm, and more preferably 6 to 8 mm. The cross-sectional shape of the filter portion 20C is not particularly limited, but may be circular, elliptical, or polygonal, for example. Fragrance-containing destructible capsules, fragrance beads, and fragrances can also be directly added to the filter portion 20C.
  • The filter portion 20C may comprise a center hole portion as the first segment 25. The center hole portion may be composed of a first filling layer 25a having one or more hollow portions, and an inner plug wrapper (inside rolling paper) 25b that covers the filling layer. The center hole portion has the function of increasing the strength of the mouthpiece portion. The shape of the center hole portion may be retained by means of thermoforming, without the inner plug wrapper 25b being provided. The first filling layer 25a may be, for example, a rod having an inside diameter of φ1.0 mm to φ5.0 mm, in which cellulose acetate fibers have been packed to a high density, and to which a triacetin-containing plasticizer has been added, in an amount of 6 to 20% by weight relative to the weight of the cellulose acetate, and cured. As the filling layer has a high fiber packing density, the air or aerosol will flow only through the hollow portion when drawn, with virtually none flowing through the first filling layer 25a. The first filling layer 25a of the center hole portion is a fiber filling layer, and the user will therefore experience little discomfort when touching the outside during use. The filter portion 20C may comprise a second segment 26. The second segment 26 is composed of a second filling layer 26a and an inner plug wrapper (inner rolling paper) 26b that covers the filling layer.
  • The first segment 25 and the second segment 26 are connected by an outer plug wrapper (outer rolling paper )27. The outer plug wrapper 27 may be cylindrical paper, for example. The tobacco rod 20A, cooling portion 20B, and the connected first segment 25 and second segment 26 can be connected by means of mouthpiece lining paper 28. These connections may be formed, for example, by coating the inside surface of the mouthpiece lining paper 28 with a glue such as a vinyl acetate-based glue, and wrapping the three members noted above. These members may also be connected by multiple separate connections with a plurality of lining papers.
  • (Heat-not-burn flavor inhalation system)
  • Fig. 3 shows an example of the heat-not-burn flavor inhalation system according to the present embodiment. In Fig. 3, the heat-not-burn flavor inhalation system comprises a heat-not-burn flavor inhaler 20 and a heating device 10 which heats the tobacco rod 20A from the outside.
  • The heating device 10 comprises: a body 11, a heater 12, a metal tube 13, a battery unit 14, and a control unit 15. The body 11 has a tubular recess 16, where the heater 12 and metal tube 13 are disposed at positions facing the tobacco rod 20A inserted therein. The heater 12 can be a heater employing electrical resistance, where heating by the heater 12 is effected by the supply of electrical power from the battery unit 14 per commands from the control unit 15, which controls the temperature. Heat emitted from the heater 12 is transferred through the highly thermoconductive metal tube 13 to the tobacco rod 20A. Fig. 3 depicts an embodiment in which the heating device 10 heats the tobacco rod 20A from the outside, but the rod may also be heated from the inside. The heating temperature of the heating device 10 is not particularly limited, but is preferably 400°C or below, more preferably 150 to 400°C, and even more preferably 200 to 350°C. The heating temperature refers to the temperature of the heater of the heating device 10.
  • [Non-combusted/non-heated flavor inhaler]
  • Fig. 4 is shows one embodiment of the non-combusted/non-heated flavor inhaler according to the present embodiment. The non-combusted/non-heated flavor inhaler 30 has a power source unit 30D, a cartridge 30E, and a tobacco capsule 30F. The non-combusted/non-heated flavor inhaler 30 has a shape extending from the undrawn end u (upstream) towards the drawing end d (downstream). The cartridge 30E is attachable to, and detachable from, the power source unit 30D. The tobacco capsule 30F is also attachable to, and detachable from, the cartridge 30E.
  • (1) Tobacco capsule
  • Fig. 5 shows an example of a tobacco capsule 30F. As shown in Fig. 5, the tobacco capsule 30F is a tobacco rod that has a flavor source 300 inside. The flavor source 300 comprises the tobacco material according to the present embodiment. The tobacco capsule 30F is connected to the cartridge 30E. Specifically, a portion of the tobacco capsule 30F is housed within the cartridge 30E.
  • The tobacco capsule 30F has: a housing 310 in which the flavor source 300 is housed; a mesh 320; a non-woven fabric 330; and a cap 340. The aerosol atomized by the atomization unit 220 described below is introduced through the mesh 320 into the housing 310 and comes into contact with the flavor source 300, thereby allowing flavor to be added to the aerosol. The aerosol is then drawn through the non-woven fabric 330 by the user. In the non-combusted/non-heated flavor inhaler 30, the aerosol can be flavored without heating the flavor source 300. Also, essentially no aerosol is generated from the flavor source 300.
  • The length of the tobacco capsule 30F (housing 310) is preferably 40 mm or less, and more preferably 25 mm or less, in the direction in which the aerosol flows. The length is also preferably 1 mm or more, and more preferably 5 mm or more, in the direction in which the aerosol flows. The maximum length of the housing 310 of the tobacco capsule 30F (housing 310) is preferably 20 mm or less, and more preferably 10 mm or less, in the direction perpendicular to the direction in which the aerosol flows. The maximum length of the tobacco capsule 30F (housing 310) is also preferably 1 mm or less, and more preferably 3 mm or less, in the direction perpendicular to the direction in which the aerosol flows.
  • The tobacco-containing flavor source 300 is composed of raw material pieces for flavoring the aerosol. The lower limit of the size of the raw material pieces is preferably 0.2 to 1.2 mm, and more preferably 0.2 to 0.7 mm. The smaller the size of the raw material piece constituting the flavor source 300, the grater the specific surface area, and thus the easier the flavor component will be released. Examples of raw material pieces constituting the flavor source 300 that can be used include: cut tobacco comprising the tobacco extract according to the present embodiment; tobacco material according to the present embodiment that has been molded in the form of granules. The flavor source 300 may include plants other than tobacco (such as mint or herbs) and flavor such as menthol. The tobacco-containing flavor source 300 may furthermore comprising tobacco may comprise taste quality materials. Examples of taste quality materials include ingredients that are sweet, sour, salty, savory, bitter, tart, rich, pungent, harsh, or astringent. Saccharides, sugar alcohols, and sweeteners, etc. may be cited as examples of ingredients exhibiting sweetness. Monosaccharides, disaccharides, oligosaccharides, and polysaccharides, etc. may be cited as examples of saccharides. Natural sweeteners and synthetic sweeteners, etc. may be cited as examples of sweeteners.
  • The raw material pieces are obtained via sifting in accordance with JIS Z 8815 using a stainless steel sieve per JIS Z 8801, for example. For example, raw material pieces are sifted over a 20-minute period by means of drying and mechanical shaking using a stainless steel sieve having 0.71 mm openings to obtain raw material pieces passing through the stainless sieve having 0.71 mm openings. The raw material pieces are then sifted over a 20-minute period by means of drying and mechanical shaking using a stainless steel sieve having 0.212 mm openings to remove raw material pieces passing through the stainless sieve having 0.212 mm openings. Specifically, raw material pieces constituting the flavor source 300 are raw material pieces that pass through a stainless steel sieve of a specified upper limit (0.71 mm openings) and that do not pass through a stainless steel sieve of a specified lower limit (0.212 mm openings). The lower limit of the size of the raw material pieces constituting the flavor source 300 is thus defined by the openings of the stainless sieve of the specified lower limit. The lower limit of the size of the raw material pieces constituting the flavor source 300 is thus also defined by the openings of the stainless sieve of the specified upper limit.
  • The amount of the loaded flavor source 300 housed in the housing 310 is preferably 300 mg or more, and more preferably 350 mg or more, in the interests of good flavour.
  • (2) Power source unit
  • An example of a power source unit 30D is shown in Fig. 6. The power source unit 30D has a battery 110. The battery 110 may be a disposable type battery or a rechargeable type battery. The initial output voltage of the battery 110 is preferably in the range of 1.2 V to 4.2 V. The battery 110 capacity is also preferably in the range of 100 mAh to 1000 mAh.
  • (3) Cartridge
  • An example of a cartridge 30E is shown in Figs. 7 and 8. Fig. 7 shows a cross-sectional view of an example of a cartridge 30E, and Fig. 8 shows the internal structure. The cartridge 30E comprises a reservoir 210, an atomization unit 220, a flow path-forming element 230, an outer frame 240, and an end cap 250. The cartridge 30E has a first flow path 200X, disposed downstream of the atomization unit 220, as the aerosol flow path.
  • An aerosol source 200 is stored in the reservoir 210. The reservoir 210 is located around the flow path-forming element 230 in a cross section perpendicular to the direction in which the aerosol flows (direction from the undrawn end toward the drawing end (upstream to downstream)). The reservoir 210 is located in a void space between the flow path-forming element 230 and the outer frame 240. The reservoir 210 is composed of, for example, a porous material such as a resin web or cotton. The reservoir 210 may also be composed of a tank that houses the liquid aerosol source 200. Examples of the aerosol source 200 include glycerol and propylene glycol.
  • The atomization unit 220 atomizes the aerosol source 200, without combustion, by means of power supplied from the battery 110. The atomization unit 220 is composed of electrically heated wire (coil) that has been wound at a predetermined pitch. The atomization unit 220 is preferably composed of electrically heated wire having a resistance in the range of 1.0 to 3.0 Ω. The predetermined pitch is preferably at least a value where the electrically heated wire is not in contact with itself, and low values are preferred. The predetermined pitch is preferably no more than 0.40 mm. The predetermined pitch should be constant to ensure stable atomization of the aerosol source 200. The predetermined pitch is the spacing between the centers of adjacent electrically heated wires.
  • The flow path-forming element 230 has a cylindrical shape forming the flow path 200X extending along the direction in which the aerosol flows. The outer frame 240 has a cylindrical shape in which the flow channel-forming element 230 is housed. The outer frame 240 extends further downstream than the end cap 250 and houses a portion of the tobacco capsule 30F. The end cap 250 is a cap that blocks, from the downstream side, the void space between the flow path-forming element 230 and the outer frame 240. The end cap 250 prevents the aerosol source 200 that is stored in the reservoir 210 from leaking toward the tobacco capsule 30F side.
  • [Smokeless tobacco]
  • The smokeless tobacco according to the present embodiment comprises the tobacco material according to the present embodiment. Examples of the smokeless tobacco according to the embodiment include heated cigarettes or E-cigarettes.
  • EXAMPLES
  • Specific examples of this embodiment will be described below, but the present invention is not limited by these examples.
  • EXAMPLE 1 (Step 1)
  • Ground leaf tobacco discarded during the tobacco production process was obtained. The average particle size (D50) of the ground product was about 0.2 to 5 mm.
  • (Step 2)
  • The ground product (500 g) was subjected solid-liquid extraction using hexane. The ground product and hexane were mixed in a weight ratio of 1:3.5 (ground product:hexane), and were soaked for 48 hours at 20°C. The solids were then filtered off to obtain an organic phase 1. The results of GC-MS analysis of the organic phase 1 are shown in Fig. 9.
  • (Step 5)
  • The organic phase 1 was subjected to liquid-liquid extraction using an aqueous solution of acid (pH 2; containing 0.1% by weight of sulfuric acid and 10% by weight of sodium chloride). The volume ratio between the organic phase 1 and the aqueous solution of acid (organic phase 1:aqueous solution of acid) was 100:100. The extraction temperature was 20°C, and the extraction time was 1 hour. Liquid-liquid extraction was performed using a separating funnel, and the aqueous phase was removed to obtain the organic phase 2.
  • (Step 6)
  • The organic phase 2 was concentrated in an evaporator (tradename: R-300 type, Nihon Buchi K.K.), and the concentrated liquid was analyzed by normal phase chromatography using n-hexane as the mobile phase. Specifically, isolation was effected under the following conditions via normal phase chromatography using silica gel (Wakosil C-300, by FUJIFILM Wako Chemicals).
    • Column: Silica gel column chromatography (approximately 60 mm x 180 mm)
    • Mobile phase: n-hexane
  • The concentrated liquid was about 10% by volume of the silica gel, and hexane was used as the mobile phase in an amount of 150% by volume of the silica gel. All of the eluent obtained as a result of the flow of the mobile phase was collected to obtain the organic phase 3 following normal chromatography. The results of GC-MS analysis of the organic phase 3 are shown in Fig. 10.
  • (Step 3)
  • The aprotic solvent (n-hexane) was distilled off from the organic phase 3 using an evaporator to obtain about 2.6 g of residue.
  • (Step 4)
  • The residue (1.0 g) was placed in a glass tube oven (tradename: GTO-1000, by Sibata Scientific Technology, Ltd.l) and was distilled at reduced pressure under conditions resulting in the volatilization of substances having a boiling point of 350 to 400°C, as determined at normal pressure. Specifically, 1.0 g of the residue was introduced into a 10 mL glass container, and distillation was effected at a reduced pressure (absolute pressure) of 30 Pa and a heating temperature of 125 to 160°C to obtain 0.06 g a fraction recovered in a glass cooling bulb 30 mm φ in diameter.
  • The resulting fraction was a clear, transparent liquid at room temperature. GC-MS analysis of the fraction (diluted with n-hexane) resulted in the chromatograms shown in Fig. 11 (fraction obtained at heating temperature of 125°C) and Fig. 12 (fraction obtained at heating temperature of 160°C). The main peak in Figs. 11 and 12 is neophytadiene (R.T. 39.27 min, m/z = 278), with a peak area ratio of 97.7% at 125 °C and 86.9% at 160. Meanwhile, the resulting residue was a white solid at room temperature. GC-MS analysis of the residue dissolved in n-hexane resulted in the chromatogram show in Fig. 13. The main peak in Fig. 13 was for C25-35 alkanes. The peak area ratio of the alkanes was 58.0%. The conditions for GC-MS analysis in the present example are shown below.
    • Oven: 40°C (3 min) → 4°C/min → 280°C (20 min)
    • Runtime: 83 min
    • Injection volume: 1 µL
    • Injection mode: Split (10:1)
    • Injection port temperature: 270°C
    • Septum purge flow rate: 5 mL/min
    • Gas saver: Off
    • Transfer line temperature: 280°C
    • Column: HP-5MS (30 m*0.25 mm*0.25 µm)
    • Column flow rate: 1 mL/min (Constant flow mode)
    • Solvent wait time: 4 min
    • Gain factor: 1
    • Measurement mode: Scan
    • Mass range: 26 to 450
    • Threshold: 50
    • Sampling rate: 2
    • MS Ion source temperature: 230°C
    • Quadrupole temperature: 150°C
  • Alkaloids such as nicotine are detected around R.T. 25 min under the above conditions of GC-MS. However, no peaks corresponding to alkaloids such as nicotine were found in the chromatograms shown in Figs. 11 through 13 at or below the quantification limit (0.005 mg/mL). The results thus showed that the method according to the present embodiment provides a tobacco extract comprising high-purity neophytadiene and a tobacco extract comprising alkanes, from which alkaloids and pigments had been adequately removed.
  • The present invention includes the following embodiments.
    1. [1] A method for producing a tobacco extract, comprising:
      • step 1 for preparing tobacco raw material
      • step 2 for subjecting the tobacco raw material to solid-liquid extraction using an aprotic solvent to remove the solids and obtain an organic phase;
      • step 3 for removing the aprotic solvent from the organic phase to obtain a residue; and
      • step 4 for distilling the residue at reduced pressure to obtain a tobacco extract comprising neophytadiene and a tobacco extract comprising alkanes.
    2. [2] The method according to [1], wherein the aprotic solvent is a water-insoluble organic solvent.
    3. [3] The method according to [2], wherein the water-insoluble organic solvent is a C5-6 hydrocarbon.
    4. [4] The method according to any of [1] through [3], further comprising step 5, between step 2 and step 3, for subjecting the organic phase to liquid-liquid extraction using water or an aqueous solution of an acid to remove the aqueous phase.
    5. [5] The method according to [4], wherein the aqueous solution of an acid is an aqueous solution of sulfuric acid, citric acid, or oxalic acid.
    6. [6] The method according to [4] or [5], wherein the pH of the aqueous solution of the acid is less than 7.
    7. [7] The method according to any of [1] through [6], further comprising step 6, between step 2 and step 3, for subjecting the organic phase obtained in step 2 or in step 5 to normal phase chromatography using n-hexane as the mobile phase.
    8. [8] A tobacco extract comprising neophytadiene or alkanes produced by the method according to any of [1] through [7].
    9. [9] The tobacco extract according to [8], wherein the tobacco extract comprising neophytadiene comprises 80% by weight or more of neophytadiene.
    10. [10] The tobacco extract according to [8], wherein the tobacco extract comprising neophytadiene comprises 90% by weight or more of neophytadiene.
    11. [11] The tobacco extract according to [8], wherein the tobacco extract comprising alkanes comprises 50% by weight or more of alkanes.
    12. [12] The tobacco extract according to [8], wherein the alkanes have 25 to 35 carbons.
    13. [13] A tobacco material comprising the tobacco extract according to any of [8] through [12].
    14. [14] The tobacco material according to [13], which is a tobacco flavoring agent, a tobacco sheet, or cut tobacco.
    15. [15] The tobacco material according to [13] or [14], comprising 3500 ppm or more of neophytadiene and 5000 ppm or more of alkanes.
    16. [16] A tobacco rod comprising the tobacco material according to any of [13] through [15].
    17. [17] A flavor inhaler comprising the tobacco rod according to [16].
    18. [18] The flavor inhaler according to [17], which is a heat-not-burn flavor inhaler or a non-burning-non-heated flavor inhaler.
    19. [19] A smokeless cigarette comprising the tobacco material according to any of [13] through [15].
    REFERENCE SIGNS LIST
  • 10
    Heating device
    11
    Body
    12
    Heater
    13
    Metal tube
    14
    Battery unit
    15
    Control unit
    16
    Recess
    17
    Ventilation holes
    20
    Heat-not-burn flavor inhaler
    20A
    Tobacco rod portion
    20B
    Cooling portion
    20C
    Filter portion
    21
    Tobacco filler
    22
    Wrapping paper
    23
    Paper tube
    24
    Perforation
    25
    First segment
    25a
    First filling layer
    25b
    Inner plug wrapper
    26
    Second segment
    26a
    Second filling layer
    26b
    Inner plug wrapper
    27
    Outer plug wrapper
    28
    Lining paper
    30
    Non-combusted/non-heated flavor inhaler
    30D
    Power source unit
    30E
    Cartridge
    30F
    Tobacco capsule
    U
    Undrawn end
    D
    Drawing end
    110
    Battery
    200
    Aerosol source
    210
    Reservoir
    220
    Atomization unit
    230
    Flow path-forming element
    240
    Outer frame 240
    250
    End cap
    200X
    First flow path
    300
    Flavor source
    310
    Housing
    320
    Mesh
    330
    Nonwoven fabric
    340
    Cap

Claims (19)

  1. A method for producing a tobacco extract, comprising:
    step 1 for preparing tobacco raw material
    step 2 for subjecting the tobacco raw material to solid-liquid extraction using an aprotic solvent to remove the solids and obtain an organic phase;
    step 3 for removing the aprotic solvent from the organic phase to obtain a residue; and
    step 4 for distilling the residue at reduced pressure to obtain a tobacco extract comprising neophytadiene and a tobacco extract comprising alkanes.
  2. The method according to Claim 1, wherein the aprotic solvent is a water-insoluble organic solvent.
  3. The method according to Claim 2, wherein the water-insoluble organic solvent is a C5-6 hydrocarbon.
  4. The method according to any of Claims 1 through 3, further comprising step 5, between step 2 and step 3, for subjecting the organic phase to liquid-liquid extraction using water or an aqueous solution of an acid to remove the aqueous phase.
  5. The method according to Claim 4, wherein the aqueous solution of an acid is an aqueous solution of sulfuric acid, citric acid, or oxalic acid.
  6. The method according to Claim 4 or 5, wherein the pH of the aqueous solution of the acid is less than 7.
  7. The method according to any of Claims 1 through 6, further comprising step 6, between step 2 and step 3, for subjecting the organic phase obtained in step 2 or in step 5 to normal phase chromatography using n-hexane as the mobile phase.
  8. A tobacco extract comprising neophytadiene or alkanes produced by the method according to any of Claims 1 through 7.
  9. The tobacco extract according to Claim 8, wherein the tobacco extract comprising neophytadiene comprises 80% by weight or more of neophytadiene.
  10. The tobacco extract according to Claim 8, wherein the tobacco extract comprising neophytadiene comprises 90% by weight or more of neophytadiene.
  11. The tobacco extract according to claim 8, wherein the tobacco extract comprising alkanes comprises 50% by weight or more of alkanes.
  12. The tobacco extract according to Claim 8, wherein the alkanes have 25 to 35 carbons.
  13. A tobacco material comprising the tobacco extract according to any of Claims 8 through 12.
  14. The tobacco material according to Claim 13, which is a tobacco flavoring agent, a tobacco sheet, or cut tobacco.
  15. The tobacco material according to Claim 13 or 14, comprising 3500 ppm or more of neophytadiene and 5000 ppm or more of alkanes.
  16. A tobacco rod comprising the tobacco material according to any of Claims 13 through 15.
  17. A flavor inhaler comprising the tobacco rod according to Claim 16.
  18. The flavor inhaler according to Claim 17, which is a heat-not-burn flavor inhaler or a non-burning-non-heated flavor inhaler.
  19. A smokeless cigarette comprising the tobacco material according to any of Claims 13 through 15.
EP23931940.3A 2023-04-04 2023-04-04 Tobacco extract and method for producing same, tobacco material, tobacco rod, flavor inhaler, and smokeless tobacco Pending EP4691272A1 (en)

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PCT/JP2023/013911 WO2024209528A1 (en) 2023-04-04 2023-04-04 Tobacco extract and method for producing same, tobacco material, tobacco rod, flavor inhaler, and smokeless tobacco

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EP2444384A1 (en) 2009-06-19 2012-04-25 Wenbo Li Use of neophytadiene as additive for liquid cigarette
WO2014104078A1 (en) 2012-12-28 2014-07-03 日本たばこ産業株式会社 Flavor source for non-combustion inhalation-type tobacco product, and non-combustion inhalation-type tobacco product
CN106501420A (en) 2016-09-30 2017-03-15 中国农业科学院烟草研究所 One grow tobacco middle neophytadiene extraction purification and detection method and its application
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CN111233611A (en) 2020-02-09 2020-06-05 昆明理工大学 A kind of separation and purification method of neophytadiene in freshly-cured tobacco leaves
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CN110041303A (en) 2019-05-30 2019-07-23 深圳波顿香料有限公司 Process for extracting neophytadiene, carotenoids and nicotine from waste tobacco leaves
CN111233611A (en) 2020-02-09 2020-06-05 昆明理工大学 A kind of separation and purification method of neophytadiene in freshly-cured tobacco leaves
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See also references of WO2024209528A1

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