Classifications

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

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Citations (6)

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• 2023
  • 2023-04-04 WO PCT/JP2023/013911 patent/WO2024209528A1/ja not_active Ceased
  • 2023-04-04 EP EP23931940.3A patent/EP4691272A1/en active Pending
  • 2023-04-04 JP JP2025512234A patent/JPWO2024209528A1/ja active Pending

Patent Citations (7)

Non-Patent Citations (3)

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