EP2989907A1 - Matière première de tabac, son procédé de fabrication et produit à base de tabac - Google Patents

Matière première de tabac, son procédé de fabrication et produit à base de tabac Download PDF

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Publication number
EP2989907A1
EP2989907A1 EP14839523.9A EP14839523A EP2989907A1 EP 2989907 A1 EP2989907 A1 EP 2989907A1 EP 14839523 A EP14839523 A EP 14839523A EP 2989907 A1 EP2989907 A1 EP 2989907A1
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EP
European Patent Office
Prior art keywords
extraction
raw material
solvent
tobacco
extraction step
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
EP14839523.9A
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German (de)
English (en)
Other versions
EP2989907A4 (fr
Inventor
Naoyuki Ishida
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
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Japan Tobacco Inc
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Publication date
Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
Publication of EP2989907A1 publication Critical patent/EP2989907A1/fr
Publication of EP2989907A4 publication Critical patent/EP2989907A4/fr
Pending legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—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
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific substances

Definitions

  • Known methods for adjusting the smoking flavor of tobacco include art in which specific components are extracted and removed from a leaf tobacco material, and art that entails carrying out an extraction operation on a leaf tobacco material so as to obtain an extract and an extraction residue, carrying out a given treatment, etc. on the extract, then re-applying the treated extract to the extraction residue.
  • a known technique for extracting and removing specific components from a leaf tobacco material involves removing lipid components from tobacco using a mixed solvent of an aliphatic hydrocarbon and a lower alcohol (Patent Document 1).
  • the group of bipolar components is also removed. This sometimes has a large influence on the smoking flavor of the tobacco raw material.
  • the group of components obtained by a single extraction includes numerous components.
  • the extract has been treated (such as by contact with an antioxidant), in addition to the components to be removed, the components which affect the smoking flavor are also thought to change. Hence, there seems to be a possibility of a large influence on the smoking flavor.
  • a method of production that includes: a first extraction step of extracting a leaf tobacco material using a solvent having a dielectric constant of 1 or more and less than 25 to obtain an extract and an extraction residue; a second extraction step of, following the first extraction step, extracting the extraction residue obtained in the first extraction step with a solvent having a dielectric constant of 25 or more to obtain an extraction residue; and the step of re-applying the extract obtained in the first extraction step to the extraction residue obtained in the second extraction step so as to form a leaf tobacco raw material.
  • leaf tobacco material refers to a material used to produce “tobacco raw material”, and means leaf tobacco prior to passing through treatment such as extraction steps.
  • tobacco raw material refers to the product obtained by applying treatment such as extraction steps to the "leaf tobacco material”.
  • the leaf tobacco material that may be used in this invention is not particularly limited as to type.
  • Illustrative examples include genus Nicotiana varieties such as flue-cured and burley varieties of nicotiana tabacum, and the brasilia variety of nicotiana rustica.
  • solvents having a dielectric constant of 1 or more and less than 25 include ethanol, isopropyl alcohol, ethyl acetate, linear or branched alkanes of 5 to 10 carbons, n-propyl alcohol, butanol, benzene, toluene, xylene, benzyl alcohol, acetone, tetrahydrofuran, diethyl ether, 1,4-dioxane, chloroform and dichloromethane.
  • alkanes examples include pentane, n-hexane, cyclohexane, heptane, octane, nonane and decane.
  • Extraction may be carried out at normal temperature and pressure, or may be carried out with warming to, for example, about 40 to 80°C and under an applied pressure of from 1,000 to 2,000 psi.
  • calculation is carried out at a conversion factor of 1 psi ⁇ 6,894.757 Pa.
  • Extraction may be carried out once or may be carried out a plurality of times. Extraction may be carried out using the subsequently described accelerated solvent extraction system.
  • the resulting extraction residue is dried by a suitable method.
  • the drying method is exemplified by freeze-drying.
  • an extraction operation using a solvent having a dielectric constant of 25 or more By additionally carrying out, on the extraction residue obtained via the first extraction step, an extraction operation using a solvent having a dielectric constant of 25 or more, components within the leaf tobacco material that were not extracted in the first extraction step can be extracted.
  • the solvent having a dielectric constant of 25 or more that is used in the second extraction step is not particularly limited.
  • Illustrative examples include water, methanol, and mixed solvents containing these.
  • the second extraction step may be carried out at normal temperature and pressure as the extraction conditions. Extraction may also be carried out with warming to about 40 to 80°C and under an applied pressure of 1,000 to 2000 psi.
  • the extraction time is not particularly limited, and may be set to from 5 minutes to 1 hour.
  • the solvent used in the second extraction step has a higher dielectric constant than the solvent used in the first extraction step, components within the leaf tobacco material that were not extracted in the first extraction step can be extracted in the second extraction step.
  • the extract obtained in the second extraction step is not re-applied to the extraction residue.
  • unwanted components contained in the leaf tobacco material can be removed from the extraction residue obtained in the first extraction step.
  • unwanted components include high-polarity components, such as low-molecular-weight organic acids and ammonia.
  • the order of the first extraction step and the second extraction is important. That is, it is important to use a relatively low-polarity solvent as the solvent in the initial extraction step, and to use a relatively high-polarity solvent having a higher dielectric constant than the solvent used in the first extraction step as the solvent in the next extraction step. If this order is reversed, a tobacco raw material having a good smoking flavor cannot be obtained.
  • the production method of the invention includes the step of, after passing through the second extraction step, re-applying the extract obtained in the first extraction step to the extraction residue obtained by passing through the second extraction step so as to form a leaf tobacco raw material.
  • this step by re-applying the extract obtained in the first extraction step to the extraction residue obtained in the second extraction step, components that were extracted in the first extraction step and are desirable for the smoking flavor of the tobacco raw material are returned to the tobacco raw material.
  • the extract obtained in the first extraction step may be re-applied directly as is, or may be re-applied after concentrating the solvent only.
  • the extract may be subjected to salting-out treatment.
  • the solvent is removed by a suitable method.
  • the mode of use of the tobacco raw material obtained by the production method of the invention is exemplified by use at normal temperature and use in a warmed state, and the smoking flavor when used in either of these ways is excellent.
  • Modes of use at normal temperature or under heated conditions are exemplified by use in which leaf tobacco obtained by the above treatment is filled into, for example, a tube having a bore of 0.7 mm and used.
  • Modes of use in a warmed state are exemplified by use in which the leaf tobacco is warmed to, for example, about 40 to 70°C.
  • the tobacco raw material of the invention has a ratio, which is expressed as "water-extracted material weight/hexane-extracted material weight" (or “W/H ratio”), between the weight of an extracted material obtained by extraction using n-hexane as a solvent (also referred to below as “hexane-extracted material”) and the weight of an extracted material obtained by extraction using water as a solvent (also referred to below as “water-extracted material”), of 0 or more and 1.5 or less.
  • This tobacco raw material by having such a W/H ratio, is a tobacco raw material with a good smoking flavor.
  • a W/H ratio greater than 1.5 i.e., at a content of water-extracted material that is too large, the tobacco raw material has a smoking flavor that is adulterated.
  • the W/H ratio may have a value of 0.3 or more and 0.6 or less.
  • the sum of the weight of the hexane-extracted material and the water-extracted material in the tobacco raw material of the invention may be from 5 to 17 wt %, based on the weight of the tobacco raw material prior to extraction. In another embodiment, this may be from 5 to 14 wt %.
  • Production of tobacco raw material having such a W/H ratio may involve the use of, for example, the above-described tobacco raw material production method of the invention.
  • the following method may be used as the method of measuring, within the tobacco raw material, the amount of extracted material that can be obtained by extraction using n-hexane as the solvent and the amount of extracted material that can be obtained by subsequent extraction using water as the solvent.
  • an accelerated solvent extraction system (ASE 200, from Dionex) is used and a sample-filled cell is prepared by placing 1.0 g/cell of tobacco raw material in a pressure-resistant extraction cell made of metal and having a volume of 22 mL. The cell is mounted in the accelerated solvent extraction system, and extraction is carried out under the conditions shown in the table below.
  • the extract is transferred to a specialized glass vial for the solvent extraction system, this extract being collected following extraction and used to measure the amount of extraction (see below for the method).
  • a single cycle in solvent extraction consists of pressurized filling of the solvent, warming, standing at rest, purging (transfer of solvent to the vial) and, once again, pressurized filling of the solvent.
  • n-hexane three cycles are repeated and the total amount of liquid obtained from one cell is collected in one vial.
  • water extraction is successively carried out, a total of nine cycles are repeated and the total amount of liquid obtained from three cycles is collected in one vial. Hence, a total of three vials can be obtained from one cell.
  • Measurement of the amount of n-hexane extraction is carried out as follows.
  • a 1 vial/1 cell n-hexane extract is transferred to a pre-weighed 100 mL round-bottomed flask using n-hexane, ethyl acetate and ethanol, in addition to which the vial is rinsed out, thereby collecting all of the extracted material in the flask.
  • the round-bottomed flask is placed on a rotary evaporator and the contents are vacuum-concentrated, then dried at normal temperature and reduced pressure for 3 hours with a vacuum oil pump. Concentration is carried out using a rotary evaporator equipped with trapping balls, and the liquid temperature of the water tank is set to 25°C or less. The weight of the flask after drying is measured, and the difference is treated as the amount of n-hexane extracted material.
  • a 3 vial/1 cell water extract is transferred, using ultrapure water, to a pre-weighed 500 mL interchangeable ground joint round-bottomed flask for freezing, in addition to which the vial is rinsed out so that all of the extracted material is recovered in the flask.
  • the round-bottomed flask and its contents are frozen in the pre-freezing tank of a freeze-drying system and then connected to the freeze-drying system and dried. The weight of the flask after drying is measured, and the difference is treated as the yield of water-extracted material.
  • Leaf tobacco material (a domestically produced burley variety) was ground using a grinding mill.
  • the grinding mill used was an SK-M10 Sample Mill from Kyoritsu Riko K.K.
  • the ground material was then immediately applied to a sieve, giving a ground leaf tobacco material having a particle size of from 0.425 mm to 1.18 mm.
  • 2 g of this ground leaf tobacco material was precisely weighed and filled into a metal cell.
  • the voids that formed during filling were filled using stainless steel beads.
  • the cell used was a 22 mL extraction cell made by Dionex, and the beads were 2.2 mm diameter beads from Central Scientific Commerce, Inc. Solvent was delivered to this cell, and an accelerated solvent extraction system was used to carry out extraction on the ground leaf tobacco material.
  • the extractor used was an ASE-200 accelerated solvent extraction system from Dionex.
  • the volume of extract obtained with these solvents was about 40 mL.
  • the extract was concentrated using an evaporator and, using the same solvent as that used during extraction, was brought to a constant volume of 6.25 mL in a suspended state. Extraction with water (dielectric constant, 80) as the solvent was then carried out. At the time of this extraction, the same sequence was followed as for extraction with a solvent having a dielectric constant of 1 or more and less than 25, but the temperature during warming and the pressure during standing at rest were set to 100°C and 2,000 psi. Also, the three cycles carried out during extraction with a solvent having a dielectric constant of 1 or more and less than 25 was changed to nine cycles during extraction with water. The total volume of the extract was about 120 mL.
  • the ammonia contents were measured for the tobacco raw materials in Examples 1 and 2 and Comparative Example 1. Measurement of the ammonia content in the tobacco raw material was carried out by the following procedure.
  • Untreated raw material 180 mg or treated raw material (having the weight obtained when 180 mg of untreated raw material has been treated) was immersed and extracted for 30 minutes in 5 mL of pure water. The extract was then filtered with a 10 KDa ultrafiltration membrane. The filtrate was analyzed with a capillary electrophoresis chromatograph (Agilent Technologies). The absorbance was measured at a wavelength of 280 nm and the ammonia was quantitatively determined as ammonium ions using an aqueous solution of ammonium chloride diluted to a suitable concentration as the standard solution.
  • Example 3 With regard to tobacco raw material obtained by the production method of the invention, sensory evaluations of the sort described below were carried out in Example 3, where the tobacco raw material was produced under the same conditions as in Example 1; in Comparative Example 2, where it was obtained by carrying out only the operation of re-applying the extract obtained from the first extraction step (no second extraction step); in Example 4 where it was obtained by, aside from using a Brazilian flue-cured variety as the leaf tobacco material, carrying out the same operations as in Example 1; in Comparative Example 3, where it was obtained by carrying out only the operation of re-applying the extract obtained from the first extraction step in Example 4 (no second extraction step); in Example 5, where it was obtained from the same leaf tobacco material and operations as in Example 3; and in Comparative Example 4, where it was obtained from the same leaf tobacco material and operations as in Comparative Example 2. The following operations were carried out during sensory evaluation.
  • Untreated material that had been ground and sieved (particle size, from 0.425 mm to 1.18 mm) and the respective tobacco raw materials (Examples 3 and 4, and Comparative Examples 2 and 3) were filled into quartz tubes (9 mm (o.d.) x 7 mm (i.d.) x 55 mm (L)).
  • the fill weight was set to 180 mg for untreated raw material and in cases where no extracted material was removed.
  • the fill weight was set to 109 mg (the weight of the raw material obtained when 180 mg of raw material was treated).
  • the sample was kept from scattering upon inhalation during evaluation by stopping both ends of the quartz tube with stainless steel mesh. These quartz tubes were heated to 60°C, inhalation was carried out from one end of the tube, and the results compared with untreated raw material were examined.
  • the sensory evaluation (change in smoking satisfaction) criteria are shown below.
  • the degree of change relative to untreated raw material was rated using the 7-step scale expressed in terms of the language shown below.
  • the number of subjects for each evaluation was set at ten people.
  • the least significant difference (LSD) was used to determine the significance of differences in the sensory evaluation results due to the treatment method. The results are shown in FIGS. 1 and 2 .
  • the tobacco raw material obtained by the production method of the invention was found to achieve an excellent smoking flavor.
  • Untreated material that had been ground and sieved (particle size, from 0.425 mm to 1.18 mm) and the respective tobacco raw materials (Example 5 and Comparative Example 4) were filled into plastic tubes (9 mm (o.d.) x 7 mm (i.d.) x 110 mm (L)).
  • the fill weight was set to 360 mg for untreated raw material and in cases where no extracted material was removed.
  • the fill weight was set to 218 mg (the weight of the raw material obtained when 360 mg of raw material was treated).
  • the sample was kept from scattering upon inhalation during evaluation by stopping both ends of the plastic tube with nonwoven fabric mesh. Using these plastic tubes, inhalation was carried out from one end of the tube at room temperature, and the results in compared with untreated raw material were examined. The results are shown in FIG. 3 .
  • Example 5 and Comparative Example 4 were carried out in the same way as for Examples 3 and 4 and Comparative Examples 2 and 3. As a result, in tests by the least significant difference method, there was a 95% significant difference between Example 5 and Comparative Example 4. Hence, effects due to the production method of the invention were observed.
  • Example 6 The tobacco raw material of Example 6 (104.94 mg) and the tobacco raw material produced in Comparative Example 1 (using methanol as the solvent for extraction in the first extraction step; 134.55 mg) were subjected to sensory evaluations (change in smoking satisfaction) by the same method as in Examples 3 and 4 and Comparative Examples 2 and 3. The results are shown in FIG. 4 .
  • Leaf tobacco material of a domestic burley variety was subjected to grinding treatment in the same way as in Example 1, and the first extraction step was not carried out; only the second extraction step was carried out (only extraction with water was carried out). The extract obtained by this second extraction step was re-applied to the extraction residue, thereby producing a tobacco raw material for Comparative Example 5.
  • leaf tobacco material of a domestic burley variety was subjected to grinding treatment in the same way as in Example 1 and the second extraction step (extraction with water) was initially carried out, following which the first extraction step (extraction with n-hexane) was carried out. Next, only the extract obtained by carrying out extraction with water was re-applied to the extraction residue, thereby producing a tobacco raw material for Comparative Example 6.
  • Leaf tobacco material of a domestic burley variety was subjected to grinding treatment in the same way as in Example 1, the second extraction step was carried out first (i.e., extraction with water was carried out first), following which the first extraction step was carried out (i.e., extraction with n-hexane was subsequently carried out), and the extract thus obtained (n-hexane extract only) was re-applied to the extraction residue, thereby producing a tobacco raw material for Comparative Example 7.
  • Example 1 The W/H ratios of the respective tobacco raw materials obtained in Example 1 (in which n-hexane was used in the first extraction step), Example 2 (in which ethanol was used in the first extraction step), Example 6 (in which tetrahydrofuran was used in the first extraction step), and Comparative Example 1 (in which methanol was used in the first extraction step) were measured.
  • Example 2 In which ethanol was used in the first extraction step
  • Example 6 in which tetrahydrofuran was used in the first extraction step
  • Comparative Example 1 in which methanol was used in the first extraction step
  • Additive-free filter paper was set in a pressure-resistant metal extraction cell, and the cell was filled with 10 g of prewashed and weighed stainless steel balls.
  • the tobacco raw materials obtained in Examples 1, 2 and 6, Comparative Example 1 and the reference example were weighed out, with an even balance, in respective amounts of 1.0 g/cell onto powder paper and, using a suitable aid such as a powder funnel, the weighed samples were placed in the already prepared 22 mL cells in which the filter paper and stainless steel balls had been set; sample remaining on the powder paper was wiped several times with the stainless steel balls and added to the cell.
  • voids were eliminated by packing the cell with stainless steel balls until it was filled to the top. Once the cell was completely filled, the top side was closed and the cell was tapped on a desk to bury any gaps and even out the contents, after which the empty space was filled with stainless steel balls.
  • Freeze dryer with pre-freezer (FD-81, from Tokyo Rikakikai Co., Ltd.)
  • Vacuum oil pump (ULVAC GCD-051X, from ULVAC KIKO Inc.)
  • Ethanol high-performance liquid chromatography (HPLC) grade, from Wako Pure Chemical Industries, Ltd.
  • HPLC high-performance liquid chromatography
  • Powder paper 10 cm square sheets
  • Interchangeable ground joint round-bottom flasks for freeze-drying 500 mL (EYELA K.K.)

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
EP14839523.9A 2013-08-27 2014-08-26 Matière première de tabac, son procédé de fabrication et produit à base de tabac Pending EP2989907A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013175626 2013-08-27
PCT/JP2014/072244 WO2015029977A1 (fr) 2013-08-27 2014-08-26 Matière première de tabac, son procédé de fabrication et produit à base de tabac

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EP2989907A1 true EP2989907A1 (fr) 2016-03-02
EP2989907A4 EP2989907A4 (fr) 2017-01-11

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US (1) US20160100626A1 (fr)
EP (1) EP2989907A4 (fr)
JP (1) JP6109319B2 (fr)
CN (1) CN105451580B (fr)
TW (1) TW201511695A (fr)
WO (1) WO2015029977A1 (fr)

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CN106509979A (zh) * 2016-12-26 2017-03-22 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法
CN106617257A (zh) * 2016-12-26 2017-05-10 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法

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CN106509972B (zh) * 2016-11-25 2018-08-03 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法
CN106723312B (zh) * 2016-12-26 2018-08-10 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法
CN106723316B (zh) * 2016-12-26 2018-06-22 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法
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CN111511224B (zh) * 2017-12-27 2022-04-19 日本烟草产业株式会社 烟草提取物、烟草提取物的制造方法、以及使用了烟草提取物的非燃烧型香味抽吸器
JPWO2022137745A1 (fr) 2020-12-21 2022-06-30
CN113951549A (zh) * 2021-11-09 2022-01-21 云南中烟工业有限责任公司 一种低烟碱烟丝的制备方法
CN113951550A (zh) * 2021-11-09 2022-01-21 云南中烟工业有限责任公司 一种高香气低烟碱烟丝的制备方法
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CN106509979A (zh) * 2016-12-26 2017-03-22 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法
CN106617257A (zh) * 2016-12-26 2017-05-10 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法
CN106617257B (zh) * 2016-12-26 2018-06-22 福建中烟工业有限责任公司 一种组合物及使用该组合物制备烟草提取物的方法

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JPWO2015029977A1 (ja) 2017-03-02
US20160100626A1 (en) 2016-04-14
JP6109319B2 (ja) 2017-04-05
WO2015029977A1 (fr) 2015-03-05
CN105451580A (zh) 2016-03-30
EP2989907A4 (fr) 2017-01-11
TW201511695A (zh) 2015-04-01
CN105451580B (zh) 2019-03-08

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