EP3315031A1 - Zusammensetzung - Google Patents

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Publication number
EP3315031A1
EP3315031A1 EP16830215.6A EP16830215A EP3315031A1 EP 3315031 A1 EP3315031 A1 EP 3315031A1 EP 16830215 A EP16830215 A EP 16830215A EP 3315031 A1 EP3315031 A1 EP 3315031A1
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EP
European Patent Office
Prior art keywords
tobacco
catalyst
composition
ethyl
esterification reaction
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.)
Withdrawn
Application number
EP16830215.6A
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English (en)
French (fr)
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EP3315031A4 (de
Inventor
Megumi KATSUOKA
Takahisa KATSUOKA
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Japan Tobacco Inc
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Japan Tobacco Inc
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Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
Publication of EP3315031A1 publication Critical patent/EP3315031A1/de
Publication of EP3315031A4 publication Critical patent/EP3315031A4/de
Withdrawn legal-status Critical Current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
    • A24B15/28—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
    • A24B15/302—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants
    • 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 composition, and more specifically, for example, a composition for a tobacco product.
  • Patent Document 1 a technique in which some of tobacco components are esterified and treated with nitrous acid
  • Patent Document 2 a method in which shredded tobacco is cured in an air atmosphere under sealed conditions in order to enhance ester flavour components or components contributing to smoke flavour
  • Non-Patent Document 1 Shimizu and Takei, Journal of the agricultural chemical society of Japan, 23, 286 (1949 )
  • Patent Document 1 requires several steps, rendering the process complicated.
  • components in tobacco subjected to esterification reaction are those fractioned in a hexane phase, and thus the amount and type of esters produced are limited.
  • reaction (curing) requires a long period of time (1 week to 3 months).
  • both techniques disclosed in Patent Document 1 and 2 focus on the change in smoke flavour of mainstream smoke and do not seek to reduce smell of sidestream smoke. Further, the amount and type of esters produced are limited, and thus it is hard to say that smell of sidestream smoke is efficiently reduced by the above manners. In both techniques disclosed in Patent Document 1 and 2, it is studied how to make changes in flavour of tobacco per se through treatment of tobacco leaves without addition of fragrances, meaning that the studies focus on the changes in smoke flavour of mainstream smoke and do not seek reducing the smell of sidestream smoke.
  • an object of the present invention is to provide a composition that can efficiently reduce the smell of sidestream smoke when added to tobacco leaves; a tobacco material including the composition and tobacco leaves; and a method for producing the foregoing.
  • the above object can be achieved by the composition containing diethyl malate and one or more from ethyl levulinate, ethyl palmitate and triethyl citrate, reaching to the present invention.
  • composition of the present invention When the composition of the present invention is added to tobacco leaves, or when a tobacco material including the composition and tobacco leaves is used, the smell of sidestream smoke can be efficiently reduced.
  • composition of the present invention contains diethyl malate and one or more selected from ethyl levulinate, ethyl palmitate and triethyl citrate.
  • the composition of the present invention contains not only diethyl malate but also one or more selected from ethyl levulinate, ethyl palmitate and triethyl citrate in combination with diethyl malate.
  • the effect of reducing tobacco smell is increased when the composition is added to tobacco leaves or when a tobacco material containing the composition and tobacco leaves is used.
  • composition of the present invention containing diethyl malate and one or more selected from ethyl levulinate, ethyl palmitate and triethyl citrate may be prepared by mixing the isolated compounds or, as in the method for producing the composition of the present invention described hereinafter, may be prepared by isolating and purifying malic acid, levulinic acid, palmitic acid and citric acid from a treatment liquid obtained through the step of allowing reaction of malic acid, levulinic acid, palmitic acid and citric acid in tobacco leaves with ethanol and carrying out esterification.
  • the method for isolation and purification in this context may be carried out with well-known chromatography including, for example, ion-exchange chromatography and reverse phase high performance liquid chromatography.
  • the conditions for the chromatography may be those well-known.
  • composition of the present invention is preferably for a tobacco product.
  • the term "for a tobacco product” means that the composition may be added to tobacco leaves for preparation of a tobacco product or may be used as a tobacco material for production of a tobacco product.
  • the composition of the present invention contains diethyl malate at preferably 5% by weight or more, more preferably 10% by weight or more and still more preferably 20% by weight or more relative to the total content of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate in the composition.
  • the content of diethyl malate is preferably 95% by weight or less, more preferably 80% by weight or less, still more preferably 60% by weight or less relative to the total content of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate.
  • the total content of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate relative to the total amount of the composition of the present invention may be 5% to 95% by weight in an embodiment, 10% to 80% by weight in a preferable embodiment and 20% to 60% by weight in a more preferable embodiment.
  • each of ethyl levulinate, ethyl palmitate and triethyl citrate in the composition of the present invention is not particularly limited as far as the content is in the range that does not impair the effect of the present invention: however, as an example, the weight proportion thereof may fulfil the relationship of ethyl levulinate > ethyl palmitate > triethyl citrate in an embodiment.
  • the ethyl esters may be combined respectively with diethyl malate or more than one ethyl ester may be combined with diethyl malate.
  • Ethyl palmitate is preferably combined with diethyl malate.
  • One or both of ethyl levulinate and triethyl citrate may be combined with the above combination.
  • the total amount of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate in the composition may be 0.01% by weight or more, preferably 0.05% by weight or more and more preferably 0.1% by weight or more relative to the material wet weight of tobacco leaves in an embodiment. Meanwhile, in this context, the total amount of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate in the composition may be 10% by weight or less relative to the material wet weight of tobacco leaves in an embodiment.
  • the total amount of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate may be 0.01% by weight or more, preferably 0.05% by weight or more, more preferably 0.1% by weight or more relative to the material wet weight of tobacco leaves in the tobacco material in an embodiment.
  • the total amount of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate may be 10% by weight or less in an embodiment.
  • isolated ethyl ester compounds When the composition of the present invention is added to tobacco leaves, isolated ethyl ester compounds may be mixed to obtain the composition.
  • Isolated diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate may be ones commercially available or may be obtained by fractionation of synthesised ethyl esters so as to adjust the concentrations thereof.
  • the composition may be prepared by obtaining a solution containing malic acid, levulinic acid, palmitic acid, citric acid and carbohydrates (precursors of levulinic acid) from tobacco leaves by extraction treatment of the tobacco leaves, and isolating and purifying a treatment liquid containing ethyl esters obtained by mixing the obtained liquid extract with a solution containing ethanol and carrying out esterification.
  • the method for isolation and purification in this context may be carried out by well-known distillation under reduced pressure or chromatography including, for example, adsorption chromatography using a rotary evaporator or silica gel.
  • the conditions for the isolation and purification may be those well-known.
  • Tobacco leaves used may be those described hereinafter as well as those without shredding, tobacco leaves shredded into predetermined shapes, tobacco powder having a predetermined size or lamina without shredding.
  • Tobacco leaves to be subjected to extraction may contain water.
  • a specific method for preparing the composition when the ethyl ester compounds are obtained by reactions may include the following procedures.
  • the solvent used for extraction may be water or ethanol alone or a mixture thereof.
  • the solvent used for extraction is water or a mixture of water and ethanol
  • the amount of compounds extracted and to be subjected to esterification reaction may be increased.
  • water may be an inhibitor of esterification reaction. Therefore, it is desirable to adjust the amount of water in the reaction solution by concentrating the liquid extract to obtain a concentrate to which ethanol is then added or adding ethanol to the liquid extract so that the water concentration is sufficiently low.
  • Well-known concentration methods may be used.
  • the conditions during extraction such as temperature and time may be the same conditions as extraction using an extraction solvent containing ethanol as a main component.
  • the liquid extract When the extraction solvent is ethanol, the liquid extract may be directly subjected to the following reaction, or when the extraction solvent is a mixed solvent of ethanol with water or the extraction solvent contains water, the liquid extract after reduction of the amount of water in the system to such an extent that at least the reaction proceeds may be subjected to the following reaction.
  • a manner for reduction of the amount of water may include concentration of the liquid extract.
  • the amount of water in this context may be less than 90% by weight, preferably less than 50% by weight, more preferably less than 10% by weight in the solution for esterification reaction in an embodiment.
  • the extraction solvent is ethanol, it is not required to add a step of removing water from the liquid extract.
  • the obtained liquid extract is concentrated and esterification reaction is carried out with a catalyst under conditions such that the pressure is at or lower than a predetermined value. Therefore, it is preferable to carry out the reaction in a pressure resistance vessel or the like.
  • the catalyst that can be used is described hereinafter.
  • the pressure during the reaction may be normal pressure to 1 MPa.
  • the reaction time may be 5 to 500 minutes, preferably 10 to 300 minutes and more preferably 10 to 180 minutes.
  • the temperature during the reaction may be 60°C to 150°C, preferably 80°C to 120°C and more preferably 100°C to 120°C. In order to ensure such a temperature, it is preferable to carry out the reaction under heating.
  • the amount of the catalyst used may be, when a solid acid is used, 5% to 400% by weight, preferably 10% to 300% by weight and more preferably 20% to 200% by weight relative to the wet weight of tobacco leaves.
  • the amount may be 0.001% to 10% by weight, preferably 0.01% to 8% by weight and more preferably 0.1% to 5% by weight relative to the wet weight of tobacco leaves.
  • the esterification reaction may be carried out while the reaction solution contains the catalyst or the catalyst may be, when the catalyst is a solid acid, removed from the reaction solution prior to esterification reaction.
  • esterification reaction proceeds by bringing the catalyst into contact with the reaction solution thereby allowing proton exchange. Specifically, when the reaction is heated, esterification reaction proceeds even when the solid acid does not exist in the solution.
  • the solution obtained after esterification reaction of the liquid extract contains diethyl malate and one or more selected from ethyl levulinate, ethyl palmitate and triethyl citrate, and the solution directly or after removal of unnecessary substances such as the catalyst may serve as a treatment liquid containing the composition of the present invention.
  • the treatment liquid containing the composition of the present invention obtained through the above process may be added back to the extraction residue of the tobacco leaves.
  • the treatment liquid is added to another tobacco product such as shredded tobacco, the treatment liquid is subjected to isolation and purification to prepare the composition which is then added to a material of the tobacco product.
  • the conditions for the separation and purification in this context may be well-known distillation under reduced pressure or chromatography.
  • a method for producing a tobacco material containing tobacco leaves and the composition containing the ethyl ester compounds obtained by reacting ethanol with malic acid and one or more selected from levulinic acid, palmitic acid and citric acid contained in tobacco leaves without extraction may be a method in which a catalyst and ethanol are added to tobacco leaves to allow ethyl esterification reaction.
  • a tobacco material may be prepared which contains tobacco leaves and a composition containing diethyl malate and one or more selected from ethyl levulinate, ethyl palmitate and triethyl citrate.
  • the obtained tobacco material containing the composition and tobacco leaves may be directly used.
  • the tobacco material containing the composition and tobacco leaves prepared according to the above method may be mixed with a material for tobacco product such as another tobacco leaves.
  • the conditions for the esterification in this context may be the same conditions as esterification of the above liquid extract.
  • the catalyst used for synthesis of the ethyl ester compounds may be a liquid acid or a solid acid.
  • the liquid acid preferably has an acid dissociation constant of 6 or less and more preferably less than 3.
  • liquid acid examples include sulphuric acid, sulphurous acid, hydrochloric acid, hypochlorous acid, benzoic acid, formic acid, citric acid, malic acid, tartaric acid, valeric acid, isovaleric acid, butyric acid, malonic acid, glutamic acid, succinic acid, lactic acid, acetic acid, salicylic acid, oxalic acid, phosphoric acid and the like.
  • solid acid examples include natural mineral, cation-exchange resins, immobilised acids, metal oxides, composite metal oxides, calcinated metal sulphates and the like.
  • a specific example of the solid acid preferably has a desorption ammonia amount of 10 ⁇ mol/g or more at a desorption peak in the temperature range of less than 500°C as measured by an ammonia TPD method described hereinafter.
  • the solid acid that can be used in the production method of the present invention more preferably has an ammonia desorption amount of 500 ⁇ mol/g or more at a desorption peak in the temperature range of less than 400°C as measured by the ammonia TPD method.
  • Examples of the solid acid having the above characteristic include organic substances such as resins having acidic exchange groups (such as styrene resins) and inorganic carriers such as silica gel carrying acidic functional groups.
  • Examples of the acidic exchange groups and acidic functional groups include a sulphonate group.
  • the solid acid is pretreated to remove water adsorbed thereon, ammonia is adsorbed thereon and then desorbed by increasing temperature.
  • the desorption amount is plotted relative to the temperature during desorption by temperature increase, the acid amount and the acid strength can be estimated from the extent of the desorption amount and the desorption temperature, respectively.
  • embodiments of methods for producing the composition of the present invention and a tobacco material containing the composition and tobacco leaves may be (A) to (C) below.
  • the conditions for extraction and esterification reaction are described above.
  • a liquid extract is obtained from tobacco leaves with ethanol as an extraction solvent and the catalyst is added to the liquid extract to carry out esterification reaction.
  • a liquid extract is obtained from tobacco leaves with water or water and ethanol as an extraction solvent; the liquid extract is concentrated to obtain a concentrate to which ethanol is added (the step (1)) or ethanol is added to the liquid extract without concentration (the step (2)); and the catalyst is added to the solution or concentrate obtained in either of the steps to carry out esterification reaction.
  • the catalyst may be removed from the solution by filtration or the like operation prior to the esterification reaction because, as described above, as far as proton exchange is carried out by once bringing the reaction solution into contact with the solid acid, the reaction proceeds even when the catalyst does not exist in the reaction solution.
  • the catalyst may be reused.
  • Tobacco leaves which may be used for preparation of the composition of the present invention or a tobacco material containing the composition may include shredded tobacco (hereinafter also referred to as shredded leaf tobacco) used for cigarettes.
  • shredded tobacco hereinafter also referred to as shredded leaf tobacco
  • the shredded tobacco may be of any variety.
  • stemmed tobacco leaves and stems of Flue-Cured tobacco, Burley and Oriental, and a regenerated sheet formed with the above material may be used.
  • Shredded tobacco generally means one that is ready to be used for production of a tobacco product.
  • Shredded tobacco may have any well-known size of shredded leaf pieces without limitation.
  • tobacco leaves used for extraction of malic acid, levulinic acid, palmitic acid and citric acid may also be the same as above.
  • shredded tobacco in the cigarette may have any well-known size of leaves.
  • the configuration of the cigarette as a tobacco product is not particularly limited and may have any well-known aspects.
  • composition of the present invention may contain other additives in the range that does not impair the effect of the present invention.
  • examples of such an additive include a fragrance and a humectant.
  • the composition of the present invention may be added to tobacco leaves for preparation of a tobacco product or a tobacco material including the composition and tobacco leaves may be directly used.
  • the tobacco product may preferably be a smoking article. Namely, it is preferable that the composition of the present invention, and the tobacco material including the composition and tobacco leaves, are used for a smoking article among tobacco products, respectively.
  • composition of the present invention and the tobacco material including the composition and tobacco leaves, may also be used for an oral tobacco product or an electronic tobacco, respectively.
  • Examples of the smoking article include cigarettes, cigars and cigarillos.
  • composition of the present invention When the composition of the present invention is added to tobacco leaves for production of a tobacco product, the composition of the present invention is added to tobacco leaves for preparation of the tobacco product.
  • the tobacco leaves used for the tobacco product are used during preparation of the composition for the tobacco material.
  • the tobacco material including the composition of the present invention and tobacco leaves may be directly used as an ingredient for the tobacco product.
  • the ingredient derived from tobacco leaves such as shredded tobacco in the composition may be 80% to 99.99% by weight relative to the total amount of the composition in terms of the dry weight in an embodiment.
  • the amount of the composition added is not particularly limited.
  • the composition may be added so that diethyl malate is 5% to 95% by weight relative to the total weight of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate in the ingredient for a tobacco product formed with tobacco leaves to which the composition has been added.
  • the content of diethyl malate is 20% to 60% by weight relative to the total weight of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate.
  • composition of the present invention When the composition of the present invention is added to tobacco leaves at the amount described above, the effect of reducing the smell of sidestream smoke may be preferably obtained.
  • composition of the present invention so that the content of diethyl malate is 0.0005% to 1% by weight relative to the wet weight of the ingredient for a tobacco product formed with tobacco leaves to which the composition has been added.
  • diethyl malate is 5% to 95% by weight relative to the total weight of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate in the tobacco material in an embodiment.
  • the content of diethyl malate is 20% to 60% by weight relative to the total weight of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate.
  • the content of diethyl malate is 0.0005% to 1% by weight relative to the wet weight of tobacco leaves.
  • the composition of the present invention or the tobacco material contains diethyl malate at the above content, the effect of reducing the smell of sidestream smoke may be preferably obtained.
  • the amount of diethyl malate is preferably 5% to 95% by weight and more preferably 20% to 60% by weight relative to the total amount of diethyl malate, ethyl levulinate, ethyl palmitate and triethyl citrate in the composition of the present invention or the tobacco material.
  • a liquid acid such as sulphuric acid or a solid acid which is a resin carrying an acidic functional group
  • a solid acid which can be easily separated is useful. Therefore, the solid acid was used for synthesis of ethyl ester compounds from an ethanol liquid extract of tobacco leaves.
  • Ethanol was added to shredded Japanese Flue-Cured tobacco at a solid-liquid ratio of 1 g-wet tobacco : 10 ml, extraction was carried out while shaking in a water bath at 60°C for 1 hour and the liquid extract was separated from the extraction residue using a non-woven fabric. After concentrating the liquid extract to a predetermined concentration, the liquid extract was heated in a pressure resistance vessel together with a catalyst at 120°C for 1 hour. Five different catalysts indicated in Table 2 were used. The catalysts purchased were used without pretreatment and the amount added was 50% by weight relative to the wet weight of tobacco.
  • Table 2 Catalysts used No. Catalyst Functional group Carrier Specific surface area* (m 2 /g-dry) Average pore diameter* (nm) 1 Commercial product solid acid a -SO 3 H Styrene resin 45 24 2 Commercial product solid acid b -SO 3 H Styrene resin - - 3 Commercial product solid acid c -SO 3 H Silica gel 440 6 4 Commercial product solid acid d -SO 3 H Silica gel 380 6 5 Commercial product solid acid e -SO 3 H Styrene resin 50 24 * The specific surface area and the average pore diameter are values indicated in catalogues. The specific surface area and the average pore diameter were not available from catalogue for the commercial product solid acid b.
  • the acid strength and acid amount of the catalysts used in Example 1 were estimated by the ammonia TPD method.
  • the method is a way to examine the amount and strength of the acid site, in which adsorbed water is removed by pretreatment and then ammonia is adsorbed and desorbed by increasing temperature.
  • the desorption amount is plotted relative to the temperature during desorption by temperature increase, the acid amount and acid strength can be estimated from the extent of the desorption amount and the desorption temperature, respectively.
  • Fig. 2 also shows the temperature increase conditions and the like:
  • Ethanol was added to shredded leaf tobacco at a solid-liquid ratio of 1 g-wet tobacco: 10 ml, extraction was carried out while shaking in a water bath at 60°C for 1 hour and the liquid extract was separated from the extraction residue using a non-woven fabric. After concentrating the liquid extract to a predetermined concentration, the liquid extract was heated in a pressure resistance vessel together with 50% by weight of the commercial product solid acid c relative to the wet weight of tobacco at 120°C for 3 hours.
  • Comparative Example 1 Comparison to Patent Document 1: Reaction of hydrophobic fraction in a methanol liquid extract
  • Methanol was added to shredded leaf tobacco at a solid-liquid ratio of 1 g-wet tobacco: 5 ml, extraction was carried out while shaking in a water bath at 50°C for 1 hour and the liquid extract was separated from the extraction residue using a non-woven fabric. Methanol was volatilized from the liquid extract, equal amounts of hexane and water were added and the mixture was vigorously shaken. Only the organic phase was recovered from which hexane was volatilized, and then dissolved in ethanol. The solution was subjected to the reaction under the same conditions as in Example 1.
  • Fig. 3 shows the ethyl ester content in the treatment liquids of Example 2 and Comparative Example 1. It was confirmed that in Example 2, the amounts of diethyl malate and ethyl levulinate produced were particularly high, which otherwise were not generated in Comparative Example 1, and that ethyl palmitate was commonly generated in Example 1 and Comparative Example 1 was at a similar level.
  • the sensory evaluation of the smell of sidestream smoke was carried out by burning cigarettes in a room and comparing and evaluating the smell in the room after a predetermined period.
  • the evaluation was carried out by paired comparison and about 30 subjects were included in a panel per pair of evaluation. The panel chose which room between the two smelled more strongly of tobacco.
  • Fig. 4 shows the results of the choice between the two by the evaluation panel as to which had a stronger tobacco smell. According to Fig. 4 , significantly more people answered that the treated cigarettes had less tobacco smell. Thus, the effect of reducing the smell of tobacco sidestream smoke could be confirmed.
  • Fig. 5 shows the results of the choice between the two by the evaluation panel as to which had a stronger tobacco smell.
  • the numerical values on the vertical axis in Fig. 5 represents the weight proportion of the total ester amount relative to the amount of shredded tobacco A in each sample. Significantly more people answered that the test sample cigarettes had less tobacco smell. Thus, even by adding the composition of the present invention to separate shredded tobacco, the effect of reducing the smell of tobacco sidestream smoke could be confirmed.
  • Example 1 cigarettes prepared by adding to shredded tobacco A a composition obtained by isolating ester compounds by distillation under reduced pressure and solid phase extraction of the treatment liquid of Example 1 which is the method of the present invention (treated material was Japanese Flue-Cured tobacco, reaction conditions were 120°C and 3 hours, the amount of the catalyst added was 50% by weight per wet weight of tobacco).
  • the weight ratio of (tobacco used for preparation of the treatment liquid) : (shredded tobacco A to which the treatment liquid was added) was 1:2.
  • Comparative Example 1 cigarettes prepared in the same manner as in the above except that the treatment product added was prepared according to the manner in Comparative Example 1.
  • ester compounds generated by the method of the present invention were examined for contribution to the effect of reducing smell by adding reagents of the respective compounds to shredded tobacco.
  • Fig. 8-1 and Fig. 8-2 some of Examples above are again indicated by focusing on the abundance ratio of the components.
  • the numbers on the vertical axis in the figure correspond to the sample number in Table 4.
  • a selected proportion for test product in the table means the number of participants who found that the test product had a stronger smell out of all participants.
  • Table 5 Table corresponding to Fig. 9 Test product Ester content relative to the wet weight of the test product [%] Sensory evaluation result: Tobacco smell strength by choice between the two Ethyl levulinate Diethyl malate Ethyl palmitate Triethyl citrate Total Diethyl malate/all esters Test product (no. of people) Reference product (no. of people) Selected proportion for Test product [-] Sensory evaluation result (untreated material) 0.816 0.297 0.153 0.014 1.279 23.248 7 23 0.23 Sensory evaluation result 2-0.71% 0.328 0.287 0.060 0.038 0.713 40.203 6 24 0.20 Sensory evaluation result 5-No.
  • Fig. 9 shows the proportion of diethyl malate in the total ester amount and the selected proportion for tobacco smell by choice between the two in Table 5.
  • the value on the vertical axis in Fig. 9 of less than 0.5 means that the proportion of the people was high who found that the test product (to which ethyl ester compounds were added) had less smell of tobacco sidestream smoke than the reference product (to which ethyl ester compounds were not added) .
  • esterification reaction was carried out by allowing transfer of organic acids in tobacco leaves to a liquid phase by extraction with ethanol and heating the liquid extract under acidic conditions.
  • Ethanol used in this context is an extraction solvent of organic acids and is subjected to the esterification reaction.
  • Water was added to shredded leaf tobacco at a solid-liquid ratio of 1 g-wet tobacco : 10 ml, extraction was carried out while shaking in a water bath at 60°C for 1 hour and the liquid extract was separated from the extraction residue using a non-woven fabric.
  • To the water liquid extract was added 166% by weight of the catalyst per wet weight of tobacco and was shaken to carry out proton exchange.
  • the catalyst was separated and removed by filtration and water was volatilized under reduced pressure to obtain a proton-donated tobacco water extract.
  • the extract was dissolved in ethanol so as to attain a predetermined concentration and esterification reaction was carried out by heating at 120°C for 3 hours in a pressure resistance vessel.
  • Water was added to shredded leaf tobacco at a solid-liquid ratio of 1 g-wet tobacco : 10 ml, extraction was carried out while shaking in a water bath at 60°C for 1 hour and the liquid extract was separated from the extraction residue using a non-woven fabric.
  • To the water liquid extract was added 166% by weight of the catalyst per wet weight of tobacco and was shaken to carry out proton exchange.
  • the catalyst was separated and removed by filtration and water was concentrated up to a predetermined concentration to obtain a tobacco water extract.
  • the equivalent amount of ethanol to the water extract on the volume basis was added and esterification reaction was carried out by heating at 120°C for 3 hours in a pressure resistance vessel.
  • Example 3 The results in Examples 3 to 5 are shown in Table 6 and Fig. 10 .
  • Fig. 10 it was indicated that in the solutions extracted with water, the same reaction progressed as in the ethanol extraction above. Particularly in Example 4, diethyl malate was produced at about 8 times or more compared to Example 2, resulting in an improvement of the yield. It was believed that in Example 3, a reduction in the reaction rate due to an increase of contaminants more strongly affected than an increase in the amount of organic acids extracted with water.
  • Example 5 although the yield was decreased due to the reaction inhibition by water, it was possible to produce diethyl malate and ethyl palmitate even with a reduction of ethanol to a half amount.
  • Example 3 Example 4
  • Example 5 Amount of catalyst 100% 166% 166% Ethyl levulinate 0.5895 0.2706 0.0000 Diethyl malate 0.2494 2.5734 0.1641 Ethyl palmitate 0.0000 0.0000 0.0008 Triethyl citrate 0.0000 0.0447 0.0000
  • a solution obtained by dispersing the solution containing tobacco leaves after the reaction in a predetermined amount of ethanol and filtered through a 0.45 ⁇ m filter was subjected to GC-MS analysis under the above conditions to obtain qualitative information of the products.
  • the upper panel and the lower panel of Fig. 11 show GC charts of the treatment product of Example 6 and the standard reagents, respectively. From Fig. 11 , production of diethyl malate and ethyl palmitate was observed under the current conditions. Trace amounts of ethyl levulinate and triethyl citrate were observed. As the amount of the ethyl ester of citric acid was very low, it was estimated that citric acid added served mainly as a catalyst.
  • Citric acid has the first dissociation constant of 3.09 and is classified as a weak acid. It was demonstrated that in the method of the present invention, the reaction sufficiently proceeds even with a small amount of a weak acid.
  • the composition of the present invention has the effect of reducing the smell of tobacco sidestream smoke while smoking a tobacco product when the composition is added to an ingredient for a tobacco product such as shredded tobacco or the composition is used with tobacco leaves per se.
  • the present invention also provides a method for conveniently preparing the composition.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113876022A (zh) * 2021-09-20 2022-01-04 河南中烟工业有限责任公司 一种高分子型潜香缓释材料及其在加热卷烟中的应用
WO2023179870A1 (en) * 2022-03-25 2023-09-28 Symrise Ag Ethyl 4-oxopentanoate for reducing odors

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US3095882A (en) * 1961-08-04 1963-07-02 Philip Morris Inc Tobacco flavorants
DK1421863T3 (da) * 2001-08-07 2012-05-21 Japan Tobacco Inc Cigaret med dobbelt omslag og maskine og fremgangsmåde til at fremstille cigaretten
US7709014B2 (en) * 2005-10-17 2010-05-04 Yu Ruey J Hydroxy-oligocarboxylic esters: effects on nerve and use for cutaneous and mucocutaneous organs or sites
US20130125907A1 (en) * 2011-11-17 2013-05-23 Michael Francis Dube Method for Producing Triethyl Citrate from Tobacco

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113876022A (zh) * 2021-09-20 2022-01-04 河南中烟工业有限责任公司 一种高分子型潜香缓释材料及其在加热卷烟中的应用
WO2023179870A1 (en) * 2022-03-25 2023-09-28 Symrise Ag Ethyl 4-oxopentanoate for reducing odors

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