JP4408289B2 - Method for producing recycled tobacco material - Google Patents
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- JP4408289B2 JP4408289B2 JP2006514711A JP2006514711A JP4408289B2 JP 4408289 B2 JP4408289 B2 JP 4408289B2 JP 2006514711 A JP2006514711 A JP 2006514711A JP 2006514711 A JP2006514711 A JP 2006514711A JP 4408289 B2 JP4408289 B2 JP 4408289B2
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
- A24B15/241—Extraction of specific substances
- A24B15/245—Nitrosamines
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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
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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
- A24B3/00—Preparing tobacco in the factory
- A24B3/14—Forming reconstituted tobacco products, e.g. wrapper materials, sheets, imitation leaves, rods, cakes; Forms of such products
Abstract
Description
本発明は、再生タバコ材の製造方法に関する。 The present invention relates to a method for producing a recycled tobacco material.
天然のタバコの葉、刻み、中骨、茎、根等のタバコ材には、ニコチン、ニトロソアミン類、炭化水素類、タンパク質等種々の成分が含まれている。再生タバコ材の製造プロセスでは、天然のタバコ材から抽出したこれら成分を、同抽出残渣から作製した再生タバコウエブに掛け戻すことが行われている。これら天然タバコ材成分には、喫味または他の理由から、その量を減少させるか、除去することが望ましいものがある一方、除去しないか、あるいは増加させる方が望ましいものもある。 Tobacco materials such as natural tobacco leaves, chops, midbones, stems and roots contain various components such as nicotine, nitrosamines, hydrocarbons and proteins. In the production process of regenerated tobacco material, these components extracted from natural tobacco material are applied back to the regenerated tobacco web prepared from the extracted residue. While some of these natural tobacco ingredients are desirable to reduce or eliminate for reasons of taste or for other reasons, it may be desirable not to remove or increase them.
例えば、国際公開ＷＯ ０２／２８２０９は、タバコ固有のニトロソアミン（ＴＳＮＡ）を減少させるために、タバコを溶媒で抽出して得られた抽出液を活性炭、ゼオライト等の吸着剤と接触させる方法を開示している。特許文献１は、ニトロソアミンが減少した抽出液を再生タバコ材に添加することも開示している。
例えば、米国特許第５８１００２０号は、多量のクラウンエーテルを用いた液−液抽出処理によりニトロソアミン類を除去することを開示している。For example, International Publication No. WO 02/28209 discloses a method of bringing an extract obtained by extracting tobacco with a solvent into contact with an adsorbent such as activated carbon or zeolite in order to reduce tobacco-specific nitrosamines (TSNA). ing.
For example, US Pat. No. 5,810,020 discloses the removal of nitrosamines by liquid-liquid extraction treatment using a large amount of crown ether.
国際公開ＷＯ ０１／６５９５４は、タバコを超臨界二酸化炭素で処理してニトロソアミンを抽出し、その抽出物をニトロソアミン除去プロセスに供することを開示している。
天然タバコ材に含まれるニトロソアミン、特にＴＳＮＡは、除去することが望ましい物質である。しかしながら、ＴＳＮＡは、有用成分であるニコチンと構造が類似しており、ニコチンを除去することなくＴＳＮＡを選択的に除去することは困難である。そのため、従来の手法では、天然タバコ材から得た抽出液と抽出残渣である繊維成分を用いて有意量のニコチンを含有するが、ＴＳＮＡが実質的に除去された再生タバコ材を製造することが困難であった。
すなわち、国際公開ＷＯ ０２／２８２０９の手法では、ＴＳＮＡと硝酸や糖類との分離は可能であるが、吸着剤によりＴＳＮＡとともにニコチンも吸着除去されてしまう。International Publication WO 01/65954 discloses treating tobacco with supercritical carbon dioxide to extract nitrosamines and subjecting the extract to a nitrosamine removal process.
Nitrosamines, especially TSNA, contained in natural tobacco materials are desirable materials to remove. However, TSNA is similar in structure to nicotine, which is a useful component, and it is difficult to selectively remove TSNA without removing nicotine. Therefore, in the conventional method, it is possible to produce a regenerated tobacco material that contains a significant amount of nicotine using an extract obtained from natural tobacco material and a fiber component that is an extraction residue, but from which TSNA is substantially removed. It was difficult.
That is, in the method of International Publication WO 02/28209, TSNA can be separated from nitric acid and saccharides, but nicotine is also adsorbed and removed together with TSNA by the adsorbent.
また、米国特許第５８１００２０号の手法では、多量のクラウンエーテルを使用するため、安全性の面から好ましくない。さらに、国際公開ＷＯ ０１／６５９５４の手法では、超臨界抽出処理のコストが高いため、実用性に乏しいといえる。 Further, in the method of US Pat. No. 5,811,020, a large amount of crown ether is used, which is not preferable from the viewpoint of safety. Furthermore, it can be said that the method of International Publication WO 01/65954 is poor in practicality because the cost of the supercritical extraction process is high.
従って、本発明は、天然タバコ材から得た抽出液からニコチンとＴＳＮＡを比較的簡便に分離し、もって有意量のニコチンを含有するが、ＴＳＮＡが実質的に除去された再生タバコ材を製造する方法を提供することを目的とする。
本発明は、天然タバコ材から水系抽出溶媒で抽出して得られた抽出液と抽出残渣を用いて再生タバコ材を製造する方法を提供する。
本発明者らは、天然タバコ材から水系抽出溶媒で抽出して得られる抽出液においてニコチンとＴＳＮＡを分離する簡便な手法として活性炭のような強疎水性の吸着剤に注目した。活性炭のような強疎水性の吸着剤は、ＴＳＮＡとともにニコチンをも吸着する傾向にあるが、吸着処理時間と使用する吸着剤の量を制御することによって、ニコチンの吸着量を最小限に抑制して、ＴＳＮＡを有意に除去することができることを見いだした。本発明は、この知見に基づく。Accordingly, the present invention produces nicotine and TSNA relatively easily from an extract obtained from natural tobacco material, thereby producing a regenerated tobacco material containing a significant amount of nicotine but substantially free of TSNA. It aims to provide a method.
The present invention provides a method for producing a regenerated tobacco material using an extract obtained by extraction from a natural tobacco material with an aqueous extraction solvent and an extraction residue.
The present inventors paid attention to a strongly hydrophobic adsorbent such as activated carbon as a simple technique for separating nicotine and TSNA in an extract obtained by extraction from natural tobacco material with an aqueous extraction solvent. Strongly hydrophobic adsorbents such as activated carbon tend to adsorb nicotine along with TSNA, but by controlling the adsorption treatment time and the amount of adsorbent used, the amount of nicotine adsorbed can be minimized. Thus, it was found that TSNA can be removed significantly. The present invention is based on this finding.
すなわち、本発明によれば、（ａ）天然タバコ材を水系抽出溶媒で抽出し、該天然タバコ材の成分を含む抽出液と抽出残渣を得ること、（ｂ）前記抽出液を、吸着剤を用いた吸着分離操作に供してニトロソアミンを減少させること、（ｃ）前記抽出残渣を用いて再生タバコウエブを調製すること、および（ｄ）前記ニトロソアミンが減少した抽出液の少なくとも一部を前記再生タバコウエブに添加することを包含し、前記吸着剤が強疎水性の吸着剤であり、および前記吸着分離操作を、前記抽出液中の可溶性成分の重量の１０〜１１０％に相当する量の前記強疎水性吸着剤を用いて６０分間以内で行う再生タバコ材の製造方法が提供される。 That is, according to the present invention, (a) natural tobacco material is extracted with an aqueous extraction solvent to obtain an extract containing the components of the natural tobacco material and an extraction residue, and (b) the extract is adsorbed with an adsorbent. Subjecting the used adsorption separation operation to reduce nitrosamines, (c) preparing a regenerated tobacco web using the extraction residue, and (d) at least part of the nitrosamine-reduced extract from the regenerated tobacco. Adding to the web, the adsorbent is a strongly hydrophobic adsorbent, and the adsorptive separation operation is carried out in an amount corresponding to 10 to 110% of the weight of soluble components in the extract. Provided is a method for producing a regenerated tobacco material using a hydrophobic adsorbent within 60 minutes.
以下、本発明を種々の態様に沿ってより詳しく説明する。 Hereinafter, the present invention will be described in more detail along various aspects.
本発明は、強疎水性の吸着剤を用いて、天然タバコ材から水系抽出溶媒による抽出で得られた抽出液から、ニコチンの損失を極力抑えて、ＴＳＮＡ（Ｎ’−ニトロソノルニコチン（ＮＮＮ）、４−（メチルニトロソアミノ）−１−（３−ピリジル）−１−ブタノン（ＮＮＫ）、Ｎ’−ニトロソアナタビン（ＮＡＴ）等）を実質的に除去し、その抽出液を、抽出残渣を用いて調製された再生タバコウエブに添加することにより、再生タバコ材を製造する方法である。 In the present invention, TSNA (N′-nitrosonornicotine (NNN)) is obtained by suppressing loss of nicotine as much as possible from an extract obtained by extraction with an aqueous extraction solvent from a natural tobacco material using a strongly hydrophobic adsorbent. , 4- (methylnitrosoamino) -1- (3-pyridyl) -1-butanone (NNK), N′-nitrosoanatabine (NAT), etc.) is substantially removed, It is a method for producing a regenerated tobacco material by adding it to a regenerated tobacco web prepared using the same.
図１は、本発明の１つの態様により再生タバコ材を製造する方法を説明するためのフロー図である。 FIG. 1 is a flow diagram illustrating a method for producing a regenerated tobacco material according to one aspect of the present invention.
図１に示すように、まず、天然タバコ材１１と抽出溶媒１２を混合し、撹拌することにより天然タバコ材１１を抽出処理Ｓ１に供する。 As shown in FIG. 1, first, the natural tobacco material 11 and the
天然タバコ材１１としては、タバコの葉、刻み、中骨、茎、根およびそれらの混合物を用いることができる。抽出溶媒としては、水系溶媒を用いることができる。水等の水系抽出溶媒は、アルカリ性であっても、酸性であってもよい。水系抽出溶媒として、水と水混和性有機溶媒との混合物も使用し得る。そのような有機溶媒の例を挙げると、エタノールのようなアルコール類である。これら抽出溶媒には、水酸化ナトリウムのような無機塩を溶解して用いることもできる。抽出処理Ｓ１は、通常、５０〜１００℃の温度で、５分〜６時間程度行われる。 As the natural tobacco material 11, tobacco leaves, chops, medium bones, stems, roots, and mixtures thereof can be used. As the extraction solvent, an aqueous solvent can be used. The aqueous extraction solvent such as water may be alkaline or acidic. As the aqueous extraction solvent, a mixture of water and a water-miscible organic solvent can also be used. An example of such an organic solvent is an alcohol such as ethanol. In these extraction solvents, inorganic salts such as sodium hydroxide can be dissolved and used. The extraction process S1 is usually performed at a temperature of 50 to 100 ° C. for about 5 minutes to 6 hours.
抽出処理Ｓ１の終了後、得られた抽出混合物を例えばろ過等による分離操作Ｓ２に供し、抽出液１３と抽出残渣１４に分ける。抽出液１３は、天然タバコ材中の水溶性成分、例えばニコチン、ＴＳＮＡ等を含む。
抽出残渣１４は、実質的に繊維からなる。この抽出残渣１４を用いて、常法により、再生タバコウエブ１５を製造する。この再生タバコウエブ１５は、その一部が抽出残渣１４により構成されるものでもよいし、その全部が抽出残渣１４により構成されるものでもよい。After completion of the extraction process S1, the obtained extraction mixture is subjected to a separation operation S2 by, for example, filtration, and divided into an extract 13 and an
The
他方、分離操作Ｓ２から得られた抽出液１３は、強疎水性吸着剤を用いた吸着処理操作Ｓ４に供する。本発明において、この吸着分離操作Ｓ４は、抽出液１３を強疎水性吸着剤と接触させることにより行うことができる。強疎水性吸着剤とは、一般に疎水性が高いといわれている吸着剤であり、活性炭やスチレン系多孔質樹脂、もしくはスチレン系多孔質樹脂に臭素など疎水性をより一層強める修飾基（疎水性基）を導入した吸着剤を提示することができる。強疎水性の吸着剤を用いることにより、タバコ抽出液からニコチンの損失を極力抑えてＴＳＮＡを有意に除去することができる。 On the other hand, the extract 13 obtained from the separation operation S2 is subjected to an adsorption processing operation S4 using a strongly hydrophobic adsorbent. In the present invention, the adsorption separation operation S4 can be performed by bringing the extract 13 into contact with a strongly hydrophobic adsorbent. A strongly hydrophobic adsorbent is an adsorbent that is generally said to have high hydrophobicity, and is a modified group (hydrophobic, such as bromine on activated carbon, styrene porous resin, or styrene porous resin). An adsorbent having a group introduced therein can be presented. By using a strongly hydrophobic adsorbent, it is possible to significantly remove TSNA from the tobacco extract while minimizing the loss of nicotine.
抽出液１３と強疎水性吸着剤との接触は、抽出液１３に強疎水性吸着剤の粒子を添加し、撹拌することによって行うことができる。あるいは、抽出液１３と強疎水性吸着剤との接触は、強疎水性吸着剤の粒子を充填した吸着剤床に抽出液を通じることによっても行うことができる。 The contact between the extract 13 and the strongly hydrophobic adsorbent can be performed by adding particles of the strongly hydrophobic adsorbent to the extract 13 and stirring. Alternatively, the contact between the extract 13 and the strongly hydrophobic adsorbent can also be performed by passing the extract through an adsorbent bed filled with particles of the strongly hydrophobic adsorbent.
用いる強疎水性吸着剤の量は、抽出液１３中の可溶性成分の重量の１０〜１１０％に相当する量である。強疎水性吸着剤の量が１０％未満であると、抽出液中のＴＳＮＡを十分に除去することができず、他方その量が１１０％を越えると、ニコチンの吸着量が有意に増加する。強疎水性吸着剤の量は、抽出液１３中の可溶性成分の重量の１０〜５０％に相当する量であることが好ましい。なお、抽出液中の可溶性成分の量は、凍結乾燥法によって知ることができる。 The amount of the strongly hydrophobic adsorbent used is an amount corresponding to 10 to 110% of the weight of the soluble component in the extract 13. If the amount of the strongly hydrophobic adsorbent is less than 10%, TSNA in the extract cannot be sufficiently removed. On the other hand, if the amount exceeds 110%, the adsorbed amount of nicotine increases significantly. The amount of the strongly hydrophobic adsorbent is preferably an amount corresponding to 10 to 50% of the weight of the soluble component in the extract 13. In addition, the amount of the soluble component in the extract can be known by freeze drying.
また、抽出液１３と強疎水性吸着剤の接触時間は、６０分間以内である。この接触時間が６０以内であると、ニコチンの吸着を有意に抑制してＴＳＮＡを除去することができる。接触時間は、５分〜６０分間であることが好ましく、５分〜３０分間であることがより好ましい。 Moreover, the contact time of the extract 13 and the strongly hydrophobic adsorbent is within 60 minutes. When the contact time is 60 or less, the adsorption of nicotine is significantly suppressed and TSNA can be removed. The contact time is preferably 5 minutes to 60 minutes, and more preferably 5 minutes to 30 minutes.
本発明において、ニコチンの吸着を抑制し、ＴＳＮＡの吸着を増大させるという観点から、強疎水性吸着剤と接触させる際に、抽出液のｐＨ値は、２を超え、１０未満であることが好ましく、４を超え〜１０未満であることがより好ましい。このようなｐＨ値は、酸またはアルカリの添加により調整することができる。さらに、抽出液は０〜１００℃の温度にあることが好ましく、２０〜６０℃の温度にあることが好ましい。 In the present invention, from the viewpoint of suppressing the adsorption of nicotine and increasing the adsorption of TSNA, the pH value of the extract is preferably more than 2 and less than 10 when contacting with the strongly hydrophobic adsorbent. More preferably, it is more than 4 and less than 10. Such a pH value can be adjusted by adding an acid or an alkali. Furthermore, the extract is preferably at a temperature of 0 to 100 ° C, and preferably at a temperature of 20 to 60 ° C.
こうして吸着分離を行った抽出液を強疎水性吸着剤（使用済吸着剤１７）から分離（Ｓ５）する。この分離は、抽出液と強疎水性吸着剤との接触を抽出液中に強疎水性吸着剤を添加し撹拌することによって行った場合には、ろ過により行うことができる。また、抽出液と強疎水性吸着剤との接触を、抽出液を強疎水性吸着剤床に通じることによって行った場合には、吸着処理後の抽出液は、いうまでもなく、強吸着剤から分離された状態で、強疎水性吸着剤床から流出する。こうして得られる吸着処理済抽出液１６を濃縮し、または濃縮することなく、その一部または全部を再生タバコウエブ１５に添加（Ｓ５）することにより、再生タバコ材１８が得られる。こうして得られる再生タバコ材１８を用いて作製したシガレットは、燃焼時に生成する煙中のＴＳＮＡが有意に低減したものとなる。 The extract thus adsorbed and separated is separated from the strongly hydrophobic adsorbent (used adsorbent 17) (S5). This separation can be performed by filtration when the contact between the extract and the strongly hydrophobic adsorbent is performed by adding and stirring the strongly hydrophobic adsorbent in the extract. In addition, when the contact between the extract and the strongly hydrophobic adsorbent is performed by passing the extract through the strongly hydrophobic adsorbent bed, the extract after the adsorption treatment is, of course, the strong adsorbent. Effluent from the strongly hydrophobic adsorbent bed in a separated state. The regenerated
以上、本発明を態様に沿って説明したが、本発明は上記態様に限定されるものではない。いうまでもなく、上記種々の態様を組み合わせることもできる。 As mentioned above, although this invention was demonstrated along the aspect, this invention is not limited to the said aspect. Needless to say, the various aspects described above can be combined.
以下本発明を種々の例により説明するが、本発明はそれらに限定されるものではない。 Hereinafter, the present invention will be described with reference to various examples, but the present invention is not limited thereto.
以下の例において、ＴＳＮＡ量は、Ａｒｉｓｔａの刻み中ＴＳＮＡ測定法（Ｏｆｆｉｃｉａｌ Ｍｅｔｈｏｄ Ｔ−３０９，Ｄｅｔｅｒｍｉｎａｔｉｏｎ ｏｆ Ｎｉｔｒｏｓａｍｉｎｅｓ ｉｎ Ｗｈｏｌｅ Ｔｏｂａｃｃｏ，ｍａｄｅ ｂｙ ｔｈｅ Ｄｅｐａｒｔｍｅｎｔ ｏｆ Ｈｅａｌｔｈ，ｄａｔｅｄ Ｄｅｃｅｍｂｅｒ ３１，１９９９）に準じて測定した。すなわち、タバコ抽出液もしくは吸着剤処理液をＬＣ−ＭＳ／ＭＳに供して測定した。また、ニコチン量は、ドイツ標準化機構ＤＩＮ １０３７３に準ずる方法で行った。すなわち、タバコ抽出液もしくは吸着剤処理液に水酸化ナトリウムを加えアルカリ性にし、ついでヘキサンを加えて混合し、ニコチンをヘキサン相に移行させ、ヘキサン相のみをＧＣ／ＦＩＤに供して測定した。 In the following examples, the amount of TSNA was measured in accordance with the TSNA measurement method (Official Method T-309, Determination of Nitrosamines in Whole Tobacco, made by the Department of Health, d'Eth, 31 of Health, 31). That is, the tobacco extract or the adsorbent treatment solution was subjected to LC-MS / MS and measured. The amount of nicotine was measured by a method according to the German standardization organization DIN 10373. That is, sodium hydroxide was added to the tobacco extract or the adsorbent treatment solution to make it alkaline, and then hexane was added and mixed to transfer nicotine to the hexane phase, and only the hexane phase was subjected to GC / FID.
例１〜８
温度２５℃で、タバコ葉刻み（Ｘ−ＫＬ１）１００ｇを水１０００ｍＬと混合し、撹拌することによりタバコ刻みの抽出を行った。得られた抽出混合物をろ過し、抽出液と、抽出残渣に分けた。抽出残渣を抄紙して、再生タバコウエブを得た。Examples 1-8
At a temperature of 25 ° C., 100 g of tobacco leaf cut (X-KL1) was mixed with 1000 mL of water, and the tobacco cut was extracted by stirring. The obtained extraction mixture was filtered and divided into an extract and an extraction residue. Paper from the extraction residue was obtained to obtain a regenerated tobacco web.
他方、抽出液（ｐＨ６．０）に対し、その可溶性成分量に対し、表１に示す量（％）で活性炭（平均粒径：１１００μｍ；比表面積：１６３８ｍ２／ｇ）を加え、温度２５℃で、表１に示す時間（吸着処理時間）撹拌した後、ろ過した。吸着処理後の抽出液（ろ液）中に含まれる総ＴＳＮＡ量とニコチン量を分析した。結果を下記表１に併記する。表１には、総ＴＳＮＡ増減率とニコチン増減率も示す。表１中未処理とは、吸着処理を行っていない抽出液を指す（下記表２〜表６において同じ）。
表１に示す結果からは、抽出液中の可溶性成分量の１０〜５０％相当量の吸着剤（活性炭）を用い、吸着処理を５〜６０分間行うことにより、ＴＳＮＡが６０％以上を減少する一方で、ニコチン量の減少率を４０％未満に抑制できることがわかる（例１〜３および例５〜８）。特に、吸着剤の使用量が抽出液中の可溶性成分量の２５％相当量で、吸着処理時間が１５〜３０分間では、総ＴＳＮＡ増減率とニコチン増減率の階差が−６２〜−６６％と大きくなり、ＴＳＮＡの選択除去性が高くなることがわかる（例５〜例６）。 From the results shown in Table 1, TSNA is reduced by 60% or more by performing adsorption treatment for 5 to 60 minutes using an adsorbent (activated carbon) corresponding to 10 to 50% of the amount of soluble components in the extract. On the other hand, it turns out that the reduction rate of the amount of nicotine can be suppressed to less than 40% (Examples 1-3 and Examples 5-8). In particular, when the amount of adsorbent used is equivalent to 25% of the amount of soluble components in the extract and the adsorption treatment time is 15 to 30 minutes, the difference between the total TSNA increase / decrease rate and the nicotine increase / decrease rate is -62 to -66%. It can be seen that the selective removal of TSNA is enhanced (Examples 5 to 6).
例１〜３および例５〜６の吸着処理済抽出液を再生タバコウエブに添加して再生タバコ材を調製した。 Regenerated tobacco materials were prepared by adding the adsorption-treated extracts of Examples 1 to 3 and Examples 5 to 6 to the regenerated tobacco web.
例９〜１１
強疎水性吸着剤として臭素化学結合型スチレン樹脂系合成吸着剤（三菱化学社製ＳＰ２０７）を表２に示す量で用い、表２に示す時間抽出液と撹拌した以外は例１〜８と同様の操作を行った。吸着処理後の抽出液（ろ液）中に含まれる総ＴＳＮＡ量とニコチン量の分析結果を表２に併記する。
A bromine chemically bonded styrene resin synthetic adsorbent (SP207 manufactured by Mitsubishi Chemical Co., Ltd.) was used as a strong hydrophobic adsorbent in the amount shown in Table 2, and the same as in Examples 1 to 8 except that the mixture was stirred with the time extract shown in Table 2. Was performed. Table 2 shows the analysis results of the total TSNA amount and the nicotine amount contained in the extract (filtrate) after the adsorption treatment.
表２に示す結果からは、いずれの場合でも、総ＴＳＮＡ量が７０％以上減少している一方で、ニコチン量の減少率は２５％以下に抑制できることが分かる。特に、吸着剤の使用量が抽出液中の可溶性成分量の５０％相当量で、吸着処理時間が１５〜３０分間では、総ＴＳＮＡ増減率とニコチン増減率の階差が−６６％と大きくなり、ＴＳＮＡの選択除去性が高くなることがわかる（例９〜例１０）。 The results shown in Table 2 indicate that in all cases, the total TSNA amount is reduced by 70% or more, while the decrease rate of the nicotine amount can be suppressed to 25% or less. In particular, when the amount of adsorbent used is equivalent to 50% of the amount of soluble components in the extract and the adsorption treatment time is 15 to 30 minutes, the difference between the total TSNA increase / decrease rate and the nicotine increase / decrease rate increases to -66%. It can be seen that the selective removal of TSNA is enhanced (Examples 9 to 10).
例９〜１１の吸着処理済抽出液を再生タバコウエブに添加して再生タバコ材を調製した。 Regenerated tobacco materials were prepared by adding the adsorption-treated extracts of Examples 9 to 11 to the regenerated tobacco web.
例１２〜１４
活性炭として、平均粒径１５０μｍ、比表面積１１４０ｍ２／ｇの活性炭を表３に示す量で用い、表３に示す時間抽出液と撹拌した以外は例１〜８と同様の操作を行った。吸着処理後の抽出液（ろ液）中に含まれる総ＴＳＮＡ量とニコチン量の分析結果を表３に併記する。
As the activated carbon, activated carbon having an average particle diameter of 150 μm and a specific surface area of 1140 m 2 / g was used in the amounts shown in Table 3, and the same operations as in Examples 1 to 8 were performed except that the mixture was stirred with the extract solution for the time shown in Table 3. Table 3 shows the analysis results of the total TSNA amount and the nicotine amount contained in the extract (filtrate) after the adsorption treatment.
表３に示す結果からは、いずれの場合でも、総ＴＳＮＡ量が７０％以上減少している一方で、ニコチン量の減少率は３５％以下に抑制できることが分かる。特に、吸着剤の使用量が抽出液中の可溶性成分量の５０％相当量で、吸着処理時間が１５〜３０分間では、総ＴＳＮＡ増減率とニコチン増減率の階差が−７３〜−８４％と大きくなり、ＴＳＮＡの選択除去性が高くなることがわかる（例１２〜例１３）。 The results shown in Table 3 indicate that in any case, the total TSNA amount is reduced by 70% or more, while the reduction rate of the nicotine amount can be suppressed to 35% or less. In particular, when the amount of adsorbent used is equivalent to 50% of the amount of soluble components in the extract and the adsorption treatment time is 15 to 30 minutes, the difference between the total TSNA increase / decrease rate and the nicotine increase / decrease rate is -73 to -84%. It can be seen that the selective removal of TSNA is enhanced (Examples 12 to 13).
例１２〜１４の吸着処理済抽出液を再生タバコウエブに添加して再生タバコ材を調製した。 Regenerated tobacco materials were prepared by adding the adsorption-treated extracts of Examples 12 to 14 to the regenerated tobacco web.
例１５〜２０
例１〜８の手順に従ってタバコ刻みを抽出処理した後、得られた抽出液に酸（酢酸）またはアルカリ（水酸化ナトリウム）を添加することによってｐＨを２．０または１０．０に調整し、この抽出液を例１２〜１４で用いた活性炭により表４に示す条件で処理した。吸着処理後の抽出液（ろ液）中に含まれる総ＴＳＮＡ量とニコチン量の分析結果を表４に併記する。
After extracting tobacco cuts according to the procedures of Examples 1-8, the pH was adjusted to 2.0 or 10.0 by adding acid (acetic acid) or alkali (sodium hydroxide) to the resulting extract, This extract was treated under the conditions shown in Table 4 with the activated carbon used in Examples 12-14. Table 4 shows the analysis results of the total TSNA amount and the nicotine amount contained in the extract (filtrate) after the adsorption treatment.
表４に示すように、抽出液のｐＨが２．０であると、ＴＳＮＡとニコチンがともに吸着され難くなり（例１５〜１７）、また抽出液のｐＨが１０．０であるとＴＳＮＡとニコチンがともにほぼ９０％以上除去されてしまう（例１８〜２０）ことが分かる。例１２〜１４では抽出液のｐＨが６．０であり、その場合ＴＳＮＡの選択吸着性が優れていることを考慮すると、抽出液のｐＨは２を超え、１０未満であることが好ましいことがわかる。この結果は、ＴＳＮＡのｐＫａが４であり、ニコチンのｐＫａが１０であることによるものと考えられる。従って、抽出液のｐＨ値が、ＴＳＮＡがイオン化する４．０よりも大きく、ニコチンがイオン化する１０よりも小さいことがＴＳＮＡの選択的吸着除去により好ましいことがわかる。 As shown in Table 4, when the pH of the extract is 2.0, both TSNA and nicotine are hardly adsorbed (Examples 15 to 17), and when the pH of the extract is 10.0, TSNA and nicotine It can be seen that almost 90% or more are removed (Examples 18 to 20). In Examples 12 to 14, the pH of the extract is 6.0, and in that case, it is preferable that the pH of the extract is more than 2 and less than 10 in consideration of excellent selective adsorption of TSNA. Recognize. This result is considered to be due to the pKa of TSNA being 4 and the pKa of nicotine being 10. Therefore, it can be seen that the pH value of the extract is preferably larger than 4.0 at which TSNA is ionized and smaller than 10 at which nicotine is ionized by selective adsorption removal of TSNA.
例２１〜３８
活性炭の使用条件を表５に示すように変えた以外は例１〜８の手順を繰り返した。吸着処理後の抽出液（ろ液）中に含まれる総ＴＳＮＡ量とニコチン量の分析結果を表５に併記する。
The procedure of Examples 1-8 was repeated except having changed the use condition of activated carbon as shown in Table 5. Table 5 shows the analysis results of the total TSNA amount and the nicotine amount contained in the extract (filtrate) after the adsorption treatment.
表５に示すように、吸着剤の使用量と吸着処理時間が本発明で規定する範囲を逸脱すると、ニコチンの吸着を抑制してＴＳＮＡの吸着を向上させるという効果は達成されない。
例３９〜４７
吸着剤として親水性の吸着剤である活性アルミナを表６に示す量で用い、表６に示す時間抽出液と撹拌した以外は例１〜８と同様の操作を行った。吸着処理後の抽出液（ろ液）中に含まれる総ＴＳＮＡ量とニコチン量の分析結果を表６に併記する。
Examples 39-47
The same operations as in Examples 1 to 8 were performed except that activated alumina, which is a hydrophilic adsorbent, was used as the adsorbent in the amount shown in Table 6 and the mixture was stirred with the extract solution for the time shown in Table 6. Table 6 shows the analysis results of the total TSNA amount and the nicotine amount contained in the extract (filtrate) after the adsorption treatment.
表６に示すように、親水性吸着剤を用いた場合、ＴＳＮＡの除去がほとんど行えない。
以上述べたように、本発明によれば、天然タバコ材から得た抽出液から比較的簡便な手法によりニコチンとＴＳＮＡを分離することができ、ニコチンの損失を極力抑えて、ＴＳＮＡが実質的に除去された再生タバコ材を製造することができる。As shown in Table 6, when a hydrophilic adsorbent is used, TSNA can hardly be removed.
As described above, according to the present invention, nicotine and TSNA can be separated from an extract obtained from a natural tobacco material by a relatively simple method, and the TSNA is substantially reduced while suppressing the loss of nicotine as much as possible. The removed recycled tobacco material can be produced.
Claims (9)
（ｂ）前記抽出液を、吸着剤を用いた吸着分離操作に供してニトロソアミンを減少させること、
（ｃ）前記抽出残渣を用いて再生タバコウエブを調製すること、および
（ｄ）前記ニトロソアミンが減少した抽出液の少なくとも一部を前記再生タバコウエブに添加すること
を包含し、
前記吸着剤が強疎水性の吸着剤であり、および前記吸着分離操作を、前記抽出液中の可溶性成分の重量の１０〜１１０％に相当する量の前記強疎水性吸着剤を用いて５分〜３０分間で行う再生タバコ材の製造方法。(A) extracting natural tobacco material with an aqueous extraction solvent to obtain an extract containing the components of the natural tobacco material and an extraction residue;
(B) subjecting the extract to an adsorption separation operation using an adsorbent to reduce nitrosamines;
(C) preparing a regenerated tobacco web using the extraction residue; and (d) adding at least a portion of the nitrosamine-depleted extract to the regenerated tobacco web;
The adsorbent is a strongly hydrophobic adsorbent, and the adsorption separation operation is performed for 5 minutes using an amount of the strongly hydrophobic adsorbent corresponding to 10 to 110% of the weight of the soluble component in the extract. A method for producing a recycled tobacco material performed in 30 minutes .
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| WO2007032433A1 (en) * | 2005-09-15 | 2007-03-22 | Japan Tobacco Inc. | Method for production of recycled tobacco material |
| EP1951074B1 (en) * | 2005-11-07 | 2014-07-02 | Swedish Match North Europe AB | Method for producing nicotine with a reduced content of nitrosamines |
| JP2008125498A (en) * | 2006-11-27 | 2008-06-05 | Tetsuro Asao | Method for producing tobacco leaf |
| US9049886B2 (en) * | 2007-01-26 | 2015-06-09 | Philip Morris Usa Inc. | Methods and apparatus for the selective removal of constituents from aqueous tobacco extracts |
| CN101940361B (en) * | 2010-10-11 | 2012-09-19 | 广东中烟工业有限责任公司 | Method for extracting effective ingredient of tobacco leaf from waste tobacco |
| EP2526787A1 (en) * | 2011-05-26 | 2012-11-28 | Philip Morris Products S.A. | Methods for reducing the formation of tobacco specific nitrosamines in tobacco homogenates |
| CN102920012B (en) * | 2012-09-03 | 2016-04-20 | 上海聚华科技股份有限公司 | By the method for tobacco leaf reconstituted tobacco stem |
| CN102907760A (en) * | 2012-09-03 | 2013-02-06 | 上海聚华科技股份有限公司 | Method for regulating chemical components of tobacco material |
| WO2014141201A2 (en) | 2013-03-15 | 2014-09-18 | Fall Safall | Method of reducing tobacco-specific nitrosamines |
| CN103393210B (en) * | 2013-04-17 | 2015-09-30 | 杭州利群环保纸业有限公司 | Improve the method for papermaking-method reconstituted tobaccos suction quality |
| WO2014196033A1 (en) * | 2013-06-05 | 2014-12-11 | 日本たばこ産業株式会社 | Method for producing tobacco material |
| CA2940612C (en) * | 2014-02-26 | 2019-01-22 | Japan Tobacco Inc. | Producing method of tobacco raw material |
| CN106061295B (en) * | 2014-02-26 | 2018-03-09 | 日本烟草产业株式会社 | The manufacture method of the extracting method of fragranced composition and the inscape of preference |
| JP6101859B2 (en) | 2014-02-26 | 2017-03-22 | 日本たばこ産業株式会社 | Extracting method of flavor ingredient and manufacturing method of components of luxury products |
| CN104172462B (en) * | 2014-08-13 | 2016-03-30 | 安徽中烟工业有限责任公司 | The purification process of stem extracting solution in a kind of papermaking-method reconstituted tobaccos |
| CN104705779B (en) * | 2015-01-28 | 2016-08-17 | 中国烟草总公司郑州烟草研究院 | A kind of processing method improving cut stem quality |
| CN105077571A (en) * | 2015-09-01 | 2015-11-25 | 广西中烟工业有限责任公司 | Method for preparing tobacco sheet through enzymolysis extraction-Maillard reaction composite technology |
| CN107949283B (en) | 2015-09-08 | 2021-07-27 | 菲利普莫里斯生产公司 | Method for producing high tensile strength homogenized tobacco material |
| CN107802024B (en) * | 2017-10-25 | 2020-04-28 | 江苏中烟工业有限责任公司 | Preparation method of adsorbent-containing core material for low-temperature cigarettes |
| WO2023119517A1 (en) * | 2021-12-22 | 2023-06-29 | 日本たばこ産業株式会社 | Bleached tobacco residue, production method therefor, reconstituted tobacco material, production method therefor, and tobacco product |
| WO2023119516A1 (en) * | 2021-12-22 | 2023-06-29 | 日本たばこ産業株式会社 | Production method for tobacco flavored liquid, tobacco flavored liquid, reconstituted tobacco material, and tobacco product |
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| JPH05201925A (en) * | 1991-05-15 | 1993-08-10 | Philip Morris Prod Inc | Method of separation using organic acid, and new organic acid |
| US5810020A (en) * | 1993-09-07 | 1998-09-22 | Osmotek, Inc. | Process for removing nitrogen-containing anions and tobacco-specific nitrosamines from tobacco products |
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