WO2006059229A1 - Procede permettant de limiter la generation de benzo[a]pyrene lors de l'usage de tabac - Google Patents

Procede permettant de limiter la generation de benzo[a]pyrene lors de l'usage de tabac Download PDF

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Publication number
WO2006059229A1
WO2006059229A1 PCT/IB2005/003972 IB2005003972W WO2006059229A1 WO 2006059229 A1 WO2006059229 A1 WO 2006059229A1 IB 2005003972 W IB2005003972 W IB 2005003972W WO 2006059229 A1 WO2006059229 A1 WO 2006059229A1
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WO
WIPO (PCT)
Prior art keywords
tobacco
extraction
propanol
benzo
smoking article
Prior art date
Application number
PCT/IB2005/003972
Other languages
English (en)
Inventor
Thomas E. Mcgrath
Stephen A. Haut
W. Geoffrey Chan
Original Assignee
Philip Morris Products S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Philip Morris Products S.A. filed Critical Philip Morris Products S.A.
Publication of WO2006059229A1 publication Critical patent/WO2006059229A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • 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
    • 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
    • A24B15/246—Polycyclic aromatic compounds

Definitions

  • a process for manufacturing a smoking article having reduced generation of benzo [a]pyrene (B [a] P) during smoking thereof comprising preparing a treated tobacco by contacting a tobacco material with an extraction solvent consisting essentially of methanol, ethanol, 1-propanol or 2- propanol; and incorporating the treated tobacco in a smoking article.
  • the extraction is carried out on tobacco which has not been subjected to extraction with acetone
  • the contacting is carried out in a Soxhlet extractor. •
  • the contacting results in a reduction in weight of the tobacco material. More preferably, the reduction is at least about 25%, still more preferably at least about 40%.
  • the smoking article exhibits a reduction in benzo [a]pyrene in tobacco smoke of at least about 25%, preferably at least about 35%, when the treated tobacco is pyrolyzed at 600 0 C in an inert atmosphere.
  • the extraction is carried out with a solvent consisting of methanol.
  • the extraction is carried out with a solvent consisting of ethanol.
  • the extraction is carried out with a solvent consisting of 1-propanol.
  • the extraction is carried out with a solvent consisting of 2-propanol.
  • the invention also provides a smoking article, preferably a cigarette, manufactured by a process according to the invention.
  • Figure 1 depicts B [a] P yields from the 600 ° C pyrolysis in Helium of solvent extracted bright tobacco (120 ml/min flow rate, 600 ° C /min heating rate, 10 min) .
  • Figure 2 depicts the effect of proline (0.4% w/w) and lipids on the yield of B [a] P from the 600 ° C pyrolysis of a carbohydrate + lignin mixture.
  • the lipid mixture consists of oleic acid (lmg) , linoleic acid(2mg), linolenic acid (3.5mg), stigmasterol (0.8mg, chlorogenic acid (8mg) and solanesol (15mg) dissolved in methanol.
  • PAHs polycyclic aromatic hydrocarbons
  • Benzo [a]pyrene (B [a] P) a 5-ring PAH
  • lipophilic tobacco components such as phytosterols, saturated aliphatic hydrocarbons, and terpenoid compounds were believed to be the major precursors of PAHs formed from a burning cigarette.
  • a number of solvent extracted tobaccos and individual tobacco components such as sterols, long-chain hydrocarbons, fatty acids, carbohydrates and polyphenols have been pyrolyzed at 600 ° C in an effort to identify low temperature B [a] P precursors.
  • the yield of B [a] P obtained per gram of sample pyrolyzed has been normalized to the amount of each component present in tobacco.
  • the B [a] P yield from a mixture of selected tobacco lipophilic and cell wall components has also been investigated.
  • the pyrolysis setup used was described in McGrath, T. E. et al. , J. Anal. Appl. Pyrol . , 66 (2003) 51-70.
  • the experimental setup consisted of a 2.5cm i.d. quartz tube placed inside a 30cm long heated Carbolite furnace having an isothermal length of ca. 7cm at a temperature of 600 ° C.
  • Helium was used as the carrier gas at a flow rate of 120cm 3 /min.
  • the residence time of gas phase pyrolysis products in the isothermal section of the reactor was calculated to be approximately 4s at a furnace temperature of 600 ° C.
  • a fiber-glass filter placed in a housing assembly immediately at the end of the quartz tube on the exit side of the furnace was used to collect ' the product tar condensate.
  • the temperature of the sample in the heated quartz tube was measured using a chromel/alumel (K type) thermocouple.
  • the thermocouple was also used to transport the ceramic boat containing the samples to and from the heated isothermal region of the quartz tube.
  • Oleic acid (99+%) , linoleic acid(99%) , stigmasterol (9.3%) and cholesterol (99+%) were purchased from Aldrich. Linolenic acid (90%, remainder linoleic acid) and D (+) -proline (99+%) were purchased from Acros. Chlorogenic acid (95+%) and solanesol (90+% from tobacco leaves) were obtained from Sigma.
  • oleic acid (lmg/g) , linoleic acid(2mg/g), linolenic acid (3.5mg/g) , stigmasterol (0.8mg/g), chlorogenic acid (8mg/g) and solanesol .(15mg/g) was prepared in methanol and added to a mixture of carbohydrates and lignin.
  • Avicel cellulose, xylan from birch wood, pectin from citrus fruits, and hydrolytic lignin were used as ' model tobacco cell wall components.
  • the Avicel cellulose sample was obtained from FCI and is a microcrystalline purified and depolymerized alpha-cellulose derived from fibrous plants (Avicel PH-102) . It has an ash content of less than 0.007%.
  • the birchwood xylan ( ⁇ 95% xylose) sample was obtained from Fluka.
  • the pectin sample was obtained from Sigma and has a galacturonic and methoxy content of 81% and 8.6%, respectively.
  • D-glucose was used as a model tobacco sugar. The D-glucose sample was obtained from Acros and is 99+% reagent grade.
  • a mixture of cellulose, hemicellulose, pectin, glucose, and lignin was made up with the following component ratios of 1:1:1:1:0.3, respectively.
  • the resulting mixture is denoted as Carbo-Lig Mix throughout the rest of the text.
  • the samples also contained smaller amounts of Calcium.
  • a sample of tobacco or model tobacco compound to be pyrolyzed was placed in a ceramic boat that initially rested in an unheated section of the quartz tube outside of the heated furnace.
  • a tar trap assembly was placed on the exit side of the furnace. After the furnace had reached the desired set temperature, for example, 600 ° C, the sample was ' pushed to the isothermal region in the furnace and pyrolyzed for a total of 10 minutes.
  • the boat was pulled back to the unheated section of the quartz tube and the remaining solid residue was allowed to. cool to room temperature.
  • the fiber-glass filter was removed, placed in an amber screw capped vial, and the washings from the pad housing assembly walls was added to the vial.
  • A.total solvent level of 5 mL of methanol was used and the vial was left to stir overnight on a shaker.
  • the quartz tube was cleaned in air at a temperature of 650 ° C.
  • the tar fractions collected were, analyzed by GC-MS using an Agilent 6890 GC equipped with an Agilent 5973 quadrupole MSD analyzer operating in the single ion mode (SIM) .
  • the yield of B [a] P was calculated using a calibration curve obtained from the analysis of standard solutions of B [a] P ranging from lOng/ml to lOOOng/ml.
  • B [a] P obtained from the pyrolysis of 11 individual components at 600 ° C in Helium for a total heating time of 10 min are give in Table 1.
  • Stigmasterol b ( ⁇ 0.8mg/g) 1200 0.9
  • Linoleic acid ( ⁇ 2mg/g) 175 0.35
  • Linolenic acid ( ⁇ 4mg/g) 335 1.34
  • ND not detected.
  • a carbohydrate + lignin mixture (Carbo-Lig mix) was pryolyzed in the presence of an amino acid (proline) and a mixture of tobacco lipid components. 0.4% w/w of D(+) -proline was physically mixed with the Carbo-Lig mix.
  • the lipid mixture consisted of oleic acid (lmg/g) , linoleic acid (2mg/g) , linolenic acid (3.5mg/g), stigmasterol (0.8mg/g), chlorogenic acid (8mg/g) and solanesol (15mg/g) .
  • the amounts of amino acid and lipids added are consistent with the amount of each component present in bright tobacco. As shown in Fig.
  • Extraction of bright tobacco lamina with hexane and ethyl acetate removes lipophilic components of tobacco but does not lead to a decrease in B[a] P formed.
  • Extraction with methanol decreases the B [a] P yield by 35% whereas extraction with water significantly increases the yield of B [a] P.
  • the methanol extraction process appears to remove low temperature B[a] P precursors while extraction with water appears to concentrate B [a] P precursors on a per gram of material basis. From the individual tobacco components pyrolyzed at 600 ° C, only the tobacco carbohydrates and cell wall components such as glucose, cellulose, hemicellulose and lignin appear to contribute significantly to the formation of B [a] P.
  • Extraction of tobacco can also reduce generation of B [a] P during smoking.
  • the extraction with the methanol, ethanol, 1-propanol or 2-propanol is preferably carried out on tobacco which has not been subjected to a prior extraction with acetone.
  • the extraction is preferably carried out using a single solvent selected from the group consisting of methanol, ethanol, 1-propanol and 2-propanol .

Landscapes

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

Abstract

L'invention concerne un procédé permettant de produire un article à fumer à génération de benzo[alpyrène limitée lorsqu'on le fume. Ledit procédé consiste à préparer un tabac traité par contact d'un matériau de tabac avec un solvant d'extraction composé essentiellement de méthanol, d'éthanol et de 1-propanol ou 2-propanol; et à incorporer le tabac traité dans l'article à fumer. L'invention concerne également un article à fumer tel qu'une cigarette produite à l'aide dudit procédé.
PCT/IB2005/003972 2004-12-01 2005-12-01 Procede permettant de limiter la generation de benzo[a]pyrene lors de l'usage de tabac WO2006059229A1 (fr)

Applications Claiming Priority (2)

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US63198404P 2004-12-01 2004-12-01
US60/631,984 2004-12-01

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WO2006059229A1 true WO2006059229A1 (fr) 2006-06-08

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WO2012068375A1 (fr) * 2010-11-18 2012-05-24 R. J. Reynolds Tobacco Company Extrait de tabac séché au feu et produits du tabac fabriqués avec celui-ci
WO2013144766A1 (fr) 2012-03-28 2013-10-03 Philip Morris Products S.A. Compositions de tabac liquide
CN103908016A (zh) * 2014-03-31 2014-07-09 河南中烟工业有限责任公司 烟草减害处理溶剂及降低卷烟主流烟气中hcn的方法
CN104351945A (zh) * 2014-10-17 2015-02-18 云南中烟工业有限责任公司 一种降低烟丝中苯并[a]芘前体化合物的方法和装置
CN106263013A (zh) * 2016-11-22 2017-01-04 河南中烟工业有限责任公司 一种高香气烟草提取物及其应用
CN106307604A (zh) * 2016-11-22 2017-01-11 中国烟草总公司郑州烟草研究院 烟草提取物、提取方法和应用

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012068375A1 (fr) * 2010-11-18 2012-05-24 R. J. Reynolds Tobacco Company Extrait de tabac séché au feu et produits du tabac fabriqués avec celui-ci
CN103369978A (zh) * 2010-11-18 2013-10-23 R.J.雷诺兹烟草公司 火烤烟草提取物和由其制成的烟草产品
WO2013144766A1 (fr) 2012-03-28 2013-10-03 Philip Morris Products S.A. Compositions de tabac liquide
US10271574B2 (en) 2012-03-28 2019-04-30 Philip Morris Products S.A. Liquid tobacco composition
CN103908016A (zh) * 2014-03-31 2014-07-09 河南中烟工业有限责任公司 烟草减害处理溶剂及降低卷烟主流烟气中hcn的方法
CN104351945A (zh) * 2014-10-17 2015-02-18 云南中烟工业有限责任公司 一种降低烟丝中苯并[a]芘前体化合物的方法和装置
CN106263013A (zh) * 2016-11-22 2017-01-04 河南中烟工业有限责任公司 一种高香气烟草提取物及其应用
CN106307604A (zh) * 2016-11-22 2017-01-11 中国烟草总公司郑州烟草研究院 烟草提取物、提取方法和应用
CN106263013B (zh) * 2016-11-22 2018-07-06 河南中烟工业有限责任公司 一种高香气烟草提取物、制备方法及其应用

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