WO2004110185A2 - Reduction du taux d'hydrocarbures aromatiques polycycliques dans la fumee du tabac a l'aide de sels de palladium - Google Patents

Reduction du taux d'hydrocarbures aromatiques polycycliques dans la fumee du tabac a l'aide de sels de palladium Download PDF

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Publication number
WO2004110185A2
WO2004110185A2 PCT/IB2004/002340 IB2004002340W WO2004110185A2 WO 2004110185 A2 WO2004110185 A2 WO 2004110185A2 IB 2004002340 W IB2004002340 W IB 2004002340W WO 2004110185 A2 WO2004110185 A2 WO 2004110185A2
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WO
WIPO (PCT)
Prior art keywords
tobacco
solution
cigarette
palladium
concentration
Prior art date
Application number
PCT/IB2004/002340
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English (en)
Other versions
WO2004110185A3 (fr
Inventor
Raquel M. Olegario
San Li
Joseph L. Banyasz
Kenneth H. Shafer
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 WO2004110185A2 publication Critical patent/WO2004110185A2/fr
Publication of WO2004110185A3 publication Critical patent/WO2004110185A3/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
    • A24B15/241—Extraction of specific substances
    • A24B15/246—Polycyclic aromatic compounds
    • 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
    • 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
    • A24B15/287—Treatment of tobacco products or tobacco substitutes by chemical substances by inorganic substances only
    • 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
    • A24B15/42—Treatment of tobacco products or tobacco substitutes by chemical substances by organic and inorganic substances

Definitions

  • the present invention is broadly concerned with tobacco containing at least one additive which reduces the level of polycyclic aromatic hydrocarbon (PAH) in smoke. More particularly, the invention relates to tobacco treated with a palladium salt to improve the quality of smoke by removing PAHs, especially benzo (a)pyrene (BaP), from the total particulate matter in tobacco smoke.
  • PAH polycyclic aromatic hydrocarbon
  • WO 02/37990 describes a catalyst system employing particles composed of metallic palladium.
  • a major disadvantage with this catalyst system is that it requires activation with nitrate or nitrite, which therefore must be present in the tobacco along with the metallic particles.
  • preparation of these metallic particles first requires that palladium ion be reduced to metallic palladium.
  • such metallic particles are typically lost from tobacco cut filler during the cigarette manufacturing process .
  • the present invention concerns a catalyst system useful for removing PAHs, including BaP, from both mainstream and sidestream tobacco smoke.
  • the present invention overcomes the problems associated with the above-noted catalyst system by eliminating the need for (1) particles, (2) reduction of the transition metal, and (3) a nitrate or nitrite activator.
  • the present invention relates to a method for preparing tobacco comprising adding to tobacco a solution containing a palladium salt.
  • the anion of the palladium salt is nitrate, chloride, or the anion of an organic acid.
  • the anion of the organic acid preferably is acetate, citrate, gluconate, or salicylate.
  • the solvent in the solution preferably is water, acetone, ethanol, a mixture of water and acetone, or a mixture of water and ethanol. If a mixture of water and acetone or a mixture of water and ethanol is used, then the concentration of acetone or ethanol in the mixture preferably is from 5% to 15% (v/v) .
  • the concentration of paladium in the prepared tobacco preferably is from 0.01% to 0.2% (w/w) , more preferably from 0.02% to 0.07% (w/w) .
  • the solution further contains mannitol and/or urea, with mannitol preferably being present in the prepared tobacco at a concentration of from 0.5% to 20% (w/w), more preferably from 8% to 12% (w/w) , and urea being present in the prepared tobacco at a concentration of from 0.5% to 10% (w/w), more preferably from 2% to 5% (w/w) .
  • the solution is added to the tobacco by spraying.
  • the weight of the solution added to the dry tobacco i.e., the tobacco before application of the solution
  • the weight of the dry tobacco to which the solution is added preferably is from 0.2 to 1.0, more preferably from 0.4 to 0.9, most preferably from 0.6 to 0.9.
  • the tobacco is dried, preferably by forced air or natural evaporation. If drying is done by forced air, then the forced air preferably has a relative humidity of from 50% to 70%.
  • a finite period of time is allowed to elapse between adding the solution to the tobacco and drying the tobacco.
  • this finite period of time is from 5 minutes to 24 hours, preferably from 15 minutes to 3 hours, more preferably from 15 minutes to 1.5 hours, most preferably from 30 minutes to one hour.
  • a smoking article preferably is made using the prepared tobacco. If the smoking article is a cigarette, then ventilation holes preferably are introduced. If the cigarette contains a paper, then ventilation holes preferably introduced in the paper. If the cigarette contains a filter, then ventilation holes preferably are introduced in the filter. If the cigarette contains a paper and a filter, then ventilation holes preferably are introduced in the paper and/or the filter.
  • the present invention also relates to tobacco and smoking articles, such as cigarettes, prepared by any of the above-described methods .
  • Figure 1 is a table which shows data demonstrating that treating tobacco with either the transition metal salt Pd(OOCCH 3 ) 2 or Pd (NO 3 ) 2 results in the reduction in the levels of four PAHs in mainstream smoke.
  • the term “Hold Time” refers to the length of time between the completion of spraying and the commencement of drying.
  • Solvent/Tobacco refers to the weight of the solution added to the tobacco divided by the "as is” weight of the tobacco to which the solution is added.
  • the term “OV” means oven drying for one hour or less at 60 0 C.
  • the term “NE” means natural evaporation.
  • the term “FA” means forced air having a relative humidity of 60%.
  • Figure 2 is a graph illustrating the reduction in the level of BaP in the mainstream smoke of tobacco treated with a Pd(OOCCH 3 ) 2 solution as a function of the concentration of palladium in the treated tobacco.
  • Figure 3 is a table which shows data demonstrating that mannitol and urea enhance the ability of a palladium salt to reduce the level of BaP in mainstream smoke.
  • Figure 4A is an illustration of a cigarette having four ventilation holes in the cigarette paper
  • Figure 4B is an illustration of a cigarette having four ventilation holes in the cigarette filter.
  • Figure 5 is a graph which shows data demonstrating that ventilation of either the cigarette paper or the cigarette filter enhances the ability of a palladium salt to reduce the level of BaP in mainstream smoke.
  • Figure 6 is a high resolution transmission electron microscope (HRTEM) image of an unpyrolysed sample.
  • the metal-bearing grains show two particle sizes.
  • the larger particles measure 5 run to several tens of nm in diameter.
  • Figure 7 is an HRTEM image of a sample pyrolysed at 300 0 C.
  • the Fast Fourier Transform (the inset) demonstrates d-spacing corresponding to Palladium metal only.
  • Figure 8 is a graph which shows the Fourier transform of samples pyrolysed at different temperatures and the two end materials (unpyrolysed sample and Pd foil) .
  • Figure 9 is a graph which shows filtered k 2 data for the near neighbour shell of Pd for a sample pyrolysed at 250 0 C.
  • the vertical lines show the extent of the fit in R- space and the range of Fourier transform in original k-space.
  • Figure 10 is a table showing structural information derived from XAFS analysis on Pd-O coordination with Pd as the central atom, n is the average percentage of first shell oxygen atom around Pd atom, in samples pyrolyzed at various temperatures. After heating at 600 0 C palladium is predominantly reduced to its metallic state.
  • Tobacco was treated by spraying either a Pd (0OCCH 3 ) 2 solution or a Pd (NO 3 ) 2 solution onto "as is" tobacco. The tobacco was then dried. The concentration of metal in the resultant treated tobacco was 0.05% (w/w) .
  • the Pd (NO 3 ) 2 solution was prepared by dissolving the salt in water.
  • the Pd (0OCCH 3 ) 2 solution was prepared by dissolving the salt in one part of acetone, followed by the addition of nine parts of water. Subsequently, the mainstream smoke of treated and untreated tobacco was analyzed for the presence of the following PAHs: phenanthrene, benzo (a) antracene (BaA), pyrene, and BaP.
  • the percent reduction in the level of each of these PAHs was calculated using the following formula: 100(1- (level of the PAH in mainstream smoke of treated tobacco/level of the PAH in mainstream smoke of untreated tobacco) ) , wherein the PAH is phenanthrene, BaA, pyrene, or BaP.
  • the results of these experiments are given in Figure 1.
  • Tobacco was treated by spraying either a Pd (0OCCH 3 ) 2 solution or a Cu (00CCH 3 ) 2*H 2 0 solution onto "as is" tobacco. The tobacco was then dried.
  • the Pd (0OCCH 3 ) 2 solution was prepared as described in Example 1.
  • the Cu (0OCCH 3 ) 2 # H 2 0 solution was prepared by dissolving the salt in water.
  • the mainstream smoke of treated and untreated tobacco was analyzed for the presence of BaP and other PAHs .
  • the percent reduction in BaP level was calculated using the following formula: 100(1- (level of BaP in mainstream smoke of treated tobacco/level of BaP in mainstream smoke of untreated tobacco) ) . The results of these experiments are given in Figure 2.
  • Tobacco was treated by spraying onto "as is" tobacco either a Pd (0OCCH 3 ) 2 solution or a Pd (0OCCH 3 ) 2 solution additionally containing mannitol and urea.
  • the tobacco was then dried.
  • the concentration of palladium in the resultant treated tobacco was 1.4% (w/w) .
  • the concentrations of mannitol and urea in the resultant treated tobacco containing these compounds was 10% and 5% (w/w) , respectively.
  • the mainstream smoke of treated and untreated tobacco was analyzed for the presence of BaP.
  • the percent reduction in BaP level was calculated using the formula noted in Example 2. The results of these experiments are given in Figure 3.
  • Cigarettes were prepared using the treated tobacco and cigarette paper having a porosity of 33 CORESTA units. Three types of cigarettes were prepared: (1) unventilated cigarettes, (2) cigarettes ventilated in the cigarette paper, with each cigarette having four 0.5 mm- diameter holes approximately 6 mm apart (see Figure 4A) , and (3) cigarettes ventilated in the cigarette filter, with each filter having four 0.5 mm-diameter holes approximately 5 mm apart (see Figure 4B) . Subsequently, the mainstream smoke from each of the three types of cigarettes was analyzed for the presence of BaP. Percent reduction in BaP level was calculated using the formula noted in Example 2. The results of these experiments are given in Figure 5.
  • X-ray Absorption Fine Structure was used to study the catalytic effect of metal on the thermal decomposition of cellulose as a function of termperature.
  • Macrocrystalline cellulose powder containing 1% of metal was prepared using Pd (0OCCH 3 ) 2 as the metal source.
  • the resulting samples were pyrolyzed isothermally in helium, for 10 minutes, at temperatures ranging from 150 0 C to 600 0 C.
  • High Resolution Transmission Electron Microscope (HRTEM) indicated the presence of a relatively uniform particle size distribution in the low nanometer range.
  • X-ray Absorption Fine Structure is a powerful technique in characterization of catalyst both in its static and dynamic state (in-situ conditions) . It can provide the interatomic distances and the coordination numbers between a particular atom and the surrounding atoms in the first, second and third coordination shells.
  • a great advantage of the XAFS technique in relation to catalyst characterization is the ability to perform measurements under realistic conditions.
  • Suitably designed in-sltu reaction chambers will allow us to study a working catalyst at elevated temperature and pressure.
  • Microcyrstalline cellulose powder containing 1 w/w% palladium was prepared using palladium acetate as the source of metal.
  • Cellulose and acetone solution of Pd (0OCCH 3 ) 2 were combined into a slurry, followed by solvent evaporation at room temperature. This procedure allowed maximum dispersion and minimal reduction of palladium.
  • the char samples were obtained by pyrolysis of the cellulose/palladium acetate mixture at various temperatures in a quartz reactor according to the experimental design of McGrath, et al. For each temperature the initial mixture was pyrolyzed for 10 minutes under constant helium flow of 120 N cm3/min at atmospheric pressure.
  • a Philip's FEI Techni field emission high resolution transmission electron microscope was used to estimate the morphology the Pd particles .
  • the image of the unpyrolyzed starting material is shown in Figure 6.
  • the fast Fourier transform indicated many reflections that could not be indexed as Pd metal, which were probably palladium acetate. Heating of the sample to 300 0 C seemed to reduce Pd to its metallic state.
  • the FFT of the image demonstrated d- spacing corresponding to Pd metal only (Fig. 7) with particle sized smaller than 5 nm.
  • TEM images of the sample pyrolyzed at 600°C indicated a typical particle size of IOnm or greater. Selected area electron diffraction patterns revealed that these particles consisted exclusively of palladium metal.
  • GC gas chromatograph
  • MS mass spectrometer
  • XAFS measurements were carried out at the National Synchrotron Light Source (NSLS) of Brookhaven National Laboratory at beam-line XIlA.
  • the x-ray beam was monochromatized by using a Si(IIl) double crystal monochromator .
  • the storage ring was operated at 2.8GeV with a maximum beam current of 30OmA.
  • XAFS spectra were collected, at room temperature, at Pd K-edge, in both fluorescence and transmission mode.
  • the energy of monochromatized beam was calibrated using a pre-edge peak of a 5nm thick Pd foil.
  • XAFS data was reduced and analyzed using the data analysis package developed at the University of Washington. The pre edge and background were subtracted from the normalized data set. The resulting absorption spectra were averaged before further analysis .
  • n is the average percentage of first shell oxygen atom around Pd atom, in samples pyrolyzed at various temperatures .
  • XAFS data will be taken at lower temperature (77K) to reduce thermal disorder in XAFS measurements.
  • XAFS In-situ XAFS measurements will be used to elucidate the catalytic performance of the metal.
  • the structures of catalysts are greatly dependent on the reaction condition due to direct chemical interaction with the reactants. Thus, information on the nature of active catalytic sites under reaction condition is essential for designing better catalysts.
  • XAFS is an ideal tool for structural analysis of active sites under the reaction conditions, because X-rays are not generally interfered with by the reaction gases present in the catalytic system.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

Procédés de traitement du tabac dans le but de réduire le taux de certains composés dans la fumée du tabac, et articles pour fumeurs correspondants renfermant ce tabac traité. Selon lesdits procédés, on applique au tabac, de préférence par pulvérisation, une solution renfermant un sel de palladium. Le sel de palladium contient de préférence un nitrate, un chlorure, un acétate, un citrate, un gluconate ou un salicylate à titre d'anion. Après application de la solution, le tabac est de préférence séché dans un four, par air forcé, ou par évaporation naturelle. Le palladium compris dans le tabac traité entraîne une réduction du taux d'hydrocarbures aromatiques polycycliques, et notamment de benzo(a)pyrène, dans les matières particulières totales présentes dans le flux principal et le flux secondaire de la fumée du tabac traité. L'adjonction au tabac de mannitol et/ou d'urée et l'introduction d'évents dans une cigarette renfermant le tabac traité améliorent l'aptitude du palladium à réduire le taux d'hydrocarbures aromatiques polycycliques présents dans la fumée.
PCT/IB2004/002340 2003-06-18 2004-06-17 Reduction du taux d'hydrocarbures aromatiques polycycliques dans la fumee du tabac a l'aide de sels de palladium WO2004110185A2 (fr)

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US47942203P 2003-06-18 2003-06-18
US60/479,422 2003-06-18

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WO2004110185A3 WO2004110185A3 (fr) 2005-01-27

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010084792A1 (fr) 2009-01-23 2010-07-29 日本たばこ産業株式会社 Cigarette
CN103815533A (zh) * 2014-03-06 2014-05-28 川渝中烟工业有限责任公司 降低烤烟中苯并芘释放量的烘烤工艺方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7819123B2 (en) * 2006-06-26 2010-10-26 Philip Morris Usa Inc. Process and apparatus for applying palladium salts to tobacco filler
CN109621595B (zh) * 2018-12-29 2023-09-22 佛山市云米电器科技有限公司 根据厨房油烟成分的除油喷雾系统及油烟除油喷雾方法

Citations (9)

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US3572348A (en) * 1968-08-01 1971-03-23 Liggett & Myers Inc Tobacco composition
GB1255564A (en) * 1968-08-29 1971-12-01 Nat Patent Dev Corp Tobacco smoke filters
US4055191A (en) * 1974-04-05 1977-10-25 Liggett & Myers Incorporated Tobacco composition
US4216784A (en) * 1977-10-03 1980-08-12 Liggett Group Inc. Tobacco composition
WO1980002023A1 (fr) * 1979-03-28 1980-10-02 Gallaher Ltd Procedes catalytiques et catalyseurs
US4248251A (en) * 1979-02-21 1981-02-03 Liggett Group Inc. Tobacco composition
US4256609A (en) * 1978-01-20 1981-03-17 Gallaher Limited Catalysts
EP0499402A1 (fr) * 1991-02-15 1992-08-19 Philip Morris Products Inc. Conversion de monoxyde de carbone avec des mélanges de métaux de transition comme catalyseurs
WO2002037990A2 (fr) * 2000-11-10 2002-05-16 Vector Tobacco Ltd. Procede et produit servant a extraire des substances cancerogenes de la fumee du tabac

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US3511247A (en) * 1968-05-10 1970-05-12 Philip Morris Inc Smoking product and method of making the same
US4177822A (en) * 1973-03-26 1979-12-11 Liggett Group Inc. Tobacco composition
US4235251A (en) * 1979-02-21 1980-11-25 Liggett Group Inc. Stability of tobacco casing systems containing palladium
US4257430A (en) * 1979-02-21 1981-03-24 Liggett Group Inc. Tobacco composition including palladium
US4236533A (en) * 1979-04-13 1980-12-02 Tkr Tabak Forschnugs-Gmbh & Co. Novel cigarette process and product produced therefrom

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3572348A (en) * 1968-08-01 1971-03-23 Liggett & Myers Inc Tobacco composition
GB1255564A (en) * 1968-08-29 1971-12-01 Nat Patent Dev Corp Tobacco smoke filters
US4055191A (en) * 1974-04-05 1977-10-25 Liggett & Myers Incorporated Tobacco composition
US4216784A (en) * 1977-10-03 1980-08-12 Liggett Group Inc. Tobacco composition
US4256609A (en) * 1978-01-20 1981-03-17 Gallaher Limited Catalysts
US4248251A (en) * 1979-02-21 1981-02-03 Liggett Group Inc. Tobacco composition
WO1980002023A1 (fr) * 1979-03-28 1980-10-02 Gallaher Ltd Procedes catalytiques et catalyseurs
EP0499402A1 (fr) * 1991-02-15 1992-08-19 Philip Morris Products Inc. Conversion de monoxyde de carbone avec des mélanges de métaux de transition comme catalyseurs
WO2002037990A2 (fr) * 2000-11-10 2002-05-16 Vector Tobacco Ltd. Procede et produit servant a extraire des substances cancerogenes de la fumee du tabac

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010084792A1 (fr) 2009-01-23 2010-07-29 日本たばこ産業株式会社 Cigarette
JPWO2010084792A1 (ja) * 2009-01-23 2012-07-19 日本たばこ産業株式会社 シガレット
CN103815533A (zh) * 2014-03-06 2014-05-28 川渝中烟工业有限责任公司 降低烤烟中苯并芘释放量的烘烤工艺方法

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WO2004110185A3 (fr) 2005-01-27

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