US20060162733A1 - Process of reducing generation of benzo[a]pyrene during smoking - Google Patents
Process of reducing generation of benzo[a]pyrene during smoking Download PDFInfo
- Publication number
- US20060162733A1 US20060162733A1 US11/289,314 US28931405A US2006162733A1 US 20060162733 A1 US20060162733 A1 US 20060162733A1 US 28931405 A US28931405 A US 28931405A US 2006162733 A1 US2006162733 A1 US 2006162733A1
- Authority
- US
- United States
- Prior art keywords
- tobacco
- process according
- extraction
- benzo
- pyrene
- 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.)
- Abandoned
Links
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000008569 process Effects 0.000 title claims abstract description 22
- 230000000391 smoking effect Effects 0.000 title claims abstract description 19
- 241000208125 Nicotiana Species 0.000 claims abstract description 69
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 27
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000605 extraction Methods 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 230000009467 reduction Effects 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 235000019504 cigarettes Nutrition 0.000 claims description 7
- 239000000779 smoke Substances 0.000 claims 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 238000000197 pyrolysis Methods 0.000 description 11
- 229920005610 lignin Polymers 0.000 description 10
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 8
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 8
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 8
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 7
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 7
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 239000010453 quartz Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- AFPLNGZPBSKHHQ-UHFFFAOYSA-N Betulaprenol 9 Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO AFPLNGZPBSKHHQ-UHFFFAOYSA-N 0.000 description 6
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 6
- 229920002488 Hemicellulose Polymers 0.000 description 6
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 6
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 6
- 229940074393 chlorogenic acid Drugs 0.000 description 6
- 235000001368 chlorogenic acid Nutrition 0.000 description 6
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 6
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- 235000020778 linoleic acid Nutrition 0.000 description 6
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- AFPLNGZPBSKHHQ-MEGGAXOGSA-N solanesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO AFPLNGZPBSKHHQ-MEGGAXOGSA-N 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000001814 pectin Substances 0.000 description 5
- 235000010987 pectin Nutrition 0.000 description 5
- 229920001277 pectin Polymers 0.000 description 5
- 239000001307 helium Substances 0.000 description 4
- 229910052734 helium Inorganic materials 0.000 description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N 2,3,4,5-tetrahydroxypentanal Chemical compound OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 229920001221 xylan Polymers 0.000 description 2
- 150000004823 xylans Chemical class 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- GSSXLFACIJSBOM-UHFFFAOYSA-N 2h-pyran-2-ol Chemical compound OC1OC=CC=C1 GSSXLFACIJSBOM-UHFFFAOYSA-N 0.000 description 1
- 229910000809 Alumel Inorganic materials 0.000 description 1
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- 235000001014 amino acid Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229910001179 chromel Inorganic materials 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- DNHVXYDGZKWYNU-UHFFFAOYSA-N lead;hydrate Chemical compound O.[Pb] DNHVXYDGZKWYNU-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000012086 standard solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Images
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 comprises 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.
- FIG. 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).
- FIG. 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 (1 mg), linoleic acid (2 mg), linolenic acid (3.5 mg), stigmasterol (0.8 mg, chlorogenic acid (8 mg) and solanesol (15 mg) dissolved in methanol.
- PAHs polycyclic aromatic hydrocarbons
- B[a]P Benzo[a]pyrene
- a 5-ring PAH Benzo[a]pyrene
- 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 2.5 cm i.d. quartz tube placed inside a 30 cm long heated Carbolite furnace having an isothermal length of ca. 7 cm at a temperature of 600° C. Helium was used as the carrier gas at a flow rate of 120 cm 3 /min.
- the residence time of gas phase pyrolysis products in the isothermal section of the reactor was calculated to be approximately 4 s 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
- the hexane and ethyl acetate and methanol extracted samples were prepared using a Soxhlet extraction setup.
- the water extracted sample was prepared by extracting a sample of bright lamina packed in a column with a continuous stream of deionized water at room temperature. Exhaustive extraction processes in hexane, ethyl acetate, methanol and water lead to about a 4, 16, 40 and 50% reduction in sample weight, respectively.
- Oleic acid (99+%), linoleic acid (99%), stigmasterol (93%) 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. A mixture of: oleic acid (1 mg/g), linoleic acid (2 mg/g), linolenic acid (3.5 mg/g), stigmasterol (0.8 mg/g), chlorogenic acid (8 mg/g) and solanesol (15 mg/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 10 to 1000 ng/ml.
- B[a]P Yield Component (ng/g) (ng/g) Sterols Stigmasterol b ( ⁇ 0.8 mg/g) 1200 0.9 Isoprenoid Solanesol (20-40 mg/g) ND 0 Fatty Acids Oleic acid ( ⁇ 1 mg/g) 80 0.08 Linoleic acid ( ⁇ 2 mg/g) 175 0.35 Linolenic acid ( ⁇ 4 mg/g) 335 1.34 Carbohydrates Cellulose ( ⁇ 100 mg/g) 970 60 Hemicellulose ( ⁇ 100 mg/g) 976 60 Pectin ( ⁇ 100 mg/g) 100 10 Glucose ( ⁇ 140 mg/g) 786 98 Polyphenols Lignin ( ⁇ 40 mg/g) 934 18 Chlorogenic acid ( ⁇ 8 mg/g) ND 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 (1 mg/g), linoleic acid (2 mg/g), linolenic acid (3.5 mg/g), stigmasterol (0.8 mg/g), chlorogenic acid (8 mg/g) and solanesol (15 mg/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.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/289,314 US20060162733A1 (en) | 2004-12-01 | 2005-11-30 | Process of reducing generation of benzo[a]pyrene during smoking |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63198404P | 2004-12-01 | 2004-12-01 | |
| US11/289,314 US20060162733A1 (en) | 2004-12-01 | 2005-11-30 | Process of reducing generation of benzo[a]pyrene during smoking |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20060162733A1 true US20060162733A1 (en) | 2006-07-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/289,314 Abandoned US20060162733A1 (en) | 2004-12-01 | 2005-11-30 | Process of reducing generation of benzo[a]pyrene during smoking |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US20060162733A1 (fr) |
| WO (1) | WO2006059229A1 (fr) |
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| US20070141739A1 (en) * | 2005-10-24 | 2007-06-21 | 3M Innovative Properties Company | Method of making light emitting device having a molded encapsulant |
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| WO2006059229A1 (fr) | 2006-06-08 |
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