US3095882A - Tobacco flavorants - Google Patents

Tobacco flavorants Download PDF

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Publication number
US3095882A
US3095882A US129240A US12924061A US3095882A US 3095882 A US3095882 A US 3095882A US 129240 A US129240 A US 129240A US 12924061 A US12924061 A US 12924061A US 3095882 A US3095882 A US 3095882A
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United States
Prior art keywords
tobacco
product
alcohol
flavorants
flask
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Expired - Lifetime
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US129240A
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English (en)
Inventor
John D Hind
Frank H Crayton
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Philip Morris USA Inc
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Philip Morris USA Inc
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Application filed by Philip Morris USA Inc filed Critical Philip Morris USA Inc
Priority to US129240A priority Critical patent/US3095882A/en
Priority to DE19621517303 priority patent/DE1517303A1/de
Priority to GB29883/62A priority patent/GB951566A/en
Priority to CH933062A priority patent/CH459855A/de
Application granted granted Critical
Publication of US3095882A publication Critical patent/US3095882A/en
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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
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • 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
    • A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/305—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances of undetermined constitution characterised by their preparation

Definitions

  • This invention relates to flavorants suitable for incorporation in tobacco and tobacco products. More particularly it relates to volatile flavorants which contribute to package aroma of tobacco products and/or to the flavor of the tobacco product upon its being smoked.
  • a particularly sought after object in the tobacco preparation art is to enhance the sweetness of tobacco poducts. This has been attempted by addition to the tobacco of raw sugars, either as such or in the form of materials rich in sugars, e.g., molasses. Such materials, while altering the flavor of the tobacco product, are unsatisfactory in that their burning characteristics are markedly different from those of tobacco. Particularly where moderate or higher levels of sweetness are desired, either for their own flavor values or to complement other additives or flavors incorporated in the tobacco, it is found that loading the tobacco with substantial quantities of such sugars interferes with its combustion to an unacceptable extent.
  • sweetening agents particularly well adapted for incorporation in tobacco products may be prepared from substances native to tobacco leaf.
  • such derivatives Whether prepared from tobacco itself or synthetically, contribute the desired sweetness, yet do not interfere with combustion of the tobacco product.
  • sweetening agents and other flavorants are provided which do not interfere with the combustion of the tobacco product even when such agents are present in relatively high quantity.
  • the flavorants of this invention are all volatile, by which is meant that they vaporize at a temperature below the pyrolysis temperature of tobacco and distill oif ahead of the coal, little if any of such materials being consumed by combustion.
  • a further advantage of the present invention is that novel and useful subtle flavorants are provided for incorporation in tobacco in whatever combination or ratio may be desired.
  • desirable and useful flavorants for incorporation in tobacco products which flavorants are characterized by volatility and by a sweet flavor
  • Other desirable and useful products 3,095,882 Patented July 2., 1963 "ice which contribute desirable and characteristic odors to the tobacco product before and during smoking are de rived by alcoholysis of organic acids or mixtures thereof, and particularly by alcoholysis of organic acids which are native to tobacco, to provide products which volatilize below the pyrolysis temperature of tobacco.
  • the flavorful products may be incorporated in tobacco individually, with or without other commonly used flavors, humectants and other familiar additives, or they may be selectively combined and blended in appropriate proportion to provide dilfering subtle and pleasing characteristics to pack aroma and smoke.
  • the alcohols which may suitably be used in the prac tice of the present invention include the lower alkyl alcohols, i.e., those having from 1-6 carbon atoms.
  • Other suitable alcohols may be determined by simple trial, the criterion being that the product be volatile below the pyrolysis temperature of tobacco and that the product have desirable characteristics of flavor and/or aroma.
  • saccharides may be used in the practice of this invention and include, without limitation, the monosaccharides, idisaccharides, trisaco'harides, tetrasaccharides and polysaccharides, so long as their reaction products with alcohol are volatile and pleasing, as above discussed.
  • the monosaocharides, disaccharides and polysaccharides are generally preferred, and especially the hexoses, pent-oses, dihexoses, such as sucrose, and polyhexoses, such as dextrins, starches, and fructosans.
  • the organic acids which may be rused to advantage are those which in reaction with the alcohol or mixture of alcohols employed 'will yield volatile prodnets of desirable characteristics.
  • the preferred organic acids are those naturally occurring in tobacco, including the aliphatic polycarboxylic acids, particularly the alipliatic diand tri-carboxylic and hydroxycarboxylic acids, and include, without limitation, malonic acid, malic acid, succinic acid, tartaric acid and citric acid.
  • Desirable flavorants include lower alkyl malates, lower alkyl mal onates, lower alkyl succinates, lower alkyl tartrates and lower alkyl citrates.
  • Desirable flavorants contributing a sweet flavor or aroma include, without limitation, (lower alkyl) oxymethyl furfurals and lower alkyl levnlinates.
  • the amount of flavorant incorporated in tobacco in accordance with this invention is largely a matter of choice. As a minimum, an effective amount should be incorporated to contribute a discrete aroma and/ or flavor to the product or to its smoke. Any larger amounts depend upon the character and extent of enhancement de sired, and we have found that their effect is more pleasing when subtle. We have found further, that the flavorants of this invention tend to complement each other and commonly used flavor additives and that by' varying proportions and amounts within the skill of the formulator, unusual pleasing and desirable effects can be achieved.
  • the flavorants may be incorporated in tobacco by spraying, dipping, or other conventional means.
  • Example 1 3500 ml. of absolute methanol and 138.5 m1. of concentrated aqueous hydrochloric acid are placed in a 5- liter trident flask and heated to 40 C. 400 g. of sucrose fruity odor. The second fraction is substantially methoxymethyl furfural and has an odor suggestive of maraschino cherries. The over-all yield is 25 .3
  • Example 2 15 liters of anhydrous ethanol, 457 ml. of concentrated HCl and 2000 g. of sucrose are placed in a S-gallon carboy, which is shaken occasionally and then left to stand overnight. In the morning the carboy is placed in a constant temperature bath for three hours at 50 C. with continuous stirring to insure that all sugar is in solution. The bath is then brough to 75 C. and the carboy contents are held at that temperature for 24 hours. The mixture is thereafter cooled and neutralized with 391 ml. of 41% NaOH to pH 6.5. V
  • the reaction mass is vacuum distilled under continuous water aspirator vacuum to remove excess alcohol.
  • the syrupy residue is ether-extracted in two batches in a continuous liquid-liquid extractor with ethyl ether, and the ether is removed by heating gently at atmospheric pressure.
  • the two batches of extracted material are vacuum distilled at 1-2 mm. of mercury to produce four fractions for batch #1 and three fractions for batch #2.
  • Fractions I and IV of batch #1 and Fractions 1 and iii of batch #2 are identified as ethyl levulinate (B.P. 51-64 C. at 2. mm. Hg) and etlioxymethyl furiural, respectively, by gas chromotography.
  • the intermediate fractions are mixtures of the two.
  • the yield of ethyl levulinate is 6.25 that of ethoxymethylfurfural is 9.0%; total yield is 23.5%
  • Example 3 12 ml. of concentrated aqueous hydrochloric acid and 500 ml. of n-propyl alcohol are placed in a one-liter trident flask equipped with an air-driven stirrer and a fractionating column. The flask contents are brought to 60 C. with a Glas-col mantle and 50 g. sucrose is sifted into the flask with continuous stirring. The sugar dissolves in about 14 hours. The reaction isa'ccompanied by color changes from clear and colorless to yellow, to orange, to red, and finally to black.
  • the solution is then distilled at an overhead temperature range of 87 C. to 97 C., yielding about200 ml. of distillate, principally the azeotrope of water and npropanol.
  • the odor of the product indicates that esteriiicatio'n has taken place.
  • the distillation range of the product corresponds to the boiling points of n-propyl levulinate and n-propoxymethyl furfural,
  • Example 5 V 50 g. of sucrose, 500 ml. of iso-butyl alcohol and 12 ml. of concentrated aqueous hydrochloric acid are reacted according to the procedure of Example 3. A 17.45% yield is obtained.
  • the products are identified by their distillation points as iso-butyl levulinate and iso-butoxymethyl furfural. Their odor is stronger and more distinct than that of the products prepared frornlower members of the alkyl alcohol series.
  • Example 6 50 g. of sucrose and 500 ml. of n-butyl alcohol are placed in a one-liter trident flask equipped with an airdriven stirrer and a fractionating column. The tempera ture is raised gradually to 60 C. with a Glas-col mantle. The mixture is stirred for 3 hours and then allowed to stand over the Weekend. The temperature is again brought to 60 C. for 1 hour with stirring, additional water being added to bring undissolved sugar into solution. 12 ml. of concentrated hydrochloric acid is then added.
  • Example 3 The procedures of Example 3 are followed to remove the product, the yield being 16.1%.
  • the products are vacuum distilled and identified by their distillation points as n-butyl levulinate and n-butoxymethyl furfural.
  • the n-butyl levulinate has a woody, ethereal odor that is rather sharp.
  • the n-butyoxymethyl furfural has a sweet but woody odor.
  • Example 7 10 g. of sucrose, m1. of n-hexanol and 0.5 ml. of concentrated hydrochloric acid are placed in a pressure bottle.
  • the bottle is stoppered and partially immersed in a constant-temperature water bath.
  • the reactants are maintained at 77 C. for 72 hoursand at 84 C. for 24 hours, whereupon the bath is allowed to cool with the bottle still immersed.
  • Example 8 To a pressure bottle are added 5 g. sucrose, 10 g. potassium acid sulfate (KHSO and 100 ml. of neutral ethyl alcohol. The bottle is loosely stoppered and immersed in a 70 water bath for 2 hours, being shaken occasionally during this time.
  • sucrose sucrose
  • 10 g. potassium acid sulfate KHSO
  • 100 ml. of neutral ethyl alcohol 100 ml.
  • reaction bottle is then placed in a 60 C. forced draft oven and heated for 16 hours. On removal from the oven, the contents are light yellow in color and have a very pleasant odor, quite difierent from alcohol, which indicates the predicted reaction has taken place.
  • a test panel identifies these odor notesrin the sample: apple, fruit aroma and coconut.
  • Example 9 Three Erlenmeyer flasks are prepared, each containing 300 g. of dried bright tobacco stems (ca. 8% reducing sugar) covered with 700 ml. of anhydrous ethanol.
  • the alcohol in flask #1 is acidified with 58 ml. of HCl, that in flask #2 with a mixture of 29 ml. HCl and ml. of concentrated H 80 and the third with 20 ml. concentrated H 80 All three flasks contain the same stoichiometric acid equivalents.
  • the flasks are placed in a water bath at 75 C. for hours and their contents are then neutralized. Samples are taken and diluted. Flavor and aroma are found to be most preferred in the H SO -catalyzed product, followed by the mixed acid product, and the HCl-catalyzed product is rated third.
  • Example 10 100 g. starch (dry Wt.) and 500 ml. of ethanol containing 7% HCl are added to a one-liter flask and refluxed 5 hours. Vacuum distillation of the reaction product gives 11 g. of ethyl levulinate and 3.9 g. of ethoxymethyl furfural.
  • Example 11 To a flask are added 5 g. of molasses, 200 rnl. anhydrous ethanol and 7.3 ml. concentrated H 80 The reactants are heated for 18 hours at 75 C. Flavor notes indicate that reaction of the character heretofore described has taken place.
  • Example 12 To a flask is added 5 g. fructose, 150 ml. SD #30 alcohol (ethanol containing about 10% methanol and 7.3 ml. of concentrated H 50 The flask contents are reacted for 96 hours, at elevated temperatures between 50 C. and 70 C. A sample is diluted with an equal volume of Water and neutralized with NaOH to pH 6.5. A sweet odor, very similar to the odor produced by the same reaction With bright stems, is found and can be detected even when the reaction mixture is diluted to 1:2000.
  • Example 13 To a one-liter flask are added 40 g. of DL malic acid, 1000 ml. of anhydrous ethanol and 70 ml. of acidic alcohol (16.2 g. HCl/ 100 ml. of ethanol). The flask is connected to upward air and downward water condensers and the contents are heated for 6 hours and 43 minutes, during which time 474 ml. of alcohol are removed. The flask contents are then neutralized to pH 7.0 with 41% NaOH. A 40.04 g. (73%) yield of the distillate of the expected boiling point is obtained when the residue is vacuum distilled at 2.5 of mercury. The product is identified as diethyl malate by gas chromatography.
  • Esters of other acids may be prepared by the procedure of Example 13. Illustratively, by employing n-butanol and succinic acid there is obtained di-n-butyl succinate, which has an odor note of butyric acid, sweet, and with relatively low overall intensity.
  • Example 15 A five-gallon Pyrex carboy is loaded with 12.5 pounds of tobacco (dried bright stems) and covered with 12 liters of ethanol mixed with 1000 ml. of concentrated hydrochloric acid. The carboy and contents are maintained at a constant temperature of 68 C. for 17 /2 hours. The temperature is then raised to 75 C. for 4% hours. The liquor from the carboy is recovered and diluted to 12 liters with fresh ethanol and acid in the same proportions and poured into a second carboy containing 12.5 pounds of fresh dried bright stems. The procedure is as before, with recovery of liquor and its reaction with a third carboy of stems in the same manner.
  • the separated components may be blended with tobacco singly or in desired admixture.
  • Example 16 The pleasing, distinctive and subtle attributes of exemplary flavorants in accordance with this invention when embodied in smoking products are illustrated by the present example.
  • Half the mixture comprises ethoxymethyl furfural and ethyl levulinate, prepared as in Example 2, and the other half comprises substantially equal parts of the three specified compounds, all parts being by Weight.
  • the amount of the mixture of flavorants applied to the filler is about 0.3% by weight of the filler. Amounts within the range of 0.1% to 1% have been found satisfactory, with 0.2% to 04% being preferred.
  • the treated filler is dried and made into cigarettes for evaluation of pleasing odor and taste.
  • the cigarettes so prepared and untreated control cigarettes are submitted to a panel of three judges, who use a 0-10 intensity scale in aid of evaluation.
  • the panel finds that the cigarettes containing the flavorful additives of this invention are characterized by a fruity odor in unlit draw taste and in smoke taste and are readily distinguishable from the controls.
  • the flavorants are found to enhance significantly the taste and odor of the tobacco filler. Data from the test is given below.
  • a method of enhancing the flavor and aroma of a tobacco product which comprises incorporating in said tobacco product an efiective amount of at least one flavorant which is the reaction product of an alcohol with a member of the group consisting of saccharides and aliphatic diand tri-carboxylic and hydroxycarboxylic acids, said fiavorant being characterized in being volatile below the pyrolysis temperature oftob'acco.
  • a method of enhancing the flavor and aroma of a tobacco product which comprises incorporating in said tobacco product an effective amount of a flavorant which is the reaction product of a lower alkyl alcohol and a member of the group consisting ot aliphatic diand tricarboxylic and hydroxycarboxylic acids, said fiavorant being characterized in being volatile below the pyrolysis temperature of tobacco.
  • Amethod of providing a sweet flavor in the smoke of a tobacco product which comprises incorporating in said tobacco product an'effective amount of the reaction product of an alcohol and a saccharide, said reaction product being characterized in being volatile below the pyrolysis temperature of tobacco.
  • a method of providing a sweet flavor in the smoke of a tobacco product which comprises incorporating in said tobacco product an effective amount of the reaction product of at least one lower alkyl alcohol and at least one member of the group consisting of hexoses, pentoses, dihexoses, dextrins, starches and fructosans, said reaction product being characterized in being volatile below the pyrolysis temperature of tobacco.

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Fats And Perfumes (AREA)
US129240A 1961-08-04 1961-08-04 Tobacco flavorants Expired - Lifetime US3095882A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US129240A US3095882A (en) 1961-08-04 1961-08-04 Tobacco flavorants
DE19621517303 DE1517303A1 (de) 1961-08-04 1962-07-31 Tabakprodukt und Verfahren zu seiner Herstellung
GB29883/62A GB951566A (en) 1961-08-04 1962-08-03 Tobacco product
CH933062A CH459855A (de) 1961-08-04 1962-08-03 Verfahren zur Verbesserung des Aromas eines Tabakproduktes

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US129240A US3095882A (en) 1961-08-04 1961-08-04 Tobacco flavorants

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GB (1) GB951566A (de)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3332428A (en) * 1964-10-01 1967-07-25 Liggett & Myers Tobacco Co Tobacco incorporating carbonate esters of flavorants
US3750674A (en) * 1972-08-07 1973-08-07 Reynolds Tobacco Co R Tobacco product
US3854485A (en) * 1973-09-24 1974-12-17 Liggett & Myers Inc Tobacco compositions comprising mono-esters of mono- and dialkylmalonates
US4830028A (en) * 1987-02-10 1989-05-16 R. J. Reynolds Tobacco Company Salts provided from nicotine and organic acid as cigarette additives
US5099862A (en) * 1990-04-05 1992-03-31 R. J. Reynolds Tobacco Company Tobacco extraction process
US5197494A (en) * 1991-06-04 1993-03-30 R.J. Reynolds Tobacco Company Tobacco extraction process
US5413122A (en) * 1992-02-18 1995-05-09 R. J. Reynolds Tobacco Company Method of providing flavorful and aromatic compounds
JP2009529550A (ja) * 2006-03-10 2009-08-20 フラニックス テクノロジーズ ベスローテン フェンノートシャップ ５−アルコキシメチルフルフラルエーテルの合成方法及びそれらの使用
US20100113460A1 (en) * 2007-03-28 2010-05-06 Givaudan Sa Organic Compounds
JP2010538033A (ja) * 2007-09-07 2010-12-09 フラニックス テクノロジーズ ベスローテン フェンノートシャップ 糖及びアルコール由来のフルフラールと５−（アルコキシメチル）フルフラール誘導体との混合物
US20110232655A1 (en) * 2010-03-26 2011-09-29 Philip Morris Usa Inc. Smoking article including alkanoylated glycoside and method of making
CN107637859A (zh) * 2017-10-24 2018-01-30 湖北中烟工业有限责任公司 一种用于烟草加料的混合酸及其制备方法和应用
JPWO2017018110A1 (ja) * 2015-07-24 2018-02-08 日本たばこ産業株式会社 組成物
US10301275B2 (en) 2017-03-17 2019-05-28 Altria Client Services Llc Sweet taste modulators
CN113109483A (zh) * 2021-05-07 2021-07-13 上海烟草集团有限责任公司 一种烟用潜香型香原料热解香气成分的分析方法
CN115005494A (zh) * 2022-06-30 2022-09-06 河南中烟工业有限责任公司 一种降低糖类化合物裂解温度的方法与应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766145A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US2766146A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US2766150A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766145A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US2766146A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US2766150A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3332428A (en) * 1964-10-01 1967-07-25 Liggett & Myers Tobacco Co Tobacco incorporating carbonate esters of flavorants
US3750674A (en) * 1972-08-07 1973-08-07 Reynolds Tobacco Co R Tobacco product
US3854485A (en) * 1973-09-24 1974-12-17 Liggett & Myers Inc Tobacco compositions comprising mono-esters of mono- and dialkylmalonates
US4830028A (en) * 1987-02-10 1989-05-16 R. J. Reynolds Tobacco Company Salts provided from nicotine and organic acid as cigarette additives
US4836224A (en) * 1987-02-10 1989-06-06 R. J. Reynolds Tobacco Company Cigarette
US5099862A (en) * 1990-04-05 1992-03-31 R. J. Reynolds Tobacco Company Tobacco extraction process
US5197494A (en) * 1991-06-04 1993-03-30 R.J. Reynolds Tobacco Company Tobacco extraction process
US5413122A (en) * 1992-02-18 1995-05-09 R. J. Reynolds Tobacco Company Method of providing flavorful and aromatic compounds
JP2009529550A (ja) * 2006-03-10 2009-08-20 フラニックス テクノロジーズ ベスローテン フェンノートシャップ ５−アルコキシメチルフルフラルエーテルの合成方法及びそれらの使用
US20100113460A1 (en) * 2007-03-28 2010-05-06 Givaudan Sa Organic Compounds
JP2010538033A (ja) * 2007-09-07 2010-12-09 フラニックス テクノロジーズ ベスローテン フェンノートシャップ 糖及びアルコール由来のフルフラールと５−（アルコキシメチル）フルフラール誘導体との混合物
US20110232655A1 (en) * 2010-03-26 2011-09-29 Philip Morris Usa Inc. Smoking article including alkanoylated glycoside and method of making
US9034106B2 (en) 2010-03-26 2015-05-19 Philip Morris Usa Inc. Smoking article including alkanoylated glycoside
US10226067B2 (en) 2010-03-26 2019-03-12 Philip Morris Usa Inc. Smoking article including alkanoylated glycoside and method of making
JPWO2017018110A1 (ja) * 2015-07-24 2018-02-08 日本たばこ産業株式会社 組成物
EP3315031A4 (de) * 2015-07-24 2019-02-27 Japan Tobacco, Inc. Zusammensetzung
US10301275B2 (en) 2017-03-17 2019-05-28 Altria Client Services Llc Sweet taste modulators
CN107637859A (zh) * 2017-10-24 2018-01-30 湖北中烟工业有限责任公司 一种用于烟草加料的混合酸及其制备方法和应用
CN113109483A (zh) * 2021-05-07 2021-07-13 上海烟草集团有限责任公司 一种烟用潜香型香原料热解香气成分的分析方法
CN113109483B (zh) * 2021-05-07 2023-05-16 上海烟草集团有限责任公司 一种烟用潜香型香原料热解香气成分的分析方法
CN115005494A (zh) * 2022-06-30 2022-09-06 河南中烟工业有限责任公司 一种降低糖类化合物裂解温度的方法与应用

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CH459855A (de) 1968-07-15
GB951566A (en) 1964-03-04
DE1517303A1 (de) 1969-09-11

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