US3610253A - Treating tobacco - Google Patents
Treating tobacco Download PDFInfo
- Publication number
- US3610253A US3610253A US801155A US3610253DA US3610253A US 3610253 A US3610253 A US 3610253A US 801155 A US801155 A US 801155A US 3610253D A US3610253D A US 3610253DA US 3610253 A US3610253 A US 3610253A
- Authority
- US
- United States
- Prior art keywords
- tobacco
- accordance
- flavorant
- percent
- product
- 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.)
- Expired - Lifetime
Links
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 67
- 241000208125 Nicotiana Species 0.000 title claims abstract description 66
- 239000000796 flavoring agent Substances 0.000 claims abstract description 26
- 235000019634 flavors Nutrition 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 230000000391 smoking effect Effects 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical group CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 2
- 235000019505 tobacco product Nutrition 0.000 claims description 2
- AXGOOCLYBPQWNG-UHFFFAOYSA-N 3-ethylfuran-2,5-dione Chemical group CCC1=CC(=O)OC1=O AXGOOCLYBPQWNG-UHFFFAOYSA-N 0.000 claims 1
- 239000000779 smoke Substances 0.000 abstract description 12
- -1 and R2 -H Chemical group 0.000 abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- 235000019504 cigarettes Nutrition 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 9
- 239000000284 extract Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- CUBICSJJYOPOIA-UHFFFAOYSA-N Ethylmethylmaleimide Chemical compound CCC1=C(C)C(=O)NC1=O CUBICSJJYOPOIA-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
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
- A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
Definitions
- the invention is more particularly concerned with natural tobaccos, it can also be applied to synthetic or artificial tobacco foil.
- the invention can be applied to natural tobaccos lacking in aroma or tobaccos which are neutral in flavor.
- the invention may be applied to substances to be smoked which are not of a tobacco nature, for example medicinal cigarettes or to cigarettes or to cigarette filter materials.
- tobacco for example medicinal cigarettes or to cigarettes or to cigarette filter materials.
- the aim of this method was exclusively the production of a synthetic tobacco which was free of woody and cellulosic tobacco constituents. There was no intentionto bring about a systematic and predictable flavoring of a given natural tobacco or natural tobacco mixture.
- One object of the present invention is to overcome these difficulties occurring with prior art methods.
- a further aim of the invention is to enrich the smoke aroma of tobaccos which have a poor aroma.
- a further object of the invention is to provide a method of compounding a cigarette tobacco mixture in which, without any impairment of the smoke quality occurring, some expen' sive components are omitted and replaced by chemically prepared substances or by extracts.
- Substances in accordance with the above general formula can be added singly or in admixture in any convenientmanner to tobacco or part of a tobacco mixtureuFor instance the quantity added can be within the range of 0.00l to L0 percent by weight of the tobacco, the preferred range being 0.0l to 0.1 percent.
- Application can for example be by dipping the tobacco in solutions of the substituted pyrrols in suitable highly volatile solvents. Application can also be carried out by spraying on such solutions.
- the application can be at any suitable stage in the tobacco manufacturing process, for example in the case of cigarette production. it has been found convenient to spray on an 1-5 percent W/V- ethanolic solution of the substance or substances onto cut tobacco before it is passed into a cigarette making machine.
- the substances to be used in the method in accordance with the invention can be readily synthesized in accordance with the method of V. R. Skvarchenko (C. A. 45l8d l958)).
- a-ethylacetoacetic ester can be converted into methylethyl malomitrile as the bisulfite compound using sodium cyanide.
- methylethyl maleic anhydride can be obtained by saponification and dry distillation.
- the maleic anhydride can be converted readily into methylethyl maleimide by heating with urea.
- the steps in the reaction can be shown as follows:
- the tobacco mixture for cigarettes free of any aroma materials such as essential oils was sprayed with a 2.5 percent V/W solution of the substance in question in ethanol.
- the tobacco was then held fora week at 20 C. and 67 percent relative humidity and then made into cigarettes.
- the cigarettes so produced were then tested by a panel of experts so as to make a comparison with untreated tobacco mixture as regards flavor.
- the quantity of solution applied to the tobacco mixture was so chosen that the cigarettes of treated tobacco contained 0.001 percent by weight (or 0.0l percent in the tobacco smoke condensate) more Z-formylpyrrol (as regards the main smoke stream) than was the case with cigarettes of the same but untreated tobacco mixture for purposes of comparison.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Manufacture Of Tobacco Products (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681692949 DE1692949A1 (de) | 1967-02-25 | 1968-02-23 | Verfahren zur geschmacklichen Beeinflussung von Tabakrauch |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3610253A true US3610253A (en) | 1971-10-05 |
Family
ID=5687709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US801155A Expired - Lifetime US3610253A (en) | 1968-02-23 | 1969-02-20 | Treating tobacco |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3610253A (en)) |
| BE (1) | BE728744A (en)) |
| CH (1) | CH519863A (en)) |
| DK (1) | DK125725B (en)) |
| FR (1) | FR2002536A1 (en)) |
| GB (1) | GB1248312A (en)) |
| LU (1) | LU58061A1 (en)) |
| NL (1) | NL6902702A (en)) |
| NO (1) | NO119071B (en)) |
| SE (1) | SE354408B (en)) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047433A (en) * | 1961-10-19 | 1962-07-31 | Philip Morris Inc | Use of diels-alder adducts as tobacco additives |
-
1969
- 1969-02-13 CH CH214669A patent/CH519863A/de not_active IP Right Cessation
- 1969-02-18 GB GB8633/69A patent/GB1248312A/en not_active Expired
- 1969-02-20 US US801155A patent/US3610253A/en not_active Expired - Lifetime
- 1969-02-20 NL NL6902702A patent/NL6902702A/xx unknown
- 1969-02-21 SE SE02469/69A patent/SE354408B/xx unknown
- 1969-02-21 LU LU58061D patent/LU58061A1/xx unknown
- 1969-02-21 DK DK97469AA patent/DK125725B/da unknown
- 1969-02-21 BE BE728744D patent/BE728744A/xx unknown
- 1969-02-21 FR FR6904586A patent/FR2002536A1/fr not_active Withdrawn
- 1969-02-21 NO NO0710/69A patent/NO119071B/no unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047433A (en) * | 1961-10-19 | 1962-07-31 | Philip Morris Inc | Use of diels-alder adducts as tobacco additives |
Non-Patent Citations (1)
| Title |
|---|
| The Merck Index, (pub.) Eighth Edition 1968, published by the Merck & Co., Rahway, N.J., U.S.A., p. 639 & 640 cited * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2002536A1 (en)) | 1969-10-17 |
| BE728744A (en)) | 1969-08-01 |
| NO119071B (en)) | 1970-03-16 |
| GB1248312A (en) | 1971-09-29 |
| NL6902702A (en)) | 1969-08-26 |
| LU58061A1 (en)) | 1969-06-03 |
| CH519863A (de) | 1972-03-15 |
| SE354408B (en)) | 1973-03-12 |
| DK125725B (da) | 1973-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2059377C1 (ru) | Курительная смесь | |
| US2770239A (en) | Process of treating tobacco | |
| US5326563A (en) | Nicotine compositions | |
| Frankenburg | Chemical changes in the harvested tobacco leaf | |
| RU2031608C1 (ru) | Композиция для ароматизации курительного табака | |
| CN110833207B (zh) | 晾晒烟风格转化方法 | |
| US3096773A (en) | Process for treating tobacco and tobacco obtained by said process | |
| US3447539A (en) | Oxidized cellulose smokable product including ashing ingredient | |
| US3610253A (en) | Treating tobacco | |
| US3840023A (en) | Flavored tobacco composition | |
| US3920027A (en) | Flavored tobacco product | |
| US2460285A (en) | Tobacco products and method of making them | |
| US3903900A (en) | Tobacco articles and compositions containing 1,2-cyclohexanedione and methods for producing same | |
| DE2458639C3 (de) | Tabakprodukte mit einem Gehalt an geschmack- oder aromaveränderndem Zusatz | |
| US3782391A (en) | {62 -methylvaleric acid alkyl esters as tobacco flavorants | |
| US3559656A (en) | Tobacco product | |
| KR20010057598A (ko) | 길초근 추출물을 함유하는 담배 가향료 및 그 제조방법 | |
| US3651815A (en) | Smokable products and a process for their production | |
| JPS59183680A (ja) | たばこ香喫味の改善方法 | |
| US3082125A (en) | Process for improving the flavor and aroma of tobacco and product | |
| US3651816A (en) | Treating tobacco | |
| US3342186A (en) | Aromatized tobaccos | |
| US3372699A (en) | Tobacco | |
| US2872360A (en) | Tobacco | |
| CN109602063A (zh) | 一种酸性改性剂及其在低温卷烟用烟草薄片中的应用方法 |