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US3111127A - Smoking tobacco product and method of making the same - Google Patents

Smoking tobacco product and method of making the same Download PDF

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Publication number
US3111127A
US3111127A US119779A US11977961A US3111127A US 3111127 A US3111127 A US 3111127A US 119779 A US119779 A US 119779A US 11977961 A US11977961 A US 11977961A US 3111127 A US3111127 A US 3111127A
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mono
tobacco
smoking
menthyl
acid
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US119779A
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Charles H Jarboe
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Brown and Williamson Holdings Inc
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Brown and Williamson Tobacco Corp
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Priority to US119779A priority Critical patent/US3111127A/en
Priority to GB20449/62A priority patent/GB939576A/en
Priority to DK284462AA priority patent/DK116713B/en
Priority to CH765662A priority patent/CH458169A/en
Priority to BE619401A priority patent/BE619401A/en
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Publication of US3111127A publication Critical patent/US3111127A/en
Priority to CY29364A priority patent/CY293A/en
Priority to MY1964103A priority patent/MY6400103A/en
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    • 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
    • A24B15/301—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by 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
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances

Definitions

  • My invention contemplates incorporating in smoking tobacco or in a smoking tobacco product a mono ester of synthetic or natural menthol and a saturated or unsaturated aliphatic or aromatic or heteroaromatic polycarboxylic acid or a substituted analogue of such an acid.
  • saturated or unsaturated aliphatic mono menthyl esters I prefer employing as acid components compounds with two carboxyl groups in the cis arrangement on adjacent carbon atoms or substituted 1, 3 in relation to one another.
  • the l, 3 substitution includes only the homo dicarboxylates such as homophthalic acid and .homoquinolinic acid.
  • polycarboxylic acids which may be used as the acid components of the ester are butanedioic (succinic) acid; cis-butenedioic (maleic) acid; pentanedioic (glutaric) acid; cis-pentenedioc (glutaconic) acid; phthalic acid; campho-ric acid; cis-cyclohexene-LZ- dicarboxylic acid; cis-4-cyclohexene-l,2-dicarboxylic acid; homophthalic acid; homoquinolinic acid; 2,3-dimethylsuccinic acid; 2,2-dimethylsuccinic acid; 1,2,3-benzenetricarboxylic acid (hemirnellitic acid); methylsuccinic acid; itaco-nic acid; aconitic acid; cis-cyclopropane-l,Z-dicarboxylate; malic acid.
  • menthol component I may employ l-menthol, dmenthol and racernatic menthol.
  • Specific examples of "ice the mono menthyl esters of polycarboxylic acids which may be used as tobacco pnoducts additives in accordance with my invention are mono menthylmaleate, mono menthylsuccinate; mono menthylphthalate; mono langethyl-Z- methyl-maleate; mono menthyl-3-methylmaleate; a-menthylcamphorate; cis mono-menthylcyclohexene-1,2-dicarboxylate; cis-1-meuthyl-4-cyclohexene-1,2-dicarboxylate; nronornenthylhomophthalate; mono menthylhomoquinolate; mono men thyl-mesodimethylsuccinate; mono menthyl 04,04 dimethy-lsuccinate; 2 menthylhemimellitate; mono menthy
  • R is the menthyl radical and R is a mate-rial selected from the group consisting of saturated and on saturated aliphatic and aromatic and heteroaromatic polycarboxylic acid radicals and substituted analogues thereof and n is the total number of carboxyl groups in the acid from which the ester is derived.
  • the mono menthyl esters may be prepared in any desired fashion.
  • the dicarboxylic acid anhydride may be reacted directly with menthol and the mono menthyl ester can then be recrystallized from a suit-able solvent.
  • menthol may be added as a suspension to an aqueous solution of the polycarboxylic acid and after heating and thereafter cooling the resultant crystals are filtered from the suspension and washed and dried.
  • Example I Twenty grams of maleic anhydride are melted in a 50 cc. three-neck flask kept at C. with a water bath. To the continuously stirred maleic anhydride, 31.2 grams of menthol are slowly added and the mixture is allowed to react at 80 C. for eight hours. At this stage, the reaction mixture has a melting point of approximately 70 C. The mono menthylmaloate can be separated from the mixture by cooling it and recrystallizing it from a suitable solvent such as the mixture commercially known as Ske-llysolve B, which is essentially n-hexane. Approximately 44 grams (approximately 87% of the reaction materials) of mono menthylmaleate is obtained having a melting point between 83-85 C.
  • Example 11 Approximately 16 grams of menthol are dissolved in 20 milliliters of anhydrous toluene. This mixture is added dropwise, over a period of 1 hour, to a stirred and refluxing solution of approximately 10 grams maleic an hydride in 25 milliliters of anhydrous toluene containing 0.01 gram of p-tol-uenesulfonic acid. After 12 hours at reflux the mixture is cooled to room temperature and extracted with milliliters of distilled Water to remove 3 the p-toluene sulfonic acid and any unreacted maleic anhydride. The toluene is removed by flash evaporation at room temperature and the product recrystallized as above, yielding 16.1 g. (67.8%) of mono menthylmaleate, It'll. 83-85 C.
  • Example III Approximately 392 g. of diamenthylmaleate are dissolved in 500 milliliters of p-dioxane and brought to 100 C. on a steam bath. To this stirred solution is added, over a three-hour period, approximately 40 grams of sodium hydroxide dissolved in 200 milliliters of water. After an additional six hours the reaction mixture is diluted with 1 liter of Water, cooled to C. and filtered to remove the menthol formed on hydrolysis. The supernatant liquid is acidified to a pH of 2 with 12 Normal sulfuric acid, cooled to 5 C. and filtered. The semi-crystalline precipitate of mono .menthylmaleate is recrystallized as above, yielding approximately 200 grams (78.9%) of mono menthylmaleate, MP. 8485 C.
  • Example I V Approximately 15.6 grams of menthol were dissolved in milliliters of anhydrous chloroform and added dropwise, over a three-hour period, to a stirred refluxing solution of 10 gnams of freshly prepared succinic anhydride in milliliters of anhydrous chloroform. On cooling mono me-nthylsuccinate precipitates, M1. 5 359 C. in yield (11.9 grams).
  • Example V Approximately 7.8 grams of menthol are dissolved in 20 milliliters of anhydrous toluene and added dropwise, over a thirty-minute period to a refluxing solution of 5 grams of succinic anhydride in 25 milliliters of toluene containing 0.1 gram of p-toluenesulfonic acid. The mixture was refluxed an additional 4 hours. After cooling to room temperature the mixture was extracted with three 25 milliliter fractions of Water to remove the p-toluenesul-fonic acid catalyst. The toluene was evaporated from the crude product at room temperature by flash evaporation. The mono menthylsuccinate is recrystallized from n-hexane at 20 C. producing approximately 23.6 g. or substantially quantitative yields of mono rnenthylsuccinate, Ml Sit-59 C.
  • Example VI Approximately 15.6 grams of menthol are dissolved in 20 milliliters of anhydrous xylene. This mixture is added dropwise, over a period of 1 hour to a stirred and refluxing solution of approximately 24.6 grams of 1,2,3-benzenetricarboxyllc acid (hemimellitic acid) in 25 milliliters of anhydrous commercial xylene mixture containing 0.01 gram of p-toluenesulfon ic acid. After 12 hours at reflux the mixture is cooled to room temperature and extracted with 100 milliliters of distilled Water to remove the ptoluenesulfonic acid catalyst. The xylene is removed by flash evaporation at 80 C. and the product mono menthylheinimellitate obtained as above.
  • 1,2,3-benzenetricarboxyllc acid hemimellitic acid
  • any of the other indicated polycarboxylic organic acids may be substituted for the acids indicated in the examples and the proportions adjusted in accordance with the molecular weight thereof.
  • the mono menthy-l esters may be incorporated in the tobacco product either alone or in mixture with each other or mixed with menthol.
  • the proportion of the mono menthy-l ester incorporated in the tobacco product may be widely varied in accordance with taste, but I have found that satisfactory results are obtained if the proportion by weight on a dry basis is between 0.01 and 1.0% of the mono ester to the smoking tobacco. Where menthol is mixed with the ester, the proportion by weight on a dry basis may be reduced to as little as 0.005% of the combined ester and menthol to the smoking tobacco.
  • any convenient method for incorporating re mono rnenthyl ester in the tobacco product may be employed.
  • the ester may be dissolved in a suitable solvent and either sprayed on the cured, cased and blended tobacco or the tobacco dipped therein.
  • an aqueous suspension of the mono ester may be prepared which, in turn, may be sprayed on the cured, blended and cased tobacco or the tobacco dipped therein.
  • a solution or aqueous suspension of the mono menthyl ester may be applied by a suitable applicator to the paper or leaf Wrapper for the smoking product.
  • Example VII Approximately 100.5 grams of mono menthylmaleate is dissolved in 500 cc. of an absolute ethanol and the solution is sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco so treated is manufactured into cigarettes using normal factory procedures and equipment.
  • Example VIII Approximately 100.5 grams of mono menthy-lmaleate is mixed with 500 cc. of water and the resultant suspension is homogenized and sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco so treated is manufactured into cigarettes using normal factory procedures and equipment.
  • Example IX Approximately 227 grams of mono menthylm-aleate is dissolved in 1520 cc. of ethanol and the solution sprayed, in conjunction with other flavoring matter, onto 200 pounds of cured, cased, blended and shredded commercial tobacco. The tobacco mixture so treated is manufactured into cigarettes using the procedures and equipment normal to conventional manufacture.
  • Example X Approximately 276 grams of mono menthylmaleate and 57 grams of either natural or synthetic menthol is dissolved in 1520 cc. of 95% ethanol and the solution sprayed, in conjunction with other flavoring matter, onto 200 pounds of cured, cased, blended and shredded commercial tobacco. The tobacco mixture so treated is manufactured into cigarettes using the procedures and equipment normal to conventional manufacture.
  • Example XI Example XII Approximately 100.6 grams of mono menthylsuccinate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
  • Example XIII Approximately 119.5 grams of mono menthylphthalate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
  • Example XIV Approximately 136.8 grams of mono menthylhemimellitate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
  • Example XV Approximately 105.3 grams of mono menthyl-3-methylmaleate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
  • Example XVI Approximately 133.6 grams of mono me-nthylcamphorate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
  • Tobacco products made in accordance with the specific examples given herein have been evaluated and the products were observed to burn slower at smolder than a comparable control, to have increased firmness and to require more puffs under a controlled smoking regime and, when tested organoleptically, the smoking products were found to deliver smoke having a pleasing and cooling taste and aroma characteristic of menthol at an apparently increasing rate when the ester alone was used and at an apparently constant rate when menthol was mixed with the ester.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein a material selected from the group consisting of mono menthylmaleate, mono menthylsuccinate; mono menthylphthalate; mono menthyl-Z-methylmaleate; mono menthyl-3-methylmaleate; mono menthylcamphorate; cis-mono menthylcyclohexene 1,2 dicarboxylate; cis-l-menthyl-4-cyclohexene-1,2-dicarboxylate; mono menthy lhomophthalate; mono menthylhomoquinolate; mono menthyl meso dimethylsuccinate; mono menthyl-a,a-dimethylsuccinate; mono menthy-lhemimellitate; mono menthylmethylsuccinate; mono menthylaconitate; mono menthylitaconate; mono menthyl-cis-cyclopropanedicarboxylate and mono menthylmal
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylmaleate.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylsuccinate.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylphthalate.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono mentlxyl-Zmrethylmaleate.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthyi-3-methylmaleate.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylhemimellitate.
  • the method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco a material selected from the group consisting of mono menthylnialeate, mono menthylsuccinate; mono methylphthalate; mono ment-hyl-Z- methylmaleate; mono menthyl-S-methylmaleate; mono menthylcamphorate; cis mono menthylcyclohexene-1,2- dicarboxylate; cis-1-menthyl-4-cyclohexene-1,Z-dicarboxylate; mono menthylhomophthal-ate; mono menthylhomoquinolate; mono menthyl-meso-dimethylsuccinate; mono menthyl-a,a-dimenthylsuccinate; mono tmenthylhemimellitate; mono menthylmethylsuccinate; mono menthylaconitate; mono menthylitaconate; mono menthyl-cis-cyclopropanedicarbox
  • the method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthylsuccinate.
  • the method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthylphthalate.
  • the method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono-menthyl-Z-methylmaleate.
  • the method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthyl-3-methylmaleate.
  • the method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono-menthylcamphorate.
  • the method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthylhemimellitate.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein between 0.01 and 1% by weight of a mono menthyl ester of a polycarboxylic acid.
  • a smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein between 0.01 and 1% by Weight of a mono menthyl ester of a polycarboxylic acid having the formula:
  • R is the menthyl radical and R is a material selected from the group consisting of saturated and unsaturated aliphatic and aromatic and hetero-aromatic polycarboxylic acid radicals and n is the total number of carboxyl groups in the acid from which the ester is derived.
  • the method of imparting improved smoking flavor characteristics to a smoking tobacco product which comprises incoporating in smoking tobacco between 0.01 and 1% by weight of a mono menthyl ester of a polycarboxylic acid.
  • R is the menthyl radical and R is a material selected from the group consisting of saturated and un saturated aliphatic and aromatic and heteroaromatic poly- F? s. carboxylic acid radicals and n is the total number of carboxyl groups in the acid from which the ester is derived.

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  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
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Description

United States Patent 3,111,127 SMOKING TOBACCQ PRODUCT AND METHQD OF MAKING THE SAME Charles H. .larboe, Louisville, Ky., assignor to Brown Williamson Tobacco Corporation, Louisville, Ky, a corporation of Delaware No Drawing. Filed June 27, 1961, Ser. No. 119,779 19 Claims. (Cl. 131l7) This invention relates to an improved smoking tobacco product having improved smoking flavor characteristics and to the method of making the improved smoking tobacoo product.
The use of natural and synthetic menthol in smoking tobacco, particularly in cigarettes, to impart its characteristic cooling flavor and aroma thereto is of increasing significance to the tobacco products industry. Unfortunately, there are several difficulties and disadvantages associated with the use of menthol. Thus, due to its volatility, the manufacturing rooms of a tobacco products factory and also the unmentholated tobacco products are frequently contaminated by menthol and also considerable quantities of menthol are lost during the manufacturing process and the resulting menthol containing tobacco products also have a relatively short shelf life. Also, in the smoking of a menthylated tobacco product the menthol is frequently released unevenly into the smoke stream.
It is a primary object of the present invention to overcome the difficulties and disadvantages heretofore encountered and to provide an improved tobacco product and method of making the product wherein the tobacco product incorporates a menthol-containing additive imparting a desirable and pleasant cooling flavor and aroma which substantially eliminates the pnoblem of contamination of the manufacturing rooms and unrnentholated products in which the tobacco product has a protracted shelf life and in which the additive or its desirable menthol component is released into the smoke stream on smoking of the tobacco product in a satisfactory regulated manner.
My invention contemplates incorporating in smoking tobacco or in a smoking tobacco product a mono ester of synthetic or natural menthol and a saturated or unsaturated aliphatic or aromatic or heteroaromatic polycarboxylic acid or a substituted analogue of such an acid. In the case of saturated or unsaturated aliphatic mono menthyl esters I prefer employing as acid components compounds with two carboxyl groups in the cis arrangement on adjacent carbon atoms or substituted 1, 3 in relation to one another. In the case of aromatic or heteroanomatic dicarboxylic acids, the l, 3 substitution includes only the homo dicarboxylates such as homophthalic acid and .homoquinolinic acid.
Specific examples of the polycarboxylic acids which may be used as the acid components of the ester are butanedioic (succinic) acid; cis-butenedioic (maleic) acid; pentanedioic (glutaric) acid; cis-pentenedioc (glutaconic) acid; phthalic acid; campho-ric acid; cis-cyclohexene-LZ- dicarboxylic acid; cis-4-cyclohexene-l,2-dicarboxylic acid; homophthalic acid; homoquinolinic acid; 2,3-dimethylsuccinic acid; 2,2-dimethylsuccinic acid; 1,2,3-benzenetricarboxylic acid (hemirnellitic acid); methylsuccinic acid; itaco-nic acid; aconitic acid; cis-cyclopropane-l,Z-dicarboxylate; malic acid.
As the menthol component I may employ l-menthol, dmenthol and racernatic menthol. Specific examples of "ice the mono menthyl esters of polycarboxylic acids which may be used as tobacco pnoducts additives in accordance with my invention are mono menthylmaleate, mono menthylsuccinate; mono menthylphthalate; mono meuthyl-Z- methyl-maleate; mono menthyl-3-methylmaleate; a-menthylcamphorate; cis mono-menthylcyclohexene-1,2-dicarboxylate; cis-1-meuthyl-4-cyclohexene-1,2-dicarboxylate; nronornenthylhomophthalate; mono menthylhomoquinolate; mono men thyl-mesodimethylsuccinate; mono menthyl 04,04 dimethy-lsuccinate; 2 menthylhemimellitate; mono menthyl-methylsuccinate; mono menthylaoonitate; mono menthylitaconate; mono monthyl-cis-cyclopropanedicarboxylate; mono menthylmalate; cis-mono menthylglutaconate.
The mono menthyl esters that have been found to improve the flavoring characteristics when incorporated in a tobacco product may be characterized by the formula:
OOOR
oo o H) ..-1 in which R is the menthyl radical and R is a mate-rial selected from the group consisting of saturated and on saturated aliphatic and aromatic and heteroaromatic polycarboxylic acid radicals and substituted analogues thereof and n is the total number of carboxyl groups in the acid from which the ester is derived.
The mono menthyl esters may be prepared in any desired fashion. Thus, the dicarboxylic acid anhydride may be reacted directly with menthol and the mono menthyl ester can then be recrystallized from a suit-able solvent. If preferred, menthol may be added as a suspension to an aqueous solution of the polycarboxylic acid and after heating and thereafter cooling the resultant crystals are filtered from the suspension and washed and dried.
Specific examples of the preparation of a suitable mono menthyl ester of a polycarboxylic acid which may be used as a tobacco product additive in accordance with my invention are as follows:
Example I Twenty grams of maleic anhydride are melted in a 50 cc. three-neck flask kept at C. with a water bath. To the continuously stirred maleic anhydride, 31.2 grams of menthol are slowly added and the mixture is allowed to react at 80 C. for eight hours. At this stage, the reaction mixture has a melting point of approximately 70 C. The mono menthylmaloate can be separated from the mixture by cooling it and recrystallizing it from a suitable solvent such as the mixture commercially known as Ske-llysolve B, which is essentially n-hexane. Approximately 44 grams (approximately 87% of the reaction materials) of mono menthylmaleate is obtained having a melting point between 83-85 C.
Example 11 Approximately 16 grams of menthol are dissolved in 20 milliliters of anhydrous toluene. This mixture is added dropwise, over a period of 1 hour, to a stirred and refluxing solution of approximately 10 grams maleic an hydride in 25 milliliters of anhydrous toluene containing 0.01 gram of p-tol-uenesulfonic acid. After 12 hours at reflux the mixture is cooled to room temperature and extracted with milliliters of distilled Water to remove 3 the p-toluene sulfonic acid and any unreacted maleic anhydride. The toluene is removed by flash evaporation at room temperature and the product recrystallized as above, yielding 16.1 g. (67.8%) of mono menthylmaleate, It'll. 83-85 C.
Example III Approximately 392 g. of diamenthylmaleate are dissolved in 500 milliliters of p-dioxane and brought to 100 C. on a steam bath. To this stirred solution is added, over a three-hour period, approximately 40 grams of sodium hydroxide dissolved in 200 milliliters of water. After an additional six hours the reaction mixture is diluted with 1 liter of Water, cooled to C. and filtered to remove the menthol formed on hydrolysis. The supernatant liquid is acidified to a pH of 2 with 12 Normal sulfuric acid, cooled to 5 C. and filtered. The semi-crystalline precipitate of mono .menthylmaleate is recrystallized as above, yielding approximately 200 grams (78.9%) of mono menthylmaleate, MP. 8485 C.
Example I V Approximately 15.6 grams of menthol were dissolved in milliliters of anhydrous chloroform and added dropwise, over a three-hour period, to a stirred refluxing solution of 10 gnams of freshly prepared succinic anhydride in milliliters of anhydrous chloroform. On cooling mono me-nthylsuccinate precipitates, M1. 5 359 C. in yield (11.9 grams).
Example V Approximately 7.8 grams of menthol are dissolved in 20 milliliters of anhydrous toluene and added dropwise, over a thirty-minute period to a refluxing solution of 5 grams of succinic anhydride in 25 milliliters of toluene containing 0.1 gram of p-toluenesulfonic acid. The mixture was refluxed an additional 4 hours. After cooling to room temperature the mixture was extracted with three 25 milliliter fractions of Water to remove the p-toluenesul-fonic acid catalyst. The toluene was evaporated from the crude product at room temperature by flash evaporation. The mono menthylsuccinate is recrystallized from n-hexane at 20 C. producing approximately 23.6 g. or substantially quantitative yields of mono rnenthylsuccinate, Ml Sit-59 C.
Example VI Approximately 15.6 grams of menthol are dissolved in 20 milliliters of anhydrous xylene. This mixture is added dropwise, over a period of 1 hour to a stirred and refluxing solution of approximately 24.6 grams of 1,2,3-benzenetricarboxyllc acid (hemimellitic acid) in 25 milliliters of anhydrous commercial xylene mixture containing 0.01 gram of p-toluenesulfon ic acid. After 12 hours at reflux the mixture is cooled to room temperature and extracted with 100 milliliters of distilled Water to remove the ptoluenesulfonic acid catalyst. The xylene is removed by flash evaporation at 80 C. and the product mono menthylheinimellitate obtained as above.
It should be understood that in the Examples 1 to V1 set forth above any of the other indicated polycarboxylic organic acids may be substituted for the acids indicated in the examples and the proportions adjusted in accordance with the molecular weight thereof. The mono menthy-l esters may be incorporated in the tobacco product either alone or in mixture with each other or mixed with menthol. The proportion of the mono menthy-l ester incorporated in the tobacco product may be widely varied in accordance with taste, but I have found that satisfactory results are obtained if the proportion by weight on a dry basis is between 0.01 and 1.0% of the mono ester to the smoking tobacco. Where menthol is mixed with the ester, the proportion by weight on a dry basis may be reduced to as little as 0.005% of the combined ester and menthol to the smoking tobacco.
Any convenient method for incorporating re mono rnenthyl ester in the tobacco product may be employed. Thus, the ester may be dissolved in a suitable solvent and either sprayed on the cured, cased and blended tobacco or the tobacco dipped therein. Alternatively, an aqueous suspension of the mono ester may be prepared which, in turn, may be sprayed on the cured, blended and cased tobacco or the tobacco dipped therein. Under certain circumstances, a solution or aqueous suspension of the mono menthyl ester may be applied by a suitable applicator to the paper or leaf Wrapper for the smoking product.
Specific examples of methods of incorporating the mono menthyl ester in a tobacco product are as follows:
Example VII Approximately 100.5 grams of mono menthylmaleate is dissolved in 500 cc. of an absolute ethanol and the solution is sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco so treated is manufactured into cigarettes using normal factory procedures and equipment.
Example VIII Approximately 100.5 grams of mono menthy-lmaleate is mixed with 500 cc. of water and the resultant suspension is homogenized and sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco so treated is manufactured into cigarettes using normal factory procedures and equipment.
Example IX Approximately 227 grams of mono menthylm-aleate is dissolved in 1520 cc. of ethanol and the solution sprayed, in conjunction with other flavoring matter, onto 200 pounds of cured, cased, blended and shredded commercial tobacco. The tobacco mixture so treated is manufactured into cigarettes using the procedures and equipment normal to conventional manufacture.
Example X Approximately 276 grams of mono menthylmaleate and 57 grams of either natural or synthetic menthol is dissolved in 1520 cc. of 95% ethanol and the solution sprayed, in conjunction with other flavoring matter, onto 200 pounds of cured, cased, blended and shredded commercial tobacco. The tobacco mixture so treated is manufactured into cigarettes using the procedures and equipment normal to conventional manufacture.
Example XI Example XII Approximately 100.6 grams of mono menthylsuccinate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
Example XIII Approximately 119.5 grams of mono menthylphthalate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
Example XIV Approximately 136.8 grams of mono menthylhemimellitate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
Example XV Approximately 105.3 grams of mono menthyl-3-methylmaleate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
Example XVI Approximately 133.6 grams of mono me-nthylcamphorate are dissolved in 500 cc. of absolute ethanol and the solution sprayed on approximately 30 pounds of cured, cased and blended commercial tobacco. The tobacco treated in this fashion is manufactured into cigarettes using normal factory procedures and equipment.
Tobacco products made in accordance with the specific examples given herein have been evaluated and the products were observed to burn slower at smolder than a comparable control, to have increased firmness and to require more puffs under a controlled smoking regime and, when tested organoleptically, the smoking products were found to deliver smoke having a pleasing and cooling taste and aroma characteristic of menthol at an apparently increasing rate when the ester alone was used and at an apparently constant rate when menthol was mixed with the ester.
Modifications may be made in the described embodiments of my invention and in the illustrated examples without departing from the scope of the invention set forth in the accompanying claims.
I claim:
1. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein a material selected from the group consisting of mono menthylmaleate, mono menthylsuccinate; mono menthylphthalate; mono menthyl-Z-methylmaleate; mono menthyl-3-methylmaleate; mono menthylcamphorate; cis-mono menthylcyclohexene 1,2 dicarboxylate; cis-l-menthyl-4-cyclohexene-1,2-dicarboxylate; mono menthy lhomophthalate; mono menthylhomoquinolate; mono menthyl meso dimethylsuccinate; mono menthyl-a,a-dimethylsuccinate; mono menthy-lhemimellitate; mono menthylmethylsuccinate; mono menthylaconitate; mono menthylitaconate; mono menthyl-cis-cyclopropanedicarboxylate and mono menthylmalate; cis-mono menthylglutaconate.
2. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylmaleate.
3. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylsuccinate.
4. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylphthalate.
5. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono mentlxyl-Zmrethylmaleate.
6. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthyi-3-methylmaleate.
7. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein mono menthylhemimellitate.
8. The method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco a material selected from the group consisting of mono menthylnialeate, mono menthylsuccinate; mono methylphthalate; mono ment-hyl-Z- methylmaleate; mono menthyl-S-methylmaleate; mono menthylcamphorate; cis mono menthylcyclohexene-1,2- dicarboxylate; cis-1-menthyl-4-cyclohexene-1,Z-dicarboxylate; mono menthylhomophthal-ate; mono menthylhomoquinolate; mono menthyl-meso-dimethylsuccinate; mono menthyl-a,a-dimenthylsuccinate; mono tmenthylhemimellitate; mono menthylmethylsuccinate; mono menthylaconitate; mono menthylitaconate; mono menthyl-cis-cyclopropanedicarboxylate; mono menthylmalate and cis-mono menthylglutaconate.
9. The method of imparting improved smoking flavor characteristics to .a tobacco product which comprises incorporating in smoking tobacco mono rnenthylmale ate.
10. The method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthylsuccinate.
11. The method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthylphthalate.
12. The method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono-menthyl-Z-methylmaleate.
13. The method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthyl-3-methylmaleate.
14. The method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono-menthylcamphorate.
15. The method of imparting improved smoking flavor characteristics to a tobacco product which comprises incorporating in smoking tobacco mono menthylhemimellitate.
16. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein between 0.01 and 1% by weight of a mono menthyl ester of a polycarboxylic acid.
17. A smoking tobacco product having improved smoking flavor characteristics comprising a smoking tobacco having incorporated therein between 0.01 and 1% by Weight of a mono menthyl ester of a polycarboxylic acid having the formula:
COOR
in which R is the menthyl radical and R is a material selected from the group consisting of saturated and unsaturated aliphatic and aromatic and hetero-aromatic polycarboxylic acid radicals and n is the total number of carboxyl groups in the acid from which the ester is derived.
18. The method of imparting improved smoking flavor characteristics to a smoking tobacco product which comprises incoporating in smoking tobacco between 0.01 and 1% by weight of a mono menthyl ester of a polycarboxylic acid.
19. The method of imparting improved smoking flavor characteristics to a smoking tobacco product which comprises incorporating in smoking tobacco between 0.01 and 1% by weight of a mono menthyl ester of a polycarboxylic acid having the formula:
COOR
in which R is the menthyl radical and R is a material selected from the group consisting of saturated and un saturated aliphatic and aromatic and heteroaromatic poly- F? s. carboxylic acid radicals and n is the total number of carboxyl groups in the acid from which the ester is derived.
References Cited'in the file of this patent UNITED STATES PATENTS 1,673,216 Vuccino June 12, 1928 2,822,306 Thienmann et a1. Feb. 4, 1952 2,921,089 Hagenmeyer et a1 Jan. 12, 1960 w 2,936,320 Benoit May 10, 1960 2,941,907 Tousignant June 21, 1960 FOREIGN PATENTS 1,065,767 Germany Sept. 17, 1959 12,736 Great Britain 1896 OTHER REFERENCES D. L. Tabern: Chemical Abstracts, 1941, 5136.

Claims (1)

1. A SMOKING TOBACCO PRODUCT HAVING IMPROVED SMOKING FLAVOR CHARACTERISTICS COMPRISING A SMOKING TOBACCO HAVING INCORPORATED THEREIN A MATERIAL SELECTED FROM THE GROUP CONSISTING OF MONO MENTHYLMALEATE, MONO MENTHYLSUCCINATE; MONO MENTHYLPHTHALATE; MONO MENTHYL-2-METHYLMALEATE; MONO MENTHYL-3-METHYLMALEATE; MONO MENTHYLCAMPHORATE; CIS-MONOMETHYLCYLOHEXENE - 1,2 - DICARBOXYLATE; CIS-1-MENTHYL-4-CYCLOHEXENE-1,2-DICARBOXYLATE; MONO MENTHYLHOMOPHTHALATE; MONO MENTHYLHOMOQUINOLATE; MONO MENTHYL - MESO - DIMETHYLSUCCINATE; MONO MENTHYL-A,A-DIMETHYLSUCCINATE; MONO MENTHYLHEMIMELLITATE; MONO MENTHYLMETHYLSUCCINATE; MONO MENTHYLACONITATE; MONO MENTHYLITACONATE; MONO MENTHYL-CIS-CYCLOPROPANEDICARBOXYLATE AND MONO MENTHYLMALATE; CIS-MONO MENTHYLGLUTACONATE.
US119779A 1961-06-27 1961-06-27 Smoking tobacco product and method of making the same Expired - Lifetime US3111127A (en)

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US119779A US3111127A (en) 1961-06-27 1961-06-27 Smoking tobacco product and method of making the same
GB20449/62A GB939576A (en) 1961-06-27 1962-05-28 Improvements in or relating to smoking tobacco product and method of making the same
DK284462AA DK116713B (en) 1961-06-27 1962-06-26 Process for the production of a mentholed smoking tobacco product with good taste-releasing properties.
CH765662A CH458169A (en) 1961-06-27 1962-06-26 Menthol flavored smoking tobacco product and process for making the same
BE619401A BE619401A (en) 1961-06-27 1962-06-26 Smoking tobacco and its manufacturing process
CY29364A CY293A (en) 1961-06-27 1964-06-13 Improvements in or relating to smoking tobacco product and method of making the same
MY1964103A MY6400103A (en) 1961-06-27 1964-12-31 Improvements in or relating to smoking tobacco product and method of making the same

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