Philip Morris Inc.

Philip Morris Products Inc.

Harvey J Grubbs

Yoram Houminer

William R Johnson, Jr

Thomas V Van Auken

Edward B Sanders

W Geoffrey Chan

Kenneth F Podraza

Everett W Southwick

Ravi Prasad

John Bryant Paine, Iii

Jeffrey I Seeman

William B Edwards, Iii

Tony M Howell

Charles R Howe

Richard H Cox

John D Naworal

Stephen A Haut

Eric G Rundberg, Jr

A process is provided for the improved removal of nicotine from tobacco. An essentially nicotine-free solvent in the supercritical or liquid state is fed into a first end of an extraction flow system containing tobacco and a nicotine-rich solvent is discharged from a second end of the extraction flow system. Periodically a portion of extracted tobacco is discharged from the first end of the extraction system while simultaneously a portion of an unextracted tobacco is charged to the second end of the extraction system. Nicotine is then entrapped in an entrapment material or otherwise removed from the solvent and solvent is recycled through the extraction flow system. Various materials are provided as entrapment materials. Among the entrapment materials provided are aqueous solutions containing absorbent selected from various acids and salts. Among the acids and salts provided as entrapment materials are sulfuric acid, phosphoric acid, nitric acid, tartaric acid, citric acid, malic acid, lactic acid, malonic acid, succinic acid, acetic acid, glutamic acid and monopotassium citrate.

Process and apparatus for the semicontinuous extraction of nicotine from

This invention provides smoking compositions which contain a novel .beta.-hydroxycarboxylate flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as calcium bis(2,2-diethyl-3-hydroxy-4-phenylmethylenedecanoate) pyrolyzes and releases .alpha.-hexylcinnamaldehyde as a volatile flavorant component of the cigarette smoke.

Smoking compositions containing an .alpha.-alkylcinnamaldehyde-release

This invention provides smoking compositions which contain a novel vanillin flavorant-release additive. A cigarette smoking product comprising (1) a combustible filler selected from natural tobacco, reconstituted tobacco and tobacco substitutes, and (2) a paper wrapper which has incorporated therein a flavorant-release additive corresponding to the formula: ##STR1## where R is methyl or ethyl.

Smoking compositions containing a vanillin-release additive

This invention provides smoking compositions which contain a novel vanillin flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as ethyl 3-(4'-butoxycarbonyloxy-3'-methoxyphenyl)-3-hydroxy-2-phenylpropanoate pyrolyzes into vanillin and ethyl phenylacetate flavorants as volatile components of the cigarette smoke. A present invention flavorant-release additive is represented by the formula: ##STR1## where R is methyl or ethyl; R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl substituent; R.sup.2 is hydrogen or a C.sub.1 -C.sub.4 alkyl or C.sub.6 -C.sub.10 aromatic substituent; and R.sup.3 is a C.sub.1 -C.sub.4 alkyl or C.sub.6 -C.sub.10 aromatic substituent.

This invention provides tobacco and non-tobacco smoking compositions which contain a heterocyclic-hydroxy-substituted carboxylate compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a heterocyclic-hydroxy-substituted carboxylic acid flavorant additive such as 2-(2-butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionic acid: ##STR1## Under smoking conditions the above illustrated heterocyclic-hydroxy-substituted carboxylate additive and its pyrolysis products flavor the mainstream and sidestream smoke.

Smoking compositions

A process is provided for the selective removal of basic materials from plant products, in particular, for removing nicotine from tobacco without materially affecting the content of the other components of the tobacco. Tobacco is traversed with a solvent at high pressure and in a physical state which is either a liquid at a pressure of from about 500-300 atmospheres or a supercritical fluid wherein nicotine and the other components dissolve in the solvent. As the single means of removing substances from the solvent, the solvent is then passed through an acid-containing trap where the solvent is essentially freed of nicotine. The solvent, depleted of nicotine and enriched in the other components, is then recycled to the tobacco to reextract nicotine. In addition, the tobacco may be pretreated with a chemical base which does not substantially react with the tobacco components under ambient conditions and which are not necessarily affected by the process conditions but are nonetheless effective in increasing the amount of nicotine which can be extracted by the process of this invention. Pretreatment of the tobacco with a chemical base neutralizes nicotine salts and permits the extraction process to be carried out under milder conditions.

Process for removal of basic materials

This invention provides smoking compositions which contain a glycosylamine compound as a flavorant-release additive. Under cigarette smoking conditions, an additive such as 1-amino-1-deoxyglucose pyrolyzes into volatile constituents which enhance the flavor of the mainstream smoke and the aroma of sidestream smoke.

Smoking compositions containing a glycosylamine flavorant additive

This invention provides tobacco compositions which contain a hydroxy-substituted carboxylate compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a hydroxy-substituted alkanoate flavorant additive such as ethyl 2-(2-butyl)-3-hydroxy-3-methyl-33-phenylpropionate: ##STR1## Under smoking conditions the above illustrated hydroxy-substituted alkanoate additive and its pyrolysis products flavor the mainstream and sidestream smoke.

Flavor-release .beta.-hydroxy-ester compositions

This invention provides tobacco and non-tobacco smoking compositions which contain a heterocyclic-hydroxy-substituted carboxylate compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a heterocylic-hydroxy-substituted carboxylic acid flavorant additive such as 2-(2-butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionic acid: ##STR1## Under smoking conditions the above illustrated heterocyclic-hydroxy-substituted carboxylate additive and its pyrolysis products flavor the mainstream and sidestream smoke. The invention also provides for the method of preparing smoking compositions and the method of comprising the aroma imparted by the burning of a combustible article employing a heterocyclic-hydroxy-substituted carboxylate.

This invention provides heterocyclic-hydroxy-substituted carboxylate esters which are useful as flavorant additives for smoking compositions. In one of its embodiments, this invention provides a heterocyclic-hydroxy-substituted alkanoate flavorant additive such as ethyl 2-(2-butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionate: ##STR1##

Heterocyclic-hydroxy-substituted carboxylate esters

This invention provides tobacco compositions which contain a hydroxy-substituted carboxylate compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a hydroxy-substituted alkanoate flavorant additive such as ethyl 2-(2-butyl)-3-hydroxy-3-methyl-3-phenylpropionate: ##STR1## Under smoking conditions the above illustrated hydroxy-substituted alkanoate additive and its pyrolysis products flavor the mainstream and sidestream smoke.

In one of its embodiments this invention provides a smoking composition which contains a novel type of flavorant additive as exemplified by polymerized ethyl 2-propenyl 2-(2-butyl)malonate: ##STR1##

This invention provides tobacco and non-tobacco smoking compositions which contain a heterocyclic-hydroxy-substituted carboxylate compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a heterocyclic-hydroxy-substituted alkanoate flavorant additive such as ethyl 2-(2-butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionate: ##STR1## Under smoking conditions the above illustrated heterocyclic-hydroxy-substituted alkanoate additive and its pyrolysis products flavor the mainstream and sidestream smoke.

A unitary pack of smoking tobacco products is provided in which a flavorant is incorporated in some of the smoking tobacco products in the form of a polymeric alcohol flavorant-release composition which has the general formula: ##STR1## wherein R is selected from aliphatic, alicyclic, heterocyclic and aromatic hydrocarbon radicals; R.sup.1 and R.sup.2 are selected from hydrogen and aliphatic, alicyclic, heterocyclic and aromatic hydrocarbon radicals; and n is an integer. These polymers release a flavorant when heated. Such polymers include polymers formed from .alpha.-substituted vinyl menthyl carbonate esters, such as poly(.alpha.-methylvinyl .alpha.-menthyl carbonate) and poly(.alpha.-styryl .alpha.-menthyl carbonate), which release menthol when heated. Smoking tobacco products which are made with tobacco which has been treated with a particular alcohol flavorant-release composition have been found to show no significant loss in delivery of flavor. Other smoking tobacco products which are packaged therewith do not acquire the flavor of the flavorant which is contained in the alcohol flavorant-release composition, despite the absence of internal vapor barriers between the different flavored tobacco products.

Unitary pack of smoking tobacco products containing polymeric alcohol

This invention provides tobacco compositions which contain a flavorant-release oligomeric and polymeric derivative corresponding to the structural formula: ##STR1## wherein R is a member selected from the group consisting of hydrogen and aliphatic, alicyclic and aromatic hydrocarbon radicals containing between 1 and about 10 carbon atoms, with the proviso that R is hydrogen when m is zero; R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are members selected from the group consisting of hydrogen and aliphatic, alicyclic and aromatic hydrocarbon radicals; and m and n are integers.

Growing community of inventors

Mechanicsville, VA, United States of America

Harvey J Grubbs