Nicotine from tobacco extract

By repeated distillation of the higher boiling fraction the pure base is obtained as a colourless liquid of boiling point 114°/10 mm., 120°/14 mm. At atmospheric pressure nicotine boils without decomposition at 240°. The yield varies from 4 to 6 g. 

The specimen turns brown very soon if exposed to the air, and must be kept in a sealed glass tube. 

From a sample prepare the dimethiodide thus Dissolve the base in a little methyl alcohol and warm the solution with about three parts of methyl iodide. Recrystallise from a little methyl alcohol. 

Oxidise some nicotine to nicotinic acid with permanganate. 

Most alkaloids are isolated from plant extracts by conversion into the difficultly soluble salts which they form with complex acids such as hexachloroplatinic acid, chlorauric add, phosphotungstic add, hydroferro-cyanic add, Rdnecke s add, etc. Perchloric add, picric add, flavianic add, mercuric chloride, iodine in potassium iodide are also used. 

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Above the critical temperature and pressure, a substance is referred to as a supercritical fluid. Such fluids have unusual solvent properties that have led to many practical applications. Supercritical carbon dioxide is used most commonly because it is cheap, nontoxic, and relatively easy to liquefy (critical T = 31°C, P = 73 atm). It was first used more than 20 years ago to extract caffeine from coffee dichloromethane, CH2C12, long used for this purpose, is both a narcotic and a potential carcinogen. Today more than 10s metric tons of decaf coffee are made annually using supercritical C02. It is also used on a large scale to extract nicotine from tobacco and various objectionable impurities from the hops used to make beer. 

Extraction of foods and pharmaceuticals Caffeine from coffee and tea Flavors, cholesterol, and fat from foods Nicotine from tobacco... 

Aqueous extraction procedures for water-soluble molecules are especially advantageous in CE. For example, toluene extraction of nicotine from tobacco prior to gas chromatography gives low recoveries compared to aqueous extraction and CE [39],... 

Supercritical fluid extraction processes are particularly appropriate for the separation and isolation of biochemicals where thermal decomposition, chemical modification, and physiologically-active solvents are undesirable. Examples of these bioseparations include the extraction of oils from seeds using carbon dioxide (1), of nicotine from tobacco using carbon dioxide-water mixtures (2), and of caffeine from coffee beans again using carbon dioxide-water mixtures (3). 

Carbon Dioxide - Water - Crotalaria Spectabilis System. Water has been used as a CO-solvent in the extraction of caffeine from coffee and nicotine from tobacco. To extract caffeine from coffee beans, Zosel (3) recommended the pre-saturation of the carbon dioxide with water before passing the fluid through the coffee bean bed. In the case of nicotine from tobacco, Hubert and Vitzthum (2) first soaked the tobacco with up to 25 wt.% water and subsequently passed carbon dioxide through the tobacco bed. The water acted as a co-solvent as it saturated the fluid phase. Both of these processes have proven highly selective toward the alkaloids present in the plant material. Therefore, water was used as a co-solvent in the present study. 

Nicotine, from tobacco leaf extract, used as a contact insecticide... 

The most common use of scC02 is in the extraction of caffeine from coffee or tea, nicotine from tobacco, and essential oils from plants. The isolation of products is simple, with the evaporation of the solvent with no residue. Another important application is in supercritical fluid chromatography (SFC). 

Extraction of nicotine from tobacco using supercritical fluid is carried out in a manner quite similar to the decaffeination of roasted coffee described in U.S. 3,843,824. Tobacco is first contacted with dry supercritical CO2 which extracts the aroma constituents. The C02-aroma stream is expanded to subcritical conditions via expansion across a valve the aromas precipitate from soludon. The CO2 vapor is recompressed, is adjusted in temperature to supercritical conditions via heat exchangers, and is recycled to the extractor via a compressor. The aromas extracdon step condnues until the aroma constituents are removed from the tobacco. 

The use of some compounds against pests was known from earlier times these were based on sulfur and arsenic. Natural extracts from plants such as nicotine from tobacco, or pyrethrum from chrysanthemums were used initially in the 16th and 19th centuries respectively. 

There are many literature reports on industrial uses of supercritical fluids, and many patents have been issued for various uses of supercritical fluids as solvents in extraction processes. Randall (1) prepared an excellent review on the uses and patents issued up to 1982 in the area of supercritical fluid extraction and chromatography. Many of these applications deal with natural products such as flavors, fragrances, oils and fats, or the removal of unwanted components from natural materials such as caffeine from coffee or tea and nicotine from tobacco. 

Food and luxury goods industry (e.g., extraction of vegetable fat and oil from oil seeds, production of hops and spices extracts, extraction of caffeine from coffee beans and nicotine from tobacco, by using hygienically safe supercritical gases as the solvent, such as carbon dioxide)... 

Removal of pollutants or unwanted components from the product by extraction (for example, to remove caffeine from coffee beans, separation of nicotine from tobacco)... 

Some examples of successful commercial selective extractions are the removal of caffeine from coffee or the solubilization of nicotine from tobacco both accomplished on moist matrices to aid in selectively solubilizing the alkaloid component. Selective extraction has been demonstrated for the segregation of essential oil from other lipid components in natural extracts derived from fruits and for the separation of aroma components in cocoa butter from the base oil. Other enrichment SEE schemes that have been reported include the fractionation of carotenoid from leaf protein concentrate [25], the fortification of sterols in seed oils [26], and the isolation of lecithin (phospholipid-containing fraction) from triglycerides [27]. 

SFE is common in the food, pharmaceutical and cosmetic industries, where it extracts caffeine from coffee beans, bitter from hops, tar and nicotine from tobacco, and other natural compounds from spices, flowers, aromatic woods, and medicinal plants. 

Other projects involving supercritical CO2, to name a few, are the extraction of cholesterol from meat, fat from potato chips, and nicotine from tobacco. Supercritical CO2 heat pumps are now marketed in Asia using CO2 as a natural refrigerant. 

Tobacco and its alkaloids have long ceased to have any therapeutic importance, but their extensive use as insecticides and the demand for nicotine for the manufacture of nicotinic acid have stimulated interest in processes of extraction and methods of estimation. On the latter subject there is a voluminous literature, of which critical resumes have been published by various authors.Recent work on this subject has been specially concerned with (1) the development of miero- and semi-miero-methods suitable for estimating nieotine in tobacco smoke and the distribution of nieotine on sprayed garden produce, in treated soils and in tobaeeo leaves,(2) the study of conditions necessary to ensure satisfactory results in using particular processes, " and (3) methods of separation and estimation of nicotine, nomicotine and anabasine in mixtures of these bases. ) In the United States and in Russia considerable interest is being shown in the cultivation of types of tobacco rich in nicotine, in finding new industrial uses for tobacco and its alkaloids, and in possible by-products from tobacco plants such as citric and malic acids, i " Surveys of information on tobacco alkaloids have been published by Jackson, i Marion and Spath and Kuffner. ... 

In a further application of MI-SPE, theophylline could be separated from the structurally related caffeine by combining the specific extraction with pulsed elution, resulting in sharp baseline-separated peaks, which on the other hand was not possible when a theophylline imprinted polymer was used as stationary phase for HPLC. A detection limit of 120 ng mb1 was obtained, corresponding to a mass detection limit of only 2.4 ng [45]. This combination of techniques was also used for the determination of nicotine in tobacco. Nicotine is the main alkaloid in tobacco and is the focus of intensive HPLC or GC analyses due to its health risk to active and passive consumers. However, HPLC- and GC-techniques are time-consuming as well as expensive, due to the necessary pre-purification steps required because the sample matrices typically contain many other organic compounds besides nicotine. However, a simple pre-concentration step based on MI-SPE did allow faster determination of nicotine in tobacco samples. Mullett et al. obtained a detection limit of 1.8 jig ml 1 and a mass detection limit of 8.45 ng [95]. All these examples demonstrate the high potential of MI-SPE to become a broadly applicable sample pre-purification tool. 

The widespread personal consumption of nicotine is not its only role. In 1763 it was first used as an insecticide. The potent nervous system effects of nicotine kill or deter insects. Nicotine is extracted from tobacco leaves by steam or solvent treatment and then sprayed on vegetation where it is readily absorbed by insects. 

Several nerve toxins produced by plants are interesting because of their insecticidal properties. Insecticidal nicotine is extracted from tobacco. Rotenone (Figure 19.2) is synthesized by almost 70 legumes. This insecticidal compound is safe for most mammals, with the notable exception of swine. The most significant insecticidal plant derivatives, however, are the pyrethrins, discussed below. 

The water extract from Nicotiana tabacum was prepared by distillation of nicotine contained liquor from tobacco leaves, as described in D.R. Patent No. 319,846 September 12, 1913. 

In the seventeenth century the first naturally occurring insecticide, nicotine from extracts of tobacco leaves, was used to control the plum curcuUo and the lace bug. Hamburg (1705) proposed mercuric chloride as a wood preservative and a hundred years later Prevost described the inhibition of smut spores by copper sulfate. 

Yasumatsu and Murayama15 used polyethylene glycol 20 M as stationary phase for the determination of nicotine in tobacco samples. The alkaloids were extracted with 0.5 N HC1 containing isoquinoline as an internal standard. The mixture of the extract and an equivalent volume of N NaOH was injected into the injector of the gas chromatograph fitted with a soda lime tube. The nicotine content was determined from the peak heights of nicotine and isoquinoline. The relative standard deviation was 1.9 %. 

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