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Product Design

Migration of Nicotine Progress Report I

Date: 09 Jan 1978
Length: 8 pages
00265115-5122
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Abstract

Reports results of CONAP project to enrich reconstituted leaf [RL] with nicotine and study the migration of nicotine from cut tobacco to RL. Lists experimental conditions including: spraying RL with ammonia which was then mixed with cigarette tobacco, use of phosphoric acid and monoammonia phosphate, evaluation of moisture content on nicotine migration, nicotine migration under storage conditions, and elucidating the chemical properties using phosphoric acid treated filter papers. Presents results of nicotine transfer of Kent Gold Light Blend and nicotine transfer properties using various additives. Lists migration of nicotine during aging, leaf analysis of various tobacco grades including 7-74, HL-74, SMEM-75, VLO-75, MX-70, MIIX-70, MIIX-71 and reports leaf pH, %Nicotine, %Nitrogen, % Total Volatile Bases, % Nicotine migration to filter paper and correlates leaf pH, Nicotine, Nitrogen and Total Volatile Bases to nicotine transfer. Recommends further studies to include: quantitation of nicotine migration, migration of nicotine to RL, "migration of nicotine to Cytrel or similar materials", characterizing compounds that co-migrate with nicotine and the migration of nicotine during storage.

User-Contributed Notes

Fields

Author
Larson, T.M.
Recipient
Ireland, M.S.
Minnemeyer, Harry Joseph, Ph.D. (Lorillard R&D Dept.; worked on nicotine augmentation project)
Moring, Tomas B. (Lor, Research Administrator, 1979)
Thomas, Robert L. (LOR Engineer)
Engineer worked with Lorillard
Schultz, Frederick J., Ph.D. (VP of Lorillard, Inc. '89-95)
Tucker, Charles. L., Jr. (Lor, Product Development Manager, 1979-1983)
Hypothesis
Design changes over time
Changes in cigarette design over the past half century.
Nicotine transport, transfer, and uptake
Design changes which alter nicotine delivery or effect how the product causes and maintains dependence, including transfer of nicotine from tobacco to smoke, and uptake into the body.
Use of additives
Modification of tobacco products through use of additives and measuring effects on dependence, behavior, and toxicity.
Keyword
Acidity (Low pH)
Alkalinity (High pH, Basic)
Nicotine delivery (Smoke nicotine or nicotine yield)
Nicotine manipulation
Additive
Acetic acid
Ammonia
see also: Ammonium bicarbonate, Ammonium carbonate, Ammonium chloride, Ammonium hydroxide, Ammonium sulfide, Diammonium phosphate, and Urea
ammonia sulfate
Citric acid
Diammonium phosphate
Hydrochloric acid
Lactic acid (Lactic Acid and dl-Lactic Acid)
Malic acid
monoammoniaphosphate
nitric acid
Phosphoric acid
Sulfuric acid
Tartaric acid
Smoke Constituent
Nicotine
Design Component
Ammoniated blend
Leaf pH
Nicotine content (Tobacco nicotine content)
Total nicotine in the unburnt tobacco rod
Nicotine transfer efficiency (NTE)
Reconstituted leaf (RL)
PM @reconstituted_tobacco, c. 1970s-1980s
Operation/Project
CONAP (Project N-187) (Continuation of Nicotine Augmentation Project)
Continuation of nicotine augmentation project
Named Organization
Lorillard Research Center
Brand
Golden Lights
Subject
acids (additives)
additives
Ammonia (Additives)
nicotine technology
pH Manipulation (Technology)
Reconstituted Tobacco (Design)
Tobacco Type (Design)

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Page 1: eow61e00
Accession number 1125 Larc ffard Research Cenger Gracn: fxmrm MIGRATION OF NICOTINE PROGRESS REPORT I Submitted by: T. M. Larson Report number: B-1.92 Surnmary or Abstract: Date: 1/9/78 Nicotine migrated~to acid or salt treated filter papers which were exposed to tobacco at room temperature or under heat. Severa:l acids and salts were capable of facilitating the migration. The nicotine content appeared to be the most important variable of the tobacco related to the degree of nicotine migration at elevated temperatures. For nicotine migration (at elevated temperatures) to take place, it was shown that the tobacco had to be in contact with the sub- stance to which the nicotine migrated. /lmh Xc: Dr. F. J. Schultz Dr. H. J. Minnemever Mr. C. L. Tucker Mr. T. B. Moring: Ms. M. S. Ireland Mr. R. L. Thomas Library
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INTRODUCTION It is thought that one approach to solving the problems associated with the CONAP project is to enrich the RL with nicotine. The discovery by T. B. Moring of the migration of nicotine from cut tobacco to RL during storage suggested'a unique method of enriching RL. With this in mind, a study of the migration of nicotine was undertaken. EXPERIMENTAL It is known'that our production RL when blended with cut tobacco, does not pick up nicotine. However, when RL made from the same by-products plus ammonia and phosphoric acid is blended with tobacco, the nicotine content rises significantly. The initial experiments were conducted to determine the effect of ammonia and phosphoric acid on nicotine migration. The first experiment was one in which.production RL was sprayed with an ammonia solution, mixed with cigarette tobacco, cut, and then heated (or dried) for varying lengths of time. The results of this experi- ment showed that ammonia had no positive effect on nicotine migration. No significant increase in nicotine content of the treated RL was found. The same experi- ment was conducted with RL treated with phosphoric acid. At the Danville plant, ten pounds of diammonium phosphate was added to 125 gallons of RL slurry, which was then made into RL. This RL was made into a cigarette blend and stored'for 2 weeks. At the end of two weeks the nicotine content of the RL had increased from 0.65% to 1.05%. To eliminate many unknown variables inherent in RL, and to "standardize" the experiments, further work was done using filter paper as a substitute for RL. Filter papers were treated with various compounds, usually by dipping in a solution then air drying, then torn in pieces about 1 1/2"' square, and layered'in cut tobacco in moisture tins. The moisture tins were then closed~ and placed in a 95°C oven for from one to two hours. After removal from the oven the paper was separated from the tobacco, shredded and sent to the leaf lab for nicotine analysis. The first experiment done with filter paper showed significant nicotine migration.to the filter paper. The `
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- 2 paper was treated with~'a 3% solution of monoammonium~ phosphate and heated with tobacco as previously described for one and one-half hours. Analysis showed the paper to contain 2.5% nicotine by weight. The experiment was repeated using a paper treated with a 5% phosphoric acid solution and heating time was 2.hours. The paper con- tained 5:4°s nicotine. To check the mass balance of'nicotine migration equal amounts of monoammonium phosphate treated paper and Kent Golden Light tobacco were heated together for one hour. .Results of nicotine analyses-on the paper and tobacco before and after exposure indicated that no nicotine was lost overall. (See Table 1) An experiment was conducted to evaluate the effect of moisture on nicotine migration and also to test various compounds for their effectiveness in nicotine migration. Filter papers were dipped in 5% solutions of the compounds listed in Table 2.and allowed to air dry. •':The treated papers were then mixed or layered within L-2 tobacco (analysis given in Table 2) at 18% and 8% moisture. The tobacco to paper ratio was four to one by weight. The mixtures were heated at 95°C for 2 hours. The resulting nicotine concentrations of the papers are given with the corresponding compounds and moisture levels in Table 2. Data in Table 2 show that the non-volatile acids, and the compounds which decompose under heat to yield non-volatile acids facilitate the migration of nicotine. It also appears that under the conditions of this experi- ment, the 8'$ moisture level,was more favorable for nico- tine migration than the 18% level. In cases where nicotine migrated significantly, (Table 2) it should be noted that the pHvalues for papers treated with the effective acids were approximately 2.5 or less. The pH of the filter papers were determined' as if the papers were tobacco leaf. An experiment was conducted to evaluate nicotine migration under simulated~storage conditions. Filter paper treated with a 5% diammonium phosphate solution was shredded and mixed with cut L-2 tobacco then sealed in glass jars. After one week, and each week thereafter, a jar was opened and the filter paper was removed and analyzed for nicotine. The results of this experiment indicated that the nicotine migration was essentially complete after three weeks.(See Table 3).
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To determine if the tobacco had•to be in contact with the material to which the nicotine transferred, the following experiment was conducted. High nicotine L-2 tobacco was placed in a moisture tin along with filter paper which had been treated with a 3% mono- ammonium phosphate solution. The tobacco was separated about one-fourth inch~from the filter paper by means of a copper screen. After heating for two hours at 95°C, the paper was removed'and analyzed for nicotine. The paper contained 0.95% nicotine, an amount that compared favorably with data previously collected, but not reported here. However, the amount was not considered significantly high,'especially when compared to the "control papers" listed in Table 2. The experiment was repeated, using paper dipped in 5% phosphoric acid, a compound.proven to facilitate nicotine transfer. After two hours of heating at 95°C the moisture tin and contents were allowed to-sit at room temperature for four days. The result of the nicotine analysis on the paper after the four day period showed the paper to contain 0.40% nico- tine. An additional experiment confirmed this result, indicating that contact between paper and tobacco was essential for significant migration of nicotine. The migration:may have been a result of nicotine vapors condensing on the acid treated paper, but unless the tobacco was in contact or "very close" to the paper, insignificant amounts of nicotine were transferred!. An attempt was made to correlate various chemical properties of tobacco with the amount of nicotine trans- ferred from the tobacco to phosphoric acid treated paper. Filter papers, having been dipped in 5% phosphoric acid and allowed to dry, were exposed to seven different tobaccos for two hours at 95°C. The seven tobaccos were analyzed by the leaf lab for nitragen (NIT), nico- tine (NIC), and total volatile bases (TVB). Leaf pH was also obtained~. Table 4 summarizes the data obtained. These data, along with the percent nicotine found on the treated filter paper, were fed into the computer using the multiple linear regression program. A copy of the correlation matrix for this multiple linear regression is given in Figure 1. It appears, from the limited number of samples tested!in this manner, that the most important factor in nicotine migration is the amount of nicotine present on the tobacco. (This corre- lation may not be valid'foz nicotine migration at room temperature)
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SUMMARY To date, a number of compounds have been found which will facilitate the migration of nicotine. It appears that under conditions of elevated temperature, ammonia does not play an important role in the migration of nicotine. Under simulated storage conditions nico- tine migration was maximized' after three weeks. Also it appears that contact between tobacco and substance to which nicotine.migrates is essential for migration.. When using phosphoric acid treated filter paper as the substance to which nicotine migrated, the extent of migration was directly proportional to the nicotine content of the tobacco. FURTHER WORK Work will be in progress one or more of the following areas. 1. Quantitation of nicotine migration. 2. Migration of nicotineto reconstituted leaf. 3. Migration of nicotine to Cytrel~ or similar material. A. Isolation and identification of other compounds which~may migrate with~ nicotine. 5. Migration!of nicotine under storage conditions.
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TABLE 1. Mass Balance for Nicotine Migration Sample % nicotine % nicotine transferred Kent Golden Light Blend 2.1% j Kent Golden Light after exposure 1.3% -38% Paper exposed to KGL 0.75% +36% ' Paper exposed to KGL 0.65% +31% TABLE 2. Nicotine Transfer Properties of Various Compounds Compound .$ nic. on paper % nic. on paper transferred transferred at 8% moisture at 18% moisture Tartaric Acid 4.92 4.48 . Citric Acid 5.45 4.90 Sulfuric Acid 4 88 - ~ _ . Phosphoric Acid 6.,17 6.40 Hydrochloric Acid 0.85 1.12 Nitric Acid 1.00 1.05 Malic Acid 5.49 4.72 Acetic Acid 0.60 0.76 Lactic Acid 1.80 1.78 Ammonium Sulfate 4.35 3.83 Diammonium_Sulfate 4.97 4.17 Control 0.85 1.01 L-2 Tobacco Analysis (Whole Leaf, cut) Nitrogen 2.65%, TVB 0.680', Nicotine 3.74%, TRS 15.5%, pfl of leaf 5.6 0
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TABLE 3. Migration of Nicotine at Room Temperature Time % Nicotine on Filter Paper Start 0.0 1 week 1.46 2 weeks 2.25 3 weeks 2.89 4 weeks 2.45 5 weeks 2.51 7 weeks 2.53 Control ('untreated filter paper) 0.30
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TABLE 4. Leaf Analysis of Various Tobaccos (With % Nicotine Transferred) Tobacco .(Grade) Leaf pH % NIC. % NIT, % TVB % NIC. found on paper 7-74 5.5 3.10 4.10 1.03 4.26 HL-74 5.'6 2.75 4.32 0.97 4.18 SMEX-75 5.2 3.17 2.65 0.50 4.80 VLO-75 5.3 2.13 2.61 0.42 2.63 MX-70 6.6 0.86 2.08 0.24 2.05 MIIX-70 6.1 1.35 3.15 0.61 1.85 MIIX-71 5.6 1.12 2:63 0.44 1.86 FIGURE l. CorrelationMatrix Nicotine Transferred Leaf pH Nic. Nit. TVB's Leaf pH - 0.56 - -0.74 -0.31 =0.35 Nicotine 0.94 -0.74 - 0.61 0.68 Nitrogen 0.72 -=0.31 0.61 - 0.98 TVB's. 0.76 -0.35 0.68 0.98 -

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