Ammonia Technology Conference Minutes

Product Design

Ammonia Technology Conference Minutes

Date: 12 Jun 1989
Length: 148 pages
620941483
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Abstract

Recounts conference with objectives to: "1) Share information about the importance and use of ammonia technology (AT) worldwide; 2) Determine opportunities to accelerate AT application; 3) Define needed research to fill knowledge gaps; [and] 4) Discuss areas of possible collaborative research". Provides Executive Summary of each presentation along with listing of "slides in order of appearance" and some examples. Summarizes presentations entitled: "Welcome; Commercial use of ammonia technology in recons; Ammonia disposition in Marlboro; Usage of ammonia at B&W; Usage of ammonia in other U.S. competitive brands; Ammonia technology as currently used at Souza Cruz; Usage of ammonia at BATCF; Usage of ammonia by PM Europe and other competitors; Effects of ammonia on nicotine disposition in cigarette blends [including a summary of ammonia patents]; Pyrolysis of sugar-ammonia reaction products [including extensive list of smoke constituents]; Effects of ammonia on smoke tests; Reaction of ammonium hydroxide and DAP with sugars: Some chemical aspects; PM [Philip Morris] patents in area of ammonia treatments of tobacco; Current and future regulatory barriers to the usage of ammonia". Indicates "project number 495", "restricted", and "R&D-B032-89".

Fields

Author: Johnson, R. R. (BW)
Defense
Recipient: Bimms, H.; Chakraborty, Baran B. (BW RD&E Product Development Section Head)
Section Head, Product; deSiqueria, C.J.P.; Dunn, Patrick J. (ITC R&D, Montreal, Canada, c 1985-6)
Manager, Analytical Services and Director of Smoking Behavior Research at Imperial Tobacco, Canada. Went by "Pat" or P.J."; Heard, Alan L. (BAT GR & DC Programs Worldwide Coordinator)
Worldwide coordinator for British American Tobacco's Group Research and Development programmes, around the mid 1980s. BAT Group R&D Manager, Southampton, 1984.; Jewell, John N. (BW Manufacturing VP 1993)
Department Head Process; Kausch, Erwin (BAT)
Hamburg; Kohnhorst, Earl E. (BW President of US Business)
Earl E. Kohnhorst was the Director of Research for Brown & Williamson. (PMI's Introduction to Privilege Log and Glossary of Names, Estate of Burl Butler v. PMI, et al, April 19, 1996). In 1994, Kohnhorst was Executive vice president and chief operating officer of Brown & Williamson Tobacco Corp. (LAT 8/2/94). He was also vice president for research, development and engineering, BWT in 1985. (LAT 8/2/94). In a 1/17/85 memo, BWT Corporate Counsel J. Kendrick Wells said he had advised Earl Kornhorst, BWT's VP for research, development and engineering, on the need to prune scientific reports from his files. Wells marked certain reports with an X to designate those that were Deadwood in the behavioral and biological studies area. The Janus studies, secret program of biological research on the effects of smoking which showed tumor growth in animals, should be treated as deadwood. These documents should be segregated, boxed and put in the basement for possible shipment to BAT Industries in England, but no one should make any notes, memos or lists of the documents (LAT 8/2/94). Kohnhorst wrote a 4/26/85 letter re: carbon monoxide . It mentions development of Fact cigarette prototype which was designed to deliver low carbon monoxide. It describes shredded dried stems process which results in carbon monoxide reduction (E. Kohnhorst LT 4/26/85).; Lamb, Charles G. (BW Patent & Trademark Counsel)
B&W; Lauterbach, John H. (BW Scientific & Regulatory Affairs Principal Scientist)
Works in the Scientific and Regulatory Affairs Department with Scott Appleton.; McGregor, C.C.; Reynolds, Martin Lance (BW Director of Research)
Also served as Director of Product Development.; Riehl, Tilford F. Jr. (B&W R&D VP)
Worked for B&W in the RD&E Department in Development in 1972, Polar Hexane Pyrolasate in 1967, Casing & Flavoring in 1970, and Applied Product Research from 1972-73. Worked as Flavors Supervisor in 1976, was Section Head of Brand Development in 1977, Product Division Head in 1979, and Division Head Product Development from 1980-85. Riehl was Group Development Director in 1985, Director of Research in 1985 and 1986, Director of Product Development in 1987 & 1988, was in the Quality Systems Department in 1990 and Divisional Vice President.; Rittershaus, E.; Wigand, Jeffrey S., Ph.D. (B&W VP, R&D, Anti-Tobacco Witness)
Jeffrey Wigand worked for Brown & Williamson as Vice President of Research & Development & Environmental Dept. in 1986. (Source: B&W's Initial Disclosure, State of Texas vs. ATC, et al., 6/5/96); Woertz, Herb C. (BW RD&E Terminal Operations Director 1990)
Director of Technical; Zipperle, Kevin A.
Hypothesis: Behavior Targeting
Cigarette's effect of enhancing/mitigating specific behaviors; Free Nicotine; Introduction of new/unconventional products
Research and development of novel nicotine delivery devices and experimental tobacco designs.; Mainstream constituent yields
Modification of selected mainstream smoke constituents in response to health concerns.; 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.; Smoke constituent testing
Development of methods for measurement of gas and particulate yields in mainstream and sidestream smoke.; Use of additives
Modification of tobacco products through use of additives and measuring effects on dependence, behavior, and toxicity.; Use of filters, paper, and ventilation
Modification of tobacco products through use of filters, paper, and ventilation, and measuring effects on dependence, behavior, and toxicity.; Use of tobacco processing/ blends
Modification of tobacco products through changes in tobacco processing and use of blends, and measuring effects on dependence, behavior, and toxicity.; Sensory effects
Technologies used to measure, control, or alter sensory effects
Keyword: Buffer capacity; Cigarette hangover effect; Crystallization; Irritation (Attribute measure); Patents; Total particulate matter (TPM or Tar); Saturation; Cotinine
Additive: Amino acids; Ammonia
see also: Ammonium bicarbonate, Ammonium carbonate, Ammonium chloride, Ammonium hydroxide, Ammonium sulfide, Diammonium phosphate, and Urea; Ammonia caramel; Ammonium carbonate; Ammonium chloride; Ammonium diphosphite; Ammonium glycyrrhizinate (Monoammonium glycyrrhizinate or Glycyrrhizin, ammoniated); Ammonium hydroxide; Ammonium hypophosphate; Ammonium malate; Ammonium metaborate; Ammonium nitrate; Ammonium nitrite; Ammonium orthoborate; Ammonium peroxydiphosphate; Ammonium peroxymonophosphate; Ammonium polymetaphoshate; Ammonium silicate; Ammonium tetraborate; Ammonium triphosphate; Aspartic acid (l-Aspartic Acid); Banana extract; Beta-D-glucose; Calcium chloride; Cashew extract; Chlorogenic acid; Citric acid; Cocoa (Chocolate) (Cocoa Shells, Extract, Distillate and Powder)
Composed of nearly 400 identified chemical substances as of 1967; DAP; Deoxyfructosazine; Diammonium citrate; Diammonium hydrogen phosphate; Diammonium phosphate; Diammonium sulfate; EBR; Fructosazines; Glutamine (l-Glutamine); Glutanic acid; glycerin; HPC; Hydrochloric acid; Hydroxymethyl-methylpyrazines; Inositol; Lauric acid; Lauryl ether sulphate; Licorice (Licorice Fluid Extract, Powder, and Root); Licorice acide; Malic acid; Mangaba extract; Molon; Monohydrogen orthophosphate; N-methylpyridium citrate; Nitrates; Oriental tobacco flavors; Phosphate; Phosphoric acid; Pineapple (Pineapple Juice Concentrate); Potassium acid phosphate; Potassium hydroxide; Potassium nitrate; Potassium phosphate; Potassium sorbate; Proline (l-Proline); Propylene glycol; Prune (Prune Juice & Concentrate); Pyroglutamic acid; Quaber; Reaction flavors; Sodium chloride; Sodium tetraborate; Stearic acid; Sucrose (Sugar); Sulfuric acid; Tamarind extract; Urea
Smoke Constituent: 2,3-Di-ME-pyrazine; 2,3-Di-ME-pyrrole; 2,3-Dimethyl-pyrazine; 2,5-deoxyfructosazine; 2,5-Diacetylpyrazine; 2,5-Dimethyl-pyrazine; 2,6-deoxyfructosazine; 2,6-Diacetylpyrazine; 2,6-Dimethyl-pyrazine; 2,6-DM-pyrazine; 2-6-dimethylpyrazine; 2-Acetyl-4-(1,2,3,4-Tetrahydroxybutyl) imidazole; 2-Acetyl-5-methylpyrazine; 2-Acetyl-6-methylpyrazine; 2-acetyl-tetrahydroxybutylimidazole; 2-Ethenyl-5-methylpyrazine; 2-Ethenyl-6-methylpyrazine; 2-Ethyl-5-methylpyrazine; 2-Ethyl-6-methylpyrazine; 2-Ethyl-pyrazine; 2-Hydroxymethyl-5-methylpyrazine; 2-hydroxymethyl-5-methylpyrazine; 2-Hydroxymethyl-6-methylpyrazine; 2-Methoxy-5-methylpyrazine; 2-Methoxy-6-methylpyrazine; 2-Methyl-pyrazine; 2-Methyl-pyridine; 2-Pyrrolo-5-pyrazinecarboxyaldehyde; 2-Pyrrolo-6-pyrazinecarboxyaldehyde; 4,5-Methyl-imidazole; 4-methylimidazole; 5-Methyl-2-pyrazinecarboxyaldehyde; 6-Methyl-2-pyrazinecarboxyaldehyde; Acetamide; Acetate esters; Acetic acid; Acetol; Acetonitrile; Acetyl pyridine; Acetyl pyrrole; Acetyl-furane; Acetyl-pyrrole; Acid 3-ME-butanoic; Alkaloids; Ammonium bicarbonate; Ammonium carbonate; Anabasine; Anino-ME-Piperidione; Benzeneacetanide; Benzimidazole-N-ME-oxide; Benzonitrile; Bi-pyridyle; Carbon dioxide; Carbonyls; Cyan-ME-benzoic AC; Cyclohexanone+ET-PY; Cyclopentadione; Cyclotene; Di-ME-2,5-pyrazine; Di-ME-2,6-pyrazine; Di-ME-PH-Pyrazol; ET-3-ME-4-pyrrolidinone; ET-Pyrazine; ET-pyridine; ET-Pyrrole; Formaide; Furane carbonitrile; Furane-methanol; Furfural; Gama-butyrolactone; Hexadecanoic AC; Hydroquinone; Hydroxy-ME,-ME-pyrazine; Hydroxy-ME,-ME-pyrazine; Hydroxymethylpyrazine; Indole; Iso-cyano-benzene; Limonene; ME-2-phenol; ME-2-pyrazine; ME-2-pyridine; ME-3-cyclopentadione; ME-3-Furane; ME-3-pyridine; ME-3-Pyrrolidindione; ME-5-furfural; ME-Acetyl-pyrazine; ME-Cyclopentanone; ME-Furanyl pyrazine; ME-Hydroxy pyrrone; ME-Piperidinone; ME-Pyrrole; ME-pyrrolidinedione; ME-Pyrrolidinione; Methylpyrrolopyrazine; Mix ET-phenol; Myosmine; N,N-Di-ME-Acetamid; N-ME-pyrrole; Neophytodiene; Nicotine; Nicotyrine; Nitrogen; Phenol; Piperidinone; Piperidione; Polyhydroxylated alklyinidazole; Propenamide; Proprionic acid; Propylene glycol; Protoanemonin; Pyraidinecarbonitrile; Pyrazines; Pyridine; Pyridine acetonitrile; Pyridine-3-(Pyrrolidinyl); Pyridinecarboxamide; Pyridinol; Pyridoindole; Pyrrole; Pyrrolidindione; Pyrrolidinone; Pyruvaldehyde; Qunioxaline; Solanone; Spiro-heptanone; Tetrahyd-pyranone; Tri-ME-pyrazine; Trimethyl-pyrazine; Vinyl-benzene; Vinylpyridine (3-Vinylpyridine); Xylene (o- or p-Xylene)
Design Component: ACET; Ammonia technology-free reconstituted tobacco; Ammonium Carbonate Expanded Tobacco; ANSIRO; Band-cast reconstituted tobacco; Bright casing (Flue-cured casing); Bright tobacco (Flue-cured tobacco); Burley tobacco; Casing; CPCL; Dark tobacco; EMERGE; Flavorant; Flue-cured tobacco; Lamina; Nicotine transfer efficiency (NTE); Oriental tobacco (Turkish); PJS (PJ Schweitzer sheet); Expanded tobacco (Puffed tobacco, ET); RCB (Reconstituted cast blend)
Early PM @reconstituted_tobacco; Reconstituted tobacco; Strip application; Thermal processing
Operation/Project: Project GLOBE
Named Organization: American Tobacco Company; Brown & Williamson Tobacco Corporation (B&W)
Subsidiary of BAT U.S., located in Louisville, KY.; B.A.T. Industries PLC (BAT)
British American Tobacco Industry, parent company of Brown & Williamson Tobacco Co. in the U.S.; B.A.T. Cigarettenfabriken GmbH (B.A.T. Cigarettenfabriken GmbH)
B.A.T. Cigarettenfabriken GmbH; BAT-India; BATCF; BATUKE; Brazilian Ministry of Health; Brinckmann; Coca Cola; CYTREL; Fabriques de Tabac Reunies; Food and Agriculture Organization; JTI (Japan Tobacco Inc.)
Japan Tobacco Inc.; Kimberly-Clark Corp. (Specializes in the tobacco reconstitution process)
Specializes in the tobacco reconstitution process and in helping the tobacco companies control their nicotine; Liggett & Myers Inc. (Pioneer in the generic cigarette business)
Cigarette manufacturer; Pioneer in the generic cigarette business; L&M is the manufacturer of Chesterfield, Decade, Dorado, Duke of Durham in 1958, Eagle, Eve, L&M, Lark, Pyramid and Stride cigarettes; Lorillard Inc. (American cigarette manufacturer)
American cigarette manufacturer; Philip Morris Companies Inc. (Parent company of Philip Morris USA, Kraft, Miller)
America's seventh-largest industrial enterprise in 1993, owns Kraft, Miller Brewing, General Foods, and more.; R.J. Reynolds Tobacco Co. (Cigarette manufacturer (Camel, Winston, Doral))
Cigarette manufacturer (Camel, Winston, Doral); Reemtsma; Serfontein; Cia Souza Cruz Industria e Commercio (Souza Cruz) (Subsidiary of B.A.T. Industries Inc/. 1985)
1985 subsidiary of B.A.T. Industries Inc.; Technicon; World Health Organization (Concerned with global public health)
International organization concered with public health worldwide
Technology/Method: Argon flotation; Delta sensory panel method; DS scan technique; EBR process; Gas chromatography
Brand: Barclay KS; Benson & Hedges Menthol Lights 100 s; Cambridge Lights KS; Camel (RJR); Camel Filter; Camel Lights KS; Capri (PM); Carlton 100; Carlton 100 Menthol; Carlton 100 Rerun; Century 25; Doral (RJR); Doral Lights; Eli Cutter; Eve Lights 120; Generic Q FF 100; Generic Q FF 100 Menthol; Generic Q Lights 100; Harley Davidson; Hollywood; JPS; Kent Golden Lights 100 s; Kent Golden Lights Menthol 100 s; Kent III; Kool (BW (1933-2003)/RJR (2003-present))
First Menthol cigarette line, released in 1933. Premium priced brand.; Kool KS; Kool Milds 100; L&M KS; Lucky Strike (ATC (until 1996)/ BW (1996-2004)/ RJR (2004 on)); Malibu; Malibu 100 s Menthol; Malibu Full Flavor 100 s; Marlboro (PM); Marlboro KS; Marlboro KS Menthol; Max Menthol 120 s; Merit KS; Merit KS Menthol; MERIT ULTRA LIGHTS; Merit Ultra Lights 100 Menthol; MORE 120; More Menthol 120; Newport KS; Newport KS; Pall Mall Filter 100; Parliament lights 100 s; Parliament Lights KS; Richland KS; Richland Lights KS; Salem KS; Salem Ultra KS; True KS; True KS Menthol; Vantage KS; Vantage KS Menthol; Viceroy (bw); Virginia Slims (PM); Winston (RJR)
Subject: acids (additives); additives; Ammonia (Additives); Ammoniation (Technology); Cocoa (Additives); Expanded Tobacco (Design); Filters (Design); health effects; Humectants; Irritation (Effects); Licorice (Additives); Paper (Design); pH Manipulation (Technology); Product Aging (Design); Puff Parameters (Measures); Reconstituted Tobacco (Design); Sensory Effects—Impact (Effects); Sensory Effects—Taste (Effects); Smoke Nicotine (Measures); Smoke pH (Measures); Smoothness/Harshness (Effects); Sugars (Additives)
Glucose/Invert Sugar/Fructose/Sucrose; Tar (Measures); Test/Animal Subject (Testing); Test/Inhalation (Testing); Test/Reverse Engineering (Testing); Transfer to Smoke (Measures)

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BROWN & WILLIA~0N TOBACCO CORPORATION RESEARCH DEPARTMENT _RESTRICTED R&D-B032-89 A~ONIA TECHNOLOGY CONFERENCE MINUTES LOUISVILLE, KENTUCKY MAY 18-19, i989 Prepared by: DR. R° R. JOHNSON June 12, 1989 Svxm~ary and Text Mr. E. E. Kohnhorst Dr. J. S. Wigand Mr. A. L. Heard Mr* ~. Rittersha~s Full Document Dr. R. Binns (2) Dr. E. Kausch (2) Dr. C. J. P. de Siquelra (2) Mr, G. C. McGregor Dr. P. J. Dunn DISTRIBUTION Mr. T. F. Riehl Mr. M. L. Reynolds Dr. J. N. Jewell Mr. H. C: Woertz Mr. C. G. Lamb Dr. J. R. Lauterbach Dr. R. R. Johnson Dr. B. B. Chakraborty Mr. K. A. Zipperle Library (2) Issued by: Mr. H. L. Reynolds Project Number: 495 Copy Number:

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RESTRICTED BRQWN & WILLIANSON TOBACCO CORPORATION Research Depar tmen~ R&D-~32-89 A~NIA TECF~OLOG]~ CONFERENCE ~{INUTE3 LOUISVILLE, K~CKY ~AY 18-19, 1989 pArTICIPANTS BATCF De. Weber Hass Mr. Heuk C. ~eue BAT~<E Mr. Steve R. Hemsley Se~a C~z Dr. ~tonlo A. S. Rodri~ue~ Mr. M. Lance Reymolds Mr. E° D~mp Afford Dr. lolul H. Lauterbach Dr. Paul L. Aulbach Dr. Bara~ B. Chakraborty Dr. Robert R, Johnson Dr, Elmer F, Litzinser Dr. Serban C, Moldoveanu 8r. Kenneth N. Walker Mr. Kevlu A° Zipperle Mr. Arthur C, DiesinE

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Page 2 R&D-B032-89 EXECUTIVE SUI~4AR¥ The objectives of this conference were to: 1) Share information about the importance and use of ammonla technology (AT) worldwide. 2) Dete~ne opportunities to accelerate AT application. 3) Define ~eeded research go fill knowledge gaps. 4) Discuss areas of possible collaboratlve research. AT is the key to co=petlng in smoke quallty with PM worldwide. All U.$. man~actuxers except Liggett use some fern of AT on some clgarette products° Its widespread use by PM has led the consumer to associate AT ~th good tobacco taste. AT has at least two different facets: 1) productiou of flavors and/or flavor precur$ors~ and 2) reduction of harshness. B&W has been successful in developing AT cigarette products via. reconstituted tobacco and is actively p~rsuing second generatlon vehicles with urea. $ouza Cruz ha~ developed an AT Virgln£a easing (ANSIR0) ~nd is now explorlng its con~ercializatlon. BATCF is employing AT reaction flavors, and is wo~ing towards commecclalizatiou of an AT ¢as~g (E~GE) fo~ ste=s. Thus, as a group we axe active indeveloping AT that is usable under any of the cL~cren~ ~rldwtde re~latory constraints. However, resource levels used, excep~ at B&W, are small ~ relation to the need. A~ter $u~reyitlg the present status, our reconmnendations are: Continue active development of eon~nereial cigarettes wi~h AT. In particular we need to determine the extent to which a eomblnatlon of ANSIRO and E~RGE can be used to replace bandeast recon. b~other i==edlate need is to assess the compatibili~of AT with charcoal filter cigarettes. Better define what AT does to improve cigarette ~s~el and its llmitatlons. We need to define ~he ~mpor~an~e of application site and effects o~ process conditions. Par~ of ~his effo~ is development of relevant analy~iea~ ~thod~ for control of AT. Use this tmdersta~zding to develop AT flavorant$/casi~s/processes that can he u~ed worldwide. Consider the long term necessity of developing a natural ammonia source; e.g.. via. =~¢rebtal treat=e~ts. 5201)414S5

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Page 3 R~D-B032-89 S~Y OF PROGRAM AND DISCUSSIONS Current Usage of Ammonia in the Tobacco Industry - BAT and Competitive Mr. Lance Reynolds welcomed the delegates and set the stage by summarizing the U.$. market experience (Appendix A). The U.S. cigarette industry uses about ten million pounds of ammonia compounds a year. This correspoRds to about l0 of ancaonia compounds per cigarette produced. RJR alone has ~mmonla emissions of 900,000 Ibs/year in North Carolina. Five of the six major U.S. cigarette manufacturers use AT in at least some of their products. Liggett is the one holdout. AT has been essential in B&W's successful development of nonmenthol cigarette products at or above parity with PH brands. Dr. Baran Chakrabcrty presented the first paper (Appendix E) describing "Ammonia Disposition in Marlboro". This paper described the findings and observations over the years that led to a major effort on ammonia technology (AT) at B&W. The final part of the paper presented a hypothetical model of how AT acts to produce superior cigarette products. The main effects are: Enhanced ~atural flavor/body via. formation of volatile nitrogen flavorants. Improved nicotine transfer. Reduced irritation via. scavenging of irritants and buffering. Superior paper recon (sensory/physical) by urea addition. Dr, Chakraborty also presented the second paper (Appendix C), "Usage of Ammonia at B&W", This paper described the development oP CPCL and EER with emphasis on the smoke sensory methods used to optimize these reconstituted tobacco products. He then proceeded to outline the work we have now started to develop second generation AT reconstituted tobaccos with urea. Mr. Demp Alford presented the next paper (Appendix D), "Usage of Ammonia in Other U.S. Competitive Brands." This paper describes what we have learned so far using the DS scan technique to visualize AT effects on paper reconstituted tobaccos. The scans teach us: Which brands use AT ~d which do not. PM does not use AT in their new menthol cigarette products, but continues to use it in their older menthol brands and all nonmenthol brands exerted. G20'J414 G

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Page 4 R&D-B032-89 RJR uses AT, hut not through DAP. The experimental results agree with competitive intelligence that RJR uses direct treatment of reconstituted tobacco with ammonia gas. Some major D$ scan changes coincided with PM's stepwise increases in urea levels. The pyroglutamic acid peak appears associated with ~rea usage, and also suggests possible urea use by Liggett (?). Lorillard's tenon about matches EBR in DAP level. Their prior tenon showed no sigu of AT. Interestingly, our first finding of urea in a U.S. brand was several years ago in iorilla~d's Kent III. American uses DAP in Malihu, hut not in their older cigarette brands. Dr. Antonio Rodrigues then described (Appendix E) "Usage of A.~onia by Souza Cruz". This paper describes development of their cigarette brand Hollywood in an export versiou to compete with U.S. Marlboro. The essential feature are: Souza Cruz uses neither reconstituted tobacco nor puffed tobacco, SO they selected Virginia side casings for AT incorporation. Cut tobacco drying temperatures must not exceed 60~C or the effect is lost. Using Delta sensory panel methods, Souza Cruz was able to match U.S. Marlboro in two steps. The first and largest step was to use a OAP/ga=ana casing (ANSIRO) on the flue-cured side of the blend. The final match with Marlboro was achieved by adding an oriental flavor. Mr. Bank Koene presented a paper without slides (Appendix F), "Usage of Ammonia at BATCF". The highlights are: BATCF now uses AT flavors in commercial cigarettes. They are doing considerable work to develop cigarette products with AT via. stems. S~ce they cannot use DAP~ they use ammonium salts of acids native to tohacco, such as citric and melie acids. This mix is applied as a stem casing formulation (EMERGE), and results in large henefinial taste effects (see later). EMERGE also contains a polysaccharlde to prevent crystallization of the a~onium salts during cold weather. This polysac~baride and large amounts of natural citric and mallc acids in tobacco make E~GE a difficult casing to reverse engineer. BATCF has set ~M's m~-ximumblend ammonia level (0.23%) as their maximum in development work. 6;~09414S7

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Page 5 R&D-B032-89 Dr. Werner gass then presented "Usage of Ammonia by PM Europe and Othar Competitors", (Kppe~di~ G). The flndi~gs are~ PM uses band-cast recons where they can, and paper recons in all Marlboro versions. No band-cast is used in Germany or Spain. Deoxyfructosazine (OF) levels are elevated in the Marlboros. However, stems also have high DF levels with level depending markedly on stem grade. PM brands have the highest ammonia levels in the German market. Camel (KJR) has levels slightly above the brands without AT. A~.omia Usage - Discussion This largely resulted in a long list of questions that need a~swering, fi&W's interest was paramo~b because of it's large export and licensee business. The q~estlons are: What exactly is the RSR AT process? What does Project GLOBE tell us about whet RJR is doing worldwide? Is PM usiag urea in any off-shore markets? Does PN treat flue-cured with ammonia? Is PM still using ammonium carhosate puffed tobacco (ACET) in auy margets? What can we learn from smoke scans of old and ~ew Marlboro? • Is PM using AT in Japan? Is JTI? Is AT compatible with charcoal filters? • ~ we have current update o~ PM ammonia patents worldwlde~ What are we free to do? Wha~ should be the role of ANSIRO in markets allowing phosphate? It also became apparent that B&W needs to reevaluate the possible use of AT in menthol cigarettes. PM and Lorillard are selling lots of cigarettes with DAP, and B&W even has it (Egg) ou CAPRI. Are the bad sensory e£fects of gAP we see on KOOL due to our strip blend, due to phosphate, or due to ammonia? Effects of A~nia on Blends, Casings~ and S~ke Chemistry DE. Wez%ler Hass started off thls session with a paper (Append~ H), "Bffects of A~nia on Nicotine Distrlb~tic~1 in Cigarette Blends". This paper prese~Ded res~l~s o~ studies i~ which £i~-.z~red or oziental tobaccos and hurley o~ different a~on~ and nicotine contents were mixed and allowed to stand for vardous time ~erlods. Then, the tobaccos were separated a~d analyzed. ReJults a~e: Both a~onia and nlcotine transfer readily, a~onda faster. 6209414~S The dir~ctio~ of transfer depends on the molar imbalance. I

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Page 6 RhD-B032-89 RCB exhibits nicotine scavenging due to i~s eaozmou~ ammonia content. Are the ammonia reactions after transfer the chemical basi~ of blending sensory effects? Does redz~fing force such reactions to completion? Dr. Serban Moldoveanu presented the next paper (Appendix I) entitled "Pyrolysis Of Sugar-~muonia Reaction Products". The importance of this paper is that it is our entry into effects of AT on smoke chemistry. The major findings are: Reactions between asm~onia and reducing sugars initially forms deoxyfructosazines and polymers (~W ~ 1 - 10M). These give different product mixes on pyrolysis. Pyrolysis products from the polymer have many similarities to nitrogenous smoke components from burley tobacco. l~ pyrolysis products~ the dark polymers in combination with an AT-free recon (PJS) appear to give m%tch the same mim as CPCL. Mr. Honk Koen~ presented the last paper of this session (Appendix J), "Effects of AEmonia on Smoke Taste". His conclusions are: The secret of Marlboro is Ammonia. #~mnonla ~oes many good things. Marlboro~ far example, gives a lot of good flavor with no saturatlou. Aiso, i~ markedly reduces the cigarette hanKover effect, the bad aftertaste after a long prior evening of smoking too much. While recon is the obvious place to practice AT, it also leads to a big improvement in stem taste. When using AT, lower hurley grades become more usable. While AT leads to more taste and a more ha=oral taste, these benefits are only realized when it is applied properly. There is a great deal of product development yet to be done. ~mnonia Effects - Discussion The consistent theme throughout this session is that AT produces the good ~atural flavor Of burley without any of burley's bad taste effects. Bnt, this is only real~zed when AT is done right. Some further comments/suggestions are: While B&W can ~w mimic Marlboro's taste properties, we have not yet matched Marlboro's impact. We hope that second generation AT reoons with urea will lead to this benefit. BATCF's AT stem~ scavenge nicotine f~om other blend comp~ents. We need to pyrolyze ANSIEO and a/~onia cara~el. G 09414

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Page 7 R&D-B032-89 A high natural a~onia source may prove very useful for dewelopm~nt of AT casings. It was noted that B&W has an old patent (1976) claiming urea as casing ~dditive ~ ~k¢ flu¢-~ured t~haccc taste more like a blend. Low levels of ammonia added to whole smoke provide some beneficial taste effects. Probably need AT recsn to produce the optimum AT cigarette, The ammonia effect is much larger tb~tn the redryer effect. PM redries in Eccope. RJR may be redrying in Europe now. PM's band-east recon has more acetamlde than CPCL. Alsot other flavor scan (PT) shows Marlboro to be high in acetate esters, How does acetate fit in with AT? Chemistries Associated with the Usage of Az~onla The one formal paper in this session, "Pyrazine freoursors"~ was ~reseuted by D=. Antonio Ro~ri~ues. The comglete manuscript is contained in Appendix K. Important teachings are: &~mo,ium hydroxide and DAP lead to greatly different mixes of the same products when reacted with sugars. The DAP ~ix of products provides better sensor~ cu cigarettes. This enters a regulated area of food additives; 200 mg/kg ammonia caramel is thamaximumallowed in Brazil. Other industries using AT, ~articularly Coca Cola Co., have already done and published some of the detailed chemistry. Discussion - Urea as a Blend Add~tlve U~ea is a sepaEate part of AT. The 0.S. industry use is high, corresponding ~ ah~t ~ i~ all of PM's paper retort. Uther pelnts: Urea does not stand out in routine tobacco analyses. You have to look for it. The analytical scheme is difficult and requires sophisticated equ/p~ent; B&W uses GC/M~ with triply labelled urea internal standacd. Subsequently, we have learned that Technicon have provlded ~ autoanalyzer method to one U.S. company. gou will sever find all of the urea you added to tobacco. The typical p~oduct analysis show~ about half the added amount. Urea migrates between blend components, yet is site specific i~ sensory effects. 6209414DO -- I

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Page 8 R&D-BO32-89 There is a history use of urea in cigarette products: Estimated 2~ urea in for~t~atlon for PM's current paper recon. Fizst fo~d in Kent III iu the ~.g.A. BAT-India once used urea on paper filters to reduce paper taste. CYTREL contained about ~ urea to reduce paper taste. Thus, it passed the regulatory hurdle of the Hunter Committee. ~W work on C~gL-type materials showed large taste benefits from urea. NO urea is found in two ~ cigarettes, Winston and Doral. B&W is currently conducting a patent review/search with respect to use of urea in cigarette products, Those we know about now are: $erfontein B&W - urea added to flue-cured to impart blended taste. Kimbecly Clark - urea pl~s fatty acids in reeon. One theory has urea acting to impa~t ammonia iato smoke in the hot zone where it will scavenge c~rbonyl irritants, thereby forming desirable pyrazine flavors, gut, we doubt if this is the whole story o~urea~ b~mnonla Chemistries - Discussion To ~&W an obvious target is a stable of good and unregulated AT casings made ~rem unregulated materials~ and which can be used worldwide. Ideally, several different AT chemistries would he included in this casings toolbox to achieve different smoke sensory targets. ~hat unregul~ted materials? What is a good source of nat~al a~nia? Mr. Steve Hemsley provided a list of 34 abstracts from PM patents dealing vith a,~.ouia processii~K (Appen4ix L). It is apparent that there are several different ao~onia ch~istries involved, Ammonia with sugars produces simple molecules, some good tasting, some poor tasting, and some regulated~ and also polymers. What we~eed to know is: Specific anion effects. Is ammonium ci~rate/malate (~24ERGE) an e~ective replace~nt for DAP? How can we follow these reactions analytically? GZO9414DI

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Page 9 R&D-B032-89 ~hat AT is going on in other's 18mina? DS scans of single dark strands of tobacco ~rom Marlboro show that they are flue-cured or oriental with very high DF level. What can we accomplish by substituting amino acids for ammonia? The literature suggests that improvements are possible. In this connection, gouza Cruz finds some interesting non-tobacco flavors in their ANSIRO-type products. Current and Future Regulatory Barriers to the Usage of Ammonia Mr. Art Diesing presented slides (Appendix M) outlining worldwide regulatory restrictions on use of tobacco additives. Mr. Steve Hemsleyadded depth to this discussion from the AGP perspective. Four factors emerged: In a given country, those tobacco additives historically used in that country are generally approved. There are some exceptions, such as coumarln. Some countries also include food additives restrietion~ to the tobacco restrictions lists. Except for flavor form~latioRs, most countries are refuslng to add anything to their allowed lists. This is being done by ignoring all requests to add materials. The merged European market due on 12/31/92 will probably force the merging of regulatory restrictions on tobacco additives. Urea and DAP were specifically covered in this presentation. Urea is not allowed in Portugal or Spain, but is allowed in France for use on recon only. Also, urea has been identified as a naturally occurring material is tobacco. DAP is not allowed in Germany, Austria, or Spain. 0238F 6ZO9414D2

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