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DETERMINATION OF CARBONYL
COMPOUND GENERATED FROM
ELECTRONIC NICOTINE DELIVERY
SYSTEMS
By: Madison Parker
1
2
E.N.D.S
Cartidge-nicotine and Propylene Glycol
mixture
Battery-atomizes liquid
Powered when user inhales
Each system contains a battery,
atomizer, and cartridge
3
SECOND GENERATION
4
ATOMIZERS
5
THIRD GENERATION
6
7
PROPYLENE GLYCOL
 Generated by propylene oxide
 Odorless
 Low viscosity
 Colorless
 Preserve food, solvents, pharmaceuticals
8
VEGETABLE GLYCERIN
 Naturally extracted plant oils
 Coconut oil, palm oil, soy
 Odorless
 Tinted color
 Sweet smelling
 More viscous than propylene glycol
9
NICOTINE
 Dependent drug
 Can cause feeling of irritability,
depression, and anxiety
 Used in liquid form
 Concentrations vary between 0-18
mg/ml
10
CHEMICAL REACTION THROUGH WHICH
PROPYLENE GLYCOL/GLYCERIN FORMS
ALDEHYDES
Glycerin
 C3H8O3 ∆ C2H3CHO + 2H2O
 C3H4O 𝑯+ H3CCHO + HCHO
 C3H4O 𝒉𝒐𝒕 𝒎𝒆𝒕𝒂𝒍
H3CCHO + HCHO
Propylene Glycol
 C3H8O2 −𝑯 𝟐
𝑶
C2H5CHO
11
Acrolein
Acetylaldehyde Formaldehyde
Acetylaldehyde Formaldehyde
Propionaldehyde
Acrolein
12
AFFECT OF ALDEHYDES ON THE BODY
 Acrolein is the simplest carbonyl
compound and the most toxic!
 Occupational exposure-olfactory and
ocular irriation
 Long-term contact-extreme irritation
mucous membranes and respiratory
damage
 Chronic exposure-irreversible damage
to tissue lining in the respiratory tract
 Rat study:
103 ratsformaldehyde cell
carcinoma
Mice  formaldehyde  nasal
tumors
13
OVERVIEW OF OXIDATION OF GLYCEROL
AND PROPYLENE GLYCOL WITH NICHROME
WIRE CATALYST 14
MECHANISM OF GLYCEROL DEHYDRATION
REACTION TO CARBONYL COMPOUNDS
15
16
MECHANISM OF PROPYLENE GLYCOL
DEHYDRATION TO CARBONYL COMPOUNDS
17
18
DETERMINATION OF CARBONYL
COMPOUNDS GENERATED FROM E-
CIGARETTES BY HPLC
19
Carbonyl compounds found in
e-cigarette vapors
20
CONCENTRATIONS OF CARBONYL
COMPOUNDS FOUND IN 10 E-CIGARETTES 21
Concentrations of key carbonyl compounds that were produced from 13 e-cigarette brands tested 22
THERMAL DEGRADATION OF NICHROME
WIRE CATALYST
23
THE EFFECT OF NICOTINE SOLVENT AND BATTERY
OUTPUT VOLTAGE ON CARBONYL COMPOUNDS
PRESENT IN E-CIGARETTES
24
INGREDIENT LIST WITH
NICOTINE
CONCENTRATIONS FOR
E-LIQUIDS USED
25
CARBONYL COMPOUNDS FOUND IN 10
E-LIQUID SOLUTIONS
26
AFFECT OF BATTERY OUTPUT VOLTAGE
ON CARBONYL COMPOUND YIELDS
27
CONCLUSIONS
 At the high temperatures that are required to vaporize these solutions, unpredictable
behaviors among the compounds take place and carcinogenic carbonyl compounds are
being formed and inhaled
 The inconsistency of the carbonyl compounds that are formed from the e-cigarette vapors
suggests that at high temperatures there is a lot more interaction among the compounds
within the solvents.
 Increase in battery output voltage also proved that these toxic compounds can be
produced in extremely high concentrations.
 While it is known how the body is affected when these additives are consumed, it is not
known how the body is affected when these additives are inhaled. 28
FURTHER RESEARCH
 Research should be performed to determine the behaviors of e-cigarette users.
Experiments can be ran similarly to the e-cigarette user’s behavior so that results
are more comparable
 by standardizing the analysis of aerosol generation and collection of carbonyl
compounds, this would allow for better comparisons of e-cigarette aerosols and
cigarette smoke components.
29
REFERENCES
 VapeHit. E-liquid Facts. http://www.vapehit.co.uk/info.php?articles&articles_id=22 (accessed Oct. 25, 2015).
 Info Electronic Cigarette. Electronic Cigarette GLossery.http://info-electronic-cigarette.com/electronic-cigarette-glossary/(accessed Oct. 21,
2015).
 Eversmoke Electronic Cigarettes. History of the Electronic Cigarette. http://www.learn.eversmoke.com/history-of-electronic-cigarettes.html
(accessed Oct. 21, 2015).
 Nguyen, David and Aamodt Gail. Electronic Cigarettes the Past, Present, and Future. Continuing Education Course. DentalCare.com [Online]
(October 1 2014). http://www.dentalcare.com/media/en-US/education/ce451/ce451.pdf (Accessed Oct. 15, 2015)
 Sifferlin, Alexandra. E-cig Flavors May BE Dangerous, Study Says. Time. [Online] 2015. http://time.com/3822831/ecig-flavors/ (accessed Oct.
17, 2015)
 Medical News Today. What is Nicotine? http://www.medicalnewstoday.com/articles/240820.php (Accessed Oct. 18, 2015)
 Marnett, Lawrence J. Health Effects of Aldehydes and Alcohols in Mobile Source Emissions. In Air Pollution, the Automobile, and Public
Health. Washington, DC: The National Academies Press, 1988. pp 580-585. (http://www.nap.edu/read/1033/chapter/25#583) (accessed Oct.
18, 2015)
 Cassee, Flemming R; Groten, John P; Feron, Victor J. Changes in the Nasal Epithelium of Rates Exposed by Inhalation to Mixtures of
Formaldehyde, Acetaldehyde, and Acrolein. Fundamental and Applied Toxicology. [Online] 1995, 29, 208-218.
(http://toxsci.oxfordjournals.org/content/29/2/208.full.pdf+html) (accessed Oct. 23, 2015)
 Laino, Teodoro; Tuma, Christian; Moor, Philippe; Martin, Elyette; Stolz, Steffen; Curioni, Alessandro. Mechanisms of Propylene Glycol and
Triacetin Pyrolysis. J. Phys. Chem. A 2012, 116, 4602-4609 (http://eprints.eemcs.utwente.nl/22979/01/stolz1-jp300997d.pdf) (accessed Oct.
18, 2015)
 Ulgen, Arda. Conversion of Glycerol to the Valuable Intermediates Acrolein and Allyl Alcohol in the Presence of Heterogeneous Catalysts.
[online] (http://publications.rwth-aachen.de/record/63757/files/3078.pdf;) (accessed Oct. 19, 2015) 30
REFERENCES CONT.
 Uchiyama, Shigehisa; Ohta, Kuzushi; Inaba, Yohei; Kunugita, Naoki. Determination of Carbonyl Compounds Generated from the E-Cigarette
Using Coupled Silica Cartridges Impregnated with Hydroquinone and 2, 4-Dinitrophenylhydrazine, Followed by High-Performance Liquid
Chromatography. Analytical Sciences. December 2013, Vol. 29, 1219-1222.
 Kosmider PharmD, Leon; Sobczak PhD, Andrzej; Fik PharmD, Maciej; Knysak PharmD, Jakub; Zaciera PharmD, Marzena; Kurek PharmD,
Jolanta; Goniewicz PharmD, PhD, Maciej Lukasz. Carbonyl Compounds in Electronic Cigarette Vapors---Effects of Nicotine Solvent and
Battery Output Voltage. Nicotine & Tobacco Advance Access. May 14, 2014.
 Centers for Disease Control and Prevention. Nicotine: Systematic Agent.
http://www.cdc.gov/niosh/ershdb/emergencyresponsecard_29750028.html (accessed Oct. 17, 2015)
 Geiss, Otmar; Bianchi, Ivana; Barahona, Francisco; Barrero-Moreno, Josefa. Characterization of Mainstream and Passive Vapours Emitted by
Selected Electronic Cigarettes. International Journal of Hygiene and Environmental Health. Vol 218, Issue 1, January 2015, 172-180.
 Schlaf, Marcel; Zhang, Z. Conrad; Cellulose Hydrogenolysis to Ethylene Glycol and 1,2-Propylene Glycol. Reaction Pathways and Mechanisms
in Thermocatalytic Biomass Conversion I. Springer: New York, 2015; pp 242-247.
 Cheng, Tianrong. Chemical Evaluation of Electronic Cigarettes. Center for Tobacco Products, Food, and Drug Administration. [Online]. 2014,
23, ii11-ii17.
 Lim, Hyun-Hee; Shin, Ho-Sang. Measurement of Aldehydes in Replacement Liquids of Electronic Cigarettes by Headspace Gas
Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 2013, Vol. 34, No. 9. Pp. 2691-2695.
 Center for Disease Control and Prevention. Economic Facts About U.S. Tobacco Production and Use.
http://www.cdc.gov/tobacco/data_statistics/fact_sheets/economics/econ_facts/ (accessed Oct. 23, 2015)
 Forbes. E-Cigarette Sales Surpass $1 Billion As Big Tobacco Moves In. http://www.forbes.com/sites/natalierobehmed/2013/09/17/e-
cigarette-sales-surpass-1-billion-as-big-tobacco-moves-in/ (accessed Oct. 24, 2015)
 Forbes. E-Cigarette Flavoring Chemicals May Pose Risks When Inhaled. http://www.forbes.com/sites/tarahaelle/2015/04/16/e-cigarette-
flavoring-chemicals-may-pose-risks-when-inhaled/. (accessed Oct. 24, 2015).
31

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Determination of Carbonyl Compounds Found in Electronic Cigarettes

  • 1. DETERMINATION OF CARBONYL COMPOUND GENERATED FROM ELECTRONIC NICOTINE DELIVERY SYSTEMS By: Madison Parker 1
  • 2. 2
  • 3. E.N.D.S Cartidge-nicotine and Propylene Glycol mixture Battery-atomizes liquid Powered when user inhales Each system contains a battery, atomizer, and cartridge 3
  • 7. 7
  • 8. PROPYLENE GLYCOL  Generated by propylene oxide  Odorless  Low viscosity  Colorless  Preserve food, solvents, pharmaceuticals 8
  • 9. VEGETABLE GLYCERIN  Naturally extracted plant oils  Coconut oil, palm oil, soy  Odorless  Tinted color  Sweet smelling  More viscous than propylene glycol 9
  • 10. NICOTINE  Dependent drug  Can cause feeling of irritability, depression, and anxiety  Used in liquid form  Concentrations vary between 0-18 mg/ml 10
  • 11. CHEMICAL REACTION THROUGH WHICH PROPYLENE GLYCOL/GLYCERIN FORMS ALDEHYDES Glycerin  C3H8O3 ∆ C2H3CHO + 2H2O  C3H4O 𝑯+ H3CCHO + HCHO  C3H4O 𝒉𝒐𝒕 𝒎𝒆𝒕𝒂𝒍 H3CCHO + HCHO Propylene Glycol  C3H8O2 −𝑯 𝟐 𝑶 C2H5CHO 11 Acrolein Acetylaldehyde Formaldehyde Acetylaldehyde Formaldehyde Propionaldehyde
  • 13. AFFECT OF ALDEHYDES ON THE BODY  Acrolein is the simplest carbonyl compound and the most toxic!  Occupational exposure-olfactory and ocular irriation  Long-term contact-extreme irritation mucous membranes and respiratory damage  Chronic exposure-irreversible damage to tissue lining in the respiratory tract  Rat study: 103 ratsformaldehyde cell carcinoma Mice  formaldehyde  nasal tumors 13
  • 14. OVERVIEW OF OXIDATION OF GLYCEROL AND PROPYLENE GLYCOL WITH NICHROME WIRE CATALYST 14
  • 15. MECHANISM OF GLYCEROL DEHYDRATION REACTION TO CARBONYL COMPOUNDS 15
  • 16. 16
  • 17. MECHANISM OF PROPYLENE GLYCOL DEHYDRATION TO CARBONYL COMPOUNDS 17
  • 18. 18
  • 19. DETERMINATION OF CARBONYL COMPOUNDS GENERATED FROM E- CIGARETTES BY HPLC 19
  • 20. Carbonyl compounds found in e-cigarette vapors 20
  • 21. CONCENTRATIONS OF CARBONYL COMPOUNDS FOUND IN 10 E-CIGARETTES 21
  • 22. Concentrations of key carbonyl compounds that were produced from 13 e-cigarette brands tested 22
  • 23. THERMAL DEGRADATION OF NICHROME WIRE CATALYST 23
  • 24. THE EFFECT OF NICOTINE SOLVENT AND BATTERY OUTPUT VOLTAGE ON CARBONYL COMPOUNDS PRESENT IN E-CIGARETTES 24
  • 26. CARBONYL COMPOUNDS FOUND IN 10 E-LIQUID SOLUTIONS 26
  • 27. AFFECT OF BATTERY OUTPUT VOLTAGE ON CARBONYL COMPOUND YIELDS 27
  • 28. CONCLUSIONS  At the high temperatures that are required to vaporize these solutions, unpredictable behaviors among the compounds take place and carcinogenic carbonyl compounds are being formed and inhaled  The inconsistency of the carbonyl compounds that are formed from the e-cigarette vapors suggests that at high temperatures there is a lot more interaction among the compounds within the solvents.  Increase in battery output voltage also proved that these toxic compounds can be produced in extremely high concentrations.  While it is known how the body is affected when these additives are consumed, it is not known how the body is affected when these additives are inhaled. 28
  • 29. FURTHER RESEARCH  Research should be performed to determine the behaviors of e-cigarette users. Experiments can be ran similarly to the e-cigarette user’s behavior so that results are more comparable  by standardizing the analysis of aerosol generation and collection of carbonyl compounds, this would allow for better comparisons of e-cigarette aerosols and cigarette smoke components. 29
  • 30. REFERENCES  VapeHit. E-liquid Facts. http://www.vapehit.co.uk/info.php?articles&articles_id=22 (accessed Oct. 25, 2015).  Info Electronic Cigarette. Electronic Cigarette GLossery.http://info-electronic-cigarette.com/electronic-cigarette-glossary/(accessed Oct. 21, 2015).  Eversmoke Electronic Cigarettes. History of the Electronic Cigarette. http://www.learn.eversmoke.com/history-of-electronic-cigarettes.html (accessed Oct. 21, 2015).  Nguyen, David and Aamodt Gail. Electronic Cigarettes the Past, Present, and Future. Continuing Education Course. DentalCare.com [Online] (October 1 2014). http://www.dentalcare.com/media/en-US/education/ce451/ce451.pdf (Accessed Oct. 15, 2015)  Sifferlin, Alexandra. E-cig Flavors May BE Dangerous, Study Says. Time. [Online] 2015. http://time.com/3822831/ecig-flavors/ (accessed Oct. 17, 2015)  Medical News Today. What is Nicotine? http://www.medicalnewstoday.com/articles/240820.php (Accessed Oct. 18, 2015)  Marnett, Lawrence J. Health Effects of Aldehydes and Alcohols in Mobile Source Emissions. In Air Pollution, the Automobile, and Public Health. Washington, DC: The National Academies Press, 1988. pp 580-585. (http://www.nap.edu/read/1033/chapter/25#583) (accessed Oct. 18, 2015)  Cassee, Flemming R; Groten, John P; Feron, Victor J. Changes in the Nasal Epithelium of Rates Exposed by Inhalation to Mixtures of Formaldehyde, Acetaldehyde, and Acrolein. Fundamental and Applied Toxicology. [Online] 1995, 29, 208-218. (http://toxsci.oxfordjournals.org/content/29/2/208.full.pdf+html) (accessed Oct. 23, 2015)  Laino, Teodoro; Tuma, Christian; Moor, Philippe; Martin, Elyette; Stolz, Steffen; Curioni, Alessandro. Mechanisms of Propylene Glycol and Triacetin Pyrolysis. J. Phys. Chem. A 2012, 116, 4602-4609 (http://eprints.eemcs.utwente.nl/22979/01/stolz1-jp300997d.pdf) (accessed Oct. 18, 2015)  Ulgen, Arda. Conversion of Glycerol to the Valuable Intermediates Acrolein and Allyl Alcohol in the Presence of Heterogeneous Catalysts. [online] (http://publications.rwth-aachen.de/record/63757/files/3078.pdf;) (accessed Oct. 19, 2015) 30
  • 31. REFERENCES CONT.  Uchiyama, Shigehisa; Ohta, Kuzushi; Inaba, Yohei; Kunugita, Naoki. Determination of Carbonyl Compounds Generated from the E-Cigarette Using Coupled Silica Cartridges Impregnated with Hydroquinone and 2, 4-Dinitrophenylhydrazine, Followed by High-Performance Liquid Chromatography. Analytical Sciences. December 2013, Vol. 29, 1219-1222.  Kosmider PharmD, Leon; Sobczak PhD, Andrzej; Fik PharmD, Maciej; Knysak PharmD, Jakub; Zaciera PharmD, Marzena; Kurek PharmD, Jolanta; Goniewicz PharmD, PhD, Maciej Lukasz. Carbonyl Compounds in Electronic Cigarette Vapors---Effects of Nicotine Solvent and Battery Output Voltage. Nicotine & Tobacco Advance Access. May 14, 2014.  Centers for Disease Control and Prevention. Nicotine: Systematic Agent. http://www.cdc.gov/niosh/ershdb/emergencyresponsecard_29750028.html (accessed Oct. 17, 2015)  Geiss, Otmar; Bianchi, Ivana; Barahona, Francisco; Barrero-Moreno, Josefa. Characterization of Mainstream and Passive Vapours Emitted by Selected Electronic Cigarettes. International Journal of Hygiene and Environmental Health. Vol 218, Issue 1, January 2015, 172-180.  Schlaf, Marcel; Zhang, Z. Conrad; Cellulose Hydrogenolysis to Ethylene Glycol and 1,2-Propylene Glycol. Reaction Pathways and Mechanisms in Thermocatalytic Biomass Conversion I. Springer: New York, 2015; pp 242-247.  Cheng, Tianrong. Chemical Evaluation of Electronic Cigarettes. Center for Tobacco Products, Food, and Drug Administration. [Online]. 2014, 23, ii11-ii17.  Lim, Hyun-Hee; Shin, Ho-Sang. Measurement of Aldehydes in Replacement Liquids of Electronic Cigarettes by Headspace Gas Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 2013, Vol. 34, No. 9. Pp. 2691-2695.  Center for Disease Control and Prevention. Economic Facts About U.S. Tobacco Production and Use. http://www.cdc.gov/tobacco/data_statistics/fact_sheets/economics/econ_facts/ (accessed Oct. 23, 2015)  Forbes. E-Cigarette Sales Surpass $1 Billion As Big Tobacco Moves In. http://www.forbes.com/sites/natalierobehmed/2013/09/17/e- cigarette-sales-surpass-1-billion-as-big-tobacco-moves-in/ (accessed Oct. 24, 2015)  Forbes. E-Cigarette Flavoring Chemicals May Pose Risks When Inhaled. http://www.forbes.com/sites/tarahaelle/2015/04/16/e-cigarette- flavoring-chemicals-may-pose-risks-when-inhaled/. (accessed Oct. 24, 2015). 31