Selective reduction of tobacco-specific nitrosamines and related methods

Patent metadata

Field	Value
Publication number	US-10383357-B2
Application number	US-201715592160-A
Country	US
Kind code	B2
Filing date	May 10, 2017
Priority date	May 10, 2016
Publication date	Aug 20, 2019
Grant date	Aug 20, 2019

Abstract

Aspects of the present disclosure relate to electrochemical reduction of tobacco-specific nitrosamines (TSNAs). According to certain methods described herein, a tobacco composition containing one or more TSNAs and nicotine is contacted with a solvent to form a tobacco mixture. In some embodiments, the tobacco mixture is introduced into an electrochemical device comprising an anode and a cathode. The tobacco mixture may, in some cases, form at least part of an initial electrolyte mixture that is in physical contact with at least a portion of the anode and at least a portion of the cathode. In some instances, an electrical potential is applied between the anode and the cathode, thereby reducing one or more TSNAs in the initial electrolyte mixture and producing a reduced electrolyte mixture. In certain cases, application of the electrical potential between the anode and the cathode does not cause non-TSNA components of the tobacco mixture (e.g., nicotine) to undergo electrochemical reduction or any other chemical reaction.

First claim

What is claimed is:

1. A method for reducing a tobacco-specific nitrosamine, comprising:
contacting an initial electrolyte mixture with an anode and a cathode, wherein the initial electrolyte mixture comprises nicotine, the tobacco-specific nitrosamine, a dissolved salt, and at least one solvent; and
applying an electrical potential between the anode and the cathode to form a reduced electrolyte mixture, wherein a concentration of the tobacco-specific nitrosamine in the reduced electrolyte mixture is lower than a concentration of the tobacco-specific nitrosamine in the initial electrolyte mixture.

2. The method of claim 1 , further comprising contacting a tobacco composition comprising nicotine and the tobacco-specific nitrosamine with at least one solvent to form a tobacco mixture, wherein the tobacco mixture forms at least part of the initial electrolyte mixture.

3. The method of claim 1 , wherein the tobacco-specific nitrosamine is 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) or N-nitrosonornicotine (NNN).

4. The method of 1 , wherein the concentration of the tobacco-specific nitrosamine in the initial electrolyte mixture is in a range from about 10 μg/L to about 0.5 g/L.

5. The method of claim 1 , wherein the concentration of the tobacco-specific nitrosamine in the reduced electrolyte mixture is about 0.001 g/L or less.

6. The method of claim 1 , wherein a difference between the concentration of the tobacco-specific nitrosamine in the initial electrolyte mixture and the concentration of the tobacco-specific nitrosamine in the reduced electrolyte mixture is at least about 0.001 g/L.

7. The method of claim 1 , wherein the initial electrolyte mixture and the reduced electrolyte mixture have a nicotine concentration in a range from about 0.01 g/L to about 100 g/L.

8. The method of claim 1 , wherein the initial electrolyte mixture has a pH of about 2.0 or less.

9. The method of claim 1 , wherein the initial electrolyte mixture and the reduced electrolyte mixture have a temperature between about 20° C. and about 25° C.

10. The method of claim 1 , wherein the cathode comprises an electrocatalyst and carbon nanotubes, wherein the electrocatalyst comprises an organometallic complex.

11. The method of claim 10 , wherein the organometallic complex is a metal porphyrin complex, a metal phthalocyanine complex, or a metalloenzyme.

12. The method of claim 11 , wherein the metal porphyrin complex comprises hemin, iron porphyrin, iron(II)(porphyrinato)(imidazole), a heme protein, or a combination of two or more of the foregoing.

13. The method of claim 11 , wherein the organometallic complex comprises iron.

14. The method of claim 11 , wherein the metalloenzyme is carbon monoxide dehydrogenase.

15. The method of claim 1 , wherein the electrical potential is in a range between about −0.5 V and about −5 V.

16. The method of claim 1 , wherein the electrical potential is applied between the anode and the cathode for a time period between about 5 minutes and about 15 minutes.

17. A tobacco substrate comprising the reduced electrolyte mixture formed by the method of claim 1 , wherein the reduced electrolyte mixture comprises a reduced species of the tobacco-specific nitrosamine.

18. A smoking article comprising a tobacco substrate, said tobacco substrate comprising the reduced electrolyte mixture formed by the method of claim 1 , wherein the reduced electrolyte mixture comprises a reduced species of the tobacco-specific nitrosamine.

19. The method of claim 1 , wherein the reduced electrolyte mixture comprises a reduced species of the tobacco-specific nitrosamine.

20. The method of claim 19 , wherein the reduced species is an amine or a hydrazine.

Assignees

• Massachusetts Inst Technology

Inventors

• Bromberg Lev E
• Su Xiao
• Hatton Trevor Alan

Classifications

• A24B15/245 Primary

  Nitrosamines · CPC title

• A24B15/22

  by application of electric or wave energy or particle radiation · CPC title