A Comparative Study on the Formation of Nitrosamines of Ethanolamines
- Corresponding author: FANG Yun, yunfang@126.com
Citation:
HU Xueyi, LUO Minmin, FANG Yun, LI Junguo, SUN Yang, LI Huashan. A Comparative Study on the Formation of Nitrosamines of Ethanolamines[J]. Chinese Journal of Applied Chemistry,
;2019, 36(9): 1061-1068.
doi:
10.11944/j.issn.1000-0518.2019.09.190029
ZHAN Li, ZHAN Lishi, WAN Li. In vivo Micronuclei and Gene Mutation Induced by DEN in the lacZ Transgenic Mouse[J]. J Hygiene Res, 2005,34(3):269-271. doi: 10.3969/j.issn.1000-8020.2005.03.005
HUI Zhiyu, XU Yang, ZHU Jianhua. Removal of N-Nitrosamine from Cigarette Smoke by Zeolite[J]. Chinese J Appl Chem, 2002,19(3):276-279. doi: 10.3969/j.issn.1000-0518.2002.03.017
Seweryn A, Wasilewski T, Bujak T. Effect of Salt on the Manufacturing and Properties of Hand Dishwashing Liquids in the Coacervate Form[J]. Ind Eng Chem Res, 2016,55(4):1134-1141. doi: 10.1021/acs.iecr.5b04048
Sikora E, Sliwa K, Ogonowki J. Study of Properties of Shampoos Containing Whey of Cow Milk[J]. SOFW J, 2011,137(6):14-20.
Abd R M, Nour A H, Sulaiman A Z. Kinetic Stability and Rheology of Water-in-Crude Oil Emulsion Stabilized by Cocamide at Different Water Volume Fractions[J]. Int J Chem Eng Appl, 2014,5(2):204-209.
Wasilewski T. Coacervates as a Modern Delivery System of Hand Dishwashing Liquids[J]. J Surfactants Deterg, 2010,13(4):513-520. doi: 10.1007/s11743-010-1189-4
Program N T. Toxicology and Carcinogenesis Studies of Coconut Oil Acid Diethanolamine Condensate(CAS No. 68603-42-9) in F344/N Rats and B6C3F1 Mice(Dermal Studies)[J]. NTP Tech Rep, 2001,479:5-226.
Havery D C, Chou H J. Nitrosamines in Sunscreens and Cosmetic Products[C]. ACS Symp Ser, 1994.
Andersen F A. Amended Final Report on the Safety Assessment of Cocamide DEA[J]. J Am Coll Toxicol, 1996,15(6):527-542. doi: 10.3109/10915819609008729
Fiume M M, Heldreth B, Bergfeld W F. Safety Assessment of Diethanolamides as Used in Cosmetics[J]. Int J Toxicol, 2013,32(3 Suppl):36S-58S.
HUANG Xiaodong, LI Yuhong, DAI Congjie. Evaluation in vitro of Scavenging Effect on Nitrite and Interdicting Effect on Nitrosamine Synthesis of Extract from Aegiceras corniculatum[J]. J Chinese Inst Food Sci Tech, 2015,15(9):15-22.
LI ling, ZHANG Cuan, ZHOU Guanghong. Effects of Polyphenols on the Nitrite Scavenging and N-Nitrosamine Formation in Simulated Gastric Acid[J]. J Nanjing Agric Univ, 2013,36(3):111-116. doi: 10.7685/j.issn.1000-2030.2013.03.019
Dai N, Mitch W A. Influence of Amine Structural Characteristics on N-Nitrosamine Formation Potential Relevant to Postcombustion CO2 Capture Systems[J]. Environ Sci Technol, 2013,47(22):13175-13183. doi: 10.1021/es4035396
Sun Z, Liu Y D, Zhong R. Theoretical Investigation of Reactivities of Amines in the N-Nitrosation Reactions by N2O3[J]. J Mol Model, 2011,17(4):669-680. doi: 10.1007/s00894-010-0750-4
Abedi G, Talebpour Z. Modified QuEChERS as a Novel Sample Preparation Method for Analysis of N-Nitrosodiethanolamine in Shampoo by High Performance Liquid Chromatography[J]. Anal Methods, 2017,9(35):5165-5173. doi: 10.1039/C7AY01378G
Bhangare R C, Sahu S K, Pandit G G. Nitrosamines in Seafood and Study on the Effects of Storage in Refrigerator[J]. J Food Sci Technol, 2013,52(1):507-513.
Lim D S, Roh T H, Kim M K. Risk Assessment of N-Nitrosodiethylamine(NDEA) and N-Nitrosodiethanolamine(NDELA) in Cosmetics[J]. J Toxicol Environ Health, Part A, 2018,81(12):465-480. doi: 10.1080/15287394.2018.1460782
Sabate C M, Delalu H. Synthesis and Characterization of Secondary Nitrosamines from Secondary Amines Using Sodium Nitrite and p-Toluenesulfonic Acid[J]. Chem Asian J, 2015,10(3):674-678. doi: 10.1002/asia.201403182
Sakai N, Sasaki M, Ogiwara Y. Copper(Ⅱ)-Catalyzed Oxidative N-nitrosation of Secondary and Tertiary Amines with Nitromethane under an Oxygen Atmosphere[J]. Chem Commun(Cambridge U K), 2015,51(58):11638-11641. doi: 10.1039/C5CC03675E
Chaudhary P, Gupta S, Muniyappan N. An Efficient Synthesis of N-Nitrosamines under Solvent, Metal and Acid Free Conditions Using tert-Butyl Nitrite[J]. Green Chem, 2016,18(8):2323-2330. doi: 10.1039/C5GC02880A
Hsu J, Arcot J, Alice Lee N. Nitrate and Nitrite Quantification from Cured Meat and Vegetables and Their Estimated Dietary Intake in Australians[J]. Food Chem, 2009,115(1):334-339. doi: 10.1016/j.foodchem.2008.11.081
Goudarziafshar H, Ghorbani-Choghamarani A, Hadian L. N-Nitrosation of Secondary Amines Using Supported Perchloric Acid on Silica Gel and Stereoselectivity Study of Nitroso Products[J]. J Chinese Chem Soc, 2013,60(10):1272-1276. doi: 10.1002/jccs.201300136
Lazny R, Nodzewska A, Wolosewicz K. New Simple Polymeric Supports with Hydrazone Linkers for Solid-Phase Synthesis of Ketones and Primary Amines[J]. Synthesis, 2003,18(18):2858-2864.
Zhang J, Jiang J, Li Y. Iodide-Catalyzed Synthesis of N-Nitrosamines via C-N Cleavage of Nitromethane[J]. J Org Chem, 2013,78(22):11366-11372. doi: 10.1021/jo401915t
Ridd J H. Nitrosation, Diazotisation, and Deamination[J]. Q Rev Chem Soc, 1961,15(4):418-441. doi: 10.1039/qr9611500418
Da Silva E F, Lepaumier H, Grimstvedt A. Understanding 2-Ethanolamine Degradation in Postcombustion CO2 Capture[J]. Ind Eng Chem Res, 2012,51(41):13329-13338. doi: 10.1021/ie300718a
Fan T Y, Tannenbaum S R. Factors Influencing the Rate of Formation of Nitrosomorpholine from Morpholine and Nitrite:Acceleration by Thiocyanate and other Anions[J]. J Agric Food Chem, 1973,21(2):237-240. doi: 10.1021/jf60186a006
Mirvish S S. Kinetics of Dimethylamine Nitrosation in Relation to Nitrosamine Carcinogenesis[J]. J Natl Cancer Inst, 1970,44(3):633-639.
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A.FT-IR; B.ESI-MS; C.1H NMR(DMSO); D.13C NMR(101 MHz, CDCl3)
A.FT-IR; B.ESI-MS; C.1H NMR(DMSO); D.13C NMR(101 MHz, DMSO)
A.FT-IR:a.nitrosation product of monoethanolamine; b. N-nitrosodiethanolamine; B.UPLC:a.nitrosation product of monoethanolamine; b.N-nitrosodiethanolamine; c.nitrosation reaction mixture of monoethanolamine
a.diethanolamine in ethanol(mass fraction of 0.022%); b.monoethanolamine in ethanol