A Comparative Study on the Formation of Nitrosamines of Ethanolamines

doi:10.11944/j.issn.1000-0518.2019.09.190029

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (9): 1061-1068.DOI: 10.11944/j.issn.1000-0518.2019.09.190029

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A Comparative Study on the Formation of Nitrosamines of Ethanolamines

HU Xueyi^a,LUO Minmin^a,FANG Yun^a^*(),LI Junguo^b,SUN Yang^c,LI Huashan^c

^aKey Laboratory of Synthetic and Biological Colloids(Ministry of Education),School of Chemical and Material Engineering, Jiangnan University,Wuxi,Jiangsu 214122, China
^bJiangsu Qingting Washing Products Co., Ltd.,Yancheng,Jiangsu 224555,China
^cNanjing Huashi New Material Co., Ltd.,Nanjing 210044,China

Received:2019-01-25 Accepted:2019-04-10 Published:2019-09-05 Online:2019-09-05
Contact: Yun FANG
Supported by:
Supported by the National Key Research and Development Plan of China(No.2017YFB0308904)

Abstract

Abstract:

To investigate the reasonability and feasibility to substitute fatty acid diethanolamide by monoethanolamide and methylethanolamide in surfactant production and application, the nitrosation of methylethanolamine or monoethanolamine was compared with diethanolamine. In this study, nitrosamines were prepared from three ethanolamines by nitrosating agents of both tert-butyl nitrite and nitrous acid. The products of nitrosation by tert-butyl nitrite were identified to reveal nitrosation mechanisms, while the yields of the nitrosamines formed by nitrous acid were used to evaluate the easiness of nitrosation among three ethanolamines. Mechanism analysis of nitrosation shows that diethanolamine or methylethanolamine forms the corresponding nitrosamines, while monoethanolamine solely forms trace amount of N-nitroso-diethanolamine owing to the formation of intermediate diethanolamine by disproportionation of monoethanolamine. The experimental results also reveal that methylethanolamine and monoethanolamine are more difficult to form nitrosamines than diethanolamine. Therefore, it is reasonable and feasible to substitute fatty acid diethanolamide by monoethanolamide and methylethanolamide in surfactant production and application, which has theoretical and practical significance for safeguarding human health and safety.

Key words: fatty acid alkanolamides, surfactant, nitrosamine, ethanolamine compound, nitrosation mechanism

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.

References

[1]	ZHAN Li,ZHAN Lishi,WAN Li,et al. In vivo Micronuclei and Gene Mutation Induced by DEN in the lacZ Transgenic Mouse[J]. J Hygiene Res,2005,34(3):269-271(in Chinese). 詹立,张立实,王莉,等. 二乙基亚硝胺(DEN)诱发λ/lacZ转基因小鼠微核和基因突变实验研究[J]. 卫生研究,2005,34(3):269-271.
[2]	HUI Zhiyu,XU Yang,ZHU Jianhua,et al. Removal of N-Nitrosamine from Cigarette Smoke by Zeolite[J]. Chinese J Appl Chem,2002,19(3):276-279(in Chinese). 恽之瑜,徐杨,朱建华,等. 沸石在去除卷烟烟气中亚硝胺的应用[J]. 应用化学,2002,19(3):276-279.
[3]	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.
[4]	Sikora E,Sliwa K,Ogonowki J,et al. Study of Properties of Shampoos Containing Whey of Cow Milk[J]. SOFW J,2011,137(6):14-20.
[5]	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.
[6]	Wasilewski T.Coacervates as a Modern Delivery System of Hand Dishwashing Liquids[J]. J Surfactants Deterg,2010,13(4): 513-520.
[7]	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
[8]	Havery D C,Chou H J.Nitrosamines in Sunscreens and Cosmetic Products[C].ACS Symp Ser,1994.
[9]	Andersen F A.Amended Final Report on the Safety Assessment of Cocamide DEA[J]. J Am Coll Toxicol,1996,15(6): 527-542.
[10]	Fiume M M,Heldreth B,Bergfeld W F,et al. Safety Assessment of Diethanolamides as Used in Cosmetics[J]. Int J Toxicol,2013,32(3 Suppl):36S-58S.
[11]	HUANG Xiaodong,LI Yuhong,DAI Congjie,et al. 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(in Chinese) . 黄晓冬,李裕红,戴聪杰,等. 红树植物桐花树提取物清除亚硝酸盐与阻断亚硝胺合成的体外评价[J]. 中国食品学报,2015,15(9): 15-22.
[12]	LI ling,ZHANG Cuan,ZHOU Guanghong,et al. 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(in Chinese). 李玲,张汆,周光宏,等. 植物多酚对模拟胃酸体系中亚硝酸盐清除能力与亚硝胺生成的影响[J]. 南京农业大学学报,2013,36(3):111-116.
[13]	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.
[14]	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.
[15]	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.
[16]	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.
[17]	Lim D S,Roh T H,Kim M K,et al. Risk Assessment of N-Nitrosodiethylamine(NDEA) and N-Nitrosodiethanolamine(NDELA) in Cosmetics[J]. J Toxicol Environ Health,Part A,2018,81(12):465-480.
[18]	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.
[19]	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.
[20]	Chaudhary P,Gupta S,Muniyappan N,et al. 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.
[21]	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.
[22]	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.
[23]	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.
[24]	Zhang J,Jiang J,Li Y,et al. Iodide-Catalyzed Synthesis of N-Nitrosamines via C—N Cleavage of Nitromethane[J]. J Org Chem,2013,78(22):11366-11372.
[25]	Ridd J H.Nitrosation, Diazotisation, Deamination[J]. Q Rev Chem Soc,1961,15(4):418-441.
[26]	Da Silva E F,Lepaumier H,Grimstvedt A,et al.Understanding 2-Ethanolamine Degradation in Postcombustion CO2 Capture[J]. Ind Eng Chem Res,2012,51(41):13329-13338.
[27]	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.
[28]	Mirvish S S.Kinetics of Dimethylamine Nitrosation in Relation to Nitrosamine Carcinogenesis[J]. J Natl Cancer Inst,1970,44(3):633-639.

A Comparative Study on the Formation of Nitrosamines of Ethanolamines

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