N-月桂酰基甲基丙氨酸钠的合成与性能研究

doi:10.3969/j.issn.1001-1803.2021.06.004

Abstract

Abstract:

Using methylalanine and lauroyl chloride as the main raw materials, an anionic amino acid surfactant, N-lauroyl methylalanine sodium salt （SLMA） , was synthesized under alkaline conditions. The structure of the product was characterized through FT-IR, MS and ¹H NMR. The Krafft point, critical micelle concentration （cmc） , surface tension, emulsification, wetting, foaming and detergency of SLMA were determined, as well as the conductivity, micropolarity and critical micelle aggregation number of SLMA at different temperatures. The results show that the Krafft point of SLMA is lower than 0 ℃. The cmc’s of SLMA are 8.23×10^-3, 8.27×10^-3, 8.29×10^-3and 8.34×10^-3 mol/L at 25, 35, 45 and 55 ℃, respectively, and the γ_cmc are 33.00, 32.90, 32.80 and 32.10 mN/m, respectively. The emulsification and wetting properties of SLMA are better than those of sodium N-lauroyl sarcosinate （LS） . The foaming, foam stabilization and detergency values of SLMA are equivalent to those of LS. The critical micelle aggregation number of SLMA are 11, 35, 60 and 79 at 25, 35, 45 and 55 ℃, respectively.

Key words: anionic amino acid surfactant, methylalanine, lauroyl chloride, surface activity

CLC Number:

TQ423

LI Ying,XU Hu-jun. Study on the synthesis and performance of sodium N-lauroyl methylalaninate[J].China Surfactant Detergent & Cosmetics, 2021, 51(6): 496-501.

Figures/Tables 11

Fig. 1

Fig. 2

Fig. 3

Fig. 4

Tab. 1

Tab. 2

Tab. 3

Fig. 5

Fig. 6

Tab. 4

Fig. 7

References 17

[1]	Xu Hujun, Fang Qing, Huang Yaru, et al. Synjournal, performance and application of N-fatty acyl amino acid salt[J]. China Cleaning Industry, 2016 (2): 61-65.
[2]	Ge Hong, Zhang Zhiqiang, Wang Jun, et al. Research progress of N-Acidyl amino acid surfactants[J]. China Surfactant Detergent & Cosmetics, 2006 (2): 94-98.
[3]	Mao Xuebin, Hong Yuqian, Xun Kunhua, et al. Application progress of amino acid-based surfactants[J]. China Cleaning Industry, 2018 (10): 44-47.
[4]	Liu Qing. Synthesis and performance test of amino acid surfactant derived from functionalized amino group[D]. Changsha:Hunan Normal University, 2015.
[5]	Imabayashi Yuko, Yoshikawa Seibei, Takahashi Katashi. Studies on the application of surfactants derived from amino acid. Part 1:On the detergency of cloths soiled with carbon black and fatty acid[J]. Sen’i Seihin Shohi Kagaku, 1986,27(5): 219.
[6]	Cheng Haitao, Li Junsheng, Wang Tao, et al. Synjournal of N-coconut oil acyl compound amino acid surfactant[J]. China Surfactant Detergent & Cosmetics, 2010,40(1): 14-17.
[7]	Fang Yinjun, Kong Lingniao, Zhou Dapeng, et al. Research and development of surfactants for daily chemicals[J]. China Cleaning Industry, 2013 (2): 41-48.
[8]	Yoshida R, Shishido T. Process for preparing N-higher aliphatic acyl derivatives of aminoacids, peptides or proteins:US3985722[P]. 1976-10-12.
[9]	Akiyama R, Sagae T, Sugiura M, et al. Efficient synjournal of N-acyl-α-amino acids via polymer incarcerated palladium-catalyzed amidocarbonylation[J]. Journal of Organometallic Chemistry, 2005,36(14): 412-423.
[10]	Beller M, Eckert D C M, Vollmüller D C F, et al. Palladium-catalyzed amidocarbonylation-a new, efficient synjournal of N-acyl amino acids[J]. Angewandte Chemie International Edition, 1997,36(36): 1494-1496.
[11]	Wang Jie, Bo Chunling, Wang Shuyu, et al. Development of amino acid surfactants[J]. China Cleaning Industry, 2018 (6): 61-68.
[12]	Hedley Thomas & Co., Ltd. Proeess for produetion acyl aminde of amino acid salts:GB903431[P]. 1962.
[13]	Jursic B S, Neumann D. Preparation of N-acyl derivatives of amino acids from acyl chlorides and amino acids in the presence of cationic surfactants. A variation of the Schotten-Baumann method of benzoylation of amino acids[J]. Synthetic Communications, 2001,31(4): 555-564. doi: 10.1081/SCC-100000582
[14]	Fredric M Menger, Jason S Keiper. Gemini surfactants[J]. Angewandte Chemie, 2000,39(11): 1906-1920.
[15]	Lu Dandan, Ye Zhiwen. Study on the synjournal of an N-acyl amino acid surfactant[J]. China Surfactant Detergent & Cosmetics, 2013,43(1): 34-37.
[16]	Qian Huichao. Research on process development and application performance of amino acid surfactants[D]. Shanghai:East China University of Science and Technology, 2012.
[17]	Wu Lili. Progress in the synjournal and performance of amino acid gemini surfactants[J]. China Surfactant Detergent & Cosmetics, 2015,45(6): 342-346.

表面活性剂	θ/℃	cmc/（mol·L^-1）	γ_cmc/（mN·m^-1）	Γ_max/（μmol·m^-1）	A_min/nm²	pc₂₀	cmc/c₂₀
SLMA	25	8.23×10^-3	33.00	1.83	0.91	2.99	8.04
	35	8.27×10^-3	32.90	1.69	0.98	3.02	8.66
	45	8.29×10^-3	32.80	1.61	1.03	3.04	9.09
	55	8.34×10^-3	32.10	1.52	1.09	3.07	9.80

产品	泡沫高度/cm		稳泡性
产品	0 min	5 min	V_{5 min}/V_{0 min}
SLMA	13.10	12.10	0.92
SLMA	13.00	12.05	0.93
LS	17.30	17.20	0.99
LS	17.31	17.16	0.99

污布种类	去污值R
污布种类	SLMA	LS
蛋白	4.44	4.87
皮脂	7.47	8.67
炭黑	14.05	15.43

θ/℃	cmc/（mol·L^-1）	β	ΔG_m/（kJ·mol^-1）	ΔH_m/（kJ·mol^-1）	ΔS_m/（kJ·mol^-1）	-TΔS_m/（kJ·mol^-1）
25	12.20×10^-3	0.49	-21.59	-1.61	0.07	-19.98
35	12.33×10^-3	0.46	-21.57	-1.66	0.07	-19.91
45	12.40×10^-3	0.42	-21.46	-1.71	0.06	-19.75
55	12.64×10^-3	0.46	-22.89	-1.89	0.06	-21.00

Study on the synthesis and performance of sodium N-lauroyl methylalaninate

RichHTML

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 11

References 17

Related Articles 15

Metrics

Comments

Recommended 10

[1]	Cui Congcong,Zhang Hongli,Xuan Guangshan. Study on preparation and performance of multi-headgroup quaternary ammonium surfactant [J]. China Surfactant Detergent & Cosmetics, 2023, 53(8): 899-907.
[2]	Xing Huanyu, Jia Lihua, Zhao Zhenlong, Yang Rui, Guo Xiangfeng. Synthesis and properties of novel surfactants containing naphthalimide and alkyl segments [J]. China Surfactant Detergent & Cosmetics, 2023, 53(7): 742-747.
[3]	Zheng Lanjian,Zang Ying,Lin Tong,Xie Yiwen,Wang Honglei. The production of high yield biosurfactant rhamnolipid and performance research [J]. China Surfactant Detergent & Cosmetics, 2022, 52(9): 937-944.
[4]	Wang Junxia,Liu Jianhua,Lu Xiaomeng,Sun Yongqiang,Hu Zhiyong,Zhu Hailin. Corrosion inhibition effect of a quaternary ammonium surfactant containing thiadiazole on Q235 steel [J]. China Surfactant Detergent & Cosmetics, 2022, 52(8): 797-804.
[5]	WANG Jun,ZHANG Chen-long,YANG Xu-zhao,BAI Ya-rong. Research progress of magnetic surfactants [J]. China Surfactant Detergent & Cosmetics, 2021, 51(6): 546-553.
[6]	ZHU Hai-lin,LI Xiao-fen,LU Xiao-meng,HUANG Hao-yu,WANG Zi-xiang,HU Zhi-yong. Study on the synthesis of a sulfonate surfactant and its corrosion inhibition performance for carbon steel [J]. China Surfactant Detergent & Cosmetics, 2021, 51(5): 375-382.
[7]	ZHONG Guo-yuan,ZHANG Li-ming,HU Dong-min,PENG Hua-nan,YANG Yan-chun,ZHENG Jie. Study on preparation and properties of thermal responsive poly （dimethylaminoethyl methacrylate） quaternary ammonium [J]. China Surfactant Detergent & Cosmetics, 2021, 51(5): 428-432.
[8]	DU Jing-jing,HAN Xiao-hui,WANG Bo,XU Jing,ZHANG Zhang. Research progress of chitosan-modified polymeric surfactants [J]. China Surfactant Detergent & Cosmetics, 2021, 51(1): 56-62.
[9]	LIU Jia-jia,XU Hu-jun. Study on the synthesis and properties of fatty amido propyl phosphobetaine [J]. China Surfactant Detergent & Cosmetics, 2020, 50(7): 446-451.
[10]	SHI Li-yan,YANG Ming-zhu,SONG Bing-lei,CUI Zheng-gang. Synthesis of a eugenol-based surfactant and its application in preparing nanospheres [J]. China Surfactant Detergent & Cosmetics, 2020, 50(6): 373-378.
[11]	YANG Shan,XU Yang,GAO Yun-long. Preparation and surface activity of random copolymer P（AA-co-BA） [J]. China Surfactant Detergent & Cosmetics, 2020, 50(6): 387-391.
[12]	ZHOU Yuan,YANG Xiu-quan,ZHANG Jun. Performance and phase behavior of the mixture of alkyl polyglycoside sulfosuccinate and alkyl polyglycoside [J]. China Surfactant Detergent & Cosmetics, 2020, 50(1): 20-25.
[13]	YANG Xu-zhao,WANG Jun,FANG Yun. Synthesis and surface activities of asymmetrical Gemini ionic liquid-based surfactants [J]. China Surfactant Detergent & Cosmetics, 2019, 49(5): 279-285.
[14]	WANG Chen,XU Hu-jun. Synthesis and properties of a series of Gemini surfactants with p-phenylenediamine as a spacer [J]. China Surfactant Detergent & Cosmetics, 2019, 49(5): 293-297.
[15]	ZHANG Wen-zhe,LI Pan,HOU Lin-xi. Preparation of Gemini surfactants containing rigid groups and their properties after mixed with sodium dodecyl sulfate [J]. China Surfactant Detergent & Cosmetics, 2019, 49(5): 298-303.