Modification of methyl oleate for silicon-based biological lubricating base oil

doi:10.1016/j.cjche.2016.06.001

›› 2017, Vol. 25 ›› Issue (1): 130-136.DOI: 10.1016/j.cjche.2016.06.001

• Energy, Resources and Environmental Technology • 上一篇下一篇

Modification of methyl oleate for silicon-based biological lubricating base oil

Shixing Cui, Zhi Yun, Xia Gui

College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing 210009, China

收稿日期:2016-04-26 修回日期:2016-06-02 出版日期:2017-01-28 发布日期:2017-02-15
通讯作者: Zhi Yun,E-mail address:yunzhi@njtech.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China (21306088), National Key Technologies R & D Program of China (2015BAD15B07), State Key Laboratory of Chemical Engineering (SKL-ChE-13A01, Tsinghua University, China) and Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD, China).

Modification of methyl oleate for silicon-based biological lubricating base oil

Shixing Cui, Zhi Yun, Xia Gui

College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing 210009, China

Received:2016-04-26 Revised:2016-06-02 Online:2017-01-28 Published:2017-02-15
Supported by:
Supported by the National Natural Science Foundation of China (21306088), National Key Technologies R & D Program of China (2015BAD15B07), State Key Laboratory of Chemical Engineering (SKL-ChE-13A01, Tsinghua University, China) and Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD, China).

摘要/Abstract

摘要： A new kind of silicon-based biological lubricating base oil with good viscosity-temperature behavior, viscosity index, thermostability, oxidation stability and wear resistance performance was synthesized as a derivative of methyl oleate. Trimethylsilylation reaction was introduced to further improve methyl oleate oxidation stability and lubricity after epoxidation and open-ring reactions. The order of effectiveness of acid binding agent was N,N-diisopropylethylamine (DIEA) > pyridine > diethylamine > triethylamine, and the effects of various parameters on the trimethylsilylation reaction as well as on the silicon-oxygen bond stability and reaction yield were studied. A maximum yield of 34.54% was achieved at hydroxyl/trimethyl chlorosilane/DIEA molar ratio of 1:1.25:1, reaction temperature 40℃, reaction time 1.5 h.

关键词: Methyl oleate, Trimethyl chlorosilane, Acid binding agent, N,N-diisopropylethylamine, Lubricity, Silicon-based biological lubricating base oil

Abstract: A new kind of silicon-based biological lubricating base oil with good viscosity-temperature behavior, viscosity index, thermostability, oxidation stability and wear resistance performance was synthesized as a derivative of methyl oleate. Trimethylsilylation reaction was introduced to further improve methyl oleate oxidation stability and lubricity after epoxidation and open-ring reactions. The order of effectiveness of acid binding agent was N,N-diisopropylethylamine (DIEA) > pyridine > diethylamine > triethylamine, and the effects of various parameters on the trimethylsilylation reaction as well as on the silicon-oxygen bond stability and reaction yield were studied. A maximum yield of 34.54% was achieved at hydroxyl/trimethyl chlorosilane/DIEA molar ratio of 1:1.25:1, reaction temperature 40℃, reaction time 1.5 h.

Key words: Methyl oleate, Trimethyl chlorosilane, Acid binding agent, N,N-diisopropylethylamine, Lubricity, Silicon-based biological lubricating base oil

Shixing Cui, Zhi Yun, Xia Gui. Modification of methyl oleate for silicon-based biological lubricating base oil[J]. , 2017, 25(1): 130-136.

参考文献

[1] A. Adhvaryu, Z. Liu, S.Z. Erhan, Synthesis of novel alkoxylated triacylglycerols and their lubricant base oil, Ind. Crop. Prod. 21(1) (2005) 113-119.
[2] S.L. Piyush, B. Mattiasson, Green approach for the preparation of biodegradable lubricant base stock from epoxidized vegetable oil, Appl. Catal. B Environ. 69(2007) 207-212.
[3] Z.E. Sevim, K.S. Brajendra, M.P. Joseph, Oxidation and low temperature stability of vegetable oil-based lubricants, Ind. Crop. Prod. 24(2006) 292-299.
[4] A. Campanella, M.A. Baltanas, Degradation of the oxirane ring of epoxidized vegetable oils in liquid-liquid heterogeneous reaction systems, Chem. Eng. J. 118(3) (2006) 141-152.
[5] H.S. Hwang, A. Adhvaryu, S.Z. Erhan, Preparation and properties of lubricant base stocks from epoxidized soybean oil and 2-ethylhexanol, J. Am. Oil Chem. Soc. 80(2003) 811-815.
[6] W.M. Li, X.B. Wang, Bio-lubricants derived from waste cooling oil with improved oxidation stability abd low-temperature properties, J. Oleo Sci. 64(4) (2015) 367-374.
[7] S. Jumat, S. Nadia, Y. Emad, Improvement of pour point and oxidative stability of synthetic ester basestocks for biolubricant applications, Arab. J. Chem. 5(2012) 193-200.
[8] H. Hong-Sik, Z.E. Sevim, Modification of epoxidized soybean oil for lubricant formulations with improved oxidative stability and low pour point, J. Am. Oil Chem. Soc. 78(12) (2001) 1179-1184.
[9] W.Q. Yang, Synthesis and tribological performance of phosphate ester containing nitrogen from methyl oleate in rapeseed oil, Asian Netw. Sci. Inf. (2015) 148-153.
[10] Chen, C. Y., "Method of preparing base oil of silicon-based biological lubricating oil from biodiesel oil method for preparing silicon-based biological lubricating oil base oil by using biodiesel", China Pat., 10054056(2014).
[11] L.G. Witucki, Organo-functional silanes, J. Coatings Technol. 65(822) (1993) 57-60.
[12] A.J. Kinloch, Adhesion and adhesives, Science and techology, Chapman and Hall, New York, 1987.
[13] Y.N. Na, "A kind of method for preparing biolubricant with borane as catalyst[machine translation]", Changzhou Kele Catalyst Co., Ltd., Peop. Rep, China, 2015.
[14] K.F. Ling, Formation of better catalytically active titanium species in Ti-MCM-41 by vapor-phase silylation, J. Catal. 235(2) (2005) 423-427.
[15] H.J. Jung, New silanization coating for DNA fragment analysis by capillary electroporesis, J. Polym. Sci. A 40(10) (2005) 1405-1420.
[16] W.P. Wang, Sythesis and characterization of organic silicon modified rapeseed oil, Chem. Bull. 77(3) (2014) 270-273.
[17] Chinese national GB standardization, standard no. 3142, 1982.
[18] Petrol-chemical industry SH standardization, standard no. 0731, 2004.
[19] Petrol-chemical industry SH standardization, standard no. 0193, 2008.
[20] Chinese national GB standardization, standard no. 265, 2008.
[21] Chinese national GB standardization, standard no. 261, 2008.
[22] Chinese national GB standardization, standard no. 3535, 2006.
[23] Petrol-chemical industry SH standardization, standard no. 0251, 1993.
[24] Chinese national GB standardization, standard no. 1668, 2008.
[25] Chinese national GB standardization, standard no. 12008, 1989.
[26] J.A. Marshall, R. Sedrani, Aconverget, Highly stereoselective synthesis of a C₁₁-C₁₂ submit of the macbecin, J. Org. Chem. 56(1991) 5496-5498.
[27] J.W. Gillard, R. Fortin, Symmetrical alkoxysilyl ethers, J. Org. Chem. 53(1988) 2602-2608.
[28] H. Enzhu, The role of soot particles in the tribological behavior of engine lubricating oils, Wear 5(2) (2013) 152-161.
[29] Q.G. Ren, Preparation of lubricant base stock through chemical modification of biodiesel, J. Fuel Chem. Technol. 43(01) (2015) 54-58.
[30] B.K. Sharma, A.J. Stipanovic, Development of a new oxidation stability test method for lubricating oils using high-pressure differential scanning calorimetry, Thermochim. Acta 402(2003) 1-18.
[31] B.K. Sharma, K.M. Doll, S.Z. Erhan, Ester hydroxy derivatives of methyl oleate:Tribological, oxidation and low temperature properties, Bioresour. Technol. 99(2008) 7333-7340.

Modification of methyl oleate for silicon-based biological lubricating base oil

Modification of methyl oleate for silicon-based biological lubricating base oil

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 0

编辑推荐

Metrics

本文评价