咪唑螯合硼离子液体的合成、 表征及摩擦学性能

doi:10.7503/cjcu20160684

高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (4): 598.doi: 10.7503/cjcu20160684

咪唑螯合硼离子液体的合成、表征及摩擦学性能

张云潇^1,², 商旺吉^1,², 孙俪文¹, 刘丹¹, 童丁毅¹(), 蔡涛¹(), 刘升高¹

1. 中国科学院宁波材料技术与工程研究所, 宁波 315000
2. 上海大学材料科学与工程学院, 上海 200072

收稿日期:2016-09-26 出版日期:2017-04-10 发布日期:2017-03-23
作者简介:联系人简介: 蔡涛, 男, 博士, 助理研究员, 主要从事离子液体在润滑领域的研究. E-mail: caitao@nimte.ac.cn; 童丁毅, 男, 博士, 助理研究员, 主要从事离子液体在石油化工领域的研究. E-mail: tongdingyi@nimte.ac.cn
基金资助:
国家自然科学基金(批准号: 21404114)、中国博士后科学基金面上项目(批准号: 2014M561797)、浙江省博士后科研项目择优资助项目(批准号: BSH1502162)和宁波市自然科学基金(批准号: 2015A610051)资助

Synthesis, Characterization and Tribological Properties of Imidazol Cheat Boron Ionic Liquids with Different Alkyl Length^†

ZHANG Yunxiao^1,², SHANG Wangji^1,², SUN Liwen¹, LIU Dan¹, TONG Dingyi^1,^*(), CAI Tao^1,^*(), LIU Shenggao¹

1. Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315000, China
2. School of Materials Science and Engineering, Shanghai University, Shanghai 200072, China

Received:2016-09-26 Online:2017-04-10 Published:2017-03-23
Contact: TONG Dingyi,CAI Tao E-mail:tongdingyi@nimte.ac.cn;caitao@nimte.ac.cn
Supported by:
† Supported by the National Natural Science Foundation of China(No.21404114), the China Postdoctoral Science Foundation(No.2014M561797), the Zhejiang Postdoctoral Sustentation Fund, China(No BSH1502162) and the Natural Science Foundation of Ningbo, China(No.2015A610051)

摘要/Abstract

摘要：

以一类环境友好的螯合硼离子液体为研究对象, 合成了4种具有不同烷基直链阳离子中心的螯合硼离子液体C_nMImBScB(n=2,4,6,8); 通过核磁共振波谱(NMR)、电耦合等离子体发射光谱(ICP-OES)、热重分析(TGA)和差示扫描量热分析(DSC)等方法对4种螯合硼离子液体进行了结构分析、硼含量测定和热稳定性分析. 以聚乙二醇200(PEG200)作为基础油样品, C_nMImBScB(n=2,4,6,8)作为添加剂, 采用四球摩擦磨损试验机、扫描电子显微镜(SEM)和能量色散X射线光谱(EDX)分别对油样的减摩抗磨性能、磨斑形貌和磨斑表面元素分布进行了分析和表征. 结果表明, C_nMImBScB(n=2,4,6,8)可作为在较宽温度范围内使用的润滑油添加剂, 离子液体的低浓度(质量分数1%~2%)添加使PEG200的摩擦性能得到大幅度提高, 摩擦系数最大降低58.46%, 磨斑直径最大降低20.5%; 硼元素沉积到表面参与润滑膜的成膜, 磨斑表面碳元素含量的增加也有助于摩擦性能的提高.

关键词: 环境友好型, 硼, 离子液体, 抗磨损, 减摩

Abstract:

Four environmental-friendly ionic liquids containing imidazol cations with different alkyl chain lengths and bis(salicylato)borate anion were synthesized. Their structures were characterized by NMR, ICP-OES and tribo-performance was studied on four-ball machine and SEM-EDX as well. Tribological properties are largely influenced by alkyl chain lengths. C_nMImBScB(n=2,4,6,8) have excellent friction reducing properties, in particular, the coefficient of friction and wear scar diameter lubricated by PEG200 under 392N reduce 58.46% and 20.5%, respectively, when mass fraction of 2% C₈MImBScB is introduced. The elemental mapping of worn surfaces reveal that the formation of cheat boron ionic liquids constitutes a tribo-chemical thin film, which not only protect the contact surface against the wear at some extent but also reduces the friction significantly.

Key words: Environmental-friendly, Boron, Ionic liquid, Anti-wear, Anti-friction

中图分类号:

O621

TrendMD:

张云潇, 商旺吉, 孙俪文, 刘丹, 童丁毅, 蔡涛, 刘升高. 咪唑螯合硼离子液体的合成、表征及摩擦学性能. 高等学校化学学报, 2017, 38(4): 598.

ZHANG Yunxiao, SHANG Wangji, SUN Liwen, LIU Dan, TONG Dingyi, CAI Tao, LIU Shenggao. Synthesis, Characterization and Tribological Properties of Imidazol Cheat Boron Ionic Liquids with Different Alkyl Length^†. Chem. J. Chinese Universities, 2017, 38(4): 598.

图/表 12

参考文献 25

[1]	Minami I., Molecules, 2009, 6(14), 2286—2305
[2]	Duan H. F., Zhang S. B., Lin Y. J., Qiu Z. M., Wang Z. M., Chem. J. Chinese Universities, 2003, 24(11), 2024—2026
	(段海峰, 张所波, 林英杰, 邱志明, 王宗睦. 高等学校化学学报, 2003,24(11), 2024—2026)
[3]	Zhao Y., Cui H., Zheng C., Chen X., Li C., Chem. Res. Chinese Universities, 2016, 32(1), 112—117
[4]	Maria P., Virgil C., Chem. Res. Chinese Universities, 2014, 30(1), 119—124
[5]	Lei P., Luo H., Shi M. K., Zhang X., Chem. J. Chinese Universities, 2016, 37(9), 1722—1727
	(雷蓓, 罗辉, 石孟可, 张熙. 高等学校化学学报, 2016,37(9), 1722—1727)
[6]	Ye C.F., Liu W. M., Chen Y. X., Yu L. G.,Chem. Commun., 2001, (21), 2244—2245
[7]	Gong Q. Y., Yu L. G., Ye C. F., Wear,2002, 253(5/6), 558—562
[8]	Zhou F., Liang Y., Liu W., Chem. Soc. Rev., 2009, 38(9), 2590—2599
[9]	Mahrova M., Pagano F., Pejakovic V., Valea A., Kalin M., Igartua A., Tojo E., Tribol. Int., 2015, 82, 245—254
[10]	Anderson J. L., Ding R. F., Ellern A., Armstrong D. W., J. Am. Chem. Soc., 2005, 127(2), 593—604
[11]	Pu J. B., Wan S. H., Zhao W. J., Mo Y. F., Zhang X. Q., Wang L. P., Xue Q. J., J. Phys. Chem. C, 2011, 115(27), 13275—13284
[12]	Jimenez A. E., Bermudez M. D., Lglesias P., Carrion F. J., Nicolas G., Wear,2006, 260(7/8), 766—782
[13]	Sharma V., Doerr N., Erdemir A., Aswath P. B., RSC Adv., 2016, 5(58), 53148—53161
[14]	Shah F. U., Glavatskih S., Antzutkin O. N., Tribol. Lett., 2013, 51(3), 281—301
[15]	Dilasari B., Jung Y., Sohn J., Kim S., Kwon K., Int. J. Electrochem. Sci., 2016, 11(2), 1482—1495
[16]	Fukumoto K., Yoshizawa M., Ohno H., J. Am. Chem. Soc., 2005, 127(8), 2398—2399
[17]	Gusain R., Dhingra S., Khatri O. P., Ind. & Eng. Chem. Res., 2016, 55(4), 856—865
[18]	Gusain R., Khatri O. P., RSC Adv., 2016, 6(5), 3462—3469
[19]	Gusain R., KhatriO. P. , RSC Adv., 2015, 5(32), 25287—25294
[20]	Gusain R., Gupta P., Saran S., Khatri O. P., ACS Appl. Mater. Interfaces, 2014, 6(17), 15318—15328
[21]	Khatri P. K., Joshi C., Thakre G. D., Jain S. L., New J. Chem., 2016, 40(6), 5294—5299
[22]	Shah F. U., Glavatskih S., MacFarlane D. R., Somers A., Forsyth M., Antzutkin O. N., Phys. Chem. Chem. Phys., 2011, 13(28), 12865—12873
[23]	Pejakovic V., Tomastik C., Dorr N., Kalin M., Tribol. Int., 2016, 97, 234—243
[24]	Bonhote P., Papageorgiou N., Kalyanasundaram K., Gratzel M., Inorg. Chem., 1996, 37(1), 1168—1178
[25]	Zhang Y. W., Zeng X. Q., Wu H., Li Z. P., Ren T. H., Zhao Y. D., Tribol. Lett., 2014, 53(3), 533—542

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(400 MHz, CDCl₃), δ
C₂MImBScB	9.09(s, 1H, Imi—CH), 7.82(dd, J=7.9, 1.5 Hz, 2H, Imi—CH—CH—), 7.41—7.33(m, 2H, C₆H₄), 7.09(dd, J=11.7, 5.5 Hz, 2H, C₆H₄), 6.89—6.91(m, 4H, C₆H₄), 4.01(q, J=7.4 Hz, 2H, CH₂), 3.70(s, 3H, CH₃), 1.32(t, 3H, J=7.4 Hz, 3H, CH₃)	165.66, 159.17, 135.12, 129.58, 123.48, 121.71, 119.30, 118.30, 115.03, 44.94, 35.89, 14.92
C₄MImBScB	9.19(s, 1H, Imi—CH), 7.85(dd, J=7.8, 1.5 Hz, 2H, Imi—CH—CH—), 7.43—7.36(m, 2H, C₆H₄), 7.10(d, J=13.5 Hz, 2H, C₆H₄), 6.93—6.83(m, 4H, C₆H₄), 4.02(t, J=7.4 Hz, 2H, CH₂), 3.79(s, 3H, CH₃), 1.73—1.63(m, 2H, CH₂), 1.21(dq, J=14.7, 7.4 Hz, 2H, CH₂), 0.84(t, J=7.4 Hz, 3H, CH₃)	165.59, 159.18, 135.10, 129.59, 123.51, 122.06, 119.22, 118.27, 115.03, 49.56, 35.99, 31.61, 19.42, 13.20
C₆MImBScB	9.06(s, 1H, Imi—CH), 7.85(d, J=7.8 Hz, 2H, Imi—CH—CH—), 7.39—7.31(m, 2H, C₆H₄), 7.11(d, J=11.1 Hz, 2H, C₆H₄), 6.84(t, J=7.5 Hz, 4H, C₆H₄), 3.94(t, J=7.5 Hz, 2H, CH₂), 3.69(s, 3H, CH₃), 1.77—1.51(m, 2H, CH₂), 1.16(dd, J=14.2, 7.6 Hz, 6H, CH₂CH₂CH₂), 0.78(t, J=6.7 Hz, 3H, CH₃)	165.62, 158.18, 135.05, 129.59, 123.50, 122.05, 119.19, 118.26, 115.07, 49.82, 35.98, 30.86, 29.72, 25.66, 22.21, 13.84
C₈MImBScB	9.14 , (s, 1H, Imi—CH), 7.85(dd, J=9.8, 3.3 Hz, 2H, Imi—CH—CH—), 7.42—7.35(m, 2H, C₆H₄), 7.11(d, J=14.6 Hz, 2H, C₆H₄), 6.87(t, J=7.5 Hz, 4H, C₆H₄), 3.99(t, J=7.5 Hz, 2H, CH₂), 3.75(s, 3H, CH₃), 1.69(dd, J=13.8, 7.0 Hz, 2H, CH₂), 1.37—1.04(m, 10H, CH₂CH₂CH₂CH₂CH₂), 0.86(q, J=7.0 Hz, 3H, CH₃)	165.65, 159.16, 135.07, 129.58, 123.50, 122.05, 119.17, 118.26, 115.05, 48.81, 35.94, 31.56, 29.77, 28.55, 28.73, 26.00, 22.48, 14.02

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(400 MHz, CDCl₃), δ
C₂MImBScB	9.09(s, 1H, Imi—CH), 7.82(dd, J=7.9, 1.5 Hz, 2H, Imi—CH—CH—), 7.41—7.33(m, 2H, C₆H₄), 7.09(dd, J=11.7, 5.5 Hz, 2H, C₆H₄), 6.89—6.91(m, 4H, C₆H₄), 4.01(q, J=7.4 Hz, 2H, CH₂), 3.70(s, 3H, CH₃), 1.32(t, 3H, J=7.4 Hz, 3H, CH₃)	165.66, 159.17, 135.12, 129.58, 123.48, 121.71, 119.30, 118.30, 115.03, 44.94, 35.89, 14.92
C₄MImBScB	9.19(s, 1H, Imi—CH), 7.85(dd, J=7.8, 1.5 Hz, 2H, Imi—CH—CH—), 7.43—7.36(m, 2H, C₆H₄), 7.10(d, J=13.5 Hz, 2H, C₆H₄), 6.93—6.83(m, 4H, C₆H₄), 4.02(t, J=7.4 Hz, 2H, CH₂), 3.79(s, 3H, CH₃), 1.73—1.63(m, 2H, CH₂), 1.21(dq, J=14.7, 7.4 Hz, 2H, CH₂), 0.84(t, J=7.4 Hz, 3H, CH₃)	165.59, 159.18, 135.10, 129.59, 123.51, 122.06, 119.22, 118.27, 115.03, 49.56, 35.99, 31.61, 19.42, 13.20
C₆MImBScB	9.06(s, 1H, Imi—CH), 7.85(d, J=7.8 Hz, 2H, Imi—CH—CH—), 7.39—7.31(m, 2H, C₆H₄), 7.11(d, J=11.1 Hz, 2H, C₆H₄), 6.84(t, J=7.5 Hz, 4H, C₆H₄), 3.94(t, J=7.5 Hz, 2H, CH₂), 3.69(s, 3H, CH₃), 1.77—1.51(m, 2H, CH₂), 1.16(dd, J=14.2, 7.6 Hz, 6H, CH₂CH₂CH₂), 0.78(t, J=6.7 Hz, 3H, CH₃)	165.62, 158.18, 135.05, 129.59, 123.50, 122.05, 119.19, 118.26, 115.07, 49.82, 35.98, 30.86, 29.72, 25.66, 22.21, 13.84
C₈MImBScB	9.14 , (s, 1H, Imi—CH), 7.85(dd, J=9.8, 3.3 Hz, 2H, Imi—CH—CH—), 7.42—7.35(m, 2H, C₆H₄), 7.11(d, J=14.6 Hz, 2H, C₆H₄), 6.87(t, J=7.5 Hz, 4H, C₆H₄), 3.99(t, J=7.5 Hz, 2H, CH₂), 3.75(s, 3H, CH₃), 1.69(dd, J=13.8, 7.0 Hz, 2H, CH₂), 1.37—1.04(m, 10H, CH₂CH₂CH₂CH₂CH₂), 0.86(q, J=7.0 Hz, 3H, CH₃)	165.65, 159.16, 135.07, 129.58, 123.50, 122.05, 119.17, 118.26, 115.05, 48.81, 35.94, 31.56, 29.77, 28.55, 28.73, 26.00, 22.48, 14.02

Compd.	Measured mass fraction(%)	Nominal mass fraction(%)	Error(%)
C₂MImBScB	2.708	2.77	2.23
C₄MImBScB	2.550	2.61	2.30
C₆MImBScB	2.620	2.67	1.90
C₈MImBScB	2.270	2.34	2.99

Compd.	Measured mass fraction(%)	Nominal mass fraction(%)	Error(%)
C₂MImBScB	2.708	2.77	2.23
C₄MImBScB	2.550	2.61	2.30
C₆MImBScB	2.620	2.67	1.90
C₈MImBScB	2.270	2.34	2.99

Temperature/℃	Kinematic viscosity/(mm²·s^-1)
	Base oil	Lubricant blend
	PEG200	C₂MImBscB	C₄MImBscB	C₆MImBscB	C₈MImBscB
40	22.99	23.97	23.80	23.12	23.62
100	4.20	4.07	4.16	4.13	4.26

咪唑螯合硼离子液体的合成、表征及摩擦学性能

Synthesis, Characterization and Tribological Properties of Imidazol Cheat Boron Ionic Liquids with Different Alkyl Length^†

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Oil sample	Element	Mass fraction(%)	Atomic(%)	Oil sample	Element	Mass fraction(%)	Atomic(%)
PEG200	C	6.66	22.82	PEG200+2%C₈MImBScB	O	2.28	4.76
	O	4.41	11.35		Si	0.26	0.30
	Si	0.28	0.41		Cr	1.28	0.82
	Cr	1.56	1.23		Fe	79.64	47.63
	Fe	87.09	64.18		B	3.94	12.17
PEG200+2%C₈MImBScB	C	12.27	34.11		N	0.34	0.21

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咪唑螯合硼离子液体的合成、 表征及摩擦学性能

Synthesis, Characterization and Tribological Properties of Imidazol Cheat Boron Ionic Liquids with Different Alkyl Length†

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咪唑螯合硼离子液体的合成、表征及摩擦学性能

Synthesis, Characterization and Tribological Properties of Imidazol Cheat Boron Ionic Liquids with Different Alkyl Length^†