烷基咪唑螯合硼离子液体的合成及摩擦学性能

doi:10.7503/cjcu20170205

高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (12): 2198.doi: 10.7503/cjcu20170205

烷基咪唑螯合硼离子液体的合成及摩擦学性能

孙俪文¹, 张云潇^1,², 蔡涛¹(), 商旺吉^1,², 刘丹¹, 童丁毅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 315201
2. 上海大学材料科学与工程学院, 上海 200072

收稿日期:2017-04-06 出版日期:2017-12-10 发布日期:2017-11-21
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
基金资助:
国家自然科学基金(批准号: 21404114, 21507139)、中国博士后科学基金(批准号: 2014M561797)、浙江省博士后科研项目(批准号: BSH1502162)和宁波市自然科学基金(批准号: 2015A610051, 2016A610265)资助

Imidazolium-bis(salicylato)borate Ionic Liquids as Lubricant Additives: the Effect of Alkyl Chain Lengths on the Tribological Performance^†

SUN Liwen¹, ZHANG Yunxiao^1,², CAI Tao^1,^*(), SHANG Wangji^1,², LIU Dan¹, TONG Dingyi¹, LIU Shenggao¹

1. Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China
2. School of Materials Science and Engineering, Shanghai University, Shanghai 200072, China

Received:2017-04-06 Online:2017-12-10 Published:2017-11-21
Contact: CAI Tao E-mail:caitao@nimte.ac.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21404114, 21507139), the China Postdoctoral Science Foundation(No.2014M561797), the Zhejiang Postdoctoral Sustentation Fund, China(No;BSH1502162) and the Natural Science Foundation of Ningbo, China(Nos.2015A610051, 2016A610265)

摘要/Abstract

摘要：

以1种环境友好的双水杨酸螯合硼为阴离子中心, 以咪唑环为阳离子骨架, 合成了7种新的具有不同烷基直链的螯合硼离子液体D-C_nImBScB(n=4, 6, 8, 10)和C_nImC₈BScB(n=4, 6, 10). 利用核磁共振波谱(¹H NMR)、热重分析(TGA)和差示扫描热量(DSC)等技术对7种双咪唑螯合硼离子液体进行了结构和热稳定性分析. 以聚乙二醇(PEG200)作为基础油, 双边咪唑螯合硼离子液体D-C_nImBScB(n=4, 6, 8, 10)和C_nImC₈BScB(n=4, 6, 10)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射线光谱仪(EDX)分别对油样的抗磨减摩性能、磨斑形貌和磨斑表面元素分布进行了分析表征. 结果表明, D-C_nImBScB(n=4, 6, 8, 10)和C_nImC₈BScB(n=4, 6, 10)可用作在较宽温度范围使用的润滑油添加剂, 添加C₆ImC₈BScB的PEG200油样抗磨效果最佳, 其磨斑直径为0.712 mm, 与PEG200相比降低了27.49%, 通过适当调节阳离子咪唑环骨架上的双边烷基链长度可以调控离子液体的摩擦学性能.

关键词: 离子液体, 环境友好型, 螯合硼, 碳链长度, 抗磨损

Abstract:

Seven environmental-friendly ionic liquids containing chelated organoborate anions having different alkyl chain lengths were synthesized and then evaluated as potential lubricant additives. The ¹H NMR, TGA and DSC were employed to characterized the structure and thermal properties of synthesized ionic liquids. The tribo-performacne were systematically studied by four-ball machine and SEM-EDX as well. The synthesized ionic liquids were found to be quite stable at room temperature and showed remarkable improvement in the anti-wear properties of the poly(ethylene) glycol(PEG200) lube base. The results showed that ionic liquids as additives significantly reduced the wear of PEG200, and particularly the variation in substituted alkyl chain length on the imidazolium ring monitored the degree of reduction in wear. C₆ImC₈BScB shows the excellent friction reducing properties among all the synthesized ionic liquids, the coefficient of wear scar diameter lubricated by PEG under 392 N corresponding reduced with mass fraction of 27.49%.

Key words: Ionic liquid, Environmental-friendly, Bis(salicylato)borate anion, Alkyl chain length, Anti-wear

中图分类号:

O621

TrendMD:

孙俪文, 张云潇, 蔡涛, 商旺吉, 刘丹, 童丁毅, 刘升高. 烷基咪唑螯合硼离子液体的合成及摩擦学性能. 高等学校化学学报, 2017, 38(12): 2198.

SUN Liwen, ZHANG Yunxiao, CAI Tao, SHANG Wangji, LIU Dan, TONG Dingyi, LIU Shenggao. Imidazolium-bis(salicylato)borate Ionic Liquids as Lubricant Additives: the Effect of Alkyl Chain Lengths on the Tribological Performance^†. Chem. J. Chinese Universities, 2017, 38(12): 2198.

图/表 9

参考文献 32

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Compd.	¹H NMR(400 MHz, CDCl₃), δ
D-C₄ImBScB	0.831(t, J=4.0 Hz, 6H, CH₃), 1.159—1.252(m, 4H, CH₂), 1.654—1. 729(m, 4H, CH₂), 4.052(t, J=7.4 Hz, 4H, CH₂), 6.874(dd, J=8.4, 13.2 Hz, 4H, C₆H₄), 7.129(s, 2H, C₆H₄), 7.387(t, J=7.6 Hz, 2H, C₆H₄), 7.858(d, J=7.6, 8.0 Hz, 2H, Imi—CH—CH—), 9.274(s, 1H, Imi—CH)
D-C₆ImBScB	0.813(t, J=6.8 Hz, 6H, CH₃), 1.185[s, 12H, (CH₂)₃], 1.717(t, J=6.4 Hz, 4H, CH₂), 4.056(t, J=7.6 Hz, 4H, CH₂), 6.846—6.898(m, 4H, C₆H₄), 7.015(d, J=2.4 Hz, 2H, C₆H₄), 7.360—7.408(m, 2H, C₆H₄), 7.865(d, J=1.2 Hz, 2H, Imi—CH—CH—), 9.307(s, 1H, Imi—CH)
D-C₈ImBScB	0.855(t, J=6.8 Hz, 6H, CH₃), 1.194—1.271[m, 20H, (CH₂)₅], 1.739(t, J=5.6 Hz, 4H, CH₂), 4.087(t, J=7.6 Hz, 4H, CH₂), 6.845—6.922(m, 4H, C₆H₄), 7.082(d, J=1.6 Hz, 2H, C₆H₄), 7.367—7.410(m, 2H, C₆H₄), 7.859(dd, J=1.6, 8.0 Hz, 2H, Imi—CH—CH—), 9.363(s, 1H, Imi—CH)
D-C₁₀ImBScB	0.871(t, J=6.8 Hz, 6H, CH₃), 1.186—1.298[m, 28H, (CH₂)₇], 1.713—1.763(m, 4H, CH₂), 4.075(t, J=7.2 Hz, 4H, CH₂), 6.837—6.901(m, 4H, C₆H₄), 7.103(d, J=1.6 Hz, 2H, C₆H₄), 7.353—7.396(m, 2H, C₆H₄), 7.850(dd, J=1.6, 7.8 Hz, 2H, Imi—CH—CH—), 9.394(s, 1H, Imi—CH)
C₄ImC₈BScB	0.834(q, J=7.4 Hz, 6H, CH₃), 1.165—1.256[m, 12H, (CH₂)₅ and CH₂], 1.665(dt, J=7.6, 15.4 Hz, 4H, CH₂), 4.039(t, J=7.2 Hz, 4H, CH₂), 6.865(t, J=8.0 Hz, 4H, C₆H₄), 7.144(s, 2H, C₆H₄), 7.379(t, J=7.8 Hz, 2H, C₆H₄), 7.857(d, J=7.6 Hz, 2H, Imi—CH—CH—), 9.260(s, 1H, Imi—CH)
C₆ImC₈BScB	0.789—0.863(m, 6H, CH₃), 1.165—1.242[m, 16H, (CH₂)₅ and (CH₂)₃], 1.684—1.736(m, 4H, CH₂), 4.037(t, J=7.4 Hz, 4H, CH₂), 6.864(t, J=8.6 Hz, 4H, C₆H₄), 7.139(s, 2H, C₆H₄), 7.357—7.399(m, 2H, C₆H₄), 7.855(dd, J=2.8, 9.4 Hz, 2H, Imi—CH—CH—), 9.257(s, 1H, Imi—CH)
C₁₀ImC₈BScB	0.862(q, J=7.2 Hz, 6H, CH₃), 1.186—1.279[m, 24H, (CH₂)₅ and (CH₂)₇], 1.713—1.763(m, 4H, CH₂), 4.073(t, J=7.4 Hz, 4H, CH₂), 6.844—6.913(m, 4H, C₆H₄), 7.092(s, 2H, C₆H₄), 7.384(t, J=7.8 Hz, 2H, C₆H₄), 7.857(d, J=7.6 Hz, 2H, Imi—CH—CH—), 9.331(s, 1H, Imi—CH)

Compd.	¹H NMR(400 MHz, CDCl₃), δ
D-C₄ImBScB	0.831(t, J=4.0 Hz, 6H, CH₃), 1.159—1.252(m, 4H, CH₂), 1.654—1. 729(m, 4H, CH₂), 4.052(t, J=7.4 Hz, 4H, CH₂), 6.874(dd, J=8.4, 13.2 Hz, 4H, C₆H₄), 7.129(s, 2H, C₆H₄), 7.387(t, J=7.6 Hz, 2H, C₆H₄), 7.858(d, J=7.6, 8.0 Hz, 2H, Imi—CH—CH—), 9.274(s, 1H, Imi—CH)
D-C₆ImBScB	0.813(t, J=6.8 Hz, 6H, CH₃), 1.185[s, 12H, (CH₂)₃], 1.717(t, J=6.4 Hz, 4H, CH₂), 4.056(t, J=7.6 Hz, 4H, CH₂), 6.846—6.898(m, 4H, C₆H₄), 7.015(d, J=2.4 Hz, 2H, C₆H₄), 7.360—7.408(m, 2H, C₆H₄), 7.865(d, J=1.2 Hz, 2H, Imi—CH—CH—), 9.307(s, 1H, Imi—CH)
D-C₈ImBScB	0.855(t, J=6.8 Hz, 6H, CH₃), 1.194—1.271[m, 20H, (CH₂)₅], 1.739(t, J=5.6 Hz, 4H, CH₂), 4.087(t, J=7.6 Hz, 4H, CH₂), 6.845—6.922(m, 4H, C₆H₄), 7.082(d, J=1.6 Hz, 2H, C₆H₄), 7.367—7.410(m, 2H, C₆H₄), 7.859(dd, J=1.6, 8.0 Hz, 2H, Imi—CH—CH—), 9.363(s, 1H, Imi—CH)
D-C₁₀ImBScB	0.871(t, J=6.8 Hz, 6H, CH₃), 1.186—1.298[m, 28H, (CH₂)₇], 1.713—1.763(m, 4H, CH₂), 4.075(t, J=7.2 Hz, 4H, CH₂), 6.837—6.901(m, 4H, C₆H₄), 7.103(d, J=1.6 Hz, 2H, C₆H₄), 7.353—7.396(m, 2H, C₆H₄), 7.850(dd, J=1.6, 7.8 Hz, 2H, Imi—CH—CH—), 9.394(s, 1H, Imi—CH)
C₄ImC₈BScB	0.834(q, J=7.4 Hz, 6H, CH₃), 1.165—1.256[m, 12H, (CH₂)₅ and CH₂], 1.665(dt, J=7.6, 15.4 Hz, 4H, CH₂), 4.039(t, J=7.2 Hz, 4H, CH₂), 6.865(t, J=8.0 Hz, 4H, C₆H₄), 7.144(s, 2H, C₆H₄), 7.379(t, J=7.8 Hz, 2H, C₆H₄), 7.857(d, J=7.6 Hz, 2H, Imi—CH—CH—), 9.260(s, 1H, Imi—CH)
C₆ImC₈BScB	0.789—0.863(m, 6H, CH₃), 1.165—1.242[m, 16H, (CH₂)₅ and (CH₂)₃], 1.684—1.736(m, 4H, CH₂), 4.037(t, J=7.4 Hz, 4H, CH₂), 6.864(t, J=8.6 Hz, 4H, C₆H₄), 7.139(s, 2H, C₆H₄), 7.357—7.399(m, 2H, C₆H₄), 7.855(dd, J=2.8, 9.4 Hz, 2H, Imi—CH—CH—), 9.257(s, 1H, Imi—CH)
C₁₀ImC₈BScB	0.862(q, J=7.2 Hz, 6H, CH₃), 1.186—1.279[m, 24H, (CH₂)₅ and (CH₂)₇], 1.713—1.763(m, 4H, CH₂), 4.073(t, J=7.4 Hz, 4H, CH₂), 6.844—6.913(m, 4H, C₆H₄), 7.092(s, 2H, C₆H₄), 7.384(t, J=7.8 Hz, 2H, C₆H₄), 7.857(d, J=7.6 Hz, 2H, Imi—CH—CH—), 9.331(s, 1H, Imi—CH)

Temp./℃	Kinematic viscosity/(mm²·s^-1)
Temp./℃	PEG200	D-C₄ImBScB	D-C₆ImBScB	D-C₈ImBScB	D-C₁₀ImBScB	C₄ImC₈BScB	C₆ImC₈BScB	C₁₀ImC₈BScB
40	22.99	24.09	24.41	24.05	23.83	24.56	24.24	24.28
100	4.20	4.18	4.22	4.19	4.21	4.16	4.21	4.26

Temp./℃	Kinematic viscosity/(mm²·s^-1)
Temp./℃	PEG200	D-C₄ImBScB	D-C₆ImBScB	D-C₈ImBScB	D-C₁₀ImBScB	C₄ImC₈BScB	C₆ImC₈BScB	C₁₀ImC₈BScB
40	22.99	24.09	24.41	24.05	23.83	24.56	24.24	24.28
100	4.20	4.18	4.22	4.19	4.21	4.16	4.21	4.26

Oil sample	Element	Mass fraction(%)	Atomic fraction(%)
PEG200	C	6.81	23.81
	O	3.12	8.18
	Si	0.27	0.41
	Cr	1.72	1.39
	Fe	88.07	66.21
PEG200 and C₆ImC₈BScB	C	8.12	25.69
	O	2.87	6.81
	Si	0.23	0.31
	Cr	1.63	1.19
	Fe	84.63	57.57
	B	1.99	7.01
	N	0.53	1.43

烷基咪唑螯合硼离子液体的合成及摩擦学性能

Imidazolium-bis(salicylato)borate Ionic Liquids as Lubricant Additives: the Effect of Alkyl Chain Lengths on the Tribological Performance^†

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烷基咪唑螯合硼离子液体的合成及摩擦学性能

Imidazolium-bis(salicylato)borate Ionic Liquids as Lubricant Additives: the Effect of Alkyl Chain Lengths on the Tribological Performance†

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Imidazolium-bis(salicylato)borate Ionic Liquids as Lubricant Additives: the Effect of Alkyl Chain Lengths on the Tribological Performance^†