Chem. J. Chinese Universities ›› 2017, Vol. 38 ›› Issue (12): 2198.doi: 10.7503/cjcu20170205
• Organic Chemistry • Previous Articles Next Articles
SUN Liwen1, ZHANG Yunxiao1,2, CAI Tao1,*(), SHANG Wangji1,2, LIU Dan1, TONG Dingyi1, LIU Shenggao1
Received:
2017-04-06
Online:
2017-12-10
Published:
2017-11-21
Contact:
CAI Tao
E-mail:caitao@nimte.ac.cn
Supported by:
CLC Number:
TrendMD:
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†[J]. Chem. J. Chinese Universities, 2017, 38(12): 2198.
Scheme 1 Synthesis routes of D-CnImBScB(n=4, 6, 8, 10) and CnImC8BScB(n=4, 6, 10)D-C4ImBScB: R1=R2=butyl; D-C6ImBScB: R1=R2=hexyl; D-C8ImBScB: R1=R2=octyl; D-C10ImBScB: R1=R2=decyl; C4ImC8BScB: R1=butyl, R2=octyl; C6ImC8BScB: R1=hexyl, R2=octyl; C10ImC8BScB: R1=decyl, R2=octyl.
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) |
Table 1 1H NMR data for D-CnImBScB(n=4, 6, 8, 10) and CnImC8BScB(n=4, 6, 10)
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) | |||||||
---|---|---|---|---|---|---|---|---|
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 |
Table 2 Kinematic viscosity of blends of ionic liquid(0.9 mmol/20 g PEG) with PEG
Temp./℃ | Kinematic viscosity/(mm2·s-1) | |||||||
---|---|---|---|---|---|---|---|---|
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 |
Fig.2 Coefficient of friction with contact time(A) and average wear scar diameter(B) of PEG200 and D-CnImBScB(n=4, 6, 8, 10) or CnImC8BScB(n=4, 6, 10) individually blended in PEG200a. PEG200; b. D-C4ImBScB; c. D-C6ImBScB; d. D-C8ImBScB; e. D-C10ImBScB; f. C4ImC8BScB; g. C6ImC8BScB; h. C10ImC8BScB.
Fig.3 Coefficient of friction with contact time(A) and average wear scar diameter(B) of PEG200 and C6ImC8BScB blended in PEG200 with 0.015, 0.03, 0.045, 0.06 mmol/g PEG200, respectively
Fig.5 Elements distribution of worn area lubricated with PEG200(A) and C6ImC8BScB blends with PEG200(B)(A1) Total worn area with PEG 200; (A2) carbon; (A3) oxygen; (B1) total worn area of C6ImC8BScB blends with PEG200;(B2) carbon; (B3) oxygen; (B4) nitrogen; (B5) boron.
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 |
Table 3 EDX element analysis of tribofilms formed by PEG200 and PEG200 with C6ImC8BScB
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 |
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