Chem. J. Chinese Universities ›› 2017, Vol. 38 ›› Issue (4): 598.doi: 10.7503/cjcu20160684
• Organic Chemistry • Previous Articles Next Articles
ZHANG Yunxiao1,2, SHANG Wangji1,2, SUN Liwen1, LIU Dan1, TONG Dingyi1,*(
), CAI Tao1,*(), LIU Shenggao1
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:CLC Number:
TrendMD:
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†[J]. Chem. J. Chinese Universities, 2017, 38(4): 598.
Fig.1 Structures and codes of CnMImBScB(n=2,4,6,8)
| 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 |
Table 1 1H NMR and 13C NMR data for CnMImBScB(n=2,4,6,8)
| 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 |
Table 2 Boron concentration of CnMImBScB(n=2,4,6,8)
| 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 |
Fig.2 DSC curves of CnMImBScB(n=2,4,6,8) at a heating rate of 10 ℃/min and argon flow rate of 20 mL/min
Fig.3 TG(A) and DTG(B) curves of CnMImBScB(n=2,4,6,8) at a heating rate of 10 ℃/min and argon flow rate of 20 mL/min
Fig.4 Viscosity of C6MimBScB as a function of temperature
| 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 |
Table 3 Kinematic viscosity of blends of ionic liquids(mass fraction 2%) with PEG200
| 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 |
Fig.5 Evolution of coefficient of friction(CoF) with contact time(A), average coefficient of friction(B) and average wear scar diameter(WSD) of PEG200 and CnMImBScB(n=2,4,6,8, mass fraction 2%) individually blended in PEG200(C)a. PEG200; b. PEG200+G2MImBScB; c. PEG200+C4MImBScB; d. PEG200+C6MImBScB; e. PEG200+C8MImBScB.
Fig.6 Evolution of friction coefficient(CoF) with contact time(A), average friction coefficient(B) and wear scar diameter(C) of PEG200, C8MImBScB blended in PEG200 with mass fraction of 0(a), 0.5%(b), 1%(c), 2%(d), 4%(e), respectively
Fig.7 Elemental distribution of worn area lubricated with mass fraction of 2% C2MImBScB(A1—A4), C4MImBScB(B1—B4), C6MImBScB(C1—C4) and C8MImBScB(D1—D4) ionic liquids blends with PEG200(A1—D1) SEM images; (A2—D2) element C; (A3—D3) element N; (A4—D4) element B.
Fig.8 Electron images of worn surface lubricated PEG200(A) and PEG200+2%C8MImBScB(B)
| 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 |
Table 4 EDX element analysis of tribofilms formed by PEG200 and PEG200 with 2% C8MImBScB
| 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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