化工学报 ›› 2021, Vol. 72 ›› Issue (7): 3601-3612.DOI: 10.11949/0438-1157.20201874
收稿日期:
2020-12-20
修回日期:
2021-03-28
出版日期:
2021-07-05
发布日期:
2021-07-05
通讯作者:
詹国武,邱挺
作者简介:
蔡东仁(1990—),男,博士,讲师,基金资助:
CAI Dongren1(),ZHAN Guowu1(),XIAO Jingran1,QIU Ting2()
Received:
2020-12-20
Revised:
2021-03-28
Online:
2021-07-05
Published:
2021-07-05
Contact:
ZHAN Guowu,QIU Ting
摘要:
基于4-甲基噻唑,采用两步法合成4种不同阴离子的磺酸功能化离子液体用于催化无患子油与甲醇酯交换反应制备生物柴油。傅里叶红外光谱、核磁共振和热重分析结果表明,离子液体被成功制备并且具备高热稳定性。其中,3-(3-磺酸基)丙基-4-甲基噻唑三氟甲烷磺酸盐([Ps-MTH][CF3SO3])在所制备的离子液体中表现出最高的催化活性。以[Ps-MTH][CF3SO3]为催化剂,无患子油与甲醇酯交换反应的最佳操作条件为反应温度128℃、醇油摩尔比28.10∶1、催化剂用量0.62 mmol/g(基于油的质量)、反应时间8 h,生物柴油收率高达92.78%±0.47%。此外,[Ps-MTH][CF3SO3]具备良好的重复使用性,在不同酯交换反应中也表现出良好的催化活性。该研究为离子液体催化无患子油制备生物柴油的工业化生产提供了基础数据。
中图分类号:
蔡东仁, 詹国武, 肖静冉, 邱挺. 磺酸功能化离子液体的合成及催化制备生物柴油应用[J]. 化工学报, 2021, 72(7): 3601-3612.
CAI Dongren, ZHAN Guowu, XIAO Jingran, QIU Ting. Synthesis of sulfonic acid functionalized ionic liquids for catalytic applications in biodiesel production[J]. CIESC Journal, 2021, 72(7): 3601-3612.
离子液体 | δ |
---|---|
[Ps-MTH][HSO4] | 9.81 (d, J = 2.7 Hz, 1H), 7.74 (d, J = 1.6 Hz, 1H), 4.56~4.53 (m, 2H), 2.93 (d, J = 7.2 Hz, 2H), 2.51 (d, J = 1.0 Hz, 3H), 2.31~2.28 (m, 2H) |
[Ps-MTH][Tos] | 9.79 (d, J = 2.7 Hz, 1H), 7.73 (d, J = 0.9 Hz, 1H), 7.59 (d, J = 8.3 Hz, 2H), 7.27 (d, J = 7.9 Hz, 2H), 4.52 (d, J = 7.7 Hz, 2H), 2.92 (d, J = 7.2 Hz, 2H), 2.50 (d, J = 0.9 Hz, 3H), 2.30 (s, 3H), 2.29~2.26 (m, 2H) |
[Ps-MTH][CH3SO3] | 9.81 (d, J = 2.7 Hz, 1H), 7.75 (d, J = 1.0 Hz, 1H), 4.56~4.53 (m, 2H), 2.94 (t, J = 7.2 Hz, 2H), 2.71 (s, 3H), 2.51 (d, J = 1.0 Hz, 3H), 2.31~2.28 (m, 2H) |
[Ps-MTH][CF3SO3] | 9.81 (d, J = 2.7 Hz, 1H), 7.75 (d, J = 1.6 Hz, 1H), 4.56~4.54 (m, 2H), 2.94 (t, J = 7.2 Hz, 2H), 2.52 (d, J = 1.0 Hz, 3H), 2.32~2.29 (m, 2H) |
表1 4种磺酸功能化离子液体1H NMR数据
Table 1 The 1H NMR data of four sulfonic group functionalized ionic liquids
离子液体 | δ |
---|---|
[Ps-MTH][HSO4] | 9.81 (d, J = 2.7 Hz, 1H), 7.74 (d, J = 1.6 Hz, 1H), 4.56~4.53 (m, 2H), 2.93 (d, J = 7.2 Hz, 2H), 2.51 (d, J = 1.0 Hz, 3H), 2.31~2.28 (m, 2H) |
[Ps-MTH][Tos] | 9.79 (d, J = 2.7 Hz, 1H), 7.73 (d, J = 0.9 Hz, 1H), 7.59 (d, J = 8.3 Hz, 2H), 7.27 (d, J = 7.9 Hz, 2H), 4.52 (d, J = 7.7 Hz, 2H), 2.92 (d, J = 7.2 Hz, 2H), 2.50 (d, J = 0.9 Hz, 3H), 2.30 (s, 3H), 2.29~2.26 (m, 2H) |
[Ps-MTH][CH3SO3] | 9.81 (d, J = 2.7 Hz, 1H), 7.75 (d, J = 1.0 Hz, 1H), 4.56~4.53 (m, 2H), 2.94 (t, J = 7.2 Hz, 2H), 2.71 (s, 3H), 2.51 (d, J = 1.0 Hz, 3H), 2.31~2.28 (m, 2H) |
[Ps-MTH][CF3SO3] | 9.81 (d, J = 2.7 Hz, 1H), 7.75 (d, J = 1.6 Hz, 1H), 4.56~4.54 (m, 2H), 2.94 (t, J = 7.2 Hz, 2H), 2.52 (d, J = 1.0 Hz, 3H), 2.32~2.29 (m, 2H) |
离子液体 | δ |
---|---|
[Ps-MTH][HSO4] | 157.13, 146.27, 120.64, 50.73, 46.65, 24.01, 11.98 |
[Ps-MTH][Tos] | 157.09, 146.24, 141.98, 138.95, 128.95, 124.87, 120.64, 50.71, 46.64, 24.01, 19.99, 11.97 |
[Ps-MTH][CH3SO3] | 157.13, 146.28, 120.64, 50.73, 46.65, 37.96, 24.01, 11.98 |
[Ps-MTH][CF3SO3] | 157.12, 146.28, 120.64, 118.11, 50.73, 46.65, 24.01, 11.98 |
表2 4种磺酸功能化离子液体的13C NMR数据
Table 2 The 13C NMR data of four sulfonic group functionalized ionic liquids
离子液体 | δ |
---|---|
[Ps-MTH][HSO4] | 157.13, 146.27, 120.64, 50.73, 46.65, 24.01, 11.98 |
[Ps-MTH][Tos] | 157.09, 146.24, 141.98, 138.95, 128.95, 124.87, 120.64, 50.71, 46.64, 24.01, 19.99, 11.97 |
[Ps-MTH][CH3SO3] | 157.13, 146.28, 120.64, 50.73, 46.65, 37.96, 24.01, 11.98 |
[Ps-MTH][CF3SO3] | 157.12, 146.28, 120.64, 118.11, 50.73, 46.65, 24.01, 11.98 |
序号 | 离子液体 | 收率 / % |
---|---|---|
1 | [Ps-MIH][CF3SO3] | 83.85±0.39 |
2 | [Ps-MPH][CF3SO3] | 84.92±0.75 |
3 | [Ps-MTH][CF3SO3] | 87.28±0.83 |
4 | [Ps-MTH][HSO4] | 84.28±0.58 |
5 | [Ps-MTH][Tos] | 84.50±0.46 |
6 | [Ps-MTH][CH3SO3] | 81.62±0.29 |
表3 4种噻唑型离子液体的催化活性
Table 3 The catalytic activity of four sulfonic acid functionalized ionic liquids
序号 | 离子液体 | 收率 / % |
---|---|---|
1 | [Ps-MIH][CF3SO3] | 83.85±0.39 |
2 | [Ps-MPH][CF3SO3] | 84.92±0.75 |
3 | [Ps-MTH][CF3SO3] | 87.28±0.83 |
4 | [Ps-MTH][HSO4] | 84.28±0.58 |
5 | [Ps-MTH][Tos] | 84.50±0.46 |
6 | [Ps-MTH][CH3SO3] | 81.62±0.29 |
编码水平 | X1 反应温度/℃ | X2 醇油摩尔比 | X3 催化剂用量/(mmol/g) |
---|---|---|---|
-1 | 110 | 15 | 0.34 |
0 | 120 | 23 | 0.54 |
1 | 130 | 31 | 0.74 |
表4 响应面分析的因素及水平
Table 4 The factors and levels of response surface analysis
编码水平 | X1 反应温度/℃ | X2 醇油摩尔比 | X3 催化剂用量/(mmol/g) |
---|---|---|---|
-1 | 110 | 15 | 0.34 |
0 | 120 | 23 | 0.54 |
1 | 130 | 31 | 0.74 |
序号 | 工艺条件 | 收率 / % | |||
---|---|---|---|---|---|
X1 | X2 | X3 | 实验值 | 预测值 | |
1 | 0 | 0 | 0 | 87.80±0.36 | 87.23 |
2 | 0 | 0 | 0 | 87.67±0.47 | 87.23 |
3 | 1 | -1 | 0 | 77.03±0.33 | 77.12 |
4 | 1 | 1 | 0 | 89.45±0.58 | 88.95 |
5 | -1 | 0 | -1 | 69.02±0.61 | 68.45 |
6 | -1 | 1 | 0 | 79.16±0.55 | 79.07 |
7 | 0 | 0 | 0 | 87.02±0.52 | 87.23 |
8 | 1 | 0 | -1 | 79.02±0.19 | 78.86 |
9 | -1 | -1 | 0 | 64.32±0.83 | 64.82 |
10 | 1 | 0 | 1 | 84.60±0.36 | 85.17 |
11 | 0 | 0 | 0 | 87.05±0.49 | 87.23 |
12 | -1 | 0 | 1 | 73.24±0.35 | 73.40 |
13 | 0 | -1 | 1 | 65.26±0.68 | 64.60 |
14 | 0 | 1 | -1 | 71.35±0.25 | 72.01 |
15 | 0 | 0 | 0 | 86.63±0.73 | 87.23 |
16 | 0 | 1 | 1 | 87.82±0.28 | 87.76 |
17 | 0 | -1 | -1 | 69.04±0.44 | 69.10 |
表5 响应面分析的实验值和预测值
Table 5 The experimental values and predicted values of response surface analysis
序号 | 工艺条件 | 收率 / % | |||
---|---|---|---|---|---|
X1 | X2 | X3 | 实验值 | 预测值 | |
1 | 0 | 0 | 0 | 87.80±0.36 | 87.23 |
2 | 0 | 0 | 0 | 87.67±0.47 | 87.23 |
3 | 1 | -1 | 0 | 77.03±0.33 | 77.12 |
4 | 1 | 1 | 0 | 89.45±0.58 | 88.95 |
5 | -1 | 0 | -1 | 69.02±0.61 | 68.45 |
6 | -1 | 1 | 0 | 79.16±0.55 | 79.07 |
7 | 0 | 0 | 0 | 87.02±0.52 | 87.23 |
8 | 1 | 0 | -1 | 79.02±0.19 | 78.86 |
9 | -1 | -1 | 0 | 64.32±0.83 | 64.82 |
10 | 1 | 0 | 1 | 84.60±0.36 | 85.17 |
11 | 0 | 0 | 0 | 87.05±0.49 | 87.23 |
12 | -1 | 0 | 1 | 73.24±0.35 | 73.40 |
13 | 0 | -1 | 1 | 65.26±0.68 | 64.60 |
14 | 0 | 1 | -1 | 71.35±0.25 | 72.01 |
15 | 0 | 0 | 0 | 86.63±0.73 | 87.23 |
16 | 0 | 1 | 1 | 87.82±0.28 | 87.76 |
17 | 0 | -1 | -1 | 69.04±0.44 | 69.10 |
来源 | 方差和 | 自由度 | 均方 | F值 | P值 Prob > F |
---|---|---|---|---|---|
模型 | 1253.59 | 9 | 139.29 | 319.77 | < 0.0001 |
X1 | 245.98 | 1 | 245.98 | 564.69 | < 0.0001 |
X2 | 339.69 | 1 | 339.69 | 779.84 | < 0.0001 |
X3 | 63.23 | 1 | 63.23 | 145.15 | < 0.0001 |
X1X2 | 1.46 | 1 | 1.46 | 3.36 | 0.1094 |
X1X3 | 0.46 | 1 | 0.46 | 1.06 | 0.3371 |
X2X3 | 102.52 | 1 | 102.52 | 235.35 | < 0.0001 |
X12 | 46.43 | 1 | 46.43 | 106.59 | < 0.0001 |
X22 | 173.72 | 1 | 173.72 | 398.81 | < 0.0001 |
X32 | 233.27 | 1 | 233.27 | 535.53 | < 0.0001 |
残差 | 3.05 | 7 | 0.44 | ||
失拟项 | 2.09 | 3 | 0.70 | 2.92 | 0.1634 |
纯误差 | 0.95 | 4 | 0.24 | ||
离散系数 | R2 | 校正R2 | 预测R2 | 方差 | 精密度 |
0.66 | 0.9976 | 0.9945 | 0.9721 | 79.15 | 48.097 |
表6 BBD模型的方差及显著性
Table 6 The ANOVA and statistical criteria of BBD model
来源 | 方差和 | 自由度 | 均方 | F值 | P值 Prob > F |
---|---|---|---|---|---|
模型 | 1253.59 | 9 | 139.29 | 319.77 | < 0.0001 |
X1 | 245.98 | 1 | 245.98 | 564.69 | < 0.0001 |
X2 | 339.69 | 1 | 339.69 | 779.84 | < 0.0001 |
X3 | 63.23 | 1 | 63.23 | 145.15 | < 0.0001 |
X1X2 | 1.46 | 1 | 1.46 | 3.36 | 0.1094 |
X1X3 | 0.46 | 1 | 0.46 | 1.06 | 0.3371 |
X2X3 | 102.52 | 1 | 102.52 | 235.35 | < 0.0001 |
X12 | 46.43 | 1 | 46.43 | 106.59 | < 0.0001 |
X22 | 173.72 | 1 | 173.72 | 398.81 | < 0.0001 |
X32 | 233.27 | 1 | 233.27 | 535.53 | < 0.0001 |
残差 | 3.05 | 7 | 0.44 | ||
失拟项 | 2.09 | 3 | 0.70 | 2.92 | 0.1634 |
纯误差 | 0.95 | 4 | 0.24 | ||
离散系数 | R2 | 校正R2 | 预测R2 | 方差 | 精密度 |
0.66 | 0.9976 | 0.9945 | 0.9721 | 79.15 | 48.097 |
性质 | 数值 | ASTM D6751标准 |
---|---|---|
密度(20℃)/(kg/m3) | 869.43 | — |
运动黏度(40℃)/(mm2/s) | 6.34 | 1.9~6.0 |
酸值/(mg/g) | 0.37 | ≤0.50 |
含水量/(mg/kg) | 94 | ≤500 |
闪点/℃ | 170.5 | ≥130 |
铜片腐蚀度 | 1a | ≤3 |
十六烷值 | 60.9 | ≥47 |
表7 无患子生物柴油的理化性质
Table 7 The physicochemical properties of soapberry biodiesel
性质 | 数值 | ASTM D6751标准 |
---|---|---|
密度(20℃)/(kg/m3) | 869.43 | — |
运动黏度(40℃)/(mm2/s) | 6.34 | 1.9~6.0 |
酸值/(mg/g) | 0.37 | ≤0.50 |
含水量/(mg/kg) | 94 | ≤500 |
闪点/℃ | 170.5 | ≥130 |
铜片腐蚀度 | 1a | ≤3 |
十六烷值 | 60.9 | ≥47 |
序号 | 原料 | 低碳醇 | 催化剂 | 收率 / % |
---|---|---|---|---|
1 | 无患子油 | 甲醇 | — | 0 |
2 | 无患子油 | 甲醇 | H2SO4 | 91.26±0.34 |
3 | 无患子油 | 甲醇 | [Ps-MTH][CF3SO3] | 92.78±0.47 |
4 | 无患子油 | 乙醇 | [Ps-MTH][CF3SO3] | 83.17±0.28 |
5 | 无患子油 | 丙醇 | [Ps-MTH][CF3SO3] | 74.19±0.32 |
6 | 煎炸废油 | 甲醇 | [Ps-MTH][CF3SO3] | 76.77±0.61 |
7 | 棕榈油 | 甲醇 | [Ps-MTH][CF3SO3] | 84.59±0.54 |
8 | 椰子油 | 甲醇 | [Ps-MTH][CF3SO3] | 92.90±0.44 |
表8 [Ps-MTH][CF3SO3]在不同酯交换反应中的催化活性
Table 8 The catalytic activity of [Ps-MTH][CF3SO3] in different transesterifications
序号 | 原料 | 低碳醇 | 催化剂 | 收率 / % |
---|---|---|---|---|
1 | 无患子油 | 甲醇 | — | 0 |
2 | 无患子油 | 甲醇 | H2SO4 | 91.26±0.34 |
3 | 无患子油 | 甲醇 | [Ps-MTH][CF3SO3] | 92.78±0.47 |
4 | 无患子油 | 乙醇 | [Ps-MTH][CF3SO3] | 83.17±0.28 |
5 | 无患子油 | 丙醇 | [Ps-MTH][CF3SO3] | 74.19±0.32 |
6 | 煎炸废油 | 甲醇 | [Ps-MTH][CF3SO3] | 76.77±0.61 |
7 | 棕榈油 | 甲醇 | [Ps-MTH][CF3SO3] | 84.59±0.54 |
8 | 椰子油 | 甲醇 | [Ps-MTH][CF3SO3] | 92.90±0.44 |
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