Chemical Industry and Engineering Progress ›› 2023, Vol. 42 ›› Issue (1): 272-281.DOI: 10.16085/j.issn.1000-6613.2022-0505
• Industrial catalysis • Previous Articles Next Articles
HUANG Wei(), CHU Zheng, REN Lei, LI Shan
Received:
2022-03-28
Revised:
2022-06-11
Online:
2023-02-20
Published:
2023-01-25
Contact:
HUANG Wei
通讯作者:
黄伟
作者简介:
黄伟(1975—),男,硕士,研究方向为精细化学品及催化剂开发。E-mail:huangw.nhgs@sinopec.com。
CLC Number:
HUANG Wei, CHU Zheng, REN Lei, LI Shan. Application of carbon-based solid acid in hydrogenation of nitrobenzene to p-aminophenol[J]. Chemical Industry and Engineering Progress, 2023, 42(1): 272-281.
黄伟, 储政, 任磊, 李珊. 碳基固体酸在硝基苯加氢制备对氨基苯酚中的应用[J]. 化工进展, 2023, 42(1): 272-281.
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URL: https://hgjz.cip.com.cn/EN/10.16085/j.issn.1000-6613.2022-0505
催化剂种类 | 催化剂∶固体酸(mg∶mg) | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% |
---|---|---|---|---|---|---|
1%Pt/C | 1∶200 | 91.8 | 6.4 | 7.0 | 4.4 | 4.8 |
3%Pt/C | 1∶200 | 98.2 | 53 | 53.9 | 29.5 | 30.0 |
3%Pt/C | 2∶200 | 100 | 57.8 | 57.8 | 28.3 | 28.3 |
3%Pt/C | 3∶200 | 100 | 52.8 | 52.8 | 29.7 | 29.7 |
3%Pt/C | 1∶0 | 100 | 0 | 0 | 60.2 | 60.2 |
5%Pt/C | 1∶200 | 90.3 | 42.3 | 46.8 | 10.6 | 11.7 |
5%Pt/C | 2∶200 | 100 | 42.3 | 42.3 | 34.0 | 34.0 |
3%Pd/C | 1∶200 | 91.9 | 20.4 | 22.2 | 15.6 | 17.0 |
催化剂种类 | 催化剂∶固体酸(mg∶mg) | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% |
---|---|---|---|---|---|---|
1%Pt/C | 1∶200 | 91.8 | 6.4 | 7.0 | 4.4 | 4.8 |
3%Pt/C | 1∶200 | 98.2 | 53 | 53.9 | 29.5 | 30.0 |
3%Pt/C | 2∶200 | 100 | 57.8 | 57.8 | 28.3 | 28.3 |
3%Pt/C | 3∶200 | 100 | 52.8 | 52.8 | 29.7 | 29.7 |
3%Pt/C | 1∶0 | 100 | 0 | 0 | 60.2 | 60.2 |
5%Pt/C | 1∶200 | 90.3 | 42.3 | 46.8 | 10.6 | 11.7 |
5%Pt/C | 2∶200 | 100 | 42.3 | 42.3 | 34.0 | 34.0 |
3%Pd/C | 1∶200 | 91.9 | 20.4 | 22.2 | 15.6 | 17.0 |
固体酸的酸度/mmol·g-1 | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% |
---|---|---|---|---|---|
0.282 | 100 | 5.0 | 5.0 | 43.3 | 43.3 |
0.354 | 100 | 5.3 | 5.3 | 39.3 | 39.3 |
0.438 | 100 | 7.8 | 7.8 | 42.1 | 42.1 |
1.454 | 100 | 21.8 | 21.8 | 38.8 | 38.8 |
1.650 | 100 | 26.5 | 26.5 | 39.8 | 39.8 |
1.776 | 100 | 34.5 | 34.5 | 37.4 | 37.4 |
1.962 | 100 | 57.8 | 57.8 | 28.3 | 28.3 |
2.316 | 100 | 46.2 | 46.2 | 32.8 | 32.8 |
固体酸的酸度/mmol·g-1 | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% |
---|---|---|---|---|---|
0.282 | 100 | 5.0 | 5.0 | 43.3 | 43.3 |
0.354 | 100 | 5.3 | 5.3 | 39.3 | 39.3 |
0.438 | 100 | 7.8 | 7.8 | 42.1 | 42.1 |
1.454 | 100 | 21.8 | 21.8 | 38.8 | 38.8 |
1.650 | 100 | 26.5 | 26.5 | 39.8 | 39.8 |
1.776 | 100 | 34.5 | 34.5 | 37.4 | 37.4 |
1.962 | 100 | 57.8 | 57.8 | 28.3 | 28.3 |
2.316 | 100 | 46.2 | 46.2 | 32.8 | 32.8 |
固体酸用量/mg | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% | 亚硝基苯选择性/% | 苯基羟胺选择性/% |
---|---|---|---|---|---|---|---|
100 | 100 | 29.5 | 29.5 | 41.5 | 41.5 | 0 | 0 |
200 | 100 | 46.2 | 46.2 | 32.8 | 32.8 | 0.41 | 0 |
300 | 100 | 66.8 | 66.8 | 21.2 | 21.2 | 0.45 | 0.09 |
400 | 100 | 20.1 | 20.1 | 18.7 | 18.7 | 0.32 | 0.37 |
固体酸用量/mg | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% | 亚硝基苯选择性/% | 苯基羟胺选择性/% |
---|---|---|---|---|---|---|---|
100 | 100 | 29.5 | 29.5 | 41.5 | 41.5 | 0 | 0 |
200 | 100 | 46.2 | 46.2 | 32.8 | 32.8 | 0.41 | 0 |
300 | 100 | 66.8 | 66.8 | 21.2 | 21.2 | 0.45 | 0.09 |
400 | 100 | 20.1 | 20.1 | 18.7 | 18.7 | 0.32 | 0.37 |
反应时间/h | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% | 苯基羟胺/mmol·L-1 | 亚硝基苯/mmol·L-1 |
---|---|---|---|---|---|---|---|
1 | 89.6 | 1.2 | 1.3 | 2.1 | 2.4 | 6.94 | 1.63 |
3 | 90.6 | 2.8 | 3.1 | 6.0 | 6.6 | 17.70 | 2.41 |
5 | 90.3 | 4.3 | 4.8 | 6.9 | 7.7 | 19.09 | 2.46 |
1→5(升温)→10 | 100 | 44.9 | 44.9 | 28.4 | 28.4 | 12.34 | 1.86 |
10(85℃) | 100 | 46.2 | 46.2 | 32.8 | 32.8 | 0 | 0.48 |
反应时间/h | 硝基苯转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺收率/% | 苯胺选择性/% | 苯基羟胺/mmol·L-1 | 亚硝基苯/mmol·L-1 |
---|---|---|---|---|---|---|---|
1 | 89.6 | 1.2 | 1.3 | 2.1 | 2.4 | 6.94 | 1.63 |
3 | 90.6 | 2.8 | 3.1 | 6.0 | 6.6 | 17.70 | 2.41 |
5 | 90.3 | 4.3 | 4.8 | 6.9 | 7.7 | 19.09 | 2.46 |
1→5(升温)→10 | 100 | 44.9 | 44.9 | 28.4 | 28.4 | 12.34 | 1.86 |
10(85℃) | 100 | 46.2 | 46.2 | 32.8 | 32.8 | 0 | 0.48 |
V硝基苯/mL | 固体酸用量/mg | 硝基苯 转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺 收率/% | 苯胺 选择性/% |
---|---|---|---|---|---|---|
0.06 | 200 | 100 | 67.6 | 67.6 | 30.1 | 30.1 |
0.12 | 200 | 100 | 46.2 | 46.2 | 32.8 | 32.8 |
0.24 | 200 | 95.9 | 29.1 | 30.3 | 18.7 | 19.5 |
V硝基苯/mL | 固体酸用量/mg | 硝基苯 转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺 收率/% | 苯胺 选择性/% |
---|---|---|---|---|---|---|
0.06 | 200 | 100 | 67.6 | 67.6 | 30.1 | 30.1 |
0.12 | 200 | 100 | 46.2 | 46.2 | 32.8 | 32.8 |
0.24 | 200 | 95.9 | 29.1 | 30.3 | 18.7 | 19.5 |
气体类型 | 固体酸用量 /mg | 硝基苯转化率 /% | 对氨基苯酚收率 /% | 对氨基苯酚选择性 /% | 苯胺收率 /% | 苯胺选择性 /% | 亚硝基苯收率 /% | 氧化偶氮苯收率 /% |
---|---|---|---|---|---|---|---|---|
0.4MPa H2 | 200 | 100 | 36.9 | 36.9 | 36.1 | 36.1 | 0.36 | 0 |
0.4MPa H2 | 0 | 100 | 0 | 0 | 78.3 | 78.3 | 0.67 | 0 |
N2 | 200 | 95.7 | 44.6 | 46.6 | 8.5 | 8.9 | 1.49 | 0.03 |
气体类型 | 固体酸用量 /mg | 硝基苯转化率 /% | 对氨基苯酚收率 /% | 对氨基苯酚选择性 /% | 苯胺收率 /% | 苯胺选择性 /% | 亚硝基苯收率 /% | 氧化偶氮苯收率 /% |
---|---|---|---|---|---|---|---|---|
0.4MPa H2 | 200 | 100 | 36.9 | 36.9 | 36.1 | 36.1 | 0.36 | 0 |
0.4MPa H2 | 0 | 100 | 0 | 0 | 78.3 | 78.3 | 0.67 | 0 |
N2 | 200 | 95.7 | 44.6 | 46.6 | 8.5 | 8.9 | 1.49 | 0.03 |
固体酸 | 硝基苯 转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺 收率/% | 苯胺 选择性/% |
---|---|---|---|---|---|
未循环 | 100 | 34.5 | 34.5 | 37.4 | 37.4 |
循环使用3次 | 100 | 0.7 | 0.7 | 43.1 | 43.1 |
固体酸 | 硝基苯 转化率/% | 对氨基苯酚收率/% | 对氨基苯酚选择性/% | 苯胺 收率/% | 苯胺 选择性/% |
---|---|---|---|---|---|
未循环 | 100 | 34.5 | 34.5 | 37.4 | 37.4 |
循环使用3次 | 100 | 0.7 | 0.7 | 43.1 | 43.1 |
催化剂种类 | 比表面积/m2·g-1 | 孔容/cm3·g-1 | 介孔尺寸/nm |
---|---|---|---|
1% Pt/C | 1556.3 | 1.23 | 5.02 |
3% Pt/C | 1543.8 | 1.24 | 4.80 |
5% Pt/C | 1447.6 | 1.14 | 4.81 |
3% Pd/C | 1390.3 | 1.10 | 5.00 |
催化剂种类 | 比表面积/m2·g-1 | 孔容/cm3·g-1 | 介孔尺寸/nm |
---|---|---|---|
1% Pt/C | 1556.3 | 1.23 | 5.02 |
3% Pt/C | 1543.8 | 1.24 | 4.80 |
5% Pt/C | 1447.6 | 1.14 | 4.81 |
3% Pd/C | 1390.3 | 1.10 | 5.00 |
固体酸的酸度/mmol·g-1 | 比表面积/m2·g-1 | 孔容/cm3·g-1 | 介孔尺寸/nm |
---|---|---|---|
0.282 | 3.8756 | 0.0250 | 7.3793 |
1.962 | 4.5528 | 0.0260 | 7.2610 |
1.776 | 5.0573 | 0.0225 | 7.1140 |
1.454 | 5.1077 | 0.0244 | 7.2200 |
1.650 | 5.3612 | 0.0236 | 7.0779 |
0.438 | 5.3905 | 0.0228 | 7.1300 |
0.354 | 5.5090 | 0.0254 | 7.3345 |
循环3次 | 5.6299 | 0.0282 | 7.1935 |
2.316 | 11.2202 | 0.0378 | 6.9448 |
固体酸的酸度/mmol·g-1 | 比表面积/m2·g-1 | 孔容/cm3·g-1 | 介孔尺寸/nm |
---|---|---|---|
0.282 | 3.8756 | 0.0250 | 7.3793 |
1.962 | 4.5528 | 0.0260 | 7.2610 |
1.776 | 5.0573 | 0.0225 | 7.1140 |
1.454 | 5.1077 | 0.0244 | 7.2200 |
1.650 | 5.3612 | 0.0236 | 7.0779 |
0.438 | 5.3905 | 0.0228 | 7.1300 |
0.354 | 5.5090 | 0.0254 | 7.3345 |
循环3次 | 5.6299 | 0.0282 | 7.1935 |
2.316 | 11.2202 | 0.0378 | 6.9448 |
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