Chem. J. Chinese Universities ›› 2022, Vol. 43 ›› Issue (6): 20220078.doi: 10.7503/cjcu20220078
• Physical Chemistry • Previous Articles Next Articles
GAO Wenxiu, LYU Jieqiong, GAO Yongping, KONG Changjian, WANG Xueping, GUO Shengnan, LOU Dawei()
Received:
2022-02-04
Online:
2022-06-10
Published:
2022-04-04
Contact:
LOU Dawei
E-mail:dwlou@jlict.edu.cn
Supported by:
CLC Number:
TrendMD:
GAO Wenxiu, LYU Jieqiong, GAO Yongping, KONG Changjian, WANG Xueping, GUO Shengnan, LOU Dawei. Preparation of Ethyl α⁃Cyanocinnamate Catalyzed by Nitrogen-rich Porous Organic Polymers[J]. Chem. J. Chinese Universities, 2022, 43(6): 20220078.
Entry | Catalyst dosage/mg | n(Benzaldehyde)/ n(Ethyl cyanoacetate) | Time/h | Temperature/oC | Solvent | Yield(%) | 103TOF/ (mol·g-1·h-1) |
---|---|---|---|---|---|---|---|
1 | 0 | 1∶1 | 1 | 60 | Methanol | 1 | — |
2 | 15 | 1∶1 | 1 | 60 | Methanol | 55 | 36 |
3 | 15 | 1∶1 | 1 | 60 | Ethanol | 29 | 19 |
4 | 15 | 1∶1 | 1 | 60 | Toluene | 1 | 1 |
5 | 15 | 1∶1 | 1 | 50 | Methanol | 51 | 34 |
6 | 15 | 1∶1 | 1 | 40 | Methanol | 9 | 6 |
7 | 15 | 1∶1.5 | 1 | 60 | Methanol | 62 | 41 |
8 | 15 | 1∶2 | 1 | 60 | Methanol | 65 | 43 |
9 | 10 | 1∶1.5 | 1 | 60 | Methanol | 39 | 39 |
10 | 20 | 1∶1.5 | 3 | 60 | Methanol | 97 | 16 |
11 | 20 | 1∶1.5 | 1 | 60 | Methanol | 88 | 44 |
12 | 20 | 1∶1.5 | 2 | 60 | Methanol | 95 | 24 |
Table 1 Optimization of reaction conditions for the preparation of ethyl α -cyanocinnamate catalyzed by mPMF*
Entry | Catalyst dosage/mg | n(Benzaldehyde)/ n(Ethyl cyanoacetate) | Time/h | Temperature/oC | Solvent | Yield(%) | 103TOF/ (mol·g-1·h-1) |
---|---|---|---|---|---|---|---|
1 | 0 | 1∶1 | 1 | 60 | Methanol | 1 | — |
2 | 15 | 1∶1 | 1 | 60 | Methanol | 55 | 36 |
3 | 15 | 1∶1 | 1 | 60 | Ethanol | 29 | 19 |
4 | 15 | 1∶1 | 1 | 60 | Toluene | 1 | 1 |
5 | 15 | 1∶1 | 1 | 50 | Methanol | 51 | 34 |
6 | 15 | 1∶1 | 1 | 40 | Methanol | 9 | 6 |
7 | 15 | 1∶1.5 | 1 | 60 | Methanol | 62 | 41 |
8 | 15 | 1∶2 | 1 | 60 | Methanol | 65 | 43 |
9 | 10 | 1∶1.5 | 1 | 60 | Methanol | 39 | 39 |
10 | 20 | 1∶1.5 | 3 | 60 | Methanol | 97 | 16 |
11 | 20 | 1∶1.5 | 1 | 60 | Methanol | 88 | 44 |
12 | 20 | 1∶1.5 | 2 | 60 | Methanol | 95 | 24 |
Sample | Element content(%) | Different N content(%) | |||||||
---|---|---|---|---|---|---|---|---|---|
C | O | S | N | —N= | —NH— | —NH2 | π?π* satellite | ||
mPMF | 37.95 | 3.35 | 4.60 | 54.10 | 28.67 | 18.75 | 2.12 | 4.56 | |
SNW?1 | 51.93 | 4.03 | 2.56 | 41.49 | 23.21 | 13.91 | 2.28 | 2.09 |
Table 2 Contents of elements and nitrogen species in mPMF and SNW-1
Sample | Element content(%) | Different N content(%) | |||||||
---|---|---|---|---|---|---|---|---|---|
C | O | S | N | —N= | —NH— | —NH2 | π?π* satellite | ||
mPMF | 37.95 | 3.35 | 4.60 | 54.10 | 28.67 | 18.75 | 2.12 | 4.56 | |
SNW?1 | 51.93 | 4.03 | 2.56 | 41.49 | 23.21 | 13.91 | 2.28 | 2.09 |
Entry | Catalyst | Solvent | Temperature/℃ | Time/h | Yield(%) | 103TOF/(mol·g-1·h-1) | Ref. |
---|---|---|---|---|---|---|---|
1 | mPMF | Methanol | 60 | 1 | 88 | 44 | This work |
2 | SNW?1 | Methanol | 60 | 1 | 72 | 20 | This work |
3 | TMP | H2O | 120 | 0.2 | 85 | 212 | [ |
4 | Ni?Fe?HT | None | 80 | 8 | 85 | 5 | [ |
5 | LDH?ILs?C12 | H2O | RT | 3 | 99 | 11 | [ |
6 | PVAm(9.0)/SBA?15 | Ethanol | 40 | 6 | 100 | 6 | [ |
7 | NH2?MPR | H2O | 30 | 12 | 97 | 5 | [ |
Table 3 Compared with the reported catalysts for the synthesis of ethyl α ?cyanocinnamate*
Entry | Catalyst | Solvent | Temperature/℃ | Time/h | Yield(%) | 103TOF/(mol·g-1·h-1) | Ref. |
---|---|---|---|---|---|---|---|
1 | mPMF | Methanol | 60 | 1 | 88 | 44 | This work |
2 | SNW?1 | Methanol | 60 | 1 | 72 | 20 | This work |
3 | TMP | H2O | 120 | 0.2 | 85 | 212 | [ |
4 | Ni?Fe?HT | None | 80 | 8 | 85 | 5 | [ |
5 | LDH?ILs?C12 | H2O | RT | 3 | 99 | 11 | [ |
6 | PVAm(9.0)/SBA?15 | Ethanol | 40 | 6 | 100 | 6 | [ |
7 | NH2?MPR | H2O | 30 | 12 | 97 | 5 | [ |
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