Knoevenagel condensation reaction catalysed by Al-MOFs with CAU-1 and CAU-10-type structures
The metal–organic frameworks (MOFs) CAU-1-NH 2 ([Al 4 (OH) 2 (OCH 3 ) 4 ( p -BDC-NH 2 ) 3 ], ( p -BDC-NH 2 ) 2− = 2-aminoterephthalate) and CAU-10-NH 2 ([Al(OH)( m -BDC-NH 2 )], ( m -BDC-NH 2 ) 2− = 5-aminoisophthalate) which possess two different pore sizes were studied for their catalytic activity...
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| Published in | CrystEngComm Vol. 19; no. 29; pp. 4187 - 4193 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
2017
|
| Online Access | Get full text |
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| Abstract | The metal–organic frameworks (MOFs) CAU-1-NH
2
([Al
4
(OH)
2
(OCH
3
)
4
(
p
-BDC-NH
2
)
3
], (
p
-BDC-NH
2
)
2−
= 2-aminoterephthalate) and CAU-10-NH
2
([Al(OH)(
m
-BDC-NH
2
)], (
m
-BDC-NH
2
)
2−
= 5-aminoisophthalate) which possess two different pore sizes were studied for their catalytic activity as heterogeneous solid base catalysts in the Knoevenagel condensation reaction between benzaldehyde and malononitrile under mild reaction conditions (40 °C, 7 h, ethanol). For comparison, isoreticular MOFs containing a smaller amount of –NH
2
groups (CAU-1-NH
2
/H) or no –NH
2
groups (CAU-10-H) were synthesized. A two-step synthesis route including the synthesis of CAU-1-NH
2
and its use as crystal seeds was developed to obtain the mixed-linker CAU-1-NH
2
/H compound. Only for CAU-1-NH
2
, up to 100% selectivity towards the desired Knoevenagel condensation product is observed. Hence, the catalytic activity of CAU-1-NH
2
was tested between various benzaldehydes containing different substituents with malononitrile. By employing benzaldehyde and malononitrile as the starting materials, it is found that the mixed-linker MOF CAU-1-NH
2
/H catalyses the formation of the acetal (benzaldehyde diethyl acetal), while both CAU-10 materials lead to mixtures of the two products. Furthermore, the catalyst stability was also examined through reusability and leaching experiments and it is observed that the catalyst can be reused with no significant drop in its activity. |
|---|---|
| AbstractList | The metal–organic frameworks (MOFs) CAU-1-NH
2
([Al
4
(OH)
2
(OCH
3
)
4
(
p
-BDC-NH
2
)
3
], (
p
-BDC-NH
2
)
2−
= 2-aminoterephthalate) and CAU-10-NH
2
([Al(OH)(
m
-BDC-NH
2
)], (
m
-BDC-NH
2
)
2−
= 5-aminoisophthalate) which possess two different pore sizes were studied for their catalytic activity as heterogeneous solid base catalysts in the Knoevenagel condensation reaction between benzaldehyde and malononitrile under mild reaction conditions (40 °C, 7 h, ethanol). For comparison, isoreticular MOFs containing a smaller amount of –NH
2
groups (CAU-1-NH
2
/H) or no –NH
2
groups (CAU-10-H) were synthesized. A two-step synthesis route including the synthesis of CAU-1-NH
2
and its use as crystal seeds was developed to obtain the mixed-linker CAU-1-NH
2
/H compound. Only for CAU-1-NH
2
, up to 100% selectivity towards the desired Knoevenagel condensation product is observed. Hence, the catalytic activity of CAU-1-NH
2
was tested between various benzaldehydes containing different substituents with malononitrile. By employing benzaldehyde and malononitrile as the starting materials, it is found that the mixed-linker MOF CAU-1-NH
2
/H catalyses the formation of the acetal (benzaldehyde diethyl acetal), while both CAU-10 materials lead to mixtures of the two products. Furthermore, the catalyst stability was also examined through reusability and leaching experiments and it is observed that the catalyst can be reused with no significant drop in its activity. |
| Author | Stock, Norbert Heidenreich, Niclas Dhakshinamoorthy, Amarajothi Lenzen, Dirk |
| Author_xml | – sequence: 1 givenname: Amarajothi orcidid: 0000-0003-0991-6608 surname: Dhakshinamoorthy fullname: Dhakshinamoorthy, Amarajothi organization: School of Chemistry, Madurai Kamaraj University, Madurai-625 021, India, Institut fur Anorganische Chemie – sequence: 2 givenname: Niclas surname: Heidenreich fullname: Heidenreich, Niclas organization: Institut fur Anorganische Chemie, Christian-Albrechts-Universität, 24118 Kiel, Germany – sequence: 3 givenname: Dirk surname: Lenzen fullname: Lenzen, Dirk organization: Institut fur Anorganische Chemie, Christian-Albrechts-Universität, 24118 Kiel, Germany – sequence: 4 givenname: Norbert orcidid: 0000-0002-0339-7352 surname: Stock fullname: Stock, Norbert organization: Institut fur Anorganische Chemie, Christian-Albrechts-Universität, 24118 Kiel, Germany |
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| SSID | ssj0014110 |
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| Snippet | The metal–organic frameworks (MOFs) CAU-1-NH
2
([Al
4
(OH)
2
(OCH
3
)
4
(
p
-BDC-NH
2
)
3
], (
p
-BDC-NH
2
)
2−
= 2-aminoterephthalate) and CAU-10-NH
2... |
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| StartPage | 4187 |
| Title | Knoevenagel condensation reaction catalysed by Al-MOFs with CAU-1 and CAU-10-type structures |
| Volume | 19 |
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