Aerobic Oxidation of Cyclopentane by Using Fluorinated <I>N</I>-Hydroxyphthalimide Derivatives

Samar Kumar Guha; Yasutaka Ishii

doi:doi:10.11648/j.sjc.20200802.13

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Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives

Samar Kumar Guha, Yasutaka Ishii

Published in Science Journal of Chemistry (Volume 8, Issue 2)

Received: 3 March 2020 Accepted: 7 April 2020 Published: 28 April 2020

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Abstract

N-Hydroxyphthalimide derivatives, F₁₅- and F₁₇-NHPI, bearing fluorinated carboxylate and alkyl chains, respectively, were prepared and their catalytic performances were compared with those of N-hydroxyphthalimide (NHPI). Thus, the oxidation of cyclopentane under 10 atm of air in the presence of catalytic amount of fluorinated NHPI or NHPI, Co(OAc)₂, and Mn(OAc)₂ in TFT as solvent at 100°C afforded cyclopentanol, cyclopentanone, succinic acid and glutaric acid. It was assumed that F-NHPI derivatives bearing electron withdrawing fluorocarbon groups showed higher catalytic activity than the NHPI by enhancement of the electrophilicity of N-oxy radicals generated from the F-NHPI derivatives. In the oxidation of cyclopentane, F-NHPI showed better catalytic activity than NHPI. Cyclopentanol and glutaric acid were obtained as the major products in case of NHPI, whereas, cyclopentanone and glutaric acid were obtained as the major products in case of fluorinated NHPIs. However, only glutaric acid was obtained as the major product when a increased amount of Co(OAc)₂ was used in the present ocidation by using NHPI or F-NHPIs. The effect of temperature and air was also investigated in the oxidation of cyclopentane. When the oxidation was performed at 90°C, cyclopentanol was obtained as the major product, whereas, no significant changes were observed when the reaction was performed at 20 atm instead of 10 atm. The great advantage of the fluorinated NHPI derivatives is that it could be recovered after the oxidation.

Published in	Science Journal of Chemistry (Volume 8, Issue 2)
DOI	10.11648/j.sjc.20200802.13
Page(s)	36-41
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2020. Published by Science Publishing Group

Keywords

Aerobic Oxidation, Cyclopentane, F-NHPI Catalyst, Recovery

References

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APA Style

Samar Kumar Guha, Yasutaka Ishii. (2020). Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives. Science Journal of Chemistry, 8(2), 36-41. https://doi.org/10.11648/j.sjc.20200802.13

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ACS Style

Samar Kumar Guha; Yasutaka Ishii. Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives. Sci. J. Chem. 2020, 8(2), 36-41. doi: 10.11648/j.sjc.20200802.13

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AMA Style

Samar Kumar Guha, Yasutaka Ishii. Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives. Sci J Chem. 2020;8(2):36-41. doi: 10.11648/j.sjc.20200802.13

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@article{10.11648/j.sjc.20200802.13,
  author = {Samar Kumar Guha and Yasutaka Ishii},
  title = {Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives},
  journal = {Science Journal of Chemistry},
  volume = {8},
  number = {2},
  pages = {36-41},
  doi = {10.11648/j.sjc.20200802.13},
  url = {https://doi.org/10.11648/j.sjc.20200802.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20200802.13},
  abstract = {N-Hydroxyphthalimide derivatives, F15- and F17-NHPI, bearing fluorinated carboxylate and alkyl chains, respectively, were prepared and their catalytic performances were compared with those of N-hydroxyphthalimide (NHPI). Thus, the oxidation of cyclopentane under 10 atm of air in the presence of catalytic amount of fluorinated NHPI or NHPI, Co(OAc)2, and Mn(OAc)2 in TFT as solvent at 100°C afforded cyclopentanol, cyclopentanone, succinic acid and glutaric acid. It was assumed that F-NHPI derivatives bearing electron withdrawing fluorocarbon groups showed higher catalytic activity than the NHPI by enhancement of the electrophilicity of N-oxy radicals generated from the F-NHPI derivatives. In the oxidation of cyclopentane, F-NHPI showed better catalytic activity than NHPI. Cyclopentanol and glutaric acid were obtained as the major products in case of NHPI, whereas, cyclopentanone and glutaric acid were obtained as the major products in case of fluorinated NHPIs. However, only glutaric acid was obtained as the major product when a increased amount of Co(OAc)2 was used in the present ocidation by using NHPI or F-NHPIs. The effect of temperature and air was also investigated in the oxidation of cyclopentane. When the oxidation was performed at 90°C, cyclopentanol was obtained as the major product, whereas, no significant changes were observed when the reaction was performed at 20 atm instead of 10 atm. The great advantage of the fluorinated NHPI derivatives is that it could be recovered after the oxidation.},
 year = {2020}
}

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TY  - JOUR
T1  - Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives
AU  - Samar Kumar Guha
AU  - Yasutaka Ishii
Y1  - 2020/04/28
PY  - 2020
N1  - https://doi.org/10.11648/j.sjc.20200802.13
DO  - 10.11648/j.sjc.20200802.13
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 36
EP  - 41
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20200802.13
AB  - N-Hydroxyphthalimide derivatives, F15- and F17-NHPI, bearing fluorinated carboxylate and alkyl chains, respectively, were prepared and their catalytic performances were compared with those of N-hydroxyphthalimide (NHPI). Thus, the oxidation of cyclopentane under 10 atm of air in the presence of catalytic amount of fluorinated NHPI or NHPI, Co(OAc)2, and Mn(OAc)2 in TFT as solvent at 100°C afforded cyclopentanol, cyclopentanone, succinic acid and glutaric acid. It was assumed that F-NHPI derivatives bearing electron withdrawing fluorocarbon groups showed higher catalytic activity than the NHPI by enhancement of the electrophilicity of N-oxy radicals generated from the F-NHPI derivatives. In the oxidation of cyclopentane, F-NHPI showed better catalytic activity than NHPI. Cyclopentanol and glutaric acid were obtained as the major products in case of NHPI, whereas, cyclopentanone and glutaric acid were obtained as the major products in case of fluorinated NHPIs. However, only glutaric acid was obtained as the major product when a increased amount of Co(OAc)2 was used in the present ocidation by using NHPI or F-NHPIs. The effect of temperature and air was also investigated in the oxidation of cyclopentane. When the oxidation was performed at 90°C, cyclopentanol was obtained as the major product, whereas, no significant changes were observed when the reaction was performed at 20 atm instead of 10 atm. The great advantage of the fluorinated NHPI derivatives is that it could be recovered after the oxidation.
VL  - 8
IS  - 2
ER  -

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Author Information

Samar Kumar Guha

Department of Arts and Sciences, Ahsanullah University of Science and Technology, Dhaka, Bangladesh
Yasutaka Ishii

Department of Chemistry and Materials Engineering, Kansai University, Suita, Osaka, Japan

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APA Style

Samar Kumar Guha, Yasutaka Ishii. (2020). Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives. Science Journal of Chemistry, 8(2), 36-41. https://doi.org/10.11648/j.sjc.20200802.13

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ACS Style

Samar Kumar Guha; Yasutaka Ishii. Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives. Sci. J. Chem. 2020, 8(2), 36-41. doi: 10.11648/j.sjc.20200802.13

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AMA Style

Samar Kumar Guha, Yasutaka Ishii. Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives. Sci J Chem. 2020;8(2):36-41. doi: 10.11648/j.sjc.20200802.13

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@article{10.11648/j.sjc.20200802.13,
  author = {Samar Kumar Guha and Yasutaka Ishii},
  title = {Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives},
  journal = {Science Journal of Chemistry},
  volume = {8},
  number = {2},
  pages = {36-41},
  doi = {10.11648/j.sjc.20200802.13},
  url = {https://doi.org/10.11648/j.sjc.20200802.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20200802.13},
  abstract = {N-Hydroxyphthalimide derivatives, F15- and F17-NHPI, bearing fluorinated carboxylate and alkyl chains, respectively, were prepared and their catalytic performances were compared with those of N-hydroxyphthalimide (NHPI). Thus, the oxidation of cyclopentane under 10 atm of air in the presence of catalytic amount of fluorinated NHPI or NHPI, Co(OAc)2, and Mn(OAc)2 in TFT as solvent at 100°C afforded cyclopentanol, cyclopentanone, succinic acid and glutaric acid. It was assumed that F-NHPI derivatives bearing electron withdrawing fluorocarbon groups showed higher catalytic activity than the NHPI by enhancement of the electrophilicity of N-oxy radicals generated from the F-NHPI derivatives. In the oxidation of cyclopentane, F-NHPI showed better catalytic activity than NHPI. Cyclopentanol and glutaric acid were obtained as the major products in case of NHPI, whereas, cyclopentanone and glutaric acid were obtained as the major products in case of fluorinated NHPIs. However, only glutaric acid was obtained as the major product when a increased amount of Co(OAc)2 was used in the present ocidation by using NHPI or F-NHPIs. The effect of temperature and air was also investigated in the oxidation of cyclopentane. When the oxidation was performed at 90°C, cyclopentanol was obtained as the major product, whereas, no significant changes were observed when the reaction was performed at 20 atm instead of 10 atm. The great advantage of the fluorinated NHPI derivatives is that it could be recovered after the oxidation.},
 year = {2020}
}

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TY  - JOUR
T1  - Aerobic Oxidation of Cyclopentane by Using Fluorinated N-Hydroxyphthalimide Derivatives
AU  - Samar Kumar Guha
AU  - Yasutaka Ishii
Y1  - 2020/04/28
PY  - 2020
N1  - https://doi.org/10.11648/j.sjc.20200802.13
DO  - 10.11648/j.sjc.20200802.13
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 36
EP  - 41
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20200802.13
AB  - N-Hydroxyphthalimide derivatives, F15- and F17-NHPI, bearing fluorinated carboxylate and alkyl chains, respectively, were prepared and their catalytic performances were compared with those of N-hydroxyphthalimide (NHPI). Thus, the oxidation of cyclopentane under 10 atm of air in the presence of catalytic amount of fluorinated NHPI or NHPI, Co(OAc)2, and Mn(OAc)2 in TFT as solvent at 100°C afforded cyclopentanol, cyclopentanone, succinic acid and glutaric acid. It was assumed that F-NHPI derivatives bearing electron withdrawing fluorocarbon groups showed higher catalytic activity than the NHPI by enhancement of the electrophilicity of N-oxy radicals generated from the F-NHPI derivatives. In the oxidation of cyclopentane, F-NHPI showed better catalytic activity than NHPI. Cyclopentanol and glutaric acid were obtained as the major products in case of NHPI, whereas, cyclopentanone and glutaric acid were obtained as the major products in case of fluorinated NHPIs. However, only glutaric acid was obtained as the major product when a increased amount of Co(OAc)2 was used in the present ocidation by using NHPI or F-NHPIs. The effect of temperature and air was also investigated in the oxidation of cyclopentane. When the oxidation was performed at 90°C, cyclopentanol was obtained as the major product, whereas, no significant changes were observed when the reaction was performed at 20 atm instead of 10 atm. The great advantage of the fluorinated NHPI derivatives is that it could be recovered after the oxidation.
VL  - 8
IS  - 2
ER  -

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