Transesterification of ethylacetoacetate catalysed by metal free mesoporous carbon nitride

Chokkalingam Anand, Subramaniam Vishnu Priya, Geoffrey Lawrence, Gurudas P. Mane, Dattatray Dhawale, Kumaresapillai S. Prasad, Veerappan V. Balasubramanian, Mohammad A. Wahab, Ajayan Vinu

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The basic catalytic performance of the mesoporous carbon nitride (MCN) for the transesterification of ethylacetoacetate with various alcohols such as 1-butanol, 1-octanol, cyclohexanol, benzyl alcohol and furfuryl alcohol under heterogeneous reaction conditions without using any solvents was demonstrated. The catalyst was prepared by using a nano-hard templating approach through a simple polymerisation reaction between ethylenediamine (EDA) and carbon tetrachloride (CTC) in the mesochannels of the SBA-15 followed by the carbonisation and the silica removal by HF. The material was thoroughly analysed by sophisticated characterisation techniques such as X-ray diffraction (XRD), N2 adsorption studies, high resolution transmission electron microscopy (HRTEM), X-ray photoelectron spectroscopy and CHN analysis. Structural investigation of the MCN by XRD, HRTEM and N2 adsorption revealed that the prepared catalyst exhibits highly ordered two-dimensional (2D) porous arrays with a high surface area and a large pore volume. The catalytic results revealed that the MCN was found to be an efficient catalyst in transesterifying long and short chain primary alcohols, and cyclic and aromatic alcohols to afford their corresponding β-keto esters in high yields. More importantly, the catalyst was highly active when 1-butanol was used. The influence of various parameters such as temperature, reactant feed ratio, catalyst weight, and time-on-stream on the yield of the final product was studied in detail. In addition, the activity of the catalyst was also compared with pure mesoporous carbon and the results were discussed. The recyclability studies revealed that the MCN catalyst was highly stable under the rigorous reaction conditions and can be reused several times without any significant loss of catalytic activity. Crown

Original languageEnglish
Pages (from-to)164-169
Number of pages6
JournalCatalysis Today
Volume204
DOIs
Publication statusPublished - 15 Apr 2013
Externally publishedYes

Fingerprint

Carbon nitride
Transesterification
Metals
Catalysts
Alcohols
1-Butanol
ethylenediamine
High resolution transmission electron microscopy
Butenes
Cyclohexanols
1-Octanol
Benzyl Alcohol
Adsorption
X ray diffraction
Carbon tetrachloride
Carbon Tetrachloride
Carbonization
cyanogen
Silicon Dioxide
Catalyst activity

Keywords

  • β-Keto esters
  • Carbon nitride
  • Ethylenediamine
  • Mesoporous
  • SBA-15

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Transesterification of ethylacetoacetate catalysed by metal free mesoporous carbon nitride. / Anand, Chokkalingam; Priya, Subramaniam Vishnu; Lawrence, Geoffrey; Mane, Gurudas P.; Dhawale, Dattatray; Prasad, Kumaresapillai S.; Balasubramanian, Veerappan V.; Wahab, Mohammad A.; Vinu, Ajayan.

In: Catalysis Today, Vol. 204, 15.04.2013, p. 164-169.

Research output: Contribution to journalArticle

Anand, C, Priya, SV, Lawrence, G, Mane, GP, Dhawale, D, Prasad, KS, Balasubramanian, VV, Wahab, MA & Vinu, A 2013, 'Transesterification of ethylacetoacetate catalysed by metal free mesoporous carbon nitride', Catalysis Today, vol. 204, pp. 164-169. https://doi.org/10.1016/j.cattod.2012.07.025
Anand, Chokkalingam ; Priya, Subramaniam Vishnu ; Lawrence, Geoffrey ; Mane, Gurudas P. ; Dhawale, Dattatray ; Prasad, Kumaresapillai S. ; Balasubramanian, Veerappan V. ; Wahab, Mohammad A. ; Vinu, Ajayan. / Transesterification of ethylacetoacetate catalysed by metal free mesoporous carbon nitride. In: Catalysis Today. 2013 ; Vol. 204. pp. 164-169.
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AU - Lawrence, Geoffrey

AU - Mane, Gurudas P.

AU - Dhawale, Dattatray

AU - Prasad, Kumaresapillai S.

AU - Balasubramanian, Veerappan V.

AU - Wahab, Mohammad A.

AU - Vinu, Ajayan

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AB - The basic catalytic performance of the mesoporous carbon nitride (MCN) for the transesterification of ethylacetoacetate with various alcohols such as 1-butanol, 1-octanol, cyclohexanol, benzyl alcohol and furfuryl alcohol under heterogeneous reaction conditions without using any solvents was demonstrated. The catalyst was prepared by using a nano-hard templating approach through a simple polymerisation reaction between ethylenediamine (EDA) and carbon tetrachloride (CTC) in the mesochannels of the SBA-15 followed by the carbonisation and the silica removal by HF. The material was thoroughly analysed by sophisticated characterisation techniques such as X-ray diffraction (XRD), N2 adsorption studies, high resolution transmission electron microscopy (HRTEM), X-ray photoelectron spectroscopy and CHN analysis. Structural investigation of the MCN by XRD, HRTEM and N2 adsorption revealed that the prepared catalyst exhibits highly ordered two-dimensional (2D) porous arrays with a high surface area and a large pore volume. The catalytic results revealed that the MCN was found to be an efficient catalyst in transesterifying long and short chain primary alcohols, and cyclic and aromatic alcohols to afford their corresponding β-keto esters in high yields. More importantly, the catalyst was highly active when 1-butanol was used. The influence of various parameters such as temperature, reactant feed ratio, catalyst weight, and time-on-stream on the yield of the final product was studied in detail. In addition, the activity of the catalyst was also compared with pure mesoporous carbon and the results were discussed. The recyclability studies revealed that the MCN catalyst was highly stable under the rigorous reaction conditions and can be reused several times without any significant loss of catalytic activity. Crown

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