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Modeling of toluene acetylation with acetic anhydride on H-USY zeolite

Eileen A Dejaegere, Joris Thybaut UGent, Guy Marin UGent, Gino V Baron and Joeri FM Denayer (2011) INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH. 50(21). p.1822-1832
abstract
The liquid-phase acetylation of toluene with acetic anhydride was carried out in a continuous-flow reactor over H-USY zeolites with different Si/Al ratios at 180 degrees C, at different contact times and feed compositions. H-USY is an active catalyst for this reaction because the main reaction products at all times on stream are the desired methylacetophenone (MAP) and its reaction byproduct acetic acid. Within the different MAP isomers, the selectivity toward 4-MAP equals 85%. Although the initial acetic anhydride conversion is 100%, the zeolite is subject to deactivation. Small amounts of side products such as methylbenzoic acid and isopropenyltoluene were also identified and their formation explained. The data and insights obtained during these experiments were used to obtain models describing the formation of MAP and the other components present in the reactor effluent. The most plausible model, obtained via model discrimination, was validated at different reaction conditions and takes into account adsorption of the chemical compounds, the catalytic reactions, and deactivation of the catalyst. It also includes hydrolysis of acetic anhydride and the formation of side products originating from MAP. According to this model, catalyst deactivation starts from MAP and acetic anhydride, whereby acetic acid is liberated. Fitting of the model to the experimental data shows that the kinetic constant for the formation of 4-MAP is comparable to that of the deactivation reaction.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
FINE CHEMICALS SYNTHESIS, FRIEDEL-CRAFTS ACYLATION, AROMATIC-COMPOUNDS, PHYSICOCHEMICAL PROPERTIES, SOLID SOLVENTS, BETA ZEOLITES, Y-ZEOLITES, CATALYSTS, ANISOLE, DEACTIVATION
journal title
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
Ind. Eng. Chem. Res.
volume
50
issue
21
pages
1822 - 1832
Web of Science type
Article
Web of Science id
000296128300007
JCR category
ENGINEERING, CHEMICAL
JCR impact factor
2.237 (2011)
JCR rank
30/132 (2011)
JCR quartile
1 (2011)
ISSN
0888-5885
DOI
10.1021/ie2007906
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1981778
handle
http://hdl.handle.net/1854/LU-1981778
date created
2012-01-10 15:38:58
date last changed
2017-03-09 12:39:38
@article{1981778,
  abstract     = {The liquid-phase acetylation of toluene with acetic anhydride was carried out in a continuous-flow reactor over H-USY zeolites with different Si/Al ratios at 180 degrees C, at different contact times and feed compositions. H-USY is an active catalyst for this reaction because the main reaction products at all times on stream are the desired methylacetophenone (MAP) and its reaction byproduct acetic acid. Within the different MAP isomers, the selectivity toward 4-MAP equals 85\%. Although the initial acetic anhydride conversion is 100\%, the zeolite is subject to deactivation. Small amounts of side products such as methylbenzoic acid and isopropenyltoluene were also identified and their formation explained. The data and insights obtained during these experiments were used to obtain models describing the formation of MAP and the other components present in the reactor effluent. The most plausible model, obtained via model discrimination, was validated at different reaction conditions and takes into account adsorption of the chemical compounds, the catalytic reactions, and deactivation of the catalyst. It also includes hydrolysis of acetic anhydride and the formation of side products originating from MAP. According to this model, catalyst deactivation starts from MAP and acetic anhydride, whereby acetic acid is liberated. Fitting of the model to the experimental data shows that the kinetic constant for the formation of 4-MAP is comparable to that of the deactivation reaction.},
  author       = {Dejaegere, Eileen A and Thybaut, Joris and Marin, Guy and Baron, Gino V and Denayer, Joeri FM},
  issn         = {0888-5885},
  journal      = {INDUSTRIAL \& ENGINEERING CHEMISTRY RESEARCH},
  keyword      = {FINE CHEMICALS SYNTHESIS,FRIEDEL-CRAFTS ACYLATION,AROMATIC-COMPOUNDS,PHYSICOCHEMICAL PROPERTIES,SOLID SOLVENTS,BETA ZEOLITES,Y-ZEOLITES,CATALYSTS,ANISOLE,DEACTIVATION},
  language     = {eng},
  number       = {21},
  pages        = {1822--1832},
  title        = {Modeling of toluene acetylation with acetic anhydride on H-USY zeolite},
  url          = {http://dx.doi.org/10.1021/ie2007906},
  volume       = {50},
  year         = {2011},
}

Chicago
Dejaegere, Eileen A, Joris Thybaut, Guy Marin, Gino V Baron, and Joeri FM Denayer. 2011. “Modeling of Toluene Acetylation with Acetic Anhydride on H-USY Zeolite.” Industrial & Engineering Chemistry Research 50 (21): 1822–1832.
APA
Dejaegere, E. A., Thybaut, J., Marin, G., Baron, G. V., & Denayer, J. F. (2011). Modeling of toluene acetylation with acetic anhydride on H-USY zeolite. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 50(21), 1822–1832.
Vancouver
1.
Dejaegere EA, Thybaut J, Marin G, Baron GV, Denayer JF. Modeling of toluene acetylation with acetic anhydride on H-USY zeolite. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH. 2011;50(21):1822–32.
MLA
Dejaegere, Eileen A, Joris Thybaut, Guy Marin, et al. “Modeling of Toluene Acetylation with Acetic Anhydride on H-USY Zeolite.” INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH 50.21 (2011): 1822–1832. Print.