(560dh) A Novel Process for Selective O-Alkylation of Hydroquinone Using Methanol over Ionic Liquids
AIChE Annual Meeting
2019
2019 AIChE Annual Meeting
Catalysis and Reaction Engineering Division
Poster Session: Catalysis and Reaction Engineering (CRE) Division
Wednesday, November 13, 2019 - 3:30pm to 5:00pm
A
novel process for selective o-alkylation of hydroquinone using methanol
over ionic liquids
of hydroquinone (HQ) is presented with methanol as methylating agent cum
solvent in presence of ionic liquid as a catalyst. Different types of ionic
liquids based on imidazole, pyridine and triethylamine named IL1, IL2, IL3, IL4
and IL5 were explored. A catalytic amount of benzoquinone (BQ) was also used to
promote the reaction between hydroquinone and methanol under acidic conditions
to selectively produce 4MP. IL2 was found to be the most active and selective
for synthesis of 4MP. Reaction parameters like temperature, reactants
concentration, catalyst loading and reaction time were also optimized. 100%
selectivity for 4MP with 94.03% conversion of HQ was obtained at optimized
reaction conditions- 65°C temperature, 10 wt% HQ, 1.5 wt% BQ along
with 2.5 wt% IL2 catalyst loading and 2 h reaction time. A protocol for
recovery and reuse of IL catalyst from reaction mixture was also developed and
had shown reusability upto five times without significant loss in its
activity. A plausible reaction mechanism for o-methylation of HQ into
4MP in presence of acidic catalyst has been proposed. Reaction at mild
conditions, short reaction time, excellent yield of desired product, easy
method for catalyst recovery and reusability are advantages of this method over
other reported methods. Pseudo first order reaction
kinetic model parameters were also estimated from the experimental data based
on proposed mechanism. The rate constant of reaction at 65°C
temperatures is calculated as 0.077 min-1 with 55.70 kJ/mol
activation energy.
novel process for selective o-alkylation of hydroquinone using methanol
over ionic liquids
Priyanka V.
Bhongale; Sunil S. Joshi*
Chemical
Engineering and Process Development Division, CSIR-National Chemical
Laboratory, Dr. Homi Bhaba Road, Pune-411008, India
pv.bhongale@ncl.res.in;
ss.joshi@ncl.res.in
Fax: +91 20 25902621.
Tel: +91 20 25902745. E-mail: ss.joshi@ncl.res.in
of hydroquinone (HQ) is presented with methanol as methylating agent cum
solvent in presence of ionic liquid as a catalyst. Different types of ionic
liquids based on imidazole, pyridine and triethylamine named IL1, IL2, IL3, IL4
and IL5 were explored. A catalytic amount of benzoquinone (BQ) was also used to
promote the reaction between hydroquinone and methanol under acidic conditions
to selectively produce 4MP. IL2 was found to be the most active and selective
for synthesis of 4MP. Reaction parameters like temperature, reactants
concentration, catalyst loading and reaction time were also optimized. 100%
selectivity for 4MP with 94.03% conversion of HQ was obtained at optimized
reaction conditions- 65°C temperature, 10 wt% HQ, 1.5 wt% BQ along
with 2.5 wt% IL2 catalyst loading and 2 h reaction time. A protocol for
recovery and reuse of IL catalyst from reaction mixture was also developed and
had shown reusability upto five times without significant loss in its
activity. A plausible reaction mechanism for o-methylation of HQ into
4MP in presence of acidic catalyst has been proposed. Reaction at mild
conditions, short reaction time, excellent yield of desired product, easy
method for catalyst recovery and reusability are advantages of this method over
other reported methods. Pseudo first order reaction
kinetic model parameters were also estimated from the experimental data based
on proposed mechanism. The rate constant of reaction at 65°C
temperatures is calculated as 0.077 min-1 with 55.70 kJ/mol
activation energy.
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