Clean Technologies and Environmental Policy

, Volume 19, Issue 4, pp 1169–1180 | Cite as

Novel alkali-promoted hydrotalcite for selective synthesis of 2-methoxy phenyl benzoate from guaiacol and benzoic anhydride

Original Paper
First Online:
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Accepted:

Abstract

Esters find several applications such as solvents, flavours and fragrants and intermediates in synthesis of drugs. In the present work, 2-methoxy phenyl benzoate was efficiently synthesized from guaiacol and benzoic anhydride by acylation. A variety of catalysts such as hydrotalcite and alkali-promoted hydrotalcite was synthesized. Potassium-promoted hydrotalcite (K/HT) calcined at 500 °C for 6 h was active, selective and reusable. It was characterized by different techniques. A slurry batch reactor was used to study reaction mechanism and kinetics. 2-Methoxy phenyl benzoate was efficiently obtained with 100% selectivity at guaiacol conversion of 98% over K/HT at 100 °C after 6 h. A power law model with second-order kinetics was fitted to obtain an apparent activation energy of reaction of 21.1 kcal mol−1. The process is clean and green.

Keywords

Guaiacol Hydrotalcite Catalyst Loading Aromatic Ketone Potassium Oxide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

List of symbols

A

Reactant species A, guaiacol

B

Reactant species B, benzoic anhydride

D

Product species D, 2-methoxy phenyl benzoate

E

Product species E, benzoic acid

AS1

Chemisorbed guaiacol on vacant sites of type S 1

BS2

Chemisorbed benzoic anhydride on vacant sites of type S 2

DS2

Chemisorbed 2-methoxy phenyl benzoate on vacant sites of type S 2

ES1

Chemisorbed benzoic acid on vacant sites of type S 1

CA

Concentration of A, guaiacol (mol L−1)

\(C_{{A_{0} }}\)

Initial concentration of A in bulk liquid phase (mol L−1)

\(C_{{AS_{1} }}\)

Adsorption concentration of A on active site S 1 (mol g−1 of cat)

CB

Concentration of B, benzoic anhydride (mol L−1)

\(C_{{B_{0} }}\)

Initial concentration of B in bulk liquid phase (mol L−1)

\(C_{{BS_{2} }}\)

Adsorption concentration of B on active site S 2 (mol g−1 of cat)

CD

Concentration of D, 2-methoxy phenyl benzoate (mol L−1)

\(C_{{DS_{2} }}\)

Concentration of D on active sites of type S 2 (mol g−1 of cat)

CE

Concentration of E, benzoic acid (mol L−1)

\(C_{{ES_{1} }}\)

Concentration of E on active sites of type S 1 (mol g−1 of cat)

\(C_{{S_{1} }}\)

Concentration of vacant sites of type S 1 (mol g−1 of cat)

\(C_{{S_{2} }}\)

Concentration of vacant sites of type S 2 (mol g−1of cat)

\(C_{{{\text{T}}_{1} }}\)

Total concentration of vacant sites of type S 1 (mol g−1 of cat)

\(C_{{{\text{T}}_{2} }}\)

Total concentration of vacant sites of type S 2 (mol g−1 of cat)

CT

Total concentration of sites (mol g−1 of cat)

KA

Adsorption constant for A (L mol−1)

KB

Adsorption constant for B (L mol−1)

KD

Adsorption constant for D (L mol−1)

KE

Adsorption constant for E (L mol−1)

1/KD

Desorption constant for D from catalyst site S 2 (L mol−1)

1/KE

Desorption constant for E from catalyst site S 1 (L mol−1)

k1

Forward reaction rate constant for surface reaction (L2 mol−1 s−1 g-cat−1)

\(k_{1}^{\prime }\)

Backward reaction rate constant for surface reaction (L2 mol−1 s−1 g-cat−1)

k2

Second-order rate constant (L mol−1 s−1)

M

Molar ratio of \({{C_{{B_{0} }} } \mathord{\left/ {\vphantom {{C_{{B_{0} }} } {C_{{A_{0} }} }}} \right. \kern-0pt} {C_{{A_{0} }} }}\)

−rA

Rate of reaction (mol L−1 min−1)

w

Catalyst loading (g L−1)

XA

Fractional conversion of A

t

Time (min)

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Notes

Acknowledgements

S.L.B. expresses thanks to the UGC for giving basic research (senior) fellowship. G.D.Y. acknowledges support from R. T. Mody Distinguished Professor Endowment of ICT and J. C. Bose National Fellowship of DST-GOI.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

10098_2016_1316_MOESM1_ESM.docx (82 kb)
Supplementary material 1 (DOCX 82 kb)

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Copyright information

© Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  1. 1.Department of Chemical EngineeringInstitute of Chemical TechnologyMumbaiIndia

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