Measurement of p -toluenesulfonic acid-catalyzed reaction kinetics of 1,2-propylene glycol acetylation using in situ 1H NMR spectroscopy

Arati Santhanakrishnan, Lars Peereboom, Dennis J. Miller, Adina Dumitrascu, Patrick B. Smith

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Abstract

The reaction kinetics for the acetylation of 1,2-propylene glycol (PG) catalyzed by p-toluenesulfonic acid (p-TSA) were determined using an in situ1H NMR method. Both primary and secondary monoacetate esters of PG were observed as well as the diester. The reaction kinetics were characterized as a function of PG to acetic acid (AA) stoichiometry, p-TSA concentration, and temperature. The acetylation reactions and the transacetylation of the diester with PG were modeled as reversible second order reactions. Equilibrium constants were determined experimentally for each reaction. Activation energies for the consecutive acetylation of PG and PG monoacetate ester (PGMA) were 56 and 47 kJ/mol, respectively. The activation energy for intermolecular transacetylation of PG with its diacetate ester to form PG monoacetate was 63 kJ/mol.

Original languageEnglish (US)
Pages (from-to)9337-9342
Number of pages6
JournalIndustrial and Engineering Chemistry Research
Volume52
Issue number27
DOIs
StatePublished - Jul 10 2013

Profile

Propylene Glycol
Acetylation
Magnetic Resonance Spectroscopy
Acids
Glycols
Propylene
Actinium
Esters
Reaction kinetics
Benin
Activation energy
African Swine Fever
Acetic Acid
Temperature
Equilibrium constants
Acetic acid
Stoichiometry
Nuclear magnetic resonance spectroscopy
Nuclear magnetic resonance
Acetanilides

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)
  • Industrial and Manufacturing Engineering

Cite this

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title = "Measurement of p -toluenesulfonic acid-catalyzed reaction kinetics of 1,2-propylene glycol acetylation using in situ 1H NMR spectroscopy",
abstract = "The reaction kinetics for the acetylation of 1,2-propylene glycol (PG) catalyzed by p-toluenesulfonic acid (p-TSA) were determined using an in situ1H NMR method. Both primary and secondary monoacetate esters of PG were observed as well as the diester. The reaction kinetics were characterized as a function of PG to acetic acid (AA) stoichiometry, p-TSA concentration, and temperature. The acetylation reactions and the transacetylation of the diester with PG were modeled as reversible second order reactions. Equilibrium constants were determined experimentally for each reaction. Activation energies for the consecutive acetylation of PG and PG monoacetate ester (PGMA) were 56 and 47 kJ/mol, respectively. The activation energy for intermolecular transacetylation of PG with its diacetate ester to form PG monoacetate was 63 kJ/mol.",
author = "Arati Santhanakrishnan and Lars Peereboom and Miller, {Dennis J.} and Adina Dumitrascu and Smith, {Patrick B.}",
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pages = "9337--9342",
journal = "Industrial & Engineering Chemistry Product Research and Development",
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publisher = "American Chemical Society",
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T1 - Measurement of p -toluenesulfonic acid-catalyzed reaction kinetics of 1,2-propylene glycol acetylation using in situ 1H NMR spectroscopy

AU - Santhanakrishnan,Arati

AU - Peereboom,Lars

AU - Miller,Dennis J.

AU - Dumitrascu,Adina

AU - Smith,Patrick B.

PY - 2013/7/10

Y1 - 2013/7/10

N2 - The reaction kinetics for the acetylation of 1,2-propylene glycol (PG) catalyzed by p-toluenesulfonic acid (p-TSA) were determined using an in situ1H NMR method. Both primary and secondary monoacetate esters of PG were observed as well as the diester. The reaction kinetics were characterized as a function of PG to acetic acid (AA) stoichiometry, p-TSA concentration, and temperature. The acetylation reactions and the transacetylation of the diester with PG were modeled as reversible second order reactions. Equilibrium constants were determined experimentally for each reaction. Activation energies for the consecutive acetylation of PG and PG monoacetate ester (PGMA) were 56 and 47 kJ/mol, respectively. The activation energy for intermolecular transacetylation of PG with its diacetate ester to form PG monoacetate was 63 kJ/mol.

AB - The reaction kinetics for the acetylation of 1,2-propylene glycol (PG) catalyzed by p-toluenesulfonic acid (p-TSA) were determined using an in situ1H NMR method. Both primary and secondary monoacetate esters of PG were observed as well as the diester. The reaction kinetics were characterized as a function of PG to acetic acid (AA) stoichiometry, p-TSA concentration, and temperature. The acetylation reactions and the transacetylation of the diester with PG were modeled as reversible second order reactions. Equilibrium constants were determined experimentally for each reaction. Activation energies for the consecutive acetylation of PG and PG monoacetate ester (PGMA) were 56 and 47 kJ/mol, respectively. The activation energy for intermolecular transacetylation of PG with its diacetate ester to form PG monoacetate was 63 kJ/mol.

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