Abstract
Quaternary ammonium compounds are produced worldwide in hundreds of millions of pound volume annually for a plethora of end-uses from fabric-care formulations to asphalt emulsifiers, typically from nongreen alkylating reagents. The kinetics of a reaction employing dimethyl carbonate (DMC) as a green alkylating agent was investigated using three trialkylamines (tributylamine, trihexylamine, and trioctylamine) at several temperatures. Arrhenius and Eyring analysis of the data showed that values of Ea (79 kJ/mol), ΔH‡ (75 kJ/mol), and ΔS‡ (220 J/(mol K)) were the same for all three amine reactants, consistent with a report that E a is independent of alkyl chain length when the chain length is greater than three carbons. Although rates are significantly slower with DMC than with other alkylating reagents, the resulting methyl carbonate anion has advantages for clean anion metathesis, which is important for some applications, especially those involving ionic liquids.
| Original language | English |
|---|---|
| Pages (from-to) | 221-225 |
| Number of pages | 5 |
| Journal | International Journal of Chemical Kinetics |
| Volume | 42 |
| Issue number | 4 |
| DOIs | |
| State | Published - Apr 2010 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Inorganic Chemistry
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Kinetic study of the reaction of dimethyl carbonate with trialkylamines. / Weisshaar, Duane E.; Earl, Gary W.; Villa, Eric; Zierke, Jessica L.; Fry, Christopher J.; Becvar, Kara L.; Li, Shik Ki; Schafer, Matthew C.
In: International Journal of Chemical Kinetics, Vol. 42, No. 4, 04.2010, p. 221-225.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Kinetic study of the reaction of dimethyl carbonate with trialkylamines
AU - Weisshaar, Duane E.
AU - Earl, Gary W.
AU - Villa, Eric
AU - Zierke, Jessica L.
AU - Fry, Christopher J.
AU - Becvar, Kara L.
AU - Li, Shik Ki
AU - Schafer, Matthew C.
PY - 2010/4
Y1 - 2010/4
N2 - Quaternary ammonium compounds are produced worldwide in hundreds of millions of pound volume annually for a plethora of end-uses from fabric-care formulations to asphalt emulsifiers, typically from nongreen alkylating reagents. The kinetics of a reaction employing dimethyl carbonate (DMC) as a green alkylating agent was investigated using three trialkylamines (tributylamine, trihexylamine, and trioctylamine) at several temperatures. Arrhenius and Eyring analysis of the data showed that values of Ea (79 kJ/mol), ΔH‡ (75 kJ/mol), and ΔS‡ (220 J/(mol K)) were the same for all three amine reactants, consistent with a report that E a is independent of alkyl chain length when the chain length is greater than three carbons. Although rates are significantly slower with DMC than with other alkylating reagents, the resulting methyl carbonate anion has advantages for clean anion metathesis, which is important for some applications, especially those involving ionic liquids.
AB - Quaternary ammonium compounds are produced worldwide in hundreds of millions of pound volume annually for a plethora of end-uses from fabric-care formulations to asphalt emulsifiers, typically from nongreen alkylating reagents. The kinetics of a reaction employing dimethyl carbonate (DMC) as a green alkylating agent was investigated using three trialkylamines (tributylamine, trihexylamine, and trioctylamine) at several temperatures. Arrhenius and Eyring analysis of the data showed that values of Ea (79 kJ/mol), ΔH‡ (75 kJ/mol), and ΔS‡ (220 J/(mol K)) were the same for all three amine reactants, consistent with a report that E a is independent of alkyl chain length when the chain length is greater than three carbons. Although rates are significantly slower with DMC than with other alkylating reagents, the resulting methyl carbonate anion has advantages for clean anion metathesis, which is important for some applications, especially those involving ionic liquids.
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U2 - 10.1002/kin.20476
DO - 10.1002/kin.20476
M3 - Article
VL - 42
SP - 221
EP - 225
JO - International Journal of Chemical Kinetics
JF - International Journal of Chemical Kinetics
SN - 0538-8066
IS - 4
ER -