Journal
INTERNATIONAL JOURNAL OF CHEMICAL KINETICS
Volume 42, Issue 4, Pages 221-225Publisher
JOHN WILEY & SONS INC
DOI: 10.1002/kin.20476
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Funding
- National Science Foundation-Undergraduate Research Center Program [CHE-0532242]
- Northern Plains Undergraduate Research Center (NPURC)
- NASA Space Grant [NGT5-40042]
- Augustana College
- Augustana Research and Artists Fund grant program (ARAF)
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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 E(a) (79 kJ/mol), Delta H(double dagger) (75 kJ/mol), and Delta S(double dagger) (220 J/(mol K)) were the same for all three amine reactants, consistent with a report that Ea 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. (C) 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 221-225, 2010
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