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The Enzymatic Synthesis and Characterization of Disolketal Iminodiacetic Acid (DSIDA)

  • Original Paper
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Journal of the American Oil Chemists' Society

Abstract

Disolketal iminodiacetic acid (DSIDA) has been synthesized from the enzyme-catalyzed condensation reaction between derivatives of iminodiacetic acid (IDA) and glycerol. According to all available literature, DSIDA is a novel diester that has never been synthesized. It is a precursor to water-soluble polyhydric alcohols and helps to address the global need of the biodiesel industry to find new uses for glycerol. Reacting diMe-IDA with solketal, a protected glycerol, produced DSIDA in yields as high as 96.4% under optimal reaction conditions of 70 °C and 200 Torr for 24 h. The reaction was monitored using ATR-IR and a validated GC method. ATR-IR monitored the disappearance of the primary solketal alcohol and the appearance of cyclic solketal ether bonds in the molecular backbone of the intermediates and product. Structural analysis of the intermediates and products was performed using two-dimensional NMR, GC, GC–MS and elemental analysis. All spectral data was in agreement with the proposed structures for the chemical reaction. Thermal profiles were determined by TGA to be single-stage decompositions above 160 °C.

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Acknowledgements

Mr. Edward Wickham and Dr. Pheobie Qi are acknowledged for their assistance with the collection of IR data.

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Authors and Affiliations

  1. Sustainable Biofuels and Coproducts Research Unit, United States Department of Agriculture, Agricultural Research Service, Eastern Regional Research Center, 600 East Mermaid Lane, Wyndmoor, PA, 19038, USA

    Victor T. Wyatt, Gary D. Strahan & Kerby Jones

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  1. Victor T. Wyatt
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  2. Gary D. Strahan
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  3. Kerby Jones
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Correspondence to Victor T. Wyatt.

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Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture. ARS is an equal opportunity provider and employer.

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Wyatt, V.T., Strahan, G.D. & Jones, K. The Enzymatic Synthesis and Characterization of Disolketal Iminodiacetic Acid (DSIDA). J Am Oil Chem Soc 93, 1683–1695 (2016). https://doi.org/10.1007/s11746-016-2911-9

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