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Chemical Characterization and Physical Properties of Solvents Derived from Epoxidized Methyl Soyate

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Reactions of epoxidized methyl soyate (EMS) with alcohols, carbon dioxide, and acetone yielded liquids with solvent properties that make them more suitable than methyl soyate for dissolving polar substances. The reactions of EMS in the presence of Amberlyst-15 with alcohols, including methanol, ethanol, n-butanol, and 2-methoxyethanol, produced a series of solvents containing ether (–OR) and alcohol (–OH) groups. Reactions of EMS with carbon dioxide and acetone gave products with carbonate and ketonide functional groups, respectively. The complex mixture of compounds present in the product, EMS(MeOH), resulting from the reaction of EMS with MeOH, was characterized by MS and NMR investigations. In addition to products resulting from MeOH addition across the epoxide ring, were major amounts of cyclic tetrahydrofuran derivatives that were derived from reactions of methyl linoleate (18:2) with MeOH. All of the solvents were characterized by high boiling points and low vapor pressures. Their viscosities were higher than that of methyl soyate. Especially notable were their very high Kauri-butanol values, which ranged from 280 to 852, all of which are much higher than that (57) of methyl soyate. Such high KB values indicate that these solvents have very favorable solubilizing properties, which is illustrated by the ability of EMS(MeOH) to readily dissolve both polar (e.g., MeOH) and non-polar (e.g., hexane) compounds.

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Abbreviations

ESO:

Epoxidized soybean oil

EMS:

Epoxidized methyl soyate

FAME:

Fatty acid methyl ester(s)

mCPBA:

meta-chloroperbenzoic acid

NMR:

Nuclear magnetic resonance spectroscopy

LC–MS:

Liquid chromatography-mass spectrometry

APCI:

Atmospheric pressure chemical ionization

TBAB:

Tetra(n-butyl)ammonium bromide

KB:

Kauri-butanol

VOC:

Volatile organic compound(s)

Cr(acac)3 :

Chromium tris-acetylacetonate

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Acknowledgments

The authors thank the United Soybean Board for support. ESO was kindly provided by Arkema and ChemCeed. HOSO was kindly supplied by Stratas Foods.

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Authors and Affiliations

  1. Department of Chemistry, Gilman Hall, Iowa State University, Ames, IA, 50011–3111, USA

    Sean J. Riley, John G. Verkade & Robert J. Angelici

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  1. Sean J. Riley
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  2. John G. Verkade
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  3. Robert J. Angelici
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Correspondence to Robert J. Angelici.

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Riley, S.J., Verkade, J.G. & Angelici, R.J. Chemical Characterization and Physical Properties of Solvents Derived from Epoxidized Methyl Soyate. J Am Oil Chem Soc 92, 589–601 (2015). https://doi.org/10.1007/s11746-015-2607-6

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  • DOI: https://doi.org/10.1007/s11746-015-2607-6

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