Project Details Solubility of Crystalline Alkanoic Acids, Alkenoic Acids, Alkanedioic Acids and Alkenedioic Acids Dissolved in Neat Organic Solvents, Organic Solvent Mixtures, and Aqueous-Organic Solvent Mixtures

Project No.:
2021-007-1-500
Start Date:
07 April 2021
End Date:

Objective

The 105 volumes in the IUPAC-NIST Solubility Data Series deal primarily with solubility of gases and inorganic salts. Very few of the volumes pertain to solubility of crystalline organic compounds in dissolved in organic mono-solvents and in binary organic solvent mixtures. The proposed volume will extend the coverage of the Solubility Data Series to include crystalline alkanoic acids, alkenoic acids and alkanedioic acids, and will incorporate measurement uncertainty into the compilations to the extent possible. The fore-mentioned classes of carboxylic acids are used in the manufacture of soaps and skin cleansing creams, cosmetics, lubricants, pharmaceuticals and in photographic and food packing materials.

Description

There are currently 105 volumes in the IUPAC-NIST Solubility Data Series. Most of the volumes deal with the solubility of gases and inorganic salts. Very few of the volumes deal with the solubility of crystalline organic compounds in dissolved in organic mono-solvents and in binary organic solvent mixtures. The proposed volume will extend the coverage of the Solubility Data Series to include crystalline alkanoic acids, alkenoic acids and alkanedioic acids. These classes of organic compounds are found to occur naturally in vegetable oils (peanut oil, palm oil and corn oil) and fish. The fore-mentioned classes of carboxylic acids are used in the manufacture of soaps and skin cleansing creams, cosmetics, lubricants, pharmaceuticals and in photographic and food packing materials.

The project will provide individuals working in several different industries with compilations, critical evaluations and measurement uncertainties (where possible) for the solubilities of several industrially important organic compounds. For example, the primary use of lauric acid is in the production of soaps and cosmetics. Published studies have shown that lauric acid exhibits strong antimicrobial properties against Gram-positive bacteria. Its use in the treatment of inflammatory acne has been examined in vitro and in vivo using laboratory animals. Esters prepared from the esterification of lauric acid with short chain alcohols are used as precursors for the synthesis of several pharmaceutical products and agrochemicals, and also as synthetic scents and food odorants. Also saturated fatty acids have sometimes been used as taste-masking agents in pharmaceutical formations to mask the unpleasant taste of the active medicinal drug compound.

Progress

This volume in the IUPAC–NIST Solubility Data Series is devoted to the solubility of crystalline alkanoic acids, alkenoic acids, alkanedioic acids, and alkenedioic acids dissolved in neat organic solvents, organic solvent mixtures, and aqueous–organic solvent mixtures. The volume will be published in three separate parts, with each part representing a compilation and evaluation of published solubility data for different classes of organic carboxylic acids. Nearly 110 years of the published chemical and engineering literature were searched during the preparation of this volume.

Update Oct 2021 – Paper I of the volume reports the solubility of 15 alkanoic acids.
> W. E. Acree, Jr. and W. E. Waghorne, J. Phys. Chem. Ref. Data 50, 043103 (2021). https://doi.org/10.1063/5.0062574

Update Dec 2021 – Paper II of the volume discuss the solubility of the following ten alkenoic acids: (E)-docos-13-enoic acid (also called brassidic acid), (2E)-but-2-enoic acid (also called trans-crotonic acid), (9E)-octadec-9-enoic acid (also called elaidic acid), (Z)-docos-13-enoic acid (also called erucic acid), (9Z,12Z)-9,12-octadecadienoic acid (also called linoleic acid), octadecatrienoic acid (also called linolenic acid), 2-methylpropenoic acid (also called methacrylic acid), (9Z)-octadec-9-enoic acid (also called oleic acid), (6E)-octadec-6-enoic acid (also called petroselaidic acid), and (6Z)-octadec-6-enoic acid (also called petroselenic acid). One alkynoic acid, 9-octadecynoic acid (also called 9-stearolic acid), is also included in Paper II.
> W. E. Acree, Jr. and W. E. Waghorne, J. Phys. Chem. Ref. Data 50, 043105 (2021); https://doi.org/10.1063/5.0067051

The concluding part of the three-part series will consider the solubility for several alkanedioic acids and alkenedioic acids dissolved in both organic mono-solvents and binary solvent mixtures. In total, solubility data for 45 different carboxylic acids will be contained in this volume.

Project update published in Chem Int April 2022, p. 30

Page last update 8 Apr 2022

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