3-Hydroxypropanoic acid

April 27, 2015
Image of 3-Hydroxypropanoic acid 3D Image of 3-Hydroxypropanoic acid

3-Hydroxypropanoic acid (3-HP) is a β-hydroxy acid that is soluble in water and many oxygenated organic solvents. It can be produced biochemically and used to make a variety of industrial chemicals, especially acrylic acid, its esters, and their polymers.

3-HP can be directly produced from renewable resources or made from another biobased chemical, levulinic acid. When levulinic acid undergoes hydrogen peroxide oxidation in base, 3-HP or, under different conditions, its hydroperoxy cousin is produced. The peroxide can be hydrogenated to 3-HP.

In an unusual example of pH-driven selectivity, if the reaction is run in acid, the product is succinic acid rather than 3-HP. In both cases, the terminal methyl group of levulinic acid is cleaved.

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