Is Azelaic Acid natural?

Oleic acid from sunflower, rapeseed or tallow, cleaved by ozone or hydrogen peroxide. The co-product pelargonic acid carries the other nine carbons.

The dominant industrial synthesis of Azelaic Acid (Nonanedioic Acid) is achieved through the oxidative cleavage of oleic acid, a C18 monounsaturated fatty acid. The most common method is ozonolysis, where oleic acid is reacted with ozone (O3) at low temperatures, typically between -20°C and 0°C, in a suitable solvent like methanol or acetic acid. This reaction cleaves the double bond in oleic acid, forming intermediate ozonides.

Following ozonolysis, the ozonides are reductively or oxidatively worked up. A common reductive workup involves using a reducing agent such as zinc dust or dimethyl sulfide to yield nonanal and azelaic acid. Alternatively, an oxidative workup, often using hydrogen peroxide or peroxy acids, can also be employed to directly yield azelaic acid and other oxidation products. The reaction conditions, particularly temperature control and the choice of solvent and workup reagents, are critical for maximizing yield and purity.

Purification of the crude Azelaic Acid is a crucial step to obtain cosmetic-grade material. This typically involves a series of steps including extraction, crystallization, and sometimes distillation or chromatography. Recrystallization from water or organic solvents is a common method to remove impurities such as nonanoic acid (pelargonic acid), which is a co-product of the ozonolysis of oleic acid, and residual starting materials or reagents. The final product is a white crystalline powder.

Azelaic acid is a dicarboxylic acid that occurs naturally in wheat, rye, and barley. In cosmetics, it's often produced through a process that starts with oleic acid, a fatty acid found in vegetable oils like olive or sunflower oil. This natural origin makes it a "mostly renewable" ingredient according to cosmetic industry standards.

Its production involves a chemical reaction called ozonolysis, where ozone is used to break down the oleic acid molecule. This process is carefully controlled at low temperatures to ensure efficiency and purity. After the reaction, the azelaic acid is purified through steps like crystallization to remove any byproducts, resulting in a high-quality ingredient suitable for skincare products.