Database/Surfactant/Sodium Cocoamphoacetate
Mostly natural · ISO 16128

Is Sodium Cocoamphoacetate natural?

Mostly. The coco fatty acyl chain and sodium ion are natural, but the aminoethylethanolamine and chloroacetate that build the amphoacetate head group are petrochemical.

INCI nameSodium Cocoamphoacetate
CAS90387-76-1
FunctionSurfactant · Skin Conditioning Agent
FeedstockMade by condensing coconut fatty acid with aminoethylethanolamine…

How we scored it

Coco lauroyl C12H23O 183 Da natural + Na+ 23 Da natural = 206 Da; AEEA/chloroacetate-derived head group C6H12N2O3 160 Da petrochemical; total 366 Da; 206/366 = 0.56
What counts. ISO 16128-2 scores the atoms that remain in the final ingredient. Reagents, solvents, catalysts and protecting groups used during manufacture leave no mass behind and are not counted.

Where it comes from

Made by condensing coconut fatty acid with aminoethylethanolamine to an amidoamine/imidazoline, then ring-opening with sodium chloroacetate to install the glycine-acetate group. The fatty chain is coconut-derived; the amine and chloroacetate reagents are petrochemical.

The industrial synthesis of Sodium Cocoamphoacetate involves two main steps. First, fatty acids are extracted from coconut oil, typically through hydrolysis and subsequent fractionation. These fatty acids, primarily lauric acid and myristic acid, are then reacted with glycine. This reaction is an amidation process where the carboxylic acid group of the fatty acid reacts with the amine group of glycine to form an amide bond, releasing water. This step is often carried out at elevated temperatures, typically between 100-150°C, under atmospheric pressure or slight vacuum to facilitate water removal and drive the reaction to completion.

The second step involves the reaction of the resulting fatty acid-glycine intermediate with sodium chloroacetate. This is an alkylation reaction where the secondary amine of the fatty acid-glycine intermediate reacts with sodium chloroacetate. This reaction is typically performed in an aqueous or aqueous-alcoholic medium, often in the presence of a base such as sodium hydroxide to neutralize the hydrochloric acid formed as a byproduct and to facilitate the formation of the sodium salt of the final product. The reaction temperature is generally maintained between 50-80°C.

Following the reaction, the crude product undergoes purification. This usually involves filtration to remove any insoluble impurities, followed by pH adjustment to ensure the desired amphoteric properties. The final product is typically supplied as an aqueous solution, with concentrations ranging from 30-40%. The purification process aims to remove unreacted starting materials, byproducts, and inorganic salts to meet cosmetic grade specifications. The amphoteric nature of Sodium Cocoamphoacetate, meaning it can act as either an acid or a base, is a key characteristic derived from its chemical structure, featuring both acidic carboxylate groups and basic amine groups.

In plain English

Sodium Cocoamphoacetate is a gentle cleansing ingredient derived from coconut oil and an amino acid called glycine. It's known for its mildness, making it suitable for sensitive skin and baby products. It works by attracting both oily and water-based dirt, allowing it to be easily washed away from the skin or hair.

This ingredient is created through a two-step process. First, the natural fatty acids from coconut oil are combined with glycine. Then, this mixture is further reacted to create the final cleansing agent. Because it starts with natural materials like coconut oil, it's considered partially renewable, contributing to its favorable environmental profile.

CosIng definition: Glycine, N-(2-aminoethyl)-N-(2-hydroxyethyl)-, N-coco-acyl derivatives, monosodium salts

Natural alternatives with the same function

References

  1. 1ISO 16128-1:2016 and ISO 16128-2:2017 — Guidelines on technical definitions and criteria for natural and organic cosmetic ingredients and products. ISO, Geneva.
  2. 2SODIUM COCOAMPHOACETATE. CosIng — European Commission cosmetic ingredient database. ec.europa.eu/cosing ↗
  3. 3SODIUM COCOAMPHOACETATE. CosIng u2014 European Commission database for information on cosmetic substances and ingredients. https://ec.europa.eu/growth/tools-databases/cosing/search?search=SODIUM%20COCOAMPHOACETATE