Tall Oil Fatty Acid Chemical Properties

EPA Substance Registry System

Tall oil fatty acids (61790-12-3)

Tall Oil Fatty Acid Usage And Synthesis

Description

Tall oil fatty acid is derived from pine oil, the main components are the mixture of oleic acid, linoleic acid and its isomers, and contains a small amount of rosin acid and unsaponifiable matter. It can undergo alcoholization, ammonia (amination) reaction.

Properties

Tall oil fatty acid is a low-cost unsaturated fatty acid (oleic acid) that is a mixture of oleic acid, linoleic acid and their isomers. It is insoluble in water, soluble in ether and ethanol; it can react with alkali, and can also undergo alcoholization and ammonia (amine) reaction.

Uses

Tall oil fatty acids are mainly used to prepare oilfield chemicals and ore flotation agents, and can also be used to produce dimerized and trimerized fatty acids used in the coating industry.

Definition

Crude tall oil (CTO) is not a fatty oil. However, it is actually a mixture of five components with different boiling points, which are split by fractionation into heads (which boils first), then ‘tall oil fatty acids’ (TOFAs), distilled tall oil (DTO, a mixture of fatty and rosin acids), ‘tall oil rosin’ (TOR, a mixture of eight closely related rosin acids, i.e., abietic, neoabietic, palustric, levopimaric, dehydroabietic, pimaric, sandaracopimaric, and isopimaric acid), and pitch (the unsaponifiable residue). TOFA is mainly oleic acid. Furthermore, TOFAs contain unusual isomers, such as octadecadienoic acids with double bonds in the 5,9- and 5,12-positions. Important applications of TOFA are the manufacture of alkyd resins and dimer acids[1].

Application

Tall oil fatty acids are a by-product of the wood pulp industry when pine wood chips are digested and chemically treated. It is produced mainly in North America and Scandinavia, with the two oils differing somewhat in composition due to the tree species used. Either oil, however, is used to produce dimer acids, alkyols and coatings, detergents, and lubricants. There are future possibilities for use as solvents, inks, and biodiesel production.

References

[1] T.W. Abraham.“10.01 – Introduction: Polymers for a Sustainable Environment and Green Energy.” Polymer Science: A Comprehensive Reference (2012).

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