History and Discovery

Dodecanedioic acid was first synthesized in 1886 by German chemist Carl Harries through the hydrolysis and oxidation of castor oil. However, it was not until the 1950s that its potential as an industrial chemical started to be realized. In the 1950s, researchers at DuPont discovered that decamethylenedicarboxylic acid could serve as a building block for producing nylon polymers. This kickstarted research into scaling up production of decamethylenedicarboxylic acid and utilizing it commercially.

Chemical Properties and Structure

Decamethylenedicarboxylic acid, also called Dodecandioic Acid, is an α,ω-dicarboxylic acid with the formula HOOC(CH2)10COOH. It consists of a linear hydrocarbon chain with carboxyl groups at both ends. Decamethylenedicarboxylic acid is a white, odorless solid with a melting point of around 100°C. It has limited solubility in water but is highly soluble in many organic solvents such as alcohols, acetone, and ethyl acetate. Chemically, it is classified as a dicarboxylic acid due to the presence of two carboxyl functional groups. These carboxyl groups make decamethylenedicarboxylic acid highly reactive and able to undergo condensation polymerization reactions.

Production Methods

Currently, the primary industrial production method for decamethylenedicarboxylic acid involves hydrogenation of petroleum-derived mixtures containing unsaturated dicarboxylic acids. In this process, a mixture of cis- and trans- isomers of undecenedioic acid is first obtained by ozonolysis of olefin derivatives from cracking of paraffin waxes. This unsaturated acid mixture is then hydrogenated over a nickel catalyst to yield decamethylenedicarboxylic acid. Overall yields from this process are around 70-80%. Alternative bio-based production routes are also being explored using oleaginous yeast or algae that can metabolize vegetable oils to produce decamethylenedicarboxylic acid. However, petroleum-based hydrogenation remains the dominant commercial production method due to its lower costs compared to fermentation methods currently.

Applications in Plastics and Polymer Manufacturing

By far the largest use of decamethylenedicarboxylic acid is in the production of nylon polymers, accounting for over 90% of its demand. In this application, decamethylenedicarboxylic acid reacts with diamines such as 1,6-hexanediamine to form nylon salts through condensation polymerization. These nylon salts can then be melt-spun or solution-spun into nylon polymers. Nylon made from decamethylenedicarboxylic acid, known as nylon 612, exhibits desirable properties such as good mechanical strength, abrasion resistance, and thermal stability. As a result, nylon 612 finds wide use in engineering resins, monofilaments, fibers, and plastic packaging. Decamethylenedicarboxylic acid is also used as a co-monomer for manufacturing polyesters through reaction with diols. Polyesters made with decamethylenedicarboxylic acid exhibit flexibility and clarity superior to terephthalate-based polyesters. On a smaller scale, decamethylenedicarboxylic acid derivatives also serve as additives and plasticizers for other resins and polymers.

Regulations and Health/Safety

Like other dicarboxylic acids, decamethylenedicarboxylic acid is classified as an skin and eye irritant. The recommended occupational exposure limit set by the ACGIH is 5 mg/m3 as an 8-hour time-weighted average concentration. Above this level, prolonged skin or eye contact with the vapor or liquid form could cause irritation. However, risks are substantially lower when standard safety practices are followed during industrial production and handling of the chemical. No major adverse environmental impacts have been reported from decamethylenedicarboxylic acid itself. However, emissions from the petroleum- based production process do contribute to greenhouse gas emissions and require treatment. Some jurisdictions have also classified certain petroleum-derived process waste streams containing decamethylenedicarboxylic acid as hazardous. Overall regulatory focus is on minimizing occupational exposures and emissions during commercial scale manufacturing.

Due to its versatility as a building block for polymers, the demand for Dodecanedioic acid is expected to steadily rise in tandem with the growing plastics industry worldwide. Manufacturers are continuing efforts to develop more eco-friendly and renewable production routes, such as through fermentation of plant oils. However, petroleum-based hydrogenation is likely to remain the leading production method given its process efficiency and economies of scale. Innovation in applications is also expanding the uses of decamethylenedicarboxylic acid-derived polymers in high performance films, coatings and specialty blends. With improved production technologies and new market opportunities, decamethylenedicarboxylic acid looks poised to retain its important role as an indispensable industrial chemical input for plastics and polymer manufacturing in the decades ahead.

Get more insights on Dodecanedioic acid

About Author:

Money Singh is a seasoned content writer with over four years of experience in the market research sector. Her expertise spans various industries, including food and beverages, biotechnology, chemical and materials, defense and aerospace, consumer goods, etc. (https://www.linkedin.com/in/money-singh-590844163)