by Dodecanedioic acid, also known as DDDA or simply 12DA, is an organic compound classified as a dicarboxylic acid. With the formula C11H20O4, it consists of a hydrocarbon chain of 12 carbon atoms with carboxyl groups (COOH) at each end. DDDA is an important industrial raw material that has many commercial applications. In this article, we will explore the properties, production, uses and future prospects of this dicarboxylic acid.
Properties and Structure of DDDA
DDDA is a crystalline solid at room temperature that melts at around 110°C. Its density is slightly higher than water at 1.026 g/cm3. Chemically, DDDA is classified as an aliphatic dicarboxylic acid due to the presence of two carboxyl functional groups at opposite ends of its 12-carbon chain. The carboxyl groups give DDDA the amphiphilic property of being partially soluble in both organic solvents as well as water. In terms of structure, DDDA has a linear hydrocarbon backbone that allows for flexibility. However, the rigidity imposed by the two COOH groups results in DDDA having a rod-like or rigid crystalline structure. These unique structural and physicochemical properties enable DDDA to be used in a variety of industrial applications.
Industrial Production of DDDA
DDDA is produced commercially on an industrial scale through various synthetic routes. Some of the major production methods include:
– Oxidation of Dodecane: In this hydrocarbon oxidation process, dodecane (C12H26) is oxidized to DDDA using oxygen in the presence of catalysts like cobalt or manganese. This is currently the most common industrial route.
– Hydrolysis of Adiponitrile: Adiponitrile can be synthesized from butadiene followed by hydrolysis to yield DDDA.
– Carbonylation of Olefin: Ethylene or 1-butene undergoes carbonylation and subsequent oxidation to produce DDDA.
Typical production facilities have capacities of 10,000-40,000 metric tons per year. Major producers include BASF, Cathay Industrial Biotech, UBE Industries among others. While oxidation of dodecane remains the dominant process, newer biomass-based routes are being explored to produce DDDA more sustainably.
Uses and Applications of DDDA
Given its unique properties, DDDA finds extensive use in various industrial sectors:
– Nylon production: DDDA is a chief monomer used in the manufacture of certain nylon polymers, such as Nylon-12 and aromatic nylon. These nylons have high strength, chemical resistance.
– Plasticizers: Being a relatively non-toxic plasticizer, DDDA is used to impart flexibility to PVC plastics. It provides low volatility and good low-temperature properties.
– Coatings: DDDA acts as a hardener and crosslinking agent in coatings, inks, and adhesives formulations. It imparts excellent durability, adhesion and abrasion resistance.
– Lubricants: Esters and amides of DDDA make excellent base stocks for high-performance lubricating oils and greases offering benefits such as low pour points.
– Others: It also has applications as a monomer for polyesters, nylon resins, epoxy curing agent, and intermediate for agricultural chemicals, personal care products and more.
With the wide range of uses, the global DDDA market is expected see steady growth in the coming years. Research is ongoing to develop more eco-friendly and sustainable production methods. There is also scope to produce DDDA from renewable biomass feedstocks such as vegetable oils, which could provide an alternative to petrochemical routes. DDDA esters hold promise for next-gen lubricants with enhanced properties. Overall, DDDA will likely remain an important industrial platform chemical due to the versatility and performance benefits it affords to different end-use sectors. Continued innovation can further tap its full potential.
