Dodecanedioic acid, also known as DDDA or 1,12-dicarboxylic acid, is an organic compound with the formula HOOC(CH2)10COOH. It is a white solid that is soluble in common organic solvents. DDDA contains a twelve carbon chain terminated with carboxyl functional groups on both ends, making it a dialkyl carboxylic acid.
Chemical Properties and Structure
DDDA has a linear symmetrical structure with two carboxyl groups located at positions 1 and 12 of the alkyl chain. The carbon chain has the formula (CH2)10, giving DDDA a molecular formula of C12H22O4 and molecular weight of 226.31 g/mol. As an α,ω-dicarboxylic acid, DDDA has multiple reactive sites and can undergo a variety of chemical reactions. For example, the carboxyl groups can engage in esterification, amidation, or acid chloride formation reactions. The methylene groups in the carbon chain are also susceptible to halogenation, oxidation, and reduction reactions. DDDA has a melting point around 70°C and is soluble in organic solvents such as acetone, chloroform, and tetrahydrofuran due to its non-polar alkyl chain.
Industrial Production of DDDA
Virtually all DDDA produced commercially is synthesized via oxidation of 1,12-dodecanediol. This is achieved using catalysts such as chromic acid, potassium permanganate, or peroxides under controlled reaction conditions. 1,12-dodecanediol can be obtained through the hydroboration-oxidation of 1-dodecene or via oxo process from linear 1-alcohols. The oxidation of 1,12-dodecanediol yields DDDA in high selectivity, making this a practical and scalable industrial route. Global production capacity for DDDA is currently estimated to be over 100,000 metric tons per year. Major producers include BASF, Invista, Verdezyne, and Evonik.
Applications of DDDA in Resins and Plastics
As a component in various polymers, Dodecanedioic Acid sees widespread use in industrial and consumer applications. One of its primary uses is in the production of polyamide resins, more commonly known as nylons. DDDA serves as a monomer that polymerizes to form polyamide 12 (PA 12 or nylon 12) when reacted with diamines such as dodecanediamine. Nylon 12 exhibits useful properties such as resilience, low moisture absorption, and chemical resistance. It finds use in automotive, electrical/electronic, and mechanical engineering parts. DDDA is also employed to synthesize polyesters through polycondensation with diols. Polybutylene adipate terephthalate (PBAT) is one example of a bio-based and compostable polyester incorporating DDDA.
Use of DDDA in Other Applications
In addition to polymers, DDDA has applications in lubricants, surfactants, plasticizers, and corrosion inhibitors due to its linear structure. It is used as an intermediate to produce certain oleochemicals by combining the ω-acid group with long chain alcohols or amines. Esters of DDDA find use as plasticizers in PVC and other plastics for their resistance to migration. Other uses of DDDA include ion exchange resins, oil additives, diesel additives, and N-acyl amino acid paint driers. There is also increasing interest in using it as a building block for green materials, such as polyamide 11 (PA 11) for 3D printing filaments. Research continues on utilizing DDDA to synthesize novel materials for various end use markets.
Market for Dodecanedioic Acid
Market research analysts project ongoing demand growth for DDDA driven by its diverse polymer and chemical applications. Major factors influencing the DDDA market include increased polyamide and polyester production, especially in China, Southeast Asia, and the Middle East regions. Usage of nylon 12 in automotive, electronic, and industrial applications promotes higher volumes of DDDA. The bio-based plastics segment is another avenue contributing to market expansion. However, availability of substitute polyamides and limited monomer production capacity present challenges. Industry participants are investing to develop new production technologies and end products based on DDDA to capitalize on market potential over the long term. Overall the specialized chemical properties and technical performance advantages conferred by DDDA ensure its ongoing commercial importance in manufacturing.
In summary, dodecanedioic acid is an important industrial chemical intermediate with extensive applications as a monomer in polymers, synthetic lubricants, plasticizers, and other industrial materials. Mass commercial production is achieved by oxidation of 1,12-dodecanediol. DDDA plays a key role in nylon 12 and other polyamides, which see growing usage particularly in the automotive industry. Continued growth in demand for plastics and chemicals will support rising production and utilization of DDDA worldwide.
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