Chemical properties and structure of Dodecanedioic Acid
Decamethylenedicarboxylic acid, also known as DDDA or 1,12-decamethylenedicarboxylic acid, is an organic compound classified as a dicarboxylic acid. Its chemical formula is C12H22O4 and molar mass is 230.30 g/mol. The structure of decamethylenedicarboxylic acid consists of a linear chain of 12 carbon atoms with carboxyl functional groups (-COOH) at both ends of the chain. This gives the molecule two acidic hydrogens which can dissociate in solution. Decamethylenedicarboxylic acid is a white, waxy solid with a high melting point of around 90°C. It has limited solubility in water but is soluble in organic solvents like alcohols, acetone and dichloromethane.
Uses and applications of Decamethylenedicarboxylic acid
Due to its chemical properties as a Dicarboxylic Acid, decamethylenedicarboxylic acid finds wide applications in chemical industry as a building block in the production of numerous materials and compounds. Some key uses and applications of decamethylenedicarboxylic acid include:
- Resins and polymers: DDDA is commonly used as a monomer (raw material subunit) in the production of various polyamide and polyester resins that are used to make plastics, textiles, fibers and coatings. Nylon-12, which is a lightweight engineering plastic, is created from the polymerization of decamethylenedicarboxylic acid.
- Lubricants and surfactants: The fatty acid-like structure of DDDA enables it to be esterified into emollients, lubricants and surfactants that are added to cosmetics, personal care products and industrial lubricants.
- Adhesives and sealants: Decamethylenedicarboxylic acid-derived polyamides and polyesters act as binders, adhesives and sealants in construction materials, coated papers and sealant formulations.
- Paints and coatings: These resins and polymers made from DDDA provide moisture resistance, toughness and durability to paint formulations used in architectural, automotive, industrial and marine applications.
- Metalworking fluids: Synthetic coolants and lubricants used in machining processes contain esters of decamethylenedicarboxylic acid to lubricate and cool metal surfaces under cutting forces.
Production methods for Decamethylenedicarboxylic acid
Currently, there are two primary industrial methods used for commercial production of decamethylenedicarboxylic acid:
- Hydrophosphorylation of 1-decene: In this bio-based process, 1-decene is reacted with phosphorus trichloride followed by oxidation and hydrolysis. The overall reaction involves the addition of a phosphorus-oxygen-hydrogen group across the C=C double bond of 1-decene forming an intermediate diol that is further oxidized to DDDA.
- Oxidation of 1,12-dodecanediol: An alternative petrochemical route involves oxidizing 1,12-dodecanediol (obtained from hydrogenation of dodecene) with oxygen in the presence of a metal catalyst like copper or manganese salts. The diol is converted to the diacid product decamethylenedicarboxylic acid through oxidation of the alcohol functional groups.
Both these production methods generally yield high purity decamethylenedicarboxylic acid (>98%) which can be further purified through recrystallization if needed for certain applications. While the bio-based method is considered more eco-friendly and sustainable, the petroleum-derived process is currently more economical at large scales. Continuous research aims to improve the efficiency and reduce costs of decamethylenedicarboxylic acid synthesis.
Health and environmental aspects
From a human and environmental health perspective, decamethylenedicarboxylic acid itself presents low acute toxicity risks upon ingestion or skin contact as per various toxicity studies. The LD50 oral dose in rats was found to be over 5000 mg/kg body weight. However, like most organic chemicals, it can cause mild skin and eye irritation in direct and prolonged contact with concentrated forms.
When processed or combusted at high temperatures, DDDA has the potential to decompose into hazardous gases like carbon oxides. Strict safety precautions must thus be followed during industrial manufacturing and formulation processes involving dodecanedioic acid. Once cured or reacted into finished products, it offers no known leaching or exposure risks under standard conditions of use. DDDA-derived polymers demonstrate effective resistance to degradation, making them suitable for numerous long-term applications.
Concerns around environmental pollution could potentially arise from uncontrolled spills or improper disposal of large quantities of purified decamethylenedicarboxylic acid into soils and water bodies where it may persist for long periods without breaking down significantly. Overall, with appropriate manufacturing waste handling and product end-of-life measures, the risks to human health and environment from this important industrial building block chemical can be effectively mitigated.
Considering its unique structural and reactive properties, decamethylenedicarboxylic acid is expected to remain a key platform chemical finding broad use well into the future. Researchers continue exploring novel bio-based and green synthetic pathways to produce DDDA more sustainably. New potential applications are also being developed leveraging its versatility as a monomer for advanced high-performance resins. Some emerging areas of focus could include biodegradable or recyclable polymers for 3D printing filaments, biomedical devices and environmentally-friendly coatings. With growing global demand for its end-use products, sustainable large-scale production of decamethylenedicarboxylic acid will play an important role.
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