1. Chemical Identity:
Name: Octadecanedioic acid
CAS Number: 871-70-5
Molecular Formula: C18H34O4
IUPAC Name: Octadecanedioic acid
Other names: 1,18-Octadecanedioic acid, C18 diacid
2. Physical and Chemical Properties:
Appearance: White crystalline solid
Molecular Weight: 314.46 g/mol
Melting Point: 123-124°C
Boiling Point: 250°C (at 4 mmHg)
Solubility: Slightly soluble in water, soluble in organic solvents
3. Applications
1) Polymer Production
Polyamides and polyesters are two distinct classes of polymers that are produced through different processes.
ODDA is a monomer that is widely utilized in the synthesis of high-performance polyamides and polyesters. The aliphatic chain of ODDA confers enhanced flexibility, resilience, and chemical and thermal resistance to the resulting polymers. The specific applications include:
Engineering plastics: The material is employed in the automotive, electrical, and electronics industries for the fabrication of components that are required to demonstrate durability and resistance to elevated temperatures.
Fibers: These polymers are employed in the production of textiles and industrial fabrics due to their combination of strength and elasticity.
Films: These materials are employed in the production of packaging and specialty films, where durability and barrier properties are of paramount importance.
The benefits of performance are as follows:
The material exhibits flexibility and toughness. The extended chain length endows the material with exemplary mechanical properties.
Chemical Resistance: The enhanced resistance to solvents and chemicals renders these polymers suitable for use in harsh environments.
Thermal stability is a property that allows polymers to withstand high temperatures without undergoing significant changes in their chemical composition or physical structure. The enhanced heat resistance of these materials allows for the expansion of their potential applications.
2) Lubricants and Greases
The incorporation of ODDA into the formulation of lubricants and greases is a crucial step in enhancing their performance characteristics.
Thermal stability is a property that enables a substance to withstand high temperatures without undergoing significant changes in its chemical composition or physical state. The incorporation of ODDA into lubricant formulations enhances the thermal stability of these materials, rendering them suitable for high-temperature applications.
Viscosity Index: It contributes to a stable viscosity over a wide temperature range, ensuring consistent performance.
Lubricity: Enhanced lubricity reduces friction and wear, extending the lifespan of mechanical components.
3) Cosmetics and Personal Care Products
ODDA is esteemed in the cosmetics and personal care industry for its emollient properties.
The process of moisturization is essential for maintaining optimal dermal health. It assists in the retention of dermal moisture, rendering it an efficacious component in the formulation of creams and lotions.
The softening effect is achieved by: It is employed in hair care products to impart softness and conditioning properties to the hair.
The stability of the product is ensured. It serves to enhance the stability and shelf life of formulations.
The following products are available:
In the domain of skincare, Moisturizers, anti-aging creams, and sunscreens are among the products that utilize this ingredient.
The product range also includes items designed for use on the hair. Conditioners, hair masks, and serums are also available.
The Personal Care product line includes: The product range includes lotions, body creams, and bath products.
4) Pharmaceuticals
In the pharmaceutical industry, the potential of ODDA in drug delivery systems is being investigated.
Formulations with Sustained Release: The biocompatibility and biodegradability of ODDA render it an appropriate material for the development of sustained-release drug formulations, which facilitate the controlled release of active ingredients.
Drug Carriers: It is employed as a carrier for active pharmaceutical ingredients (APIs) with the objective of enhancing their stability and bioavailability.
The potential applications of ODDA are numerous and diverse.
Oral Drug Delivery: Tablets and capsules with extended-release properties.
Topical Formulations: Topical formulations, such as creams and ointments, are employed for localized treatment.
Injectable Formulations: Biodegradable carriers for sustained-release injectables.
5) Corrosion Inhibitors
ODDA is employed as a corrosion inhibitor in a number of industrial sectors, serving to safeguard metal surfaces from the damaging effects of oxidation.
Metalworking Fluids: It is added to fluids used in cutting, grinding, and machining to safeguard both the tools and the workpieces.
Coatings: The incorporation of this compound into paints and coatings serves to prevent the corrosion of metal structures.
The benefits of the product in terms of performance are as follows:
The provision of protection is a key benefit of this product. It forms a protective layer on metal surfaces, inhibiting the processes of oxidation and corrosion.
The durability of the coating is contingent upon the following factors: It serves to extend the lifespan of metal components and structures.
The product is suitable for use in a number of different industries.
In the automotive industry, The application of protective coatings to vehicle components serves to safeguard these components from the detrimental effects of corrosion and oxidation.
In the construction industry, the use of these coatings can extend the lifespan of metal components and structures. Corrosion-resistant coatings for buildings and infrastructure.
The oil and gas industry requires protective coatings for a variety of components and equipment. The protection of pipelines and drilling equipment is of paramount importance in the oil and gas industry.
4. Synthesis
1) Chemical Synthesis:
a) Oxidation of Oleic Acid:
Substrate: Oleic acid (cis-9-octadecenoic acid)
Process:
a. Epoxidation of the double bond using hydrogen peroxide and formic acid.
b. Ring-opening of the epoxide to form a vicinal diol.
c. Oxidative cleavage of the diol using periodic acid or sodium periodate.
Catalysts: Various transition metal catalysts can be used to improve selectivity and yield.
Advantages: Well-established process, can use both bio-based and petrochemical oleic acid.
Challenges: Multiple steps, potential for side reactions.
b) Oxidation of Unsaturated Fatty Acids:
Similar to oleic acid oxidation but can use a mixture of unsaturated fatty acids.
Often requires a separation step to isolate octadecanedioic acid from other chain length diacids.
c) Carbonylation of 1,17-Octadecadiene:
Process:
a. Synthesis of 1,17-octadecadiene from petrochemical feedstocks.
b. Carbonylation using carbon monoxide and water in the presence of a catalyst.
Catalysts: Typically use palladium-based catalysts.
Advantages: Can achieve high selectivity.
Challenges: Requires high pressure and temperature, use of toxic carbon monoxide.
d) Electrochemical Synthesis:
Involves anodic oxidation of oleic acid or other C18 fatty acids.
Process occurs in an electrochemical cell with appropriate electrolytes and electrode materials.
Advantages: Potentially more environmentally friendly than chemical oxidation methods.
Challenges: Scale-up and process optimization.
2) Green Chemistry Approaches:
a) Photocatalytic Oxidation:
Uses sunlight or artificial light sources with appropriate photocatalysts.
Aims to perform selective oxidation under mild conditions.
Still largely in the research phase for long-chain diacids like octadecanedioic acid.
b) Enzymatic Synthesis:
Utilizes isolated enzymes or whole-cell biocatalysts for selective oxidation.
Can be combined with chemical steps in chemo-enzymatic processes.
Advantages: High selectivity, mild reaction conditions.
Challenges: Enzyme stability, cofactor regeneration, scale-up.
5. Comparison with Other Dicarboxylic Acids
1) Structural Comparison:
Octadecanedioic acid (C18H34O4) is a long-chain aliphatic dicarboxylic acid with 18 carbon atoms.
Common shorter-chain diacids include:
Succinic acid (C4H6O4)
Adipic acid (C6H10O4)
Suberic acid (C8H14O4)
Sebacic acid (C10H18O4)
Dodecanedioic acid (C12H22O4)
Longer-chain diacids like eicosanedioic acid (C20H38O4) are less common.
2) Physical Properties:
a) Melting Point:
Octadecanedioic acid: 123-124°C
Generally, melting points increase with chain length up to C10-C12, then plateau or slightly decrease:
Succinic acid: 185°C
Adipic acid: 152°C
Sebacic acid: 134°C
Dodecanedioic acid: 128-129°C
b) Solubility:
Water solubility decreases with increasing chain length.
Octadecanedioic acid is only slightly soluble in water but more soluble in organic solvents.
Shorter-chain diacids (e.g., succinic, adipic) have higher water solubility.
c) Volatility:
Decreases with increasing chain length.
Octadecanedioic acid has lower volatility compared to shorter-chain diacids.
3) Chemical Reactivity:
All dicarboxylic acids can undergo typical carboxylic acid reactions (esterification, amidation, etc.).
Longer chains like octadecanedioic acid:
Have reduced reactivity due to increased steric hindrance.
Show increased hydrophobicity, affecting reaction environments and catalysis.
4) Polymer Applications:
a) Polyesters:
Octadecanedioic acid produces polyesters with:
Lower melting points
Increased flexibility
Enhanced hydrophobicity
Shorter-chain diacids (e.g., adipic acid) yield more rigid, higher-melting polyesters.
b) Polyamides:
Octadecanedioic acid-based polyamides have:
Lower melting points
Improved low-temperature impact strength
Enhanced resistance to moisture absorption
Compared to nylon-6,6 (from adipic acid), which has higher crystallinity and melting point.
5) Biodegradability:
Generally, biodegradability decreases with increasing chain length.
Octadecanedioic acid biodegrades more slowly than shorter-chain diacids.
However, it’s still considered biodegradable, unlike some aromatic diacids.
Industrial Production:
Shorter-chain diacids (C4-C6) are primarily produced via petrochemical routes.
Mid-chain diacids (C8-C12) have both bio-based and petrochemical production methods.
Octadecanedioic acid is increasingly produced via biotechnological methods, distinguishing it from shorter-chain counterparts.
