DODECANEDIOIC ACID

Dodecanedioic Acid is a long-chain dicarboxylic acid used as a versatile polymer intermediate.
Dodecanedioic Acid provides flexibility, durability and moisture resistance to selected materials.
Polyamides, polyesters, coatings, adhesives and lubricant additives widely use Dodecanedioic Acid.

CAS Number: 693-23-2
EC Number: 211-746-3
Molecular Formula: C₁₂H₂₂O₄
Molecular Weight: 230.30 g/mol
MDL Number: MFCD00002735

Synonyms: DDDA, DC12, 1,12-Dodecanedioic acid, 1,10-Decanedicarboxylic acid, Decamethylenedicarboxylic acid, 1,10-Dicarboxydecane, n-Dodecanedioic acid, n-Dodecane-α,ω-dioic acid, 1,10-Decanedicarboxylate, Decane-1,10-dicarboxylic acid, Dodecanedioate, Corfree M2, Luna-mer DDA, C12 dibasic acid, SL-AH, NSC-400242, NSC 400242, CHEBI:4676, MFCD00002735, DTXSID3027297, UNII 978YU42Q6I, HSDB 5745, EC 211-746-3, CAS 693-23-2

Dodecanedioic Acid has the molecular formula C₁₂H₂₂O₄ and a molar mass of approximately 230.30 g/mol.
The structure of Dodecanedioic Acid contains two terminal carboxylic acid groups connected by a ten-carbon methylene chain.

Dodecanedioic Acid belongs to the family of long-chain alpha,omega-dicarboxylic acids.
The two reactive terminal groups make Dodecanedioic Acid a valuable bifunctional building block.

Dodecanedioic Acid normally appears as a white or off-white crystalline solid.
The long hydrocarbon section gives Dodecanedioic Acid both hydrophobic and reactive characteristics.

Water dissolves only a very small amount of Dodecanedioic Acid.
Alcohols and other suitable organic solvents dissolve Dodecanedioic Acid more effectively when heated.

Dodecanedioic Acid melts at approximately 128–131°C.
The low volatility of Dodecanedioic Acid supports its use in high-temperature synthesis processes.

Manufacturers can produce Dodecanedioic Acid through the controlled oxidation of suitable C₁₂ raw materials.
Purification and crystallization provide Dodecanedioic Acid with controlled color and chemical purity.

Polyamide manufacturers use Dodecanedioic Acid as a difunctional monomer.
The reaction of Dodecanedioic Acid with diamines produces long-chain polyamide structures.

Nylon 6,12 production uses Dodecanedioic Acid together with hexamethylenediamine.
Polyamides prepared from Dodecanedioic Acid can provide strength, flexibility and reduced moisture absorption.

Polyester synthesis can combine Dodecanedioic Acid with suitable diols or polyols.
The long aliphatic chain of Dodecanedioic Acid can improve the flexibility of polyester materials.

Coating resins may incorporate Dodecanedioic Acid to balance hardness and flexibility.
Dodecanedioic Acid can contribute to chemical resistance and surface durability in selected coatings.

Powder-coating systems can use Dodecanedioic Acid as a curing component or resin intermediate.
The two carboxylic groups of Dodecanedioic Acid support crosslinking reactions in suitable formulations.

Adhesive manufacturers use Dodecanedioic Acid in the preparation of polyester and polyamide resins.
Resins containing Dodecanedioic Acid can provide durable adhesion and flexible bonding.

Dodecanedioic Acid can undergo esterification with monoalcohols and polyols.
Esters derived from Dodecanedioic Acid find use in lubricants, plasticizers and specialty fluids.

Lubricant formulations may employ Dodecanedioic Acid derivatives to improve film formation and thermal performance.
The bifunctional structure of Dodecanedioic Acid enables the production of multifunctional lubricant additives.

Corrosion-control formulations can use salts and derivatives prepared from Dodecanedioic Acid.
Dodecanedioic Acid derivatives may support the formation of protective films on metal surfaces.

Organic synthesis uses Dodecanedioic Acid as a linear twelve-carbon building block.
Dodecanedioic Acid can be converted into esters, amides, salts and acid chlorides.

Reaction temperature, catalyst selection and moisture content influence polymerization involving Dodecanedioic Acid.
Careful process control helps Dodecanedioic Acid provide consistent conversion and material properties.

Acid value, melting range, water content and color represent important quality parameters for Dodecanedioic Acid.
Chromatographic and spectroscopic methods can confirm the identity and purity of Dodecanedioic Acid.

A white solid with a slight odour and a 12-carbon straight chain flanked by two carboxylic acid termini, dodecanedioic acid occupies a distinctive position among the long-chain aliphatic dicarboxylic acids — longer and more hydrophobic than adipic (C6) or sebacic (C10) acid, yet still bifunctional enough to serve as a versatile difunctional monomer and chemical building block across polymer, lubricant, coating, and fragrance chemistry. The 10-methylene spacer between its terminal –COOH groups confers the low water absorption, high flexibility, and excellent low-temperature properties that make dodecanedioic acid–derived polyamides and polyesters the preferred engineering plastics where adipic-acid-derived Nylon 66 or sebacic-acid-derived alternatives fall short in hydrolytic stability or cold-climate performance.

Uses of Dodecanedioic Acid:
Dodecanedioic acid is used as the dicarboxylic acid monomer for the industrial synthesis of high-performance long-chain engineering polyamides — PA612 (Nylon 6,12: hexamethylenediamine + dodecanedioic acid), PA1212 (Nylon 12,12: 1,12-dodecanediamine + dodecanedioic acid), and PA1012 (Nylon 10,12: 1,10-decanediamine + dodecanedioic acid) — which are valued for automotive underhood components, fuel-line tubing, brake tubing, flexible cable sheaths, aerospace structural components, electronic connectors, precision gears, and monofilament fibres due to their combination of toughness, wear resistance, chemical resistance, dimensional stability, and low moisture uptake relative to short-chain polyamides such as PA6 and PA66.
Dodecanedioic acid is used as the diacid component for the synthesis of long-chain aliphatic polyesters (ALCPE) for biodegradable plastics, hot-melt adhesives, polymer modifiers, and elastic fibres; as a modifier for saturated polyesters used in powder coatings and coil coatings (replacing shorter-chain diacids to improve flexibility, outdoor weatherability, and substrate adhesion of thermoset polyester powder coating binders crosslinked with TGIC or HAA/β-hydroxyalkylamide hardeners); and as a building block for specialty polyurethane elastomers and prepolymers with improved hydrolysis resistance and low-temperature flexibility.
Dodecanedioic acid is used as the diacid starting material for the synthesis of synthetic ester-based lubricants and plasticisers by direct esterification with monohydric or polyhydric alcohols: diesters with 2-ethylhexanol (dioctyl dodecanedioate) and octanol (dioctyl sebacate-equivalent) are used as high-grade lubricants for jet engines and gas turbines, as base oils for low-temperature greases, as high-viscosity-index synthetic ester lubricants for precision machinery and automotive engine oils, and as non-phthalate plasticisers for PVC, nitrocellulose, and cellulose acetate providing superior low-temperature flexibility and lower volatility than adipate or sebacate diesters.
Dodecanedioic acid is used as the key raw material for powder coating polyester resins: polyesters based on dodecanedioic acid and neopentyl glycol (NPG/DDDA polyesters) are crosslinked with TGIC (triglycidyl isocyanurate) or HAA (β-hydroxyalkylamide) curatives to produce smooth, glossy, flexible, outdoor-durable thermosetting powder coatings for architectural aluminium profiles, appliance panels, and automotive parts; DDDA replaces isophthalic acid or adipic acid in portions of the polyester backbone to improve film flexibility, impact resistance, and corrosion protection.
Dodecanedioic acid is used in the synthesis of structural adhesives and hot-melt adhesives for bonding metal, plastic, and composite substrates; in the formulation of high-solid, low-VOC coatings and anti-corrosion primers; as a corrosion inhibitor precursor and chemical reaction regulator in lubricant additive packages; as a capacitor electrolyte component; and as a metal precipitation agent in analytical chemistry and metallurgical processes.
Dodecanedioic acid is used as a chemical intermediate in the synthesis of aroma chemicals and synthetic fragrances (musks, macrocyclic fragrance compounds); in the production of biodegradable surfactants (amino acid–based and polyol-based surfactants from DDDA); in pharmaceutical intermediate synthesis; and in textile auxiliaries (fabric conditioner and softener formulations) where it functions as a softening and conditioning agent and flow promoter per EPA functional classification.

Benefits and Advantages of Dodecanedioic Acid:
Dodecanedioic acid provides an optimal combination of chain length, bifunctionality, and physical properties among commercially available dicarboxylic acids: its 10-methylene chain is long enough to impart low moisture absorption, high flexibility, excellent low-temperature performance (glass transition temperature depression), and resistance to hydrolysis, yet short enough to maintain the high melting point and dimensional stability demanded in engineering polyamide applications; these properties are not achievable with adipic acid (C6, too hydrophilic) or sebacic acid (C10, lower melting point and yield from limited castor oil supply), making dodecanedioic acid the preferred choice for premium polyamide engineering plastics demanding the best balance of mechanical, thermal, and environmental performance.
The esterification chemistry of dodecanedioic acid with both aliphatic and aromatic alcohols and polyols proceeds readily under standard acid-catalysed or enzymatic conditions, producing a wide range of esters from low-viscosity diester lubricants to high-MW polyester resins; this versatility across ester chemistry, combined with the physical property advantage of the C12 backbone over shorter acids, makes dodecanedioic acid a uniquely enabling raw material across synthetic lubricants, plasticisers, powder coating resins, and biodegradable polymer applications within a single compound class.
Dodecanedioic acid is increasingly produced via bio-fermentation (Candida tropicalis, Candida viswanathii) from vegetable oils (palm kernel oil, coconut oil, vernonia galamensis oil) and long-chain alkanes, providing a bio-based, renewable supply pathway that complements traditional chemical synthesis; bio-based dodecanedioic acid reduces dependence on petroleum-derived butadiene and enables formulators and polymer producers to access sustainable, bio-sourced raw materials for "green" polymer and lubricant applications.

Features of Dodecanedioic Acid:
Dodecanedioic acid is a white crystalline solid at room temperature, available as powder, flakes, or pellets, with a slight characteristic odour; melting point 127–129°C; boiling point 245°C (atmospheric); density 1.066 g/cm³; water solubility pH-dependent — very low at neutral pH, increasing markedly with pH as the dicarboxylate dianion forms (relevant to aqueous formulation processing); essentially non-volatile under ambient conditions (negligible vapour pressure); solubility in common organic solvents: soluble in alcohols (ethanol, methanol), ketones (acetone), and DMSO; slightly soluble or sparingly soluble in ethyl acetate; practically insoluble in non-polar hydrocarbons (hexane, toluene); SMILES OC(=O)CCCCCCCCCCC(O)=O; InChIKey TVIDDXQYHWJXFK-UHFFFAOYSA-N.
Commercial specification (typical): appearance — white powder or flakes; dodecanedioic acid content ≥98.0%; total acid ≥99.0%; moisture ≤0.5%; ash ≤30 ppm; iron ≤3 ppm; total nitrogen ≤50 ppm; melting point 128–131°C.
Dodecanedioic acid is the most commercially important and widely encountered of the C12 dicarboxylic acid homologues; it is the longest commercially available aliphatic straight-chain dicarboxylic acid produced in significant volume; homologues (C11, C13, C14+) and biosynthetically related metabolites are extremely difficult to separate from aqueous solution due to poor aqueous solubility and tendency to uncontrolled crystallisation; DDDA crystallises in a fully extended zig-zag chain conformation typical of even-numbered long-chain dicarboxylic acids; powder X-ray diffraction characterisation is available in the literature.

Chemical Properties of Dodecanedioic Acid:
Dodecanedioic acid has IUPAC name dodecanedioic acid (systematic IUPAC: dodecanedioic acid), CAS 693-23-2, molecular formula C₁₂H₂₂O₄, molecular weight 230.30 g/mol, SMILES OC(=O)CCCCCCCCCCC(O)=O, InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16), InChIKey TVIDDXQYHWJXFK-UHFFFAOYSA-N; EC 211-746-3; MDL MFCD00002735; PubChem CID 12736; ChEBI CHEBI:4676; UNII 978YU42Q6I; DTXSID3027297; KEGG C02678.
Key chemical reactions of dodecanedioic acid: (1) polyamide synthesis — polycondensation with diamines (hexamethylenediamine, 1,10-decanediamine, 1,12-dodecanediamine) to give PA612, PA1012, PA1212; (2) polyester synthesis — polycondensation with diols (neopentyl glycol, ethylene glycol, 1,4-butanediol) to give long-chain aliphatic polyesters and powder coating polyesters; (3) direct esterification with monohydric alcohols (octanol, 2-ethylhexanol, butanol) → diester lubricants and plasticisers, acid-catalysed at 140–200°C; (4) salt formation with alkali metal hydroxides or amines → sodium dodecanedioate, ammonium salts used in corrosion inhibitor formulations; (5) reduction → 1,12-dodecanediol; (6) decarboxylation at high temperature; (7) reaction with boric acid in autoxidation context (historical production route intermediate step); (8) bio-oxidation of dodecane by fungal peroxygenases (Candida spp.) → DDDA (bio-fermentation route).
Dodecanedioic acid is chemically stable under normal ambient conditions; it is a moderately strong dicarboxylic acid (both pKa values in the carboxylic acid range, approximately 4.0–5.5) and therefore mildly acidic in aqueous solution; it undergoes the typical reactions of aliphatic dicarboxylic acids — esterification, amidation, salt formation, and reduction; it is stable to hydrolysis under ambient conditions; it is incompatible with strong oxidising agents (risk of exothermic reaction or ignition), strong bases at elevated temperature (rapid saponification), and reactive amines at elevated temperature (amide bond formation).

Production of Dodecanedioic Acid:
Dodecanedioic acid is produced industrially by two major commercial routes: (1) chemical synthesis from butadiene: butadiene is cyclotrimerised to cyclododecatriene (CDT) using a Ziegler-type catalyst; CDT is fully hydrogenated to cyclododecane (CDAN); CDAN is autoxidised by air in the presence of boric acid to a mixture of cyclododecanol (CDOL) and cyclododecanone (CDON); CDOL/CDON mixture is oxidised with concentrated nitric acid (HNO₃) at elevated temperature to yield dodecanedioic acid; the crude product is purified by recrystallisation and/or distillation; (2) bio-fermentation route: long-chain alkanes (C12, dodecane) or vegetable oils (palm kernel oil, coconut oil, vernonia galamensis oil) are oxidised by specialised Candida tropicalis or Candida viswanathii yeast strains via ω-oxidation (cytochrome P450-mediated terminal oxidation) to give dodecanedioic acid; this bio-based route is increasingly used and provides a renewable, bio-sourced supply of DDDA competitive with the chemical route in quality and purity.
Alternative laboratory production routes include: ozonolysis of cyclododecene (→ DDDA directly); oxidation of cyclododecanol with HNO₃ in the laboratory (standard small-scale preparation); and biomimetic oxidation using fungal peroxygenases.
Commercial dodecanedioic acid is available in: standard industrial grade (≥98.0%, white powder or flakes, 25 kg woven-plastic bags with PE liner; 500 kg or 1,000 kg FIBC bags; bulk); refined/high-purity grade (≥99.0%); pharmaceutical/research grade (≥99.0–99.5%); packaging: 25 kg net weight per woven-plastic bag lined with PE bag (moisture-proof and dust-proof); 500 kg or 1,000 kg FIBC (super sack) for bulk orders; storage: cool, dry, well-ventilated warehouse, away from direct sunlight, heat sources, strong oxidisers, and strong bases; shelf life 24 months under recommended storage conditions.

Dodecanedioic Acid Material Safety Data Sheet (MSDS):

Handling of Dodecanedioic Acid:
Dodecanedioic acid is a low-to-moderate hazard solid material; standard industrial hygiene practices apply: avoid generating and inhaling dust (potential respiratory irritant at elevated dust concentrations); wear dust mask or respirator, safety glasses, and gloves for powder handling; the material is a combustible solid — keep away from open flames and strong oxidising agents; avoid prolonged skin and eye contact; wash hands after handling.
At temperatures above its melting point (127–129°C), dodecanedioic acid forms a low-viscosity melt; molten material presents a thermal burn hazard; use appropriate PPE and local exhaust ventilation for hot-melt processing.

Dodecanedioic Acid SDS:

Stability and Reactivity of Dodecanedioic Acid:

Chemical stability:
Dodecanedioic acid is stable under normal ambient storage and handling conditions.
It is incompatible with strong oxidising agents (risk of fire or exothermic reaction), strong bases at elevated temperature (saponification), and concentrated reactive amines at elevated temperature (amide formation).

Reactivity:
Dodecanedioic acid is a mild dicarboxylic acid; it undergoes typical carboxylic acid reactions — esterification, amidation, and salt formation — under appropriate activation conditions (elevated temperature, catalyst, or activated intermediates).
It is a combustible solid — ignition is possible above flash point; dust-air mixtures may be explosible if finely divided.

Conditions to avoid:
Strong oxidising agents (permanganate, peroxides, concentrated HNO₃ at elevated temperature).
Open flames and ignition sources above melting/flash point.
Dust generation near ignition sources.

Incompatible materials:
Strong oxidising agents.
Strong inorganic bases at elevated temperature.
Concentrated reactive amines at elevated temperature (rapid amide formation — controlled in polyamide manufacture).

Hazardous decomposition products:
No hazardous decomposition products under normal ambient conditions.
At high temperatures: CO, CO₂, and low-MW carboxylic acid decomposition products.

Handling and Storage of Dodecanedioic Acid:

Handling:
Handle in a well-ventilated area; wear dust mask, safety glasses, and gloves.
Avoid dust generation; use local exhaust ventilation for powder handling operations.
Keep away from open flames, heat sources, and strong oxidising agents.
Wash hands after handling; do not eat, drink, or smoke during handling.

Storage:
Store in a cool, dry, well-ventilated warehouse, away from direct sunlight, heat sources, strong oxidisers, and strong bases.
Shelf life: 24 months under recommended storage conditions.
Packaging: 25 kg woven-plastic bags lined with PE bag (moisture-proof, dust-proof); 500 kg or 1,000 kg FIBC for bulk orders.

First Aid Measures for Dodecanedioic Acid:

Inhalation: Move to fresh air; if dust inhalation causes respiratory irritation, consult a physician.
Skin contact: Rinse with water; wash with soap and water; for molten material contact, cool immediately with water.
Eye contact: Rinse with plenty of water for at least 15 minutes; consult a physician if irritation persists.
Ingestion: Rinse mouth with water; seek medical advice.

Firefighting Measures for Dodecanedioic Acid:

Suitable extinguishing media: CO₂, dry chemical, foam, water spray.
Specific hazards: Combustible solid; dust may form explosive mixtures in air; combustion produces CO and CO₂.
Protective equipment for firefighters: SCBA and full protective clothing.

Accidental Release Measures for Dodecanedioic Acid:

Personal precautions: Wear dust mask, gloves, and safety glasses; prevent dust generation.
Environmental precautions: Low environmental hazard at typical spill quantities; prevent entry into waterways.
Clean-up: Collect by sweeping or vacuuming (wet method preferred to suppress dust); dispose per applicable regulations.

Exposure Controls / Personal Protective Equipment for Dodecanedioic Acid:

Engineering controls: Local exhaust ventilation for powder handling and hot-melt processing; general ventilation for ambient solid-state handling.
Eye protection: Safety glasses; splash goggles for hot-melt operations.
Hand protection: Nitrile or neoprene gloves; heat-resistant gloves for hot-melt.
Respiratory protection: Dust mask (P2) for powder handling.

Dodecanedioic Acid Identifiers:
CAS Number: 693-23-2
EC Number: 211-746-3
EINECS: 211-746-3
MDL Number: MFCD00002735
PubChem CID: 12736
ChEBI: CHEBI:4676
ChemSpider: 12213
UNII: 978YU42Q6I
KEGG: C02678
DTXSID: DTXSID3027297
ECHA InfoCard: 100.010.680
HSDB: 5745
IUPAC Name: Dodecanedioic acid
Molecular Formula: C₁₂H₂₂O₄
Molecular Weight: 230.30 g/mol
SMILES: OC(=O)CCCCCCCCCCC(O)=O
InChI: InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)
InChIKey: TVIDDXQYHWJXFK-UHFFFAOYSA-N
Melting point: 127–129°C (lit.)
Boiling point: 245°C (atmospheric)
Density: 1.066 g/cm³
Water solubility: pH-dependent; <0.1 g/L at neutral pH (20°C)
Appearance: White crystalline powder or flakes
Shelf life: 24 months (recommended storage)

Properties of Dodecanedioic Acid:
Physical state: Solid (crystalline)
Appearance: White crystalline powder or flakes; slight odour
Molecular formula: C₁₂H₂₂O₄
Molecular weight: 230.30 g/mol
Melting point: 127–129°C
Boiling point: 245°C
Density: 1.066 g/cm³
Water solubility: pH-dependent; <0.1 g/L at neutral pH
Vapour pressure: Negligible (ambient temperature)
Solubility in organics: Ethanol, methanol, acetone, DMSO; sparingly in ethyl acetate; practically insoluble in hexane/toluene
Storage: Cool, dry, ventilated; away from oxidants, bases, and heat; tightly closed

Dodecanedioic Acid Properties — Specifications:
Product name: Dodecanedioic acid (DDDA, DC12)
CAS Number: 693-23-2
EC Number: 211-746-3
Molecular Formula: C₁₂H₂₂O₄
Molecular Weight: 230.30 g/mol
Appearance: White powder or flakes
Dodecanedioic acid content: ≥98.0%
Total acid: ≥99.0%
Moisture: ≤0.5%
Ash: ≤30 ppm
Iron: ≤3 ppm
Total nitrogen: ≤50 ppm
Melting point: 128–131°C
Packaging: 25 kg woven-plastic bag (PE-lined); 500/1,000 kg FIBC
Shelf life: 24 months (cool, dry, ventilated storage)
Documents: CoA, TDS, SDS

Names of Dodecanedioic Acid:
Dodecanedioic acid
DDDA
DC12
1,12-Dodecanedioic acid
1,10-Decanedicarboxylic acid
Decamethylenedicarboxylic acid
1,10-Dicarboxydecane
n-Dodecanedioic acid
n-Dodecane-α,ω-dioic acid
Decane-1,10-dicarboxylic acid
1,10-Decanedicarboxylate
Dodecanedioate
Corfree M2
Luna-mer DDA
C12 dibasic acid
SL-AH
NSC-400242
NSC 400242
MFCD00002735
CHEBI:4676
DTXSID3027297
UNII 978YU42Q6I
HSDB 5745
CAS 693-23-2
EC 211-746-3