1,12-Dodecanediol dimethacrylate
[CAS# 72829-09-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 1,12-Dodecanediol dimethacrylate
• Synonyms: 1,12-Dodecamethylene dimethacrylate; 1,12-Dodecanediyl dimethacrylate; 2-Methyl-2-propenoic acid 1,1'-(1,12-dodecanediyl) ester
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.48
• CAS Registry Number: 72829-09-5
• EC Number: 276-900-4
• SMILES: CC(=C)C(=O)OCCCCCCCCCCCCOC(=O)C(=C)C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 415.7±18.0 °C 760 mmHg (Calc.)^*
• Flash point: 194.7±19.6 °C (Calc.)^*
• Index of refraction: 1.46 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H317-H319-H335-H400-H410
• Safety Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

1,12-Dodecanediol dimethacrylate is a bifunctional diester compound derived from the esterification of 1,12-dodecanediol with methacrylic acid or its derivatives. Its molecular formula is C₂₄H₃₈O₄. This molecule features two methacrylate groups attached at both ends of a twelve-carbon alkyl chain, making it a valuable monomer and cross-linking agent in polymer chemistry and materials science.

The synthesis of 1,12-dodecanediol dimethacrylate is commonly carried out by reacting 1,12-dodecanediol with methacrylic acid or methacryloyl chloride in the presence of catalysts or bases such as triethylamine to neutralize byproducts. The reaction is conducted under anhydrous conditions with temperature control and often includes polymerization inhibitors to prevent premature curing.

Owing to its two methacrylate polymerizable groups, 1,12-dodecanediol dimethacrylate acts as an effective cross-linker in free radical polymerizations. It is widely used in the formulation of thermosetting resins, coatings, adhesives, dental materials, and photo-curable systems. The twelve-carbon flexible spacer provides enhanced toughness, elasticity, and hydrophobicity to the polymer networks, which influence mechanical strength, flexibility, and chemical resistance.

In dental and biomedical applications, this compound improves the performance of composite materials by increasing cross-link density, reducing shrinkage upon polymerization, and enhancing biocompatibility. Its use leads to durable restorative materials with good mechanical properties and chemical stability.

Industrial applications include coatings and adhesives where it imparts improved impact resistance, flexibility, and weatherability. The longer alkyl chain compared to shorter diesters contributes to increased polymer chain mobility, balancing hardness with toughness.

Physically, 1,12-dodecanediol dimethacrylate is typically a clear, colorless to pale yellow viscous liquid. It is soluble in various organic solvents but sensitive to light, heat, and radical initiators. To maintain stability, it is stored under inert atmosphere with stabilizers such as hydroquinone derivatives to inhibit premature polymerization.

Handling requires proper precautions due to its potential to cause skin irritation and sensitization. Use of protective equipment and controlled processing environments is advised.

In summary, 1,12-dodecanediol dimethacrylate is a bifunctional methacrylate ester with a twelve-carbon spacer widely utilized as a cross-linking monomer in polymer science. Its chemical properties enable the production of flexible, durable, and high-performance polymers for dental, biomedical, and industrial applications.

References

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2021. Polyethylene glycol fumarate/acrylated-silica nanocomposite: synthesis, characterization and in-vitro evaluation. Journal of Polymer Research, 28(1).
DOI: 10.1007/s10965-020-02399-5

2018. Influence of a hydrophobic monomer on the physical and mechanical properties of experimental surface sealants. Brazilian Oral Research, 32(10).
DOI: 10.1590/1807-3107bor-2018.vol32.0108