13048-33-4

Basic information

• Product Name: Hexamethylene diacrylate
• Synonyms: HDODA;HEXAMETHYLENE GLYCOL DIACRYLATE;1,6-BIS(ACRYLOYLOXY)HEXANE;1,6-HEXANEDIOL DIACRYLATE;1,6-HEXAMETHYLENE DIACRYLATE;1,6-hexanedioldi-2-propenoate;2-Propenoicacid,1,6-hexanediylester;acrylicacid,hexamethyleneester
• CAS NO: 13048-33-4
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.27
• EINECS: 235-921-9
• Product Categories: Industrial/Fine Chemicals;monomer;Diacrylates & Dimethacrylates;Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 13048-33-4.mol

Chemical Properties

• Melting Point: 6°C
• Boiling Point: 295°C
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.01 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chlroform (Slightly), DMSO (Slightly)
• Water Solubility: Slightly miscible with water.
• Sensitive: Hygroscopic
• Stability: Light Sensitive
• CAS DataBase Reference: Hexamethylene diacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Hexamethylene diacrylate(13048-33-4)
• EPA Substance Registry System: Hexamethylene diacrylate(13048-33-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-43
• Safety Statements: 39
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: AT1430000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 13048-33-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Hexamethylene diacrylate is used as a common acrylic monomer in organic synthesis, particularly for the production of UV-cured inks, adhesives, coatings, photoresists, castings, artificial nails, and dental composite materials.
Used in UV and EB Applications:
Hexamethylene diacrylate is used as a reactive component in formulating coatings and inks for ultra violet (UV) and electron beam (EB) applications. It is also used in furniture and floor coatings, coatings on plastic substrates, and varnishes for packing items.
Used in Cross-Linking Polymers:
Hexamethylene diacrylate acts as a cross-linking agent between the molecular chains of polymers, which enhances their adhesion, hardness, abrasion, and heat resistance. It is used in adhesives, sealants, alkyd coatings, elastomers, photopolymers, and inks.
Used in Solid Phase Synthesis of Hydrophobic Peptides:
The hexamethylene diacrylate cross-linked polystyrene resin can be used for the solid phase synthesis of hydrophobic peptides, which has applications in the pharmaceutical and biotechnology industries.

Sources

https://www.ashland.com/file_source/Ashland/Documents/Sustainability/rc_hexanediol_diacrylate.pdf Varkey, J. T., and V. N. Pillai. "Solid phase synthesis of hydrophobic peptides on 1,6-hexanediol diacrylate cross-linked polystyrene resin." Journal of Peptide Science 5.12(1999): 577-81. https://www.palmerholland.com/Assets/User/Documents/Product/40781/4988/MITM00481.pdf

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Hexamethylene diacrylate is temperature sensitive . May react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release gaseous hydrogen. Can undergo very exothermic addition polymerization reactions. May undergo autoxidation upon exposure to the air to form explosive peroxides.

Fire Hazard

Hexamethylene diacrylate is probably combustible.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H16O4/c1-3-11(13)15-9-7-5-6-8-10-16-12(14)4-2/h3-4,7,9H,1-2,5-6,8,10H2

Upstream product

• 629-11-8 1,6-hexanediol 
• 292638-85-8 acrylic acid methyl ester 
• 79-10-7 acrylic acid 
• 814-68-6 acryloyl chloride 
• 53219-91-3 3-Bromo-propionic acid 6-(3-bromo-propionyloxy)-hexyl ester 

Downstream Products

• 1369558-74-6 5-phenyl-pent-4-ynoic acid 6-(5-phenyl-pent-4-ynoyloxy)-hexyl ester 
• 1369558-75-7 5-(2-methylphenyl)-pent-4-ynoic acid 6-(5-(2-methylphenyl)-pent-4-ynoyloxy)-hexyl ester 
• 1337537-16-2 hexane-1,6-diol di-(3-[-methyl-N-phenylamino]propionate) 
• 145487-98-5 2-Acetoxy-3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 6-{2-acetoxy-3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-hexyl ester 
• 145487-82-7 3-[(R)-6,7-Dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-hydroxy-propionic acid 6-{3-[(R)-6,7-dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-hydroxy-propionyloxy}-hexyl ester 
• 145487-82-7 3-[6,7-Dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-hydroxy-propionic acid 6-{3-[6,7-dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-hydroxy-propionyloxy}-hexyl ester 
• 145487-81-6 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-hydroxy-propionic acid 6-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-hydroxy-propionyloxy}-hexyl ester 
• 145520-28-1 2-Acetoxy-3-[6,7-dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 6-{2-acetoxy-3-[6,7-dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-hexyl ester 
• 145520-27-0 3-[6,7-Dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-formyloxy-propionic acid 6-{3-[6,7-dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-formyloxy-propionyloxy}-hexyl ester 
• 173677-05-9 Acrylic acid 6-{3-[(R)-1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-hexyl ester 
• 81182-08-3 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 6-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-hexyl ester; compound with oxalic acid 

Relevant articles and documents

Bioreducible poly (β-amino esters)/shRNA complex nanoparticles for efficient RNA delivery

RNA interference (RNAi) mediating gene silencing is a promising approach in the area of gene therapy, but it still is a major challenge to find new non-viral vectors with high transfection efficiency and low toxicity until today. In this work, three novel bioreducible poly (β-amine esters) (PAEs) with different amino monomers in the main chain were designed and synthesized by Michael addition polymerization. All PAEs could condense shRNA into complex nanoparticles with particle size (60-200 nm) and positive surface charges (>+10 mV). The PAEs/shRNA complex nanoparticles (PAENs) were stable under the extracellular physiological condition, while it would degrade in the reductive environment due to the cleavage of the disulfide bonds in the PAEs main chain. PAENs could achieve efficient cellular uptake and EGFP silencing in HEK-293 cells and U-87 MG cells with low cytotoxicity. The high accumulation of PAENs in tumor and high silencing efficiency of intra-tumor EGFP expression occurred when PAENs were intravenously injected into BALB/c mice bearing U-87 MG-GFP tumor. The relationship between the polymer structure and RNAi efficiency and cytotoxicity showed that the density of nitrogen atoms in PAEs backbone and the existence of disulfide bonds demonstrated the remarkable influence on in vitro and in vivo gene silencing efficiency and cytotoxicity. These experimental results suggested that the PAENs could be a promising non-viral vector for efficient RNA delivery.

A new solid acid SO42?/TiO2 catalyst modified with tin to synthesize 1,6-hexanediol diacrylate

A new solid acid catalyst, SO42?/TiO2 modified with tin, was prepared using a sol-gel method and its physicochemical properties were revealed by nitrogen adsorption-desorption, X-ray powder diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, infrared spectroscopy of adsorbed pyridine, temperature-programmed desorption of ammonia and thermal gravimetric analysis. The structure, acidity and thermal stability of the SO42?/TiO2-SnO2 catalyst were studied. Incorporating tin enlarged the specific surface area and decreased crystallite size of the SO42?/TiO2 catalyst. The total acid sites of the modified catalyst increased and Br?nsted acid strength remarkably increased with increasing tin content. The decomposition temperature of sulfate radical in the modified catalyst was 100 °C greater and its mass loss was more than twice that of the SO42?/TiO2 catalyst. The SO42?/TiO2-SnO2 catalyst was designed to synthesize 1,6-hexanediol diacrylate by esterification of 1,6-hexanediol with crylic acid. The yield of 1,6-hexanediol diacrylate exceeded 87% under the optimal reaction conditions: crylic acid to 1,6-hexanediol molar ratio = 3.5, catalyst loading = 7%, reaction temperature = 130 °C and reaction time = 3 h. The modified catalyst exhibited excellent reusability and after 10 cycles the conversion of 1,6-hexanediol was above 81%.

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Preparation method of dihydric alcohol unsaturated carboxylate

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BIOABSORBABLE ELASTOMERIC POLYMER NETWORKS, CROSS-LINKERS AND METHODS OF USE

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A polymer electrolyte-forming composition containing (A) a quaternary ammonium salt of general formula (1) below and (B) an ionic liquid can be converted into a polymer without compromising the excellent properties of the ionic liquid, thus enabling an electrolyte having an excellent safety and electrical conductivity and also a broad potential window to be obtained. In formula (1), R1 to R3 are each independently an alkyl group of 1 to 5 carbons or a substituent having a reactive unsaturated bond and any two from among R1 to R3 may together form a ring, and R4 is methyl, ethyl or a substituent having a reactive unsaturated bond, with the proviso that at least one of R1 to R4 is a substituent having a reactive unsaturated bond. X is a monovalent anion, the letter m is an integer from 1 to 8, and the letter n is an integer from 1 to 4.

Liquid oligomers containing acrylate unsaturation

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