4-Hydroxybutyl acrylate

• CAS: 2478-10-6
• Catalog Number: ACM2478106-1
• Category: Polymer/Macromolecule; Main Products
• Molecular Weight: 144.17
• Molecular Formula: H2C=CHCO2(CH2)4OH
• Description: 4-Hydroxybutyl acrylate (HBA) can be synthesized by the esterification of acrylic acid with 1, 4 butanediol over a catalyst such as Amberlyst 15. 4-Hydroxybutyl acrylate (HBA) exhibits properties such as luster, chemical and scratch resistance. HBA monomers may be used as one of the constituents for the fabrication of a membrane system for controlled release of transdermal drug delivery system.
• Synonyms: 1,4-Butanediolmonoacrylate;2-Propenoicacid,4-hydroxybutylester;4-Hydroxybutyl2-propenoate;4-HYDROXYBUTYL ACRYLATE;ACRYLIC ACID 4-HYDROXYBUTYL ESTER;BUTANEDIOL MONOACRYLATE;4-HYDROXYBUTYL ACRYLATE, 90% TECHNICAL GRADE;Tetramethylene glycol monoacrylate
• IUPAC Name: 4-hydroxybutyl prop-2-enoate
• SMILES: OCCCCOC(=O)C=C
• InChI: 1S/C7H12O3/c1-2-7(9)10-6-4-3-5-8/h2,8H,1,3-6H2
• InChI Key: NDWUBGAGUCISDV-UHFFFAOYSA-N
• Boiling Point: 95 °C/0.1 mmHg (lit.)
• Flash Point: 266°F (130°C)
• Density: 1.041 g/mL at 25 °C (lit.)
• Appearance: Colorless to brown liquid.
• Application: Hydroxybutyl acrylate was one of the monomers utilized in the preparation of poly(2-hydroxy-3-phenoxypropylacrylate, 4-hydroxybutyl acrylate, dibutyl maleate) membranes.
• Alpha Sort: Hydroxybutyl acrylate
• Assay: 90%
• Complexity: 109
• Contains: 300 ppm hydroquinone as inhibitor; 50 ppm monomethyl ether hydroquinone as inhibitor
• Covalently-Bonded Unit Count: 1
• EC Number: 219-606-3
• Exact Mass: 144.078644g/mol
• Features And Benefits: 1. High quality products; 2. Fast delivery; 3. Additional products can be ordered, please contact us for details
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Heavy Atom Count: 10
• Inhibitor: MEHQ
• MDL Number: MFCD00010261
• Monoisotopic Mass: 144.078644g/mol
• NACRES: NA.23
• Packaging: Packaging; 25 g in glass bottle
• PubChem ID: 24856656
• Quality Level: 100
• Refractive Index: n20/D 1.452 (lit.)
• Rotatable Bond Count: 6
• Storage Temperature: 2-8°C
• UNII: 4O2A4HET1X
• Viscosity: 20cp (25°C)
• XLogP3: 1.1

Case Study

4-Hydroxybutyl Acrylate as a Functional Monomer for High-Adhesion Gel Polymer Electrolytes in Lithium-Ion Batteries

Choi, Hui Ju, et al. Chemical Engineering Journal 474 (2023): 145673.

Gel polymer electrolytes (GPEs) offer a promising solution to enhance the safety and flexibility of lithium-ion batteries (LIBs). 4-Hydroxybutyl acrylate (HBA), a monomer known for its excellent adhesion properties in biomedical and underwater applications, was investigated as the backbone for crosslinked GPE networks in LIBs.
A systematic materials design was conducted by varying liquid electrolyte content (80-95 vol%) and monomer-to-crosslinker ratio (HBA:poly(ethylene glycol) diacrylate = 99:1 to 80:20), generating 16 GPE formulations. The resulting poly(4-hydroxybutyl acrylate) (PHBA) networks were characterized for gelation behavior, rheology, adhesion, electrochemical stability, and ionic conductivity.
Key Results:
· GPE formation was categorized into three regimes based on tanδ changes during photopolymerization: no gelation, viscous gel, and stable gel, enabling precise control over mechanical properties with storage modulus tunable from 0.92 kPa to 19.01 kPa.
· PHBA-based GPEs exhibited up to 10.92-fold higher lap shear strength compared to conventional ethylene oxide-based GPEs (carbitol acrylate), attributed to abundant hydrogen bonding from hydroxyl groups enhancing interfacial adhesion.
· All stable GPE formulations maintained ionic conductivity above 10^-3 S/cm at room temperature, with excellent electrochemical stability comparable to liquid electrolytes. In half-cell LIB testing (NCM811 cathode vs. Li metal), GPE8 delivered an initial discharge capacity of 212.37 mAh/g with 99.69% Coulombic efficiency, and retained 87.43% capacity under varied C-rates (0.1 C to 1 C).

4-Hydroxybutyl Acrylate as a Monomer for Thermoresponsive Diblock Copolymer Nano-Objects via RAFT Aqueous Dispersion Polymerization

Deane, Oliver J., et al. Chemical Science 12.41 (2021): 13719-13729.

Stimulus-responsive polymeric nano-objects have attracted significant interest for biomedical applications. This study introduces 4-hydroxybutyl acrylate (HBA) as a monomer for synthesizing thermoresponsive diblock copolymer nano-objects via reversible addition-fragmentation chain transfer (RAFT) aqueous dispersion polymerization using a poly(ethylene glycol) (PEG113) precursor.
Synthesis: PEG113-PHBAx diblock copolymers (x = 200-700) were synthesized at 30 °C, targeting 15% w/w solids. Due to the low glass transition temperature (Tg = -23 °C) of PHBA, glutaraldehyde crosslinking was employed to enable conventional TEM imaging.
Key Results:
· Systematic variation of PHBA degree of polymerization (DP) enabled access to spheres (DP = 200), worms (DP = 350-400), and vesicles (DP ≥ 500) at 20 °C. PEG113-PHBA260 nano-objects exhibited fully reversible morphological transitions: spheres at 10 °C → worms at 36 °C → vesicles at 50 °C, with minimal hysteresis during thermal cycling.
· Variable temperature 1H NMR revealed counter-intuitive UCST-type behavior: PHBA hydration increased from ~5% at 0 °C to ~80% at 60 °C, driving uniform plasticization and morphological evolution-opposite to isomeric PHPMA which shows LCST-type dehydration.
· SAXS analysis quantified solvent volume fraction within PHBA cores increasing from 0.10 (spheres, 10 °C) to 0.68 (vesicles, 50 °C), correlating with hydration changes. Freeze-dried PEG113-PHBAx powders could be reconstituted in water at 20 °C to reform original morphologies.

4-Hydroxybutyl Acrylate as a Functional Comonomer for Silk Fibroin Grafting in Biomedical Scaffolds

Taddei, Paola, et al. International Journal of Biological Macromolecules 107 (2018): 537-548.

Silk fibroin is a promising biomaterial for tissue engineering due to its biocompatibility and mechanical properties, but its surface characteristics often require modification to optimize cell interactions. In this study, 4-hydroxybutyl acrylate (HBA) was employed as a comonomer with 2-hydroxyethyl methacrylate (HEMA) for grafting onto Bombyx mori silk fabrics, followed by electrospinning into nanofibrous scaffolds for soft tissue engineering applications. Grafted silk fabrics were dissolved in trifluoroacetic acid, electrospun, and treated with aqueous methanol to induce β-sheet formation.
Key Results:
· In HEMA/HBA-grafted fabrics (HEMA30_HBA5 and HEMA25_HBA10, total weight gains 24% and 20%), Raman analysis revealed HBA incorporation of 4.8% and 4.0%, respectively-significantly lower than the HEMA content, confirming preferential grafting of methacrylate over acrylate monomers.
· Contact angle measurements showed that HEMA grafting increased surface hydrophilicity (fabrics: 128°→112°; nanofibers: 104°→81°). Addition of HBA slightly increased contact angle, consistent with its longer aliphatic chain imparting greater hydrophobicity. Contact angle correlated linearly with HEMA content.
· Fibroblast viability assays after 3 days demonstrated that nanofibrous scaffolds supported significantly higher cell growth than corresponding fabrics. The HEMA25_HBA10-grafted fabric showed improved proliferation over control silk at day 1, while all nanofibers exhibited enhanced biocompatibility, indicating that topography and surface chemistry modulate cell response. Electrospinning produced uniform nanofibers (diameter ~300 nm) that maintained morphology after methanol treatment, with pore sizes (0-1 μm) preventing cell infiltration during initial culture.

Custom Q&A

What is the product name of this chemical compound?

The product name of this chemical compound is 4-Hydroxybutyl acrylate.

How can 4-Hydroxybutyl acrylate be synthesized?

4-Hydroxybutyl acrylate can be synthesized by the esterification of acrylic acid with 1, 4 butanediol over a catalyst such as Amberlyst 15.

What properties does 4-Hydroxybutyl acrylate exhibit?

4-Hydroxybutyl acrylate exhibits properties such as luster, chemical and scratch resistance.

What are some synonyms for 4-Hydroxybutyl acrylate?

Some synonyms for 4-Hydroxybutyl acrylate include 1,4-Butanediolmonoacrylate, 4-Hydroxybutyl2-propenoate, and Tetramethylene glycol monoacrylate.

What is the molecular weight of 4-Hydroxybutyl acrylate?

The molecular weight of 4-Hydroxybutyl acrylate is 144.17.

What is the IUPAC name of 4-Hydroxybutyl acrylate?

The IUPAC name of 4-Hydroxybutyl acrylate is 4-hydroxybutyl prop-2-enoate.

What is the boiling point of 4-Hydroxybutyl acrylate?

The boiling point of 4-Hydroxybutyl acrylate is 95 °C/0.1 mmHg (lit.).

What are some features and benefits of using 4-Hydroxybutyl acrylate?

Some features and benefits of using 4-Hydroxybutyl acrylate are high-quality products, fast delivery, and the ability to order additional products.

How is 4-Hydroxybutyl acrylate used in applications?

4-Hydroxybutyl acrylate was one of the monomers utilized in the preparation of poly(2-hydroxy-3-phenoxypropylacrylate, 4-hydroxybutyl acrylate, dibutyl maleate) membranes.

How should 4-Hydroxybutyl acrylate be stored?

4-Hydroxybutyl acrylate should be stored at a temperature between 2-8°C.