CAS 3068-88-0 β-Butyrolactone - Analytical Products / Alfa Chemistry

CAT	AP3068880
CAS	3068-88-0
Structure
MDL Number	MFCD00005170
Molecular Weight	86.09
EC Number	221-330-3
InChI Key	GSCLMSFRWBPUSK-UHFFFAOYSA-N

Description	analytical standard
Density	1.056 g/mL at 25 °C (lit.)
Assay	≥97.0% (GC)
BP	71-73 °C/29 mmHg (lit.)
Form	neat; gas chromatography (GC): suitable
Grade	analytical standard
Impurity Content	≤0.5% water
MP	−43.5 °C (lit.)
Refractive Index	n20/D 1.411 (lit.); n20/D 1.412-1.414
Size	1ML, 5ML

Anionic Polymerization of β-Butyrolactone Initiated with Sodium Phenoxides. The Effect of the Initiator Basicity/Nucleophilicity on the ROP Mechanism

Adrian Domiński, Tomasz Konieczny, Magdalena Zięba, Magdalena Klim, Piotr Kurcok

Polymers (Basel). 2019 Jul 22;11(7):1221.

PMID: 31336650

Efficient Synthesis of the Ketone Body Ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and Its (S,S) Enantiomer

Noah Budin, Erin Higgins, Anthony DiBernardo, Cassidy Raab, Chun Li, Scott Ulrich

Bioorg Chem. 2018 Oct;80:560-564.

PMID: 30014924

Highly Controlled Immortal Polymerization of β-butyrolactone by a Dinuclear Indium Catalyst

Cuiling Xu, Insun Yu, Parisa Mehrkhodavandi

Chem Commun (Camb). 2012 Jul 11;48(54):6806-8.

PMID: 22669203

Stereoselective Ring-Opening (Co)polymerization of β-Butyrolactone and ε-Decalactone Using an Yttrium Bis(phenolate) Catalytic System

Jiraya Kiriratnikom, Carine Robert, Vincent Guérineau, Vincenzo Venditto, Christophe M Thomas

Front Chem. 2019 May 22;7:301.

PMID: 31192185

Stereo-selectivity Switchable ROP of rac-β-butyrolactone Initiated by Salan-Ligated Rare-Earth Metal Amide Complexes: The Key Role of the Substituents on Ligand Frameworks

Zhixing Zhuo, Chen Zhang, Yunjie Luo, Yaorong Wang, Yingming Yao, Dan Yuan, Dongmei Cui

Chem Commun (Camb). 2018 Oct 23;54(85):11998-12001.

PMID: 30204162

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Case Study

β-Butyrolactone (BBL) for the Synthesis of Block Copolymers via Controlled Anionic Polymerization

Bochenek, Marcelina, et al. European Polymer Journal 194 (2023): 112116.

β-Butyrolactone (BBL) plays a crucial role in the synthesis of block copolymers, particularly in controlled anionic polymerization. A recent study demonstrated the efficient incorporation of BBL into polyoxirane-based structures using a sequential monomer addition technique. This method relies on the transformation of alkoxide active centers into carboxylates, ensuring high precision in copolymer composition.
In the synthesis, ethoxyethyl glycidyl ether (EEGE) was first polymerized using potassium tert-butoxide as the initiator in tetrahydrofuran (THF) at 55°C. The resulting polyoxirane chains were then modified via a quantitative reaction with succinic anhydride, converting hydroxyl groups into carboxylate centers. Upon addition of freshly distilled BBL and tetrabutylammonium bromide in anhydrous DMSO, polymerization proceeded at room temperature, leading to the formation of well-defined di-, tri-, and pentablock copolymers.
The study highlights BBL's compatibility with controlled polymerization techniques, offering precise control over molecular weight and copolymer architecture. The transformation step was found to be highly efficient, maintaining the integrity of the growing polymer chain while introducing reactive sites for further functionalization. These findings position BBL as a valuable monomer for engineering hydrophilic-hydrophobic copolymer systems, particularly in biomedical and biodegradable materials research.

β-Butyrolactone (BBL) in Enantioselective Terpolymerization with CO₂ and Cyclohexene Oxide

Li, W. B., et al. Organometallics 39.9 (2020): 1628-1633.

β-Butyrolactone (BBL) has been successfully incorporated into enantioselective terpolymerization with carbon dioxide (CO₂) and cyclohexene oxide (CHO), forming high-performance terpolymers with tunable thermal and structural properties. Utilizing an enantiopure bimetallic cobalt catalyst, the reaction proceeds through an intramolecular bimetallic cooperation mechanism, allowing precise control over polymer composition and stereochemistry.
The terpolymerization process, conducted in a one-pot system under controlled CO₂ pressure, produces terpolymers with a single melting temperature (Tm) exceeding 200°C. The carbonate-ester junction content, which directly affects polymer properties, ranges from 10.9% to 28.5%, depending on CO₂ pressure and CHO/BBL feed ratio. Higher CO₂ pressure favors carbonate unit incorporation, while increasing BBL content reduces enantioselectivity. Notably, polymerization does not yield homopolymer poly(3-hydroxybutyrate) (PHB), confirming selective terpolymer formation.
Molecular weight discrepancies between theoretical and experimental values suggest the influence of trace water as a chain transfer agent and potential transesterification side reactions. These findings highlight BBL's critical role in engineering biodegradable and high-performance polycarbonates with precisely tailored properties. This approach paves the way for sustainable polymer synthesis with potential applications in advanced biomaterials and high-temperature-resistant plastics.

β-Butyrolactone (BBL) in the Synthesis of Star-Shaped Poly(β-hydroxybutyrates) via Ring-Opening Polymerization

Omar, Rawan, et al. European Polymer Journal 160 (2021): 110756.

β-Butyrolactone (BBL) is a crucial cyclic ester for synthesizing poly(β-hydroxybutyrates) (PHBs) with well-defined star-shaped architectures through ring-opening polymerization (ROP). Utilizing an amido-oxazolinate zinc catalyst, BBL undergoes controlled polymerization initiated by bio-based multifunctional alcohols, enabling the formation of three-, four-, and multi-armed PHBs.
The core-first approach allows precise molecular design, impacting thermal stability and wettability. Characterization via NMR, GPC, TGA, and DSC confirms the integration of the core structure, while AFM analysis reveals variations in contact angles based on arm number. Increasing the number of arms reduces thermal stability at constant arm lengths, demonstrating tunable thermal behavior.
A typical synthesis involves BBL polymerization in toluene at 100°C under inert conditions, followed by purification via precipitation in hexane. The resulting star-shaped PHBs exhibit controlled molecular weights and dispersity, positioning BBL as an essential monomer for advanced polymer design. These findings highlight its potential in biodegradable materials and functional polymer applications.