2,2'-Ethylidene-bis(4,6-di-tert-butylphenol)

• CAS: 35958-30-6
• Catalog Number: ACM35958306
• Category: Main Products
• Molecular Weight: 438.69
• Molecular Formula: C30H46O2
• Melting Point: 162-164 °C (lit.)

Case Study

2,2'-Ethylidene-bis(4,6-di-tert-butylphenol) as a Key Bisphenol Precursor for Magnesium Polymerization Catalysts

Shen, Min-Yi, et al. Dalton Transactions 44 (2009): 9906-9913.

2,2'-Ethylidene-bis(4,6-di-tert-butylphenol) (EDBP-H2) acts as a foundational bisphenolato ligand precursor for constructing high-performance magnesium catalysts, which drive the ring-opening polymerization (ROP) of ε-caprolactone and L-lactide to synthesize biodegradable polyesters.
Synthetic & Catalytic Protocol: EDBP-H2 is monomethylated to form EDBP-(Me)H, which reacts with nBu2Mg to generate magnesium alkyl intermediates. Subsequent alcoholysis yields dimeric magnesium benzoxide complexes. Catalysts are characterized by NMR, elemental analysis and X-ray crystallography; ROP is conducted under inert atmosphere at 0-25 °C.
Performance Evaluation: Magnesium catalysts derived from EDBP-H2 deliver outstanding activity: >99% conversion of L-lactide within 10 min at 0 °C and 96% conversion of ε-caprolactone in 60 min at 25 °C. The resulting polyesters exhibit narrow polydispersity (PDI 1.06-1.08) and well-controlled molecular weights. The hemilabile EDBP ligand stabilizes catalytic intermediates, enabling living polymerization and outperforming unmodified bisphenol systems for biomedical-grade polyester production.

2,2'-Ethylidene-bis(4,6-di-tert-butylphenol) as Antioxidant and Pore-Regulating Agent for PSU/PET Ultrafiltration Membranes

Rajesh, Smitha, et al. Desalination and Water Treatment 57.55 (2016): 26820-26829.

2,2'-Ethylidene-bis(4,6-di-tert-butylphenol) (EBBP) acts as a dual-functional antioxidant and pore-forming additive for polysulfone/polyethylene terephthalate (PSU/PET) asymmetric ultrafiltration membranes. Combined with polyethylene glycol (PEG), it tunes membrane morphology, hydrophilicity, thermal stability and separation performance.
Fabrication & Characterization Protocol: Membranes were prepared via phase inversion with 5-25 wt% EBBP in dichloromethane. Morphology was observed by SEM, chemical structure by ATR-FTIR. Properties included tensile strength, contact angle, pure water flux, milk protein rejection and antifouling recovery.
Performance Evaluation: 15 wt% EBBP yielded optimal performance: porosity 80.6%, pure water flux 138 L/(m²·h), tensile strength 4.6 MPa and flux recovery 83%. EBBP promoted interconnected macrovoids and improved hydrophilicity; excess loading reduced pore size. It enhanced thermal stability and lowered filtration resistance, enabling efficient protein ultrafiltration with reduced fouling.

2,2'-Ethylidene-bis(4,6-di-tert-butylphenol) as a Bulky Bisphenol Ligand for Heterobimetallic Ti-Catalyzed L-Lactide ROP

Chen, Hsuan-Ying, et al. Inorganic chemistry 49.2 (2010): 665-674.

2,2'-Ethylidene-bis(4,6-di-tert-butylphenol) (EDBP-H2) serves as a sterically hindered bisphenol ligand to construct heterobimetallic Ti-Li, Ti-Na, Ti-Zn, and Ti-Mg complexes, which act as highly efficient initiators for the ring-opening polymerization (ROP) of L-lactide (L-LA) to produce biodegradable poly(L-lactide) (PLLA).
Synthesis & Catalysis Protocol: EDBP-H2 reacts with metal alkyls to form monometallic precursors, which further coordinate with Ti(OⁱPr)₄ to yield heterobimetallic complexes. Polymerizations are carried out in toluene at 30 °C. Complex structures are confirmed by X-ray diffraction; PLLA properties are characterized by NMR and GPC.
Performance Evaluation: Ti-Zn and Ti-Mg complexes exhibit superior activity, achieving >94% L-LA conversion within 30 min. The polymerization follows first-order kinetics (k = 81.64 /M/min) and yields well-controlled PLLA with narrow polydispersity (PDI < 1.29). EDBP-H2 stabilizes the bimetallic active center and greatly enhances catalytic efficiency compared to monometallic Ti systems, supporting scalable green synthesis of biomedical-grade polyesters.