Disodium 3,3'-disulfonate-4,4'-difluorobenzophenone

• CAS: 210531-45-6
• Catalog Number: ACM210531456
• Category: Main Products
• Molecular Weight: 422.29
• Molecular Formula: C₁₃H₆F₂O₇S₂.2Na
• Synonyms: 4,4'-Difluorodiphenylketone-3,3'-disulfonic acid disodium salt;Disodium 3,3'-disulfonate-4,4'-difluorobenzophenone
• IUPAC Name: disodium;2-fluoro-5-(4-fluoro-3-sulfonatobenzoyl)benzenesulfonate
• SMILES: C1=CC(=C(C=C1C(=O)C2=CC(=C(C=C2)F)S(=O)(=O)[O-])S(=O)(=O)[O-])F.[Na+].[Na+]
• InChI Key: TXOMILLKBNFCOJ-UHFFFAOYSA-L
• Exact Mass: 421.93200

Case Study

Disodium 3,3'-Disulfonate-4,4'-Difluorobenzophenone for the Preparation of SPAEKS-x Copolymer Membranes

Shen, Kunzhi, et al. High performance polymers 28.3 (2016): 315-321.

In this work, a series of novel sulfonated poly(arylene ether ketone sulfone) copolymers (SPAEKS-x) were synthesized by polycondensation reaction using biphenol A (BPA), 4,4'-dichlorodiphenylsulfone (DCDPS), 4,4'-dihydroxydiphenylether (DHDPE), and 3,3'disulfonate-4,4'-difluorobenzophenone (SDFB). as raw materials. The sulfonation degree was precisely controlled by varying SDFB monomer content.
Synthesis Details of Copolymers
For SPAEKS-30 synthesis: In a 50-mL three-necked flask with Dean-Stark trap and reflux condenser, 1.2669 g (0.003 mol) SDFB, 2.0101 g (0.007 mol) DCDPS, 1.1415 g (0.005 mol) BPA, 1.0111 g (0.005 mol) DHDPE, 1.4512 g (0.0105 mol) K2CO3, 16 mL DMSO, and 8 mL toluene were dehydrated at 145°C (3 h) after the stirred reaction (15 min, room temperature) and removal of toluene, then were polymerized at 170°C (4 h). The copolymer product was precipitated in water, washed with water/ethanol and vacuum-dried at 120°C (97% yield) to afford SPAEKS-30.
Preparation and Performance of SPAEKS Membranes
The solution casting method was used to achieve the preparation of tough, flexible and transparent SPAEKS-x membranes. SPAEKS-x membranes with IEC = 1.44 meq·g-1 achieved proton conductivity comparable to Nafion 117 across 20-100°C, indicating its potential as an ion exchange membrane in proton exchange membrane fuel cells.

Novel SPEEK-BPA Polymer Prepared from Disodium 3,3'-Disulfonate-4,4'-Difluorobenzophenone for Superlubricating Composites

Wu, Minsong, et al. Composites Part A: Applied Science and Manufacturing 180 (2024): 108113.

A novel bisphenol-A type sulfonated polyether ether ketone (SPEEK-BPA) was synthesized via nucleophilic substitution polycondensation using three monomers: bisphenol A (BPA), bis(4-fluorophenyl)methanone, and disodium 3,3'-disulfonate-4,4'-difluorobenzophenone. This molecular design introduced sulfonate groups (-SO3-) critical for enhanced tribological performance. This case study validates disodium 3,3'-disulfonate-4,4'-difluorobenzophenone as an essential monomer for synthesizing advanced tribological polymers, enabling material solutions where superlubricity and wear resistance are critical.
· Composite Fabrication: SPEEK-BPA was compounded with 10 wt% carbon fiber (CF) through ball milling and vacuum hot pressing, yielding the SPEEK-BPA/10%CF composite. This integration leveraged both the ionic functionality of the sulfonated polymer and the mechanical reinforcement of CF.
· Tribological Performance: When lubricated with 3 wt% NaCl solution at 0.10 m/s sliding speed, SPEEK-BPA/10%CF achieved ultra-low friction coefficient (COF) of 0.009 - approaching superlubricity, and demonstrated exceptional wear resistance with wear rates of 10^-7-10^-8 mm³/(N·m), significantly outperforming commercial PEEK.
· Functional Mechanism: The superlubricity originates from the hydrated sodium ion adsorption by sulfonate groups (-SO3-) forming a boundary lubrication layer, and the mechanical reinforcement from carbon fiber networks.

Proton exchange membrane materials synthesized by using disodium 3,3'-disulfonate-4,4'-difluorobenzophenone

Gao, Yan, et al. Journal of membrane science 278.1-2 (2006): 26-34.

Sulfonated polyphthalide ketone nitrile copolymers (SPPEKN) were prepared by copolymerizing disodium 3,3'-disulfonate-4,4'-difluorobenzophenone (SDFB-Na), 2,6-difluorobenzonitrile (2,6-DFBN), and 4-(4-hydroxyphenyl)-1(2H)-phthalazinone (DHPZ) in N-methyl-2-pyrrolidinedione containing anhydrous potassium carbonate at 160°C. The polymerization proceeded smoothly with high yields, yielding high-molecular-weight SPPEKN copolymers with varying sulfonic acid contents (SC). Membranes of SPPEKN copolymers in both salt and acid forms were cast from polymer solutions in N,N-dimethylacetamide (DMAc) at feed ratios of SDFB-Na to 2,6-DFBN up to 60/40 mol/mol. All SPPEKN copolymers exhibited higher tensile strengths than Nafion 117.
Disodium 4,4-difluorobenzaldehyde (SDFB-Na), 2,6-difluorobenzonitrile (2,6-DFBN), 4-(4-hydroxyphenyl)-1(2H)-phthalazinone (DHPZ), and potassium carbonate were added. NMP and chlorobenzene were then added to the reaction flask under argon. The reaction mixture was heated to 140°C. After dehydration and removal of chlorobenzene (approximately 3-4 hours), the reaction temperature was increased to approximately 165°C. After 5-7 hours, when the solution viscosity has significantly increased, dilute the solution with NMP and continue the reaction for another 3-5 hours. The mixture is then cooled to 100°C and coagulated in a large excess of ethanol with vigorous stirring. After recovering the product, the SPPEKN-40 is washed with deionized water to remove residual solvent and salts.