Bis(4-hydroxyphenyl) Sulfone CAS 80-09-1

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Bis(4-hydroxyphenyl) Sulfone is an organic compound, white needle crystal. Easily soluble in aliphatic hydrocarbons, soluble in ethanol, isopropanol, 2-ethylhexanol, acetonitrile, acetone, slightly soluble in aromatic hydrocarbons, slightly soluble in ethyl acetate, methyl isobutyl ketone, insoluble in toluene, water. It has two phenolic functional groups flanking the sulfonyl group. It is commonly used to cure fast-drying epoxy adhesives. It is classified as a bisphenol, a close molecular analogue of bisphenol A (BPA). BPS is distinguished from BPA by having a sulfone group (SO2) as the central linker of the molecule instead of a dimethylmethylene group (C(CH3)2), as is the case with bisphenol-A.

● Bis(4-hydroxyphenyl) Sulfone is mainly used as a color fixing agent. Fixing agent A (foreign trade name CibatexPA) can be prepared from bisphenol S as raw material. Handling and storage: Wash the whole body thoroughly after handling. Remove contaminated clothing and wash before reuse.

● Used in coatings, leather modifiers, dye intermediates, metal plating brighteners, etc.

● Used as a monomer for the synthesis of polysulfone resin

● Used as plating solution additive, leather tanning agent, dispersant for high-temperature dyeing of disperse dyes, phenolic resin hardening accelerator, resin flame retardant, etc.

● Used as intermediates of pesticides, dyes and auxiliaries

● As a substitute for bisphenol A, it can be used as a raw material for polycarbonate, epoxy resin, polyester, phenolic resin, polysulfone and polyethersulfone.

● Used in the manufacture of color photographic materials, photographic contrast intensifiers, heat-sensitive recording materials (color developers), daily-use surfactants and high-efficiency deodorants, etc.

Method 1: the synthetic method of Bis(4-hydroxyphenyl) Sulfone epoxy resin, synthesizes bisphenol S epoxy resin by one-step method of phase transfer catalyst, and the specific steps of this synthetic method are as follows:

(1) Feeding: Add a certain amount of 125g of bisphenol S, 700g of epichlorohydrin and 3g of tetrabutylammonium bromide into a four-necked flask equipped with a stirring paddle, a thermometer and a condenser, and mix and stir evenly in the four-necked flask , then dropwise add the catalyst sodium hydroxide that accounts for 2% of raw material total amount in flask;

(2) Control the reaction conditions: raise the temperature to 80°C to carry out the synthesis reaction, and react for 1 hour;

(3) Synthetic product: after the above reaction, the reactant solution was left at room temperature for 20 hours to obtain 795 g of a white precipitated product.

Method 2: the method for bisphenol S epoxy resin, comprises the process of synthesis and aftertreatment, is characterized in that:

(1) Mix bisphenol S and epichlorohydrin with a molar weight of 1:2 to 20 in a three-necked flask equipped with a condenser tube and a thermometer, wherein the bisphenol S is dissolved in a solvent.

(2) Control the reaction temperature at 0° C. to 80° C., dropwise add alkali substances, the molar ratio of alkali to bisphenol S is 1 to 3:1, and dissolve with a solvent.

(3) After reacting for 0.5 to 50 hours, filter under reduced pressure to obtain a solid

(4) adding deionized water to repeatedly wash the product, so that the pH value of the washing liquid is 6-8, and bisphenol S epoxy resin is obtained.

Bis(4-hydroxyphenyl) Sulfone epoxy resin is a new type of epoxy resin. Due to the introduction of -SO2- polar groups, it has better flexibility, compressive strength and thermal stability than traditional bisphenol A epoxy resin . Its glass transition temperature is more than 40°C higher than that of bisphenol A epoxy resin system under the same curing conditions. With the rapid expansion of the application of polymer materials, there are more and more researches on bisphenol S epoxy resin. RainerE, UdoG, HeinrichHW, etc. synthesized bisphenol S epoxy resin in a two-step method. The process is complex and requires multiple experiments, which increases the workload of the experiment. SykoraV, SpacekV.J.Appl their synthetic bisphenol S epoxy resin, its epoxy value is low, has influenced the application of bisphenol S bonding performance. In view of the above phenomenon, the following two methods are available: (1) use alkali as a catalyst and directly synthesize bisphenol S epoxy resin by one-step precipitation method. The bisphenol S epoxy resin obtained by this synthesis method has good chemical stability and thermal stability. Yes, it has good bonding performance, but the reaction conditions of this method are not easy to control; (2) One-step synthesis of bisphenol S epoxy resin with phase transfer catalyst, the process is simple, the synthesized product has high purity and less impurities, and the epoxy value High, but the tetramethylammonium bromide used in the method has a melting point > 300°C, which makes the reaction temperature very high in the reaction process, and the reaction time is also prolonged, thus affecting work efficiency. Therefore, research and develop a kind of product yield height, the synthetic method of the bisphenol S epoxy resin that epoxy value is high and reaction time shortens, work efficiency improves.

● Development of BPS Analogs and Alternatives

Researchers are exploring BPS analogs with improved properties, such as reduced toxicity, enhanced solubility, or increased reactivity. These analogs aim to expand the applications of BPS while addressing environmental and health concerns.

1) Green Chemistry Approaches:
The development of eco-friendly synthetic routes for BPS and its analogs, using renewable feedstocks and minimizing waste, aligns with global sustainability goals. Biocatalytic methods and solvent-free reactions are among the approaches being investigated.

2) Toxicity Reduction:
By modifying the chemical structure of BPS, researchers aim to reduce its potential toxicity while maintaining or enhancing its desirable properties. This may involve substituting functional groups or altering the molecular architecture.

● Biodegradable Polymers and Materials

Incorporating BPS into biodegradable polymer systems could address environmental concerns associated with traditional plastics. Research is ongoing to develop BPS-based polymers with enhanced biodegradability without compromising performance.

1) Compostable Packaging:
BPS-derived biodegradable polymers could be used in compostable packaging materials, reducing the environmental impact of plastic waste. These materials would decompose naturally under composting conditions, returning nutrients to the soil.

2) Sustainable Composites:
In composite materials, BPS-based biodegradable polymers could replace non-biodegradable matrices, enabling the production of sustainable composites with reduced environmental footprints.

● Nanotechnology Integration

Exploring the use of BPS in nanomaterials and nanocomposites may lead to breakthroughs in energy storage, catalysis, and biomedical applications. BPS-derived nanoparticles could offer unique properties for targeted drug delivery or advanced sensors.

1) Drug Delivery Nanoparticles:
BPS-based nanoparticles could be engineered to encapsulate and deliver drugs to specific tissues or cells, improving therapeutic efficacy and reducing side effects. Their biocompatibility and tunable properties make them promising candidates for drug delivery systems.

2) Catalytic Nanomaterials:
In catalysis, BPS-derived nanomaterials could serve as efficient catalysts for chemical reactions, offering high activity and selectivity. Their stability and recyclability make them attractive for industrial applications.

● Public Perception and Education

Addressing public concerns about BPS requires transparent communication and education about its benefits and risks. Stakeholders, including manufacturers, regulators, and consumer advocacy groups, should work together to provide accurate information and promote informed decision-making.

1) Labeling and Transparency:
Clear labeling of BPS-containing products can help consumers make informed choices. Manufacturers should disclose the presence of BPS and provide information about its safety and environmental impact.

2) Public Awareness Campaigns:
Educational campaigns can raise awareness about the uses and benefits of BPS, as well as the importance of proper disposal and recycling of BPS-containing products. These campaigns can empower consumers to take an active role in reducing environmental impacts.

Bis(4-hydroxyphenyl) Sulfone (a compound with a unique chemical structure, CAS number 80-09-1) is an organic compound with a molecular formula of C₁₂H₁₀O₄S and a molecular weight of 250.27 g/mol. This compound is formed by connecting two 4-hydroxyphenyl groups through the sulfone group (-SO₂-). Its chemical properties mainly manifest in aspects such as physical state, solubility, thermal stability, acidity and basicity, and reactivity.

Physical state and appearance

Bis(4-hydroxyphenyl) Sulfone appears as white needle-like crystals or powder at room temperature, with a definite crystal structure. It has a relatively high melting point, usually ranging from 245°C to 250°C, indicating strong intermolecular forces and a stable crystal structure. The boiling point is as high as 505.3°C (760 mmHg), further confirming its thermal stability. The density is approximately 1.4 g/cm³ (25°C), and the vapor pressure is extremely low (0.0±1.3 mmHg at 25°C), indicating that the compound is not volatile at room temperature and is suitable for storage in a sealed environment.

 

Thermal stability and chemical stability

Bis(4-hydroxyphenyl) Sulfone exhibits excellent thermal stability. Its high melting point and boiling point enable it to maintain structural integrity at high temperatures. The sulfone group (-SO₂-) acts as a strong electron-withdrawing group, stabilizing the molecular structure through an inducing effect and reducing the possibility of thermal decomposition or oxidation reactions. Additionally, this compound is stable to air, light, and most chemical reagents (such as dilute acids and dilute bases) at room temperature, but it may degrade in the presence of strong oxidants or reductants.

 

Acid-base property

The two hydroxyl groups in the molecule confer weak acidity to Bis(4-hydroxyphenyl) Sulfone. The strong electron-withdrawing effect of the sulfone group reduces the electron cloud density on the hydroxyl oxygen, thereby enhancing the polarity of the O-H bond and facilitating the release of hydrogen ions (H⁺). Therefore, its acidity is stronger than that of common phenolic compounds (such as phenol), but weaker than that of carboxylic acids. This property enables it to serve as a catalyst or reactant in certain reactions that require weak acidic conditions.

 

Reactivity

The chemical reactivity of Bis(4-hydroxyphenyl) Sulfone is mainly concentrated on the hydroxyl group and the sulfone group:

 Hydroxyl reaction: It can participate in esterification, etherification, acylation and other reactions. For example, it can react with acyl chloride to form ester derivatives, or react with halogenated hydrocarbons to form ether compounds.

 Sulfonyl reaction: The strong electron-withdrawing effect of the sulfonyl group makes it a potential attack site for electrophilic reagents. Under specific conditions, the sulfonyl group can be reduced to sulfone or thioether, or other functional groups can be introduced through nucleophilic substitution reactions.

 Polymerization reaction: As a bisphenol compound, Bis(4-hydroxyphenyl) Sulfone can be used to synthesize high-performance engineering plastics such as polysulfone and polyether sulfone. The hydroxyl group of it can undergo condensation polymerization with diphenyl sulfonyl dichloride to generate polysulfone resin, which has excellent heat resistance, mechanical strength and chemical stability.

 

Storage conditions

To maintain the chemical stability of Bis(4-hydroxyphenyl) Sulfone, it is recommended to store it in a dry environment at 4°C; for long-term preservation, -4°C conditions are more ideal. The storage container should be tightly sealed to prevent contact with strong oxidants, reductants or humid air.

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