Exploring the Properties, Applications, and Safety of Bis(4-hydroxyphenyl) Sulfone

General Description

Bis(4-hydroxyphenyl) sulfone is a sulfone compound with white needle-like crystals. It is soluble in aliphatic hydrocarbons, alcohols, and ethers, but insoluble in water. The compound has two hydroxyl groups and a sulfone group, making it more acidic than other phenols. It is used as an intermediate in the production of fine chemicals, electroplating solvent, washfastening agent, and a component in phenolic resins. However, Bis(4-hydroxyphenyl) sulfone is classified as a hazardous chemical with reproductive toxicity and can cause eye irritation. Proper handling and disposal methods are required. Manufacturers must comply with environmental and public health regulations.

Figure 1. Bis(4-hydroxyphenyl) Sulfone,

Properties

Bis(4-hydroxyphenyl) Sulfone, also known as 4,4'-Sulfonyldiphenol, is a sulfone compound that is structurally similar to bisphenol A (BPA). It exists as white needle-like crystals and is freely soluble in aliphatic hydrocarbons, soluble in alcohols and ethers, slightly soluble in aromatics, but insoluble in water. The molecule of Bis(4-hydroxyphenyl) Sulfone contains two hydroxyl groups and a strong electron-absorbing sulfone group, making it more acidic than other phenols. Computed properties of Bis(4-hydroxyphenyl) Sulfone include a molecular weight of 250.27 g/mol, XLogP3 value of 1.9, two hydrogen bond donor counts, four hydrogen bond acceptor counts, and two rotatable bond counts. Its exact mass and monoisotopic mass are both 250.02997997 g/mol. The compound has a topological polar surface area of 83Ų and a heavy atom count of 17. Experimentally, Bis(4-hydroxyphenyl) Sulfone is described as a white, crystalline powder with a melting point of 240.5°C. It is insoluble in water but soluble in ethanol, ether, and slightly soluble in benzene and DMSO. The density of the compound is 1.3663 g/cu cm at 15°C. When heated to decomposition, Bis(4-hydroxyphenyl) Sulfone emits toxic fumes of sulfur oxides. ¹

Applications

Bis(4-hydroxyphenyl) sulfone has various applications in different industries. It is used as an intermediate in the production of fine chemicals, such as polymers and paper. It is also used as an electroplating solvent, a washfastening agent, and a component in phenolic resins. The chemical is patented for several applications, including as a developer in thermal paper and as a processing aid. In the manufacturing industry, Bis(4-hydroxyphenyl) sulfone is used as a dye, etching agent, fixing agent, monomer, polymerization promoter, surfactant, and processing aid. In the consumer sector, it is used as an etching agent, fixing agent, intermediates, polymerization promoter, and processing aid. The chemical has been listed as a High Production Volume (HPV) chemical, produced in or imported into the US in >1 million pounds in 1990 and/or 1994. The production volume for non-confidential chemicals reported under the Inventory Update Rule ranges from >1 million to <10 million pounds from 1986 to 2006. Industries that use Bis(4-hydroxyphenyl) sulfone include adhesive manufacturing, paper manufacturing, plastics material and resin manufacturing, printing and related support activities, and textiles, apparel, and leather manufacturing. ²

Safety

Bis(4-hydroxyphenyl) Sulfone is classified as a hazardous chemical with reproductive toxicity. It can cause damage to fertility and the unborn child, according to GHS classification. The material also causes mild eye irritation and no skin irritation in rabbits. In oral studies of rats, it has been observed to cause prolonged estrous cycles, decreased fertility index, and decreased numbers of live offspring at 300 mg/kg/day. The chemical may also cause acute renal tubular changes and weight loss in rats. Hence, Bis(4-hydroxyphenyl) Sulfone requires proper handling and disposal methods. In case of accidental release, the most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. The ultimate disposal of the chemical must consider its impact on air quality, potential migration in soil or water, effects on animal and plant life, and conformance with environmental and public health regulations. Manufacturers of Bis(4-hydroxyphenyl) Sulfone must report preliminary assessment information concerned with production, exposure, and use to EPA under Section 8(a) of TSCA, and submit copies and lists of unpublished health and safety studies under section 8(d) of TSCA. ³

Reference

1. 4,4'-Sulfonyldiphenol. National Center for Biotechnology Information, 2023, PubChem Compound Summary for CID 6626.

2. PubChem Annotation Record for Bisphenol S. National Center for Biotechnology Information, 2023, Source: Hazardous Substances Data Bank.

3. 4,4'-Sulfonyldiphenol. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases, 19979.