4,4'-Sulfonyldiphenol

Other Classes -> Benzenesulfonic Acid Derivatives

Bisphenol

White, crystalline powder

Needles (from water), orhombic bipyramidol

Insoluble in water

Soluble in ethanol, ether; slightly soluble in benzene, DMSO

Dry Powder

White solid; [HSDB] Slightly beige crystalline powder; [Acros Organics MSDS]

155.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3022409]

155.49 Ų [M-H]-

Danger

H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 47.3% (245 of 518) of reports.

Danger

H360 (16.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Chemical: Phenol, 4,4'-sulfonylbis-

Hazard Traits - Endocrine Toxicity; Reproductive Toxicity

Phenol, 4,4'-sulfonylbis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 4,4'-sulfonylbis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 02-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14986

Substance: 4,4'-sulphonyldiphenol

4,4'-Sulphonyldiphenol: Does not have an individual approval but may be used under an appropriate group standard

Causes mild eye and no skin irritation in rabbits; No evidence of skin sensitization in animals; Histopathological changes of the liver, prolonged estrous cycle, decreased fertility index, and decreased number of live offspring observed in oral study of rats at 300 mg/kg/day; [EPA] Causes effects on food intake, acute renal tubular changes, and weight loss in 13-day intermittent oral studies of rats; [RTECS] An eye irritant; [Acros Organics MSDS] See Bisphenol A. See Dapsone.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Bisphenol S is included on this list. Effective date: 9/30/91; Sunset date: 12/19/95.

Repr. 1B (16.2%)

Reproductive toxicity - category 2

Reproductive toxicity - Category 1B

Repr. 1B

SRP: 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. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Bisphenol S was detected in 81% of urine samples from populations in New York (Albany, n = 31) and seven Asian countries (China, n = 89; India, n = 38; Japan, n = 36, Korea, n = 33; Kuwait, n = 30; Malaysia, n = 29; and Vietnam, n = 29). The urinary bisphenol S concentrations varied among countries, with the highest geometric mean (GM) concentrations found in samples from Japan (GM 1.18 ng/mL, 0.933 g/g creatinine) and New York (GM 0.299 ng/mL, 0.304 g/g creatinine)(1).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), using an estimated log Kow of 1.65(2) and a regression-derived equation(2), indicates that bisphenol S is expected to have moderate mobility in soil(SRC). The estimated pKa of bisphenol S is 8.2(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of Bisphenol S from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.7X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Bisphenol S is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Bisphenol S was not biodegraded in 22-day aerobic river die-away tests(5), indicating that biodegradadtion is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), using an estimated log Kow of 1.65(2) and a regression-derived equation(2), indicates that bisphenol S is not expected to adsorb to suspended solids and sediment(SRC). The estimated pKa of bisphenol S is 8.2(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 2.7X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(6), an estimated BCF of 6(SRC), from an estimated log Kow of 1.65(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Bisphenol S was not biodegraded in 22-day aerobic river die-away tests(7), indicating that biodegradadtion is not an important environmental fate process in water(SRC). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy radicals with half-lives on the order of days to weeks at the water surface(8); therefore, photo-oxidation may be an important fate process for Bisphenol S in natural water(SRC). Bisphenol S is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bisphenol S, which has an estimated vapor pressure of 4.7X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bisphenol S may be removed from the air by wet and dry deposition(SRC).

Bisphenol S was detected in seven out of nine canned vegetable samples; when bisphenol S was detected, it was found in the supernatant liquid from the canned food at higher levels than in the food itself; the highest bisphenol S concentration measured was in a sample of supernatant liquid from canned peas and carrots (170 or 175 ng/g, depending on the derivatization method). The source of the bisphenol S in the canned foods is the result of migration from the resin or plastic linings used in the containers(1).

Using an estimated log Kow of 1.65(1) and a regression-derived equation(1), the Koc of bisphenol S can be estimated to be 160(SRC). According to a classification scheme(2), this estimated Koc value suggests that bisphenol S is expected to have moderate mobility in soil. The estimated pKa of bisphenol S is 8.2(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

/BIOMONITORING/ As concern regarding the toxic effects of bisphenol A (BPA) grows, BPA in many consumer products is gradually being replaced with compounds such as bisphenol S (BPS). Nevertheless, data on the occurrence of BPS in human specimens are limited. In this study, 315 urine samples, collected from the general populations in the United States, China, India, Japan, Korea, Kuwait, Malaysia, and Vietnam, were analyzed for the presence of total BPS (free plus conjugated) concentrations by high-performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS). BPS was detected in 81% of the urine samples analyzed at concentrations ranging from below the limit of quantitation (LOQ; 0.02 ng/mL) to 21 ng/mL (geometric mean: 0.168 ng/mL). The urinary BPS concentration varied among countries, and the highest geometric mean concentration (1.18 ng/mLor 0.933 ug/g creatinine (Cre)) of BPS was found in urine samples from Japan, followed by the United States (0.299 ng/mL, 0.304 ug/g Cre), China (0.226 ng/mL, 0.223 ug/g Cre), Kuwait (0.172 ng/mL, 0.126 ug/g Cre), and Vietnam (0.160 ng/mL, 0.148 ug/g Cre). Median concentrations of BPS in urine samples from the Asian countries were 1 order of magnitude lower than the median concentrations reported earlier for BPA in the same set of samples, with the exception of samples from Japan. There were no significant differences in BPS concentrations between genders (male versus female), or among age groups (categorized as = 19, 20-29, 30-39, 40-49, and = 50 years), or races (Caucasian versus Asian). The daily intake (EDI) of BPS was estimated on the basis of urinary concentrations using a simple pharmacokinetic approach. The median EDI values of BPS in Japan, China, United States, Kuwait, Vietnam, Malaysia, India, and Korea were 1.67, 0.339, 0.316, 0.292, 0.217, 0.122, 0.084, and 0.023 ug/person, respectively.

/OTHER TOXICITY INFORMATION/ In 2011, the European Commission has restricted the use of Bisphenol A in plastic infant feeding bottles. In a response to this restriction, Bisphenol S is now often used as a component of plastic substitutes for the production of babybottles. One of the major concerns leading to the restriction of Bisphenol A was its weak estrogenic activity. By using two highly standardised transactivation assays, we could demonstrate that the estrogenic activity of Bisphenol A and Bisphenol S is of a comparable potency. Furthermore, some insights about the structure-activity relationships of these two chemicals and their metabolites could be gained from in silico predictions of their relative estrogen receptor-binding affinities and their liver phase-I biotransformation.

Bisphenol S's production and use as an intermediate(1), as an electroplating solvent, washfastening agent, component in a phenolic resin(2) and as a developer in thermal paper(3) may result in its release to the environment through various waste streams(SRC).

AEROBIC: Bisphenol S is reported to be non-biodegradable in the Japanese MITI test(1). In 22-day aerobic river die-away tests using several river water samples in 24 microcosms, bisphenol S showed no degradation in all 24 microcosms(2). No biodegradation of bisphenol S was observed in laboratory tests using seawater(3).

ANAEROBIC: In anaerobic biodegradation tests using pond sediment, bisphenol S showed about 75% degradation over 84 days of incubation(1).

An estimated BCF of 6 was calculated in fish for bisphenol S(SRC), using an estimated log Kow of 1.65(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). Bisphenol S is reported to have low bioconcentration(3).

The Henry's Law constant for bisphenol S is estimated as 2.7X10-15 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bisphenol S is expected to be essentially nonvolatile from water surfaces(2). Bisphenol S's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Bisphenol S is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-10 mm Hg(SRC), determined from a fragment constant method(1).

/ALTERNATIVE and IN VITRO TESTS/ Alkylphenol ethoxylates, widely used non-ionic surfactants, are biodegraded into alkylphenols such as nonylphenol (NP) and t-octylphenol (OP), short-chain ethoxylates such as NP-monoethoxylate (NP1EO) and NP-diethoxylate (NP2EO), and alkylphenoxy carboxylic acids such as 4-t-octylphenoxyacetic acid (OP1EC). Bisphenol S (BPS) is more heat-stable and photo-resistant than bisphenol A (BPA), and therefore replaces BPA. These chemicals could be chlorinated during wastewater treatment. /The researchers/ synthesized these compounds and their chlorinated derivatives to estimate their estrogenic activities using a GFP expression system. The EC(50) ranking of NP-related compounds was NP > ClNP > diClNP > NP1EO > ClNP1EO > NP2EO. The estrogenic activity of OP1EC was 10 times less potent than parent OP. Furthermore, BPS showed comparable estrogenic activity with BPA. The EC(50) ranking of BPS-related compounds was BPA = BPS > triClBPS > diClBPS > ClBPS. Other tested BPS derivatives had no estrogenic activity. Chlorination of the tested chemicals did not enhance their estrogenic activity, in contrast to certain chlorinated BPAs. Thus, our results demonstrated that chlorinated derivatives of NP, OP, and BPS, even if artificially produced during wastewater processing, were less estrogenic than their parent chemicals, known as endocrine disruptors.

/ALTERNATIVE and IN VITRO TESTS/ The estrogenic activities of 13 Bisphenol-A (BPA)-related chemicals for development of new polymers by three in vitro bioassay have been examined in the presence and absence of a post-mitochondrial metabolizing system (S9 mix). BPA, Bisphenol-B (BPB), Bisphenol-F (BPF), Bisphenol-S (BPS), 4,4-ethylidenebisphenol (BP1), 4,4-dihydroxybenzophenone (BP2), 2,2-bis (4-hydroxyphenyl)-hexafluoropropane (BP3), 4,4-(1,4-phenylenediisopropylidene) bisphenol (BP4), 4,4-cyclohexylidenebisphenol (BP5), 4,4-dihydroxydiphenyl ether (BP6), 4-hydroxydiphenylmethane (BP7), 4-cumylphenol (BP8) and 4,4-dihydroxydiphenyl sulfide (BP9) were each diluted with dimethyl sulfoxide to final concentrations ranging from 10(-7) to 10(-3) M in both the yeast two-hybrid system and in a fluorescence polarization system. Dilutions of 10(-9) to 10(-4) M were assayed in the E-screen, respectively. Except for BPS and BP4, the chemicals tested showed estrogenic activity in the absence of cut S9 mix preparation and the activity was enhanced with S9 mix. BPS, which was initially negative, was active with S9 mix in the yeast two-hybrid system. BP2 was weakly estrogenic with or without S9 mix. Chemicals other than BP2 were positive in the competition binding assay. All chemicals tested showed estrogenic activity in the E-screen, the concentration level of which was 10(4) times lower than those of the other two assays.

The rate constant for the vapor-phase reaction of bisphenol S with photochemically-produced hydroxyl radicals has been estimated as 1.45X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Bisphenol S is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy (RO2) radicals with half-lives on the order of days to weeks at the water surface(3); therefore, photo-oxidation may be an important fate process for bisphenol S in natural water(SRC).

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Bisphenol S is included on this list. Effective date: 9/30/91; Sunset date: 12/19/95.

Used as an intermediate, electroplating solvent, washfastening agent, in phenolic resins, and as a developer in thermal paper; [HSDB] Used to make paper, polymers, and fine chemicals; [ECHA REACH Registrations]

Electroplating [Category: Plate]

Intermediate, product modification

Has been patented for a variety of applications, eg, as an electroplating solvent, a washfastening agent, and a component in a phenolic resin

Bisphenol S is used as a developer in thermal paper, including in products marketed as "BPA-free paper".

2023: 2,500,000 - <4,000,000 lb

Phenol, 4,4'-sulfonylbis- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8065]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Phenol, 4,4'-sulfonylbis-. Aggregated National Production Volume: 1 to < 10 million pounds.

Printing and Related Support Activities

Phenol, 4,4'-sulfonylbis-: ACTIVE