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Home > Encyclopedia > 4,4'-Dichlorodiphenyl sulfone

4,4'-Dichlorodiphenyl sulfone

4,4'-Dichlorodiphenyl sulfone structure

4,4'-Dichlorodiphenyl sulfone 

structure
  • CAS No:

    80-07-9

  • Formula:

    C12H8Cl2O2S

  • Chemical Name:

    4,4'-Dichlorodiphenyl sulfone

  • Synonyms:

    1,1’-sulfonylbis[4-chloro-benzene];4,4'-Dichlorophenyl sulfone;Benzene, 1,1'-sulfonylbis*4-chloro-;Benzene, 1,1'-sulfonylbis[4-chloro-;di-p-chlorophenylsulfone;p,p’-dichlorodiphenylsulfone;p,p'-Dichlorodiphenyl sulfone;p-Chlorophenyl sulfone

  • Categories:

    Organic Chemistry  >  Organosulfur Compounds

Description

off-white crystals or powder


Crystals or off-white powder. (NTP, 1992)|DryPowder; PelletsLargeCrystals


Crystals or off-white powder. (NTP, 1992)


4,4'-Dichlorodiphenyl sulfone (DCDPS) is an important intermediate. It is primarily used in the preparation of aromatic polysulfones and in the synthesis of bis(4-aminophenyl) sulfone, which is used to treat leprosy and cure epoxy resins.


Mildly toxic by ingestion. When heated to decomposition it emitsvery toxic fumes of Cl- and SOx.

4,4'-Dichlorodiphenyl sulfone Basic Attributes

287.16

287.16

2052955

201-247-9

5U49794253

50730|38759|23899|7207

TSCA listed

DTXSID9024986

White

29309070

Characteristics

42.5

3.9

White Fine Powder

1.54g/cm3

143-146 °C(lit.)

250 °C10 mm Hg(lit.)

233 °C

1.610

<0.1 g/100 mL at 20 ºC

Store below +30°C.

0Pa at 25℃

LD50 orl-mus: 24 g/kg HCACAV 29,1317,46

Non flammable

7.0×101mol/(m3Pa) at 25℃, HSDB (2015)

Hydroxyl radical reaction rate constant = 5.9X10-13 cu cm/molec-sec at 25 °C /Estimated/

Insoluble in water.

Sulfonates, Phosphonates, and Thiophosphonates, Organic

4,4'-Dichlorodiphenyl sulfone is incompatible with strong oxidizers.

Sealed in dry,Room Temperature

Safety Information

NONH for all modes of transport

2

Xi,C

22-24/25-37/39-26

WR3450000

Xi,C

Warehouse ventilated, low temperature and dry

Harmful/Corrosive/Moisture Sensitive

Stable. Combustible. Incompatible with strong oxidizing agents.

P264, P273, P280, P305+P351+P338, P337+P313, P391, P501

36/37/38

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Flash point data for 4,4'-Dichlorodiphenyl sulfone are not available; however, 4,4'-Dichlorodiphenyl sulfone is probably combustible.

|Warning|H319 (94.27%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P273, P280, P305+P351+P338, P337+P313, P391, and P501|Aggregated GHS information provided by 258 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is stored, weighed and diluted, wear an approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Non-flammable. ...The product is relatively inert and where other sources provide a fire source it is self extinguishing.

Toxicity

practically nontoxic

LD50 Rat oral >3000 mg/kg bw

Groups of 10 male and 10 female F344/N rats were fed diets containing 0, 30, 100, 300, 1,000, or 3,000 ppm p,p'-dichlorodiphenyl sulfone (equivalent to average daily doses of approximately 2, 6, 19, 65, or 200 mg p,p'-dichlorodiphenyl sulfone/kg bw) for 14 weeks. All rats survived until the end of the study. Mean body weights of groups exposed to 300 ppm or greater were significantly less than those of the controls. Liver weights of groups exposed to 100 ppm or greater and kidney weights of 1,000 and 3,000 ppm male rats were significantly greater than those of the controls. Centrilobular hepatocyte hypertrophy of the liver was observed in most male rats exposed to 100 ppm or greater and in all female rats exposed to 300 ppm or greater, and the severities were increased in 300 ppm males and 1,000 and 3,000 ppm males and females. The incidences of nephropathy in 1,000 and 3,000 ppm female rats were significantly increased. Dose-related increases in severity of nephropathy were observed in male rats.|Groups of 10 male and 10 female B6C3F1 mice were fed diets containing 0, 30, 100, 300, 1,000, or 3,000 ppm p,p'-dichlorodiphenyl sulfone (equivalent to average daily doses of approximately 3.5, 15, 50, 165, or 480 mg/kg) for 14 weeks. All mice survived until the end of the study. Mean body weights of groups exposed to 300 ppm or greater were significantly less than those of the controls. Liver weights of groups exposed to 300 ppm or greater were significantly increased. Centrilobular hypertrophy of the liver was observed in most males exposed to 100 ppm or greater and in all females exposed to 1,000 or 3,000 ppm, and the severities generally increased with increasing exposure concentration.|Groups of 50 male and 50 female rats were fed diets containing 0, 10 (males), 30, 100, or 300 (females) ppm p,p'-dichlorodiphenyl sulfone for 105 weeks. Dietary concentrations of 10, 30, and 100 ppm resulted in average daily doses of approximately 0.5, 1.5, and 5.0 mg/kg to males. Dietary concentrations of 30, 100, and 300 ppm resulted in average daily doses of approximately 1.6, 5.4, and 17 mg/kg to females. Additional groups of 10 male and 10 female rats were fed the same p,p'-dichlorodiphenyl sulfone-containing diets for 18 months and bled for plasma determinations of p,p'-dichlorodiphenyl sulfone at approximately 2 weeks and 3, 12, and 18 months. Survival of all exposed groups of male and female rats was similar to that of the control groups. ...|p,p'-Dichlorodiphenyl sulfone was not mutagenic in any of several strains of Salmonella typhimurium, with or without metabolic activation enzymes (S9). Results of the sister chromatid exchange test in cultured Chinese hamster ovary cells were judged to be negative in the presence of S9 and equivocal in the absence of S9, but no induction of chromosomal aberrations was noted, with or without S9. In contrast to the in vitro results, positive results were obtained in an acute in vivo mouse bone marrow micronucleus assay with p,p'-dichlorodiphenyl sulfone administered by intraperitoneal injection three times over a dose range of 200 to 800 mg/kg.|Groups of 50 male and 50 female mice were fed diets containing 0, 30, 100, or 300 ppm p,p'-dichlorodiphenyl sulfone for 105 to 106 weeks. Dietary concentrations of 30, 100, and 300 ppm delivered average daily doses of approximately 4, 13, and 40 mg/kg to males and approximately 3, 10, and 33 mg/kg to females. Additional groups of 10 male and 10 female mice were fed the same p,p'-dichlorodiphenyl sulfone-containing diets for up to 12 months; three mice in each group were bled for plasma determinations of p,p'-dichlorodiphenyl sulfone at approximately 2 weeks or 3 or 12 months. Survival of all exposed groups of male and female mice was similar to that of the control groups. Mean body weights of 300 ppm mice were less than those of the controls throughout most of the study. Feed consumption by the exposed groups was similar to that by the controls throughout the study. The incidences of centrilobular hepatocyte hypertrophy in all exposed groups of male mice and in 100 and 300 ppm females were significantly greater than those in the controls. The incidence of eosinophilic foci in 300 ppm females was significantly increased. No neoplasms were related to chemical exposure.

4,4-Dichlorophenyl sulfone's production and use as an intermediate in pharmaceutical synthesis(1) and in high temperature plastics(2) may result in its release to the environment through various waste streams(SRC).

4,4'-Dichlorodiphenyl sulfone (DCDPS) is not sold to the general public. The chemical has properties indicating it may be a hazard to the environment. DCDPS is consumed during the formation of the polymer, which means that it is unlikely that there is any unreacted or free DCDPS in final consumer products. DCDPS is considered stable in water (will not degrade in water). DCDPS has been experimentally demonstrated to be not readily biodegradable in soil and sediment (activated sludge). This means it is not easily broken down by bacteria or enzymes in soil and sediment.

The rate constant for the vapor-phase reaction of 4,4'-dichlorophenyl sulfone with photochemically-produced hydroxyl radicals has been estimated as 5.9X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 27 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4,4'-dichlorophenyl sulfone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 4,4'-Dichlorodiphenyl sulfone does not absorb at wavelengths >290(3) and therefore, is not expected to by susceptible to direct photolysis.

An estimated BCF of 200 was calculated for 4,4'-dichlorophenyl sulfone(SRC), using an estimated log Kow of 3.9(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 4,4'-dichlorophenyl sulfone can be estimated to be 7,600(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4,4'-dichlorophenyl sulfone is expected to be immobile in soil.

The Henry's Law constant for 4,4'-dichlorophenyl sulfone is estimated as 1.4X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4,4'-dichlorophenyl sulfone is expected to be essentially nonvolatile from water surfaces(2). 4,4'-dichlorophenyl sulfone is not expected to volatilize from dry soil surfaces(SRC) based upon a an estimated vapor pressure of 8.1X10-7 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to 4,4'-dichlorophenyl sulfone may occur through inhalation and dermal contact with this compound at workplaces where 4,4'-dichlorophenyl sulfone is produced or used. (SRC)

Drug Information

p,p'-Dichlorodiphenyl sulfone is rapidly absorbed from the gut and metabolized by a saturable process. Although some p,p'-dichlorodiphenyl sulfone is eliminated unchanged in feces and urine, most of the elimination is via metabolism. Mathematical modeling of the toxicokinetics supports the view that p,p'-dichlorodiphenyl sulfone induces enzymes involved in its metabolism.|...Adult male F344-rats were injected iv with 10 mg/kg carbon-14 (C14) labeled p,p'-dichlorodiphenyl sulfone (DDS). Other rats were administered 1, 10, or 100 mg/kg C14 labeled DDS orally once or daily for 7 days. Urine and feces samples were collected periodically and analyzed for DDS derived C14 activity. Selected rats were killed 72 hr after single DDS dosing or 72 hr or 2, 3, or 5 weeks after multiple dosing to determine the tissue distribution of DDS derived radioactivity. Attempts were made to identify the urine and fecal DDS metabolites. Iv administered DDS was rapidly distributed to the tissues, the largest amount accumulating in the adipose tissues, where it accumulated for 24 hr, and then was eliminated with an estimated halflife of 12 days. ...On repeat oral dosing at 10 mg/kg, levels of DDS in tissues seemed to reach steady state after approximately 2 weeks, at which time the concentrations in adipose reached 265 ug/g tissue. ...The second largest tissue accumulation of radiolabel occurred in the skin. Orally administered DDS was virtually completely absorbed, with essentially the same tissue distribution occurring as was the case with iv administered DDS. Cumulative urine and fecal excretion of DDS derived C14 activity following iv administration amounted to 13.1 and 20.0% of the dose, respectively. Cumulative urine + fecal C14 excretion following repeated oral dosing with 1, 10, and 100 mg/kg DDS amounted to 30.6, 48.8, and 54.4% of the doses, respectively. More than 90% of the radioactivity that accumulated in the tissues was unchanged DDS.

...Hepatic cytochrome P450 (CYP) content, ethoxyresorufin O-deethylase activities, and levels of metabolites arising from phase I metabolism were doubled after repeat oral administration of p,p'-dichlorodiphenyl sulfone (DDS), but benzphetamine N-demethylase activity was unchanged. Thus, it seems that DDS induces CYP1A forms, but not CYP2B isozymes. DDS-derived radioactivity was excreted primarily in feces and to a lesser extent in urine as a phenolic metabolite and its glucuronide. The aglycone of this glucuronide was isolated and characterized by NMR and MS as 3-hydroxy-4,4'-dichlorodiphenyl sulfone.

... Slow elimination with a half-life of approximately 12 days.

SYMPTOMS: Symptoms of exposure to this compound may include irritation. ACUTE/CHRONIC HAZARDS: This compound may be harmful by ingestion or inhalation. It may cause irritation. When heated to decomposition it emits very toxic fumes of carbon monoxide, carbon dioxide, chlorine, sulfur oxides and hydrogen chloride gas. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

4,4'-dichlorodiphenyl sulfone

4,4'-Dichlorodiphenyl sulfone Use and Manufacturing

Uses

4,4’Dichlorodiphenyl Sulfone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis.


Intermediates


Bis(4-chlorophenyl) sulfone is used as a precursor to prepare 4,4'-diamino-diphenyl sulfone and polysulfone plastics. It is also used to prepare rigid and temperature resistant polymers such as PES or Udel through polymerization with bisphenol-A and bisphenol-S. Further, the udel polymer finds applications in plumbing pipes, printer cartridges and automobile fuses.

Production

10,000,000 - 50,000,000 lb

Plastic material and resin manufacturing|Benzene, 1,1'-sulfonylbis[4-chloro-: ACTIVE|Insecticidal property of bis(p-chlorophenyl)sulfone: Unsymmetrical Deriv was developed for Insecticidal purposes by Stauffer chem.

Computed Properties

Molecular Weight:287.2
XLogP3:3.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:285.9622061
Monoisotopic Mass:285.9622061
Topological Polar Surface Area:42.5
Heavy Atom Count:17
Complexity:306
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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