Benzenesulfonic acid
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Benzenesulfonic acid
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CAS No:
98-11-3
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Formula:
C6H6O3S
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Chemical Name:
Benzenesulfonic acid
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Synonyms:
Benzenesulfonic acid;Phenylsulfonic acid;Besylic acid;Benzenemonosulfonic acid;17-120A;Benzenesulfonic acid (surfactant);BSA;Benzensulfonic acid;BW 70;Alkylbenzenesulfonate;1: PN: WO2020008043 SEQID: 105 claimed sequence;2089288-60-6
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CAS No:
Description
green solid
Deliquescent needles or large plates.|Liquid|GREY-TO-YELLOW HYGROSCOPIC CRYSTALS OR FLAKES WITH PUNGENT ODOUR.
Deliquescent needles or large plates.|Benzenesulfonic acid is the simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group. It is a conjugate acid of a benzenesulfonate.
Benzenesulfonic acid Basic Attributes
158.18
158.18
742513
202-638-7
685928Z18A
1626
2583|2585|1803
DTXSID9024568
FINE, DELIQUESCENT NEEDLES OR LARGE PLATES
29041000
Characteristics
62.8
-1.2
Yellow to light brown Damp Crystalline Solid or Fused Mass
1.3 (47°C)
65 °C
137℃
>230 °F
1.575
H2O: soluble 0.1g/10 mL, clear, colorless
Store below +30°C.
Relative vapour density (air = 1): 5.5
Oral-rat LD50: 980 mg/kg; Oral-Wild Bird LD50: 75 mg/kg
Flammable; burning produces toxic sulfur oxide fumes
WITH 1.5 MOLECULES OF WATER, MP IS 43-44 °C
Slightly soluble in water.
Acids, Strong Oxidizing
Known Catalytic Activity
BENZENESULFONIC ACID reacts with bases and many organic compounds. (NTP, 1992)
Safety Information
III
8
UN 2583 8/PG 2
1
22-34
26-36/37/39-45-36
DB4200000
C
Ventilated, low temperature and dry; stored separately from food materials in warehouse
Stable. Incompatible with strong oxidizing agents, bases, many organic compounds.
P260-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338
H290-H314
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Biodegradation: Benzene sulfonic acid is biodegradable. However, process waste water consisting of mixtures may react differently to bacteria than the pure substances contained in it. It must thus be checked beforehand that the process waste water can be handled by a biological sewage treatment plant, or whether the organic components must be destroyed by wet oxidation or incineration after removing the bulk of the water. Recommendable methods: Incineration, neutralization, discharge to sewer. Peer-review: Neutralize with alkali (care, strong acid) and wash well diluted to sewer. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
Flash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H290 (45.6%): May be corrosive to metals [Warning Corrosive to Metals]|P234, P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P390, P404, P405, and P501|Aggregated GHS information provided by 318 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong 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 material in a refrigerator. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-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. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)|Wear appropriate chemical protective gloves, boots, and goggles.
If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use dry chemical, dry sand, or carbon dioxide. Do not use water on material itself. If large quantities of combustible are involved, use water in flooding quantities as spray and fog.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers.|Personnel protection: Avoid breathing dusts, and fumes from burning material. Avoid bodily contact with the material. Wear appropriate chemical protective gloves, boots, and goggles. If contact with the material anticipated, wear appropriate chemical protective clothing.
Personal protection: face shield, chemical protection suit and particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered plastic containers. Wash away remainder with plenty of water.
Separated from oxidants, bases, metals and food and feedstuffs. Dry. Well closed. Ventilation along the floor.
A harmful concentration of airborne particles can be reached quickly on spraying.
The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion.
NO open flames.
STRICT HYGIENE!
Use ventilation (not if powder), local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
Toxicity
highly toxic
Benzenesulfonic acid's use as a reagent in the manufacture of phenol, resorcinol, and other organic syntheses and as a catalyst(1) could result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(3), benzenesulfonic acid should have very high mobility(SRC) in soil based on estimated Koc values ranging from 1.4 to 12(1,2,SRC). Biodegradation of benzenesulfonic acid is likely to occur in soil media provided adequate acclimation by microorganisms occurs(6). Volatilization of benzenesulfonic acid is not expected from either moist or dry soils(SRC) based on an estimated vapor pressure of approximately 2.36X10-5 mm Hg at 25 °C(4,SRC) and an estimated Henry's Law constant of 2.52X10-9 atm-cu m/mole(5,SRC).|AQUATIC FATE: AQUATIC FATE: Benzenesulfonic acid is expected to be essentially non-volatile from water based upon an estimated Henry's Law constant of 2.52X10-9 atm-cu m/mol(SRC), developed using a fragment constant method(1). Biodegradation of benzenesulfonic acid is likely to occur in aquatic media provided adequate acclimation by microorganisms occurs(2). Aquatic bioconcentration, adsorption to sediment, and hydrolysis are not expected to be important fate processes(SRC).|ATMOSPHERIC FATE: Based on an estimated vapor pressure of approximately 2.36X10-5 mm Hg at 25 °C(1,SRC), benzenesulfonic acid will exist in the atmosphere in the vapor and particulate phases(2). It will degrade in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of 29 days(3). Removal of benzenesulfonic acid from the atmosphere can occur through wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of benzenesulfonic acid with photochemically produced hydroxyl radicals has been estimated to be approximately 5.6X10-13 cu cm/molecule-sec at 25 °C(SRC), using a structure estimation method(1,SRC) This corresponds to an atmospheric half-life of about 29 days at an atmospheric concn of 5X10(+5) hydroxyl radicals per cu cm(1,SRC). The reaction rate constant for the reaction of hydroxyl radicals with benzenesulfonic acid was experimentally determined to be 1.76X10-9 L/mole-sec(2). Photolysis of benzenesulfonic acid in an aqueous solution gave sulfurous acid, SO2 and/or sulfuric acid in a total yield of 38.6%(3). Photolysis of an alkaline solution of benzenesulfonic acid afforded mostly benzene and biphenyl(3). Sulfonic acids are generally resistant to aqueous environmental hydrolysis(4); therefore, benzenesulfonic acid is not expected to hydrolyze in environmental media(SRC). Benzenesulfonic acid had a very strong resistance to ozonation(5).
Based upon an estimated a Log Kow of -2.25(1), the BCF of benzenesulfonic acid can be estimated to be approximately 1.15 from a regression-derived equation(2). This estimated BCF value suggests that bioconcentration of benzenesulfonic acid in aquatic organisms is not expected to be an important fate process(SRC).
Using a structure estimation method based on molecular connectivity indices(1,SRC), the Koc for benzenesulfonic acid can be estimated to be about 12(SRC). The Koc for benzenesulfonic acid can also be estimated to be about 1.4 based on an estimated log Kow of -2.25(3) and a regression derived equation(2). According to a suggested classification scheme(4), these estimated Koc values suggest that benzenesulfonic acid has very high soil mobility.
The Henry's Law constant for benzenesulfonic acid can be estimated to be 2.52X10-9 atm-cu m/mole using a structure estimation method(1). This value of Henry's Law constant indicates that benzenesulfonic acid is essentially non-volatile from water(2).
DRINKING WATER: Benzenesulfonic acid was qualitatively identified in reverse osmosis concentrates of Cincinnati drinking water(1). Benzenesulfonic acid has also been qualitatively identified in drinking water in the U.S. as of 11/25/74 by the U.S. EPA(2).
Occupational exposure to benzenesulfonic acid can occur through dermal contact, inhalation, and ingestion(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 3,164 workers are potentially exposed to benzenesulfonic acid in the USA(1).
Drug Information
...PROBABLY EXCRETED AS BENZENESULFONIC ACID. /FROM TABLE/
BACTERIAL GROWTH ON BENZENESULFONATE ELICITED A CATECHOL 2,3-OXYGENASE, WHICH EFFECTED A META CLEAVAGE OF THE RING. BENZENESULFONATE WAS CATABOLIZED TO ACETALDEHYDE AND PYRUVATE VIA CATECHOL, 2-HYDROXYMUCONIC SEMIALDEHYDE, FORMATE, AND 4-HYDROXY-2-OXOVALERATE.|FORMED FROM ETHYL BENZENESULFONATE IT YIELDS CATECHOL IN PSEUDOMONAS. /FROM TABLE/|Pseudomonas sp strain S-313 converted bezenesulfonic acid to phenol. Experiments with 1802 showed that the hydroxyl group was derived from molecular oxygen
SYMPTOMS: This material causes corrosion of tissues on contact. Coughing burning of eyes and nose and red sores may result. ACUTE/CHRONIC HAZARDS: This chemical is a strong irritant and is corrosive to skin, eyes and mucous membranes. (NTP, 1992)|Corrosives
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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. 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: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. IMMEDIATELY transport the victim to a hospital. 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. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
...GROUP...FREE FROM SERIOUS SYSTEMIC OR CUMULATIVE EFFECTS. ...ANOMALIES IN RELATIONSHIP OF ACID IONIZATION CONSTANTS AND LOCAL DAMAGE TO BODY SURFACES. ...CONTACT WITH HEATED VAPOR OR SUBLIMATES...MAY BE IRRITATION OF UPPER RESP TRACT & EYES & SKIN. /AROMATIC SULFONIC ACIDS/
benzenesulfonate
The substance can be absorbed into the body by inhalation and by ingestion.
Cough. Sore throat. Shortness of breath. Laboured breathing. Burning sensation. Headache. Nausea.
Redness. Burning sensation. Pain. Skin burns.
Redness. Pain. Severe deep burns.
Benzenesulfonic acid Use and Manufacturing
It is obtained by sulfonation with benzene as raw material. Add 2400L of 93% sulfuric acid into the sulfonation pot, and drive benzene into the evaporator at a flow rate of 2500-3000L/h. After evaporation and overheating, superheated benzene vapor with a temperature of 150℃ or higher is formed. The reaction temperature is about 170°C, and the free acid is finally controlled at 4-5%. The reaction is completed after about 10 hours. The unreacted benzene vapor and the generated water vapor are condensed and separated, and the acidic benzene is neutralized by liquid caustic soda and dehydrated by salt for recycling. The benzene sulfonic acid containing benzene is then removed by the vacuum debenzene device to remove residual benzene. The sulfonation yield is 96.5%. Benzene sulfonic acid is neutralized with sodium sulfite or sodium hydroxide to obtain sodium benzene sulfonate. The neutralization yield is 99%. Raw material consumption quota: benzene 600kg/t, oleum 750kg/t.
Examine the ammonium and potassium salts. Determination of zinc. Organic Synthesis. Manufacture of phenol and resorcinol. catalyst. Used as a dehydration catalyst, resin curing agent, and plating additives, but also as a dye intermediate.
Processing aids, not otherwise listed
500,000 - 1,000,000 lb|(1972) AT LEAST 8.2X10+10 GRAMS|(1975) GREATER THAN 4.54X10+5 GRAMS
APPROX 50% AS A CHEM INT FOR PHENOL; & APPROX 50% IN ALL OTHER APPLICATIONS (CHEM INT FOR DYES, ACCELERATOR IN MFR OF ALKYD RESINS, PHENOL-FORMALDEHYDE RESINS, & IN DIOLEFIN POLYMERIZATIONS, & AS CATALYST IN ORG REACTIONS) (1975)
CONCENTRATE, WATER AND METHANOL SOLUTION GRADES /FROM JIM WALTER RESOURCES INC/.
Computer and electronic product manufacturing|Benzenesulfonic acid: ACTIVE|...SULFONAMIDES...ARE ALL DERIVATIVES OF AMIDE OF BENZENESULFONIC ACID...
Health Hazards -> Corrosives|Environmental transformation -> Pesticide transformation products (metabolite, successor)
Benzenesulfonic acid is a known environmental transformation product of Asulam.
Computed Properties
Molecular Weight:158.18
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:158.00376522
Monoisotopic Mass:158.00376522
Topological Polar Surface Area:62.8
Heavy Atom Count:10
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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