Sulfanilic acid

log Kow = -2.16

-0.9

-2.16

1.485 at 77 °F (NTP, 1992) - Denser than water; will sink

1.485 at 25 °C/4 °C

1.49 g/cm³

1.485 @25 °C

less than 1 mg/mL at 68 °F (NTP, 1992)

Insoluble in ethanol and ether

Soluble in fuming hydrochloric acid

Slowly sol in water: about 1% at 20 °C, about 1.45% at 30 °C, about 1.94% at 40 °C

In water, 10.68 g/L at 20 °C; 14.68 g/L at 30 °C

Solubility in water: poor

When heated to decomposition it emits toxic vapors of /nitrogen oxides and sulfur oxides/.

288 °C

Decomposes without melting at 550 °F (NTP, 1992)

288 °C decomposes without melting

4-aminobenzene sulfonic acid appears as white powder with faint purple tinge. Grayish-white flat crystals. Becomes anhydrous at around 212 °F. Low toxicity (used medicinally).

Dry Powder

Greyish-white solid; [Hawley] White to grey solid; [ICSC] Light grey fine crystals and fragments; [MSDSonline]

WHITE POWDER OR WHITE-TO-GREY CRYSTALS.

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Warning

H315 (98.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Chemical: Benzenesulfonic acid, 4-amino-

Regulation (EC) No 1107/2009 (amended)

Benzenesulfonic acid, 4-amino- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 4-amino- 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: 11-12-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/14240

Benzenesulphonic acid, 4-amino-: Does not have an individual approval but may be used under an appropriate group standard

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.

An eye and mild skin irritant; May cause skin sensitization; In monohydrate form at room temperature; Becomes anhydrous near 100 deg C; [ICSC] Sensitizing in 5 of 6 guinea pig and 1 of 2 mouse skin tests; [IUCLID] Emergency medical treatment: irritants; [HSDB] May cause skin, eye, and mucous membrane irritation; [CAMEO] An irritant; [MSDSonline]

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Sulfanilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Fires involving this compound can be extinguished using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

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.

SLUDGE FROM A MUNICIPAL SEWAGE TREATMENT PLANT WAS ACCLIMATED AS SEED IN A CONTINUOUS FLOW, COMPLETELY MIXED LABORATORY REACTOR. A SUBSTRATE CONTAINING A MIXTURE OF GLUCOSE, PHENOL & SULFANILIC ACID WAS FED AT DIFFERENT FOOD-TO-MICROORGANISM RATIOS. REMOVAL RATE WAS DETERMINED AS TOTAL ORGANIC C (TOC) MEASUREMENTS. ANALYSES FOR EACH SUBSTRATE IN THE INFFLUENT & EFFLUENT SAMPLES WERE MADE.

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 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.

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.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.

WHEN GIVEN ORALLY IN SUFFICIENT AMT (100-500 MG/KG IN RATS), THE CHELATOR /ETHYLENE DIAMINETETRAACETATE/ INCREASES THE RATES OF ABSORPTION OF HEPARIN.../&/ SULFANILIC ACID...ALL LIPID-INSOL SUBSTANCES WHICH ORDINARILY ARE POORLY ABSORBED FROM GI TRACT.

BILE SALTS, DISODIUM EDTA, TETRACYCLINE, OR SODIUM LAURYL SULFATE PRESENT IN THE GUT LUMEN OF THE RAT INCREASED THE TRANSFER OF SULFANILIC ACID FROM THE SMALL INTESTINE TO THE THORACIC DUCT LYMPH.

The effect of mitomycin C (MMC) pre-administration intravenously on the absorption of drugs from rat stomach has been examined by means of the in-situ loop technique. 48 hr after the MMC-treatment, the absorption of salicylic acid, aspirin and sulphanilic acid was not influenced but that of sulphanilamide was significantly increased compared with the control. At 96 hr, a differential effect of MMC on the absorption of each drug was seen: the absorption of weakly acidic drugs was significantly decreased while that of bases and strong sulphonic acid increased. The decreased absorption of salicylic acid and aspirin correlated with the reduced gastric mucosal blood flow. At 96 hr there were severe hemorrhagic lesions in the gastric mucosa. The increase in absorption of poorly absorbed drugs could be ascribed to the increased permeability of the blood-gastric epithelium barrier as was evidenced by leakage of Evans Blue.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that sulfanilic acid is expected to have very high mobility in soil(SRC). The pKa of sulfanilic acid is 3.25 at 25 °C(3), indicating that this compound will partially exist 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 sulfanilic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Sulfanilic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Based on results of the majority of eight separate laboratory determinations, it can be concluded that sulfanilic acid is not readily biodegradable(5). Sulfanilic acid, present at 100 mg/L, reached 8% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(5) which also indicates the compound is not readily biodegradable(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that sulfanilic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.9X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from a log Kow of -2.16(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Sulfanilic acid absorbs UV light at wavelengths >290 nm(6) and may be susceptible to direct photolysis in sunlit water(SRC). Based on results of the majority of eight separate laboratory determinations, it can be concluded that sulfanilic acid is not readily biodegradable(7). Sulfanilic acid, present at 100 mg/L, reached 8% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(8) which also indicates the compound is not readily biodegradable(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfanilic acid, which has an estimated vapor pressure of 1X10-9 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 sulfanilic acid may be removed from the air by wet or dry deposition(SRC). Sulfanilic acid absorbs UV light at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Redness.

Redness. Pain.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of sulfanilic acid can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that sulfanilic acid is expected to have very high mobility in soil. The pKa of sulfanilic acid is 3.25(3), indicating that this compound will partially exist 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).

/HUMAN EXPOSURE STUDIES/ ... Specific and non-specific binding of 4-aminobenzene sulfonic acid to immunoglobulins (lgD) has been detected in patients sensitized to tartrazine from which 4-aminobenzene sulfonic acid can be metabolically liberated. Patients with symptoms of recurrent urticaria have not shown hypersensitivity reactions to 4-aminobenzene sulfonic acid.

/HUMAN EXPOSURE STUDIES/ PATIENTS WITH RECURRENT URTICARIA OR ANGIOEDEMA WERE PROVOKED WITH SULFANILIC ACID. NO URTICARIAL REACTION FROM SULFANILIC ACID WAS NOTED.

AEROBIC: In a study assessing biodegradability by manometric respirometry conducted by the Commission of European Communities, five of the eight laboratories employed in the study determined sulfanilic acid was <20% biodegradable(1). A sixth laboratory where the inoculum was adapted to sulphonic acids found sulfanilic acid to be 70% biodegradable at 10 days and 90% biodegradable at 28 days(1). A seventh laboratory found duplicates on one occasion to give no removal while a single determination yielded 12% degradation(1). The eighth laboratory reported 6, 14 and 62% biodegradation after 28 days in three(1). Based on results of the majority of eight separate laboratory determinations, it can be concluded that sulfanilic acid is not readily biodegradable(1). Sulfanilic acid, present at 100 mg/L, reached 8% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(2) which also indicates the compound is not readily biodegradable(SRC).

An estimated BCF of 3 was calculated in fish for sulfanilic acid(SRC), using a log Kow of -2.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for sulfanilic acid is estimated as 8.9X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that sulfanilic acid is expected to be essentially nonvolatile from water surfaces(2). Sulfanilic acid's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Sulfanilic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(1).

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Sulfanilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Many idiosyncratic non-steroidal anti-inflammatory drugs (NSAIDs) cause GI, liver and bone marrow toxicity in some patients which results in GI bleeding/ulceration/fulminant hepatic failure/hepatitis or agranulocytosis/aplastic anemia. The toxic mechanisms proposed have been reviewed. Evidence is presented showing that idiosyncratic NSAID drugs form prooxidant radicals when metabolized by peroxidases known to be present in these tissues. Thus GSH, NADH and/or ascorbate were cooxidised by catalytic amounts of NSAIDs and hydrogen peroxide in the presence of peroxidase. During GSH and NADH cooxidation, oxygen uptake and activation occurred. Furthermore the formation of NSAID oxidation products was prevented during the cooxidation indicating that the cooxidation involved redox cycling of the first formed NSAID radical product. The order of prooxidant catalytic effectiveness of fenamate and arylacetic acid NSAIDs was mefenamic acid>tolfenamic acid>flufenamic acid, meclofenamic acid or diclofenac. Diphenylamine, a common moiety to all of these NSAIDs was a more active prooxidant for NADH and ascorbate cooxidation than these NSAIDs which suggests that oxidation of the NSAID diphenylamine moiety to a cation and/or nitroxide radical was responsible for the NSAID prooxidant activity. The order of catalytic effectiveness found for sulfonamide derivatives was sulfaphenazole>sulfisoxazole>dapsone>sulfanilic acid>procainamide>sulfamethoxazole>sulfadiazine>sulfadimethoxine whereas sulfanilamide, sulfapyridine or nimesulide had no prooxidant activity. Although indomethacin had little prooxidant activity, its major in vivo metabolite, N-deschlorobenzoyl indomethacin had significant prooxidant activity. Aminoantipyrine the major in vivo metabolite of aminopyrine or dipyrone was also more prooxidant than the parent drugs. It is hypothesized that the NSAID radicals and/or the resulting oxidative stress initiates the cytotoxic processes leading to idiosyncratic toxicity.

4-Aminobenzene sulfonic acid can be absorbed from the gastrointestinal tract. Absorption through the lungs appears to be possible; absorption of an intratracheally-instilled solution of 4- aminobenzene sulfonic acid has been detected in the rat. Accumulation does not take place in mammals; excretion after oral administration mainly occurs within 24 hr. 4-Aminobenzene sulfonic acid is excreted either unchanged or as the N-acetyl metabolite, in the urine in rabbits, and in the urine and the feces in rats.

WHEN SULFANILIC ACID WAS ADMINISTERED ORALLY TO RATS, 53% OF THE ADMINISTERED DOSE WAS FOUND IN THE URINE.

Used to make dyes and other organic chemicals; Also used as an analytical reagent (Ehrlich's reagent and determination of nitrites) and antibacterial; [Merck Index] Used in the paper, pulp, board, and polymer industries; Used as an additive to construction materials and foodstuffs; [IUCLID]

Pulp and Paper Processing [Category: Industry]

Manufacture of various dyes and organic chemicals; as reagent in analytical chemistry (Ehrlich's reagent, determination of nitrites)

Intermediate in the production of dyes, pesticides, pharmaceuticals.

CHEM INT FOR DYES (ESP AZO DYES), EG, C.I. ACID ORANGE 24

CHEM INT FOR ANALGESICS AND OTHER ORG CHEMS

(1979) No Data

(1981) No Data

(1979) 1.11X10+8 GRAMS (INCLUDES SALT)

(1981) 2.55X10+8 GRAMS (INCLUDES SALT)

2023: 7,300,000 lb

(1979) MORE THAN 4.54X10+6 GRAMS (INCL SALT)

(1981) MORE THAN 4.54X10+6 GRAMS (INCL SALT)

Benzenesulfonic acid, 4-amino- 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#5446]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzenesulfonic acid, 4-amino-. Aggregated National Production Volume: 10 to < 50 million pounds.

By heating aniline with weak fuming sulfuric acid and pouring the reaction product into water. /Monohydrate/

Readily prepared from aniline and sulfuric acid.

REACTION OF ANILINE WITH SULFURIC ACID OR SULFUR TRIOXIDE; BAKING OF ANILINE SULFATE TO EFFECT INTRAMOLECULAR REARRANGEMENT

Equimolar amounts of aniline and sulfuric acid are reacted in a lead-lined reactor. The reaction mass is spread on trays and baked in an oven at 190 - 220 °C, the water of the reaction being removed continuously. The process is complete if a sample dissolves clearly in a dilute alkaline solution and has practically no smell of aniline. The crude product is dissolved as a sodium salt in water that has been rendered alkaline with sodium carbonate solution; traces of aniline are removed by blowing with steam. The solution is clarified by filtration and can then be processed further immediately. The baking operation can be carried out in vacuo, which facilitates the removal of the water of the reaction.

Pharmaceutical and Medicine Manufacturing

Benzenesulfonic acid, 4-amino-: ACTIVE

APPLICATION OF 2000 PPM OF A FRUIT THINNING PREPARATION CONTAINING SULFANILIC ACID TO FULLY BLOOMED ORANGE TREES RESULTED IN AN INCREASE IN THINNING RATE FROM 37.6% OF THE CONTROL TO 60.8%.