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Home > Encyclopedia > 4-Hydroxybenzenesulfonic acid

4-Hydroxybenzenesulfonic acid

4-Hydroxybenzenesulfonic acid structure

4-Hydroxybenzenesulfonic acid 

structure
  • CAS No:

    98-67-9

  • Formula:

    C6H6O4S

  • Chemical Name:

    4-Hydroxybenzenesulfonic acid

  • Synonyms:

    Benzenesulfonic acid,4-hydroxy-;Benzenesulfonic acid,p-hydroxy-;4-Hydroxybenzenesulfonic acid;p-Hydroxybenzenesulfonic acid;p-Phenolsulfonic acid;4-Phenolsulfonic acid;p-Sulfophenol;4-Hydroxyphenylsulfonic acid;NSC 227908

  • Categories:

    Inorganic Chemistry  >  Elementary Substance

Description

yellowish oily liquid


Liquid


4-hydroxybenzenesulfonic acid is an arenesulfonic acid that is phenol substituted by a sulfo group at C-4. It derives from a phenol.

4-Hydroxybenzenesulfonic acid Basic Attributes

174.174

174.17

202-691-6

L74LRO149A

227908

DTXSID1046421

NEEDLES

2908999090

Characteristics

82.98000

-1.67

Liquid

1.337 g/cm3

52 °C

1.615

Soluble in water.

DELIQUESCENT

Safety Information

III

8

UN 2586 8/PG 3

-

R34

S26-S36/37/39-S45

DB6970000

C:Corrosive

Stable. Combustible. Incompatible with strong oxidizing agents.

P280-P305 + P351 + P338-P310

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.

|Danger|H290 (78.45%): May be corrosive to metals [Warning Corrosive to Metals]|P234, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P390, P403+P233, P404, P405, and P501|Aggregated GHS information provided by 238 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

...IRRITATING TO SKIN.

Toxicity

4-Hydroxyphenylsulfonic acid's production and subsequent use mainly as an additive for electroplating baths(1), but also in the manufacture of synthetic tanning agents(1), as a chemical intermediate used to improve the dyeing properties of polyamide fibers(1) or used in the manufacture of polyesters with improved affinity for basic dyes(1), and during its use in the process of granulation of blast furnace slag(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: An estimated Koc of 3.0(1,SRC), based on an estimated log Kow(2,SRC) indicates that 4-hydroxyphenylsulfonic acid will have very high mobility in soil(3,SRC). As this compound is miscible in water(4), leaching may be an important fate process(SRC). In moist soils 4-hydroxyphenylsulfonic acid should quickly dissociate(5,SRC). Biodegradation of this compound may be an important fate process; 4-hydroxyphenylsulfonic acid at 75 ug/l showed complete degradation within 32 days using a soil inoculum(6). 4-Hydroxyphenylsulfonic acid at 100 mg/l was biodegraded by an activated sludge inoculum over 14 days(7). A long lag period of 76-95 hours was measured with complete biodegradation requiring a total of 190 to 195 hours; these results suggested that 4-hydroxyphenylsulfonic acid is biodegraded completely over a long time by acclimatized microorganisms(7). Other aerobic biodegradation experiments using higher concentrations of 4-hydroxyphenylsulfonic acid (500 mg/l) and shorter incubation times (70 hours) determined that 4-hydroxyphenylsulfonic acid was not biodegraded under these conditions(8,9). Under anaerobic conditions, using an aquifer slurry as an inoculum, 4-hydroxyphenylsulfonic acid at 35 mg/l was not biodegraded over a period of 13 months(10). 4-Hydroxyphenylsulfonic acid will not volatilize from moist soil surfaces(SRC) based on an estimated Henry's Law constant of 2.62X10-13 atm-cu/mole(11).|AQUATIC FATE: If released to water, 4-hydroxyphenylsulfonic acid is expected to dissociate(1). Aerobic biodegradation is expected to be a major fate process for 4- hydroxyphenylsulfonic acid. 4-Hydroxyphenylsulfonic acid at 100 mg/l was incubated over 14 days with a non-acclimatized activated sludge inoculum. Complete biodegradation required 190-195 hours including a 76-95 hour lag time; this indicates that an initial acclimatization period prior to biodegradation of this compound is necessary(2). When inoculated with an activated sludge culture which was acclimatized to benzene, 4-hydroxyphenylsulfonic acid, at a concentration of 500 mg/l, was not biodegraded within the time period of 70 hours(3). A pure culture of Pseudomonas H-8, a known benzene sulfonate oxidizer isolated from pond water, was unable to biodegrade 4-hydroxyphenylsulfonic acid over an unreported period of time(4). 4-Hydroxyphenylsulfonic acid at 35 mg/l was not biodegraded under anaerobic conditions for a 13 month period using an aquifer slurry as an inoculum(5). An estimated BCF value of 0 indicates that 4-hydroxyphenylsulfonic acid will not bioconcentrate in an aquatic system(6,7,SRC). 4-Hydroxyphenylsulfonic acid is not expected to volatilize from water surfaces(SRC) based on an estimated Henry's Law constant of 2.62X10-13 atm-cu/mole (8).|ATMOSPHERIC FATE: Based on an estimated vapor pressure of 3.33X10-7 mm Hg at 25 °C(1,SRC), 4-hydroxyphenylsulfonic acid will exist both in the vapor phase and in the particulate phase(2,SRC). In the vapor phase it will degrade fairly rapidly by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 2 days(3,SRC). Particulate phase 4-hydroxyphenylsulfonic acid may be removed physically from air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of 4-hydroxyphenylsulfonic acid with photochemically produced hydroxyl radicals has been estimated to be 7.40X10-12 cu cm/molecule-sec at 25 °C(1,SRC). This corresponds to an atmospheric half-life for 4-hydroxyphenylsulfonic acid of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals/cu cm(1,SRC). Benzenesulfonic acids are strong acids which almost completely dissociate in aqueous solution(2).

A BCF of 0.03 was calculated for 4-hydroxyphenylsulfonic acid, using an estimated log Kow of -1.65(1,SRC) and a recommended regression- derived equation(2,SRC). This BCF value suggests that 4-hydroxyphenylsulfonic acid will not bioconcentrate in aquatic organisms(2).

Based on an estimated log Kow of -1.65(1), the Koc of 4-hydroxyphenylsulfonic acid is estimated as approximately 3.0 using a regression-derived equation(2,SRC). According to a suggested classification scheme, this estimated Koc value suggests that 4-hydroxyphenylsulfonic acid has very high mobility in soil(3).

The Henry's Law constant for 4-hydroxyphenylsulfonic acid is estimated as 2.62X10-13 atm-cu/mole(1,SRC). This indicates that 4-hydroxyphenylsulfonic acid will essentially not volatilize from water surfaces(2).

Drug Information

...IRRITATING TO SKIN.

4-phenolsulfonic acid

4-Hydroxybenzenesulfonic acid Use and Manufacturing

Methods of Manufacturing

PREPN BY HYDROLYSIS OF P-CHLORO- OR P-BROMOBENZENESULFONIC ACID; BY SULFONATION OF PHENOL.|Phenol (25 kg) and 96% sulfuric acid (28 kg) are heated to 50 °C; then 1.25 kg additional sulfuric acid is added and the reaction mixture is heated at 110 °C for 5-6 hours. Reaction water, together with about 5% of the phenol, is distilled off during this period. Yield 95%.

Uses

Intermediates

Production

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS

COMMERCIAL AVAILABLE AS A 65% SOLN.

All other basic organic chemical manufacturing|Benzenesulfonic acid, 4-hydroxy-: ACTIVE|4-Hydroxyphenylsulfonic acid and 2-halogenomalonic esters form the corresponding ethers, which are used in the manufacture of polyesters with improved affinity for basic dyes.

Computed Properties

Molecular Weight:174.18
XLogP3:0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:173.99867984
Monoisotopic Mass:173.99867984
Topological Polar Surface Area:83
Heavy Atom Count:11
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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