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Halazone

From Wikipedia, the free encyclopedia
Halazone
Names
Preferred IUPAC name
4-(Dichlorosulfamoyl)benzoic acid
Other names
  • Pantocide
  • p-Sulfondichloramidobenzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.001.140Edit this at Wikidata
EC Number
  • 201-253-1
UNII
UN number1479
  • InChI=1S/C7H5Cl2NO4S/c8-10(9)15(13,14)6-3-1-5(2-4-6)7(11)12/h1-4H,(H,11,12)[1]
    Key: XPDVQPODLRGWPL-UHFFFAOYSA-N[1]
  • C1=CC(=CC=C1C(=O)O)S(=O)(=O)N(Cl)Cl
Properties
C7H5Cl2NO4S
Molar mass270.08 g·mol−1
AppearanceFine white powder with an odor of chlorine[2]
Melting point213 °C (415 °F; 486 K);[3] 196 °C with decomposition.[4]
Less than 1 g/L at 70 °F[2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315,H319
P264,P280,P302+P352,P305+P351+P338,P321,P332+P313,P337+P313,P362
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Halazone (4-(dichlorosulfamoyl)benzoic acid) is achemical compound whoseformula can be written as eitherC
7
H
5
Cl
2
NO
4
S
or(HOOC)(C
6
H
4
)(SO
2
)(NCl
2
)
. It has been widely used to disinfect drinking water.

Other names for this compound includep-sulfondichloramidobenzoic acid,4-[(dichloroamino)sulfonyl]benzoic acid, andPantocide.

Uses

[edit]

Halazone tablets have been used to disinfect water for drinking, especially wheretreated tap water is not available. A typical dosage is 4 mg/L.[5][6]

Halazone tablets were commonly used during World War II by U.S. soldiers forportable water purification, even being included in accessory packs forC-rations until 1945.[7]

Halazone was widely used by Marine infantry units during theVietnam War. Halazone has largely been replaced in that use bysodium dichloroisocyanurate. The primary limitation of halazone tablets was the very short usable life of opened bottles, typically three days or less, unlikeiodine-based tablets which have a usable open bottle life of three months.[citation needed]

Dilute halazone solutions (4 to 8ppm ofavailable chlorine) has also been used to disinfectcontact lenses,[8] and as aspermicide.

Mechanism of action

[edit]

Halazone's disinfecting activity is mainly due to thehypochlorous acid (HClO) released byhydrolysis of thechlorine-nitrogen bonds when the product is dissolved in water:[8]

(R1)(R2)NCl +H
2
O
HOCl +(R1)(R2)NH

The hypochlorous acid is a powerfuloxidizer andchlorinating agent that destroys ordenatures many organic compounds.

Production

[edit]

Halazone can be prepared by chlorination ofp-sulfonamidobenzoic acid.[4]

Another synthesis route is the oxidation ofdichloramine-T withpotassium permanganate in a mild alkaline medium.[4]

See also

[edit]

References

[edit]
  1. ^abPubChem: "Halazone". Accessed on 2018-06-18.
  2. ^abNTP (1992), cited byPubChem
  3. ^Jean-Claude Bradley:Open Melting Point Dataset. Quoted byChemspider.
  4. ^abcSaljoughian, M.; Sadeghi, M. T. (1986). "An improved procedure for the synthesis ofp-(dichlorosulfamoyl)benzoic acid (Halazone)".Monatshefte für Chemie.117 (4): 553.doi:10.1007/BF00810903.
  5. ^Gripo Laboratories: "Water purification range: Halazone USP based Chlorine TabletsArchived 2020-06-27 at theWayback Machine". Product page, accessed on 2018-06-18
  6. ^Precise Health Care PVT LTD: "Halazone tabletsArchived 2021-09-01 at theWayback Machine". Product page, accessed on 2018-06-18
  7. ^Hlavatá, L; Aguilaniu, H; Pichová, A; Nyström, T (2003)."The oncogenic RAS2val19 mutation locks respiration, independently of PKA, in a mode prone to generate ROS".The EMBO Journal.22 (13):3337–3345.doi:10.1093/emboj/cdg314.PMC 165639.PMID 12839995.
  8. ^abRosenthal, Ruth Ann; Schlitzen, Ronald L; McNamee, Linda S; Dassanayake, Nissanake L; Amass, Roger (1992). "Antimicrobial activity of organic chlorine releasing compounds".Journal of the British Contact Lens Association.15 (2): 81.doi:10.1016/0141-7037(92)80044-Z.
Acridine derivatives
Biguanides andamidines
Phenol and derivatives
Nitrofuran derivatives
Iodine products
Quinoline derivatives
Quaternary ammonium compounds
Mercurial products
Silver compounds
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