Halazone

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Halazone
Halazone.svg
Names
Preferred IUPAC name
4-(Dichlorosulfamoyl)benzoic acid
Other names
  • Pantocide
  • p-Sulfondichloramidobenzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.140 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-253-1
PubChem CID
UNII
UN number 1479
  • 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 mass 270.08 g·mol−1
AppearanceFine white powder with an odor of chlorine [2]
Melting point 213 °C (415 °F; 486 K); [3] 196 °C with decomposition. [4]
Less than 1 g/L at 70 °F [2]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
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 their standard state (at 25 °C [77 °F], 100 kPa).
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Halazone (4-(dichlorosulfamoyl)benzoic acid) is a chemical compound whose formula can be written as either C
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.

Contents

Other names for this compound include p-sulfondichloramidobenzoic acid, 4-[(dichloroamino)sulfonyl]benzoic acid, and Pantocide.

Uses

Halazone tablets have been used to disinfect water for drinking, especially where treated 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 for portable water purification, even being included in accessory packs for C-rations until 1945. [7]

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

Dilute halazone solutions (4 to 8 ppm of available chlorine) has also been used to disinfect contact lenses, [8] and as a spermicide.

Mechanism of action

Halazone's disinfecting activity is mainly due to the hypochlorous acid (HClO) released by hydrolysis of the chlorine-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 powerful oxidizer and chlorinating agent that destroys or denatures many organic compounds.

Production

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

Another synthesis route is the oxidation of dichloramine-T with potassium permanganate in a mild alkaline medium. [4]

See also

Related Research Articles

<span class="mw-page-title-main">Benzoic acid</span> Organic compound (C6H5COOH)

Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">Chlorine</span> Chemical element with atomic number 17 (Cl)

Chlorine is a chemical element; it has symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite is an alkaline inorganic chemical compound with the formula NaOCl. It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of sodium cations and hypochlorite anions.

Water purification is the process of removing undesirable chemicals, biological contaminants, suspended solids, and gases from water. The goal is to produce water that is fit for specific purposes. Most water is purified and disinfected for human consumption, but water purification may also be carried out for a variety of other purposes, including medical, pharmacological, chemical, and industrial applications. The history of water purification includes a wide variety of methods. The methods used include physical processes such as filtration, sedimentation, and distillation; biological processes such as slow sand filters or biologically active carbon; chemical processes such as flocculation and chlorination; and the use of electromagnetic radiation such as ultraviolet light.

<span class="mw-page-title-main">Chlorine dioxide</span> Chemical compound

Chlorine dioxide is a chemical compound with the formula ClO2 that exists as yellowish-green gas above 11 °C, a reddish-brown liquid between 11 °C and −59 °C, and as bright orange crystals below −59 °C. It is usually handled as an aqueous solution. It is commonly used as a bleach. More recent developments have extended its applications in food processing and as a disinfectant.

<span class="mw-page-title-main">Hypochlorous acid</span> Chemical compound

Hypochlorous acid is an inorganic compound with the chemical formula ClOH, also written as HClO, HOCl, or ClHO. Its structure is H−O−Cl. It is an acid that forms when chlorine dissolves in water, and itself partially dissociates, forming hypochlorite anion, ClO. HClO and ClO are oxidizers, and the primary disinfection agents of chlorine solutions. HClO cannot be isolated from these solutions due to rapid equilibration with its precursor, chlorine.

<span class="mw-page-title-main">Hypochlorite</span> An anion

In chemistry, hypochlorite, or chloroxide is an anion with the chemical formula ClO. It combines with a number of cations to form hypochlorite salts. Common examples include sodium hypochlorite and calcium hypochlorite. The Cl-O distance in ClO is 1.69 Å.

<span class="mw-page-title-main">Nitrogen trichloride</span> Chemical compound

Nitrogen trichloride, also known as trichloramine, is the chemical compound with the formula NCl3. This yellow, oily, and explosive liquid is most commonly encountered as a byproduct of chemical reactions between ammonia-derivatives and chlorine. Alongside monochloramine and dichloramine, trichloramine is responsible for the distinctive 'chlorine smell' associated with swimming pools, where the compound is readily formed as a product from hypochlorous acid reacting with ammonia and other nitrogenous substances in the water, such as urea from urine.

<span class="mw-page-title-main">Sodium chlorate</span> Chemical compound

Sodium chlorate is an inorganic compound with the chemical formula NaClO3. It is a white crystalline powder that is readily soluble in water. It is hygroscopic. It decomposes above 300 °C to release oxygen and leaves sodium chloride. Several hundred million tons are produced annually, mainly for applications in bleaching pulp to produce high brightness paper.

Calcium hypochlorite is an inorganic compound with chemical formula Ca(ClO)2, also written as Ca(OCl)2. It is a white solid, although commercial samples appear yellow. It strongly smells of chlorine, owing to its slow decomposition in moist air. This compound is relatively stable as a solid and solution and has greater available chlorine than sodium hypochlorite. "Pure" samples have 99.2% active chlorine. Given common industrial purity, an active chlorine content of 65-70% is typical. It is the main active ingredient of commercial products called bleaching powder, used for water treatment and as a bleaching agent.

<span class="mw-page-title-main">BCDMH</span> Chemical compound

1-Bromo-3-chloro-5,5-dimethylhydantoin is a chemical structurally related to hydantoin. It is a white crystalline compound with a slight bromine and acetone odor and is insoluble in water, but soluble in acetone.

Salt water chlorination is a process that uses dissolved salt for the chlorination of swimming pools and hot tubs. The chlorine generator uses electrolysis in the presence of dissolved salt to produce chlorine gas or its dissolved forms, hypochlorous acid and sodium hypochlorite, which are already commonly used as sanitizing agents in pools. Hydrogen is produced as byproduct too.

Monochloramine, often called chloramine, is the chemical compound with the formula NH2Cl. Together with dichloramine (NHCl2) and nitrogen trichloride (NCl3), it is one of the three chloramines of ammonia. It is a colorless liquid at its melting point of −66 °C (−87 °F), but it is usually handled as a dilute aqueous solution, in which form it is sometimes used as a disinfectant. Chloramine is too unstable to have its boiling point measured.

<span class="mw-page-title-main">Trichloroisocyanuric acid</span> Chemical compound

Trichloroisocyanuric acid is an organic compound with the formula (C3Cl3N3O3). It is used as an industrial disinfectant, bleaching agent and a reagent in organic synthesis. This white crystalline powder, which has a strong "chlorine odour," is sometimes sold in tablet or granule form for domestic and industrial use.

<span class="mw-page-title-main">Portable water purification</span> Self-contained, easily transported units used to purify water from untreated sources

Portable water purification devices are self-contained, easily transported units used to purify water from untreated sources for drinking purposes. Their main function is to eliminate pathogens, and often also of suspended solids and some unpalatable or toxic compounds.

Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds. Two classes of compounds are considered: inorganic chloramines and organic chloramines. Chloramines are the most widely used members of the halamines.

<span class="mw-page-title-main">Bleach</span> Chemicals used to whiten or disinfect

Bleach is the generic name for any chemical product that is used industrially or domestically to remove colour (whitening) from fabric or fiber or to disinfect after cleaning. It often refers specifically to a dilute solution of sodium hypochlorite, also called "liquid bleach".

<span class="mw-page-title-main">Water chlorination</span> Chorination of water

Water chlorination is the process of adding chlorine or chlorine compounds such as sodium hypochlorite to water. This method is used to kill bacteria, viruses and other microbes in water. In particular, chlorination is used to prevent the spread of waterborne diseases such as cholera, dysentery, and typhoid.

A mixed oxidant solution (MOS) is a type of disinfectant that has many uses including disinfecting, sterilizing, and eliminating pathogenic microorganisms in water. An MOS may have advantages such as a higher disinfecting power, stable residual chlorine in water, elimination of biofilm, and safety. The main components of an MOS are chlorine and its derivatives, which are produced by electrolysis of sodium chloride. It may also contain high amounts of hydroxy radicals, chlorine dioxide, dissolved ozone, hydrogen peroxide and oxygen from which the name "mixed oxidant" is derived.

<span class="mw-page-title-main">Chlorine-releasing compounds</span>

Chlorine-releasing compounds, also known as chlorine base compounds, is jargon to describe certain chlorine-containing substances that are used as disinfectants and bleaches. They include the following chemicals: sodium hypochlorite, chloramine, halazone, and sodium dichloroisocyanurate. They are widely used to disinfect water and medical equipment, and surface areas as well as bleaching materials such as cloth. The presence of organic matter can make them less effective as disinfectants. They come as a liquid solution, or as a powder that is mixed with water before use.

References

  1. 1 2 PubChem: "Halazone". Accessed on 2018-06-18.
  2. 1 2 NTP (1992), cited by PubChem
  3. Jean-Claude Bradley: Open Melting Point Dataset . Quoted by Chemspider.
  4. 1 2 3 Saljoughian, 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 Tablets Archived 2020-06-27 at the Wayback Machine ". Product page, accessed on 2018-06-18
  6. Precise Health Care PVT LTD: "Halazone tablets Archived 2021-09-01 at the Wayback 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. 1 2 Rosenthal, 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.