Halazone

Last updated
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 pictograms GHS-pictogram-exclam.svg
GHS Signal word Warning
H315, H319
P264, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN (what is  Yes check.svgYX mark.svgN ?)
Infobox references

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 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

Benzoic acid Chemical compound

Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates.

Chlorine Chemical element with atomic number 17

Chlorine is a chemical element with the 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 Pauling scale, behind only oxygen and fluorine.

Sodium hypochlorite Chemical compound

Sodium hypochlorite is a chemical compound with the formula NaOCl or NaClO, comprising a sodium cation and a hypochlorite anion. It may also be viewed as the sodium salt of hypochlorous acid. The anhydrous compound is unstable and may decompose explosively. It can be crystallized as a pentahydrate NaOCl·5H
2
O
, a pale greenish-yellow solid which is not explosive and is stable if kept refrigerated.

Water purification Process of removing undesirable chemicals, biological contaminants, suspended solids from water

Water purification is the process of removing undesirable chemicals, biological contaminants, suspended solids, and gases from water. The goal is to produce water 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 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.

Chlorine dioxide 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 an oxidizing agent, able to transfer oxygen to a variety of substrates, while gaining one or more electrons via oxidation-reduction (redox). It does not hydrolyze when it enters water, and is usually handled as a dissolved gas in solution in water. Potential hazards with chlorine dioxide include health concerns, explosiveness and fire ignition. It is commonly used as a bleach.

Disinfectant Antimicrobial agents that inactivate or destroy microorganisms

Disinfectants are chemical agents designed to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than sterilization, which is an extreme physical or chemical process that kills all types of life. Disinfectants are generally distinguished from other antimicrobial agents such as antibiotics, which destroy microorganisms within the body, and antiseptics, which destroy microorganisms on living tissue. Disinfectants are also different from biocides—the latter are intended to destroy all forms of life, not just microorganisms. Disinfectants work by destroying the cell wall of microbes or interfering with their metabolism. It is also a form of decontamination, and can be defined as the process whereby physical or chemical methods are used to reduce the amount of pathogenic microorganisms on a surface.

Hypochlorous acid

Hypochlorous acid (HOCl or HClO) is a weak acid that forms when chlorine dissolves in water, and itself partially dissociates, forming hypochlorite, 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. Sodium hypochlorite (NaClO) and calcium hypochlorite (Ca(ClO)2), are bleaches, deodorants, and disinfectants.

Hypochlorite

In chemistry, hypochlorite is an anion with the chemical formula ClO. It combines with a number of cations to form hypochlorites, which may also be regarded as the salts of hypochlorous acid. Common examples include sodium hypochlorite and calcium hypochlorite.

Nitrogen trichloride

Nitrogen trichloride, also known as trichloramine, is the chemical compound with the formula NCl3. This yellow, oily, pungent-smelling and explosive liquid is most commonly encountered as a byproduct of chemical reactions between ammonia-derivatives and chlorine (for example, in swimming pools). 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.

In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system.

Dichlorine monoxide

Dichlorine monoxide is an inorganic compound with the molecular formula Cl2O. It was first synthesised in 1834 by Antoine Jérôme Balard, who along with Gay-Lussac also determined its composition. In older literature it is often referred to as chlorine monoxide, which can be a source of confusion as that name now refers to the neutral species ClO.

Calcium hypochlorite is an inorganic compound with formula Ca(OCl)2. It is the main active ingredient of commercial products called bleaching powder, chlorine powder, or chlorinated lime, used for water treatment and as a bleaching agent. This compound is relatively stable and has greater available chlorine than sodium hypochlorite (liquid bleach). It is a white solid, although commercial samples appear yellow. It strongly smells of chlorine, owing to its slow decomposition in moist air.

Sodium dichloroisocyanurate

Sodium dichloroisocyanurate is a chemical compound widely used as a cleansing agent and disinfectant. It is a colorless, water-soluble solid. The dihydrate is also known as is the potassium salt. Sanit50™ multipurpose NaDCC tablets are used to disinfect fruits and vegetables, floors and tiles, and all surfaces such as tabletops, door knobs etc.

BCDMH

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.

Monochloramine, often called simply 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.

Portable water purification 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.

Bleach number of chemicals which remove color, whiten, or disinfect, often via oxidation

Bleach is the generic name for any chemical product which is used industrially and domestically to remove color from a fabric or fiber or to clean or to remove stains in a process called bleaching. It often refers, specifically, to a dilute solution of sodium hypochlorite, also called "liquid bleach".

Water chlorination 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.

Mixed oxidant solution is a kind of disinfectant which is used for disinfecting, sterilization and eliminating pathogenic microorganisms in water and in many other applications. Using a mixed oxidant solution for water disinfection (see portable water purification), compared to other methods, such as sodium hypochlorite, Calcium hypochlorite, chlorine gas and ozonation may have various benefits such as higher disinfecting power, stable residual chlorine in water, improved taste and odor, elimination of biofilm and safety. Mixed-oxidant solution is produced by electrolysis of sodium chloride brine (sodium chloride) and is a mixture of disinfecting compounds. The main component of this product is chlorine and its derivatives (ClO, HClO and Cl2 solution). It may also contain high amounts of chlorine dioxide (ClO2) solution, dissolved ozone, hydrogen peroxide(H2O2) and oxygen. This is the reason for calling this solution mixed oxidant.

Chlorine-releasing compounds

Chlorine-releasing compounds, also known as chlorine base compounds, are a family of chemicals that release chlorine. They are widely used to disinfect water, 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". Product page, accessed on 2018-06-18
  6. Precise Health Care PVT LTD: "Halazone tablets". 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.