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Methylchloroisothiazolinone

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Methylchloroisothiazolinone
Skeletal formula of methylchloroisothiazolinone
Space-filling model of the methylchloroisothiazolinone molecule
Names
Preferred IUPAC name 5-Chloro-2-methyl-1,2-thiazol-3(2H)-one
Other names 5-Chloro-2-methylisothiazol-3(2H)-one
5-Chloro-2-methyl-4-isothiazolin-3-one
Chloromethylisothiazolinone
Chloromethylisothiazolone
Methylchloroisothiazolinone
Methylchloroisothiazolone
CMI
CMIT
MCI
MCIT
CIT
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1210149
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.043.167 Edit this at Wikidata
EC Number
  • 247-500-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3Key: DHNRXBZYEKSXIM-UHFFFAOYSA-N
  • InChI=1/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3Key: DHNRXBZYEKSXIM-UHFFFAOYAV
SMILES
  • ClC=1SN(C(=O)C=1)C
Properties
Chemical formula C4H4ClNOS
Molar mass 149.59 g·mol
Appearance white solid
Density 1.02 g/cm
Melting point 52 °C (126 °F; 325 K)
Solubility in water Miscible
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Signal word Danger
Hazard statements H300, H301, H310, H311, H314, H317, H330, H331, H335, H410
Precautionary statements P260, P261, P262, P264, P270, P271, P272, P273, P280, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Methylchloroisothiazolinone , also referred to as MCI, is the organic compound with the formula S(C2HCl)C(O)N(CH3). It is a white solid that melts near room temperature. The compound is an isothiazolinone, a class of heterocycles used as biocides. These compounds have an active sulphur moiety that is able to oxidize thiol-containing residues, thereby effectively killing most aerobic and anaerobic bacteria. MCI is often used in combination with methylisothiazolinone, a mixture known as Kathon. The isothiazolinones have attracted attention because they can cause contact dermatitis. Methylchloroisothiazolinone is effective against gram-positive and gram-negative bacteria, yeast, and fungi.

Application

Methylchloroisothiazolinone is found in many water-based personal care products and cosmetics. Methylchloroisothiazolinone was first used in cosmetics in the 1970s. It is also used in glue production, detergents, paints, fuels, and other industrial processes. Methylchloroisothiazolinone is known by the registered tradename Kathon CG when used in combination with methylisothiazolinone.

Methylchloroisothiazolinone may be used in combination with other preservatives including ethylparaben, benzalkonium chloride, bronopol and phenoxyethanol.

Hazards

Methylchloroisothiazolinone can cause allergic reactions in some people. The first publication of the preservative as a contact allergen was in 1988. Cases of photoaggravated allergic contact dermatitis, i.e. worsening of skin lesions after sun exposure, have also been reported.

In pure form or in high concentrations, methylchloroisothiazolinone is a skin and membrane irritant and causes chemical burns. In the United States, maximum authorized concentrations are 15 ppm in rinse-offs (of a mixture in the ratio 3:1 of 5-chloro-2-methylisothiazol 3(2H)-one and 2-methylisothiazol-3 (2H)-one). In Canada, methylchloroisothiazolinone may only be used in rinse-off products in combination with methylisothiazolinone, the total concentration of the combination may not exceed 15 ppm.

Methylisothiazolinone is considered safe in the allowed amount in rinse-off products (0.1%) and safe in leave-in products when formulated to be non-sensitizing.

An overdose of Kathon by aircraft maintenance personnel, using 38 times the correct amount, resulted in damage to both engines of a Titan Airways aircraft in February 2020. After losing both engines in succession, the Airbus A321 made an emergency landing at London Gatwick Airport. The maintenance procedures specified the Kathon to be diluted to 100 PPM by volume, but with the aircraft maintenance technician being unfamiliar with the term "PPM" and the term not being defined in the aircraft maintenance manuals, the technician instead used an online calculator to convert PPM to percentages, misinterpreted the answer, and added 30 kg of Kathon to each wing tank, which was over 38 times the required amount. Over the course of the next day, the Kathon progressively caused more and more damage to the engines, finally resulting in an emergency landing.

References

  1. Silva, Vânia; Silva, Cátia; Soares, Pedro; Garrido, E. Manuela; Borges, Fernanda; Garrido, Jorge (2020). "Isothiazolinone Biocides: Chemistry, Biological, and Toxicity Profiles". Molecules. 25 (4): 991. doi:10.3390/molecules25040991. PMC 7070760. PMID 32102175.
  2. ^ Reinhard; et al. (2001). "Preservation of products with MCI/MI in Switzerland". Contact Dermatitis. 45 (5): 257–264. doi:10.1034/j.1600-0536.2001.450501.x. PMID 11722483. S2CID 21296570.
  3. ^ Knudsen BB, Menne T (1990). "Kathon CG--a new contact sensitizing preservative". Ugeskrift for Lægerer. 152 (10): 656–657. PMID 2321281.
  4. ^ Pirmez, R.; Fernandes, A.L.C.; Melo, M.G.M. (2015). "Photoaggravated contact dermatitis to Kathon CG (methylchloroisothiazolinone/Methylisothiazolinone): A novel pattern of involvement in a growing epidemic?". British Journal of Dermatology. 173 (5): 1343–1344. doi:10.1111/bjd.13986. PMID 26130214. S2CID 37257050.
  5. De Groot, A. C.; Weyland, J. W. (1988). "Kathon CG: A review". Journal of the American Academy of Dermatology. 18 (2 Pt 1): 350–358. doi:10.1016/s0190-9622(88)70051-1. PMID 3279090.
  6. "Annex VI release - 26 November 2017 - 201703" (PDF). U.S. Food and Drug Administration.
  7. "Cosmetic Ingredient Hotlist: Prohibited and Restricted Ingredients". Health Canada. 18 June 2004. Retrieved 15 February 2020.
  8. Burnett, Christina L.; Bergfeld, Wilma F.; Belsito, Donald V.; Cohen, David; Klaassen, Curtis D.; Liebler, Daniel C.; Marks, James G.; Peterson, Lisa A.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.; Heldreth, Bart (2021). "Amended Safety Assessment of Methylisothiazolinone as Used in Cosmetics". International Journal of Toxicology. 40 (1_suppl): 5S–19S. doi:10.1177/10915818211015795. ISSN 1092-874X. PMID 34259065.
  9. Kathon damages aircraft engines
  10. Aviation safety report

External links

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