Benzisothiazolinone

Structural formula
General
Surname	Benzisothiazolinone
other names	1,2-benzothiazol-3-one ( IUPAC ); Benzisothiazolin-3-one; 1,2-Benzisothiazol-3 (2 H ) one; Benzisothiazolone; BIT; Proxan;
Molecular formula	C 7 H 5 NOS
Brief description	light yellow crystalline solid
External identifiers / databases
EC number	220-120-9
ECHA InfoCard	100.018.292
PubChem	17520
ChemSpider	16567
Wikidata	Q411746
properties
Molar mass	151.18 g mol −1
Physical state	firmly
Melting point	154-158 ° C
safety instructions
H and P phrases	H: 302-315-317-318-400
	P: 273-280-305 + 351 + 338
Toxicological data	1020 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benzisothiazolinone belongs to the isothiazolinone class of compounds and is a widely used biocide .

Extraction and presentation

Benzisothiazolinone can be obtained in a multi-stage reaction. Anthranilamide is nitrosated by reaction with a nitrite and then reacted with sulfur dioxide to form 2,2'-dithiodibenzamide . The reaction is difficult to carry out on an industrial scale. As an alternative to this reaction, 2,2'-dithiodibenzamide can be prepared from the corresponding acyl chloride. 2,2'-Dithiodibenzamide is then subjected to an oxidative ring closure. The reaction is carried out under alkaline conditions in the presence of oxygen or an oxygen donor such as e.g. B. carried out a peracid. Alternatively, benzisothiazolinone and its salts can be prepared in good yield by reacting an alkali metal salt or ammonium salt (including mono-, di-, tri- and tetraalkylammonium salts) of the corresponding 2-mercaptobenzamide or free 2-mercaptobenzamide with an oxidizing agent such as aqueous hydrogen peroxide .

Chemical properties

Benzisothiazolinone decomposition products can include carbon monoxide , carbon dioxide , sulfur dioxide , nitrogen oxides, and other toxic gases.

use

Benzisothiazolinone has a microbicidal and fungicidal effect and is used as a preservative in emulsion paints , varnishes, adhesives, detergents, fuels and in paper manufacture . Mixtures with methylisothiazolinone are often used in paints . The dosage is 200 to 400 ppm , depending on the area of application and combination with other biocides . According to a study in Switzerland in 2000, 19% of paints, varnishes and coatings contained benzisothiazolinone. For adhesives, fillers and seals it was 25%.

safety instructions

Benzisothiazolinone is a weak sensitizer. A sensitization may be caused by contained in vinyl gloves BIT. Biocides and cooling lubricants can also cause sensitization.

literature

Wilfried Paulus: Directory of Microbicides for the Protection of Materials and Processes . Springer Netherland, Berlin 2006, ISBN 1-4020-4861-0 .

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on 1,2-benzoisothiazol-3 (2H) -one in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on 1,2-benzisothiazol-3 (2H) -one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry on benzisothiazolinone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ European publication server: PROCESS FOR THE PRODUCTION OF 1,2-BENZISOTHIAZOLIN-3-ON , accessed on August 5, 2018.
↑ E. Reinhard, R. Waeber, M. Niederer, T. Maurer, P. Maly, S. Scherer: Preservation of products with MCI / MI in Switzerland . In: Contact Dermatitis . 2001; 45 (5): 257-64. PMID 11722483 .
↑ J. Geier, Th. Werfel, D. Becker, H. Dickel, M. Fartasch, M. Häberle, U. Hillen, SM. John, V. Mahler, Chr. Skudlik, E. Weisshaar, F. Zagrodnik, TL Diepgen: Effects of occupational contact allergies to methylisothiazolinone (MI), benzisothiazolinone (BIT) and / or octylisothiazolinone (OIT) in BK 5101 . In: Dermatology at work and the environment . tape 60 , no. 1 . Dustri-Verlag, 2012, ISSN 1438-776X , p. 10-17 , doi : 10.5414 / DBX00187 ( abderma.org [PDF]).

[GESTIS-1] Entry on 1,2-benzoisothiazol-3 (2H) -one in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.018.292-2] Entry on 1,2-benzisothiazol-3 (2H) -one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[3] Entry on benzisothiazolinone in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[epo.org-4] European publication server: PROCESS FOR THE PRODUCTION OF 1,2-BENZISOTHIAZOLIN-3-ON , accessed on August 5, 2018.

[5] E. Reinhard, R. Waeber, M. Niederer, T. Maurer, P. Maly, S. Scherer: Preservation of products with MCI / MI in Switzerland . In: Contact Dermatitis . 2001; 45 (5): 257-64. PMID 11722483 .

[6] J. Geier, Th. Werfel, D. Becker, H. Dickel, M. Fartasch, M. Häberle, U. Hillen, SM. John, V. Mahler, Chr. Skudlik, E. Weisshaar, F. Zagrodnik, TL Diepgen: Effects of occupational contact allergies to methylisothiazolinone (MI), benzisothiazolinone (BIT) and / or octylisothiazolinone (OIT) in BK 5101 . In: Dermatology at work and the environment . tape 60 , no. 1 . Dustri-Verlag, 2012, ISSN 1438-776X , p. 10-17 , doi : 10.5414 / DBX00187 ( abderma.org [PDF]).