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filingDate 1961-08-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1965-05-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-991620-A
titleOfInvention Reacting oximes with nitric oxide and the products of the reaction
abstract N-Nitrosohydroxylamine salts are prepared by reacting in a substantially oxygen-free atmosphere, nitric oxide and a base with an oxime of the formula (A)x-Y = Aryl = NOH where Y is carbon or nitrogen, A is a substituent, x is the valence of Y minus 2, A not being OH when Y is N, and Aryl is a benzene, naphthalene, anthracene or phenanthrene nucleus in its appropriate quinoid form, or a tautomeric precursor of said oxime, the reaction involving at least one equivalent of base and at least one equivalent of nitric oxide. Aryl may be substituted, e.g. by chlorine, nitro or alkyl. The invention also comprises as new compounds salts of the formula <FORM:0991620/C2/1> where M is a cation and the residual N valence is linked to a radical containing from 1 to 18 carbon atoms, having from 0 to 2 substituents selected from chloro, nitro and carboxy groups, and terminating in one of the elements C, N, O and S, and also para-(arylcarbyl)aryl-N-nitroso hydroxylamine salts, i.e. salts having the moity <FORM:0991620/C2/2> the nature of Z not being shown, but possibly indicating a dimer, said salts being the product of reaction of nitric oxide and a base with a methylene quinone oxime, i.e. >C = Aryl = NOH, wherein the methylene carbon atom is substituted by electron-withdrawing radicals at least one of which is an aryl radical containing up to 18 carbon atoms and having from 1 to 3 benzenoid rings and from 0 to 2 substituents selected from chloro, nitro, alkoxy, carboxy and C1- 5 alkyl. A in the starting materials of type A-N = Aryl = N-OH (quinone oxime imines) may represent H2NCONH-, H2NCSNH-, -NHCONH- or -NHCSNH-linking two quinone oxime imine groups, mercapto and organomercapto, nitrile, amino, substituted amino, an ether group, an acyl group derived from a carboxylic or sulphonic acid, organosulphonyl, organosulphinyl, and organic radicals terminated by carbon (including unsubstituted or substituted acyclic, carbocyclic and heterocyclic radicals). Where A is a group terminated by carbon sulphur the starting materials may be used in the form of their tautomeric N-nitroso compounds A-NH-Aryl-NO. A1 and/or A11 in starting materials of the type <FORM:0991620/C2/3> may be an unsubstituted or substituted aryl radical or a strongly electron-withdrawing radical such as cyano, nitro, carboxylic acid, salt or ester, or a sulphonyl group. Suitable bases for conducting the reaction include alkali hydroxides, alkali metal alkoxides and organic bases. Salts of other metals may be obtained by metathesis. Aqueous or organic solutions may be used. Reaction temperatures are not generally above 100 DEG C. and may be below 0 DEG C. The products may be used for vulcanizing polychloroprene, as rubber cure accelerators, chelating agents, fuel additives, indicator dyes, explosives, corrosion inhibitors and pesticides.
priorityDate 1959-12-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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