Patent GB-584196-A (GB)
Title: Improvements in and relating to the manufacture of derivatives of disubstituted methane compounds
IPC: C07F3/14
Filed: 1944-11-17
Abstract: New derivatives of disubstituted methane (D.S.M.) compounds of the general formula R1-CH2-R2, wherein R1 and R2 may b identical or different and chosen from the residues of a phenol-, alkyl phenol-, carboxyl phenol-, benzene-, naphthol-, or alkyl naphthol sulphonic acid, a diphenyl- or alkyl diphenyl-, naphthalene- or alkylnaphthalene-mono- or disulphonic acid, a sulphobenzoic acid, or a nuclear substituted halogen, amino or nitro derivative of any of the aforementioned substances, are obtained by treating such a D.S.M. compound with an organometallic compound of the general formula R3MA, wherein R3 represents an alkyl, aryl, aralkyl or heterocyclic radical optionally substituted with neutral, acidic or basic substituents, M represents a polyvalent metal, preferably mercury or arsenic and A represents an acidic radical such as a halide, nitrate, acetate, or hydroxide or oxide, or (when R3 is basic or contains a basic substituent) an atomic grouping forming with M an acid is radical, reactive with the D.S.M. compound and irrespective of whether the said group is or is not eliminated in the formation of the D.S.M.-organometallic compound.  In general, the organometallic compound R3MA is of basic function, optionally centred on the metal atom.  Reaction is not limited to stoichiometric proportions of the components and pH 4-6.5 is usually advantageous to obtain solutions of such a D.S.M.-organometallic compound in an excess of the same D.S.M. compound or in one or more of the following: Solutions of one or more D.S.M. compounds other than the one used for the preparation of the D.S.M.-organometallic compound or of one or more of the acids R1 or R2, either with or without the addition of one or more mineral acids.  The products have bactericidal, fungicidal, insecticidal medical and pharmaceutical applications. Examples are given of the above methods of reaction.  Bis-(phenol-4-sulphonic acid)-methane is prepared by standing aqueous phenol-4-sulphonic acid with 40 per cent formaldehyde solution, diluting the reaction mass with water and warming to 100 DEG  C.  Specifications 547,564 and 552,751 are referred to.  Samples have been furnished under Sect. 2 (5) of: (a) Malachite green zincichloride, bis-(naphthalene - 2 - sulphonic acid) - methane complex, obtained by reacting malachite green zincichloride with the silver salt of bis-(naphthalene - 2 -sulphonic acid) - methane; (b) bis - (sulphosalicyclic acid)-methane, phenyl mercury complex, obtained by reacting sulphosalicylic acid with 40 per cent formaldehyde and treating the resulting condensation product with ethanolic phenyl mercury acetate; (c) bis-(1-amino-8-hydroxy-3 : 6-naphthalenedisulphonic acid)-methane, phenyl mercury complex, obtained by reacting the condensation product of 1 - amino - 8 - hydroxy - naphthalene - 3 : 6 - disulphonic acid and 40 per cent formaldehyde with ethanolic phenyl mercury acetate; (d) bis-(naphthalene - 2 - sulphonic acid) - methane, benzyl mercury complex, obtained by heating under reflux benzyl mercury chloride, ethanol and silver oxide, and standing the filtrate with bis - (naphthalene - 2 - sulphonic acid) - methane solution.