Patent GB-1010536-A (GB)
Title: Organic phosphonic compounds useful as fuel and lubricant additives, and compositions containing organic phosphonic compounds
IPC: C07F9/40
Filed: 1961-12-21
Abstract: A lubricant or fuel composition contains a minor proportion by weight of an oil-soluble alpha - hydrocarbylsulphoxyalkyl phosphous compound of the formula <FORM:1010536/C4-C5/1> wherein R is a hydrocarbyl group having at least 2 carbon atoms, the R1's are the same or different and are selected from hydrogen, hydrocarbyl, and metallic or non-metallic (e.g. amine) cationic radicals and R2 is hydrogen or a C1-C4 alkyl radical.  The lubricant may be a mineral or synthetic hydrocarbon lubricating oil and is preferably of substantially paraffinic and/or naphthenic character and may contain a substantial proportion of aromatic hydrocarbons. Other specified lubricants are di-2-ethylhexyl sebacate and a polyethylene-propylene glycol type lubricant.  The hydrocarbon may be blended with minor proportions of fatty oils such as castor oil or lard oil and/or polymerized olefins, e.g. polyisobutylene. Specified fuels are leaded gasoline and fuel oil.  The oil and fuel compositions may also contain small amounts of alkylated bisphenols having the general formula <FORM:1010536/C4-C5/2> wherein R1 is alkyl, m is 0 or an integer from 1 to 4, at least one m being at least 1, and X is -S-, -S-S-, -Se-, -S-CH2-, -CH2-S-CH2-, -CHR-, -CR2-, -(CH2)n-, -NH, or -O-, R being methyl or ethyl and n being 1, 2 or 3.  The lubricating composition may also contain a partial or full ester of an organic phosphorus acid, e.g. an alkyl, cycloalkyl, aralkyl, aryl, or alkaryl phosphite, phosphate or phosphonate or its thio-derivative, or a P2S5-terpene or P2S5-pine oil reaction product or metal salt thereof.  Reference has been directed by the Comptroller to Specification 795,860.ALSO:The invention comprises an oil-soluble alpha-hydrocarbylsulphoxyalkyl phosphous compound of the formula <FORM:1010536/C2/1> wherein R is a hydrocarbyl group having at least 2 carbon atoms, the R1's are selected from hydrogen, hydrocarbyl and metallic or non-metallic cationic groups and may be the same or different except that they are not both hydrocarbyl groups and R2 is hydrogen or an alkyl radical having 1 to 4 carbon atoms.  They may be obtained by reacting a mercaptan or mercaptide having at least 2 carbon atoms with an appropriate alpha haloalkylphosphous compound, e.g. chloromethylphosphonic acid or its ester or salt derivative in a solvent such as an aqueuos alcoholic solution at reflux temperature and, if desired, in an inert atmosphere and then treating the resulting hydrocarbylmercaptoalkyl phosphous compound with an inorganic acid and an aqueous solution of H2O2 or with a percarboxylic at between 0 DEG  and 100 DEG  C., preferably at room temperature.  Preferably, R2 and at least one of the R1's are hydrogen and preferred compounds are those of the formula <FORM:1010536/C2/2> wherein one of the R1's is hydrogen and the other is a C1-C18 alkyl radical.  When R1 is a cation it may be derived from a primary or secondary amine, e.g. a C8-C30 primary straight chain amine or a branched chain primary aliphatic amine, e.g. a tert.-C8-C24 alkyl amine or a C5-C18 aliphatic secondary amine or it may be a mono- or polyvalent metal, e.g. an alkaline earth metal such as Ca, Ba, Sr or other polyvalent metal, e.g. Zn, Pb, Sn, Cd or Al. The hydrogen peroxide used in the second reaction step is preferably a solution containing between 30 and 50% by weight and suitable inorganic acids for use in this step are HCl, H2SO4 and H3PO4. Specified percarboxylic acids are performic, peracetic, perpropionic, perbutyric acid, mono- and tri-chloroperacetic acid and perbenzoic acid and these may be used as such or formed in situ from H2O2 and the appropriate organic acid.  Examples are given and the products are useful as oil and fuel additives (see Division C5) and as herbicides or insecticides (see Division A5).  Reference has been directed by the Comptroller to Specification 795,860.ALSO:An insecticidal or herbicidal composition contains as active ingredient a compound of the general formula:-  <FORM:1010536/A5-A6/1> wherein R is a hydrocarbyl group having at least 2 carbon atoms, the R1's are selected from hydrogen, hydrocarbyl and metallic or non metallic (e.g. amine) cationic groups and may be the same or different except that they are not both hydrocarbyl groups and R2 is hydrogen or a C1-C4 alkyl radical (see Division C2).  Specified diluents are water and mineral oils and the composition may be in the form of an emulsion.  Reference has been directed by the Comptroller to Specification 795,860.