Patent GB-959504-A (GB)
Title: Saccharide polydicarboxylate half-esters and their uses
IPC: C10L1/22
Filed: 1962-02-26
Abstract: The invention comprises poly-o-(b -carboxyacyl) saccharides in which the saccharide contains no more than two monosaccharide units and the carboxyacyl group contains at least 10 carbon atoms, or a metal or amine salt, or an ester thereof, and their preparation by treating a saccharide containing no more than two monosaccharide units with a substantial excess of a -b -dicarboxylic acid anhydride containing at least 10 carbon atoms in the presence of a t-amine catalyst.  Simple sugars, sugar alcohols, a - or b -glycoxides and reducing and non-reducing sugars may be used and many are specified. The acid residues are derived from substituted succinic acids i.e. with an alkyl, alkenyl e.g. those resulting from the condensation of olefines, alkyl chlorides or aliphatic alcohols with a -, b -unsaturated acid anhydrides or esters thereof. Compounds specified are glucose and sorbitol bis-(tetrapropenylsuccinate), succose tris- (triisobutenyl succinate) and (oleylsuccinate), sucrose tetrakis-(tetrapropenylsuccinate), -(decylsuccinate), -(isooctylsuccinate), -(n-hexadecylsuccinate), -(succinate from methyloleate-maleic anhydride adduct), sucrose tetradodecenyl tetrakis (tetrapropenyl succinate), and glucose-sucrose (tetra propenylsuccinate) and alkali and amine e.g. 1, 1 dimethyl dodecylamine, 1, 1, diethyl hexadecylamine, or branched amines from the lower olefine polymers, salts and esters therefore. The t-amine catalyst may be trimethyl, triethyl, diethylhexylamines, diethylcyclohexylamines, pyridine and N-ethylpiperidine and is preferably triethylenediamine.  Examples describe the preparation of sucrose penta tetrakis, and bis (tetrapropenyl succinate), sucrose tetrakis (methyl-oleate-maleic anhydride adduct succinate), sucrose tetrakis (n-hexadecenylsuccinate), sucrose tetrakis (dodecenyltetrapropenyl succinate), glucose bis (tetrapropenylsuccinate) glucose/sucrose tetrapropenylsuccinate, and the tallow amine salts of glucose bis (tetrapropenylsuccinate), the benzyl ester of sucrose tris (tetrapropenylsuccinate). The products are used as additives for mineral oils e.g. gasoline, fuel oil, a lubricating oils and improve the combustion, anti-icing, and anti-rust properties thereof.ALSO:Hydrocarbon oil compositions comprise poly-o-(b -carboxyacyl) saccharides in which the saccharide contains no more than two monosaccharide units and the carboxyacyl group contains at least 10 carbon atoms or a metal or amine salt, or ester thereof (see Division C2). The hydrocarbon oil may be gasoline or fuel oil or lubricating oil.  Simple sugars, sugar alcohols, a - and b -glycosides and reducing and non-reducing sugars may be the saccharide, and many are specified, and the acid residues are derived from substituted succinic acids. Compounds specified are glucose and sorbitol bis-(tetrapropenylsuccinate), sucrose tris-(triisobutenyl succinate) and (oleyl succinate), sucrose tetrakis-(tetrapropenylsuccinate), -(decylsuccinate), -(isooctylsuccinate), -(n-hexadecylsuccinate),-(a succinate from methyloleatemaleic anhydride adduct), sucrose tetradodecenyl tetrakis-tetrapropenyl succinate) and glucose - sucrose - (tetrapropenylsuccinate) and alkali and amine, e.g. 1,1-dimethyldodecylamine, 1,1-diethylhexadecylamine, or branched amines from the lower olefine polymers, salts and esters thereof. Amounts of up to 1% of additive may be used or a concentrate of up to 50% of additive may be used for convenient addition.  Examples describe the addition of sucrose penta-(tetrapropenylsuccinate), a sucrose tetra (an adduct of methyl oleate and maleic anhydride succinate), sucrose tetra-(n-hexadecenylsuccinate), to gasoline as an anti-rust and anti-icing agent; tallow amine salts of glucose bis - (tetrapropenylsuccinate), sucrose tetrakis-(tetrapropenylsuccinate) and glucose/sucrose tetrapropenyl succinate as a motor oil detergent; and glucose bis-(tetrapropenylsuccinate) and glucose/sucrose tetrapropenylsucinate and a sucrose tetrakis-(tetrapropenylsuccinate) as anti-rust and anti-icing agents in gasoline.