Patent GB-1098936-A (GB)
Title: Heterocyclic compounds
IPC: F02B3/06
Filed: 1965-04-28
Abstract: Lubricating or hydraulic oil and fuel additives are mono-morpholinone esters of the formula <FORM:1098936/C4-C5/1> or di-morpholinone esters of formula <FORM:1098936/C4-C5/2> or of either of the above formulae except that the R substituent is attached to the carbon atom that is alpha to the other carbonyl group in the acid moiety, where R1 is hydrogen or alkyl of 1 to 8 carbon atoms, R2 is R1 or phenyl, or R1 and R2 together and including the carbon atom to which they are attached, represent a saturated carbocyclic ring of 5 to 7 cyclic carbon atoms which may contain one or more C1 to C4 alkyl substituents, R3 is hydrogen or methyl, Y is oxygen or NR4, R4 is hydrogen, alkyl, or cycloalkyl containing up to 24 carbon atoms, phenyl, naphthyl, or phenylalkyl or alkylphenyl containing up to 8 alkyl carbon atoms, Z is hydrogen, alkyl or cycloalky containing up to 24 carbon atoms, alkylphenyl or phenylalkyl containing up to 8 alkyl carbon atoms, phenyl or naphthyl, x is 1 to 7 and R is an alkenyl or substituted alkenyl radical containing 30 to 200 carbon atoms.  The lubricating compositions may be based on mineral oils having viscosities of 1 to 25 centistokes at 210 DEG  F. or they may be based on synthetic lubricants and may be bodied or gelled for use as greases. Synthetic lubricants include organic esters, polyethers, silicones and phosphate esters.  The fuels to which the additives may be added are gasolines, jet and diesel fuels and furnace oils. Additives such as dithiophosphates, dialkyl dithiophosphates, sulphurized oils, phenols, sulphides, alkyl aryl sulphonates, petroleum sulphonates, polymers and copolymers of unsaturated esters, vinyl heterocyclic nitrogen-containing compounds and hydrocarbons, many being specified alkyl phenol alkylene oxide condensates, silicones, alkyl and aryl phosphates, phenothiazine, amines, alkaline earth alkylphenates and salicylates, calcium phenylstearate, imidazolines and alkenyl-succinic anhydrides reacted with amines and then with boron compounds.ALSO:A compound (A) of Formula I or (B) of Formula II <FORM:1098936/C3/1> <FORM:1098936/C3/2> or (C) of either of the above formulae except that the R substituent is attached to the carbon atom alpha to the other carbonyl group in the acid moiety, where R1 is hydrogen or alkyl of 1 to 8 carbon atoms, R2 is R1 or phenyl, or R1 and R2 together and including the carbon atom to which they are attached, represent a saturated carboxylic ring of 5 to 7 cyclic carbon atoms which may contain one or more C1 to C4 alkyl substituents, R3 is hydrogen or methyl, Y is oxygen or NR4, R4 is hydrogen, alkyl or cycloalkyl each containing up to 24 carbon atoms phenyl, naphthyl and phenylalkyl or alkylphenyl containing up to 8 alkyl carbon atoms, Z is hydrogen, alkyl or cycloalkyl containing up to 24 carbon atoms, phenyl, alkyl-phenyl and phenylalkyl containing up to 8 alkyl carbon atoms and naphthyl, wherein the alkyls may contain thio, hydroxy or tertiary amino groups, x is 1 to 7 and R is an olefine or substituted olefine polymer radical containing 30 to 200 carbon atoms, may be obtained by reacting a polyalkenyl succinic anhydride with a compound III <FORM:1098936/C3/3> The compounds III are morpholinones and when the reaction temperature with the olefinic succinic anhydride is 70 DEG  to 50 DEG  C. a mono morpholinone ester is obtained and when the temperature is 130 DEG  to 250 DEG  C. a dimorpholinone ester is obtained.  To produce a compound of Formula I other than where Y is oxygen and Z is hydrogen, the Formula I mono morpholine ester may be reacted with a compound ZYH such as ammonia, methylamine, ethylene oxide, dibutylaminohexanol and octanol.  The olefinic succinic anhydride is preferably obtained by reacting a polyolefine with maleic anhydride. In the examples the polymers used are polymers of butene, propene, ethylene/isodecene, pentene, isobutylene/styrene and isobutylene/alpha dodecene.