Patent GB-804305-A (GB)
Title: Fuel oil compositions containing formaldimine salts
IPC: F02B3/06
Filed: 1956-05-01
Abstract: A distillate fuel oil composition contains a formaldimine salt formed by reacting (A) a formaldimine of formula (R1N = CH2)3, where R1 is a normal primary aliphatic hydrocarbon radical containing from 8 to 18 carbon atoms, or a formaldimine of formula R2N = CH2, where R2 is a tertiary alkyl radical containing from 4 to 24 carbon atoms and which is linked to the nitrogen atom through a tertiary carbon atom thereof; with (B) a carboxylic acid, a phenol, a thiophenol, or a thiol.  The trimeric formaldimine may be obtained by condensing formaldehyde with n-octylamine, n-octenylamine, n-decylamine, n-undecylamine, n-dodecenylamine, n-tetradecylamine, n-pentadecylamine, n - hexadecylamine, n - octadecylamine, n - octadecenylamine, n - octadecadienylamine, or mixtures of such amines and amines derived from coconut oil and soybean oil.  The monomeric formaldimine may be obtained by condensing formaldehyde with tertiary butyl amine, tertiary octyl amine, or mixtures of tertiary alkyl primary amines.  The salt may be obtained by reacting the formaldimine with formic, acetic, propionic, caprylic, decanoic, lauric, stearic, oleic, linoleic or abietic acids; benzoic, salicylic, phthalic, diamyl benzoic or wax benzoic acids; phenol, diamylphenol, wax phenol, cresol, catechol, dinonylcatechol, hydroquinone, pyrogallol, wax pyrogallol, or naphthol; thiophenol, thiocresol, thionaphthol, or thioxylenol; ethyl, propyl, octyl, dodecyl, tetradecyl, hexadecyl, octadecyl or octadecenyl thiols; or a tall oil comprising rosin acids and fatty acids.  The composition may contain between 0.001 and 0.05 per cent by weight of the salt.  The fuel oil may have a boiling range between 300 DEG  and 750 DEG  F., and may be a diesel oil or a domestic heating oil containing cracked distillate stocks.  In examples oils contain salts obtained by reacting tall oil with the formaldimine of tertiary butyl primary amine, and by reacting formaldimines of mixtures of amines with oleic acid, with a mixture of phenols, thiophenols and thiols extracted from cracked gasoline, and with a naphthenic acid extracted from crude petroleum.ALSO:Formaldimine salts are formed by reacting (A) a formaldimine of formula (R1N=CH2)3, where R1 is a normal primary aliphatic hydrocarbon radical containing 8 to 18 carbon atoms, or a formaldimine of formula R2N=CH2, where R2 is a tertiary alkyl radical containing 4 to 24 carbon atoms and which is linked to the nitrogen atom through a tertiary carbon atom thereof, with (B) a carboxylic acid, a phenol, a thiophenol or a thiol.  The trimeric formaldimine may be obtained by condensing formaldehyde with n-octylamine, n-octenylamine, n-decylamine, n-undecylamine, n-dodecenylamine, n-tetradecylamine, n-pentadecylamine, n-hexadecylamine, n-octadecylamine, n-octadecenylamine, n-octadecadienylamine, or mixtures of such amines and amines derived from coconut oil and soybean oil.  The monomeric formaldimine may be obtained by condensing formaldehyde with tertiary butylamine, tertiary octylamine, or mixtures of tertiary alkyl primary amines.  The salt may be obtained by reacting the formaldimine with formic, acetic, propionic, caprylic, decanoic, lauric, stearic, oleic, linoleic, naphthenic or abietic acids; benzoic, salicylic, phthalic, diamyl benzoic or wax benzoic acids; phenol, diamylphenol, wax phenol, cresol, catechol, dinonyl - catechol, hydroquinone, pyrogallol, wax pyrogallol, or naphthol; thiophenol, thiocresol, thionaphthol, or thioxylenol; ethyl, propyl, octyl, dodecyl, tetradecyl, hexadecyl, octadecyl, or octadecenyl thiols; or a tall oil comprising rosin acids and fatty acids.  In examples, salts are obtained by reacting tall oil with the formaldimine of tertiary butyl primary amine, and by reacting formaldimines of mixtures of amines with oleic acid, with a mixture of phenols, thiophenols and thiols extracted from cracked gasoline, and with a naphthenic acid extracted from crude petroleum.