# US 10,119,085 B2 · Quaternized nitrogen compounds and use thereof as additives in fuels and lubricants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,119,085 B2 - Document ID: US10119085B2 - Status: Granted - Kind: B2 - Application number: 15/918,201 - Filed: 2018-03-12 - Published: 2018-07-19 - Granted: 2018-11-06 - Earliest claimed: 2011-06-28 - Assignees: BASF SE - Applicants: BASF SE - Inventors: Cornelia Roeger-Goepfert; Harald Boehnke; Wolfgang Grabarse; Hannah Maria Koenig; Markus Hansch; Ludwig Voelkel - Web page: https://patentgrep.com/patent/US10119085B2 ## CPC - C10L 1/221: {compounds of uncertain formula; reaction products where mixtures of compounds are obtained} - C10L 1/2383: Polyamines or polyimines, or derivatives thereof {(poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} - C10L 10/04: for minimising corrosion or incrustation - C10L 10/06: for facilitating soot removal - C10L 10/14: for improving low temperature properties - C10M 133/58: Heterocyclic compounds - C10L 2200/0259: Nitrogen containing compounds - C10L 2270/023: for gasoline engines - C10L 2270/026: for diesel engines, e.g. automobiles, stationary, marine - C10M 2215/28: Amides; Imides - C10N 2030/04: Detergent property or dispersant property - C10N 2070/00: Specific manufacturing methods for lubricant compositions - C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS ## Abstract The present invention relates to novel quaternized nitrogen compounds, to the preparation thereof and to the use thereof as a fuel and lubricant additive, more particularly as a detergent additive; to additive packages which comprise these compounds; and to fuels and lubricants thus additized. The present invention further relates to the use of these quaternized nitrogen compounds as a fuel additive for reducing or preventing deposits in the injection systems of direct-injection diesel engines, especially in common-rail injection systems, for reducing the fuel consumption of direct-injection diesel engines, especially of diesel engines with common-rail injection systems, and for minimizing power loss in direct-injection diesel engines, especially in diesel engines with common-rail injection systems. ## Claims ### Claim 1 A fuel composition comprising, in a majority amount of a customary fuel, a proportion of at least one reaction product comprising a quaternized nitrogen compound, or a fraction thereof comprising a quaternized nitrogen compound, and being obtained from said reaction product by purification, said reaction product being obtainable by a) reacting a hydrocarbyl-substituted polycarboxylic acid compound with a compound comprising at least one oxygen or nitrogen group capable of addition or condensation or otherwise reactive, with the polycarboxylic acid, and comprising at least one quaternizable amino group, to obtain a quaternizable hydrocarbyl-substituted polycarboxylic acid compound, and b) subsequent reaction thereof with a quaternizing agent which converts the at least one quaternizable amino group to a quaternary ammonium group, said quaternizing agent being the alkyl ester of a cycloaromatic or cycloaliphatic mono- or polycarboxylic acid, or of an aliphatic polycarboxylic acid; or said reaction product being obtainable by reacting a quaternizable hydrocarbyl-substituted polycarboxylic acid compound comprising at least one quaternizable amino group with a quaternizing agent which converts the at least one quaternizable amino group to a quaternary ammonium group, said quaternizing agent being the alkyl ester of a cycloaromatic or cycloaliphatic mono- or polycarboxylic acid, or of an aliphatic polycarboxylic acid, wherein said compound comprising at least one oxygen or nitrogen group capable of addition or condensation or otherwise reactive, with the polycarboxylic acid, and comprising at least one quaternizable amino group is selected from the group consisting of aromatic or nonaromatic heterocycles having one primary and one tertiary amino group and aromatic or nonaromatic heterocycles having a tertiary amino group and a hydroxyalkyl group. ### Claim 2 (depends on 1) The fuel composition according to claim 1, wherein said aromatic or nonaromatic heterocycles having one primary and one tertiary amino group that is a N-heterocycle which is aminoalkylated on at least one ring nitrogen atom, wherein the N-heterocycle is selected from the group consisting of tetrahydrofuran, pyrrolidine, isoxazolidine, isothiazolidine, pyrazolidine, oxazolidine, thiazolidine, imidazolidine, pyrroline, piperidine, piperidinyl, 1,3-dioxane, tetrahydropyran, hexahydropyridazine, hexahydropyrimidine, piperazine, furan, thiane, pyrrole, pyrazole, oxazole, thiazole, imidazole and 1,3,4-triazole; isoxazole, isothiazole, thiadiazole, oxadiazole, pyridinyl, pyridazine, pyrimidine, pyrazinyl, 1,2,4-triazine, and 1,3,5-triazin-2-yl. ### Claim 3 (depends on 1) The fuel composition according to claim 1, wherein said aromatic or nonaromatic heterocycles having a tertiary amino group and a hydroxyalkyl group is a N-heterocycle which is aminoalkylated on at least one ring nitrogen atom, wherein the N-heterocycle is selected from the group consisting of tetrahydrofuran, pyrrolidine, isoxazolidine, isothiazolidine, pyrazolidine, oxazolidine, thiazolidine, imidazolidine, pyrroline, piperidine, piperidinyl, 1,3-dioxane, tetrahydropyran, hexahydropyridazine, hexahydropyrimidine, piperazine, furan, thiane, pyrrole, pyrazole, oxazole, thiazole, imidazole and 1,3,4-triazole; isoxazole, isothiazole, thiadiazole, oxadiazole, pyridinyl, pyridazine, pyrimidine, pyrazinyl, 1,2,4-triazine, and 1,3,5-triazin-2-yl. ### Claim 4 (depends on 1) The fuel composition according to claim 1, wherein said aromatic or nonaromatic heterocycles having one primary and one tertiary amino group is a N-heterocycles which is aminoalkylated on at least one ring nitrogen atom, wherein the N-heterocycle is selected from the group consisting of furan, thiane, pyrrole, pyrazole, oxazole, thiazole, imidazole and 1,3,4-triazole; isoxazole, isothiazole, thiadiazole, and oxadiazole. ### Claim 5 (depends on 1) The fuel composition according to claim 1, wherein said aromatic or nonaromatic heterocycles having a tertiary amino group and a hydroxyalkyl group is a N-heterocycle which is aminoalkylated on at least one ring nitrogen atom, wherein the N-heterocycle is selected from the group consisting of furan, thiane, pyrrole, pyrazole, oxazole, thiazole, imidazole and 1,3,4-triazole; isoxazole, isothiazole, thiadiazole, and oxadiazole. ### Claim 6 (depends on 1) The fuel composition according to claim 1, wherein said aromatic or nonaromatic heterocycles having one primary and one tertiary amino group is a N-heterocycle which is aminoalkylated on at least one ring nitrogen atom, wherein the N-heterocycle is selected from the group consisting of 1-(3-Aminopropyl)imidazole 4-(3-Aminopropyl)morpholine 1-(2-Aminoethylpiperidine) 2-(1-Piperazinyl)ethylamine (AEP) N-Methylpiperazine ### Claim 7 (depends on 1) The fuel composition according to claim 1, wherein said aromatic or nonaromatic heterocycles having one primary and one tertiary amino group is 1-(3-Aminopropyl)imidazole ### Claim 8 (depends on 1) The fuel composition according to claim 1, wherein said aromatic or nonaromatic heterocycles having a tertiary amino group and a hydroxyalkyl group is 1-(3-Hydroxypropyl)imidazole ### Claim 9 (depends on 7) The fuel composition according to claim 7, wherein about 1.1 to about 2.0 equivalents of quaternizing agent are used per equivalent of quaternizable tertiary nitrogen atom. ### Claim 10 (depends on 1) The fuel composition according to claim 1, wherein the hydrocarbyl-substituted polycarboxylic acid compound is a polyisobutenylsuccinic acid or an anhydride thereof, said acid having a bismaleation level of less than about 20%. ### Claim 11 (depends on 1) The fuel composition according to claim 1, wherein the quaternizing agent is a compound of the general formula 1 R1OC(O)R2 (1) in which R1 is a lower alkyl radical and R2 is an optionally substituted monocyclic aryl or cycloalkyl radical, where the substituent is selected from OH, NH2, NO2, C(O)OR3, and R1OC(O)—, in which R1 is as defined above and R3 is H or R1. ### Claim 12 (depends on 1) The fuel composition according to claim 1, wherein the quaternizing agent is a compound of the general formula 2 R1OC(O)-A-C(O)OR1a (2) in which R1 and R1a are each independently a lower alkyl radical and A is hydrocarbylene, such as especially alkylene or alkenylene. ### Claim 13 (depends on 1) The fuel composition according to claim 1, wherein the quaternizing agent is selected from alkyl salicylates, dialkyl phthalates and dialkyl oxalates. ### Claim 14 (depends on 1) The fuel composition according to claim 1, selected from diesel fuels, biodiesel fuels, gasoline fuels and alkanol-containing gasoline fuels.