# US 4,397,750 A · N-Hydroxyalkyl pyrrolidinone esters as detergent compositions and lubricants and fuel containing same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,397,750 A - Document ID: US4397750A - Status: Granted - Kind: A - Application number: 06/291,007 - Filed: 1981-08-07 - Granted: 1983-08-09 - Earliest claimed: 1979-12-17 - Assignees: Mobil Oil Corporation - Inventors: Sheldon Chibnik - Web page: https://patentgrep.com/patent/US4397750A ## CPC - C07D 207/273: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms - C10L 1/232: containing nitrogen in a heterocyclic ring {(C10L1/221 takes precedence)} - 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)} - C10M 133/44: Five-membered ring containing nitrogen and carbon only - C10M 2215/22: Heterocyclic nitrogen compounds - C10M 2215/221: Six-membered rings containing nitrogen and carbon only - C10M 2215/225: the rings containing both nitrogen and oxygen - C10M 2215/226: Morpholines - C10M 2215/30: Heterocyclic compounds - C10M 2217/00: Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions - C10M 2217/02: Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds - C10M 2217/04: Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds - C10N 2040/02: Bearings - C10N 2040/08: Hydraulic fluids, e.g. brake-fluids - C10N 2050/10: semi-solid; greasy - Y02P 20/582: Recycling of unreacted starting or intermediate materials - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - 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 - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract Esters of hydroxyalkylpyrrolidinones and alkenylsuccinic anhydrides are effective detergent additives for hydrocarbyl lubricants and fuels. ## Claims ### Claim 1 A composition comprising a major proportion of a mineral oil of lubricating viscosity synthetic oil of lubricating viscosity, greases prepared from said oils of lubricating viscosity or normally liquid hydrocarbon fuel and a minor amount sufficient to impart detergent and dispersant properties thereto of a hydroxyalkylpyrrolidone ester or polymer thereof wherein said hydroxyalkylpyrrolidinone ester is obtained by reacting, in substantially equimolar amounts, a lactone with a hydroxyamine at a temperature of from about 110.degree. to about 300.degree. C. having the following general formula: NH.sub.2 R(OH)n where R is a hydrocarbyl group having from 1 to about 30 carbon atoms and n is from 1 to about 6 and thereafter esterifying the resulting hydroxyalkylpyrrolidinone product of said reaction with an alkenylsccinic anhydride, at a temperature of from about 110.degree. to about 250.degree. C., wherein the alkenyl group of said succinic anhydride has from about 8 to about 300 carbon atoms, in a molar ratio of from about 1:1 to about 1:10 of said anhydride to said hydroxyalkylpyrrolidinone product. ### Claim 2 (depends on 1) The composition of claim 1 wherein the lactone is selected from the group consisting of .gamma.-butyrolactone, .gamma.-valerolactone and alkyl-, cycloalkyl-, aralkyl- or aryl-substituted butyrolactones. ### Claim 3 (depends on 2) The composition of claim 2 wherein the lactone is .gamma.-butyrolactone. ### Claim 4 (depends on 1) The composition of claim 1 wherein R is C.sub.2 -C.sub.20 alkyl and n is from 1 to 3. ### Claim 5 (depends on 4) The composition of claim 4 wherein the hydroxyamine is selected from the group consisting of 2-aminoethanol, 3-aminoethanol, 2-amino-2-methylpropanol, 2-(2-aminoethoxy)-ethanol, D,L-2-amino-1-propanol, 2-amino-2-ethyl-1,3-propanediol, 2-amino-2-methyl-1,3-propanediol and tris(hydroxymethyl)aminomethane. ### Claim 6 (depends on 4) The composition of claim 4 wherein the hydroxyamine is 2-aminoethanol. ### Claim 7 (depends on 4) The composition of claim 4 wherein the hydroxyamine is 2-amino-2-ethyl-1,3-propanediol. ### Claim 8 (depends on 4) The composition of claim 4 wherein hydroxyamine is tris(hydroxymethyl)aminomethane. ### Claim 9 A compound prepared by (a) reacting under suitable reaction conditions at a temperature of from about 110.degree.-300.degree. C. in substantially equimolar amounts a lactone and a hydroxyamine having the following general formula: NH.sub.2 R(OH)n where R is an alkyl, cycloalkyl or aralkyl group having from 1 to about 30 carbon atoms and n is from 1 to about 6 and thereafter (b) esterifying the resultant hydroxyalkylpyrrolidinone product of reaction (a) at a temperature of from about 110.degree.-250.degree. C. with an alkenyl anhydride wherein the alkenyl group has from about 8 to about 300 carbon atoms in a molar ratio of from about 1:1 to about 1:10 of the pyrrolidinone anhydride to the anhydride. ### Claim 10 (depends on 9) The compound of claim 9 wherein the hydroxyalkylpyrrolidinone is selected from the group consisting of N-(2-hydroxyethyl)-2-pyrrolidinone, N-(1,1-dimethyl-2-hydroxyethyl)-2-pyrrolidinone, N-(3-hydroxypropyl)-2-pyrrolidinone, N-[(2-hydroxyethoxy)ethyl]-2-pyrrolidinone, and N-(1-methyl-2-hydroxyethyl)-2-pyrrolidinone. ### Claim 11 (depends on 9) The compound of claim 9 wherein the alkenyl group is a mixture of olefins containing C.sub.18 to C.sub.24, a dimer thereof or polyisobutylene having a molecular weight of from about 300 to about 3000. ### Claim 12 (depends on 9) The compound of claim 9 wherein the pyrrolidinone is N-(1,-1-dimethyl-2-hydroxyethyl)-2-pyrrolidinone and the alkenyl group is a 900 molecular weight polyisobutylene. ### Claim 13 (depends on 9) The compound of claim 9 wherein the pyrrolidinone is the reaction product of .gamma.-butyrolactone and 2-amino-2-ethyl-1,3-propanediol and the alkenyl group is polyisobutylene having a molecular weight of 1300. ### Claim 14 (depends on 9) The compound of claim 9 wherein the pyrrolidinone is the reaction product of .gamma.-butyrolactone and 2-amino-2-ethyl-1,3-propanediol and the alkenyl group is the dimer of a mixture of olefins containing 18 to 24 carbon atoms. ### Claim 15 A process of preparing a dispersant or detergent additive compound comprising (a) reacting under suitable conditions at a temperature of from about 110.degree.-300.degree. C. in substantially equimolar amounts a lactone with a hydroxyamine having the following general formula: NH.sub.2 R(OH)n where R is alkyl, cycloalkyl, aryl or arylkyl group having from 1 to about 30 carbon atoms and n is from 1 to about 6 and (b) thereafter esterifying the resulting hydroxyalkylpyrrolidinone product of (a) at a temperature of from about 110.degree.-250.degree. C. with an alkenyl anhydride, wherein the alkenyl group has from 8 to 300 carbon atoms in a molar ratio of from about 1:1 to about 1:10 of the pyrrolidinone to the anhydride.