US3261782A - Alkylbutyrolactone-alpha-acetic acids - Google Patents
Alkylbutyrolactone-alpha-acetic acids Download PDFInfo
- Publication number
- US3261782A US3261782A US349747A US34974764A US3261782A US 3261782 A US3261782 A US 3261782A US 349747 A US349747 A US 349747A US 34974764 A US34974764 A US 34974764A US 3261782 A US3261782 A US 3261782A
- Authority
- US
- United States
- Prior art keywords
- alkylbutyrolactone
- acid
- acetic acids
- engine
- acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
- C10M133/46—Imidazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/04—Well-defined cycloaliphatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/104—Aromatic fractions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/106—Naphthenic fractions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/048—Siloxanes with specific structure containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
Definitions
- This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents.
- the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an or ganic group through an oxygen atom.
- these metal-containing organic compounds have some effectiveness as detergents for dispersing the precursors of deposits Within the oil itself rather than permitting them to form added deposits on the engine parts, they have the disadvantage of forming ash deposits in the engine. These ash deposits lower engine performance by fouling spark plugs and valves, and contribute to preignition.
- alkylbutyrolactone-a-acetic acids are new compounds which are useful as intermediates in the formation of amides of alkylbutyrolactone-u-acetic acid. These amides of alkylbutyrolactone-u-acetic acid are effective as detergents in lubricating oil compositions.
- alkylbutyrolactone-ut-acetic acids described herein are useful not only as intermediates in the formation of metal-free detergents, but these alkylbutyrolactone-a-acetic acids are useful as rust inhibitors in lubricating oil compositions.
- R R and R are hydrogen or alkyl radicals containing a total of from 10 to 300 carbon atoms.
- the total number of carbon atoms in R R and R is preferably from 10 to 100.
- alkyl butyrolactone-a-acetic acids can be prepared by reacting an olefinic hydrocarbon with dimethyl bromosuccinate to obtain the methyl ester which is then converted to the acid.
- the amides of the above-described alkylbutyrolactonea-acetic acid are those derived from ammonia or amines, including aliphatic, cycloaliphatic and aromatic monoamines, polyamines and heterocyclic amines.
- the amino group reacting with the carboxyl groups to form the amide must be a primary or secondary amino group.
- the resulting amides include those of the formula wherein R R and R are the same as defined hereinabove, and R is hydrogen or the residue of an amine radical having from 1 to 20 carbon atoms, preferably from 2 to 12 carbon atoms, and from O to 10 nitrogen atoms.
- lubricating oil additives are the gamma alkylbutyrolactone-u-acetic acids wherein the gamma alkyl radical contains from 10 to 300 carbon alkyl radical containing from 10 to 300 carbon atoms, and atoms; that is, wherein R in the above formula is an R and R are hydrogen.
- Lubricating oils which can be used as base oils when these alkylbutyrolactone-a-acetic acids are used therein include a wide variety of lubricating oils, such as naphthenic base, paraifin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, di-car'boxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fuma
- the above base oils may he used individually or in combinations thereof, wherever miscible or wherever made so by the use of mutual solvents.
- the alkylbutyrolactone-aacetic acids can be used in oils of lubricating viscosity in amounts of 0.1% to 10% by weight, preferably 0.25% to by weight.
- EXAMPLE 1PREPARATION OF THE METHYL ESTER OF POLYBUTENYLBUTYROLACTONE-oc- ACETIC ACID A mixture of 93.8 g. (0.1 mole) of a polybutene (molecular weight of about 840) in 100 ml. heptane, 225 g. (1 mole) of dimethyl bromosuccinate, and 1.46 g. (0.01 mole) of di-t-butyl peroxide was charged to a rocker bomb, and the vessel purged with nitrogen. The reaction mixture was heated at 130 C. with agitation for 5 hours, then cooled to room temperature, and the methyl bromide vented to the atmosphere. The reaction mixture was vacuum distilled to remove the heptane and the unreacted dimethyl bromosuccinate.
- the benzezne and unreacted dimethyl bromosuccinate were removed by distillation at reduced pressure, followed by heating the residual yellow oil for minutes at 195-205 C. at an absolute pressure of 2 mm. Hg.
- the final residue was crystallized from an ether-pentane solvent, resulting in a light brown waxy solid having a melting point range at 3237 C. Infrared analysis of this product showed the spectrum characteristics of a lactone at 1775 cm? and the ester at 1735 CIILTI.
- the lactone acid was then extracted with diethyl ether using ten separate ml. extractions.
- the combined ether extracts were chilled in a Dry Ice-acetone bath.
- the extracts were then filtered to separate the lactone acid in the form of white crystals.
- Infrared analysis of a melt-smear of the white crystals gave the expected peaks of a lactone acid.
- Further recrystallization of the white crystals from ether yielded a sample having a melting point of 104 C., the analysis of which showed a percent carbon of 67.73 and percent hydrogen of 9.68 corresponding to theoretical values of 67.61 and 9.86, respectively.
- lactone acids of the invention are useful themselves as rust inhibitors in lubricating oil compositions in the formulations described above.
- another important feature is their utility as intermediates for reaction with various amines to provide effective nitrogen containing ashless detergents for lubricants.
- EXAMPLE 3 PREPARATION OF TETRAETHYL-ENE PENTAMINE AMIDE OF AN ALKYLBU- TYRLACTONE-u-ACETIC ACID DERIVED FROM A BUTYLENE POLYMER
- An alkylbutyrolactone-a-acetic acid was prepared from a butylene polymer having -a molecular weight of about 850.
- a 40% solution of this lactone in a hydrocarbon oil was reacted with an ethylene amine condensation product having a molecular weight corresponding to tetraethylene pent-amine.
- Infrared analysis showed a band at 1650-1700 cm. due to the amide carbonyl group, and a band at 1775 cm.” due to the butyrolactone carbonyl group.
- Tests B and C are lubricating oil compositions containing 1% by weight of the amide obtained in Example 3 hereinabove in combination with metal dithiophosphates.
- Tests D and E are lubricating oil compositions containing 1.5% of amides derived from triethylene tetramine and diethylene triamine, respectively. The concentration of the dithiophosphates is expressed in millimoles per kilogram of finished composition (based on the metal), that is, mM./kg.
- Dithiophosphate A was a zinc salt of a mixed dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms and the other alkyl radical contained 5 carbon atoms.
- Dithiophosphate B was a zinc dialkylphenyl dithiophosphate.
- the PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
- the GD Nos. refer to the percentage deposits in the piston ring grooves; a 0 evaluation being a clean groove; and a number of being a groove full of deposits.
- the base oils were California SAE 30 base oils.
- Table II hereinbelow presents data obtained in an FL-2 test, using a 6-cylinder Chrysler engine operating at 2500 rpm. for a period of 36 hours, which test is fully described in a Coordinating Research Council bulletin titled Research Technique for the Determination of the Effects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation” (1948).
- the piston varnish rating is a visual observation of the amount of varnish on a piston skirt, with 10 being the maximum rating for a perfectly clean piston, and 0 being the rating of a piston fully covered with black varnish. This piston varnish rating correlates with road performance in automobiles.
- the total rating is the overall deposit rating of the engine, with the rating values ranging from 0, the poorest value, to 100, the top value. These figures indicate the percentage rating for the engine.
- the base oil was an SAE 30 base oil.
- succinirnide and the dithiophosphates were the same as those described for Table I hereinabove.
- the copper strip weight loss was only 15.5 milligrams when using a petroleum base oil containing 6% by weight of the amide prepared as in Example 3 hereinabove.
- Table III hereinbelow presents data obtained in an L38 engine test, using a l-cylinder CLR engine. The test period was for 40 hours.
- R R and R are selected from the group consisting of hydrogen and alkyl radicals having a total of from 10 to 300 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.25% to 5% by weight of an alkylbutyrolactone-aacetic acid of the formula wherein R R and R are selected from the group consisting of hydrogen and alkyl radicals having a total of from 10 to 300 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Description
United States Patent M 3,261,782 ALKYLBUTYROLACTONE-oc-ACETIC ACIDS Donald J. Anderson, San Anselmo, and Louis de Vries,
Richmond, Calif., assignors to Chevron Research Company, a corporation of Delaware No Drawing. Filed Mar. 5, 1964, Ser. No. 349,747 2 Claims. (1. 252-57) This application is a continuation-in-part of Donald J. Anderson and Louis de Vries application Serial No. 259,- 722, filed February 19, 1963 (now abandoned).
This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents.
Present day internal combustion engines operate at high speeds and high compression ratios. When used in the so-called city stop-and-go driving, which includes the greater part of the driving conditions for a large percentage of todays automobiles, the internal combustion engines do not reach the most efficient operating temperature. Under city driving conditions, large amounts of partial oxidation products are formed, and reach the crankcase of the engine by blowing past the piston rings. Most of these partial oxidation products are oil-insoluble, tending to form deposits on the various operating parts of the engine, such as the pistons, piston rings, etc. For the purpose of preventing the deposition of these products on the various engine parts, it is necessary to incorporate detergents in the lubricating oil compositions, thus keeping these polymeric products highly dispersed in a condition unfavorable for deposition on metals.
For the most part, the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an or ganic group through an oxygen atom. Although these metal-containing organic compounds have some effectiveness as detergents for dispersing the precursors of deposits Within the oil itself rather than permitting them to form added deposits on the engine parts, they have the disadvantage of forming ash deposits in the engine. These ash deposits lower engine performance by fouling spark plugs and valves, and contribute to preignition.
It is a particular object of this invention to provide new compounds which are used in the formation of metal-free detergents for lubricating oil compositions.
Therefore, in accordance with this invention, it has been discovered that alkylbutyrolactone-a-acetic acids are new compounds which are useful as intermediates in the formation of amides of alkylbutyrolactone-u-acetic acid. These amides of alkylbutyrolactone-u-acetic acid are effective as detergents in lubricating oil compositions.
The alkylbutyrolactone-ut-acetic acids described herein are useful not only as intermediates in the formation of metal-free detergents, but these alkylbutyrolactone-a-acetic acids are useful as rust inhibitors in lubricating oil compositions.
These acids, which are new compounds, are of the formula o CHCHZCOOH 3,261,782 Patented July 19, 1966 wherein R R and R are hydrogen or alkyl radicals containing a total of from 10 to 300 carbon atoms. The total number of carbon atoms in R R and R is preferably from 10 to 100.
These alkyl butyrolactone-a-acetic acids can be prepared by reacting an olefinic hydrocarbon with dimethyl bromosuccinate to obtain the methyl ester which is then converted to the acid.
The amides of the above-described alkylbutyrolactonea-acetic acid are those derived from ammonia or amines, including aliphatic, cycloaliphatic and aromatic monoamines, polyamines and heterocyclic amines. In any case, the amino group reacting with the carboxyl groups to form the amide must be a primary or secondary amino group.
The resulting amides include those of the formula wherein R R and R are the same as defined hereinabove, and R is hydrogen or the residue of an amine radical having from 1 to 20 carbon atoms, preferably from 2 to 12 carbon atoms, and from O to 10 nitrogen atoms.
Of particular preference as lubricating oil additives are the gamma alkylbutyrolactone-u-acetic acids wherein the gamma alkyl radical contains from 10 to 300 carbon alkyl radical containing from 10 to 300 carbon atoms, and atoms; that is, wherein R in the above formula is an R and R are hydrogen.
Lubricating oils which can be used as base oils when these alkylbutyrolactone-a-acetic acids are used therein include a wide variety of lubricating oils, such as naphthenic base, paraifin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, di-car'boxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, etc.), liquid esters of acids of phosphorus, alkyl benzenes (e.g., monoalkyl benzene such as dodecyl benzene, tetradecyl benzene, etc.) and dia'lkyl benzenes (e.g., n-nonyl-Z-ethylhexy-l benzene), polyphenyls (e.g., 'biphenyls and tenphenyls), alkyl biphenyl ethers, compounds of silicon, e.g., tetraethyl silicate, tetraisopropyl silicate, tetra(4-methyl-2-tetraethyl) silicate, hexyl-(4- methyLZ-pentoxy) disiloxane, poly(-met hyl) siloxane, poly(methylpheny-l) siloxane, etc.
The above base oils may he used individually or in combinations thereof, wherever miscible or wherever made so by the use of mutual solvents.
When used as rust inhibitors the alkylbutyrolactone-aacetic acids can be used in oils of lubricating viscosity in amounts of 0.1% to 10% by weight, preferably 0.25% to by weight.
The preparation of the alkylbutyrolactone-a-acetic acids described herein is illustrated in the following examples.
EXAMPLE 1.PREPARATION OF THE METHYL ESTER OF POLYBUTENYLBUTYROLACTONE-oc- ACETIC ACID A mixture of 93.8 g. (0.1 mole) of a polybutene (molecular weight of about 840) in 100 ml. heptane, 225 g. (1 mole) of dimethyl bromosuccinate, and 1.46 g. (0.01 mole) of di-t-butyl peroxide was charged to a rocker bomb, and the vessel purged with nitrogen. The reaction mixture was heated at 130 C. with agitation for 5 hours, then cooled to room temperature, and the methyl bromide vented to the atmosphere. The reaction mixture was vacuum distilled to remove the heptane and the unreacted dimethyl bromosuccinate.
Infrared analysis of the product showed the spectrum characteristics of the lactone (1780 cmr and the ester (1735 cmf EXAMPLE 2.PR'EPARATION OF THE METHYL ESTER OF DECYLBUTYROLACTONE-oc-ACETIC ACID A mixture of 98.5 g. (0.438 mole) of dimethyl bromosuccinate, 14.7 g. (0.0875 mole) l-dodecene, 1.0 g. (0.00875 mole) of acetyl peroxide in 9 ml. of dimethyl phthalate, and 50' ml. benzene was heated with agitation for 4 hours at 90 C. The benzezne and unreacted dimethyl bromosuccinate were removed by distillation at reduced pressure, followed by heating the residual yellow oil for minutes at 195-205 C. at an absolute pressure of 2 mm. Hg. The final residue was crystallized from an ether-pentane solvent, resulting in a light brown waxy solid having a melting point range at 3237 C. Infrared analysis of this product showed the spectrum characteristics of a lactone at 1775 cm? and the ester at 1735 CIILTI.
Further purification resulted in white crystals which had a melting point of 4345 C. Elemental analysis showed:
Calculated: 68.40% C., 10.14% H. Found: 68.35% C., 8.19% H.
The following equations exemplify the reactions of Example 2:
CH3 CH2 0CH=CH2 BrCHOOCI-Ia CHzCOOCI-Is I CH3(CH2)9CHCH2CI'ICOOCHs 1 Heat CII3(CH2)DGIICH2OI-ICOCOH3 OHtCOOGI-Ia The methyl ester of decylbutyrolactone-a-acetic acid prepared above was converted to the corresponding acid. A mixture of 2 g. of lactone ester, 50 ml. of 96% sulfuric acid and 50 g. of ice were stirred and warmed to 100 C., at which temperature the stirring was continued for about 3 hours. The mixture was cooled until the lactone acid crystallized on top of the sulfuric acid. The lactone acid was then extracted with diethyl ether using ten separate ml. extractions. The combined ether extracts were chilled in a Dry Ice-acetone bath. The extracts were then filtered to separate the lactone acid in the form of white crystals. Infrared analysis of a melt-smear of the white crystals gave the expected peaks of a lactone acid. Further recrystallization of the white crystals from ether yielded a sample having a melting point of 104 C., the analysis of which showed a percent carbon of 67.73 and percent hydrogen of 9.68 corresponding to theoretical values of 67.61 and 9.86, respectively.
The lactone acids of the invention are useful themselves as rust inhibitors in lubricating oil compositions in the formulations described above. However, another important feature is their utility as intermediates for reaction with various amines to provide effective nitrogen containing ashless detergents for lubricants.
The following example illustrates the use of the alkylbutyrolactone-a-acetic acids as intermediates in the formation of the corresponding amides which are effective as detergents in lubricating oil compositions.
EXAMPLE 3.-PREPARATION OF TETRAETHYL- ENE PENTAMINE AMIDE OF AN ALKYLBU- TYRLACTONE-u-ACETIC ACID DERIVED FROM A BUTYLENE POLYMER An alkylbutyrolactone-a-acetic acid was prepared from a butylene polymer having -a molecular weight of about 850. A 40% solution of this lactone in a hydrocarbon oil was reacted with an ethylene amine condensation product having a molecular weight corresponding to tetraethylene pent-amine.
A mixture of 76 g. (0.4 mole) of this tetraethylene pentamine and 1218 g. (0.50 mole) of the the product of the alkylbutyrolactone-a-acetic acid was blended with agitation at 150 C. for one hour, allowed to cool, then stand for 36 hours at room temperature. The mixture 7 was then reheated at 150 C. for 1 hour.
Infrared analysis showed a band at 1650-1700 cm. due to the amide carbonyl group, and a band at 1775 cm." due to the butyrolactone carbonyl group.
Table I hereinbelow presents data obtained with several illustrative tests of derivatives. Tests B and C are lubricating oil compositions containing 1% by weight of the amide obtained in Example 3 hereinabove in combination with metal dithiophosphates. Tests D and E are lubricating oil compositions containing 1.5% of amides derived from triethylene tetramine and diethylene triamine, respectively. The concentration of the dithiophosphates is expressed in millimoles per kilogram of finished composition (based on the metal), that is, mM./kg.
Dithiophosphate A was a zinc salt of a mixed dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms and the other alkyl radical contained 5 carbon atoms. Dithiophosphate B was a zinc dialkylphenyl dithiophosphate.
The test was made in a Caterpillar L1 engine according to Supplement I conditions for a period of 120 hours as described in the Coordinating Research Council Handbook, January, 1946.
The PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
The GD Nos. refer to the percentage deposits in the piston ring grooves; a 0 evaluation being a clean groove; and a number of being a groove full of deposits.
The base oils were California SAE 30 base oils.
1 These te t results were obtained in a Caterpillar L-l te t under the MIL-L2104 conditions. Thus, under the more severe Supplement-1 conditions, these GD Nos. would be considerably higher.
Table II hereinbelow presents data obtained in an FL-2 test, using a 6-cylinder Chevrolet engine operating at 2500 rpm. for a period of 36 hours, which test is fully described in a Coordinating Research Council bulletin titled Research Technique for the Determination of the Effects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation" (1948).
The piston varnish rating is a visual observation of the amount of varnish on a piston skirt, with 10 being the maximum rating for a perfectly clean piston, and 0 being the rating of a piston fully covered with black varnish. This piston varnish rating correlates with road performance in automobiles.
The total rating is the overall deposit rating of the engine, with the rating values ranging from 0, the poorest value, to 100, the top value. These figures indicate the percentage rating for the engine.
The base oil was an SAE 30 base oil.
The succinirnide and the dithiophosphates were the same as those described for Table I hereinabove.
In an L-38 strip corrosion test, the copper strip weight loss was only 15.5 milligrams when using a petroleum base oil containing 6% by weight of the amide prepared as in Example 3 hereinabove.
Table III hereinbelow presents data obtained in an L38 engine test, using a l-cylinder CLR engine. The test period was for 40 hours.
T able III Additive:
Amide (Example 3), wt. percent 2.0 Dithiophosphate A, mM./kg. 10 Dithiophosphate B, mM./kg 2 Test results: Bearing weight loss (mgs) 55.4
wherein R R and R are selected from the group consisting of hydrogen and alkyl radicals having a total of from 10 to 300 carbon atoms.
2. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.25% to 5% by weight of an alkylbutyrolactone-aacetic acid of the formula wherein R R and R are selected from the group consisting of hydrogen and alkyl radicals having a total of from 10 to 300 carbon atoms.
References Cited by the Examiner UNITED STATES PATENTS 6/1958 Nemec 260343.6 11/1964 Prill et al 260343.6
OTHER REFERENCES Kharasch: J our. American Chem. Soc. (1948), pages 1055-1059.
DANIEL E. WYMAN, Primary Examiner.
W. H. CANNON, Assistant Examiner.
Claims (1)
1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR PROPORTION OF AN OIL OF LUBRICATING VISOCITY, AND FROM 0.1% TO 10% BY WEIGHT OF AN ALKYLBUTYROLACTONE-AACETIC ACID OF THE FORMULA
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB6805/64A GB1037985A (en) | 1963-02-19 | 1964-02-18 | Alkylbutyrolactone-ª-acetic acids |
FR964398A FR1383393A (en) | 1963-02-19 | 1964-02-19 | Alkylbutyrolactone-alpha-acetic acids |
US349747A US3261782A (en) | 1963-02-19 | 1964-03-05 | Alkylbutyrolactone-alpha-acetic acids |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25972263A | 1963-02-19 | 1963-02-19 | |
US349747A US3261782A (en) | 1963-02-19 | 1964-03-05 | Alkylbutyrolactone-alpha-acetic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
US3261782A true US3261782A (en) | 1966-07-19 |
Family
ID=26947490
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US349747A Expired - Lifetime US3261782A (en) | 1963-02-19 | 1964-03-05 | Alkylbutyrolactone-alpha-acetic acids |
Country Status (2)
Country | Link |
---|---|
US (1) | US3261782A (en) |
GB (1) | GB1037985A (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4081456A (en) * | 1973-02-28 | 1978-03-28 | Mobil Oil Corporation | Bis-lactam derivatives |
DE2740535A1 (en) * | 1976-09-24 | 1978-03-30 | Exxon Research Engineering Co | HYDROCARBON-SOLUBLE ALKYL LACTONOXAZOLIN, METHOD FOR THE PRODUCTION AND THEIR USE IN HYDROCARBONS AS ANTI-RUST AND / OR SLUDGE DISPERSANT |
US4167514A (en) * | 1976-09-24 | 1979-09-11 | Exxon Research & Engineering Co. | Heterosubstituted alkyl lactone acids, esters and amides |
FR2460300A1 (en) * | 1979-06-28 | 1981-01-23 | Texaco Development Corp | ESTER-LACTONE QUATERNARY AMMONIUM SALTS, PROCESS FOR THEIR PREPARATION AND LUBRICATING OIL COMPOSITIONS CONTAINING THE SAME |
US4302395A (en) * | 1976-09-24 | 1981-11-24 | Exxon Research & Engineering Co. | Lactone oxazolines as oleaginous additives |
US4329286A (en) * | 1975-09-30 | 1982-05-11 | Mobil Oil Corporation | Hydroxyamide acid products and butyrolactone and butyrolactam products |
US4539127A (en) * | 1979-05-04 | 1985-09-03 | Mobil Oil Corporation | Hydroxyamide acid products and butyrolactone and butyrolactam products |
EP0291458A1 (en) * | 1987-05-15 | 1988-11-17 | Ciba-Geigy Ag | Corrosion inhibiting composition |
WO1993003121A1 (en) * | 1991-07-31 | 1993-02-18 | The Lubrizol Corporation | Improved lubricating compositions and additives useful therein |
WO1993022304A1 (en) * | 1992-05-05 | 1993-11-11 | Smithkline Beecham Plc | Phenylderivate as inhibitors of atp citrate lyase |
WO1996028436A1 (en) * | 1995-03-13 | 1996-09-19 | Croda International Plc | Explosive compositions |
GB2303128A (en) * | 1995-03-13 | 1997-02-12 | Croda International Limited | Explosive compositions |
EP0759443A2 (en) * | 1995-08-22 | 1997-02-26 | The Lubrizol Corporation | Hydroxy-substituted monolactones useful as intermediates for preparing lubricating oil and fuel additives |
EP0823471A1 (en) * | 1996-08-08 | 1998-02-11 | The Lubrizol Corporation | Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions and intermediates useful for preparing same |
US5779742A (en) * | 1996-08-08 | 1998-07-14 | The Lubrizol Corporation | Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions |
US6207839B1 (en) | 1996-08-08 | 2001-03-27 | The Lubrizol Corporation | Process for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives |
US6268317B1 (en) * | 1997-10-30 | 2001-07-31 | Matsushita Electric Industrial Co., Ltd. | Working fluid for refrigerating cycle equipment and the refrigerating cycle equipment using the same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2839538A (en) * | 1953-08-26 | 1958-06-17 | Rohm & Haas | Substituted butyrolactones |
US3155685A (en) * | 1960-01-04 | 1964-11-03 | Monsanto Co | Preparation of ester lactones |
-
1964
- 1964-02-18 GB GB6805/64A patent/GB1037985A/en not_active Expired
- 1964-03-05 US US349747A patent/US3261782A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2839538A (en) * | 1953-08-26 | 1958-06-17 | Rohm & Haas | Substituted butyrolactones |
US3155685A (en) * | 1960-01-04 | 1964-11-03 | Monsanto Co | Preparation of ester lactones |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4081456A (en) * | 1973-02-28 | 1978-03-28 | Mobil Oil Corporation | Bis-lactam derivatives |
US4329286A (en) * | 1975-09-30 | 1982-05-11 | Mobil Oil Corporation | Hydroxyamide acid products and butyrolactone and butyrolactam products |
DE2740535A1 (en) * | 1976-09-24 | 1978-03-30 | Exxon Research Engineering Co | HYDROCARBON-SOLUBLE ALKYL LACTONOXAZOLIN, METHOD FOR THE PRODUCTION AND THEIR USE IN HYDROCARBONS AS ANTI-RUST AND / OR SLUDGE DISPERSANT |
US4167514A (en) * | 1976-09-24 | 1979-09-11 | Exxon Research & Engineering Co. | Heterosubstituted alkyl lactone acids, esters and amides |
US4302395A (en) * | 1976-09-24 | 1981-11-24 | Exxon Research & Engineering Co. | Lactone oxazolines as oleaginous additives |
US4539127A (en) * | 1979-05-04 | 1985-09-03 | Mobil Oil Corporation | Hydroxyamide acid products and butyrolactone and butyrolactam products |
FR2460300A1 (en) * | 1979-06-28 | 1981-01-23 | Texaco Development Corp | ESTER-LACTONE QUATERNARY AMMONIUM SALTS, PROCESS FOR THEIR PREPARATION AND LUBRICATING OIL COMPOSITIONS CONTAINING THE SAME |
EP0291458A1 (en) * | 1987-05-15 | 1988-11-17 | Ciba-Geigy Ag | Corrosion inhibiting composition |
WO1993003121A1 (en) * | 1991-07-31 | 1993-02-18 | The Lubrizol Corporation | Improved lubricating compositions and additives useful therein |
WO1993022304A1 (en) * | 1992-05-05 | 1993-11-11 | Smithkline Beecham Plc | Phenylderivate as inhibitors of atp citrate lyase |
US5447954A (en) * | 1992-05-05 | 1995-09-05 | Smithkline Beecham P.L.C. | Phenylderivate as inhibitors of ATP citrate lyase |
GB2303128A (en) * | 1995-03-13 | 1997-02-12 | Croda International Limited | Explosive compositions |
WO1996028436A1 (en) * | 1995-03-13 | 1996-09-19 | Croda International Plc | Explosive compositions |
US5859264A (en) * | 1995-03-13 | 1999-01-12 | Croda International, Plc | Explosive compositions |
GB2303128B (en) * | 1995-03-13 | 1999-01-13 | Croda Int Plc | Explosive compositions |
EP0759443A2 (en) * | 1995-08-22 | 1997-02-26 | The Lubrizol Corporation | Hydroxy-substituted monolactones useful as intermediates for preparing lubricating oil and fuel additives |
EP0759443A3 (en) * | 1995-08-22 | 1998-01-07 | The Lubrizol Corporation | Hydroxy-substituted monolactones useful as intermediates for preparing lubricating oil and fuel additives |
US6020500A (en) * | 1995-08-22 | 2000-02-01 | The Lubrizol Corporation | Hydroxy-substituted monolactones useful as intermediates for preparing lubricating oil and fuel additives |
US6114547A (en) * | 1995-08-22 | 2000-09-05 | The Lubrizol Corporation | Hydroxy-substituted monolactones and use thereof as intermediates for preparing lubricating oil and fuel additives |
EP0823471A1 (en) * | 1996-08-08 | 1998-02-11 | The Lubrizol Corporation | Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions and intermediates useful for preparing same |
US5779742A (en) * | 1996-08-08 | 1998-07-14 | The Lubrizol Corporation | Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions |
US5856279A (en) * | 1996-08-08 | 1999-01-05 | The Lubrizol Corporation | Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions |
US6207839B1 (en) | 1996-08-08 | 2001-03-27 | The Lubrizol Corporation | Process for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives |
US6268317B1 (en) * | 1997-10-30 | 2001-07-31 | Matsushita Electric Industrial Co., Ltd. | Working fluid for refrigerating cycle equipment and the refrigerating cycle equipment using the same |
Also Published As
Publication number | Publication date |
---|---|
GB1037985A (en) | 1966-08-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3018250A (en) | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides | |
US3024195A (en) | Lubricating oil compositions of alkylpiperazine alkenyl succinimides | |
US3018247A (en) | Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends | |
US3361673A (en) | Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine | |
US3261782A (en) | Alkylbutyrolactone-alpha-acetic acids | |
US3185647A (en) | Lubricant composition | |
US3184411A (en) | Lubricants for reducing corrosion | |
US3131150A (en) | Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines | |
US3322670A (en) | Detergent-dispersant lubricant additive having anti-rust and anti-wear properties | |
US3185645A (en) | Oxidation inhibited lubricants | |
US3185704A (en) | Formamide of mono-alkenyl succinimide | |
US3154560A (en) | Nu, nu'-azaalkylene-bis | |
US3449362A (en) | Alkenyl hydrocarbon substituted succinimides of polyamino ureas and their boron-containing derivatives | |
US3216936A (en) | Process of preparing lubricant additives | |
US3184474A (en) | Reaction product of alkenyl succinic acid or anhydride with polyamine and polyhydricmaterial | |
US3288714A (en) | Lubricating oil compositions containing alkenyl succinic anhydrides | |
US3337459A (en) | 2-stroke lubricant | |
US4397750A (en) | N-Hydroxyalkyl pyrrolidinone esters as detergent compositions and lubricants and fuel containing same | |
US3287271A (en) | Combined detergent-corrosion inhibitors | |
US3438899A (en) | Alkenyl succinimide of tris (aminoalkyl) amine | |
US3844958A (en) | Hydrocarbyl amines for lubricating oil detergents | |
US3623985A (en) | Polysuccinimide ashless detergents as lubricating oil additives | |
US3210283A (en) | Lubricant containing alkenyl succinimide and hydroxypolyamine | |
US3200076A (en) | Polypiperazinyl succinimides in lubricating oils | |
US3185643A (en) | Oxidation resistant lubricants |