Standard Oil Company (indiana)

The Standard Oil Company

Richard J Lee

Robert E Karll

Eugene E Richardson

Lynn M Murphy

Delbert H Meyer

Samuel W Harris

Leonard J Baranowski

Darrell M Senneke

Adam S Kurasiewicz

Ortho-quinones with alkyl, olefin polymer, or halogen substituents and a process for the preparation of these compounds comprising a base catalyzed halogen oxidation of alkylated phenol.

1,4,Bis-N,N'-dipolyalkylquinonyl aminopropyl piperazine

This invention relates to improved hydrocarbon lubricating oil compositions. More particularly this invention relates to hydrocarbon oil compositions which possess improved oxidation inhibition properties through the presence of a new additive functioning as an antioxidant or as an antioxidant catalyst which acts as a chain terminating species for oxidation reactions.

Antioxidants and lubricating oil containing same

Cyclic phosphite structure-containing polyalkyl hindered phenol tetramers are disclosed as novel compounds useful to impart to lubricant oils oxidation and corrosion inhibition. A novel preparative method for the cyclic phosphite-containing polyalkyl hindered phenol tetramers is also disclosed wherein at least a molar excess of a tri(C.sub.1 to C.sub.4 alkyl) phosphite is reacted in the presence of iodine as catalyst with a polyalkyl hindered phenol tetramer of the formula: ##STR1## wherein the sum of the carbon atoms in all the R.sub.1, R.sub.2, and R.sub.3 groups is at least 42 and wherein R.sub.1 and R.sub.2 can be C.sub.1 to C.sub.12 alkylhydrocarbon groups and the R.sub.3 groups can each have as many as 200 carbon atoms. The trialkyl phosphite reacts with a pair of adjacent hydroxyl groups to split out 2 molecules of alkanol and form the cyclic phosphite structure: ##STR2## within said tetramer structure. Said R.sub.4 group is the C.sub.1 to C.sub.4 alkyl from the trialkyl phosphite.

Poly-hindered phenol-phosphites and process for preparation

Lubricant antioxidants

Novel zinc N,N'-alkenylsuccinoyl dipyridyl succinate is prepared by the novel reaction between an alkenylsuccinic anhydride, pyridine and zinc catalyzed by zinc chloride in pyridine reaction solvent. The novel zinc salt is useful to inhibit oxidation of hydrocarbon distillates and lubricant oils.

Zinc N,N'-alkenylsuccinoyl dipyridyl succinate as antioxidant

Disclosed are substituted phenol comprising the reaction product of an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, and aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms; and a process for the manufacture of said substituted phenol. The substituted phenol can have the formula ##STR1## where R comprises alkyl substituent containing from about 50 to about 20,000 carbon atoms, and n and r are integers such that n+r.gtoreq.5.ltoreq.15.

Process and compositions

An alkyl-substituted salicylaldehyde whose alkyl-substituent contains at least 6 and up to 2000 or more carbon atoms are novel composition of matter. Said novel alkylsalicylaldehyde can be prepared by the novel reaction of an alkylphenol containing at least six carbon atoms and up to 2000 or more carbon atoms in the phenol's alkyl-substituent, a dialkyloxy methane and a peroxide in the presence of a free radical forming catalyst.

Alkylsalicylaldehyde preparation

Substituted ortho-quinone dimer

Process for selective hydrogenation of aliphatic unsaturated aldehyde to unsaturated alcohol with gaseous hydrogen using supported rhodium-complex catalyst. This invention relates to a process for preparing unsaturated aliphatic alcohols wherein unsaturated aliphatic aldehydes are selectively hydrogenated using supported rhodium-complex catalyst. Unsaturated alcohols have use in the production of plastics and perfumes. Crotonyl alcohol, for example, has utility for the production of copolymers with vinyl acetate or styrene, and also as an intermediate for synthesis of other organic compounds. Allyl alcohol is a precursor for butanediol which is used to produce tetrahydrofuran, polyesters such as polybutylene terephthalate, and polybutylene oxide based polyurethanes. Particular difficulty in selectively hydrogenating alpha, beta unsaturated aldehydes is described in U.S. Pat. No. 3,655,777 (Rylander et al., 1972, assigned to Engelhard Minerals and Chemicals) wherein patentees teach many catalysts, e.g., palladium, platinum, rhodium, ruthenium, and nickel, usually reduce the double bond in preference over reduction of the carbonyl group. Rylander also teaches a high pressure process to obtain unsaturated alcohols using an osmium catalyst.

Rhodium-catalyzed hydrogenation of unsaturated aldehydes to unsaturated

Lubricant additives imparting oxidation inhibiting properties to lubricant compositions, are synthesized by reacting thioxamide, saturated aliphatic aldehyde of from 1 to about 20 carbon atoms, and an olefin of at least 8 carbon atoms, in the presence of a boron trifluoride catalyst.

Oxidation resistant lubricant composition

Substituted ortho-quinones and derivatives

Lubricant compositions containing polymer alkylated aromatic amino acids as antioxidants and a process for the preparation of these amino acids comprising hydrolysis of cyclic keto amides formed from an intramolecular acylation of an imide of an aromatic amine.

Lubricant compositions containing alkylated aromatic amino acid

High molecular weight alkylated phenols, in which the alkyl substituent has an average molecular weight of from about 300 to about 100,000 are nitrosated with nitrous acid anhydride gas, in the presence of an acid catalyst, and the nitrosated product reacted with an amine compound having at least one HN&lt; group to obtain oil-soluble amine derivatives of such nitrosated alkylated phenols suitable as lubricating oil additives having dispersancy properties.

Amine derivatives of nitrosated high molecular weight alkyl-substituted

Dialkylation process for the manufacture of synthetic oils comprising contacting olefin with alkylbenzene in the presence of a borontrifluoride carboxylic acid complex.

Dialkylation of alkylbenzene

Disclosed are processes for making certain compositions, the compositions and lubricating oils containing certain compositions. Disclosed are a substituted phenol comprising the reaction product of an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, and an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms; and a process for the manufacture of said substituted phenol. Also disclosed are oil soluble Mannich reaction products of said substituted phenol, an amine having at least one reactive nitrogen, and a formaldehyde affording reactant; and a process for the manufacture of said Mannich product. Also disclosed is a lubricating oil composition containing said Mannich reaction product.

Growing community of inventors

Downers Grove, IL, United States of America

Richard J Lee