Abstract: Secondary or tertiary alkyl phenyl ethers may be induced to undergo thermal rearrangement on alumina, aluminum phosphate, or a silica-modified alumina as catalyst to afford the isomeric ortho-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst with high regioselectivity and good control over the extent of alkylation.

Abstract: Alkylated 5,6,7,8-tetrahydronapthalenols are effective antioxidants for fuel oils. Di- and tri-alkylated tetrahydronaphthalenols are especially effective, with the di- and tri-isopropylated materials being preferred, at a concentration as low as about 5 ppm.

Abstract: Tertiary alkyl phenyl ethers may be induced to undergo thermal rearrangement on an alumina catalyst to afford the isomeric ortho-t-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst. The rearrangement remains regioselective even when the phenyl ring bears an alkoxy group, hence affords a good preparative route to such materials as 2-t-butyl-4-methoxyphenol.

Abstract: Alkyl phenyl ethers may be induced to undergo thermal rearrangement on an alumina catalyst to afford the isomeric ortho-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst. Yields frequently are high with good selectivity.

Abstract: Phenols may be alkylated with monosubstituted or alpha, beta-disubstituted olefins over a silica alumina composite to afford 2,4,6-tri-sec-alkylphenols in high yields. The alkylation catalyst shows high activity and high selectivity to the 2,4,6-trialkylated product while minimizing oligomerization of the olefin. Composites containing from about 40 to about 60% silica, the remainder being alumina, are especially valuable.

Abstract: Substantially improved yields of 2,4,6-trialkylphenols result from alkylating a mixture of phenol and 2,6-dialkylphenol, the latter being a by-product of the alkylation reaction. This results flows from an unexpected synergistic effect accompanying transalkylation. The continuous method of making 2,4,6-trialkylphenol based on this property affords the highly desirable trialkylated phenols in high yield.

Abstract: Alkylated 5,6,7,8-tetrahydronaphthalenols are effective antioxidants for fuel oils, lubricating oils, greases, plastics, and rubbers over a wide temperature range. Di- and tri-alkylated tetrahydronaphthalenols are especially effective, with the di- and tri-isopropylated materials being preferred.

Abstract: A process for introducing a plurality of alkyl groups into the aromatic ring of a hydroxy-substituted aromatic compound comprises contacting said aromatic compound with an olefin in the presence of alumina or halided alumina as catalyst and recovering the product. When said aromatic compound is phenol, said olefin is isobutylene, and said catalyst is fluorided or chlorided alumina, 2,4-di-t-butylphenol is formed with superior selectivity.

Abstract: A process for introducing a plurality of alkyl groups into the aromatic ring of a hydroxy-substituted aromatic compound, whereby the available ortho sites are completely alkylated, comprises contacting said aromatic compound with olefin in the presence of a fluorided alumina as catalyst and recovering the product. The products of the process of this invention possess substantial antioxidant properties. A particular composition which shows enhanced resistance to oxidation and lowered gum formation comprises a major amount of a liquid petroleum product and from about 5 to about 500 parts per million by weight of a polyisopropyl hydroxy aromatic compound in which the available ortho positions are alkylated.

Abstract: A process for introducing a plurality of alkyl groups into the aromatic ring of a hydroxy-substituted aromatic compound comprises contacting said aromatic compound with an olefin in the presence of a lithiated alumina as catalyst and recovering the product. When said aromatic compound is phenol, said olefin is iso-butylene, and said catalyst is lithiated alumina, 2,4-di-t-butylphenol is formed with superior selectivity.