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Process for producing alkylated hydroxyl-containing aromatic compounds
| Details |
Inventors: Campbell, Curtis Bay; Le Coent, Jean Louis;
Assignee: Chevron Oronite Company, LLC (San Francisco, CA); Chevron Oronite S.A. (Levallois-Perret, FR)
Primary Examiner: Shippen; Michael L.
Assistant Examiner:
Attorney, Agent or Firm: Sheridan; Richard J., Jones; Josetta I., Fallon; Martin C.
An alkylated hydroxyl-containing aromatic compound is produced by isomerizing a normal alpha-olefin having from about 16 to about 30 carbon atoms in the presence of a first solid, acidic catalyst capable of inducing both olefin isomerization and skeletal isomerization to produce a mixture of isomerized olefin, then alkylating an hydroxyl-containing aromatic compound with the mixture of isomerized olefins in the presence of a second solid, acidic catalyst. The first solid, acidic catalyst can be SM-3, MAPO-11, SAPO-11, SSZ-32, ZSM-23, MAPO-39, SAPO-39, ZSM-22, SSZ-20, ZSM-35, SUZ-4, NU-23, NU-87, natural ferrierite or synthetic ferrierite. The second solid, acidic catalyst can be a sulfonic acid anionic ion exchange resin catalyst or an acidic clay. |
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DETAILED DESCRIPTION OF THE INVENTION In its broadest aspect, the present invention involves a process for producing alkylated aromatic compounds that have at least one hydroxyl and at least one alkyl group on the same aromatic ring.
That process comprises isomerizing a normal alpha-olefin or mixture of normal alpha-olefins (referred to herein collectively as "NAO") having from about 16 to about 30 carbon atoms in the presence of a first solid, acidic catalyst capable of inducing both olefin isomerization and skeletal isomerization to produce a mixture of isomerized olefins, then alkylating an aromatic compound having at least one hydroxyl group on the aromatic ring with the mixture of isomerized olefins in the presence of a second solid, acidic catalyst comprising a sulfonic acid resin catalyst or an acidic clay.
The alkylation of phenol with olefins, under normal alkylation conditions using a macroporous sulfonic acid resin catalyst or acidic clay, nominally affords an alkylated phenol product in which the para and ortho isomers are dominant.
When one uses a normal alpha-olefin to alkylate the phenol, the para isomer/ortho isomer ratio content is only about 50/50.
It has now been discovered that by isomerizing an NAO prior to using it to alkylate phenol (or other hydroxyl-containing aromatic compounds), a significant increase in the para isomer is obtained in the alkylated product, e.
g.
, the para isomer/ortho isomer ratio can be increased to about 80/20.
The alkylated product can be used to prepare detergents for lubricating oil, and the high para-isomer content allows more base to be added to the detergent.
AROMATIC COMPOUNDS CONTAINING AT LEAST ONE HYDROXYL GROUP ON THE AROMATIC RING The hydroxyl-containing aromatic compounds that are alkylated in the subject process include phenol, catechol, anisole, cresol, resorcinol and mixtures thereof, with phenol being the preferred compound.
NORMAL ALPHA-OLEFINS The normal alpha-olefins that are isomerized prior to the alkylation of the hydroxyl-containing aromatic compounds are normal alpha-olefins or mixtures of normal alpha-olefins that have from about 16 to about 30 carbon atoms per molecule
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