Alkoxylation of cresylic acids
AssigneeConoco Inc.
InventorsGerald L. Nield, Kang Yang, Paul H. Washecheck
Life of this patent
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Abstract
Cresylic acid ethoxylation is catalyzed by basic compounds and salts of alkaline earth metals. Ethoxylates from such reactions have narrow ethylene oxide distributions, lower pour points and lower by-products as compared to alkali base catalyzed ethoxylation. Suitable catalysts include strontium-containing and barium-containing materials. The catalyst also includes co-catalyst combinations using these materials with one or more promoters including polyols, amines, amides, carboxylic acids and phenols. The co-catalyst combinations can be preformed prior to introduction into the reaction mixture.
Claims10
A method for the alkoxylation of cresylic acids containing from about 6 to about 36 carbon atoms comprising contacting said cresylic acids with an alkoxylating agent at temperatures from about 120.degree. C. to about 260.degree. C. in the presence of basic barium-containing and strontium-containing materials selected from the group consisting of strontium metal, barium metal, strontium hydride, barium hydride, strontium oxide, barium oxide, strontium hydroxide, barium hydroxide, strontium hydroxide.XH.sub.2 O and barium hydroxide.XH.sub.2 O wherein X represents the number of water molecules present, and wherein the cresylic acids are a phenolic compound or a mixture of phenolic compounds having the general formula ##STR9## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, substituted aryl groups, halogen, hydroxyl, nitro, or carbonyl and wherein in addition the R-designated groups can contain one or more functionalities selected from the group consisting of halogen, nitro, carboxyl, carbonyl, amine, amide, or hydroxyl and wherein in addition from about 0.1 to about 2.0 weight percent by weight based on the weight of cresylic acid of a catalyst promoter or mixture of catalyst promoters is used, wherein the catalyst promoter is selected from the group consisting of
- (a) aldehyde and ketone promoters containing one or more carbonyl containing compounds of the general formula ##STR10## wherein R.sub.1, and R.sub.2 are, independently, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, or hydrogen, and wherein the R-designated groups in addition can contain one or more functional groups selected from the group consisting of hydroxyl, carboxyl, carbonyl, amine, nitro or halogen;
- (b) amide promoters containing one or more amide containing compounds of the general formula ##STR11## wherein R.sub.1, R.sub.2, and R.sub.3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups or aryl groups and wherein the R-designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, carboxyl, carbonyl, amine, nitro or halogen;
- (c) amine promoters containing one or more amine containing compounds of the general formula ##STR12## wherein R.sub.1, R.sub.2, and R.sub.3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, or aryl groups, and wherein the R-designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, carbonyl, halogen, carboxyl, nitro, or amide;
- (d) organic acid promoters containing one or more carboxylic acid containing compounds of the general formula ##STR13## wherein R.sub.1 is a hydrogen, linear or branched acyclic group, alicyclic group, cyclic group, or aryl group and wherein R can in addition contain one or more functional groups selected from the group consisting of carbonyl, hydroxyl, halogen, nitro, amine, or amide.
Dependencies are inferred from the claim text.