Process for preparing olefin-terminated alkylphenoxypolyethoxyethanols

Abstract

Abstract The invention comprises mixtures of compounds of the formula RO(CH2CH2O)xR1 in which R is a C8- 18 alkyl or alkenyl group or a C10- 24 mono- or di-alkylphenyl group, R1 is a C4- 12 tertiary alkyl group or alicyclic group derived from a monoterpene, and x has an average value between 7 and 50 inclusive. The preferred embodiment of the invention has R=octylphenyl and R1=tertiary butyl, with x=9-13, or R1=isobornyl (from camphene) and x=25-35. In the preparation of these and other compounds the polyethenoxy alcohol is reacted with a C4- 12 tertiary olefin over a macroreticular anhydrous sulphonic acid cation exchange resin of high specific surface area in the hydrogen form, as catalyst. Reaction conditions vary according to the olefin-temperatures may be 20-27 DEG C. for isobutylene and 50-60 DEG C. for camphene. Pressures should suffice to keep excess olefin dissolved in the alcohol, and may be up to 30 p.s.i.g. for olefins boiling below 25-30 DEG C. The catalyst is removed when the required degree of etherification is achieved, any acid leached from the catalyst is neutralized and uncreated olefin distilled off or solvent extracted. The product may be further purified to remove unreacted alcohol. At least a 2 molar excess of olefin is desirable. The products exhibit high resistance to oxidation when mixed with an alkali. Table I compares the catalytic effect of a macroreticular resin with other sulphonic acid catalysts. The examples describe the reaction of isobutylene with polyethenoxy derivatives of various octyl alcohols, dodecanol, tridecyl alcohol, hexadecyl alcohol, stearyl and oleyl alcohols, 5,5,7,7-tetramethyl octanol-2, and of t-dodecyl phenol, sec.-octadecyl phenol, t-nonyl phenol, dinonyl phenol, octyl phenols, t-octyl methyl phenol and t-butyl phenol, and the reaction of camphene with polyethenoxy derivatives of octadecanol, octylphenol and dodecylphenol. Also described are the reactions of octylphenol polyethenoxy alcohols with a pentene mixture, diisobutylene, a -methylstyrene, a -pinene and d-limonene. In all cases the catalyst is "Amberlyst 15" (Registered Trade Mark) and the catalyst after reaction is removed and washed with isopropanol, which is added to the product, which is then neutralized with alcoholic NaOH and stripped of solvents. Uses: defoaming agents; wetting agents and detergents in textile processes; detergent for non-porous surfaces.ALSO:The invention comprises mixtures of compounds of the formula RO(CH2CH2O)xR1 in which R is a C8-C18 alkyl or alkenyl group or a C10- 24 mono- or di-alkyl-phenyl group, R1 is a C4- 12 tertiary alkyl group or an alicyclic group derived from a monoterpene, and x has an average value between 7 and 50 inclusive. A preferred embodiment of the invention has R=octylphenyl, R1=tertiary butyl and x= 9-13. The mixtures are prepared by reaction of the polyethenoxy alcohol with a C4- 12 tertiary olefin over a macroreticular anhydrous sulphonic acid cation exchange resin of high specific surface area. An excess of olefin is desirable. The examples include descriptions of the reactions of isobutylene with condensates of dodecanol with 10 mols of ethylene oxide, octanol with 7 mols, t.-octylphenol with 7 and 10 mols, t.-dodecylphenol with 12.5 mols, t.-nony-phenol with 10 mols, sec.-octadecyl-phenol with 10 mols, di-nonylphenol with 9 mols, t.-butylphenol with 7 mols, and iso-octanol with 10 mols of ethylene oxide, and of diisobutylene with a reaction product from t.-octylphenol and 12.5 mols of ethylene oxide.

Inventors

• 👤 Fred E Boettner
• 👤 Robert M Ross

Bibliographic Details