Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-05-04
2003-06-10
Keys, Rosalynd (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S609000, C568S616000, C568S618000, C568S620000, C568S622000, C568S625000
Reexamination Certificate
active
06576799
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an industrial process for preparing low-foaming nonionic surfactants and more particularly to a process for preparing ether-capped poly(oxyalkylated) alcohol surfactants which have superior spotting and filming benefits in dishwashing and hard surface cleaning applications, as well as suds suppression in detergent compositions.
BACKGROUND OF THE INVENTION
Ether-capped poly(oxyalkylated) alcohols can be prepared using various catalysts, such as Lewis acids. However, for industrial production, metallic catalysts, such as stannic chloride is preferred. In addition to being an excellent catalyst for the reaction of a glycidyl ether with ethoxylated alcohol, metallic catalysts are economical and readily available in commercial bulk quantities. They also offer safety and ease of handling advantages on an industrial scale versus alternative catalysts. One important disadvantage for metallic catalysts is that the soluble metallic residue component of the catalyst, such as tin residues when is the catalyst SnCl
4
, resulting from there use as reaction catalyst, generally cannot be tolerated above about 100 ppm in many cleaning formulations and applications and these residues are difficult and expensive to remove from ether-capped poly(oxyalkylated) alcohol compositions. Successful laboratory approaches to removal of residual metallic catalyst component, such as the use of a silica gel plug and eluting with a 5% methanol in dichloromethane solution leads to complexity and high cost on an industrial production scale. Due to the surfactant properties of the ether-capped poly(oxyalkylated) alcohol, water washing for metallic catalyst component removal leads to emulsification problems leading to complex organic—aqueous separations.
Consequently, the problem remains that there is no commercially viable or industrial scale process for the removal of these metallic catalyst component residues from the ether-capped poly(oxyalkylated) alcohol compositions.
BACKGROUND ART
U.S. Pat. No. 4,272,394, issued Jun. 9, 1981, U.S. Pat. No. 5,294, 365, issued Mar. 15, 1994 U.S. Pat. No. 4,248,729, issued Feb. 3, 1981; U.S. Pat. No. 4,284,532, issued Aug. 18, 1981; U.S. Pat. No. 4,627,927, issued Dec. 9, 1986; U.S. Pat. No. 4,790,856, issued Dec. 13, 1988; U.S. Pat. No. 4,804,492, issued Feb. 14, 1989; U.S. Pat. No. 4,770,815, issued Sep. 13, 1989; U.S. Pat. No. 5,035,814, issued Jul. 30, 1991; U.S. Pat. No. 5,047,165, issued Sep. 10, 1991; U.S. Pat. No. 5,419,853, issued May 30, 1995; U.S. Pat. No. 5,294,365, issued Mar. 15, 1994; GB Application No. 2,144,763, published Mar. 13, 1985; GB Application No. 2,154,599, published Sep. 9, 1985; WO Application No. 9,296,150, published Apr. 16, 1992; WO 94/22800, published Oct. 13, 1994, WO 93/04153, published Mar. 4, 1993, WO 97/22651, published Jun. 26, 1997, EP Application No. 342,177, published Nov. 15, 1989 and “Glyceryl Bisether Sulfates. 1: Improved Synthesis” Brian D. Condon; Journal Of the American Chemical Society, Vol. 71, no. 7 (July 1994).
SUMMARY OF THE INVENTION
A process for removing metallic catalyst component residues from the ether-capped poly(oxyalkylated) alcohol reaction product has been discovered that is simple and economical to practice on an industrial scale. It has been discovered that selected aqueous solutions can be used to effectively extract the metallic catalyst component residues from ether-capped poly(oxyalkylated) alcohol while avoiding oil and water phase emulsification. This extraction method of purification avoids organic solvents, costly process aids, process complexity and provides a simple, economic industrial route to remove the metallic catalyst component residues in ether-capped poly(oxyalkylated) alcohols to below about 100 ppm. This residue extraction can be carried out as either a batch or continuous process. Furthermore, the residue can be removed in a single or multiple extraction steps.
In accordance with a first aspect of the present invention, a process for preparing an ether-capped poly(oxyalkylated) alcohol surfactant is provided. The surfactant has the formula:
R
1
O[CH
2
CH(R
3
)O]
x
CH
2
CH(OH)CH
2
OR
2
wherein R
1
and R
2
are linear or branched, saturated or unsaturated, aliphatic or aromatic hydrocarbon radicals having from about 1 to about 30 carbon atoms; R
3
is H, or a linear aliphatic hydrocarbon radical having from about 1 to about 4 carbon atoms; x is an integer having an average value from 1 to about 30, wherein when x is 2 or greater, R
3
may be the same or different, independently H, or C
1
to C
4
in any given molecule, further wherein when x is 15 or greater and R
3
is H and methyl, at least four of R
3
are methyl, further wherein when x is 15 or greater and R
3
includes H and from 1 to 3 methyl groups, then at least one R
3
is ethyl, propyl or butyl, further wherein R
2
can optionally be alkoxylated, wherein said alkoxy is selected from ethoxy, propoxy, butyloxy and mixtures thereof. The process comprises the steps of:
(a) providing a glycidyl ether having the formula:
wherein R
2
is defined as above;
(b) providing an ethoxylated alcohol having the formula:
wherein R
1
, R
3
and x are defined as above; and
(c) reacting the glycidyl ether with the ethoxylated alcohol to form the surfactant in the presence of a metallic catalyst;
(d) said surfactant is sparged with an inert gas, preferably N
2
, Ar and mixtures thereof, optionally under vacuum, preferably a vacuum in the range of 5 to 500 mmHg; and
(e) extracting said catalyst from said surfactant by at least one aqueous extraction with an aqueous solution, wherein said aqueous solution is selected from the group consisting of a from about 2% to about 15% by weight aqueous solution of sodium carbonate, a from about 2% to about 10% by weight aqueous solution of potassium carbonate, a from about 1% to about 22% by weight aqueous solution of sodium sulfate, a from about 2% to about 6% by weight aqueous solution of sodium bicarbonate, a from about 1% to about 10% by weight aqueous solution of potassium sulfate, a from about 2% to about 24% by weight aqueous solution of potassium bicarbonate, and mixtures thereof; and wherein said surfactant, after said at least one aqueous extraction, contains less than about 100 ppm of the metallic component of said metallic catalyst.
R
1
and R
2
are preferably a linear or branched, saturated or unsaturated, aliphatic hydrocarbon radical having from about 6 to about 22 carbon atoms and x is an integer having an average value of from about 6 to about 15.
The step of reacting the glycidyl ether with the ethoxylated alcohol is preferably conducted at a temperature of from about 50° C. to about 95° C. with 60° C. to about 80° C. even more preferred when Lewis acid catalysts are employed.
The step of providing the glycidyl ether may further comprise the step of reacting a linear aliphatic or aromatic alcohol having the formula R
2
OH and an epoxide having the formula:
wherein R
2
is defined as above and X is a leaving group. This reaction may also be conducted in the presence of a catalyst as defined above. The catalyst is typically employed at levels of about 0.1 mol % to about 2.0 mol % and the reaction is preferably conducted in the absence of a solvent at temperatures of from about 40° C. to about 90° C.
As already noted, the surfactants have advantages, including superior spotting and filming reduction benefits as well as excellent greasy soil removal, good dishcare, suds suppression and good overall cleaning.
Accordingly, it is an aspect of the present invention to provide a process for producing a low-foaming nonionic surfactant having superior spotting and filming reduction benefits as well as excellent greasy soil removal, good dishcare, suds suppression and good overall cleaning. It is a further aspect of the present invention to provide a process for producing an ether-capped poly(oxyalkylated) alcohol surfactant. It is a further aspect of the present invention to provide a low-foaming nonionic surfactant produced by the process of t
Formyduval Terry Franklin
Kluesener Bernard William
Levengood Donald Eugene
Miller Larry Eugene
Sivik Mark Robert
Keys Rosalynd
Miller Steven W.
The Procter & Gamble & Company
Waugh Kevin L.
Zerby Kim W.
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