Preparing From Organic Hydroxy Containing Compound (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/618)
  • Patent number: 5144093
    Abstract: A process for producing an ethylene oxide-capped polyol which is essentially free of catalyst residues, wherein the polyol is produced using a double metal cyanide catalyst, which comprises after polyol formation the steps of: (a) contacting a catalyst residue(s)- containing polyol with an effective amount of an oxidant (preferably selected from the group consisting of: oxygen-containing gas(es), peroxide(s), acids, and combinations thereof) to cause said catalyst residue(s) to form insoluble residues that are insoluble in the polyol; (b) separating the insoluble residues from the polyol to provide an essentially double metal cyanide catalyst residue-free polyol; (c) treating said double metal cyanide catalyst residue-free polyol with a base to provided a base-treated polyol; (d) contacting said base-treated polyol with ethylene oxide to produce an ethylene oxide-capped polyol containing base, wherein at least a portion of the secondary hydroxyl groups on said polyol are converted into primary hydroxyl groups
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: September 1, 1992
    Assignee: Olin Corporation
    Inventors: John W. Reisch, Michael M. Martinez, Maurice Raes
  • Patent number: 5136106
    Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zirconium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.
    Type: Grant
    Filed: March 14, 1991
    Date of Patent: August 4, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5130413
    Abstract: A process for producing an unsaturated group-terminated high-molecular weight polyalkylene oxide by adding an alkali metal and/or an alkali metal compound capable of producing an alkali metal hydroxide on reaction with water to a hydroxyl-terminated polyalkylene oxide having a repeating unit represented by formula --R.sup.1 --O-- (wherein R.sup.1 represents a divalent alkylene group having from 2 to 8 carbon atoms) to substitute the hydrogen atom of the hydroxyl end group with an alkali metal (alkoxidation) the resulting polyalkylene oxide is reacted with a polyhalogen compound to increase the molecular weight of the polyalkylene oxide and then additional alkali metal and/or alkali metal compound is added before reacting the resulting high-molecular weight polyalkylene oxide with an unsaturated halogen compound to introduce an unsaturated group to the molecular chain terminals.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: July 14, 1992
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yukimitsu Asai, deceased, by Keiji Asai, legal representative, by Yoshie Asai, legal representative, Hiroyuki Kawata, Tooru Nakagawa
  • Patent number: 5126493
    Abstract: Alkoxylates of active hydrogen compounds having a peaked molecular weight distribution are prepared by reacting the active hydrogen compound with an alkylene oxide of from 2 to 4 carbon atoms using iron oxides as alkoxylation catalysts.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: June 30, 1992
    Inventors: Wolfgang Hoelderich, Jochen Houben, Gerhard Wolf, Michael G. Kinnaird
  • Patent number: 5118448
    Abstract: Esterified alkoxylated polyols useful as fat mimetics may be prepared by alkoxylating a benzylated polyol with an epoxide under basic conditions, reacting the benzyl ether group with hydrogen to convert it to a hydroxy group, and then esterifying with a fatty acid compound. The resulting product has at least one fatty acid ester group attached directly to the polyol residue.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: June 2, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Charles F. Cooper
  • Patent number: 5118870
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: April 23, 1990
    Date of Patent: June 2, 1992
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 5114619
    Abstract: This invention is a process for the preparation of a polyol having an equivalent weight of 200 to 5000 by the reaction of a monoepoxy compound with an initiator containing an active hydrogen atom in the presence of a catalyst substance selected from the group consisting of barium, strontium and their oxides, hydroxides, hydrated hydroxides or monohydroxide salts, and mixtures thereof. The process comprises adding water during the reaction of the monoepoxy compound with the initiator. The quantity of water added is one percent or less by weight of the total weight of monoepoxy compound to be reacted with the initiator.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: May 19, 1992
    Assignee: The Dow Chemical Company
    Inventor: A. J. Heuvelsland
  • Patent number: 5112519
    Abstract: This invention relates to processes for making biodegradable surfactant. The process comprises several steps including an optional step. The first step is directed to reacting olefins with ZSM-23 catalyst to form oligomers having the formula (C.sub.3).sub.x, (C.sub.4).sub.x or mixtures thereof. Second, the oligomer is hydroformylated to form a saturated alcohol, for example, tridecanol. Next, the saturated alcohol is ethoxylated. Thereafter a nonionic biodegradable surfactant is recovered. This surfactant can be used in detergent formulations. A process is also taught for making esters which can be used as lubricants or plasticizers. A specific hydroformylation process is taught which utilizes modified cobalt carbonyl catalyst. Also, a specific ethoxylation process is taught. Products formed according to the latter two processes as well as their uses are also taught.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: May 12, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas J. Giacobbe, George A. Ksenic
  • Patent number: 5110991
    Abstract: Disclosed is a novel method for alkoxylation alcohols by reacting the alcohols with epoxides over a heterogeneous catalyst comprising a fluoride of an element of Group I of the Periodic Table on an oxide of Group IIA or Group IIIA of the Periodic Table.
    Type: Grant
    Filed: April 1, 1991
    Date of Patent: May 5, 1992
    Assignee: Texaco Chemical Company
    Inventors: Donald H. Champion, George P. Speranza
  • Patent number: 5110992
    Abstract: A process for the preparation of a glycol ether by reacting an olefin oxide with an excess of an alcohol over a catalyst; characterized in that the catalyst comprises a material which has been prepared by calcination of an anionic double hydroxide clay having a structure comprising magnesium and aluminum in combination, followed by rehydration and subsequent recalcination.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: May 5, 1992
    Assignee: The British Petroleum Co., p.l.c.
    Inventors: Martin P. Atkins, William Jones, Malama Chibwe
  • Patent number: 5104987
    Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: April 14, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5104575
    Abstract: This invention relates to heterogeneous (organic polymer-supported) calcium-containing catalysts and the use thereof in the preparation of alkoxylation products, i.e., condensation reaction products of alkylene oxides and organic compounds having at least one active hydrogen. In another aspect of this invention, processes are provided for preparing heterogeneous (organic polymer-supported) calcium-containing catalysts for alkoxylation using calcium oxide or calcium hydroxide as sources for the catalytically-active calcium. In a further aspect of this invention, alkoxylation products are provided that have beneficial, narrow molecular weight ranges and are essentially neutral in pH and free from catalyst residues.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 14, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Robert J. Knopf
  • Patent number: 5069817
    Abstract: A process for the production of alkyl polyoxyethylenes showing improved low-temperature behavior, by reaction of alcohols with ethylene oxide at elevated temperature in the presence of basic alkali metal compounds as catalysts and subsequent neutralization of the alkaline catalyst with acids, which under prior art practice was impractical because of clogging of reaction vessels and equipment associated with precipitation of salts during neutralization, is made practical by adding a finely divided solid to serve as a precipitation control agent during neutralization. The finely divided solids used are, in particular, organic and/or inorganic materials known in the prior art as filter aids, such as kieselguhr and sawdust or other finely divided cellulose.
    Type: Grant
    Filed: January 25, 1989
    Date of Patent: December 3, 1991
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Karl Schmid, Alfred Meffert, Klaus Friedrich, Michael Langen, Klaus Herrmann
  • Patent number: 5068456
    Abstract: Nonionic surfactants containing a narrow molecular weight distribution is obtained by the use of a magnesium-containing catalyst which comprises reacting a reactive hydrogen compound selected from the group consisting of monohydric alcohols having from about 6 to 30 carbon atoms with an alkylene oxide having from 2-4 carbon atoms at a temperature at which the reaction proceeds in the presence of at least a catalytic amount of a phenolic activated magnesium catalyst containing phosphorus.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: November 26, 1991
    Assignee: Texaco Chemical Company
    Inventor: Edward C. Y. Nieh
  • Patent number: 5059719
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more soluble basic compounds of one or more elements of the lanthanum series (atomic numbers 57-71, inclusive). The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates. When the process is applied to the preparation of alkylene oxide, particularly ethylene oxide, adducts of alkanols, particularly primary alkanols in the C.sub.6 to C.sub.24 range, the product is a valuable narrow range nonionic surfactant, characterized by relatively narrow distribution of alkylene oxide adducts.
    Type: Grant
    Filed: March 23, 1990
    Date of Patent: October 22, 1991
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 5057627
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: October 15, 1991
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 5057628
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: October 15, 1991
    Assignee: Shell Oil Company
    Inventors: Charles L. Edwards, Richard A. Kemp
  • Patent number: 5053556
    Abstract: A one-step process for producing an alkenyl ether in only one step and under mild conditions by reacting an aldehyde of the formula ##STR1## with an alcohol of the formulaR.sup.3 --OHin the presence of an acidic catalyst in liquid phase, and recovering as the reaction product an alkenyl ether of the formula ##STR2## wherein R.sup.1 is a 2-8 C alkyl or R--CH.sub.2 --CH.dbd. wherein R is a 1-8 C alkyl group,R.sup.2 is a 1-6 C alkyl,R.sup.3 is a linear or branched 6-12 C alkyl, a cyclohexyl, a hydroxyhexamethylenyl or ##STR3## wherein R' is H and n is 2 or 3, R.sup.4 is hydrogen or R--CH.sub.2 --CH.dbd. wherein R is a 1-8 C alkyl group, andR.sup.5 is a 2-8 C alkyl or R--CH.dbd.CH-- wherein R is a 1-8 C alkyl.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: October 1, 1991
    Assignee: Chisso Corporation
    Inventor: Noriyuki Ohnishi
  • Patent number: 5026923
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the borate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: June 25, 1991
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 5012012
    Abstract: An alkoxylation catalyst for causing an alkylene oxide to react with an organic compound having one or more active hydrogen, comprising magnesium oxide modified by the addition of at least one metal ion selected from the group consisting of Al.sup.3+, Ga.sup.3+, In.sup.3+, Tl.sup.3+, Co.sup.3+, Sc.sup.3+, La.sup.3+, and Mn.sup.2+. In the presence of the catalyst, an addition polymerization reaction between the alkylene oxide and the organic compound having one or more active hydrogen such as an alcohol or phenol can be performed with only small amounts of unreacted material and byproducts, and the alkylene oxide adduct having a very narrow alkylene oxide adduct distribution can be obtained.
    Type: Grant
    Filed: April 25, 1989
    Date of Patent: April 30, 1991
    Assignee: Lion Corporation
    Inventors: Hirofumi Nakamura, Yuichi Nakamoto, Yuji Fujimori
  • Patent number: 5010187
    Abstract: Polyether polyols having an equivalent weight of from about 200 to about 5000 are prepared by the process of this invention. The process uses barium- or strontium-containing alkoxylation catalysts to provide products with reduced unsaturation in comparison to similar products produced with potassium hydroxide catalysis. The use of these catalysts also increases the capping efficiency with ethylene oxide to provide products with a higher primary hydroxyl content for the same weight percentage of ethylene oxide cap.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: April 23, 1991
    Assignee: Dow Chemical Company
    Inventor: Albert J. Heuvelsland
  • Patent number: 5010047
    Abstract: A process for recovering double metal cyanide complex catalyst from a polymer such as polypropylene glycol in a form suitable for use as a polymerization catalyst is described. The process comprises the steps of (a) combining the polymer with a non-polar solvent to precipitate the catalyst and (b) filtering the resulting mixture in the presence of a filter aid to separate the polymer from the precipitated catalyst. In contrast to the prior art methods of catalyst removal, the process of the invention yields polymer uniformly low in color as well as recovered catalyst which may be reused in subsequent polymerizations.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: April 23, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventor: Jonathan L. Schuchardt
  • Patent number: 5003111
    Abstract: Novel polyether polyols are disclosed which contain an internal block of isobutylene oxide or a mixture of isobutylene oxide and a mono- or unsaturated alkylene oxide and an end-cap of a mono- or unsubstituted alkylene oxide to provide reactive primary or secondary hydroxyl end-groups. The polyether polyols are useful intermediates in the production of segmented elastomers. A process for the preparation of the novel polyols is also described in which an alkali metal catalyst and a crown ether cocatalyst are employed to afford polyols containing relatively low levels of unsaturation.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: March 26, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventor: Stephen D. Harper
  • Patent number: 4996364
    Abstract: Alkaline earth salts of polycarboxylic acid monoesters corresponding to general formula I[R-(OC.sub.m H.sub.2m).sub.n -O-CO-A(COO.sup.-).sub.o ].sub.p M.sup.2+(I)in whichR is a radical selected from the group consisting of a linear or branched C.sub.1 -C.sub.22 alkyl or C.sub.3 -C.sub.22 alkenyl, phenyl, alkylphenyl containing 1 to 3 C.sub.1 -C.sub.15 alkyl groups, benzyl and phenethyl,A is a saturated or unsaturated, acyclic or cyclic C.sub.2 -C.sub.6 hydrocarbon radical with two or three bonds or a benzene group with two or three bonds,M is an alkaline earth metal selected from the group consisting of Ca, Ba and Sr;m is the number 2 or 3;n is a number from 1 to 20;o is the number 1 and p is the number 2 or o is the number 2 and p is the number 1, are employed as catalysts for the ethoxylation or propoxylation of compounds containing active hydrogen atoms.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: February 26, 1991
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ansgar Behler, Uwe Ploog
  • Patent number: 4994626
    Abstract: A process for preparing an etherified polyoxyalkylene derivative of the formula ##STR1## wherein R.sup.1 and R.sup.4 are identical or different and are each independently C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.6 -C.sub.20 aryl, C.sub.6 -C.sub.20 alkyl aryl, C.sub.6 -C.sub.20 cycloalkyl, and mixtures thereof, R.sup.2 and R.sup.3 are identical or different and independent of each other are H, CH.sub.3, CH.sub.3 CH.sub.2, and mixtures thereof, m, m' and n are identical or different and are each greater than or equal to zero, with the proviso that m+m'+n is from 3 to 300; by reacting a polyoxyalkylene compound of the formula.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: February 19, 1991
    Assignee: BASF Corporation
    Inventors: Ronald E. Greenough, Jay G. Otten, Stefan Birnbach, Jochen Houben
  • Patent number: 4988797
    Abstract: Cyclic ethers having 4 and 5 member rings are polymerized with a alcohol initiator and an acid catalyst. The acid catalyst is used at a molar ratio relative to hydroxyl groups of the alcohol initiator of between about 0.05:1 and about 0.5:1.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: January 29, 1991
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 4983778
    Abstract: Alkoxylation products of organic compounds containing active H atoms with a narrow homolog distribution range is produced by using as a catalyst in the alkoxylation process a catalyst composition comprising:a. Esters of titanic and/or zirconic acid with monoalkanols containing 1 to 4 carbon atoms in combination with,b. sulfuric acid and/or alkanesulfonic acid containing 1 to 6 carbon atoms and/or hydroxyarylsulfonic acids as catalysts for the ethoxylation or propoxylation of compounds containing active H atoms provide the alkoxylation products with a narrow homolog distribution range.
    Type: Grant
    Filed: May 2, 1989
    Date of Patent: January 8, 1991
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Uwe Ploog
  • Patent number: 4983323
    Abstract: A composition for use in formulating detergents containing water, a neutral salt thixotrope and a water-soluble salt of an ether sulfate having the formula[R-A.sub.n O-SO.sub.3 ].sub.x Mwherein R is a hydrocarbon group containing from about 4 to about 30 carbon atoms, A is an oxyalkylene group selected from the group consisting of oxyethylene, oxypropylene, oxybutylene, oxytetramethylene and heteric and block mixtures thereof, n is an integer from 1 to 8 and M is a cation of a water-soluble salt, and wherein at least about 85% by weight of said ether sulfate has a number average oxyalkylene number of p-2 to p+3, wherein p represents the number of oxyalkylene groups of the most prevalent oxyalkylate species, and x is 1 or 2 depending on the valence of M.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: January 8, 1991
    Assignee: Vista Chemical Company
    Inventors: Michael F. Cox, Peter A. Schwab, Dewey L. Smith
  • Patent number: 4967016
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of the compound barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: October 30, 1990
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 4962237
    Abstract: A catalytic process for polymerizing epoxides using active hydrogen initiators forming polyols having low unsaturation levels and high primary hydroxyl levels. The catalysts useful in this process are prepared from catalyst precursors exemplified by hydrotalcite. This process is more reactive with less acidic active hydrogen initiators. The polyols can be used in urethanes without removal of the catalyst.
    Type: Grant
    Filed: January 2, 1990
    Date of Patent: October 9, 1990
    Assignee: The Dow Chemical Company
    Inventor: David E. Laycock
  • Patent number: 4960952
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: October 2, 1990
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 4946984
    Abstract: This invention relates to the use of calcium sulfate as a catalyst in the preparation of alkoxylation products, i.e., condensation reaction products of alkylene oxides and organic compounds having at least one active hydrogen, that have beneficial, narrow molecular weight ranges.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: August 7, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Charles F. Hauser
  • Patent number: 4943626
    Abstract: Polyether active hydrogen compounds having at least two terminal active hydrogen groups on primary carbon atoms are prepared by (a) forming polyoxyalkylene molecules each having at least one active hydrogen precursor, (b) linking at least two of the polyoxyalkylene molecules, and (c) converting the active hydrogen precursor groups to active hydrogen groups on primary carbon atoms. The polyoxyalkylene molecule is formed by exposing a reaction mixture comprising at least one alkylene oxide and at least one protective initiator to conditions effective for the polymerization of the alkylene oxides. Linking is accomplished at polyether chain ends distal to the protected active hydrogen precursor groups, such that the active hydrogen precursors remain on the linked polyether chains until they are converted to active hydrogen groups.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: July 24, 1990
    Assignee: The Dow Chemical Company
    Inventors: James E. McGrath, Youngtai Yoo, Robert B. Turner, Diane M. Lewis
  • Patent number: 4933502
    Abstract: An improved process for the preparation of narrow-range alkanol alkoylates by the addition reaction of higher alkanols with alkylene oxides, particularly ethylene oxide. U.S. Pat. No. 4,721,816 describes a process in which alkylene oxides are added to alkanols by reaction in the presence of a catalyst prepared by contacting a sulfur-containing acid such as sulfuric acid with one or more aluminum compounds selected from the group consisting of aluminum alcoholates and aluminum phenolates. Under the present invention, that process is improved by carrying out the process in the further presence of water, provided that certain critical restrictions are placed upon the proportions of the water and of the sulfuric acid and aluminum catalyst components. The process improvement of the invention offers substantial improvement in alkoxylation reaction rate and/or selectivity of the reaction to the desired alkanol alkoxylate products, rather than to by-products such as polyalkylene glycols.
    Type: Grant
    Filed: June 2, 1988
    Date of Patent: June 12, 1990
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 4922029
    Abstract: Etherified polyoxyalkylene derivatives of the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.20 -alkyl or C.sub.3 -C.sub.5 -alkenyl, R.sup.2 and R.sup.3 independently of one another are each hydrogen, methyl or ethyl, R.sup.4 is C.sub.1 -C.sub.4 -alkyl and m and n are identical or different and are each greater than or equal to 0, with the proviso that the sum of m and n is from 3 to 300, are prepared by reacting the corresponding hydroxyl-containing polyoxyalkylene derivative with a dialkyl sulfate in the presence of an alkali metal hydroxide by a process in which the reaction is carried out at from 20.degree. to 60.degree. C. in the presence of an aqueous solution of an alkali metal hydroxide, the concentration of alkali metal hydroxide during the entire duration of the reaction being not less than 35% by weight, based on the aqueous phase, and not less than 1 mole of dialkyl sulfate and not less than one mole of alkali metal hydroxide are used per mole equivalent of organic hydroxyl groups.
    Type: Grant
    Filed: August 5, 1988
    Date of Patent: May 1, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Birnbach, Josef Mueller, Klaus Wulz, Jochen Houben
  • Patent number: 4902834
    Abstract: A process is disclosed for the preparation of capped polyoxyalkylene block polyethers with exceptionally low hydroxyl numbers and correspondingly high capping efficiency. This improvement is accomplished through the use of cesium hydroxide catalysis during oxyethylation.
    Type: Grant
    Filed: August 30, 1988
    Date of Patent: February 20, 1990
    Assignee: BASF Corporation
    Inventors: Jay G. Otten, Roger A. Ott
  • Patent number: 4898992
    Abstract: In the novel process alkylene glycol monoalkyl ethers of the formula ##STR1## in which R.sup.1 is an alkyl radical having 1 to 25 carbon atoms, R.sup.2 is H, CH.sub.3 or C.sub.2 H.sub.5 and, within the chain of the polyoxyalkylene radical, arranged randomly or in blocks, can also assume all three meanings, R.sup.3 is CH.sub.3 or C.sub.2 H.sub.5 and n denotes 1 to 100, are hydrogenated to give the corresponding alkylene glycol dialkyl ethers in the presence of a supported nickel catalyst using hydrogen without pressure.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: February 6, 1990
    Assignee: Hoechst AG
    Inventors: Achim Stankowiak, Hildegard Schulz
  • Patent number: 4894485
    Abstract: Alkaline earth metal salts of ether carboxylic acids corresponding to the following general formula[RO--(C.sub.m H.sub.2m O).sub.n --CH.sub.2 --COO.sup.- ].sub.x M.sup.2+(I)in which R represents C.sub.1 -C.sub.22 alkyl, C.sub.3 -C.sub.22 alkenyl, phenyl, alkylphenyl containing 1 to 3 C.sub.1 -C.sub.15 alkyl radicals, benzyl or phenylethyl, M represents Ca, Sr or Ba, m is equal to 2 or 3, n is equal to 1 to 20 and x is equal to 2; or R is a group of the formula --CH.sub.2 --COO.sup.-, x is equal to 1 and M, m and n are as defined above, are used as catalysts for the ethoxylation or propoxylation of organic compounds containing active H atoms. They afford advantages by virtue of the solubility of the catalysts in the reaction medium and provide for a narrow homolog distribution of the polyalkoxylation products.
    Type: Grant
    Filed: June 14, 1988
    Date of Patent: January 16, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ansgar Behler, Uwe Ploog, Elvira Scholz
  • Patent number: 4892977
    Abstract: Nonionic surfactants containing a narrow molecular weight distribution is obtained by the use of a magnesium-containing catalyst which comprises reacting a reactive hydrogen compound selected from the group consisting of monohydric alcohols having from about 6 to 30 carbon atoms with an alkylene oxide having from 2-4 carbon atoms at a temperature at which the reaction proceeds in the presence of at least a catalytic amount of a particular magnesium catalyst containing phosphorus.
    Type: Grant
    Filed: June 13, 1988
    Date of Patent: January 9, 1990
    Assignee: Texaco Chemical Company
    Inventor: Edward C. Y. Nieh
  • Patent number: 4886917
    Abstract: Narrow, balanced alkoxylation product mixture distributions having at least one alkoxylation product constituting more than 20 weight percent of the mixture can be provided by modified, calcium-containing catalysts. Catalysts for alkoxylation processes can be produced from lime and can, with modification, be used to make the narrow, balanced alkoxylation product mixture distribution.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: December 12, 1989
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Robert J. Knopf, Louis F. Theiling, Jr.
  • Patent number: 4879419
    Abstract: Hydroxyl terminated polyepichlorohydrin having a polydispersity of less than 1.2 and a molecular weight of at least 2000, and method of preparation using stannic chloride and strong carboxylic acid co-catalysts.
    Type: Grant
    Filed: July 1, 1985
    Date of Patent: November 7, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Birger Johannessen
  • Patent number: 4835321
    Abstract: A process for preparing an alkoxylation catalyst in which the catalyst pre-mix is formed by admixing an alkoxylated alcohol with a calcium containing compound which is dispersible in the alkoxylated alcohol, an inorganic acid and an aluminum trialkoxide, the pre-mix being heated to a temperature and for a time sufficient to effect at least partial exchange reaction betweeen the alkoxide groups of the aluminum alkoxide and the hydroxyl groups of the alkoxylated alcohol. There is also disclosed and claimed an alkoxylation process utilizing the catalysts formed as described above.
    Type: Grant
    Filed: April 13, 1988
    Date of Patent: May 30, 1989
    Assignee: Vista Chemical Company
    Inventors: Bruce E. Leach, Mark L. Shannon, Donald L. Wharry
  • Patent number: 4825009
    Abstract: Alkylene oxide adducts of higher alkanols are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an alkanol reactant comprising one or more C.sub.6 to C.sub.30 alkanols in the presence of a catalytically effective amount of a catalyst which combines (i) one or more sulfur-containing acids with (ii) one or more aluminum compounds selected from the group consisting of aluminum alcoholates and aluminum phenolates, the relative molar ratio of component (i) to component (ii) being in the range from about 0.1:1 to 1:1. Alkanol alkoxylates, and particularly alkanol ethoxylates, prepared in this manner are characterized by a relatively narrow-range distribution of alkylene oxide adducts and by a relatively low content of residual alkanol. The products of this process are nonionic surfactants, particularly useful as components of detergent formulations.
    Type: Grant
    Filed: September 29, 1987
    Date of Patent: April 25, 1989
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 4820673
    Abstract: Narrow, balanced alkoxylation product mixture distributions having at least one alkoxylation product constituting more than 20 weight percent of the mixture can be provided by modified, calcium-containing catalysts. Catalysts for alkoxylation processes can be produced from lime and can, with modification, be used to make the narrow, balanced alkoxylation product mixture distribution.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: April 11, 1989
    Assignee: UOP
    Inventors: Robert J. Knopf, Louis F. Theiling, Jr.
  • Patent number: 4806658
    Abstract: High molecular weight polyethylene glycol monoethers are cleaved to prepare lower oligomeric reaction products by contacting a mixture of the high molecular weight polyethylene glycol monoether and water with a hydrolytic cleavage catalyst such as alumina at elevated temperatures.
    Type: Grant
    Filed: November 15, 1982
    Date of Patent: February 21, 1989
    Assignee: The Dow Chemical Company
    Inventors: Kuo Y. Chang, Iwao Kohatsu, Philip E. Garrou
  • Patent number: 4775653
    Abstract: A process for preparing an alkoxylation catalyst in which the catalyst pre-mix is formed by admixing an alkoxylated alcohol with a calcium containing compound which is dispersible in the alkoxylated alcohol, an inorganic acid and an aluminum trialkoxide, the pre-mix being heated to a temperature and for a time sufficient to effect at least partial exchange reaction between the alkoxide groups of the aluminum alkoxide and the hydroxyl groups of the alkoxylated alcohol. There is also disclosed and claimed an alkoxylation process utilizing the catalysts formed as described above.
    Type: Grant
    Filed: April 28, 1987
    Date of Patent: October 4, 1988
    Assignee: Vista Chemical Company
    Inventors: Bruce E. Leach, Mark L. Shannon, Donald L. Wharry
  • Patent number: 4762952
    Abstract: A perfluorosulphonic acid polymer suitable for use as a catalyst contains units of the formula:[(SO.sub.3).sub.w M(SO.sub.3 R).sub.z-w ] (I)whereinM is a multivalent metal cation,R is a C.sub.1 to C.sub.8 fluorinated alkyl group,z is the valency of M, andw is an integer having a value between 1 and z-1.Also use of a polymer of formula (I) wherein M is aluminum as a catalyst in the production of glycol ethers by the reaction of an alkylene oxide and an alcohol.
    Type: Grant
    Filed: March 10, 1987
    Date of Patent: August 9, 1988
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4754075
    Abstract: Narrow, balanced alkoxylation product mixture distributions having at least one alkoxylation product constituting more than 20 weight percent of the mixture can be provided by modified, calcium-containing catalysts. Catalysts for alkoxylation processes can be produced from lime and can, with modification, be used to make the narrow, balanced alkoxylation product mixture distribution.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: June 28, 1988
    Assignee: Union Carbide Corporation
    Inventors: Robert J. Knopf, Louis F. Theiling, Jr.
  • Patent number: 4721816
    Abstract: Alkylene oxide adducts of higher alkanols are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an alkanol reactant comprising one or more C.sub.6 to C.sub.30 alkanols in the presence of a catalytically effective amount of a catalyst which combines (i) one or more sulfur-containing acids with (ii) one or more aluminum compounds selected from the group consisting of aluminum alcoholates and aluminum phenolates, the relative molar ratio of component (i) to component (ii) being in the range from about 0.1:1 to 1:1. Alkanol alkoxylates, and particularly alkanol ethoxylates, prepared in this manner are characterized by a relatively narrow-range distribution of alkylene oxide adducts and by a relatively low content of residual alkanol. The products of this process are nonionic surfactants, particularly useful as components of detergent formulations.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: January 26, 1988
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 4721579
    Abstract: A new type of ionic thickener for water-based products including functional fluids such as hydraulic fluids, cosmetic emulsions, etc. These new thickeners are prepared from polyoxyalklylene glycols, higher alkyl monoepoxides, lower alkyl monohalo lower alkyl carboxylates, and alkali metal hydroxide. These novel thickeners are generally characterized by the following formula: ##STR1## wherein R is a methylene or lower polymethylene group, R' is a higher alkyl group and R" is selected from the group consisting of oxyethylene groups and heteric or block copolymer mixtures of oxyethylene and other lower oxyalkylene groups, said copolymer containing at least 75 percent oxyethylene groups.
    Type: Grant
    Filed: August 15, 1980
    Date of Patent: January 26, 1988
    Assignee: BASF Corporation
    Inventor: Bongsub Kim