Organic Peracid Utilized Patents (Class 549/525)
  • Patent number: 6107433
    Abstract: A vegetable oil-based polyol is made by adding a peroxyacid to vegetable oil wherein said peroxyacid reacts with said vegetable oil to form epoxidized vegetable oil and adding said epoxidized vegetable oil to a mixture of an alcohol, water, and a catalytic amount of fluoboric acid so as to form a vegetable oil-based polyol. A further embodiment of the present invention involves making a vegetable oil-based polyol using an epoxidized vegetable oil as the starting material. The epoxidized vegetable oil undergoes hydroxylation by the same process as outlined above. According to another aspect of the present invention, the vegetable oil-based polyol formed by the novel methods of this invention may be reacted with an isocyanate to form a polyurethane. Alternatively, a filler such as silica may be combined with the vegetable oil-based polyol before it is reacted with the isocyanate. These polyurethanes made from vegetable oil-based polyols may be used to form electroinsulating casting resins.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: August 22, 2000
    Assignee: Pittsburg State University
    Inventors: Zoran Petrovic, Andrew Guo, Ivan Javni
  • Patent number: 6080894
    Abstract: The propylene oxide and styrene co-production process generates a heavy residue byproduct containing metals, mainly sodium, which previously was adequate for use only as low quality fuel. According to the invention, the heavy residue is dehydrated in the presence of a strong inorganic acid at temperatures of 150-250.degree. C. and pressures below the atmospheric pressure to yield styrene and recover 2-phenylethanol, a compound used in the perfume industry, and a heavy residue substantially free of metals that may be used as fuel.
    Type: Grant
    Filed: March 17, 1998
    Date of Patent: June 27, 2000
    Assignee: Repsol Quimica S.A.
    Inventors: Juan Antonio Delgado Oyague, Pilar De Frutos Escrig, Ignacio Vic Fernandez
  • Patent number: 6066751
    Abstract: It has been surprisingly discovered that the disadvantages of the lengthy literature procedures to synthesize 13,14-dihydro prostaglandin A, E, and F derivatives can be overcome using a novel Methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2 tetramethyl-1-silapropoxy)cyclopentyl) heptanoate intermediate, which can be synthesized from commercially available Methyl 7-[3-(R)-hydroxy-5-oxo-1-cyclopent-1-yl] heptanoate. This novel intermediate can be coupled with oxygen, carbon, sulfur, and nitrogen nucleophiles, in the presence of a base or a Lewis acid, in a ring-opening process to provide 13,14-dihydro prostaglandin A, E, and F derivatives.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: May 23, 2000
    Assignee: The Procter & Gamble Company
    Inventors: John August Wos, Jack Snyder Amburgey, Jr., Mitchell Anthony deLong, Yili Wang, Haiyan George Dai, Biswanath De
  • Patent number: 6063943
    Abstract: The present invention relates to a heterogeneous polyimide-supported transition metal complex catalyst for epoxidation of olefin, which is prepared by impregnating a heat- and acid-resistant polyimide resin with a homogeneous metal catalyst of molybdenum, vanadium, tungsten or titanium, and a process for preparing epoxy compounds using the same. The heterogeneous polyimide-supported transition metal complex catalyst of the invention provides superior catalytic activity, selectivity and stability in the epoxidation of higher olefin. Further, the catalyst of the invention has strong resistance against heat and acid. Besides, the catalyst of the invention may provide the following advantages which are critical in industrial use: it permits relatively high yield of epoxy compounds; and, it can be easily separated from the reaction product, which eases recycling of the catalyst.
    Type: Grant
    Filed: December 11, 1998
    Date of Patent: May 16, 2000
    Assignee: Korea Advanced Institute of Science and Technology
    Inventors: Son Ki Ihm, Chang Gun Oh, Jou Hyeon Ahn, Jong Chan Kim, David C. Sherrington
  • Patent number: 6008386
    Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.
    Type: Grant
    Filed: July 22, 1997
    Date of Patent: December 28, 1999
    Assignee: Board of Regents University of Nebraska-Lincoln
    Inventors: David B. Berkowitz, Michelle L. Pedersen
  • Patent number: 5808114
    Abstract: Preparation of epoxides from olefins by means of aromatic peroxycarboxylic acids comprises a step A of epoxidizing the olefin and removing the resulting aromatic carboxylic acid from the epoxide, a step B of catalytically hydrogenating the removed aromatic carboxylic acid to the corresponding aromatic aldehyde, and a step C of oxidizing this aldehyde with oxygen or an oxygen-containing gas mixture back to the aromatic peroxycarboxylic acid for re-use for epoxidizing an olefin.
    Type: Grant
    Filed: August 5, 1997
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim Henrique Teles, Werner Schnurr, Rolf Fischer, Norbert Rieber, Michael Schulz
  • Patent number: 5792878
    Abstract: A process for preparing chiral epoxides using chiral manganese triazanonane complexes as oxidation catalysts. These catalysts have the general formula?Mn.sub.u (L).sub.v (OR).sub.w (.mu.O).sub.x (.mu.OAc).sub.y !X.sub.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: August 11, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Matthias Beller, Ahmed Tafesh, Richard Walter Fischer, Bernd Scharbert
  • Patent number: 5756780
    Abstract: Disclosed are an improvement of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl(meth)acrylate, and a stabilized 3,4-epoxycyclohexyl methyl(meth)acrylate.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: May 26, 1998
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kyuichi Ohyama, Akira Horiguchi
  • Patent number: 5750741
    Abstract: A process for the preparation of an oxirane compound by reacting an olefinically unsaturated hydrocarbon with an organic hydroperoxide, in the presence of a catalyst comprising a titanasilsesquioxane of the general formula TiLR.sub.7 Si.sub.7 O.sub.12 and the structural formula ##STR1## wherein R is chosen from the group of cyclopentyl, cyclohexyl and cycloheptyl and L is chosen from the group of alkyl, cycloalkyl, alkylaryl, alkoxy, aryloxy, siloxy, amido and OH.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: May 12, 1998
    Assignee: Shell Oil Company
    Inventors: Mark Crocker, Rudolf Henri Max Herold
  • Patent number: 5705660
    Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: January 6, 1998
    Assignee: Board of Regents, University of Nebraska-Lincoln
    Inventors: David B. Berkowitz, Michelle L. Pedersen
  • Patent number: 5663393
    Abstract: Chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed, together with methods of using such catalysts. In accordance with one aspect of the invention, the catalyst is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of, producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 2, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
  • Patent number: 5637739
    Abstract: Methods of using chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed. In accordance with one aspect of the invention, the catalyst used is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: June 10, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
  • Patent number: 5633391
    Abstract: A process for the epoxidation of olefins comprises contacting the olefin with bis(trimethylsilyl)peroxide in the presence of a rhenium catalyst in an organic solvent.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: May 27, 1997
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Steven P. Fenelli
  • Patent number: 5620938
    Abstract: The invention relates to a catalyst for the epoxidation of alkenes using alkylhydroperoxide, the catalyst comprising an ion of one or more of the metals molybdenum, wolfram, titanium or vanadium on an inorganic carrier, characterised in that the metal ion is bound to the carrier via a polydentate organic ligand.The invention also relates to a process for the preparation of an alkene oxide by an alkene having 3 or more carbon atoms with an alkylhydroperoxide, using the catalyst described above.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: April 15, 1997
    Assignee: DSM N.V.
    Inventor: Otto E. Sielcken
  • Patent number: 5608088
    Abstract: A process for producing 3,4-caranediol of the formula [I] includes subjecting 3,4-epoxycarane, which is obtained by epoxidizing 3-carene under specific conditions, to a hydration reaction in the presence of a base catalyst in aqueous ethanol under pressure to obtain 3,4-caranediol.
    Type: Grant
    Filed: September 8, 1995
    Date of Patent: March 4, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keisuke Watanabe, Noboru Yamamoto, Atsushi Kaetsu, Yoshimi Yamada
  • Patent number: 5599955
    Abstract: The present invention provides an integrated process for the production of propylene oxide from an alternate feedstream such as synthesis gas. In the process, propylene oxide is produced from a feedstream comprising hydrogen and a carbon oxide. A portion of the feedstream is passed to an oxygenate production zone to produce an oxygenate stream comprising methanol and dimethyl ether, and the oxygenate stream is passed to an olefin production zone containing a metal aluminophosphate catalyst to produce a propylene stream. The propylene stream is epoxidized with hydrogen peroxide which has been produced from hydrogen separated from a portion of the feedstream. The spent water stream produced by the epoxidation reaction is treated to remove heavy components and returned to the hydrogen peroxide production zone. The return of the unreacted propylene from the epoxidation reaction zone for its subsequent recovery and recycle permits a less complicated, lower energy propylene separation.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: February 4, 1997
    Assignee: UOP
    Inventors: Bipin V. Vora, Peter R. Pujado
  • Patent number: 5578740
    Abstract: Epoxy-containing compounds which are essentially free of organic halides are prepared by (I) reacting an allyl derivative of an active hydrogen-containing compound with (II) a peroxygen-containing compound. The epoxy-containing compounds are useful in coatings, castings, laminates etc.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: November 26, 1996
    Assignee: The Dow Chemical Company
    Inventors: Andrew T. Au, J. Lowell Nafziger
  • Patent number: 5571907
    Abstract: A method for producing sucrose-based epoxy monomers having one to eight epoxy groups per molecule of sucrose, which comprises reacting a mixture comprising: a sucrose monomer having an allyl-containing group on at least one of the hydroxyl groups, and a reagent or catalyst selected from molybdenum, tungsten, vanadium, titanium and peracid, in the presence of hydrogen peroxide or a derivative thereof, in relative amounts sufficient to produce a sucrose-based epoxy monomer. Monomers thus produced are also provided. The sucrose-based epoxy monomers can be cured to produce a sucrose-based epoxy resin. Such resins are useful, for example, as adhesives, composites and coatings.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: November 5, 1996
    Assignee: Hawaiian Sugar Planters' Association
    Inventors: Navzer D. Sachinvala, Morton H. Litt
  • Patent number: 5569773
    Abstract: The present invention provides a composition represented by the formula ##STR1## (wherein x is an integer of 3 to 7, y is an integer of 0 to 50, and R.sub.a and R.sub.b are H, methyl group, or propyl group and each of the R.sub.a and R.sub.b groups may be replaced with any of the other groups simultaneously) and useful as a raw material or modifier for resins for use in coating compositions, adhesives, epoxy resins, and the like, and further provides a process for producing a composition comprising compounds represented by the above formula (I) which process is characterized in that a compound represented by the formula ##STR2## is reacted with a lactone at 30.degree. to 20.degree. C. or compounds represented by the formula ##STR3## (wherein x, y, R.sub.a, and R.sub.b have the meanings as defined above) are epoxidized at 0.degree. to 80.degree. C. using a peroxide.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: October 29, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Fujiwa, Tomohisa Isobe
  • Patent number: 5510428
    Abstract: Compositions (I), (II) and (III) comprising compounds having vinyl groups as side chains and epoxidized compositions (XI), (XII) and (XIII) thereof, which can be prepared by the various reaction combinations of (a) with (b) or (b)+(c), and or (d), where(a) is at least one compound having at least one vinyl group and one epoxy group in the molecule; (b) is at least one of a polybasic compound, an anhydride thereof, a polymer having carboxylic groups at terminals and a polymer having carboxylic groups as side chains; (c) is at least one organic compound having at least one active hydrogen atom; and (d) is at east one of an unsaturated monocarboxylic compound or an unsaturated monocarboxylic ester having a hydroxyl group.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: April 23, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshiyuki Harano, Sozo Namai, Katsuyuki Maeda, Takaaki Murai
  • Patent number: 5466835
    Abstract: The oxidation of olefinic compounds generally using hydroperoxides, especially aqueous solutions of hydrogen peroxide, can be effected in high yield and with good selectivity in the presence of a catalyst which is a mixture of small particles of titania and a titanosilicalite. Small particle size is essential in affording a catalyst with good activity and selectivity, with particle sizes no more than about 0.3 microns being the preferred mode of operation. Dilute aqueous hydrogen peroxide solutions may be used with good results. The resulting epoxidation, even when carried out at modest temperatures and with dilute aqueous hydrogen peroxide solutions, afford superior results in epoxidation relative to TS-1.
    Type: Grant
    Filed: May 9, 1994
    Date of Patent: November 14, 1995
    Assignee: UOP
    Inventors: Laszlo T. Nemeth, Thomas P. Malloy, Richard R. Jones
  • Patent number: 5440050
    Abstract: A process for the production of ambergris-type labdane spiroketals of general formulae I and II ##STR1## where R represents oxygen or sulphur, useful in the perfumery industry, the said process being characterized by the intramolecular cyclisation of the epoxyketone or its thio analog of general formula III ##STR2## where R.sub.1 represents COCH.sub.3 and R.sub.2 oxygen or sulphur.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: August 8, 1995
    Assignee: Givaudan-Roure Corporation
    Inventors: Maria do Ceu Goncalves da Costa, Maria J. V. de Oliveira Baptista Marcelo Curto, Maria R. de Loureiro da Silva Tavares da Rosa, William B. Motherwell
  • Patent number: 5382676
    Abstract: Disclosed are the improvements of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl(meth)acrylate and 3,4-epoxyeyclohexyl methyl(meth)acrylate which is prepared by the improvements, including only minor amounts of polymers having a low molecular weight composed of 3,4-epoxycyclohexyl methyl(meth)acrylate itself.Furthermore, disclosed is a 3,4-epoxycyclohexyl methyl(meth)acrylate composition which has an excellent resistance to coloring, including a specified organic phosphorous compound.
    Type: Grant
    Filed: August 19, 1993
    Date of Patent: January 17, 1995
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Akihiro Kuwana, Kimihide Honda, Kunio Koga
  • Patent number: 5378736
    Abstract: Disclosed are a composition and a process for preparation thereof, which composition comprises a novel alicyclic compound and an epoxidized compound thereof represented respectively by formulae (I) and (II) ##STR1## wherein Y.sup.1 represents at least one of the structural groups ##STR2## Y.sup.2 represents at least one of the the structural groups ##STR3## R.sup.a and R.sup.b each represent hydrogen or a methyl group, m represents a natural number of from 1 to 7, and n represents a natural number of from 1 to 20.The composition (II) is a multi-functional alicyclic epoxidized compound, which has a property of being high in epoxy group density in a molecule compared with alicyclic conventional epoxy resins, which can provide resins having wide range properties from being hard to being soft.
    Type: Grant
    Filed: May 30, 1991
    Date of Patent: January 3, 1995
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Fujiwa, Shoji Watanabe, Shin Takemoto, Yoshiyuki Harano
  • Patent number: 5354875
    Abstract: The oxidation of olefinic compounds generally using hydroperoxides, especially aqueous solutions of hydrogen peroxide, can be effected in high yield and with good selectivity in the presence of a titania-supported titanosilicate catalyst. Dilute aqueous hydrogen peroxide solutions may be used with good results. The resulting epoxidation, even when carried out at modest temperatures and with dilute aqueous hydrogen peroxide solutions, afford superior results in epoxidation relative to TS-1.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: October 11, 1994
    Assignee: UOP
    Inventors: Laszlo T. Nemeth, Thomas P. Malloy, Richard R. Jones
  • Patent number: 5331084
    Abstract: Fluorine-substituted epoxides of the formula ##STR1## in which the substituents R.sub.1 to R.sub.4, independently of one another, have the following meanings:R.sub.1 to R.sub.4 =H, fluorine, C.sub.1 - to C.sub.18 -alkyl in which some or all of the hydrogens may be substituted by fluorine, and at least one of the substituents R.sub.1 to R.sub.4 is a completely fluorinated alkyl or an alkyl of the formula--(CH.sub.2).sub.m --(C.sub.n F.sub.2n+1),in which m is 1 or 2, and n is an integer from 1 to 17, and x is 0 or 1.Furthermore, a method for the preparation of fluorine-substituted epoxides is described.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: July 19, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Kulpe, Heinz Strutz
  • Patent number: 5329024
    Abstract: A method for epoxidizing olefins is provided wherein an olefin and an oxygenating agent are contacted together in the presence of a manganese complex catalyst having at least one manganese atom coordinated with a nitrogen-containing ligand such that the manganese atom to coordinated nitrogen atom is 1:3 and thereafter isolating the resultant epoxide product. Catalyst compositions are also provided formed from the adsorption of the manganese complex catalyst onto a solvent insoluble support.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: July 12, 1994
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Sharon H. Jureller, Judith L. Kerschner, Robert Humphreys
  • Patent number: 5319113
    Abstract: The invention relates to new, liquid crystalline di(alkoxyglycidyl) compounds of optionally ring substituted 1,4-dibenzoyloxybenzenes in which an alkoxy group consisting of 2 to 8 carbon atoms is incorporated between the glycidyl groups and the 1,4-dibenzoyloxybenzene, a synthesis of 4,4'-di(hexoxyglycidyl)-(1,4-dibenzoyloxybenzene), furthermore epoxy resin mixtures containing the new dialkoxyglycidyl compounds and the epoxy resin mixtures thereof in curable mixtures.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: June 7, 1994
    Assignee: The Aerospace Corporation
    Inventors: Joseph J. Mallon, Paul M. Adams
  • Patent number: 5276235
    Abstract: In the co-production of propylene oxide and styrene monomer, there is produced a sodium-containing heavy residue stream previously suitable only as a low grade fuel. In accordance with the invention, the heavy residue stream is contacted with acid having a molar concentration with respect to water above that which corresponds to the product salt solubility limit, and the resulting mixture is phase separated into an aqueous sodium salt-containing slurry phase and an organic phase reduced in sodium.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: January 4, 1994
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Walter S. Dubner
  • Patent number: 5268489
    Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: December 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
  • Patent number: 5237076
    Abstract: The invention relates to new, liquid crystalline di(alkoxyglycidyl) compounds of optionally ring substituted 1,4-dibenzoyloxybenzenes in which an alkoxy group consisting of 2 to 8 carbon atoms is incorporated between the glycidyl groups and the 1,4-dibenzoyloxybenzene, a synthesis of 4,4'-di(hexoxyglycidyl)-(1,4-dibenzoyloxybenzene), furthermore epoxy resin mixtures containing the new dialkoxyglycidyl compounds and the epoxy resin mixtures thereof in curable mixtures.
    Type: Grant
    Filed: August 28, 1992
    Date of Patent: August 17, 1993
    Assignee: The Aerospace Corporation
    Inventors: Joseph J. Mallon, Paul M. Adams
  • Patent number: 5169965
    Abstract: A composition comprising a lactone-modified alicyclic compound (I), or an epoxidized lactone-modified alicyclic compound (II) of the following formulae: ##STR1## wherein R is an alkyl group, an aromatic group or an alkenyl group having carbon number of from 1 to 30, Y.sup.1 is at least one of the structural groups; ##STR2## Y.sup.2 is at least one of the structural group; ##STR3## X is the structural group; ##STR4## R.sup.4 and R.sup.b each independently is hydrogen or a methyl group, c and c' represent a number of from 4 to 8, from n1 to nL represents 0 or a number of more than 0, respectively, and n1+n2+n3+. . . +nL corresponds to the total mole numbers of a lactone introduced into one molecule.These compositions can be made into a heat-curable composition, a photo-curable composition, a polymerizable composition and another photo-curable composition.
    Type: Grant
    Filed: July 10, 1991
    Date of Patent: December 8, 1992
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Fujiwa, Shin Takemoto, Tomohisa Isobe, Yoshiyuki Harano
  • Patent number: 5151450
    Abstract: There are provided 4,5-Dihydroxy-2,6,6-trimethyl-2-cyclohepten-1-one, a method for preparing the same and an antiulcer agent containing the same as an effective ingredient.
    Type: Grant
    Filed: February 21, 1991
    Date of Patent: September 29, 1992
    Assignee: Tokyo Tanabe Company, Limited
    Inventors: Kiyokazu Murakami, Susumu Yokura
  • Patent number: 5128492
    Abstract: An epoxidation reaction product formed by the molybdenum catalyzed reaction of propylene with tertiary butyl hydroperoxide to provide propylene oxide and tertiary butyl alcohol is separated by distillation into a propylene fraction, a propylene oxide fraction, a tertiary butyl alcohol fraction and a heavy liquid distillation fraction composed primarily of tertiary butyl hydroperoxide, tertiary butyl alcohol, dissolved molybdenum catalyst, and impurities including lower aliphatic C.sub.1 -C.sub.4 carboxylic acids, and the heavy liquid distillation fraction is saturated with hydrogen to precipitate the molybdenum therefrom for recovery.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: July 7, 1992
    Assignee: Texaco Chemical Company
    Inventors: William A. Smith, Robert A. Meyer, Edward T. Marquis
  • Patent number: 5101051
    Abstract: Epoxides are prepared by reaction of compounds containing olefinic unsaturation, for example .alpha.-olefins, terpenes and steroids, with an aliphatic diperoxydicarboxylic acid. The diperoxydicarboxylic acid contains 2 to 16 carbon atoms and suitably at least 6 carbon atoms. The process gives a good epoxidation process and does not give rise to byproduct formation.
    Type: Grant
    Filed: May 2, 1991
    Date of Patent: March 31, 1992
    Assignee: Eka Nobel
    Inventors: Harriet Ericsson, Elina Sandberg, Eva Gottberg-Klingskog
  • Patent number: 4946973
    Abstract: The stereoselective expoxidation of cyclic 4-hydroxy olefins is disclosed. These methods involve contacting the cyclic 4-hydroxy olefin with peroxycarboximidic acid, which is preferably generated in situ by contacting an organic nitrile with aqueous hydrogen peroxide. The invention provides unexpectedly high yields of the corresponding cis-epoxides.
    Type: Grant
    Filed: September 20, 1988
    Date of Patent: August 7, 1990
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4921983
    Abstract: In the continuous epoxidation of olefins with percarboxylic acids, the alkane component which normally accumulates during the circulation of the olefin is reduced by branching off a partial current from the recycled olefin and by additional epoxidation of this olefin with percarboxylic acids as well as a subsequent separation from the epoxide.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: May 1, 1990
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Willi Hofen, Gunter Prescher, Helmut Maurer
  • Patent number: 4882442
    Abstract: Process for the production of epoxides by reaction of one mol equivalent of the corresponding olefins with 1 to 2.6 mols equivalent aliphatic percarboxylic acids with 2-4 C atoms containing at least one strong acid, wherein the strong acid in the percarboxylic acid mixture is neutralized with an at least equivalent amount of an inorganic base and thereafter the percarboxylic acid mixture is combined with a reaction mixture containing the olefin, about 0.5 to about 0.74 equivalents acid-binding agent with reference to the amount of total carboxylic acid present in the percarboxylic acid mixture and, if necessary, solvent.
    Type: Grant
    Filed: January 27, 1988
    Date of Patent: November 21, 1989
    Assignee: Peroxid-Chemie GmbH
    Inventors: Wolfgang Edl, Gunter R. Sienel
  • Patent number: 4855465
    Abstract: Aliphatic epoxides of the formula: ##STR1## can be prepared in a technically efficient manner from the corresponding olefins by means of perpropionic acid in a benzene solution. The benzene solution can also be 1.5 weight percent of hydrogen peroxide, 1.5 weight percent of water and about 800 ppm of mineral acid.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: August 8, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Andreas Grund, Guenter Prescher, Georg Boehme, Willi Hofen, Heinrich Petsch
  • Patent number: 4851594
    Abstract: Novel substituted styrene compounds of the formula ##STR1## wherein R is halogen or --CF.sub.3 ; n is an integer from 0 to 5; and X.sub.1, X.sub.2, X.sub.3, X.sub.4 and X.sub.5 are halogen, and are useful as intermediates for preparing herbicidal compounds.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: July 25, 1989
    Assignee: The Dow Chemical Company
    Inventor: R. Garth Pews
  • Patent number: 4851556
    Abstract: Epoxidized polybutadienes with an average molecular weight of 500 to 100,000 and a certain content of epoxide oxygen were prepared from the corresponding polybutadienes with use of perpropionic acid in a benzene solution. The solution can also be employed in unpurified form with maximum contents of 1.5 weight percent hydrogen peroxide 1.5 weight percent of water, and about 800 ppm of mineral acid.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: July 25, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Andreas Grund, Guenter Prescher, Udo Brandt
  • Patent number: 4849532
    Abstract: The diepoxide of the formula: ##STR1## can be prepared from the corresponding diolefin in a technically simple manner by means of perpropionic acid in a benzene solution. The solution can also be employed in unpurified form with certain maximum contents of 1.5 weight percent of hydrogen peroxide, 1.5 weight percent of water, and of about 800 ppm of mineral acid.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: July 18, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Georg Boehme, Willi Hofen, Andreas Grund, Heinrich Petsch, Guenter Prescher
  • Patent number: 4788303
    Abstract: A process is disclosed for preparation of novel epoxy-substituted aralkyl isocyanates by reaction of tertiary aralkyl olefins and an epoxidizing agent at a temperature of from -35.degree. C. to about 50.degree. C. The compounds are useful as intermediates to produce curing agents for polyfunctional active hydrogen-containing compounds, e.g., by reaction with polyols to produce epoxy-pendant urethanes and then with polyamines, and the like.
    Type: Grant
    Filed: December 14, 1987
    Date of Patent: November 29, 1988
    Assignee: American Cyanamid Company
    Inventor: Paul S. Waterman
  • Patent number: 4772733
    Abstract: An epoxy-sulfonylazide having the general formula ##STR1## wherein R is lower alkyl and R' is hydrogen or lower alkyl.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: September 20, 1988
    Assignee: Hercules Incorporated
    Inventor: Anthony B. Clayton
  • Patent number: 4724031
    Abstract: 2,6-Disubstituted 4-epoxypropyl glycidyl ethers of the formula ##STR1## wherein X is a group R' or X is a group of the formula ##STR2## and each of R and R' independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, a halogen atom or C.sub.6 -C.sub.10 aryl, can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for application in the electronics industry, or as adhesives. Compounds of the formula are also valuable reactive diluents for curable epoxy resin mixtures.
    Type: Grant
    Filed: June 4, 1986
    Date of Patent: February 9, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles E. Monnier, Sheik Abdul-Cader Zahir, Sameer H. Eldin
  • Patent number: 4723038
    Abstract: Processes for preparing compounds which exhibit seed germinating activity are disclosed. An ester of acetoacetic acid is condensed with a ketone to produce a substituted cyclohexenone which is reacted with a thiol to get a dithioketal which is then desulfurized to produce an ester of a substituted cyclohex-2-ene-1-carboxylic acid which exhibits seed germinating activity. The same compound can be produced by a different process which reacts the substituted cyclohexenone with a reducing agent. An exemplary reducing agent would be an organosilane and a Lewis acid.
    Type: Grant
    Filed: December 31, 1985
    Date of Patent: February 2, 1988
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Oliver D. Dailey, Jr.
  • Patent number: 4717771
    Abstract: 2,3-Epoxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone, an epoxy ketone of formula ##STR1## possesses useful fragrance characters and, consequently, it can be used advantageously in the manufacture of perfume, perfume bases and perfumed products. It develops a flowery and fruity odor.
    Type: Grant
    Filed: October 4, 1985
    Date of Patent: January 5, 1988
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Dietrich Kastner
  • Patent number: 4647678
    Abstract: The epoxidation of terminally and/or internally olefinically unsaturated hydrocarbon compounds which are liquid at 50.degree. to 100.degree. C. and at atmospheric pressure (oil phase), in which the oil phase is treated with an acid phase containing acetic acid, hydrogen peroxide and peracetic acid in aqueous solution, after which the aqueous acid phase is separated from the oil phase, the peracetic acid in the aqueous acid phase is regenerated and the regenerated aqueous acid phase is returned to the epoxidation reactor. Epoxidation is carried out using an aqueous acid phase containing at most about 10% by weight of peracetic acid, and the peracetic acid content in the aqueous acid phase is reduced by at most about 50%, based on the peracetic acid content of the aqueous acid phase used, after a single passage through the epoxidation stage. After separation from the oil phase, the aqueous acid phase preferably is cooled before regeneration.
    Type: Grant
    Filed: December 26, 1985
    Date of Patent: March 3, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Klemens Eckwert, Lutz Jeromin, Alfred Meffert, Eberhard Peukert, Bernhard Gutsche
  • Patent number: 4611070
    Abstract: Dye-forming components of the general formula ##STR1## where A is the radical of a fused benzo ring or 2,1-naphthalene ring, and either radical may be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro, chlorine, bromine or C.sub.1 -C.sub.6 -alkoxycarbonyl, R.sup.1 is C.sub.1 -C.sub.16 -alkyl, C.sub.7 -C.sub.10 -phenylalkyl or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine or bromine, and R.sup.2 and R.sup.3 independently of one another are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.4 -alkyl, which is substituted by cyano, chlorine, methoxy or ethoxy, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.7 -C.sub.10 -phenylalkyl or trimethylene which is unsubstituted or substituted by 1, 2 or 3 methyl groups and is bonded to the carbon in the 6- and/or 8-position of the benzo ring, or R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is phenyl which is unsubstituted or substituted by chlorine, bromine, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 4, 1982
    Date of Patent: September 9, 1986
    Assignee: BASF Aktiengesellschaft
    Inventor: Andreas Oberlinner
  • Patent number: 4607113
    Abstract: Production of novel molybdenum dioxo dialkyleneglycolate compositions, especially adapted for use as catalysts in the epoxidation of olefinic compounds with an organic hydroperoxide, by reaction of molybdenum trioxide with particular dialkylene glycol compounds at specified elevated temperatures while removing water.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: August 19, 1986
    Assignee: Atlantic Richfield Company
    Inventors: Wilfred P. Shum, Charles F. Cooper