Patents Examined by Joseph E. Evans
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Patent number: 5527927Abstract: There are disclosed a process for producing glycidyl acrylate or glycidyl methacrylate by the transesterification of glycidol and methyl methacrylate, etc. which process comprises carrying out the transesterification in the presence of a polymerization inhibitor by using, as a catalyst, a quaternary ammonium salt represented by the general formula (I) or a quaternary phosphonium salt represented by the general formula (II)(R.sup.1 R.sup.2 R.sup.3 R.sup.4)NX (I)(R.sup.1 R.sup.2 R.sup.3 R.sup.4)PX (II)wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each an alkyl group having 1 to 20 carbon atoms, or the like, and X is a cyanide ion, cyanate ion or the like to complete the reaction; thereafter arresting the reaction by adding a catalyst deactivator represented by the general formula (III)SB (iii)wherein S is a sulfonic acid or a heteropolyacid and B is an alkali metal excluding potassium or an alkaline earth metal; and distilling away unreacted methyl methacrylate, etc.Type: GrantFiled: May 10, 1995Date of Patent: June 18, 1996Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masahiro Kurokawa, Akihiro Honma, Tsuyoshi Isozaki
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Patent number: 5527969Abstract: A process for preparing acetaldehyde diethyl acetal is provided which involves:reacting acetaldehyde with ethanol in the presence of an acid catalyst and in the presence of an entrainer having a boiling point of from 25.degree. to 75.degree. C.Type: GrantFiled: February 7, 1995Date of Patent: June 18, 1996Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Moustafa El-Chahawi
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Patent number: 5525728Abstract: A process for the production of sclareolide comprising the steps of: (1) providing an aqueous composition comprised of: (a) water; (b) sclareol, abienol, or a mixture of sclareol and abienol, (c) an effective amount of a ruthenium catalyst; and, (d) an emulsifying agent; (2) forming an aqueous alkaline composition by adding an alkali metal hydroxide to said aqueous composition; (3) reacting said aqueous alkaline composition with an oxidizing agent to form a crude product; andeither: (4) further reacting said crude product with base to form the salt of 8.alpha.-hydroxy-11-carboxyl-12, 13, 14, 15, 16-pentanorlabdane and; (5) reacting said salt with acid to form sclareolide;or: (4) heating said crude product to form sclareolide.Type: GrantFiled: October 17, 1994Date of Patent: June 11, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Markus Schneider, Theo Stalberg, Thomas Gerke
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Patent number: 5525741Abstract: A process for producing an olefin oxide comprising oxidizing a corresponding lower olefin with molecular oxygen in the gas phase in the presence of a crystalline metallosilicate having supported thereon at least one salt selected from the group consisting of alkali metal salts of nitric acid, alkaline earth metal salts of nitric acid, silver salts of nitric acid and silver salts of nitrous acid. Said process can produce an olefin oxide at a high selectivity.Type: GrantFiled: April 24, 1995Date of Patent: June 11, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Keisuke Sugita, Toshikazu Yagi
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Patent number: 5525732Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.Type: GrantFiled: May 31, 1995Date of Patent: June 11, 1996Assignee: Ciba-Geigy CorporationInventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
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Patent number: 5523426Abstract: Epoxides are produced by an integrated process involving molecular oxygen oxidation of a secondary alcohol, separation of the ketone by-product, and epoxidation of an olefin in the presence of a titanium silicalite catalyst and a diluent, wherein a crude alcohol stream obtained by removing epoxide from the epoxidation product mixture serves as the diluent. Despite use of the crude alcohol stream, which typically comprises water, organic acids and glycols, high selectivities to epoxides such as propylene oxide are realized.Type: GrantFiled: January 4, 1995Date of Patent: June 4, 1996Assignee: ARCO Chemical Technology, L.P.Inventors: John C. Jubin, Jr., Guy L. Crocco, John G. Zajacek
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Patent number: 5523425Abstract: In a process for producing a chlorohydrin an olefinically unsaturated compound is reacted with chlorine in the presence of water. Water is applied as a film on a solid support in a reaction zone and/or water droplets are dispersed in the reaction zone. The reaction is conducted at a pressure of up to about 10 bar.Type: GrantFiled: December 21, 1994Date of Patent: June 4, 1996Assignee: The Dow Chemical CompanyInventors: Gunther A. Pech, Werner J. Witzl
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Patent number: 5519152Abstract: A process of manufacturing ethylene oxide is presented in ethylene and free oxygen are reacted in the presence of methane, carbon dioxide, and argon in a reactor to form an effluent comprising ethylene oxide; the effluent is then withdrawn and ethylene oxide is removed from the effluent to obtain a recycle stream; carbon dioxide and argon are removed from the recycle stream to obtain a treated recycle stream which is supplied to the reactor along with additional reactants and methane, wherein removing argon comprises separating a side stream from the recycle stream, passing the side stream to the feed inlet of a membrane unit, removing an argon-containing stream from the permeate outlet of the membrane unit, removing a retentate stream from the retentate outlet of the membrane unit, adding the retentate stream to the recycle stream, and purging the permeate side of the membrane unit with inert gas.Type: GrantFiled: April 5, 1995Date of Patent: May 21, 1996Assignee: Shell Oil CompanyInventor: Jeffrey P. Gorcester
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Patent number: 5516951Abstract: 1,1,1,4,4,4-Hexafluoro-2-butene is prepared by reacting 1,1,1-trifluoro-2,2-dichloroethane with copper and an amine, and then 1,1,1,4,4,4-hexafluorobutane is prepared by reacting 1,1,1,4,4,4-hexafluoro-2-butene with hydrogen.1,1,1,4,4,4-Hexafluorobutane, which is used as a coolant, a blowing agent or a cleaner and can reserves the environment, is easily obtained, and 1,1,1,4,4,4-hexafluoro-2-butene, which is useful as an intermediate for the 1,1,1,4,4,4-hexafluorobutane, or as a monomer of fluorine-containing polymers is easily prepared in a good yield.Type: GrantFiled: May 19, 1995Date of Patent: May 14, 1996Assignee: Daikin Industries Ltd.Inventor: Hirokazu Aoyama
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Patent number: 5514818Abstract: A method of resolving a mixture of stereoisomers of an aliphatic epoxide containing two or less oxygen atoms is provided. The method comprises utilizing a polysaccharide or a derivative thereof as a resolving agent.Type: GrantFiled: February 10, 1995Date of Patent: May 7, 1996Assignee: Daicel Chemical Industries, Ltd.Inventor: Kozo Tachibana
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Patent number: 5510542Abstract: A process for producing diglycerin having a low content of cyclic components by reacting glycerin with epichlorohydrin by a continuous process in which the epichlorohydrin required for the reaction is introduced into at least one flow reactor at several separate spots or reaction zones mutually separated in space in the direction of flow; the reacted reaction mixture is substantially freed of excess glycerin in at least one evaporator; the remaining chlorohydrin/ether mixture is hydrolyzed in at least one first step with a 5 to 40 mole % excess alkali carbonate solution, calculated with respect to organically bound chlorine in the chlorohydrin ether, at a pH of 6.5 to 9.5, and hydrolysis is at least substantially completed in a second step with an alkali hydroxide at a pH above 10; the resulting hydrolyzed crude product solution is adjusted to a pH of 5.Type: GrantFiled: February 24, 1995Date of Patent: April 23, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Gerald Jakobson, Werner Siemanowski
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Patent number: 5508446Abstract: A method for producing an alkyl 3-phthalidylideneacetate has the step of treating phthalic anhydride with a monoalkyl malonate or a salt thereof having the following formula:MOCO--CH.sub.2 --COOR,wherein M represents a hydrogen atom, K, Na, Li, or NH.sub.4, and R represents a lower alkyl group having 1 to 5 carbon atoms. By using the above method, the desired alkyl 3-phthalidylideneacetate can be obtained at a high yield.Type: GrantFiled: October 3, 1994Date of Patent: April 16, 1996Assignee: Sumika Fine Chemicals Co., Ltd.Inventor: Taketo Hayashi
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Patent number: 5504239Abstract: A first alkanol having from 1 to 3 carbon atoms can be separated off from other organic compounds of higher carbon number from the group comprising other alcohols, polyalcohols, ethers, oxo compounds, esters of carboxylic acids and of carbonic acid, haloaliphatics, amines, amides, hydrocarbons, carboxylic acids and nitriles, which in each case have at least 1 carbon atom more than the first alkanol, where in the case of halogenoaliphatics, halogen substituents are counted as further carbon atoms, by permeation on membranes, if a water content from 1 to 30% by weight, preferably from 5 to 15% by weight, based on the amount of mixture and water, is maintained.Type: GrantFiled: June 7, 1994Date of Patent: April 2, 1996Assignee: Bayer AktiengesellschaftInventors: Wolf Mehl, Wolfgang Scheinert, Ingo Janisch, Andreas Groschl
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Patent number: 5503813Abstract: Epoxidate from the molybdenum catalyzed epoxidation of an olefin such as propylene with a hydroperoxide such as ethylbenzene hydroperoxide is treated with 2 to 15 times the stoichiometric equivalent of aqueous base such as sodium hydroxide to form Na.sub.2 MoO.sub.4 and the resulting mixture is phase separated to separate an organic phase reduced in molybdenum and a net aqueous stream containing removed molybdenum, the mass ratio of the organic phase to the net aqueous stream being 450-3,000/I.Type: GrantFiled: May 12, 1995Date of Patent: April 2, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: Thomas I. Evans
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Patent number: 5504255Abstract: The present invention provides special epoxy derivative (1), cyclohexanone derivative (2), cyclohexenone derivative (3) and 3-substituted cyclohexenone derivative (4) which are useful as intermediates for synthesizing physiologically active materials, and a method for stereoselectively introducing substituted groups. Further, the present invention provides a method for synthesizing optically active compounds, such as optically active carvone via these intermediates.Type: GrantFiled: May 15, 1995Date of Patent: April 2, 1996Assignee: Chisso CorporationInventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5495050Abstract: A method for producing high purity chloroaldehyde monomers at a high yield by depolymerization of a chloroaldehyde cyclic trimer represented by the following formula, ##STR1## wherein R is a hydrogen atom, methyl group, or an ethyl group. The depolymerization reaction can be carried out in the presence of activated clay. Said chloroaldehyde cyclic trimer can be stored in a stable manner and chloroaldehyde monomers obtained by the depolymerization can be used as are as a raw material for the synthetic reaction of chloroaldehyde derivatives.Type: GrantFiled: October 20, 1994Date of Patent: February 27, 1996Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
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Patent number: 5495052Abstract: A tertiary amine is used to catalize the stereospecific ring-opening of chiral glycidol with o-methoxyphenol to afford high yields of enantiomerically enriched guaifenesin. The optical purity of the product may be even further enhanced by recrystallization.Type: GrantFiled: September 29, 1994Date of Patent: February 27, 1996Assignee: Arco Chemical Technology, L.P.Inventors: Wilfred P. Shum, Harry Mazurek, Jian Chen
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Patent number: 5495051Abstract: A phenolic allyl ether is provided which can be prepared by reacting a polyphenol with an allyl halide, said polyphenol described by the formula ##STR1## in which Ar is an aromatic moiety, L is a divalent cyclohexanenorbornane linking moiety, L' is a divalent cycloaliphatic moiety, Allyl is a phenolic allyl ether group, and each of m and n is a number within the range of 0 to about 10. Such phenolic allyl ethers include the reaction product of allyl halide with the product of the addition reaction of a phenol and a cyclohexenenorbornene compound such as 5-(3-cyclohexen-1-yl)bicyclo[2.2.1]hept-2-ene. The resulting phenolic allyl ether resins are useful as processing agents for polymaleimides.Type: GrantFiled: August 22, 1994Date of Patent: February 27, 1996Assignee: Shell Oil CompanyInventors: Pen-Chung Wang, Donald R. Kelsey
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Patent number: 5493035Abstract: Activated carbon to be used in the removal of impurities from propylene oxide is first pre-wetted with a glycol such as propylene glycol; after bed deactivation, water containing a basic catalyst is added to hydrolyze propylene oxide and to form a non-hazardous slurry of carbon, propylene glycol and water.Type: GrantFiled: March 24, 1995Date of Patent: February 20, 1996Assignee: Arco Chemical Technology, L.P.Inventors: Ahmad Soltani-Ahmadi, Thomas C. Mullin
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Patent number: 5493064Abstract: The present invention discloses an alcohol coupling process in which a vaporized mixture of starting alcohols, preferably methanol and ethanol, is reacted with syngas in the presence of a large pore L zeolite, Y zeolite or large port mordenite, to form at least one alcohol coupling product having a greater number of carbon atoms than all of the starting alcohols. The large pore zeolite preferably has a substantial absence of strongly acidic catalytic sites and the reaction preferably produces the product alcohol in the substantial absence of C.sub.6+ oxygenates.Type: GrantFiled: December 13, 1994Date of Patent: February 20, 1996Assignee: Exxon Research and Engineering CompanyInventors: Thomas H. Vanderspurt, Jar-Lin Kao