Patents Examined by Karl J. Puttlitz, Jr.
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Patent number: 5767326Abstract: A process for preparing hydroxymethylcyclopropane, in which formylcyclopropane is hydrogenated over copper chromite, zinc chromite and/or copper/zinc catalysts. The process may be batchwise or continuous.Type: GrantFiled: March 7, 1997Date of Patent: June 16, 1998Assignee: Huels AktiengesellschaftInventors: Wolfgang Kleemiss, Marcel Feld
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Patent number: 5766514Abstract: A method of storing and transporting acetylene comprises mixing acetylene gas and carbon dioxide gas and then reducing the temperature of the gas mixture thus obtained to obtain either a liquid-vapour or solid-vapour mixture and storing the liquid-vapour mixture or solid-vapour mixture in a pressure vessel.Type: GrantFiled: March 7, 1996Date of Patent: June 16, 1998Assignee: The BOC Group plcInventors: Silvia Beatriz Dougill, Wasyl Michael Sajik, Shuen-Cheng Hwang
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Patent number: 5767328Abstract: A process for producing a cyclic alcohol which comprises subjecting a cyclic olefin represented by the formula: C.sub.n H.sub.2n-2-m R.sub.m (wherein R represents a hydrogen atom, an alkyl group of 1-4 carbon atoms, a phenyl group or a cyclohexyl group, n represents an integer of 5-12, and m represents an integer of 1-4) to a catalytic hydration reaction with water in the presence of a crystalline aluminosilicate having a primary particle diameter of 0.5 .mu.m or less as a catalyst, extracting the resulting liquid of an oil phase containing a cyclic alcohol and the crystalline aluminosilicate, evaporating the liquid and feeding the vapor to a rectifying column and/or filtering the liquid and feeding the filtrate to the rectifying column, thereby to adjust the concentration of the crystalline aluminosilicate contained in the liquid in the rectifying column to 1000 ppm by weight or less, and subjecting the liquid to distillation to separate the cyclic alcohol.Type: GrantFiled: December 19, 1996Date of Patent: June 16, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shigeru Ono, Mineyuki Iwasaki
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Patent number: 5763664Abstract: A process for preparing a cyclopentenone by forming a two-phase mixture of a 1,4-diketone, a water immiscible organic solvent, and an aqueous base solution, and heating the mixture so as to convert the 1,4-diketone to a cyclopentenone which collects in the organic solvent phase.Type: GrantFiled: December 1, 1995Date of Patent: June 9, 1998Assignee: Albemarle CorporationInventor: Paul C. Saunders
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Patent number: 5763686Abstract: 1,1,1-Tris(4-hydroxyphenyl)ethane, a branching agent for polycarbonates, is prepared by the reaction of phenol with 2,4-pentanedione in the presence of sulfuric acid and at least one mercapto sulfonic acid such as 3-mercaptopropanesulfonic acid as promoter. By employing specific proportions of the promoter and sulfuric acid, high product yields can be obtained in relatively short times.Type: GrantFiled: December 16, 1996Date of Patent: June 9, 1998Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Eric James Pressman
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Patent number: 5763675Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting a magnesium bis-hydrocarbyloxide, derived at least in part from a hydroxyaromatic compound having at least one free position ortho to the hydroxyl group, with formaldehyde or a formaldehyde-liberating compound under substantially anhydrous conditions at a pressure of from 50 to 700 mm Hg absolute.Type: GrantFiled: January 5, 1996Date of Patent: June 9, 1998Assignee: Zeneca LimitedInventor: Daniel Levin
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Patent number: 5763687Abstract: An improved preparation process for an aromatic mononitro compound comprising reacting an aromatic compound with mixed acid consisting of nitric acid, sulfuric acid or phosphoric acid and water, wherein these flow to react with each other in a reactor comprising a tube inside of which more than one twisted tabular members are aligned in sequence in a manner that a front margin of a twisted tabular member is substantially perpendicular to an back margin of the preceding member, can resolve a number of problems such as an inadequate mixing efficiency, reduction of a reaction rate, associated voluminal increase/complication of a reactor and difficulty in securing safety as well as provide the aromatic mononitro compound with minimal amount of by-products in a considerably short period.Type: GrantFiled: December 10, 1996Date of Patent: June 9, 1998Assignee: Mitsui Chemicals, Inc.Inventors: Jyoji Morisaki, Masaaki Iijima, Kouki Oogaki, Hiroaki Matsuno, Takashi Yamaguchi, Katsuharu Miyata
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Patent number: 5756864Abstract: A process is described for preparing D,L-menthol by catalytic rearrangement of optically active D-menthol in the presence of hydrogen at temperatures of from 200 to 350.degree. C. and under pressures of from 50 to 350 bar over fixed-bed catalysts comprising support-free reduced shaped bodies of pressed powders of nickel, manganese, alkaline earth metal (hydr)oxides and optionally (hydr)oxides of elements of transition groups V and/or VI of the Periodic Table.Type: GrantFiled: May 10, 1996Date of Patent: May 26, 1998Assignee: Bayer AktiengesellschaftInventors: Gerhard Darsow, Gerd-Michael Petruck
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Patent number: 5756859Abstract: 1,1,1-Tris(4-hydroxyphenyl)ethane in admixture with bisphenol A is obtained by the reaction of 2,4-pentanedione with excess phenol under acidic conditions and in the presence of a mercapto compound as promoter. The products may be separated by extracting bisphenol A with a chlorinated alkane. Purification of the resulting 1,1,1-tris(4-hydroxyphenyl)ethane is achieved by slurrying in and/or recrystallization from methanol-water, optionally with addition of an alkali metal borohydride or dithionite.Type: GrantFiled: December 4, 1996Date of Patent: May 26, 1998Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Paul Dean Sybert, Julia Lam Lee, David Michel Dardaris
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Patent number: 5756821Abstract: Open-chain branched olefinically unsaturated alcohols and esters are excellent aroma substances.Type: GrantFiled: August 30, 1996Date of Patent: May 26, 1998Assignee: Haarmann & Reimer GmbHInventors: Erich Dilk, Peter Worner
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Patent number: 5756866Abstract: The process claimed enables three separate streams to be obtained, from mixtures containing methanol, ethanol, n-propanol, isobutanol, water and other both low- and high-boiling compounds, of which one is anhydrous basically consisting of methanol and ethanol (I), one containing most of the n-propanol present in the mixture fed (II), together with small quantities of methanol, ethanol, isobutanol and water, and one containing most of the isobutanol and high-boiling compounds present in the above mixture (III), by the use of three rectifying columns, stream (I) being taken from a lateral point of the first column, stream (II) obtained from the head of the second column, stream (III) obtained from the bottom of the second column.Type: GrantFiled: December 8, 1995Date of Patent: May 26, 1998Assignee: Agip Petroli S.p.A.Inventors: Carlo Rescalli, Ugo Melis
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Patent number: 5750803Abstract: A continuous process is described for the preparation of D,L-menthol by catalytic hydrogenation of compounds which have the carbon skeleton of p-menthane containing at least one double bond and are 3-substituted by oxygen using hydrogen and/or by rearrangement of stereoisomers of menthol in the presence of hydrogen at temperatures of 150.degree. to 230.degree. C. and at pressures of 25 to 350 bar on fixed-bed catalysts made of support-free reduced shaped bodies made of pressed powders of cobalt (hydr)oxide, manganese (hydr)oxide, alkaline earth metal (hydr)oxides and, optionally, (hydr)oxides of elements of subgroup V and/or VI of the Periodic Table of the Elements.Type: GrantFiled: May 10, 1996Date of Patent: May 12, 1998Assignee: Bayer AktiengesellschaftInventors: Gerhard Darsow, Gerd-Michael Petruck
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Patent number: 5750795Abstract: The present invention provides a process for producing a ketone represented by a general formula RCOR' (wherein R is a C.sub.1 -C.sub.17 alkyl group, a C.sub.7 -C.sub.12 aralkyl group, a C.sub.7 -C.sub.12 aryl group or a C.sub.5 -C.sub.8 cycloalkyl group; R' is a C.sub.1 -C.sub.17 alkyl group, a C.sub.7 -C.sub.12 aralkyl group, a C.sub.7 -C.sub.12 aryl group or a C.sub.5 -C.sub.8 cycloalkyl group; R and R' may the same), which process comprises reacting a carboxylic acid represented by a general formula RCOOH (wherein R has the same definition as given above) with a carboxylic acid represented by a general formula R'COOH (wherein R' has the same definition as given above) in a gas phase in the presence of a catalyst containing at least either of MgO and CaO.The process allows for production of an intended ketone at a high yield at high productivity.Type: GrantFiled: January 26, 1996Date of Patent: May 12, 1998Assignee: Nippon Shokubai, Ltd.Inventor: Noboru Saito
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Patent number: 5750805Abstract: Epoxides containing hydroxy groups are rearranged enantioselectively using a chiral base to give allyl alcohols in high enantiomeric excess, e.g. ##STR1## If R.sup.3 .noteq.H, the reaction also has the effect of generating a chiral tetrasubstituted carbon atom.Type: GrantFiled: September 12, 1996Date of Patent: May 12, 1998Assignee: The University of ReadingInventors: David Michael Hodgson, Jason Witherington
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Patent number: 5750804Abstract: A process whereby trans-3-isocamphylcyclohexanol, which is useful as a perfume ingredient, can be produced on an industrially available scale, at a low cost and at a high stereoselectivity, is disclosed. The process comprises hydrogenating 3-isocamphylcyclohexanone represented by the following formula (I): ##STR1## by using a ruthenium/phosphine complex as a catalyst in the presence of a base containing an alkali metal or an alkaline earth metal and an amine.Type: GrantFiled: March 7, 1997Date of Patent: May 12, 1998Assignee: Takasago International CorporationInventors: Makoto Emura, Takaaki Toyoda, Nobuo Seido, Makoto Harada, Ryoji Noyori, Takao Ikariya, Takashi Ohkuma
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Patent number: 5750797Abstract: Briefly, in one aspect, this invention provides an improved alkylation process for the preparation of primary and secondary hydrofluoroether compounds, said process comprising:(1) combining in a polar, aprotic solvent:a) a fluorinated carbonyl-containing compound;b) an anhydrous source of fluoride ion;c) a tertiary or aromatic amine; andd) optionally, an effective amount of a phase transfer catalyst;(2) contacting the resulting mixture with an alkylating agent; and(3) recovering hydrofluoroether from the resulting product mixture.Type: GrantFiled: April 15, 1996Date of Patent: May 12, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Daniel R. Vitcak, Richard M. Flynn
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Patent number: 5744655Abstract: A 2,3-dihalopropanol is made by reacting 2,3-dihalopropanal with a hydrogenating agent in the presence of a transition metal-containing catalyst, under conditions such that 2,3-dihalopropanol is formed. The reaction is particularly useful as Step (3) in a process to make epihalohydrin by:(1) reacting a 3-carbon hydrocarbon with an oxidizing agent to form acrolein;(2) reacting acrolein with a molecular halogen to form 2,3-dihalopropanal;(3) reducing 2,3-dihalopropanal to form 2,3-dihalopropanol; and(4) cyclizing 2,3-dihalopropanol to make epihalohydrin.The process produces epihalohydrin using only about one mole of halogen per mole of epihalohydrin. It also uses substantially less water than existing processes.Type: GrantFiled: June 19, 1996Date of Patent: April 28, 1998Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews, Paul C. Vosejpka, George J. Frycek
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Patent number: 5731478Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt or rhodium catalyst and a manganese porphyrine promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand with the cobalt or rhodium catalyst.Type: GrantFiled: October 15, 1996Date of Patent: March 24, 1998Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
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Patent number: 5728889Abstract: A process for preparing a compound of formula (I), where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-6 alkyl; R.sup.7 is halogen, cyano, NO.sub.2, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or RaS in which Ra is C.sub.1-4 alkyl; R.sup.8, R.sup.9 and R.sup.10 independently are hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, CN, NO.sub.2, phenoxy or substituted phenoxy; R.sub.b S(O)n Om in which m is 0 or 1, n is 0, 1 or 2 and Rb is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, phenyl or benzyl, NHCOR.sub.c in which c is C.sub.1-4 alkyl, NRdRe in which Rd and Re independently are hydrogen or C.sub.1-4 alkyl; RfC(O)-- in which Rf is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or C.sub.1-4 alkoxy; SO.sub.2 NRgRh in which Rg and Rh independently are hydrogen or C.sub.1-4 alkyl; or any two of R.sup.8, R.sup.9 and R.sup.Type: GrantFiled: June 24, 1997Date of Patent: March 17, 1998Assignee: Zeneca LimitedInventors: Howard Rawlinson, Jonathan William Wiffen, Stephen Martin Brown
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Patent number: 5723691Abstract: In the preparation of bisphenol-A by condensation of phenol with acetone in the presence of an acidic ion-exchange resin catalyst, pretreatment of the catalyst to render it free of acidic oligomers which are detrimental to the preparation of bisphenol-A entails washing the catalyst resin with deionized water until the washings show a specific conductance of less than 50 micromho/cm at 25.degree. C.Type: GrantFiled: August 31, 1995Date of Patent: March 3, 1998Assignee: General Electric CompanyInventors: Michael John Cipullo, Eric James Pressman