Boron Containing Catalyst Utilized Patents (Class 549/530)
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Patent number: 9533932Abstract: Cyclododecanone (CDON) is prepared by epoxidizing cyclododecene (CDEN) to epoxycyclododecane (CDAN epoxide), and rearranging the CDAN epoxide to CDON to obtain a mixture comprising said CDON and cyclododecane (CDAN), wherein CDAN is separated from the CDON-containing mixture and oxidized to CDON.Type: GrantFiled: July 31, 2015Date of Patent: January 3, 2017Assignee: EVONIK DEGUSSA GmbHInventors: Kevin Micoine, Ralf Meier, Juergen Herwig, Martin Roos, Harald Haeger, Luca Cameretti, Jens Doering
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Publication number: 20110295019Abstract: The present invention relates to a method for producing 1-hydroxymethyl-1,2-diphenyloxiranes from 2,3-diphenylpropenals by means of epoxidation and reduction. The formation of objectionable by-products can be suppressed in that the reduction is started before the 2,3-5 diphenylpropenal is completely converted. The hydroxymethyl diphenyloxiranes represent valuable intermediate products for producing 1-azolylmethyl-1,2-diphenyloxiranes, wherein the latter can be easily produced from said intermediate products by introducing the azolyl group.Type: ApplicationFiled: February 4, 2010Publication date: December 1, 2011Applicant: BASF SEInventors: Rainer Noack, Clemens Palm, Carsten Gröning, Gunter Lipowsky
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Patent number: 7544763Abstract: The present invention relates to a manufacturing process for producing a polyol from a fatty acid ester in-situ. The process does not use any added organic or inorganic acid catalyst. The polyol produced by the process is essentially free of any cation or anion. The fatty acid ester oil epoxidation and hydroxylation reactions can occur progressively in the same reactor for essentially a one-pot reaction. The polyol produced by the process is essentially free of any cation or anion. The polyol can be used to produce polyurethanes having improved properties.Type: GrantFiled: November 7, 2006Date of Patent: June 9, 2009Assignee: Arkema Inc.Inventor: Mohammad Kazemizadeh
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Patent number: 7038090Abstract: A process and catalyst for preparing organic hydroperoxides by oxidizing hydrocarbon compounds in the presence of an oxygen-containing gas and a catalyst containing a transition metal on a solid support.Type: GrantFiled: April 1, 2004Date of Patent: May 2, 2006Assignee: UOP LLCInventors: Timothy A. Brandvold, Gregory J. Lewis, Lisa M. King, Lawrence E. Brewer
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Patent number: 6974888Abstract: Process for preparing alkylaryl hydroperoxide containing product, which process comprises: (a) oxidation of an alkylaryl compound to obtain reaction product containing alkylaryl hydroperoxide, (b) contacting with water at least part of the alkylaryl hydroperoxide containing reaction product obtained in step (a) which reaction product contains less than 0.05 % wt of sodium, (c) separating the product of step (b) into a hydrocarbonaceous phase containing alkylaryl hydroperoxide and an aqueous phase, (d) optionally repeating process steps (b) and (c) one or more times, (e) contacting at least part of the hydrocarbonaceous phase containing alkylaryl hydroperoxide obtained in step (c) or (d) with olefin and catalyst to obtain alkylaryl hydroxide and oxirane compound, and (f) separating at least part of the oxirane compound from the alkylaryl hydroxide.Type: GrantFiled: January 14, 2004Date of Patent: December 13, 2005Assignee: Shell Oil CompanyInventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
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Patent number: 6764545Abstract: The present invention provides a production method including adding water to a solution of (2R,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2R,3S)-epoxide compound) or (2S,3R)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2S,3R)-epoxide compound) in a polar solvent to allow crystallization, whereby to produce crystals of the (2R,3S)-epoxide compound or the (2S,3R)-epoxide compound conveniently in a high yield by an industrial production method without requiring an extremely low temperature.Type: GrantFiled: December 11, 2001Date of Patent: July 20, 2004Assignee: Ajinomoto Co., Inc.Inventors: Yuichi Suzuki, Naoko Hirose, Tomoyuki Onishi, Kunisuke Izawa
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Patent number: 6700005Abstract: Process for preparing alkylaryl hydroperoxide containing product, which process comprises: (a) oxidation of an alkylaryl compound to obtain reaction product containing alkylaryl hydroperoxide, (b) contacting with water at least part of the alkylaryl hydroperoxide containing reaction product obtained in step (a) which reaction product contains less than 0.05% wt of sodium, (c) separating the product of step (b) into a hydrocarbonaceous phase containing alkylaryl hydroperoxide and an aqueous phase, (d) optionally repeating process steps (b) and (c) one or more times, (e) contacting at least part of the hydrocarbonaceous phase containing alkylaryl hydroperoxide obtained in step (c) or (d) with olefin and catalyst to obtain alkylaryl hydroxide and oxirane compound, and (f) separating at least part of the oxirane compound from the alkylaryl hydroxide.Type: GrantFiled: February 6, 2003Date of Patent: March 2, 2004Assignee: Shell Oil CompanyInventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
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Patent number: 6673950Abstract: In a process for reacting an organic compound with a hydroperoxide using at least one heterogeneous catalyst, both the pH and the temperate of the reaction medium are changed during the reactionType: GrantFiled: February 1, 2002Date of Patent: January 6, 2004Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Alwin Rehfinger, Peter Bassler, Norbert Rieber, Anne Wenzel, Andreas Walch, Wolfgang Harder
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Patent number: 6620951Abstract: A process for producing an oxirane compound from an organic peroxide other than ethylbenzene hydroperoxide and an olefin in the presence of an immobilized catalyst bed, wherein the process satisfies the following conditions (1) to (4): (1) the catalyst bed is divided into n catalyst beds and the catalyst beds are used in series, wherein n is an integer of 2 or more, (2) a fresh organic peroxide is divided into portions, which are supplied to respective inlets of the catalyst beds, (3) a fresh olefin is supplied to the inlet of the first catalyst bed, and (4) the reaction mixture discharged from each outlet of respective catalyst beds excluding the final catalyst bed is supplied to the inlet of the subsequent catalyst bed.Type: GrantFiled: September 12, 2002Date of Patent: September 16, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Noriaki Oku, Masaaki Katao
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Patent number: 6512129Abstract: Insoluble resinous sodium materials are separated from a hydroperoxide/olefin epoxidation feed by contact with a fine screen or a bed of coalescing solids.Type: GrantFiled: January 23, 2002Date of Patent: January 28, 2003Assignee: Arco Chemical Technology, L.P.Inventors: Xiangmin Li, David W. Leyshon
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Patent number: 6228955Abstract: A process for preparing an optically-enriched chiral epoxide of formula I wherein R1, R2 and R3 are each independently selected from H, R, R—CO— and R—O—CO—, each R independently being substantially a hydrocarbon group of up to 20 carbon atoms, and X is an alkyl or cycloalkyl group of up to 10 carbon atoms, provided that —CO—X is not enolisable, which comprises the asymmetric epoxidation of a corresponding prochiral alkene of formula II R1R2C═CR3—CO—X (II) by reaction with an oxidant in the presence of a chiral catalyst. Many optically-enriched epoxides (I) are novel.Type: GrantFiled: October 20, 1997Date of Patent: May 8, 2001Assignee: Chirotech Technology, Ltd.Inventors: Stanley Michael Roberts, Brian Michael Adger
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Patent number: 6124483Abstract: Process of making compounds of the formula ##STR1## wherein R.sub.1 =(C.sub.1 -C.sub.6) alkyl;X=O, S, NH;R.sub.2 =divalent saturated organic group;Y=O, S, NH, ester;R.sub.3 =cyclic moiety containing oxirane group;comprising reacting a compound of the formula ##STR2## wherein R.sub.4 is a cyclic moiety containing C.dbd.C group with hydrogen peroxide in the presence of (a) tungstic acid, (b) phosphoric acid or its metal salts, and (c) at least one phase transfer catalyst;polymers of compounds of formula I; andcompounds of formula I except for compounds wherein R.sub.4 is a dicyclopentenyl epoxide, Y is O, R.sub.2 is --CH.sub.2 CH.sub.2 --, X is O, and R.sub.1 is H or methyl.Type: GrantFiled: December 23, 1996Date of Patent: September 26, 2000Assignee: Sartomer Technology CompanyInventors: Mingxin Fan, Gary W. Ceska, James Horgan
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Patent number: 6107433Abstract: 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: GrantFiled: November 6, 1998Date of Patent: August 22, 2000Assignee: Pittsburg State UniversityInventors: Zoran Petrovic, Andrew Guo, Ivan Javni
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Patent number: 6063943Abstract: 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: GrantFiled: December 11, 1998Date of Patent: May 16, 2000Assignee: Korea Advanced Institute of Science and TechnologyInventors: Son Ki Ihm, Chang Gun Oh, Jou Hyeon Ahn, Jong Chan Kim, David C. Sherrington
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Patent number: 5166371Abstract: Prochiral ethylenically unsaturated substrates are converted to chiral epoxides by reaction with optically active hydroperoxides in the presence of transition metal catalysts. For example, chiral glycidol is obtained by asymmetric epoxidation of allyl alcohol using optically active ethyl benzene hydroperoxide and a titaniuym alkoxide/tartrate catalyst. The chiral epoxide products are versatile synthetic intermediates.Type: GrantFiled: August 9, 1991Date of Patent: November 24, 1992Assignee: Arco Chemical Technology, L.P.Inventors: Wilfred P. Shum, Haven S. Kesling, Jr., John G. Zajacek
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Patent number: 4814511Abstract: Cyclohexyl hydroperoxide containing reaction mixtures obtained by oxidation of cyclohexane with molecular oxygen or molecular oxygen containing gases in the liquid phase at from 130.degree. to 200.degree. C. and under from 5 to 125 bar are worked up by reaction with cycloolefins at elevated temperature in the presence of catalysts to react cyclohexyl hydroperoxide with cyclohexene at elevated temperatures in the presence of cyclohexene-soluble compounds of transition metals of groups 4 or 5 or 6 of the periodic table or of one or more cyclohexane-insoluble compounds of a transition metal of group 4 or 5 or 6, or in the presence of selenium, tellurium or a boride, and the resulting cyclohexene oxide at elevated temperatures to cyclohexanol in the presence of hydrogenation catalysts.Type: GrantFiled: October 23, 1987Date of Patent: March 21, 1989Assignee: BASF AktiengesellschaftInventors: Gerald Neubauer, Rolf Schnabel, Juergen Hartig, Josef Ritz
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Patent number: 4755613Abstract: The invention relates to a process for preparing aromatic or hetero-aromatic aldehydes by the Reimer-Tiemann formylation reaction. The process comprises employing a solid alkaline hydroxide in order to carry out the reaction in a solid/liquid medium and by adjusting the initial hydration rate of the medium to be higher than 0.05 moles of water per mole of initial compound and less than 1.5 moles of water per mole of alkaline hydroxide initially in the medium. Such a process makes it possible to substantially increase the yield of the Reimer-Tiemann reaction and to avoid tar formation entirely or in large part.Type: GrantFiled: April 10, 1987Date of Patent: July 5, 1988Assignee: Institut National PolytechniqueInventors: Annick Thoer, Ghislain Denis, Michel Delmas, Antoine Gaset