Ether Or Polyhydroxy Containing Compound Utilized Patents (Class 568/405)
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Patent number: 10844169Abstract: The invention contemplates certain polyethers, polyether derivatives, and methods of making and using those same polymers. For example, the starting materials can, e.g., citronellol, prenol, isocitronellol and isoprenol.Type: GrantFiled: January 31, 2020Date of Patent: November 24, 2020Assignee: P2 Science, Inc.Inventors: Patrick Foley, Yonghua Yang, Tania Salam
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Patent number: 9884800Abstract: Disclosed is a method of preparing 1,3-butadiene and methyl ethyl ketone from 2,3-butanediol, including: a) providing a plurality of adiabatic reactors, which include a catalyst bed for dehydrating 2,3-butanediol, without a heat transfer medium, and are connected in series; b) introducing a stream including 2,3-butanediol at a temperature ranging from 200° C. to 400° C. into a first adiabatic reactor among the plurality of adiabatic reactors; c) dehydrating the 2,3-butanediol so as to be converted into 1,3-butadiene and methyl ethyl ketone and discharging a product stream including 1,3-butadiene and methyl ethyl ketone; d) heating the discharged product stream to to 200° C. to 400° C.; and e) introducing the heated product stream into a second adiabatic reactor so that 2,3-butanediol is further dehydrated and converted into 1,3-butadiene and methyl ethyl ketone and then discharging the product stream including 1,3-butadiene and methyl ethyl ketone.Type: GrantFiled: April 3, 2017Date of Patent: February 6, 2018Assignee: SK INNOVATION CO., LTD.Inventor: Dae Sung Song
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Publication number: 20150031887Abstract: An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.Type: ApplicationFiled: February 22, 2013Publication date: January 29, 2015Inventors: Yoshiharu Iwabuchi, Masatoshi Shibuya, Ryusuke Doi
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Publication number: 20140357899Abstract: Process for preparing a halogenated precursor of an alkenone, which comprises reacting a carboxylic acid halide with a vinyl ether in a liquid reaction medium using an equipment having at least one surface in contact with the liquid reaction medium, wherein said surface consists of a material selected from glass, polytetrafluoroethylene and nickel based metal alloy.Type: ApplicationFiled: December 21, 2012Publication date: December 4, 2014Inventors: Max Josef Braun, Uta Claassen, Sara Claessens
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Patent number: 8853462Abstract: Hexafluoroacetone or a hydrate thereof is produced with a high yield by subjecting a 1-fluoro-4,4-bis(trifluoromethyl)-2,3,5-trioxolanyl ether compound represented by the general formula: wherein R is an alkyl group having 1 to 8 carbon atoms, an aryl group, or a benzyl group, which has been obtained by ozone oxidation of a heptafluoroisobutenyl ether compound, to a reduction reaction in the presence of a reducing agent selected from dialkyl sulfide containing an alkyl group having 3 or 4 carbon atoms, diaryl sulfide, diaryl disulfide, and diaralkyl sulfide.Type: GrantFiled: May 10, 2012Date of Patent: October 7, 2014Assignee: Unimatec Co., Ltd.Inventors: Yuta Ogawa, Yusuke Takahashi, Akira Endo, Sunao Ikeda
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Patent number: 8809593Abstract: The present invention relates to a process for the preparation of the hydroxyacetone or 1,2 propylene glycol. More particularly, the present invention relates to a process for preparation of hydroxyacetone or 1,2 propylene glycol by glycerol. Further, the said process is catalyzed by metal catalysts that results in 80 to 100% selectivity towards conversion of glycerol to hydroxyacetone (acetol) or 1,2 propylene glycol (1,2 PG).Type: GrantFiled: February 25, 2011Date of Patent: August 19, 2014Assignee: Council of Scientific and Industrial ResearchInventors: Chandrasshekhar Vasant Rode, Amol Mahalingappa Hengne, Ajay Ashok Ghalwadkar, Rasika Bharat Mane, Pravinkumar Hansraj Mohite, Hari Shankar Potdar
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Publication number: 20140171676Abstract: A method of preparing acrolein from glycerol or glycerine is disclosed. The method includes dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least (a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, or (b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, or (c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, or (d) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon.Type: ApplicationFiled: August 27, 2013Publication date: June 19, 2014Applicants: Centre National De La Recherche Scientifique, Adisseo France S.A.SInventors: Virginie BELLIERE-BACA, STEPHANE LORIDANT, JEAN-MARC MILLET, PASCALINE LAURIOL-GARBEY
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Patent number: 8735633Abstract: A method comprising reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), without using fermentation or direct oxidation of the glycerol is provided. DHA is useful in various products, including as a sunless tanning agent.Type: GrantFiled: July 14, 2011Date of Patent: May 27, 2014Assignee: Board of Trustees of Michigan State UniversityInventors: Dennis Miller, Xi Hong, Carl Lira, Omar McGiveron
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Patent number: 8664449Abstract: The invention relates to a method for continuously producing 2-butanone from 2,3-butanediol in hot pressurized water having an added electrolyte, characterized in that a compound selected from among the group comprising Ce(SO4)2, Fe2(SO4)3, Al2(SO4) is used as the added electrolyte.Type: GrantFiled: October 17, 2011Date of Patent: March 4, 2014Assignee: Wacker Chemie AGInventors: Christoph Ruedinger, Hans-Juergen Eberle, Andrea Soler, Herbert Vogel
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Patent number: 8563780Abstract: Allyl and propargyl ethers of the formula X—C(R1)(R2)—O—C(CH3)(R3)—OCH3 (I), wherein X is an ethynyl or vinyl group, R1 is methyl or ethyl, R2 is a saturated or unsaturated linear or cyclic aliphatic hydrocarbon residue and R3 is methyl or ethyl, a method for their preparation and their use in the manufacture of ?-ketoallenes, ?,?-unsaturated carbonyl compounds and ?,?-unsaturated ketones.Type: GrantFiled: May 12, 2009Date of Patent: October 22, 2013Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Rolf Kuenzi
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Publication number: 20130197273Abstract: The invention relates to a method for continuously producing 2-butanone from 2,3-butanediol in hot pressurized water having an added electrolyte, characterized in that a compound selected from among the group comprising Ce(SO4)2, Fe2(SO4)3, Al2(SO4) is used as the added electrolyte.Type: ApplicationFiled: October 17, 2011Publication date: August 1, 2013Applicant: WACKER CHEMIE AGInventors: Christoph Ruedinger, Hans-Juergen Eberle, Andrea Soler, Herbert Vogel
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Publication number: 20130096322Abstract: A method of production of value-added, biobased chemicals, derivative products, and/or purified glycerin from bioglycerin of recycled oil, grease, and/or fat origin is described herein. A method of purification of bioglycerin of recycled oil, grease, and/or fat origin is also described herein. The method of purification of bioglycerin of recycled oil, grease, and/or fat origin described provides methods for desalinating, decolorizing, and/or concentrating bioglycerin of recycled oil, grease, and/or fat origin for the production of biobased chemicals, derivative products, and/or purified glycerin.Type: ApplicationFiled: January 12, 2012Publication date: April 18, 2013Applicant: THESIS CHEMISTRY, LLCInventors: John R. Peterson, Christopher M. Yost
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Publication number: 20130079561Abstract: The present invention relates to a process for the preparation of the hydroxyacetone or 1,2 propylene glycol. More particularly, the present invention relates to a process for preparation of hydroxyacetone or 1,2 propylene glycol by glycerol. Further, the said process is catalyzed by metal catalysts that results in 80 to 100% selectivity towards conversion of glycerol to hydroxyacetone (acetol) or 1,2 propylene glycol (1,2 PG).Type: ApplicationFiled: February 25, 2011Publication date: March 28, 2013Inventors: Chandrasshekhar Vasant Rode, Arnol Mahalingappa Hengne, Ajay Ashok Ghalwadkar, Rasika Bharat Mane, Pravinkumar Hansraj Mohite, Hari Shankar Potdar
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Publication number: 20120283478Abstract: Disclosed are methods for generating propylene glycol, ethylene glycol and other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols from biomass using hydrogen produced from the biomass. The methods involve reacting a portion of an aqueous stream of a biomass feedstock solution over a catalyst under aqueous phase reforming conditions to produce hydrogen, and then reacting the hydrogen and the aqueous feedstock solution over a catalyst to produce propylene glycol, ethylene glycol and the other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols. The disclosed methods can be run at lower temperatures and pressures, and allows for the production of oxygenated hydrocarbons without the need for hydrogen from an external source.Type: ApplicationFiled: June 8, 2012Publication date: November 8, 2012Applicant: VIRENT, INC.Inventor: Randy D. Cortright
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Publication number: 20120101305Abstract: A process for preparing a halogenated precursor of an alkenone, which comprises reacting a carboxylic acid halide with a vinyl ether in a liquid reaction medium under turbulent conditions and a process for preparing an alkenone, by eliminating hydrogen halide from said precursor to form the alkenone.Type: ApplicationFiled: July 5, 2010Publication date: April 26, 2012Applicant: SOLVAY SAInventors: Max Braun, Stefan Palsherm, Uta Claasen
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Publication number: 20120029240Abstract: Allyl and propargyl ethers of the formula X—C(R1)(R2)—O—C(CH3)(R3)—OCH3 (I), wherein X is an ethynyl or vinyl group, R1 is methyl or ethyl, R2 is a saturated or unsaturated linear or cyclic aliphatic hydrocarbon residue and R3 is methyl or ethyl, a method for their preparation and their use in the manufacture of ?-ketoallenes, ?,?-unsaturated carbonyl compounds and ?,?-unsaturated ketones.Type: ApplicationFiled: May 12, 2009Publication date: February 2, 2012Inventors: Werner Bonrath, Rolf Kuenzi
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Publication number: 20120014889Abstract: A method comprising reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), without using fermentation or direct oxidation of the glycerol is provided. DHA is useful in various products, including as a sunless tanning agent.Type: ApplicationFiled: July 14, 2011Publication date: January 19, 2012Inventors: Dennis Miller, Xi Hong, Carl Lira, Omar McGiveron
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Publication number: 20110124690Abstract: The present invention relates to compositions comprising an effective amount of a Panaxytriol Compound and a tubulin-binding drug, methods for treating or preventing cancer or a neurotrophic disorder comprising administering to a subject in need thereof an effective amount of a Panaxytriol Compound and a tubulin-binding drug, and methods for making a Panaxytriol Compound.Type: ApplicationFiled: February 22, 2008Publication date: May 26, 2011Inventors: Samuel J. Danishefsky, Heedong Yun, Ting-Chao Chou, Xiaoguang Lei, Dalibor Sames
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Patent number: 7652171Abstract: The present invention relates to a process for the cleavage of dialkoxyalkanes to give corresponding aldehydes or ketones, where the cleavage is carried out in the presence of at least one ionic liquid of the general formula K+A?.Type: GrantFiled: January 25, 2007Date of Patent: January 26, 2010Assignee: Merck Patent GmbHInventors: Nikolai (Mykola) Ignatyev, Karsten Koppe, Hermann Josef Frohn, Peter Barthen
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Publication number: 20090012329Abstract: The present invention relates to a process for the cleavage of dialkoxyalkanes to give corresponding aldehydes or ketones, where the cleavage is carried out in the presence of at least one ionic liquid of the general formula K+A?.Type: ApplicationFiled: January 25, 2007Publication date: January 8, 2009Inventors: Nikolai (Mykola) Ignatyev, Karsten Koppe, Hermann Josef Frohn, Peter Barthen
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Publication number: 20080315151Abstract: A reactive-separation process converts glycerin into lower alcohols, having boiling points less than 200° C., at high yields. Conversion of natural glycerin to propylene glycol through an acetol intermediate is achieved at temperatures from 150° to 250° C. at pressures from 1 and 25 bar. The preferred applications of the propylene glycol are as an antifreeze, deicing compound, or anti-icing compound. The preferred catalyst for this process in a copper-chromium.Type: ApplicationFiled: August 28, 2006Publication date: December 25, 2008Inventors: Galen J. Suppes, William Rusty Sutterlin
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Patent number: 7087794Abstract: The present invention provides a process for treating a stream, say, an olefins stream, e.g., propylene, containing at least one ether, e.g., dimethyl ether, and/or at least one of an alkyne and an alkadiene, e.g., methyl acetylene and propadiene, typically present as impurities. The process comprises: contacting the stream with a metal-containing catalyst, e.g., palladium supported on alumina, under conditions sufficient to convert the ether and the at least one of an alkyne and an alkadiene to provide a product stream having a reduced impurities content.Type: GrantFiled: November 15, 2002Date of Patent: August 8, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Michael A. Risch, John Di-Yi Ou
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Patent number: 7057079Abstract: A method of producing a halogen alkenone ether by attaching carboxylic acid halogenides or carboxylic acid anhydrides to a vinyl ether. According to the invention the method is carried out in the presence of an onium salt of a carbonic acid which can be regenerated. The resulting product is obtained in high yields. Alternatively, pyridine which is substituted by one, two or three C1–C3 alkyl groups or other onium salts can be used.Type: GrantFiled: August 6, 2004Date of Patent: June 6, 2006Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Uta Claassen
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Patent number: 6867307Abstract: Intermediate compounds which can be used in the preparation of phytone and Vitamin E, a process for the preparation thereof, and a process for the preparation of phytone and Vitamin E from these intermediate compounds.Type: GrantFiled: July 12, 2001Date of Patent: March 15, 2005Assignee: Adisseo France S.A.S.Inventors: Jean-Erick Ancel, Pierre Meilland
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Patent number: 6586635Abstract: A process for the preparation of &bgr;,&ggr;,&dgr;-unsaturated ketones and/or &agr;,&bgr;,&ggr;,&dgr;-unsaturated ketones by the reaction of an unsaturated alcohol with an enol ether or mixture of enol ethers, with formation of ketals as a by-product, at temperatures of from 50° C. to 200° C., in the presence of an acid catalyst, whereby one or all of the reagents is/are heated to the reaction temperature of from 50° C. to 200° C. before the acid catalyst is added.Type: GrantFiled: April 26, 2002Date of Patent: July 1, 2003Assignee: Degussa AGInventors: Nongyuan Shi, Bernd Drapal, Steffen Krill, Markus Julino, Klaus Huthmacher
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Patent number: 6441243Abstract: The invention relates to a process for the selective oxidation of alcohols to ketones or to aldehydes by means of an alkali hypohalite under alkaline conditions, which comprises carrying out the oxidation in the presence of a heterogeneous oxidation catalyst that is insoluble in the reaction medium and is selected from the group comprising the compounds of formula (I) (III), wherein n is a number from 3 to 3000; or a 4-oxy-2,2,6,6-tetramethylpiperidin-1-oxyl that is 4-oxy-bound to a Merrifield polymer. The invention relates also to the compounds of formulae (II) and (III) and to the use of the above-mentioned oxidation catalysts for the oxidation of alcohols.Type: GrantFiled: November 15, 2000Date of Patent: August 27, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Reinhard Sommerlade, Hansjörg Grützmacher, Souâd Boulmaâz
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Patent number: 6380437Abstract: Process for the preparation of unsaturated 4,5-allene ketones by reaction of tertiary propargyl alcohols with alkenyl alkyl ethers or ketals in the presence of aliphatic sulfonic acids or sulfonic acid salts.Type: GrantFiled: October 11, 2000Date of Patent: April 30, 2002Assignee: Degussa AGInventors: Nongyuan Shi, Frank Hübner, Bernd Drapal, Rainer Peter, Steffen Krill, Klaus Huthmacher, Christoph Weckenbecker
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Patent number: 6376718Abstract: A catalytic dehydrogenation of alkylene glycol ether to ether ketone or aldehyde is disclosed. The dehydrogenation is performed with copper chromite catalyst and at least 5 wt % of water based on alkylene glycol ether. It has been found that the selectivity to formation of ether ketone or aldehyde increases with increasing the amount of water in the alkylene glycol ether.Type: GrantFiled: November 17, 2000Date of Patent: April 23, 2002Assignee: Arco Chemical Technology, L.P.Inventor: Prakash Balan
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Patent number: 6191308Abstract: &agr;-Hydroxycarbonyl compounds are obtained from aldehydes or ketones by forming an acetal or ketal which is decomposed to a vinyl ether. The ether is selectively oxidized under conditions yielding an &agr;-hydroxy-aldehyde or &agr;-hydroxy-ketone with the carbonyl group protected. The last-mentioned compounds are valuable sources for other functional organic molecules, for example lactic acid.Type: GrantFiled: August 17, 1999Date of Patent: February 20, 2001Assignee: Exxon Chemical Patents Inc.Inventors: Jihad Mohammed Dakka, Georges Marie Karel Mathys, Hans Karel Theresia Goris
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Patent number: 6184420Abstract: Unsaturated ketones of the formulae Ia and Ib are prepared by a process consisting of the combination of the following reactions: a) The conventional reaction of an allyl alcohol of the formula IIa or a propargyl alcohol of the formula IIb with an isopropenyl ether of the formula III with formation of a ketal of the formula IV as a byproduct, b) preparation of the isopropenyl ether of the formula III by reacting a ketal of the formula IV with propyne or allene, or a mixture thereof in the gas phase at elevated temperatures in the presence of a heterogeneous catalyst containing zinc or cadmium together with silicon or oxygen, and c) feeding the ketal of the formula IV formed in the reaction (a) into stage (b) for the preparation of the isopropenyl ether of the formula III again.Type: GrantFiled: September 10, 1998Date of Patent: February 6, 2001Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Stefan Kaeshammer, Heinz Etzrodt, Wulf Kaiser
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Patent number: 5580996Abstract: The compounds of the invention are characterised by the formulae ##STR1## wherein index p represents an integer equal to 2 or 3 and q can take the value zero or 1, with the provision that p+q=3. Said compounds are obtained from hex-3-yne-2,5-diol following a process which comprises reacting an ethylenic compound of formula(CH.sub.3).sub.2 C.dbd.C(H).sub.n (CH.sub.3).sub.m (I)wherein index n represents an integer equal to 1 or 2 and m can take the values zero or 1 and wherein n+m=2, with hex-3-yne-2,5-diol, followed by the oxidation of the acetylenic ether obtained by means of ruthenium tetroxide. The compounds of formula (III) can be used as intermediate products for the preparation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol.RTM.).Type: GrantFiled: April 13, 1995Date of Patent: December 3, 1996Assignee: Firmenich SAInventors: Hubert Mimoun, Alexander Zaslona, Jean-Paul Leresche
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Patent number: 5426206Abstract: Methods are provided for preparing all four diastereomers of 2-alkyl-3-hydroxyalkanals, 2-alkyl-3-silyloxyalkanals, and the like, with high enantiocontrol, using non-aldol chemistry. The synthetic methods also provide novel, stereospecific routes to polypropinates and chiral 2-substituted-1,3 diols.Type: GrantFiled: November 24, 1993Date of Patent: June 20, 1995Assignee: The Regents of the University of CaliforniaInventors: Michael E. Jung, Derin C. D'Amico
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Patent number: 5380755Abstract: The present invention provides alkyl and alkylbenzyl ethers of substituted hydroquinones and pharmaceutical compositions containing them. The present invention further provides methods of using these compounds and compositions to inhibit monoamine oxidase, particularly monoamine oxidase B. The present invention further provides methods for the treatment of diseases involving monoamine oxidase.Type: GrantFiled: July 24, 1992Date of Patent: January 10, 1995Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Argyrios G. Arvanitis, Everett L. Scholfield
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Patent number: 5367032Abstract: Epoxides are converted selectively to the corresponding carbonyl-containing compounds by reacting the epoxide with an oxidizing agent, typically hydrogen peroxide, in a liquid aqueous/organic two-phase system comprising:(a) an organic phase substantially containing the epoxide, and(b) an aqueous acidic phase substantially containing the oxidizing agent, in the presence of an onium compound capable of achieving phase partitioning and a catalytic system comprising a first catalyst component which is at least one element selected from tungsten, molybdenum, vanadium and chromium, or a compound containing at least one of the aforesaid elements, and a second catalyst component which is a phosphorus (V) acid or a species convertible to a phosphorus (V) acid.Type: GrantFiled: January 11, 1994Date of Patent: November 22, 1994Assignee: BP Chemicals LimitedInventors: David A. Hancock, David J. Moreton, Lee J. Morton
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Patent number: 5206442Abstract: The preparation of .alpha.,.beta.-unsaturated aldehydes and ketones IO.dbd.C(R.sup.1)--CR.sup.2 .dbd.CR.sup.3 R.sup.4 Iis carried out by acid hydrolysis of cyclic .alpha.,.beta.-unsaturated acetals II ##STR1## in the presence of saturated aldehydes.Type: GrantFiled: February 14, 1992Date of Patent: April 27, 1993Assignee: BASF AktiengesellschaftInventors: Christiane Mackenroth, Ernst Buschmann
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Patent number: 5120879Abstract: Polyoxypropylene diketones are prepared by initially adding predetermined amounts of a mono- or dicarboxylic acid having a pK<4.5 and a water solubility at 25.degree. C. of >1%, a polyoxypropylene glycol and, optionally, water, to a reaction zone and thereafter adding an aqueous solution of an alkali metal or an alkaline earth metal hypochlorite oxidant to the reaction zone with agitation under reaction conditions including a temperature of about 10.degree. to about 50.degree. C., a pressure of about 0 to 1,000 psig. and a total reaction time of about 0.5 to 20 hours, whereby said polyoxypropylene glycol will be substantially selectively converted to the said corresponding diketone, and recovering said diketone.Type: GrantFiled: May 30, 1991Date of Patent: June 9, 1992Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 5099073Abstract: A process for the conversion of a polyoxypropylene glycol to the corresponding diketone derivative by dehydrogenation in the presence of an unsupported nickel, copper, chromia catalyst or a Raney nickel catalyst.Type: GrantFiled: February 11, 1991Date of Patent: March 24, 1992Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, John M. Larkin
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Patent number: 4980514Abstract: Diketones useful as intermediates for reaction with carboxylic acids to provide surfactants and for reaction with amine adducts to provide fuel additives are prepared from polyoxyalkylene glycols having a molecular weight of about 200 to about 2,000 and having the formula: ##STR1## wherein R is hydrogen or methyl and wherein n is a positive number having a value of 1 to about 50,The polyoxyalkylene polyol is oxidized in the presence of a halogenated alkane solvent and a ruthenium catalyst with an alkali metal or alkaline earth metal hypochlorite at a temperature of about 10.degree. to about 50.degree. C. and a pressure of about 0 to 1,000 psig. over a period of about 10 to about 20 hours to provide the corresponding diketone having the formula: ##STR2## wherein R and n have the meaning given above.Type: GrantFiled: December 1, 1989Date of Patent: December 25, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4978785Abstract: Carboxylic acid derivatives and methyl ketone derivatives of polyoxypropylene glycols are prepared by the selective nitric acid oxidation of a polyoxypropylene glycol in the presence of an alkali metal nitrite. If the alkali metal nitrite is added to an aqueous solution of nitric acid and the polyoxypropylene glycol is thereafter added, carboxylic acid derivatives of the polyoxypropylene glycol are provided. If a mixture of an alkali metal nitrite and a polyoxypropylene glycol is added to an aqueous solution of nitric acid, a reaction product containing a predominant amount of methyl ketone derivatives of the polyoxypropylene glycol is provided.Type: GrantFiled: December 11, 1989Date of Patent: December 18, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, John M. Larkin
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Patent number: 4960948Abstract: Polyoxypropylene diketones are prepared by initially adding predetermined amounts of glacial acetic acid, a polyoxypropylene glycol and, optionally, water, to a reaction zone and thereafter adding an aqueous solution of an alkali metal or an alkaline earth metal hypochlorite oxidant to the reaction zone with agitation under reaction conditions including a temperature of about 10.degree. to about 50.degree. C., a pressure of about 0 to 1,000 psig. and a total reaction time of about 0.5 to 20 hours, whereby said polyoxypropylene glycol will be substantially selectively converted to the said corresponding diketone, and recovering said diketone.Type: GrantFiled: December 26, 1989Date of Patent: October 2, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4868337Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.Type: GrantFiled: December 17, 1987Date of Patent: September 19, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4788325Abstract: A process for making a carbonyl-containing compound is disclosed. In this process an allylic ether is contacted with water in the presence of a cobalt-containing material under an atmosphere of carbon monoxide gas.Type: GrantFiled: May 29, 1987Date of Patent: November 29, 1988Assignee: National Distillers and Chemical CorporationInventor: Biau-Hung Chang
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Patent number: 4642386Abstract: A process for preparing pure fluoral hydrate or hexafluoroacetone hydrate which comprises reacting a hemiacetal with the formula ##STR1## wherein R is hydrogen or CF.sub.3, with water in a distillation column, removing respectively the methanol or ethanol produced at the head of the column, and recovering at the bottom of the column the pure hydrate so produced.Type: GrantFiled: July 16, 1985Date of Patent: February 10, 1987Assignee: AtochemInventors: Bernard Cheminal, Henri Mathais, Marc Thomarat
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Patent number: 4616095Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloakyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: October 7, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4613706Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: September 23, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4460793Abstract: A process for the production of a monochloromethyl ketone of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 each independently is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkinyl or aryl radical, orR.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted carbocyclic ring,comprising reacting a 1,1-dichloroalkene of the formula ##STR2## with a phenolate of the formula ##STR3## in which R.sup.4 each independently is a halogen atom, a nitro group, or an optionally substituted alkyl, alkoxy or aryl radical,n is 0, 1, 2 or 3, andM is one equivalent of an alkali metal ion or alkaline earth metal ion,thereby to obtain a phenyl ether intermediate, and then subjecting the phenyl ether intermediate to an acid hydrolysis. The products are useful as intermediates in the synthesis of fungicides.Type: GrantFiled: December 11, 1981Date of Patent: July 17, 1984Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4357282Abstract: Fluorinated carbonyl compounds are prepared by contacting a fluorinated methyl or ethyl ether containing at least one methoxylated carbon atom-containing group selected from: --CF.sub.2 OR.sup.3, .dbd.CFOR.sup.3, ##STR1## wherein R.sup.3 is CH.sub.3 or C.sub.2 H.sub.5, with a catalyst selected from:SbX.sub.5, TaX.sub.5, NbX.sub.5, AsX.sub.5, BiX.sub.5, TiX.sub.4, ZrX.sub.4, HfX.sub.4, FeX.sub.3,mixtures of SbX.sub.3 and SbX.sub.5, ZM'X'.sub.6, and mixtures of ZM'X'.sub.6 and M'X.sub.5 where X, independently, is F, Cl, Br or I, X' is F or Cl; and Z is H, NO, O.sub.2, alkali metal or NY.sub.4 where Y, independently, is H or alkyl of 1 to 6 carbon atoms, and M' is Sb or As at a temperature of -20.degree. to 200.degree. C.Type: GrantFiled: April 3, 1981Date of Patent: November 2, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: Daniel G. Anderson, David C. England, Alwin S. Milian, Jr.
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Patent number: 4224252Abstract: Disclosed are improved procedures for preparing pinacolone from compounds of general formula (I) ##STR1## wherein, either adjacent two of A, B, C and D form a single bond between them and the remaining two are hydrogen atoms, or both A and D are hydrogen atoms and one of B and C is a hydrogen atom and the other represents OH, Cl, Br, HSO.sub.4, H.sub.2 PO.sub.4 or ClO.sub.4, anda new procedure which enables preparing pinacolone from a compound of general formula (II) ##STR2## wherein, both W and Y are each hydrogen atoms and X and Z are the same or different and each represents OH, Cl, Br, HSO.sub.4, H.sub.2 PO.sub.4, ClO.sub.4 or RCOO wherein R is a hydrogen atom or an alkyl group of 1 to 3 carbon atoms, or one of W and Y is a hydrogen atom and the other forms a single bond together with X, and Z represents OH, Cl, Br, HSO.sub.4 H.sub.2 PO.sub.4, ClO.sub.4 or RCOO where R is defined as above.Type: GrantFiled: May 15, 1979Date of Patent: September 23, 1980Assignee: Kuraray Co., Ltd.Inventors: Sunao Kyo, Haruo Tsuchiya, Hidetsugu Tanaka