O-containing Patents (Class 585/606)
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Patent number: 11976017Abstract: The present invention relates to processes for preparing isoprene and mono-olefins comprising at least six carbon atoms.Type: GrantFiled: November 11, 2020Date of Patent: May 7, 2024Assignee: Dow Technology Investments LLCInventors: Marinus A. Bigi, Michael A. Brammer, Glenn A. Miller, Amarnath Singh
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Patent number: 11446635Abstract: The present invention relates to a catalyst which is a composite oxide including at least one element X selected from the group consisting of elements belonging to Groups 3 to 6 of the periodic table, and at least one element Z selected from the group consisting of elements belonging to Group 14 of the periodic table, wherein the catalyst has mesopores.Type: GrantFiled: December 27, 2018Date of Patent: September 20, 2022Assignee: SEKISUI CHEMICAL CO., LTD.Inventors: Haruka Nishiyama, Noritoshi Yagihashi, Toshihito Miyama
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Patent number: 10196326Abstract: Process for the production of a diene, preferably a conjugated diene, more preferably 1,3-butadiene, comprising the dehydration of at least one alkenol in the presence of at least one catalytic material comprising at least one acid catalyst based on silica (SiO2) and alumina (AI2O3), preferably a silica-alumina (SiO2-AI2O3), said catalyst having a content of alumina (AI2O3) lower than or equal to 12% by weight, preferably ranging from 0.1% by weight to 10% by weight, with respect to the total weight of the catalyst. Preferably, said alkenol can be obtained directly from biosynthesis processes, or through the catalytic dehydration of at least one diol, preferably a butanediol, more preferably 1,3-butanediol, even more preferably bio-1,3-butanediol, deriving from biosynthesis processes. Preferably, said 1,3-butadiene is bio-1,3-butadiene.Type: GrantFiled: February 22, 2016Date of Patent: February 5, 2019Assignee: versalis S.p.A.Inventors: Stefano Ramello, Vittorio Milanesi, Roberto Buzzoni
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Publication number: 20150105598Abstract: An object of the present invention is to provide a process for producing an octadiene from 2,7-octadienyl formate in an industrially useful manner in which palladium can maintain its catalytic activity for a long period of time. More specifically, the present invention relates to a process for producing an octadiene which includes the steps of continuously adding 2,7-octadienyl formate into a reaction system in which a mixture of a palladium compound, a tertiary organophosphorus compound and a solvent is present; and subjecting the 2,7-octadienyl formate to reaction while continuously distilling off a reaction product containing the resulting octadiene out of the reaction system.Type: ApplicationFiled: May 15, 2013Publication date: April 16, 2015Applicant: KURARAY CO., LTD.Inventors: Osamu Nakayama, Junichi Fuji, Masaki Shimizu
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Patent number: 8933285Abstract: Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with a low-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product. The methods further comprise hydrogenating the metathesized product under conditions sufficient to form a jet fuel composition.Type: GrantFiled: November 25, 2009Date of Patent: January 13, 2015Assignee: Elevance Renewable Sciences, Inc.Inventors: Melvin L. Luetkens, Jr., Steven A. Cohen, Chander Balakrishnan
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Publication number: 20140024872Abstract: The present disclosure relates to bioengineering approaches for producing biofuel and, in particular, to the use of a C1 metabolizing microorganism reactor system for converting C1 substrates, such as methane or methanol, into biomass and subsequently into biofuels, bioplastics, or the like.Type: ApplicationFiled: July 12, 2013Publication date: January 23, 2014Inventors: Joshua Silverman, Sol M. Resnick, Michael Mendez
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Publication number: 20130072696Abstract: A ternary V—Ti—P mixed oxide is shown to catalytically dehydrate 2-methyl-tetrahydrofuran in high conversion to give piperylene, in good yield. Volatile products collected from this reaction contain piperylene in concentrations as high as 80 percent by weight. Dehydration of glycerol to acrolein in high conversion and moderate selectivity is also demonstrated. The catalyst is also shown to dehydrate other alcohols and ether substrates. The catalyst is resistant to deactivation and maintains activity between runs.Type: ApplicationFiled: September 16, 2011Publication date: March 21, 2013Applicant: Eastman Chemical CompanyInventor: David William Norman
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Publication number: 20120222422Abstract: A method is disclosed of coupling and integrating natural gas recovery and separation along with chemical conversion. The method can comprise extracting at least one natural gas component. Non-limiting examples of the extracted component include ethane, propane, butanes, and pentanes. The method can also comprise contacting a natural gas stream with a catalyst under conditions that selectively convert at least one component into at least one product, such as ethylene, acetic acid, polyethylene, vinyl acetate, ethylene vinyl acetate, ethylene oxide, ethylene glycol, and their derivatives, propylene, polypropylene, propylene oxide, propylene glycol, acrylates, acrolein, acrylic acid, butenes, butadiene, methacrolein, methacrylic acid, methacrylates, and their derivatives, which can then be separated from the remaining components.Type: ApplicationFiled: February 29, 2012Publication date: September 6, 2012Inventors: Mark Allen Nunley, Madan Mohan Bhasin, William George Etzkorn, George Ernest Keller, II, Parvez H. Wadia
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Patent number: 7582777Abstract: The present invention is directed to unsaturated or derivatized long chain (C22-C50) polyunsaturated hydrocarbons and a method of preparing the long chain hydrocarbons via electrocoupling of C12-C26 fatty acids. It has been found that soapstock is an inexpensive source of starting materials for the present method. The present invention is also directed to compositions comprising the long chain polyunsaturated hydrocarbons, which can be used as reactive diluents and modifiers in latex, epoxy, alkyd and polymer compositions. In another aspect, the present invention is directed to derivitization or ozonolysis of the long chain polyunsaturated hydrocarbons. The present method is also useful for preparing C12-26 alkyl esters and C12-26 carbon chain compounds containing a terminal olefin.Type: GrantFiled: October 17, 2005Date of Patent: September 1, 2009Assignee: Archer-Daniels-Midland CompanyInventor: Paul D. Bloom
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Patent number: 7442844Abstract: A process for producing isoprene is provided, which includes continuously or intermittently supplying isobutylene and/or t-butanol, formaldehyde and water into an acidic aqueous solution, and reacting the reaction mixture while distilling away a mixture containing produced isoprene, water, unreacted starting materials and other low boiling point components from this reaction mixture to the outside of the reaction system, wherein the reaction is carried out while controlling the concentration of high boiling point byproducts, which is produced and accumulated in the reaction mixture, to fall within the range of 0.5-40 mass %.Type: GrantFiled: March 24, 2004Date of Patent: October 28, 2008Assignee: Kuraray Co., Ltd.Inventors: Osamu Yamada, Manabu Kusano, Nobuo Takayanagi, Hideki Arimoto
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Patent number: 7273961Abstract: The present invention is a process for quenching a reactor effluent stream. The reactor effluent stream comprises water, olefin product, and methanol and is further entrained with catalyst fines. The process removes water, catalyst fines, and methanol. Particularly, methanol removal from the reactor effluent stream is improved.Type: GrantFiled: January 22, 2004Date of Patent: September 25, 2007Assignee: ExxonMobil Chemical Patents Inc.Inventors: Malcolm G. Pettigrew, Wadie Malaty, Ram Mohan Lai Mallik
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Patent number: 6667423Abstract: For the production of a diene a process in three stages comprises a stage a) for decomposition of at least one tertiary alkyl ether in a mixture that contains at least one tertiary olefin, at least one alcohol and at least one residual ether, in the presence of a catalyst that comprises at least one mineral solid that is grafted by at least one organic group such as alkyl sulfonic acid, sulfonic aryl and/or sulfonic alkylaryl, a stage b) for purification of the olefin that is obtained in stage a), and a stage c) for oxidizing dehydrogenation of the tertiary olefin that is obtained in stage b) in the presence of a catalyst under conditions for obtaining a diene.Type: GrantFiled: September 9, 1999Date of Patent: December 23, 2003Assignee: Institut Francais du PetroleInventors: Claire Dumonteil, Alain Forestiere, Marie-Claire Marion
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Publication number: 20030114725Abstract: For the production of a diene a process in three stages comprisesType: ApplicationFiled: September 9, 1999Publication date: June 19, 2003Inventors: CLAIRE DUMONTEIL, ALAIN FORESTIERE, MARIE-CLAIRE MARION
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Patent number: 5264644Abstract: The invention relates to a process for the preparation of a conjugated diene from the corresponding carbonyl compound having the same number of carbon atoms by dehydration at a temperature of 300.degree. to 450.degree. C. using a catalyst comprising aluminium phosphate having the cristobalite structure. This catalyst is superior to aluminium phosphate having the tridymite structure in the dehydration of carbonyl compounds and has advantages over boron phosphate catalysts. Using the process, isoprene may be prepared from 2-methyl butanal and/or methyl isopropyl ketone in high yields. Unexpectedly aluminium phosphate having the cristobalite structure is markedly superior to boron phosphate in converting methyl isopropyl ketone, which is an intermediate product formed in appreciable amounts in the dehydration of 2-methyl butanal to isoprene. This superiority significantly improves the process economics of the conversion reaction of 2-methyl butanal to isoprene.Type: GrantFiled: February 5, 1993Date of Patent: November 23, 1993Assignee: Enichem Elastomers LimitedInventors: Ian D. Hudson, Graham J. Hutchings
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Patent number: 5177290Abstract: The present invention is directed to a process for producing dienes which involves reacting a reaction mixture of tertiary alkyl ether and a source of oxygen over two functionally distinct catalysts under reaction conditions sufficient to produce high yields of the dienes with minimal recycle of the ether. The two functionally different catalysts are selected from a group of bifunctional catalysts having both oxidation sites and acidic sites and monofunctional acidic catalysts, such as bifunctional catalysts containing components selected from a group of oxides of vanadium, tungsten, molybdenum, copper, iron, chromium, and uranium and mixtures thereof; and monofuctional acid catalysts such as acid treated montmorillonite clays, and acid catalysts comprising an inorganic amorphous or substantially amorphous oxide material comprising the following components reacted therein:M.sup.1 /M.sup.2 /P/Owherein M.sup.1 is at least one Group IIIB element selected from the group consisting of Al, Ga, In and Tl; M.sup.Type: GrantFiled: January 10, 1991Date of Patent: January 5, 1993Assignee: Exxon Chemical Patents Inc.Inventors: Ji-Yong Ryu, Robert C. Michaelson
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Patent number: 5124498Abstract: The invention provides, in a first aspect, a method for preparing a reduced metal reagent comprising the steps of providing a halide salt of a metal having a more positive reduction potential than Na in admixture with liquid Na in substantially stoichiometric quantities in the presence of an ogranic solvent characterized by boiling point, measured at atmospheric conditions, at least equal to the melting point of Na, to reduce substantially all of the halide salt to reactive metal reagent and to convert substantially all of said Na to a Na halide salt.The invention further provides, in a second aspect, a method for converting carbonylsin the presnece of the reduced metal reagent prepared in accordance with the invention.Type: GrantFiled: October 16, 1990Date of Patent: June 23, 1992Assignee: Mobil Oil CorporationInventor: Dong M. Shen
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Patent number: 4899002Abstract: A process for the increased production of olefinic gasoline is described incorporating the integration of olefins to gasoline conversion under moderate severity conditions in contact with zeolite type catalyst with oxygenates to olefins conversion. The product of the olefins to gasoline conversion is passed to an olefins to gasoline and distillate (MOGD) conversion zone for distillate production. Liquid recycle requirements, feed throughput and/or the number of MOGD fixed bed stages are reduced for the MOGD process and overall process costs are lowered. The process includes the use of common catalyst handling and regeneration steps for the integrated processes.Type: GrantFiled: July 25, 1988Date of Patent: February 6, 1990Assignee: Mobil Oil Corp.Inventors: Mohsen N. Harandi, Hartley Owen
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Patent number: 4734538Abstract: Aldehydes can be converted to dienes by contacting the aldehydes with a non-zeolitic molecular sieve. Preferably the non-zeolitic molecular sieve has, in its calcined form, an adsorption of isobutane of at least about 2 percent by weight of the non-zeolitic molecular sieve at a partial pressure of 500 torr and a temperature of 20.degree. C. The non-zeolitic molecular sieves can achieve good conversion rates and selectivities for the reaction. The reaction is especially useful for the conversion of 2-methylbutyraldehyde to isoprene.Type: GrantFiled: December 24, 1986Date of Patent: March 29, 1988Assignee: Union Carbide CorporationInventors: George L. O'Connor, Steven W. Kaiser, James H. McCain
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Patent number: 4713458Abstract: Ketones and aldehydes are converted to ethenylidene-containing compounds by reaction thereof with dimethyl carbonate and a phosphine compound.Type: GrantFiled: August 21, 1984Date of Patent: December 15, 1987Assignee: The Dow Chemical CompanyInventors: Kevin A. Frazier, James M. Renga
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Patent number: 4684758Abstract: 2,5-Dimethyl-2,4-hexadiene which is an intermediate for preparing agricultural chemicals, insecticides or medicines, is prepared by bringing isobutylene and/or tert.-butyl alcohol into contact with isobutyl aldehyde in a gaseous phase at a temperature of 150.degree.-350.degree. C. in the presence of a niobic acid catalyst.Type: GrantFiled: July 31, 1986Date of Patent: August 4, 1987Assignee: Sumitomo Chemical Company, Ltd.Inventors: Yasuhiko Higashio, Kazuteru Takahashi
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Patent number: 4665266Abstract: This invention is directed to a process and a catalyst for the conversion of an aldehyde to a diolefin comprising contacting an aldehyde of 4 to 6 carbon atoms in the vapor phase at a temperature of 200.degree. to 300.degree. C. with a polymer bound dehydration catalyst. More specifically, this invention is concerned with a process for the catalytic dehydration of 2-methylbutanal (2MBA) to isoprene in the vapor phase with a polymer bound dehydration catalyst.Type: GrantFiled: August 6, 1986Date of Patent: May 12, 1987Assignee: The Goodyear Tire & Rubber CompanyInventors: Wen-Liang Hsu, Neil A. Maly
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Patent number: 4628140Abstract: This invention is directed to an improved process for the conversion of an aldehyde to a diolefin comprising contacting an aldehyde of 4 to 6 carbon atoms in the vapor phase at a temperature of 250.degree. to 400.degree. C. with a catalyst, the improvement comprising the addition of from 0.10 to 5 percent by weight of an aromatic compound to the aldehyde feed. Representative of the aromatic compounds useful in the instant invention are: phenol, catechol, alkylated catechol, resorcinol, hydroquinone and aniline; wherein the alkyl radical can be from 1 to 10 carbon atoms.Type: GrantFiled: March 3, 1986Date of Patent: December 9, 1986Assignee: The Goodyear Tire & Rubber CompanyInventor: Lawson G. Wideman
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Patent number: 4587372Abstract: This invention is concerned with improved boron phosphate dehydration catalysts. More specifically, this invention is directed to a process for the conversion of an aldehyde to a diolefin comprising contacting an aldehyde of 4 to 6 carbon atoms in the vapor phase with a catalyst comprising boron phosphate wherein the boron phosphate has been treated with an ammonium carbonate or bicarbonate salt prior to calcination. This invention is also concerned with a large port catalyst for dehydration reactions wherein the improvement comprises the use of a catalyst with a molar ratio of P/B of about 1.0 modified with from 0.1 to 10 mole percent, based on moles of boron, of a carbonate salt selected from (NH.sub.4).sub.2 CO.sub.3 and NH.sub.4 HCO.sub.3.Type: GrantFiled: August 2, 1985Date of Patent: May 6, 1986Assignee: The Goodyear Tire & Rubber CompanyInventor: Wen-Liang Hsu
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Patent number: 4560822Abstract: Dienes are prepared by dehydration of aldehydes at elevated temperatures by a method in which the dehydration is carried out using a zeolite as a catalyst.Type: GrantFiled: May 3, 1985Date of Patent: December 24, 1985Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Gerd Fouquet
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Patent number: 4547614Abstract: An improved process for the preparation of conjugated dienes, particularly isoprene, from the corresponding aliphatic aldehyde using an acidic dehydration catalyst is disclosed. The present invention embraces the surprising discovery that catalyst activity and selectivity, particularly for boron phosphate catalyst, can be substantially prolonged by reducing the aldehyde liquid hourly space velocity to less than about 3.0 hr.sup.-1 and preferably to less than about 1.0 hr.sup.-1.Type: GrantFiled: September 20, 1983Date of Patent: October 15, 1985Assignee: Monsanto CompanyInventor: Atis Vavere
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Patent number: 4524233Abstract: This invention is directed to a process for the conversion of an aldehyde to a diolefin comprising contacting an aldehyde of 4 to 6 carbon atoms in the vapor phase at a temperature of 300.degree. to 400.degree. C. with a catalyst comprising boron phosphate wherein the initial molar ratio of phosphorous (P) to boron (B) (P/B) is less than 1.0 but greater than 0.6 which is in intimate admixture with from 0.1 to 10 weight percent graphite. More specifically, this invention is concerned with a process for the catalytic dehydration of 2-methylbutanal (2MBA) to isoprene in the vapor phase with a boron phosphate catalyst wherein the improvement comprises the use of a catalyst with a molar ratio of P/B of less than 1.0 but greater than 0.6 which contains from 0.1 to 10 weight percent graphite and 0 to 10 mole percent, based on moles of boron, of ammonia or an amine selected from the group consisting of mono-, di- and/or tri- alkyl amines of 1 to 10 carbon atoms.Type: GrantFiled: September 10, 1984Date of Patent: June 18, 1985Assignee: The Goodyear Tire & Rubber CompanyInventors: Wen-Liang Hsu, Neil A. Maly, Barry A. Matrana, Robert W. Strozier, Lawson G. Wideman
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Patent number: 4381416Abstract: A process for producing isoprene, which comprises decomposing a mixture of at least two compounds represented by the general formula ##STR1## wherein (i) W and Y each represent a hydrogen atom, and X and Z are identical or different and each represent the group OR, (ii) W and X together form a single bond, Y represents a hydrogen atom and Z represents the group OR, (iii) W represents a hydrogen atom, X and Y together form a single bond, and Z represents the group OR, or (iv) W represents a hydrogen atom, X represents the group OR, and Y and Z together form a single bond, in which R represents a hydrogen atom, a methyl group, a methoxymethyl group, a methylbutenyl group, a methylbutenyloxymethyl group, a 1,1-dimethyl-3-hydroxypropyl group, a 1,1-dimethyl-3-hydroxypropyloxymethyl group, a 3-methyl-3-hydroxybutyl group, a 3-methyl-3-hydroxybutyloxymethyl group, a 1,1-dimethyl-3-methoxypropyl group, a 1,1-dimethyl-3-methoxypropyloxymethyl group, a 3-methyl-3-methoxybutyl group or a 3-methyl-3-methoxybutyloxymethyType: GrantFiled: December 1, 1980Date of Patent: April 26, 1983Assignee: Kuraray Co., Ltd.Inventors: Sunao Kyo, Tumoru Renge, Katsumi Omura
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Patent number: 4338478Abstract: A process for producing a conjugated diene represented by the general formula ##STR1## wherein R.sub.3, R.sub.4 and R.sub.5 each represent a hydrogen atom, or any one of them represents a methyl group and the other two each represent a hydrogen atom,which comprises heating an alkane-1,3-diol represented by the general formula ##STR2## wherein R.sub.1 and R.sub.2 each represent a hydrogen atom, or one of them represents a hydrogen atom and the other represents a methyl group,to a temperature of at least 130.degree. C. in the liquid phase in the presence of water and a boron-oxyacid or an oxygen-containing boron compound capable of forming a boron-oxyacid it under the reaction conditions.Type: GrantFiled: December 18, 1980Date of Patent: July 6, 1982Assignee: Kuraray Co., Ltd.Inventors: Sunao Kyo, Katsumi Omura, Ken-ichi Hino
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Patent number: 4266084Abstract: Commercially attractive amounts of benzene and toluene can be obtained from a solid mixture of aldehydo-, carboxy-, keto- and carboxy-, carboxy- and aldehydo-substituted benzene and toluene including such mixtures also containing cobalt and manganese salts of organic acids and inorganic and organic bromides obtained from the manufacture of benzene di- and tricarboxylic acids by non-catalytic pyrolysis of such mixture or gases and vapors therefrom at a temperature of at least 700.degree. C. Such non-catalytic pyrolysis is more technically attractive than catalytic pyrolysis conducted at a temperature of from 300.degree. C. to 500.degree. C. which has a short activity life.Type: GrantFiled: October 19, 1979Date of Patent: May 5, 1981Assignee: Standard Oil Company (Indiana)Inventor: John K. Allen