O-containing Patents (Class 585/606)
  • Patent number: 11976017
    Abstract: The present invention relates to processes for preparing isoprene and mono-olefins comprising at least six carbon atoms.
    Type: Grant
    Filed: November 11, 2020
    Date of Patent: May 7, 2024
    Assignee: Dow Technology Investments LLC
    Inventors: Marinus A. Bigi, Michael A. Brammer, Glenn A. Miller, Amarnath Singh
  • Patent number: 11446635
    Abstract: 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: Grant
    Filed: December 27, 2018
    Date of Patent: September 20, 2022
    Assignee: SEKISUI CHEMICAL CO., LTD.
    Inventors: Haruka Nishiyama, Noritoshi Yagihashi, Toshihito Miyama
  • Patent number: 10196326
    Abstract: 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: Grant
    Filed: February 22, 2016
    Date of Patent: February 5, 2019
    Assignee: versalis S.p.A.
    Inventors: Stefano Ramello, Vittorio Milanesi, Roberto Buzzoni
  • Publication number: 20150105598
    Abstract: 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: Application
    Filed: May 15, 2013
    Publication date: April 16, 2015
    Applicant: KURARAY CO., LTD.
    Inventors: Osamu Nakayama, Junichi Fuji, Masaki Shimizu
  • Patent number: 8933285
    Abstract: 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: Grant
    Filed: November 25, 2009
    Date of Patent: January 13, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Melvin L. Luetkens, Jr., Steven A. Cohen, Chander Balakrishnan
  • Publication number: 20140024872
    Abstract: 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: Application
    Filed: July 12, 2013
    Publication date: January 23, 2014
    Inventors: Joshua Silverman, Sol M. Resnick, Michael Mendez
  • Publication number: 20130072696
    Abstract: 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: Application
    Filed: September 16, 2011
    Publication date: March 21, 2013
    Applicant: Eastman Chemical Company
    Inventor: David William Norman
  • Publication number: 20120222422
    Abstract: 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: Application
    Filed: February 29, 2012
    Publication date: September 6, 2012
    Inventors: Mark Allen Nunley, Madan Mohan Bhasin, William George Etzkorn, George Ernest Keller, II, Parvez H. Wadia
  • Patent number: 7582777
    Abstract: 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: Grant
    Filed: October 17, 2005
    Date of Patent: September 1, 2009
    Assignee: Archer-Daniels-Midland Company
    Inventor: Paul D. Bloom
  • Patent number: 7442844
    Abstract: 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: Grant
    Filed: March 24, 2004
    Date of Patent: October 28, 2008
    Assignee: Kuraray Co., Ltd.
    Inventors: Osamu Yamada, Manabu Kusano, Nobuo Takayanagi, Hideki Arimoto
  • Patent number: 7273961
    Abstract: 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: Grant
    Filed: January 22, 2004
    Date of Patent: September 25, 2007
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Malcolm G. Pettigrew, Wadie Malaty, Ram Mohan Lai Mallik
  • Patent number: 6667423
    Abstract: 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: Grant
    Filed: September 9, 1999
    Date of Patent: December 23, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Claire Dumonteil, Alain Forestiere, Marie-Claire Marion
  • Publication number: 20030114725
    Abstract: For the production of a diene a process in three stages comprises
    Type: Application
    Filed: September 9, 1999
    Publication date: June 19, 2003
    Inventors: CLAIRE DUMONTEIL, ALAIN FORESTIERE, MARIE-CLAIRE MARION
  • Patent number: 5264644
    Abstract: 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: Grant
    Filed: February 5, 1993
    Date of Patent: November 23, 1993
    Assignee: Enichem Elastomers Limited
    Inventors: Ian D. Hudson, Graham J. Hutchings
  • Patent number: 5177290
    Abstract: 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: Grant
    Filed: January 10, 1991
    Date of Patent: January 5, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Ji-Yong Ryu, Robert C. Michaelson
  • Patent number: 5124498
    Abstract: 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: Grant
    Filed: October 16, 1990
    Date of Patent: June 23, 1992
    Assignee: Mobil Oil Corporation
    Inventor: Dong M. Shen
  • Patent number: 4899002
    Abstract: 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: Grant
    Filed: July 25, 1988
    Date of Patent: February 6, 1990
    Assignee: Mobil Oil Corp.
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4734538
    Abstract: 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: Grant
    Filed: December 24, 1986
    Date of Patent: March 29, 1988
    Assignee: Union Carbide Corporation
    Inventors: George L. O'Connor, Steven W. Kaiser, James H. McCain
  • Patent number: 4713458
    Abstract: Ketones and aldehydes are converted to ethenylidene-containing compounds by reaction thereof with dimethyl carbonate and a phosphine compound.
    Type: Grant
    Filed: August 21, 1984
    Date of Patent: December 15, 1987
    Assignee: The Dow Chemical Company
    Inventors: Kevin A. Frazier, James M. Renga
  • Patent number: 4684758
    Abstract: 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: Grant
    Filed: July 31, 1986
    Date of Patent: August 4, 1987
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Yasuhiko Higashio, Kazuteru Takahashi
  • Patent number: 4665266
    Abstract: 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: Grant
    Filed: August 6, 1986
    Date of Patent: May 12, 1987
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Neil A. Maly
  • Patent number: 4628140
    Abstract: 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: Grant
    Filed: March 3, 1986
    Date of Patent: December 9, 1986
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Lawson G. Wideman
  • Patent number: 4587372
    Abstract: 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: Grant
    Filed: August 2, 1985
    Date of Patent: May 6, 1986
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Wen-Liang Hsu
  • Patent number: 4560822
    Abstract: 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: Grant
    Filed: May 3, 1985
    Date of Patent: December 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Gerd Fouquet
  • Patent number: 4547614
    Abstract: 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: Grant
    Filed: September 20, 1983
    Date of Patent: October 15, 1985
    Assignee: Monsanto Company
    Inventor: Atis Vavere
  • Patent number: 4524233
    Abstract: 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: Grant
    Filed: September 10, 1984
    Date of Patent: June 18, 1985
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Neil A. Maly, Barry A. Matrana, Robert W. Strozier, Lawson G. Wideman
  • Patent number: 4381416
    Abstract: 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-methoxybutyloxymethy
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: April 26, 1983
    Assignee: Kuraray Co., Ltd.
    Inventors: Sunao Kyo, Tumoru Renge, Katsumi Omura
  • Patent number: 4338478
    Abstract: 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: Grant
    Filed: December 18, 1980
    Date of Patent: July 6, 1982
    Assignee: Kuraray Co., Ltd.
    Inventors: Sunao Kyo, Katsumi Omura, Ken-ichi Hino
  • Patent number: 4266084
    Abstract: 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: Grant
    Filed: October 19, 1979
    Date of Patent: May 5, 1981
    Assignee: Standard Oil Company (Indiana)
    Inventor: John K. Allen