Hetero Ring Containing Reactant Patents (Class 568/483)
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Patent number: 10550057Abstract: Disclosed is a two-step process to make a dialdehyde. In the process a diepoxide is first hydrolyzed with an alcohol solvent to an intermediate which is then subjected to a double-Pinacol rearrangement to obtain a dialdehyde. The dialdehydes have utility as chemical intermediates, and particular utility in processes to make enol ether compounds which can be used in applications as plasticizers, diluents, wetting agents, coalescing aids and as intermediates in chemical processes.Type: GrantFiled: September 4, 2019Date of Patent: February 4, 2020Assignee: Eastman Chemical CompanyInventor: Matthew Allen Boone
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Patent number: 10087404Abstract: An object of the present invention is to provide a biological corrosion inhibitor for a metal, which exhibits the effect at a low concentration and is superior in biodegradability. A biological corrosion inhibitor for a metal including 3-methylglutaraldehyde as an effective ingredient is provided.Type: GrantFiled: September 14, 2015Date of Patent: October 2, 2018Assignee: KURARAY CO., LTD.Inventors: Takuo Tsuruta, Ryosuke Shimizu, Takahiro Hosono, Junichi Fuji, Satoshi Wakai
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Publication number: 20150044346Abstract: The present invention relates to compounds based on an oxazoline moiety which liberate Strecker aldehydes under mild and controllable conditions. In addition the invention relates to food products comprising such compounds, and uses of such compounds.Type: ApplicationFiled: March 19, 2013Publication date: February 12, 2015Inventors: Imre Blank, Thomas Davidek, Ondrej Novotny, Peter Schieberle, Michael Granvogl
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Patent number: 8779213Abstract: The present invention relates to a bio-based glutaraldehyde compound and to the different non-fossil, natural raw material manufacture methods thereof. To prepare said compound, glycerol created by the methanolysis of vegetable oil or animal fat is used, leading after dehydration to acrolein that is caused to react with a vinyl/alkyl/ether as per a Diels-Alder cyclization reaction, followed by hydrolysis so as to obtain the bio-based glutaraldehyde of the invention. Sugars containing five carbon atoms, that is, pentoses created from for example hemicellulose, may also be used, leading after dehydration to furfural, which leads, after complete hydrogenation followed by selective oxidation, to the bio-based glutaraldehyde of the invention.Type: GrantFiled: October 19, 2010Date of Patent: July 15, 2014Assignee: Arkema FranceInventors: Jean Luc Couturier, Jean Luc Dubois
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Patent number: 8686192Abstract: Methods of converting cellulose or related biorenewable carbohydrate materials into high-value chemical compounds. The methods provide a means of converting low-cost materials such as cellulose and biomass into high yields of compounds such as ethylene glycol, propylene glycol, glycerin, methanol, hydroxyacetone, glycolaldehyde and dihydroxyacetone.Type: GrantFiled: August 24, 2012Date of Patent: April 1, 2014Assignee: Iowa State University Research Foundation, Inc.Inventors: Walter S. Trahanovsky, Ronald C. Holtan, Kyle W. Quasdorf, Norman K. Olson, Alyse A. Dilts, Joseph A. Marshall
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Publication number: 20130090474Abstract: The application discloses a process for the preparation of 5-deoxy-L-arabinose of formula (VI); comprising the conversion of a compound of formula (XII); wherein n is 0, 1 or 2; which can be used as intermediate for the synthesis of sapropterin.Type: ApplicationFiled: June 13, 2011Publication date: April 11, 2013Applicant: DIPHARMA FRANCIS S.R.L.Inventors: Emanuele Attolino, Mario Michieletti, Davide Rossi, Pietro Allegrini
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Publication number: 20130060067Abstract: Methods of converting cellulose or related biorenewable carbohydrate materials into high-value chemical compounds. The methods provide a means of converting low-cost materials such as cellulose and biomass into high yields of compounds such as ethylene glycol, propylene glycol, glycerin, methanol, hydroxyacetone, glycolaldehyde and dihydroxyacetone.Type: ApplicationFiled: August 24, 2012Publication date: March 7, 2013Applicant: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.Inventors: Walter S. Trahanovsky, Ronald C. Holtan, Kyle W. Quasdorf, Norman K. Olson, Alyse A. Dilts, Joseph A. Marshall
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Patent number: 8383864Abstract: Methods of converting cellulose or related biorenewable carbohydrate materials into high-value chemical compounds. The methods provide a means of converting low-cost materials such as cellulose and biomass into high yields of compounds such as ethylene glycol, propylene glycol, glycerin, methanol, hydroxyacetone, glycolaldehyde and dihydroxyacetone.Type: GrantFiled: December 8, 2010Date of Patent: February 26, 2013Assignee: Iowa State University Research Foundation, Inc.Inventors: Walter S. Trahanovsky, Ronald C. Holtan, Kyle W. Quasdorf, Norman K. Olson, Alyse A. Hurd, Joseph A. Marshall
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Publication number: 20120277475Abstract: The present invention relates to a bio-based glutaraldehyde compound and to the different non-fossil, natural raw material manufacture methods thereof. To prepare said compound, glycerol created by the methanolysis of vegetable oil or animal fat is used, leading after dehydration to acrolein that is caused to react with a vinyl/alkyl/ether as per a Diels-Alder cyclization reaction, followed by hydrolysis so as to obtain the bio-based glutaraldehyde of the invention. Sugars containing five carbon atoms, that is, pentoses created from for example hemicellulose, may also be used, leading after dehydration to furfural, which leads, after complete hydrogenation followed by selective oxidation, to the bio-based glutaraldehyde of the invention.Type: ApplicationFiled: October 19, 2010Publication date: November 1, 2012Applicant: ARKEMA FRANCEInventors: Jean Luc Couturier, Jean Luc Dubois
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Publication number: 20110137085Abstract: Methods of converting cellulose or related biorenewable carbohydrate materials into high-value chemical compounds. The methods provide a means of converting low-cost materials such as cellulose and biomass into high yields of compounds such as ethylene glycol, propylene glycol, glycerin, methanol, hydroxyacetone, glycolaldehyde and dihydroxyacetone.Type: ApplicationFiled: December 8, 2010Publication date: June 9, 2011Applicant: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.Inventors: WALTER S. TRAHANOVSKY, RONALD C. HOLTAN, KYLE W. QUASDORF, NORMAN K. OLSON, ALYSE A. HURD, JOSEPH A. MARSHALL
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Patent number: 7709686Abstract: Provided is a process for the preparation of glutaraldehyde. The process comprises reacting an alkoxydihydropyran with water in the presence of an acidic catalyst. The alcohol by-product distilled from the reaction mixture is subjected to a heterogeneous catalyst that is located external to the distillation column used for distilling the alcohol, thereby increasing glutaraldehyde yield and decreasing the level of alkoxydihydropyran contamination in the alcohol.Type: GrantFiled: June 9, 2009Date of Patent: May 4, 2010Assignee: Dow Global Technologies Inc.Inventors: Charles D. Gartner, Timothy D. Ligon
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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: 20090318735Abstract: Provided is a process for the preparation of glutaraldehyde. The process comprises reacting an alkoxydihydropyran with water in the presence of an acidic catalyst. The alcohol by-product distilled from the reaction mixture is subjected to a heterogeneous catalyst that is located external to the distillation column used for distilling the alcohol, thereby increasing glutaraldehyde yield and decreasing the level of alkoxydihydropyran contamination in the alcohol.Type: ApplicationFiled: June 9, 2009Publication date: December 24, 2009Inventors: Charles D. Gartner, Timothy D. Ligon
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Patent number: 7547808Abstract: To provide a process capable of producing an aldehyde with a 2-position branched long-chain alkyl with high yield and high selectivity. The process for producing an aldehyde with a 2-position branched long-chain alkyl represented by the following general formula (2) contains: using a 2-position branched epoxide represented by the following general formula (1) as a raw material; and subjecting the epoxide to acid rearrangement reaction with a polyacid of a metallic oxoacid as a catalyst. In the formulae, n represents an integer of from 5 to 17.Type: GrantFiled: July 21, 2006Date of Patent: June 16, 2009Assignee: Idemitsu Kosan Co., Ltd.Inventors: Haruhito Sato, Takashi Kashiwamura, Yoshio Ikeda
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Publication number: 20090076311Abstract: To provide a process capable of producing an aldehyde with a 2-position branched long-chain alkyl with high yield and high selectivity. The process for producing an aldehyde with a 2-position branched long-chain alkyl represented by the following general formula (2) contains: using a 2-position branched epoxide represented by the following general formula (1) as a raw material; and subjecting the epoxide to acid rearrangement reaction with a polyacid of a metallic oxoacid as a catalyst. In the formulae, n represents an integer of from 5 to 17.Type: ApplicationFiled: July 21, 2006Publication date: March 19, 2009Applicant: Idemitsu Kosan Co., Ltd.Inventors: Haruhito Sato, Takashi Kashiwamura, Yoshio Ikeda
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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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Patent number: 7410504Abstract: Adducts are obtained by reacting carbonyl compounds of the formula I where R1 and R2 are as defined, with cyclic compounds of the formula II where X is selected from oxygen, sulfur and N—R8, R3-R8 are as defined, and n is an integer from 1 to 4, which adducts are useful as tanning agents and preservatives.Type: GrantFiled: January 21, 2004Date of Patent: August 12, 2008Assignee: BASF AktiengesellschaftInventors: Stephan Hueffer, Oliver Reese, Walter Gramlich, Stefan Schroeder, Guenter Scherr, Volker Bach
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Patent number: 7071363Abstract: The invention relates to a novel structured catalyst bed which optionally comprises at least one part bed comprising at least one catalytically active mixture of oxides of the main group metals and transition metals and additionally comprises at least one catalytically active part bed comprising at least silver, at least one alkali metal and a porous support material and finally and necessarily at least one catalytically active part bed comprising at least one alkali metal phosphate and at least one sheet silicate.Type: GrantFiled: July 14, 2003Date of Patent: July 4, 2006Assignee: BASF AktiengesellschaftInventors: Hartmut Hibst, Sebastian Storck, Dirk Demuth, Wolfram Stichert, Jens Klein, Stephan A. Schunk, Andreas Sundermann
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Patent number: 6803491Abstract: A new method for preparing lithium phosphate catalysts is disclosed. The method comprises precipitating a lithium phosphate from a mixture comprising a first aqueous solution which contains lithium and sodium ions and a second aqueous solution which contains phosphate and borate ions. The resultant lithium phosphate catalyst has increased activity and selectivity in the isomerization of an alkylene oxide to the corresponding allylic alcohol.Type: GrantFiled: November 13, 2003Date of Patent: October 12, 2004Assignee: Arco Chemical Technology, L.P.Inventor: Wilfred Po-sum Shum
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Patent number: 6559346Abstract: In a process for the continuous preparation of glutaraldehyde by reaction of an alkoxydihydropyran of the formula I where R is C1-C20-alkyl, with water at from 0° C. to 200° C. and a pressure in the range from 0.01 bar to 16 bar to form glutaraldehyde and the alcohol corresponding to the alkoxy group, water and alkoxydihydropyran are fed continuously to a reaction column and a distillate enriched in the alcohol corresponding to the alkoxy group is taken off at the top of the column and a product enriched in glutaraldehyde is taken off at the bottom. This process makes it possible to prepare glutaraldehyde or C-substituted glutaraldehydes continuously in high purity in a simple manner with a low outlay in terms of apparatus.Type: GrantFiled: February 28, 2002Date of Patent: May 6, 2003Assignee: BASF AktiengesellschaftInventors: Jörg Therre, Carsten Oost
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Patent number: 6376724Abstract: Ethylene oxide is hydroformylated to 3-hydroxypropanal using a non-phosphine-ligated cobalt catalyst and a primary or secondary amine promoter.Type: GrantFiled: June 15, 2001Date of Patent: April 23, 2002Assignee: Arco Chemical Technology, L.P.Inventor: Yuan-Zhang Han
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Patent number: 6376720Abstract: Ethylene oxide is hydroformylated to 3-hydroxypropanal using a non-phosphine-ligated cobalt catalyst and diamine promoter.Type: GrantFiled: June 15, 2001Date of Patent: April 23, 2002Assignee: Arco Chemical Technology, L.P.Inventor: Yuan-Zhang Han
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Patent number: 6323374Abstract: Ethylene oxide is hydroformylated to 3-hydroxypropanal using a non-phosphine-ligated cobalt catalyst and an amide promoter.Type: GrantFiled: June 15, 2001Date of Patent: November 27, 2001Assignee: Arco Chemical Technology, L.P.Inventor: Yuan-Zhang Han
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Patent number: 6201156Abstract: An ether of the following formula (2): (wherein Ra is a hydrogen atom, a hydrocarbon group or a heterocyclic group, Rb is a hydrogen atom, a hydroxyl group or a substituted oxy group, and Rc is a hydrocarbon group or a heterocyclic group; Ra and Rc may be combined to form a ring with the adjacent carbon atom and oxygen atom) is reacted with nitrogen monoxide in the presence of a catalyst composed of an imide compound of the following formula (1): (wherein each of R1 and R2 is, identical to or different from each other, a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or an acyl group; R1 and R2 may be combined to form a double bond, or an aromatic or nonaromatic ring; X is an oxygen atom or a hydroxyl group; and one or two N-substituted cyclic imido groups indicated in the formula (1) may further be formed on R1, R2, or on the double bond or aromatic or nonaromatType: GrantFiled: September 13, 1999Date of Patent: March 13, 2001Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 6180838Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated rhodium catalyst and a catalyst promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100° C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing rhodium catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol. The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified rhodium catalyst.Type: GrantFiled: March 20, 1996Date of Patent: January 30, 2001Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell
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Patent number: 6180831Abstract: &bgr;-Hydroxyaldehydes are produced by a method in which 1,2-oxiranes are reacted with carbon monoxide and hydrogen in the presence of transitional metal compounds which are modified with phosphorus-oxygen ligands or nitrogen-oxygen ligands and which act as a catalyst.Type: GrantFiled: November 12, 1999Date of Patent: January 30, 2001Assignee: Degussa-Huls AGInventors: Robert Weber, Wilhelm Keim, Bernd Jaeger, Thomas Haas, Rudolf Vanheertum
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Patent number: 6133409Abstract: This invention is directed to a process for the solid phase synthesis of aldehyde, ketone, oxime, amine, hydroxamic acid and .alpha.,.beta.-unsaturated carboxylic acid and aldehyde compounds and to polymeric hydroxylamine resin compounds useful therefor.Type: GrantFiled: June 24, 1998Date of Patent: October 17, 2000Assignee: Aventis Pharmaceuticals Products Inc.Inventors: Joseph M. Salvino, George C. Morton, Helen J. Mason, Richard F. Labaudiniere
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Patent number: 5981808Abstract: 1,3-Propanediol is prepared in a process which involves reacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a catalyst promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt %; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxypropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol.The process enables the production of 1,3-propanediol in high yield and selectivity without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: July 15, 1997Date of Patent: November 9, 1999Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Lynn Henry Slaugh, David Cleve Eubanks, Stephan Blake Mullin, Terry Blain Thomason, Paul Richard Weider, Thomas Carl Semple
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Patent number: 5973209Abstract: A method is disclosed for preparing 3,3-dimethylbutyraldehyde by using silica gel to isomerize 3,3-dimethyl-1,2-epoxybutane, which in turn may be prepared by oxidation of dimethylbutene. Also disclosed is a method for oxidizing dimethylbutene with dimethyldioxirane to form 3,3-dimethyl-1,2-epoxybutane. The methods provide an economical means of preparing 3,3-dimethylbutyraldehyde.Type: GrantFiled: July 11, 1997Date of Patent: October 26, 1999Assignee: The NutraSweet CompanyInventors: Indra Prakash, Marie-Christine D. Chapeau
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Patent number: 5777182Abstract: 1,3-propanediol is prepared in a process which involves hydroformylating ethylene oxide:(a) in an essentially non-water-miscible solvent in the presence of a non-ligated cobalt catalyst and a catalyst promoter at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;(b) adding an aqueous liquid and extracting at a temperature less than about 100.degree. C. the 3-hydroxypropanal to provide an aqueous phase comprising 3-hydroxypropanal in greater concentration than the concentration of 3-hydroxypropanal in said intermediate product mixture, and an organic phase comprising the cobalt catalyst;(c) separating the aqueous phase from the organic phase;(d) hydrogenating the 3-hydroxypropanal to provide a hydrogenation product mixture comprising 1,3-propanediol; and(e) recovering 1,3-propanediol from said hydrogenation product mixture.Type: GrantFiled: August 26, 1996Date of Patent: July 7, 1998Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Lynn Henry Slaugh, Thomas Clayton Forschner, Jiang-Jen Lin, Terry Blane Thomason, Paul Richard Weider, Thomas Carl Semple, Juan Pedro Arhancet, Howard Lam-Ho Fong, Stephen Blake Mullin, Kevin Dale Allen, David Cleve Eubanks, David William Johnson
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Patent number: 5770776Abstract: 1,3-propanediol is prepared in a process in which ethylene oxide is reacted with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a catalyst promoter under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal. The 3-hydroxypropanal is extracted in water from the product mixture in more concentrated form, with the majority of the cobalt catalyst remaining in the solvent phase for recycle to the hydroformylation reaction. At least a portion of any residual catalyst in the water phase following extraction is removed by re-extraction with non-water-miscible solvent and recycled to hydroformylation. The 3-hydroxypropanal is then hydrogenated in aqueous solution to the desired 1,3-propanediol.Type: GrantFiled: March 11, 1996Date of Patent: June 23, 1998Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Stephen Blake Mullin, Paul Richard Weider, David Cleve Eubanks, Juan Pedro Arhancet
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Patent number: 5731478Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt or rhodium catalyst and a manganese porphyrine promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand with the cobalt or rhodium catalyst.Type: GrantFiled: October 15, 1996Date of Patent: March 24, 1998Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
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Patent number: 5723680Abstract: Aldehydes and/or alcohols are prepared by the hydroformylation of olefins of more than 3 carbon atoms by means of a bare rhodium catalyst dissolved homogeneously in the reaction medium, at superatmospheric pressure and at elevated temperatures, and separation of the rhodium catalyst from the liquid reaction mixture, by a process in which a magnetizable, inorganic pigment coated with a polymeric binder is used for separating the homogeneously dissolved, bare rhodium catalyst from the hydroformylation medium, and this pigment, after it has been laden with the rhodium contained in the hydroformylation medium, is separated from the liquid hydroformylation medium by applying an external magnetic field.Type: GrantFiled: April 18, 1997Date of Patent: March 3, 1998Assignee: BASF AktiengesellschaftInventors: Claudius Kormann, Heinz-Josef Kneuper
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Patent number: 5723498Abstract: A composition which is capable of releasing acrolein and is easy to handle contains (i) an acetal of acrolein with a C.sub.1-6 alcohol with 1 to 4 hydroxyl groups and (ii) an acid soluble therein and chemically compatible with a pK.sub.s value of less than 4 and (iii) is anhydrous. A preferred composition contains 2-vinyl-1,3-dioxolane as acetal, anhydrous oxalic acid, fumaric acid or maleic acid or a mixture of mono- and di(C.sub.1 - to C.sub.3 -)alkyl phosphate as acid and, in addition, a non-ionic surfactant. The acrolein is released at the site of use upon contact with for example water for the purpose of combatting microbial, vegetable and animal pests.Type: GrantFiled: September 13, 1995Date of Patent: March 3, 1998Assignee: Degussa AktiengellschaftInventors: Peter Werle, Martin Trageser, Oswald Helmling, Harold Jakob
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Patent number: 5723389Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt or rhodium catalyst and a cobalt or rhodium porphyrin promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand with the cobalt or rhodium catalyst.Type: GrantFiled: October 15, 1996Date of Patent: March 3, 1998Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
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Patent number: 5689016Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a rhodium promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: March 20, 1996Date of Patent: November 18, 1997Assignee: Shell Oil CompanyInventors: Paul Richard Weider, Lynn Henry Slaugh, Joseph Broun Powell
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Patent number: 5684214Abstract: A process for preparing 1,3-propanediol comprises the steps of:(a) reacting a cobalt salt selected from at least one of cobalt hydroxide, cobalt (II, III) oxide and cobalt carbonate with synthesis gas in an essentially non-water-miscible liquid medium under conditions effective to produce a cobalt carbonyl reaction product comprising at least one active cobalt carbonyl hydroformylation catalyst species;(b) contacting ethylene oxide with synthesis gas in an essentially non-water miscible liquid medium in the presence of a catalytic amount of the cobalt carbonyl reaction product mixture and an effective amount of a catalyst promoter under reaction conditions effective to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;(c) adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid a major portion of the 3-hydroxypropanal so as to provide an aqueous phase comprising 3-hydroxypropanal in greater concentration than the concentration oType: GrantFiled: October 31, 1995Date of Patent: November 4, 1997Assignee: Shell Oil CompanyInventors: Paul Richard Weider, Joseph Broun Powell, Khiet Thanh Lam
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Patent number: 5679868Abstract: A process for the preparation of glutaric dialdehyde by the reaction of alkoxy dihydropyrans of the general formula I ##STR1## in which R stands for C.sub.1 to C.sub.20 alkoxy, with water at temperatures ranging from 0.degree. to 150.degree. C. and pressures of from 0.01 to 50 bar in the presence of a which microporous, crystalline aluminum silicate catalyst, e.g. a beta-type zeolite or pentasil catalyst having a pore diameter greater than 5.4 .ANG..Type: GrantFiled: December 12, 1995Date of Patent: October 21, 1997Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Rainer Becker, Eugen Gehrer, Juergen Schossig, Andreas Henne
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Patent number: 5600018Abstract: A process for preparing glutaraldehyde by reaction of alkoxydihydropyrans of the general formula I ##STR1## where R is C.sub.1 -C.sub.20 -alkoxy, with water at from 0.degree. to 150.degree. C. and from 0.01 to 50 bar in the presence of a catalyst consisting essentially of a bleaching earth.Type: GrantFiled: August 7, 1995Date of Patent: February 4, 1997Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Wolfgang Friedrich, Walter Klink, Juergen Schossig, Andreas Henne
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Patent number: 5585528Abstract: 1,3-Propanediol is prepared in a process which involves reacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a lipophilic tertiary amine promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt %; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxypropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol.The process enables the production of 1,3-propanediol in high yield and selectivity without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: September 30, 1994Date of Patent: December 17, 1996Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Semple, Paul R. Weider
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Patent number: 5576471Abstract: 1,3-Propanediol is prepared in a process which involves reacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a lipophilic dihydroxyarene promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt %; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxypropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol.The process enables the production of 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: September 30, 1994Date of Patent: November 19, 1996Assignee: Shell Oil CompanyInventors: Thomas C. Semple, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Paul R. Weider
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Patent number: 5567855Abstract: Methods for stereospecific synthesis of 9-cis olefins and retinoids. In one particular aspect, a cis olefin is generated via a lactol ring opening with complete retention of double bond configuration.Type: GrantFiled: April 21, 1994Date of Patent: October 22, 1996Assignee: Ligand Pharmaceuticals IncorporatedInventors: Steven K. White, Chan K. Hwang, David T. Winn
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Patent number: 5563302Abstract: 1,3-Propanediol is prepared in a process which involves reacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a lipophilic phosphine oxide promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt %; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxpropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol.The process enables the production of 1,3-propanediol in high yields and selectively without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: September 30, 1994Date of Patent: October 8, 1996Assignee: Shell Oil CompanyInventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
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Patent number: 5545766Abstract: 1,3-Propanediol is prepared in a process which involves reacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a lipophilic bidentate phosphine promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt%; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxypropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol.The process enables the production of 1,3-propanediol in high yield and selectivity without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: September 30, 1994Date of Patent: August 13, 1996Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
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Patent number: 5545765Abstract: 1,3-Propanediol is prepared in a process which involves reacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a lipophilic quaternary arsonium salt promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt %; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxypropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol.The process enables the production of 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.Type: GrantFiled: September 30, 1994Date of Patent: August 13, 1996Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Joseph B. Powell, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
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Patent number: 5495050Abstract: A method for producing high purity chloroaldehyde monomers at a high yield by depolymerization of a chloroaldehyde cyclic trimer represented by the following formula, ##STR1## wherein R is a hydrogen atom, methyl group, or an ethyl group. The depolymerization reaction can be carried out in the presence of activated clay. Said chloroaldehyde cyclic trimer can be stored in a stable manner and chloroaldehyde monomers obtained by the depolymerization can be used as are as a raw material for the synthetic reaction of chloroaldehyde derivatives.Type: GrantFiled: October 20, 1994Date of Patent: February 27, 1996Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
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Patent number: 5406007Abstract: Disclosed is a process for the conversion of conjugated epoxyalkenes to unsaturated alcohols wherein a conjugated epoxyalkene is catalytically hydrogenated in the presence of a sulfur-modified or sulfided nickel catalyst whereby the epoxide ring is hydrogenolyzed without concomitant hydrogenation of the olefinic unsaturation thereby producing allylic and/or homoallylic alcohols.Type: GrantFiled: July 15, 1994Date of Patent: April 11, 1995Assignee: Eastman Chemical CompanyInventor: Stephen N. Falling
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Patent number: 5391773Abstract: Disclosed is a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycycloalkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and .gamma.,.delta.-epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.Type: GrantFiled: June 17, 1994Date of Patent: February 21, 1995Assignee: Eastman Chemical CompanyInventor: Thomas A. Puckette
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Patent number: 5386040Abstract: Low molecular weight polyacetals are prepared by reacting an acetal-containing reagent with a polyalcohol (e.g., glycerol or sucrose), a polyamine (e.g., 3,3'-diamine-N-methyl dipropylamine or ethylene diamine), a polyester (e.g., triethyl citrate), or a polyhalide (e.g., pentaerythrityl tetrabromide). Low molecular weight polyaldehydes are prepared by converting the acetal groups of the low molecular weight polyacetal to aldehyde groups or by reacting an aldehyde-containing reagent (e.g., glyoxal) with a polyamide.Type: GrantFiled: June 8, 1993Date of Patent: January 31, 1995Assignee: National Starch and Chemical Investment Holding CorporationInventors: Gary T. Martino, Martin M. Tessler
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Patent number: 5254701Abstract: Disclosed is a process for the production of an equilibrium mixture of 2-hydroxytetrahydrofuran and 4-hydroxybutanal by a two-step process comprising (1) heating 2,5-dihydrofuran in the presence of a catalyst system comprising a phosphine, ruthenium or rhodium to convert the 2,5-dihydrofuran to 2,3-dihydrofuran; and (2) contacting 2,3-dihydrofuran with water in the presence of an acidic catalyst to convert the 2,3-dihydrofuran to a mixture of 2-hydroxytetrahydrofuran and 4-hydroxybutanal. Also disclosed is a process for the continuous production of an aqueous solution of 2-hydroxytetrahydrofuran and 4-hydroxybutanal. The mixture of 2-hydroxytetra-hydrofuran and 4-hydroxybutanal may be catalytically hydrogenated to produce 1,4-butanediol.Type: GrantFiled: May 20, 1991Date of Patent: October 19, 1993Assignee: Eastman Kodak CompanyInventors: Stephen N. Falling, Gerald W. Phillips