By Reaction Of Aldehyde With Olefin (i.e.,by Prins Reaction) Patents (Class 568/879)
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Patent number: 11976030Abstract: The presently claimed invention relates to a process for the recovery of 3-methyl-3-buten-1-ol from a stream obtained in the production of 3-methyl-3-buten-1-ol from 2-methylprop-1-ene and formaldehyde, by treating the stream with an amine catalyst.Type: GrantFiled: September 13, 2019Date of Patent: May 7, 2024Assignee: BASF SEInventors: Andreas Keller, Roland Minges, Martin Kamasz, Gabriele Gralla, Bernhard Brunner
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Patent number: 10766840Abstract: The present invention relates to a process for preparing an unsaturated alcohol, preferably 3,7-dimethyl-2,6-octadienal, by contacting an alkene, preferably isobutene, with formaldehyde in the presence a condensation catalyst comprising a zeolitic material comprising the framework structure of which comprises a tetravalent element Y other than Si.Type: GrantFiled: February 27, 2018Date of Patent: September 8, 2020Assignee: BASF SEInventors: Andrei-Nicolae Parvulescu, Miriam Bru Roig, Albert Werner, Bernhard Brunner, Wolfgang Siegel, Stephan Maurer, Ulrich Mueller, Michael Ludwig Lejkowski
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Patent number: 10106484Abstract: Catalysts for dehydrating hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof to acrylic acid, acrylic acid derivatives, or mixtures thereof with high yield and selectivity, short residence time, and without significant conversion to undesired side products, such as, for example, acetaldehyde, propionic acid, and acetic acid, are provided. The catalysts are mixed condensed phosphates. Methods of preparing the catalysts are also provided.Type: GrantFiled: February 6, 2013Date of Patent: October 23, 2018Assignee: The Procter & Gamble CompanyInventors: Juan Estaban Velasquez, Janette Villalobos Lingoes, Jane Ellen Godlewski, Dimitris Ioannis Collias, Fred C. Wireko, Marc Andrew Mamak, Nancy Lee Redman-Furey
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Publication number: 20130261347Abstract: Hydrocarbons are oxidized to ethylene and/or oxygenates that comprise acetic acid. The acetic acid may be converted to ethanol by hydrogenation. The ethylene may be converted to ethanol by hydration.Type: ApplicationFiled: March 28, 2012Publication date: October 3, 2013Applicant: CELANESE INTERNATIONAL CORPORATIONInventors: Mark Scates, Heiko Weiner, Zhenhua Zhou, James Zink
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Publication number: 20120083630Abstract: Process for preparing homoallyl alcohols by catalyzed reaction of alkenes with aldehydes or ketones, wherein the reaction is carried out in the gas phase in the presence of noncovalently supported ionic liquid phase catalysts.Type: ApplicationFiled: October 4, 2011Publication date: April 5, 2012Applicant: BASF SEInventors: CHRISTOPH STOCK, Dirk Gerhard, Klaus Ebel
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Publication number: 20030109757Abstract: The present invention provides a method for separating and recovering propargyl alcohol from a product mixture containing a solvent, water and propargyl alcohol, which alleviates the problems of prior art and which can separate and recover propargyl alcohol in a simple operation at an advantageous thermal energy without requiring a large distillation unit or a complicated separation operation or step.Type: ApplicationFiled: November 8, 2002Publication date: June 12, 2003Inventors: Hideki Omori, Goro Sawada, Hideo Fukuda, Tomohiko Sato, Mitsuru Takeuchi
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Patent number: 6316680Abstract: In a process for isolating &agr;-ethynyl carbinols from the liquid reaction mixture from the addition of acetylene onto &agr;,&bgr;-unsaturated carbonyl compounds by distillation, the distillation is carried out continuously, the feed stream is introduced into the middle section of a distillation column (K), the major part of the water is distilled off azeotropically together with the solvent at the top of the column, and the &agr;-ethynyl carbinol target product is taken off below the feed point to the column.Type: GrantFiled: December 6, 1999Date of Patent: November 13, 2001Assignee: BASF AktiengesellschaftInventors: Ralf-Thomas Rahn, Harald Rust, Thomas Rühl, Jochem Henkelmann, Susanne Stutz
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Patent number: 5523495Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallylcarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.Type: GrantFiled: February 13, 1995Date of Patent: June 4, 1996Assignee: Sumitomo Chemical Company LimitedInventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
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Patent number: 5175378Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.Type: GrantFiled: March 16, 1992Date of Patent: December 29, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5175371Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.Type: GrantFiled: March 16, 1992Date of Patent: December 29, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4599453Abstract: A process for the single-stage production in the liquid or gaseous phase, of higher aliphatic ketones starting from ketones of lower molecular weight, characterized in that the starting ketones are reacted with carbon monoxide in the presence of a catalyst in the form of cooper supported on a metal oxide.The catalyst is prepared by depositing on the metal oxide the product obtained from hydrolyzing a cuprammonium solution, then calcining the solid system obtained in air and reducing the calcined product by means of hydrogen.Type: GrantFiled: February 25, 1985Date of Patent: July 8, 1986Assignee: Consiglio Nazionale Delle RicercheInventors: Carlo Fragale, Michele Gargano, Michele Rossi
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Patent number: 4571408Abstract: An .alpha.,.beta.-dihydropolyprenyl derivative having the formula (I): ##STR1## wherein X represents a group of --COOR.sub.1 or --CH.sub.2 OR.sub.2 in which R.sub.1 is the hydrogen atom or an alkyl group having one to four carbon atoms and R.sub.2 is the hydrogen atom or an aliphatic acyl group having one to four carbon atoms; and n is an integer of one to four. A process for the preparation of the .alpha.,.beta.-dihydropolyprenyl derivative and a therapeutic agent for treatment of liver diseases comprising the same are also disclosed.Type: GrantFiled: October 20, 1983Date of Patent: February 18, 1986Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Hideaki Watanabe, Toshiji Igarashi, Hiroyuki Shiojiri, Yoshio Tanabe, Kuniko Hara
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Patent number: 4503259Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.Type: GrantFiled: May 24, 1983Date of Patent: March 5, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
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Patent number: 4495359Abstract: Described is the genus of compounds defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein the wavy line represents a carbon-carbon single bond or no bond; wherein when the wavy line represents a carbon-carbon single bond, Z represents methylene and when the wavy line represents no bond, Z represents hydrogen or C.sub.2 -C.sub.Type: GrantFiled: May 5, 1983Date of Patent: January 22, 1985Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4481217Abstract: An .alpha.,.beta.-dihydropolyprenyl derivative having the formula (I): ##STR1## wherein X represents a group of --COOR.sub.1 or --CH.sub.2 OR.sub.2 in which R.sub.1 is the hydrogen atom or a lower alkyl group and R.sub.2 is the hydrogen atom or an aliphatic acyl group having one to four carbon atoms; and n is an integer of one to four. A process for the preparation of the .alpha.,.beta.-dihydropolyprenyl derivative and a therapeutic agent for treatment of liver diseases comprising the same are also disclosed.Type: GrantFiled: May 28, 1981Date of Patent: November 6, 1984Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Hideaki Watanabe, Toshiji Igarashi, Hiroyuki Shiojiri, Yoshio Tanabe, Kuniko Hara
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Patent number: 4288374Abstract: Tetrahydrofuran is prepared by reacting propylene and aqueous formaldehyde stabilized with alcohol in the presence of silica sand to form 3-buten-1-ol and chlorinating the 3-buten-1-ol in the presence of Group IA or IIA chloride to form 3,4-dichlorobutan-1-ol which is then treated with a Group IA or IIA base to form 3-chlorotetrahydrofuran which is then hydrogenated to form tetrahydrofuran.Type: GrantFiled: July 28, 1980Date of Patent: September 8, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Edward N. Squire
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Patent number: 4277633Abstract: The palladium complex disclosed herein is bis[tri(ortho-tolyl)phosphine] :palladium which is produced by reacting a palladium salt with tri(ortho-tolyl)phosphine and reducing the resultant bis[tri(ortho-tolyl)phosphine] palladium salt with an alcoholic alkali. This complex is useful as a catalyst for the production of 1,3-diene oligomers.Type: GrantFiled: July 12, 1979Date of Patent: July 7, 1981Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
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Patent number: 4261901Abstract: Tetrahydrofuran is prepared by reacting propylene and aqueous formaldehyde stabilized with alcohol in the presence of silica sand to form 3-buten-1-ol and chlorinating the 3-buten-1-ol in the presence of Group IA or IIA chloride to form 3,4-dichlorobutan-1-ol which is then treated with a Group IA or IIA base to form 3-chlorotetrahydrofuran which is then hydrogenated to form tetrahydrofuran.Type: GrantFiled: September 10, 1979Date of Patent: April 14, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Edward N. Squire
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Patent number: 4219682Abstract: The yield of alkenols and cycloalkenols is substantially improved by carrying out the reaction of olefins with formaldehyde in the presence of selected catalysts. In accordance with one embodiment, alk-3-en-1-ols are produced in good yields from isobutylene and formaldehyde in the presence of compounds of the metals of Groups VB, VIIB, and VIII.Type: GrantFiled: March 29, 1977Date of Patent: August 26, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4126751Abstract: The yield of alkenols and cycloalkenols is substantially improved by carrying out the reaction of olefins with formaldehyde in the presence of selected catalysts. In accordance with one embodiment, alk-3-en-1-ols are produced in good yields from isobutylene and formaldehyde in the presence of oxides of Group VIB metals.Type: GrantFiled: March 29, 1977Date of Patent: November 21, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4126756Abstract: The yield of alkenols and cycloalkenols is substantially improved by carrying out the reaction of olefins with formaldehyde in the presence of selected catalysts. In accordance with one embodiment, alk-3-en-1-ols are produced in good yields from isobutylene and formaldehyde in the presence of organic carboxylic acid salts of Group IB metals.Type: GrantFiled: March 29, 1977Date of Patent: November 21, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4110403Abstract: A process for preparing .beta.,.gamma.-unsaturated aldehydes which comprises dehydrogenating .beta.,.gamma.-unsaturated alcohols in the vapor phase, preferably in the substantial absence of oxygen, using copper having a specific surface area of 0.01 to 1.5 m.sup.2 /g as a catalyst at a temperature of 150.degree. to 300.degree. C. The .beta.,.gamma.-unsaturated aldehydes can be recovered in pure form by distilling the dehydrogenation reaction mixture in the presence of water. The starting .beta.,.gamma.-unsaturated alcohols can be prepared by reacting olefins with formaldehyde or a derivative capable of forming formaldehyde at a temperature of 180.degree. to 400.degree. C. in the absence of a solvent or in the presence of a non-aqueous organic solvent after pre-heating said formaldehyde or derivative to a temperature of 85.degree. to 150.degree. C.Type: GrantFiled: April 21, 1975Date of Patent: August 29, 1978Assignee: Teijin LimitedInventors: Yataro Ichikawa, Osamu Kobayashi, Kazuhiko Soma, Tatuyuki Naruchi, Yoshiyuki Yamanaka, Nobuo Suzuki
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Patent number: 4104202Abstract: The invention relates to the preparation of perfume compositions. More specifically the invention relates to the use of new 1,5-alkadien-4-ols and esters derived therefrom as components of such compositions.Type: GrantFiled: March 11, 1977Date of Patent: August 1, 1978Assignee: Naarden International N.V.Inventor: Hans J. Wille
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Patent number: 4097540Abstract: A process for the preparation of a dihydric alcohol with the formula ##STR1## wherein R represents an alkyl radical of 1 to 20 carbon atoms which comprises contacting a 2-alkylacrylaldehyde of the formula ##STR2## wherein R has the meaning given above with formaldehyde and thereafter contacting the resultant reaction mixture with hydrogen in the presence of a hydrogenation catalyst.Type: GrantFiled: August 8, 1977Date of Patent: June 27, 1978Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel