By Reaction Of Aldehyde With Olefin (i.e.,by Prins Reaction) Patents (Class 568/879)
  • Patent number: 11976030
    Abstract: 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: Grant
    Filed: September 13, 2019
    Date of Patent: May 7, 2024
    Assignee: BASF SE
    Inventors: Andreas Keller, Roland Minges, Martin Kamasz, Gabriele Gralla, Bernhard Brunner
  • Patent number: 10766840
    Abstract: 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: Grant
    Filed: February 27, 2018
    Date of Patent: September 8, 2020
    Assignee: BASF SE
    Inventors: Andrei-Nicolae Parvulescu, Miriam Bru Roig, Albert Werner, Bernhard Brunner, Wolfgang Siegel, Stephan Maurer, Ulrich Mueller, Michael Ludwig Lejkowski
  • Patent number: 10106484
    Abstract: 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: Grant
    Filed: February 6, 2013
    Date of Patent: October 23, 2018
    Assignee: The Procter & Gamble Company
    Inventors: Juan Estaban Velasquez, Janette Villalobos Lingoes, Jane Ellen Godlewski, Dimitris Ioannis Collias, Fred C. Wireko, Marc Andrew Mamak, Nancy Lee Redman-Furey
  • Publication number: 20130261347
    Abstract: 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: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventors: Mark Scates, Heiko Weiner, Zhenhua Zhou, James Zink
  • Publication number: 20120083630
    Abstract: 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: Application
    Filed: October 4, 2011
    Publication date: April 5, 2012
    Applicant: BASF SE
    Inventors: CHRISTOPH STOCK, Dirk Gerhard, Klaus Ebel
  • Publication number: 20030109757
    Abstract: 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: Application
    Filed: November 8, 2002
    Publication date: June 12, 2003
    Inventors: Hideki Omori, Goro Sawada, Hideo Fukuda, Tomohiko Sato, Mitsuru Takeuchi
  • Patent number: 6316680
    Abstract: 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: Grant
    Filed: December 6, 1999
    Date of Patent: November 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Ralf-Thomas Rahn, Harald Rust, Thomas Rühl, Jochem Henkelmann, Susanne Stutz
  • Patent number: 5523495
    Abstract: 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: Grant
    Filed: February 13, 1995
    Date of Patent: June 4, 1996
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
  • Patent number: 5175371
    Abstract: 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: Grant
    Filed: March 16, 1992
    Date of Patent: December 29, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5175378
    Abstract: 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: Grant
    Filed: March 16, 1992
    Date of Patent: December 29, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4599453
    Abstract: 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: Grant
    Filed: February 25, 1985
    Date of Patent: July 8, 1986
    Assignee: Consiglio Nazionale Delle Ricerche
    Inventors: Carlo Fragale, Michele Gargano, Michele Rossi
  • Patent number: 4571408
    Abstract: 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: Grant
    Filed: October 20, 1983
    Date of Patent: February 18, 1986
    Assignee: Eisai Co., Ltd.
    Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Hideaki Watanabe, Toshiji Igarashi, Hiroyuki Shiojiri, Yoshio Tanabe, Kuniko Hara
  • Patent number: 4503259
    Abstract: 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: Grant
    Filed: May 24, 1983
    Date of Patent: March 5, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
  • Patent number: 4495359
    Abstract: 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: Grant
    Filed: May 5, 1983
    Date of Patent: January 22, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Richard M. Boden
  • Patent number: 4481217
    Abstract: 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: Grant
    Filed: May 28, 1981
    Date of Patent: November 6, 1984
    Assignee: Eisai Co., Ltd.
    Inventors: Isao Yamatsu, Yuichi Inai, Shinya Abe, Hideaki Watanabe, Toshiji Igarashi, Hiroyuki Shiojiri, Yoshio Tanabe, Kuniko Hara
  • Patent number: 4288374
    Abstract: 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: Grant
    Filed: July 28, 1980
    Date of Patent: September 8, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Edward N. Squire
  • Patent number: 4277633
    Abstract: 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: Grant
    Filed: July 12, 1979
    Date of Patent: July 7, 1981
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
  • Patent number: 4261901
    Abstract: 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: Grant
    Filed: September 10, 1979
    Date of Patent: April 14, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Edward N. Squire
  • Patent number: 4219682
    Abstract: 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: Grant
    Filed: March 29, 1977
    Date of Patent: August 26, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4126756
    Abstract: 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: Grant
    Filed: March 29, 1977
    Date of Patent: November 21, 1978
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4126751
    Abstract: 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: Grant
    Filed: March 29, 1977
    Date of Patent: November 21, 1978
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4110403
    Abstract: 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: Grant
    Filed: April 21, 1975
    Date of Patent: August 29, 1978
    Assignee: Teijin Limited
    Inventors: Yataro Ichikawa, Osamu Kobayashi, Kazuhiko Soma, Tatuyuki Naruchi, Yoshiyuki Yamanaka, Nobuo Suzuki
  • Patent number: 4104202
    Abstract: 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: Grant
    Filed: March 11, 1977
    Date of Patent: August 1, 1978
    Assignee: Naarden International N.V.
    Inventor: Hans J. Wille
  • Patent number: 4097540
    Abstract: 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: Grant
    Filed: August 8, 1977
    Date of Patent: June 27, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel