Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/830)
  • Patent number: 5406004
    Abstract: A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) supplying to the hydrogenation zone a vaporous feed stream containing hydrogen and a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof, at an inlet temperature which is above the dew point of the mixture;(c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of esters;(d) recovering from the hydrogenation zone a two phase product stream containing a hydroxylic compou
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: April 11, 1995
    Assignee: Eastman Chemical Company
    Inventors: Philip H. D. Eastland, John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5395991
    Abstract: A hydrogenation process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding unsaturated organic compound selected from esters, diesters and lactones which involves use of two hydrogenation zones (11, 36), each containing a charge of a hydrogenation catalyst (12, 37). In a first phase of operation one of the hydrogenation zones (36 or 11) is in standby condition and a stream of hot hydrogen-containing gas is passed therethrough. Meanwhile a vaporous feed stream comprising a hydrogen-containing gas and the unsaturated organic compound to be hydrogenated, e.g. dimethyl 1,4-cyclohexanedicarboxylate, is fed to the active zone (11 or 36). This feed stream can include the gas stream from the first mentioned hydrogenation zone (36 or 11).
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5395986
    Abstract: A process is described for the production of cyclohexanedimethanol having a trans-:cis-isomer ratio greater than about 1:1 by hydrogenation of a dialkyl (e.g. dimethyl) cyclohexanedicarboxylate having a trans-:cis-isomer ratio less than about 1:1 which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) supplying to the hydrogenation zone a vaporous feed stream containing hydrogen and a hydrogenarable material comprising a dialkyl cyclohexanedicarboxylate at an inlet temperature which is above its dew point of the mixture;(c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of esters;(d) passing the vaporous feed stream through the hydrogenation zone; and(e) recovering from the hydrogenation zone a product stream containing cyclohexanedimethanol having a trans-:cis-isomer ratio greater than 1:1.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael A. Wood
  • Patent number: 5395990
    Abstract: A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, aldehydes, olefinically unsaturated aldehydes, and mixtures of two or more thereof, which process comprises the steps of:(a) providing a hydrogenation zone containing a charge of a granular hydrogenation catalyst which has a total surface area of at least about 15 m.sup.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventor: John Scarlett
  • Patent number: 5395987
    Abstract: A continuous process is described for the production of 1,4-cyclohexanedimethanol (CHDM) having a desired or predetermined trans-:cis- isomer ratio by catalytic hydrogenation of a dialkyl 1,4-cyclohexanedicarboxylate in the presence of an ester hydrogenation catalyst. The process is capable of being operated for an extended period of time during which the hydrogenation catalyst declines in catalytic activity and comprises feeding a vaporous mixture of the dialkyl 1,4-cyclohexanedicarboxylate and hydrogen to a hydrogenation zone containing the hydrogenation catalyst and recovering CHDM product. The degree of conversion of the dialkyl 1,4-cyclohexanedicarboxylate at a particular combination of temperature and pressure is related to the trans-:cis- isomer ratio of the CHDM product and may be varied by adjusting at least one feed condition selected from (i) the dialkyl 1,4-cyclohexanedicarboxylate feed rate and (ii) the hydrogen-containing gas:dialkyl 1,4-cyclohexanedicarboxylate molar ratio.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: Colin Rathmell, Richard C. Spratt, Michael W. M. Tuck
  • Patent number: 5387753
    Abstract: A process is described for reactivating an at least partially deactivated copper-containing ester hydrogenation catalyst which has undergone deactivation through use in hydrogenation of an unsaturated organic compound selected from esters of C.sub.8 to C.sub.22 monocarboxylic acids, diesters of dicarboxylic acids, and lactones, to yield a corresponding hydroxylic compound selected from alcohols and diols which comprises contacting the at least partially deactivated copper-containing catalyst at an effective reactivation temperature and for an effective period of time with a stream of hydrogen-containing gas which is substantially free from the unsaturated organic compound thereby to reactivate the at least partially deactivated copper-containing catalyst.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: February 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5387752
    Abstract: A process is described for the production of cyclohexanedimethanol by hydrogenation of a dialkyl cyclohexanedicarboxylate which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) forming a vaporous feed stream of a hydrogen-containing gas,and a hydrogenatable material comprising a dialkyl cyclohexanedicarboxylate at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure in the range of from about 150 psia (about 10.34 bar) to about 2000 psia (about 137.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: February 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael A. Wood, Colin Rathmell
  • Patent number: 5334779
    Abstract: Disclosed are catalyst compositions comprised of the oxides of copper, zinc, and a third element selected from the group consisting of aluminum, magnesium, zirconium, and mixtures thereof, and the use of such catalyst compositions in the hydrogenation of carbonyl compounds such as carboxylate esters to obtain the alcohol corresponding to the acid residue of the ester.
    Type: Grant
    Filed: June 1, 1993
    Date of Patent: August 2, 1994
    Assignee: Eastman Kodak Company
    Inventor: Yeong-Jen Kuo
  • Patent number: 5300706
    Abstract: A process for the preparation of d,l-menthol by catalytic hydrogenation of aromatic or partly hydrogenated cyclic compounds which have the carbon skeleton of menthol having at least one double bond and are substituted by oxygen in the 3-position relative to the methyl group, with simultaneous rearrangement of optically active or inactive stereoisomers of menthol at elevated temperature and under pressure is described. The hydrogenation, which is to be carried out continuously, is carried out on a fixed bed catalyst which comprises, as active constituents, palladium, ruthenium or rhodium or a mixture of these elements, and comprises alkali metal hydroxides and/or alkali metal sulphates as promoters; the support for this catalyst is doped with a rare earth metal and manganese.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: April 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Gerhard Darsow, Hans-Josef Buysch
  • Patent number: 5030771
    Abstract: A method of producing aliphatic and cycloaliphatic diols by catalytic hydrogenation of dicarboxylic acid esters by the use of a copper chromite catalyst in which the copper content (calculated as CuO) is 40-47 wt. %, and the chromium content (calculated as Cr.sub.2 O.sub.3) is 40-47 wt. %, and barium is also present in the amount of up to 10 wt. % (calculated as BaO) under mild temperature and pressure conditions is disclosed. The method produces diols without the formation of high boiling materials and does not require purification of the product diols by overhead distillation.
    Type: Grant
    Filed: December 20, 1989
    Date of Patent: July 9, 1991
    Assignee: Huels Aktiengesellschaft
    Inventors: Werner Fuhrmann, Gunther Bub, Manfred zur Hausen
  • Patent number: 5015787
    Abstract: In a process for production of cyclohexanol comprising the selective catalytic hydrogenation of phenol to a product mixture comprising a major portion of cyclohexanol and a substantially smaller portion of cyclohexanone, then distillation of said product mixture to obtain cyclohexanol containing a minor amount of cyclohexanone meeting desired specification levels; the improvement comprising adding to said product mixture an effective amount of a polyamine such as hexamethylene diamine and distilling the product mixture to obtain an improved yield of said cyclohexanol containing a minor amount of cyclohexanone.
    Type: Grant
    Filed: April 10, 1989
    Date of Patent: May 14, 1991
    Assignee: Allied-Signal Inc.
    Inventor: Jan F. Van Peppen
  • Patent number: 4877909
    Abstract: A process for reducing an aldehyde or ketone in the presence of a stable, highly active catalyst which is insoluble in a solvent and which can be recovered easily from the reaction system after completion of the reaction and used repeatedly, characterized in that an aldehyde or ketone having a carbonyl group is reacted with an alcohol in the presence of hydrous zirconium oxide as the catalyst.
    Type: Grant
    Filed: February 22, 1988
    Date of Patent: October 31, 1989
    Assignee: Japan Tobacco, Inc.
    Inventors: Sigenobu Mizusaki, Hajime Matsushita, Shigeo Ishiguro, Hiroshi Ichinose, Akira Izumi
  • Patent number: 4835278
    Abstract: A process is described for the preparation of a compound of formula (2) ##STR1## (wherein R is a C.sub.1-6 alkyl or a C.sub.7-20 aralkyl group) and the salts thereof, which comprises reducing a compound of formula (3) ##STR2## (or a salt thereof), using a reducing system comprising borohydride ions and metal ions selected from lanthanide ions, alkaline earth metal ions or yttrium ions in solution. The reduction system may be provided by a borohydride (e.g. NaBH.sub.4) and a metal salt (e.g. CeCl.sub.3).The ester (2) may then if desired be hydrolyzed to give the parent acid.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: May 30, 1989
    Assignee: Glaxo Group Limited
    Inventors: Roger Barrett, Clive A. Meerholz, Brian D. Judkins
  • Patent number: 4745234
    Abstract: The invention relates to a process for the preparation of .alpha.-.beta. unsaturated alcohols of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3, which may be equal or different, represent phenyl, optionally substituted with one or more alkyl and/or alkoxy groups, the total number of C atoms of these substituents being at most 5, or hydrogen or an alkyl group with 1-10 C atoms, with at least one of the groups R.sub.1, R.sub.2 and R.sub.3 representing the optionally substituted phenyl group, by hydrogenation in the liquid phase of the aldehyde corresponding with the desired alcohol, this being effected in the presence of a platinum-containing catalyst and of an alkali metal hydroxide and/or an alkali metal alkoxide as promotor, wherein platinum-on-graphite is used as catalyst.
    Type: Grant
    Filed: August 19, 1987
    Date of Patent: May 17, 1988
    Assignee: Stamicarbon B.V.
    Inventors: Cornelis G. M. van de Moesdijk, Marcel A. R. Bosma
  • Patent number: 4723046
    Abstract: A process for preparing 4,4'-biphenol comprising subjecting 4,4-bis(4-hydroxyphenyl)cyclohexanol to decomposition and dehydrogenation in the presence of a dehydrogenation catalyst.4,4-Bis(4-hydroxyphenyl)cyclohexanol is a novel compound which can be prepared by reacting 4-hydroxycyclohexanone with phenol.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: February 2, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Teruyuki Nagata, Tohru Miura
  • Patent number: 4695660
    Abstract: A method of producing cyclohexyl compounds by catalytic hydrogenation of benzyl compounds, particularly acetophenone, whereby the benzyl compounds are hydrogenated in the presence of a catalyst comprising Ru and a support, with said benzyl compounds being in a slurry or a trickling liquid phase, at a hydrogen pressure of 200-350 bar, particularly 250-320 bar, and a temperatures of from 80.degree. to about 160.degree. C., particularly 100.degree.-130.degree. C., wherewith the catalyst contains Ru in the amount of, in particular, 0.1-1 wt. %.
    Type: Grant
    Filed: July 24, 1986
    Date of Patent: September 22, 1987
    Assignee: Huls Aktiengesellschaft
    Inventors: Werner Otte, Rudolf Nehring
  • Patent number: 4604488
    Abstract: Fragrant cyclohexanol derivatives are produced by condensing 2-ethylidene-5-norbornene with a phenol compound, in the presence of a Friedel-Crafts catalyst; and hydrogenating the condensation product in the presence of a metal catalyst.The compounds so produced have a green-floral odor and are advantageously used in soaps, detergents, shampoos, hair rinse, cosmetics, colognes and perfumes.
    Type: Grant
    Filed: December 21, 1983
    Date of Patent: August 5, 1986
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Yasushi Kajihara, Naotake Takaishi, Yoshiaki Inamoto, Akio Kimura, Motoki Nakajima, Norioki Miyamoto
  • Patent number: 4551564
    Abstract: 2- and 4-tert-butylcyclohexanols are produced having high proportions of cis-isomers, by hydrogenating the corresponding tert-butylphenols in the presence of Pd and Ru catalysts in two stages under hydrogen pressures of above 200 bar and at temperatures of 70.degree.-280.degree. C. In the first stage, a Pd catalyst is employed, and a Ru catalyst is used in the second stage.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: November 5, 1985
    Assignee: Chemische Werke Huels, AG
    Inventors: Werner Otte, Rudolf Nehring, Manfred zur Hausen
  • Patent number: 4503273
    Abstract: The hydrogenation of phenolic molecules can be more effectively carried out using pretreated Group VIII catalysts.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: March 5, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Edward C. Mozdzen
  • Patent number: 4314942
    Abstract: An improved synthetic process for the removal of an allyl group in an allylic ester or an allyloxycarbonyl group in an allylic carbonate or carbamate by reaction with 2-ethylhexanoic acid or an alkali metal salt thereof and a catalytic amount of an organic-soluble palladium complex is disclosed herein.
    Type: Grant
    Filed: January 10, 1979
    Date of Patent: February 9, 1982
    Assignee: Schering Corporation
    Inventor: Stuart W. McCombie
  • Patent number: 4273933
    Abstract: A modified nickel catalyst used for stereo-differentiating reduction of carbonyl compounds is provided. The modified nickel catalyst is prepared by soaking a nickel catalyst in an aqueous modifying medium having dissolved therein at least one inorganic salt, such as sodium bromide or sodium chloride, and at least one optically active substance, such as optically active hydroxy acid. The modified nickel catalyst exhibits enhanced activity for stereo-differentiating reduction and causes little or no side reactions, and thus, brings about an extremely high yield of the reaction product.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: June 16, 1981
    Assignee: Kawaken Fine Chemicals Co., Ltd.
    Inventors: Tadao Harada, Yoshiharu Izumi, Shinichiro Komatsu