Methylol Cyclohexane (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/831)
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Patent number: 5395990Abstract: 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: GrantFiled: December 30, 1993Date of Patent: March 7, 1995Assignee: Eastman Chemical CompanyInventor: John Scarlett
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Patent number: 5387753Abstract: 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: GrantFiled: December 30, 1993Date of Patent: February 7, 1995Assignee: Eastman Chemical CompanyInventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
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Patent number: 5387752Abstract: 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: GrantFiled: December 30, 1993Date of Patent: February 7, 1995Assignee: Eastman Chemical CompanyInventors: John Scarlett, Michael A. Wood, Colin Rathmell
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Patent number: 5342903Abstract: A process for the preparation of adducts by reacting an alcohol with an epoxy compound in the presence of a catalyst, which comprises reacting an alcohol of formula I ##STR1## wherein A is an aliphatic, cycloaliphatic or araliphatic radical and r is a number from 1 to 10, with a mono- or diepoxide in the equivalent ratio of 1:20 to 20:1, based on the hydroxyl and epoxy groups, in the presence of a metal complex of formula II as catalyst[M.sup.n+ (L.sub.1).sub.x (L.sub.2).sub.y (L.sub.3.sup.m-).sub.z ][X.sup.k- ].sub.(n-zm)/k (II),whereinM is a metal of the main groups or subgroups of the Periodic Table of the Elements,L.sub.1 and L.sub.2 are weakly bonded, neutral, unidentale or multidentate ligands,L.sub.3 is a strongly bonded, non-replaceable neutral or anionic unidentale or multidentate ligand,X is an anion of the following formulae BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, ClO.sub.4.sup.-, IO.sub.4.sup.-, NO.sub.3.sup.Type: GrantFiled: April 30, 1993Date of Patent: August 30, 1994Assignee: Ciba-Geigy CorporationInventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
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Patent number: 5334779Abstract: 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: GrantFiled: June 1, 1993Date of Patent: August 2, 1994Assignee: Eastman Kodak CompanyInventor: Yeong-Jen Kuo
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Patent number: 5286878Abstract: A process is provided whereby organic carbonyl substrates, including esters, ketones and amides, are reduced in a reaction with a silane reducing reagent and a catalyst. Effective catalysts broadly include those which consist of a group 4, 5 or 6 metal which either: a) is in less than its maximum oxidation state or is capable of being converted to a complex in less than its maximum oxidation state; and/or is a group 4, 5 or 6 metal hydride. Exemplary catalysts include titanium-containing catalysts such as (bis trimethylphosphine) titanocene, trimethyl phosphine adduct of a (hydrido) silyl complex of titanocene, titanocene dichloride and titanocene monochloride.Type: GrantFiled: November 21, 1990Date of Patent: February 15, 1994Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Kristina A. Kreutzer, Esther Spaltenstein
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Patent number: 5250713Abstract: A process for producing desulfurized fats and oils or fatty acid esters is disclosed, which comprises treating fats and oils or fatty acid esters under hydrogen or a mixture of hydrogen and an inert gas atmosphere at a pressure of from 0.1 to 500 kg/cm.sup.2 in the absolute pressure at a temperature of from 100.degree. to 350.degree. C. in the presence of a catalyst of the following formula (I):Cu.multidot.X.sub.x .multidot.Y.sub.y .multidot.O.sub.z (I)wherein all symbols are defined in the disclosure. A process for producing an alcohols using desulfurized fats and oils or fatty acid esters is also disclosed. According to the process for producing an alcohol of the present invention, an alcohol of a high purity and good qualities can efficiently and effectively be produced.Type: GrantFiled: March 11, 1992Date of Patent: October 5, 1993Assignee: Kao CorporationInventors: Hiroyuki Tamura, Yasuyuki Hattori, Kunizo Hashiba, Osamu Tabata, Kiyoshi Tsukada, Noriaki Fukuoka
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Patent number: 5223633Abstract: A process for the preparation of a compound of the formula ##STR1## which comprises deprotonating a carbamate of the formula ##STR2## in an inert solvent with a selective base, in the presence of a chelate-forming diamine to give a compound of the formula ##STR3## and then reacting III in an inert solvent, either with an achiral electrophile of the formula (IV) or (V) or with an optionally prochiral electrophile of the formula (VI) ##STR4## and in the case in which R.sup.1 represents an electrofugic leaving group, optionally again electrophilically substituted with the formation of an acyl anion and renewed deprotonation, and in a last step, solvolytically removing the protecting group --CO--NR.sup.10 R.sup.11.Type: GrantFiled: February 19, 1992Date of Patent: June 29, 1993Assignee: Bayer AktiengesellschaftInventors: Dieter Hoppe, Petra Tebben, Folker Hintze, Thomas Raffel
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Patent number: 5191091Abstract: A process for hydrogenating bound oxygen-containing organic feeds into their corresponding alcohols by contact with a coprecipitated copper-aluminum catalyst that has been activated by contact with reducing gas at a temperature that gradually increases.Type: GrantFiled: January 27, 1992Date of Patent: March 2, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard W. Wegman, David R. Bryant
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Patent number: 5185476Abstract: Disclosed are novel catalysts useful for the hydrogenation of carbonyl-containing compounds at mild conditions of temperature and pressure to produce alcohols or amines is disclosed. The catalysts comprise palladium and zinc on a catalyst support material and are obtained by the steps of:(a) providing a catalyst support material on which is deposited zero-valent palladium in a uniformly and highly dispersed form;(b) contacting the palladium-bearing support material of (a) with zinc or a reducible compound thereof; and, preferably,(c) heating the palladium- and zinc-bearing support of (b) at a temperature of about 200.degree. to 400.degree. C. in the presence of an oxygen-containing gas.Type: GrantFiled: September 26, 1991Date of Patent: February 9, 1993Assignee: Eastman Kodak CompanyInventor: Bruce L. Gustafson
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Patent number: 5142067Abstract: A process for hydrogenating feeds into their corresponding alcohols by contact with a coprecipitated catalyst comprising copper, aluminum, and a metal (X) selected from the group consisting of magnesium, zinc, titanium, zirconium, tin, nickel, cobalt and mixtures thereof; that has been reduced with an increasing temperature during the reduction.Type: GrantFiled: November 5, 1991Date of Patent: August 25, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard W. Wegman, David R. Bryant
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Patent number: 5053562Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium, a phosphine, and a lower-alkyl iodide or .beta.-hydroxy lower-alkyl iodide.Type: GrantFiled: July 31, 1990Date of Patent: October 1, 1991Assignee: Hoechst Celanese CorporationInventor: Kwoliang D. Tau
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Patent number: 5019658Abstract: The instant invention is an improvement in the method of producing optically pure sterioisomers from a racemic mixture. The method is based on the well-known fact that a supersaturated solution or melt of the racemic mixture can be seeded with just the crystals of the desired stereoisomer, which will then crystallize out selectively, leaving the undesired stereoisomer behind in the liquid mother liquor. The desired isomer, in crystaline form, can then be separated by simple liquid/solid separation from the undesired isomer remaining behind in the mother liquor. In the conventional method, supersaturation is achieved by careful cooling of a saturated solution or melt. In the present invention, supersaturation is achieved by increasing the ambient pressure over the saturated solution or melt of the racemic mixture, and relying on the fact that the melting temperature of a substance increases with increasing pressure, provided there is an increase in molar volume when the substance melts.Type: GrantFiled: October 23, 1989Date of Patent: May 28, 1991Assignee: Kobe Steel LimitedInventor: Robert P. Cahn
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Patent number: 4999090Abstract: A process of preparing industrially trans-1,4-cyclohexanedimethanol of high purity by distilling a mixture of cis- and trans-1,4-cyclohexanedimethanol in the presence of alkali, or by heating a mixture of cis- and trans-1,4-cyclohexanedimethanol in the presence of alkali and then distilling the heated mixture, and a process of preparing powdered trans-1,4-cyclohexanedimethanol by pulverizing the distillate obtained above.Type: GrantFiled: July 5, 1989Date of Patent: March 12, 1991Assignee: Towa Chemical Industry Co., Ltd.Inventors: Yoshiaki Tateno, Susumu Yoneda, Naoki Okamoto, Yoshibumi Ishii, Kazuaki Kato
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Patent number: 4918248Abstract: An alcohol is effective produced by catalytically reducing an organic carboxylic acid ester with hydrogen in the presence of a catalyst obtained by reducing a catalyst precursor comprising (A) copper oxide and (B) titanium oxide and/or titanium hydroxide at a weight ratio of (A) to (B) in the range between 15/85 and 65/35. The component (A) may be alternatively a composite metal oxide comprises copper oxide and up to 20 wt. % of zinc oxide.Type: GrantFiled: May 22, 1989Date of Patent: April 17, 1990Assignee: Kao CorporationInventors: Yasuyuki Hattori, Noriaki Fukuoka, Shigeru Tamura, Kunizo Hashiba, Kiyoshi Tsukada, Makoto Misono
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Patent number: 4880937Abstract: An alcohol compound is produced by reducing a carboxylic acid or an ester thereof with an alcohol in the presence of a solid catalyst. The catalyst includes a hydrous metal oxide belonging to Group IV of the Periodic Table.Type: GrantFiled: February 18, 1988Date of Patent: November 14, 1989Assignee: Japan Tobacco, Inc.Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
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Patent number: 4847425Abstract: 4-isopropylcyclohexylmethanol and its alkyl ethers of the general formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, are prepared by a process in which the novel 4-(1-alkoxy-1-methylethyl)-benzaldehyde or its dialkyl acetal of the general formula II ##STR2## where X is oxygen (IIa) or its two R.sup.2 O groups (IIb) and R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.4 -alkyl, is heated to 100.degree.-250.degree. C., preferably 130.degree.-200.degree. C., under a hydrogen pressure of from 50 to 350, preferably from 150 to 300, bar in the presence of a noble metal of group VIII of the Periodic Table.Type: GrantFiled: May 31, 1988Date of Patent: July 11, 1989Assignee: BASF AktiengesellschaftInventors: Dieter Degner, Walter Gramlich, Wolfgang Lengsfeld, Ludwig Schuster
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Patent number: 4837367Abstract: Process for the hydrogenation of carbonyl-containing compounds at mild conditions of temperature and pressure to produce alcohols or amines is disclosed, employing palladium on zinc oxide catalysts. A method for the preparation of the palladium on zinc oxide catalysts useful for the desired reductive conversion is also disclosed.Type: GrantFiled: August 3, 1987Date of Patent: June 6, 1989Assignee: Eastman Kodak CompanyInventors: Bruce L. Gustafson, Paul S. Wehner, Gregory O. Nelson, Patricia N. Mercer
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Patent number: 4792618Abstract: Fluoro-substituted carbocyclic compounds are prepared by(A) reacting hydrogen fluoride with a chloro-cyclohexenyl compound of the formula ##STR1## where R.sub.1 and R.sub.2 are independently selected from the group consisting of --H, --CH.sub.2 OH, --COF, --COCl, --CF.sub.3, --CN, ##STR2## and --CH.sub.2 R, where R is --H or alkyl of 1-4 carbon atoms, to form a gem-dihalocyclohexane compound of the formula ##STR3## where X is chlorine and R.sub.1 and R.sub.Type: GrantFiled: December 12, 1984Date of Patent: December 20, 1988Assignee: Occidental Chemical CorporationInventors: Joseph F. Bieron, David Y. Tang
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Patent number: 4774225Abstract: The invention relates to novel odorant substances. These are compounds of the formula ##STR1## wherein R and R.sup.1 are H, CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7 or CH(CH.sub.3).sub.2 and the sum of the carbon atoms in R and R.sup.1 does not exceed 6, and X is caran-yliden (2,2) or caran-yliden (4,4).The invention relates also to the preparation of these novel substances and to odorant compositions containing these substances.Type: GrantFiled: October 30, 1987Date of Patent: September 27, 1988Assignee: Societe Anonyme Roure Bertrand DupontInventor: Edouard Giraudi
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Patent number: 4739103Abstract: Di- and tri-substituted perfluorocycloalkane compounds which have a cyclohexane or decahydronaphthalene nucleus are provided. These perfluorocycloalkane compounds are carbonyl fluorides and derivatives thereof.Type: GrantFiled: February 1, 1985Date of Patent: April 19, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: John C. Hansen, Patricia M. Savu
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Patent number: 4695660Abstract: 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: GrantFiled: July 24, 1986Date of Patent: September 22, 1987Assignee: Huls AktiengesellschaftInventors: Werner Otte, Rudolf Nehring
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Patent number: 4480115Abstract: This invention provides an improved process for direct hydrogenation of a carboxylic acid to its corresponding alcohol with synthesis gas in the presence of a homogeneous catalyst comprising a ruthenium compound and a Lewis Acid metal halide.Type: GrantFiled: March 17, 1983Date of Patent: October 30, 1984Assignee: Celanese CorporationInventor: James L. McGinnis
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Patent number: 4459419Abstract: Zeolite-ruthenium catalysts in which the ruthenium is in the form of a cation are very effective in catalyzing the hydrogenation of a broad range of organic compounds.Type: GrantFiled: September 2, 1982Date of Patent: July 10, 1984Assignee: Ethyl CorporationInventor: Paul D. Seemuth
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Patent number: 4438287Abstract: Alcohols may be prepared in a combination process by subjecting an aliphatic paraffinic hydrocarbon feed stream to a dehydrogenation reaction and thereafter subjecting the reaction product mix comprising a mixture of aliphatic paraffinic hydrocarbons and aliphatic olefinic hydrocarbons, without separating the olefins in the product mix from the paraffins, to a hydroformylation reaction. The hydroformylation reaction is effected by treating said product mix with carbon monoxide and hydrogen in the presence of a catalyst comprising a rhodium-containing compound and a promoter comprising a trialkyl-substituted monoamine, all three of said alkyl moieties being substituted to the nitrogen of said amine to selectively prepare the desired alcohols.Type: GrantFiled: August 25, 1982Date of Patent: March 20, 1984Assignee: UOP Inc.Inventor: Tamotsu Imai
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Patent number: 4393251Abstract: Hydrogenation catalysts which are prepared from mixed crystals of copper-zinc compounds, obtained by precipitation, of the formulaCu.sub.1.5-3 Zn.sub.1-2.5 (CO.sub.3).sub.1-2 (OH).sub.4-6.(H.sub.2 O).sub.0-1by decomposition at 200.degree.-500.degree. C., and are used for the catalytic preparation of propanediols of the formula ##STR1## where the R's may be identical or different and each is an aliphatic, araliphatic or aromatic radical, or the two R's together with the adjacent carbon atom are members of an alicyclic ring, by hydrogenating hydroxypropionaldehydes of the formula ##STR2## where R has the above meanings, and to processes for the preparation of propanediols, using such catalysts. The propane-1,3-diols obtainable by the novel process are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example of polyesters derived from the propanediols.Type: GrantFiled: February 10, 1982Date of Patent: July 12, 1983Assignee: BASF AktiengesellschaftInventors: Franz J. Broecker, Leopold Hupfer, Franz Merger, Ernest Miesen, Juergen Paetsch, Guenter Zirker
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Patent number: 4386219Abstract: Hydrogenation catalysts, which have a specific surface area of from 50 to 150 square meters per gram, solely or partially contain crystals having a spinel structure and copper in the form of copper oxide, and have been obtained by precipitating copper and aluminum in a ratio of from 0.25 to 3 atoms of copper per atom of aluminum from their compounds in the presence of a carbonate at a pH of from 4.5 to 9 and calcining the resulting precipitate at from 300.degree. to 800.degree. C., for the catalytic preparation of propanediols by hydrogenating hydroxypropionaldehydes at not more than 300 bar pressure and from 50.degree. to 200.degree. C., and processes for the preparation of propanediols by the use of such catalysts.The propanediols obtainable by the process of the invention, in particular 2,2-dimethylpropane-1,3-diol, are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example corresponding polyesters.Type: GrantFiled: February 2, 1982Date of Patent: May 31, 1983Assignee: BASF AktiengesellschaftInventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
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Patent number: 4348543Abstract: The present invention describes cycloaliphatic alcohols prepared via a Diels-Alder reaction.Type: GrantFiled: February 12, 1981Date of Patent: September 7, 1982Assignee: Henkel CorporationInventor: Edgar R. Rogier
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Patent number: 4317918Abstract: An alcohol is produced in a high selectivity with a good yield from the corresponding carboxylic acid by reducing the latter with hydrogen in the presence of a rhenium catalyst in the coexistence of an organic base. An arylacetic acid, which is included in the starting carboxylic acid, can be produced in an excellent yield from the corresponding aryl aldehyde by reacting the latter with carbon monoxide and water in the presence of rhodium or its compound and hydrogen iodide.Type: GrantFiled: November 3, 1980Date of Patent: March 2, 1982Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tetsuo Takano, Gohu Suzukamo, Masaru Ishino, Kiyoshi Ikimi
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Patent number: 4301022Abstract: Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic, nonionic and zwitterionic detergent comprising the step of adding to a solid or liquid cationic, nonionic or zwitterionic detergent base an aroma augmenting or enhancing quantity of at least one compound defined according to the structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and R is hydrogen or acetyl.Type: GrantFiled: October 9, 1980Date of Patent: November 17, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4273947Abstract: A process is described for the heterogeneous hydrogenation of fluorine-containing alkyl, cycloalkyl, and benzene carboxylic acids to the corresponding primary alcohols. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture thereof. In the liquid phase, the hydrogenation can be carried out batchwise under mild conditions of temperature and pressure, preferably at about 50.degree.-150.degree. C. and about 5-15 atmospheres, in an atmosphere containing hydrogen gas. A preferred embodiment is the hydrogenation of trifluoroacetic acid in the liquid phase to 2,2,2-trifluoroethanol, said alcohol being useful as an intermediate in the synthesis of the anesthetic, isoflurane, CF.sub.3 CHClOCHF.sub.2.Type: GrantFiled: January 31, 1979Date of Patent: June 16, 1981Assignee: Allied Chemical CorporationInventor: Miroslav Novotny
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Patent number: 4263449Abstract: An alcohol is produced from a compound having an alkenyl group by a hydroformylation of said compound having an alkenyl group in a substantially water immiscible solvent in the presence of a hydroformylation catalyst which is soluble in said solvent and a hydrogenation of the reaction mixture in the presence of a hydrogenation catalyst.Water is added at a ratio of 0.5 to 30 times by weight base on an aldehyde produced by said hydroformylation before said hydrogenation, and an organic phase containing the hydroformylation catalyst component is separated from a water phase containing the alcohol produced by said hydrogenation and said organic phase is recycled into said hydroformylation.The compound having an alkenyl group is an aliphatic olefin, a hydroxyolefin, and olefin ether or an olefin ester and the corresponding saturated alcohol having one more carbon atom is produced.Type: GrantFiled: March 24, 1980Date of Patent: April 21, 1981Assignee: Toyoda Soda Manufacturing Co., Ltd.Inventors: Toshihiro Saito, Yukihiro Tsutsumi, Shoji Arai
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Patent number: 4197414Abstract: Olefins are converted to alcohols by a one-step, hydroformylation process comprising contacting an olefin, such as 1-hexene, with a gaseous mixture of carbon monoxide and hydrogen in the presence of a catalyst prepared by loading a bimetallic cluster of the formula: Rh.sub.x Co.sub.y CO.sub.12 wherein both x and y are independently integers 1-3 with the proviso that .SIGMA.(x+y)=4, onto an amine resin, such as Dowex.RTM. MWA-1.Type: GrantFiled: October 18, 1978Date of Patent: April 8, 1980Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Philip E. Garrou
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Patent number: 4181810Abstract: A process for the preparation of a propane-1,3-diol, disubstituted in the 2-position, which comprises contacting an ethanal disubstituted in the 2-position, which ethanal has the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and denote optionally substituted alkyl, cycloalkyl, aralkyl or aryl radicals or an optionally substituted heterocyclic radical, or together denote an optionally substituted divalent hydrocarbon radical with formaldehyde in the presence of an acid ion exchanger and thereafter contacting the resultant reaction product with hydrogen under hydrogenation conditions.Type: GrantFiled: November 16, 1977Date of Patent: January 1, 1980Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel