Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/814)
-
Patent number: 5478789Abstract: A hydrogenation reaction catalyst precursor of the present invention comprises a catalyst carrier (A) and a metal oxide composition (B) carried on or mixed with the catalyst carrier (A) at a weight ratio of (B)/(A)=15/85 to 65/35; the catalyst carrier (A) comprising a carrier base material of silica, etc. and a coating of titanium oxide and/or titanium hydroxide, the metal oxide composition (B) comprising copper oxide, zinc oxide, and at least one oxide of a metal selected from the group consisting of an element of group IIa of the periodic table, an element of group IIIb of the table, a lanthanide element, and an actinide element at a weight ratio of 100/(0 to 25)/(0 to 25). A hydrogenation reaction catalyst with a high catalytic activity and a high reaction selectivity is obtained by reduction of the hydrogenation reaction catalyst precursor.Type: GrantFiled: October 4, 1994Date of Patent: December 26, 1995Assignee: Kao CorporationInventors: Yasuyuki Hattori, Kiyoshi Tsukada
-
Patent number: 5420366Abstract: The present invention provides a process for preparing optically active 2-arylcyclohexanol and its esters and ethers and which process comprises the step of subjecting 1-aryl-cyclohexane-1,2 diol and its diethers and diesters to hydrogenolysis conditions to form said cyclohexanol and its esters and ethers.Type: GrantFiled: May 11, 1994Date of Patent: May 30, 1995Assignee: Hoechst Celanese CorporationInventor: Shu-Hai Zhao
-
Patent number: 5395983Abstract: R or S-1-phenyl-1,3-propanediols having optical purity of 100% ee were obtained by recrystallization of R or S-1-phenyl-1,3-propanediols having optical purity of 20% ee to below 100% ee, the last diols are represented by the formula, ##STR1## It is possible to obtain optically pure 1-phenyl-3-propanediols from optically impure 1-phenyl-1,3-propanediols by a simple method.Type: GrantFiled: January 18, 1994Date of Patent: March 7, 1995Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Teruyo Sugiura, Yasuyuki Koizumi, Naoyuki Yoshida
-
Patent number: 5395984Abstract: Described is a process for preparing 2-phenyl-1,3-propanediol by converting the 2-nitro-2-phenyl-1,3-propanediol to a nitro-dioxane of the formula ##STR1## wherein the groups R are both C.sub.1 -C.sub.6 alkyl or together comprise a C.sub.5 -C.sub.6 cycloalkyl group, or wherein one R group is H and the other is phenyl; hydrogenolysis of the nitro-dioxane to give a dioxane of the formula ##STR2## wherein R is as defined above; and hydrolyzing the dioxane to form 2-phenyl-1,3-propanediol.Type: GrantFiled: April 20, 1994Date of Patent: March 7, 1995Assignee: Schering CorporationInventors: Patrick O'Neill, Henry Doran
-
Patent number: 5387726Abstract: A process is disclosed for the selective catalytic hydrogenation of carbonyl groups in aromatic aldehydes of the formula: ##STR1## in which X is carboxyl, methyl or a halogen, to give the corresponding alcohols and methyl compounds. The catalytic hydrogenation is performed with the addition of a solvent optionally in the presence of organic acids on a shaped support catalyst containing a platinum group metal on a support made from titanium oxide in the presence of hydrogen at hydrogen partial pressures of 5 to 50 bar and temperatures of 100.degree. to 300.degree. C.Type: GrantFiled: January 7, 1994Date of Patent: February 7, 1995Assignee: Degussa AktiengesellschaftInventors: Martin Bankmann, Reinhold Brand, Andreas Freund, Thomas Tacke
-
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
-
Patent number: 5372995Abstract: Described is a two-step process for producing phenyl- and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention by means of first reacting methyl ethyl ketone with benzaldehyde in the presence of a sulfonic acid catalyst to produce a mixture of phenyl pentenone derivatives; and then hydrogenating the resulting mixture of phenyl pentenone derivatives in the presence of a hydrogenation catalyst, as well as the product produced thereby; and perfumery uses thereof for augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles.Type: GrantFiled: April 15, 1994Date of Patent: December 13, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna
-
Patent number: 5352845Abstract: A process for manufacturing an optically active saturated compound of the general formula (25): ##STR1## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22, and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, is disclosed.Type: GrantFiled: March 25, 1993Date of Patent: October 4, 1994Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
-
Patent number: 5349095Abstract: A process for preparing a substituted or unsubstituted 3- or 4-hydroxyalkylbenzocyclobutene compound comprises reducing a corresponding 3- or 4-formyl or ketobenzocyclobutene compound with a hydride at a temperature below that at which dimerization or oligomerization of the formyl- or ketobenzocycloutene compound or the thus-produced hydroxyalkylbenzocyclobutene compound is a significant side reaction, for a time sufficient to convert the formyl- or ketobenzocyclobutene compound to the hydroxyalkylbenzocyclobutene compound. In a two-step process, formylbenzocyclobutenes are prepared from bromobenzocyclobutenes in 90% yield or from benzocyclobutenes in a 70% yield, and then converted to hydroxymethylbenzocyclobutenes for an overall yield of about 85% from a bromobenzocyclobutene or of about 65% from a benzocyclobutene.Type: GrantFiled: November 25, 1992Date of Patent: September 20, 1994Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews
-
Patent number: 5345005Abstract: In one embodiment, the invention relates to a catalyst in powdered form which comprises a major amount of the oxides of copper and zinc, and a minor amount of aluminum oxide wherein the pore volume of pores of said catalysts having a diameter between about 120 and about 1000 .ANG. is at least about 40% of the total pore volume. In another embodiment, the invention relates to a process for preparing hydrogenation catalysts comprising the oxides of copper, zinc and aluminum which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt and at least one water-soluble zinc salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions whereby an insoluble solid is formed;(D) recovering the insoluble solid.Type: GrantFiled: September 18, 1992Date of Patent: September 6, 1994Assignee: Engelhard CorporationInventors: Deepak S. Thakur, Brian L. Roberts, Thomas J. Sullivan, Anita L. Vichek
-
Patent number: 5313008Abstract: The invention relates to a process for the conversion of 8-hydroxymenthenes into 8-hydroxycymenes by treating the 8-hydroxymenthenes in the vapour phase with an alkaline dehydrogenation catalyst, e.g. palladium on an alkaline support. The process is carried out above 145.degree. C. The hydroxymenthene vapour is preferably passed through the catalyst system at a pressure below 8 kPa and/or with the aid of an inert gas or vapour. Oxygen may be present as a hydrogen acceptor. The process is particularly suitable for converting 8-hydroxy-p-menth-1-ene into 8-hydroxy-p-cymene. The reaction products are of value as intermediates in the preparation of musk fragrance chemicals.Type: GrantFiled: April 6, 1993Date of Patent: May 17, 1994Assignee: Unilever Patent Holdings B.V.Inventor: Christopher P. Newman
-
Patent number: 5288928Abstract: There is disclosed a process for the asymmetrical hydrogenation of (E)-2-methyl-3-phenyl-2-propen-1-ol of formula ##STR1## wherein R.sub.1 is as defined herein, to give compounds of formula ##STR2## The catalyst is a neutral or cationic rhodium complex of a chiral atropisomeric phosphine.Type: GrantFiled: July 20, 1992Date of Patent: February 22, 1994Assignee: Ciba-Geigy CorporationInventors: Emil A. Broger, Yvo Crameri, Hans P. Isenring, Albert Pfiffner
-
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
-
Patent number: 5286899Abstract: An efficient and commercially-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.Type: GrantFiled: August 27, 1992Date of Patent: February 15, 1994Assignee: Sepracor, Inc.Inventor: Yun Gao
-
Patent number: 5260477Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step (I) of dehydrogenating p-isobutylethylbenzene in a gaseous phase in the presence of a dehydrogenating metal catalyst to form p-isobutylstyrene and at least one unsaturated hydrocarbon compound selected from a group A defined in Claim 1; a step (II) of reacting p-isobutylstyrene obtained in the step (I) with carbon monoxide and hydrogen or with carbon monoxide and water or a lower alcohol in the presence of a transition metal complex carbonylating catalyst to form .alpha.-(4-isobutylphenyl)propionic acid or its precursor; and a step (III) of hydrogenating at least one unsaturated hydrocarbon compound selected from the group A obtained in the dehydrogenation step (I) to form p-isobutylethylbenzene, and recycling the thus formed p-isobutylethylbenzene through the step (I) as the raw material of the step (I).Type: GrantFiled: December 18, 1989Date of Patent: November 9, 1993Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuichi Tokumoto, Kazumichi Uchida
-
Patent number: 5254752Abstract: The invention provides a process for the preparation of a 4-halobenzyl alcohol of the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 - to C.sub.20 -alkyl, C.sub.2 - to C.sub.20 -alkoxyalkyl, C.sub.3 - to C.sub.20 -cycloalkyl, or C.sub.4 - to C.sub.30 -cycloalkylalkyl,R.sup.2 is C.sub.1 - to C.sub.20 -alkyl, C.sub.2 - to C.sub.20 -alkoxyalkyl, C.sub.3 - to C.sub.20 -cycloalkyl or C.sub.4 - to C.sub.30 -cycloalkylalkyl,X is halogen andm is 0 to 2,by reacting a haloaromatic carbonyl compound of the formula ##STR2## where R.sup.1, R.sup.2, X and m are as defined above, with hydrogen on a hydrogenation catalyst consisting essentially of copper oxide (I), copper oxide (II) and mixtures thereof in the presence of at least one primary, secondary or tertiary amine selected from the group consisting of acyclic, cyclic and heterocyclic aliphatic amines, in the presence or absence of an inert solvent, at from 50.degree. to 130.degree. C. and at from 10 to 200 bar.Type: GrantFiled: October 14, 1992Date of Patent: October 19, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Martin Brudermueller, Martin Schmidt-Radde
-
Patent number: 5254753Abstract: The invention provides a process for preparing aryl ethanols from aryl methyl ketones. The process involves a novel oxidation of the ketone to a dialkylacetal derivative of an aryl glyoxal, which is then hydrolyzed to an aryl glyoxal. The aryl glyoxal is then catalytically hydrogenated to reduce both carbonyl groups simultaneously to yield the aryl ethanol.Type: GrantFiled: February 25, 1992Date of Patent: October 19, 1993Assignee: Hoechst Celanese CorporationInventors: J. R. Durrwachter, G. N. Mott, H. Ramos, Jr., Ahmed Tafesh
-
Patent number: 5250744Abstract: Process for the production of 2-aryl-1,3-propanediols and novel intermediate compounds produced thereby.Type: GrantFiled: November 17, 1992Date of Patent: October 5, 1993Assignee: Ganes Chemicals Inc.Inventors: Francis Johnson, Richard Miller
-
Patent number: 5243095Abstract: In one embodiment, the invention relates to a catalyst in powdered form comprising the oxides of copper, iron, aluminum and manganese wherein the atomic ratio of copper to iron is at least 1:1. In another embodiment, the invention relates to a process for preparing such hydrogenation catalysts which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt, at least one water-soluble iron salt, and at least one water-soluble manganese salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions wherein an insoluble solid is formed;(D) recovering the soluble solid; and(E) calcining the recovered solid to form the desired catalyst.The invention also relates to a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters.Type: GrantFiled: April 24, 1992Date of Patent: September 7, 1993Assignee: Engelhard CorporationInventors: Brian D. Roberts, Deepak S. Thakur, Thomas J. Sullivan, Robert A. Plundo
-
Patent number: 5233099Abstract: A process for producing an alcohol by continuously passing a fatty acid ester, a fatty acid triglyceride or a fatty acid through a hydrogenation catalyst to thereby produce the aimed alcohol through catalytic reduction is disclosed, wherein the employed reactor is a fixed bed reactor in which the liquid phase and the gas phase are continuously passed together in descending parallel flows through the hydrogenation catalyst fixed in the reactor; and at least one cooling mean for cooling the reaction system is provided at a position in the vertical direction of the reactor. According to the process of the present invention with the use of a fixed bed reactor, an alcohol, which has extremely high qualities and a high purity and is contaminated with little hydrocarbon and aldehyde by-products, can be produced. The process of the present invention further makes it possible to omit the post-treatment for eliminating the by-products.Type: GrantFiled: December 24, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Kunizo Hashiba, Takahiro Kawakami
-
Patent number: 5233100Abstract: A process for producing an alcohol from a fatty acid ester, a fatty acid triglyceride or a fatty acid by continuously catalytically reducing the starting material in the presence of a hydrogenation catalyst is disclosed. In the process of the present invention, two reactors (i.e., the main reactor located upstream and the after reactor located downstream) being located in series are employed. In the process of the present invention, two reactors are employed and the temperatures thereof are individually controlled, whereby the conversion ratio is elevated while suppressing the formation of hydrocarbon and aldehyde by-products. Thus, an alcohol of extremely high quality and high purity can be produced. Further, the process of the present invention makes it possible to omit any post-treatment for eliminating the by-products. Furthermore, the active life of the hydrogenation catalyst can be remarkably prolonged by using three reactors (i.e., the guard reactor, the main reactor and the after reactor).Type: GrantFiled: December 27, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Atsuhito Mori, Takahiro Kawakami, Kunizo Hashiba, Kiyoshi Tsukada
-
Patent number: 5227538Abstract: A process is provided for the catalytic asymmetric reduction of ketones to provide alcohol reaction products which are enriched in one enantiomer. The asymmetric reduction is accomplished utilizing an achiral metal precatalyst in combination with an optically active additive.Type: GrantFiled: November 14, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Robert B. Grossman
-
Patent number: 5220020Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.Type: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
-
Patent number: 5214168Abstract: Epoxides are produced by an integrated process involving air oxidation of an aryl-substituted secondary alcohol, epoxidation of an olefin by the secondary alcohol oxidation product in the presence of a titanium silicalite catalyst, and generation of the secondary alcohol by hydrogenation.Type: GrantFiled: April 30, 1992Date of Patent: May 25, 1993Assignee: Arco Chemical Technology, L.P.Inventors: John G. Zajacek, Guy L. Crocco
-
Patent number: 5202502Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.Type: GrantFiled: March 23, 1992Date of Patent: April 13, 1993Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
-
Patent number: 5196601Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.Type: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
-
Patent number: 5196613Abstract: The invention concerns a novel process for the manufacture of 2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene, 1, commonly known as .alpha.-ambrinol. ##STR1## The process comprises reducing either an 8-halo-2-hydroxy-2,5,5-trimethyl-2,3,4,4a,5,6,7,8-ociahydronaphihalene (11a), alone or in admixture with a 1-halo-2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (11b), or reducing the 1,2-epoxide which can be formed therefrom, namely, 1,2-epoxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphihalene (111). The halohydrins 11 are prepared from 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydronaphihalene, IV.The compounds of formulas II and III are novel and form part of the present invention. The formula III epoxide possesses valuable odorant properties and its use as an odorant also forms part of the invention.Type: GrantFiled: January 21, 1991Date of Patent: March 23, 1993Assignee: Givaudan CorporationInventor: Peter Naegeli
-
Patent number: 5191133Abstract: The selective formation of 2-acetonaphthalene is achieved by acetylating naphthalene in the presence of liquid hydrogen fluoride. The 2-acetonaphthalene can be separated from the formed 1-acetonaphthalene isomer by successive hydrogenation of the isomer mixture and dehydration. The hydrogenation is selective to the 2-isomer while the 1-acetonaphthalene remains unreacted. Upon completion, 2-vinylnaphthalene can be distilled off from the unreacted 1-acetonaphthalene.Type: GrantFiled: May 22, 1991Date of Patent: March 2, 1993Assignee: Hoescht Celanese CorporationInventor: Henry C. Linstid, III
-
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
-
Patent number: 5166372Abstract: Olefins are epoxidized by hydrogen peroxide in the presence of an organorhenium oxide catalyst and an alkyl aryl secondary alcohol solvent. High yields of epoxides with minimal non-selective loss of either hydrogen peroxide or olefin are realized. The epoxidation may comprise one step of an integrated process wherein an oxidant mixture is generated by molecular oxygen oxidation of the alkyl aryl secondary alcohol and used directly in the epoxidation without further purification or extraction.Type: GrantFiled: February 7, 1992Date of Patent: November 24, 1992Assignee: Arco Chemical Technology, L.P.Inventors: Guy L. Crocco, Wilfred F. Shum, John G. Zajacek, Haven S. Kesling, Jr.
-
Patent number: 5166349Type: GrantFiled: June 17, 1991Date of Patent: November 24, 1992Assignee: The British Petroleum Company, p.l.c.Inventor: Stephen G. Davies
-
Patent number: 5144039Abstract: The process for producing an optically active alcohol of the present invention comprises allowing(A) an optically active amino alcohol represented by the general formula (I) ##STR1## (R.sup.1 is an aryl group, R.sup.2 is a lower alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group, and the carbon atoms having a mark * are each an asymmetric carbon atom) and an acid, or a salt of the optically active amino alcohol (I) and an acid,(B) a metal borohydride, and(C) at least one member selected from the group consisting of water, sulfides, cyclic ethers, ethers of mono alcohol to react witha prochiral ketone represented by the general formula (II) ##STR2## [R.sup.4 and R.sup.5 are different and each a lower alkyl group, an aryl group, an aralkyl group or a 2-substituted-1-triazoleethylene group represented by the general formula (III) ##STR3## (R.sup.6 is a halogen- or haloalkyl-substituted or unsubstituted phenyl group or a cycloalkyl group)].Type: GrantFiled: January 29, 1990Date of Patent: September 1, 1992Assignee: Sumitomo Electric Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Naoto Konya, Takaharu Ikeda
-
Patent number: 5128488Abstract: The asymmetric hydrogenation of carbonyl compounds is carried out in the presence of at least one transition metal complex MZq(M=metal of group VIII of the Periodic Classication; Z=ligand selected among the atoms and the molecules which may complex the metal M; and q=degree of corrdination of M) and of at least one chiral phosphorous-containing ligand having formula (I), wherein R is hydrocarbonated radical (alkyl, cycloalkyl and aryl); R.sup.1 is H, hydrocarbonated radical or PR.sub.2 ; R.sup.2 is H or hydrocarbonated radical R.sup.3,R.sup.4, necessarily different, are H and optionally functionalized hydrocarbonated radicals; R.sup.5 and R.sup.6 are H and optionally functionalized hydrocarbonated radicals; one of the radicals R.sup.3 and R.sup.4 possibly carrying a function - OPR.sub.2 or NPR.sub.2, R.sup.5 and R.sup.6 being in this case H when R.sup.1 is PR.sub.2 ; R.sup.2 and R.sup.3 and the atoms of N and C which cary them respectively forming a heterocycle; or R.sup.2 and R.sup.Type: GrantFiled: April 27, 1990Date of Patent: July 7, 1992Assignee: Societe Chimique des Charbonnages S.A.Inventors: Andre Mortreux, Francis Petit
-
Patent number: 5120853Abstract: The optically active benzylamine derivatives of the present invention are very useful for use as the asymmetric ligand of an asymmetric reducing agent. By using the optically active amine-boron complex prepared from the compound of the present invention, optically active products can be obtained in a specifically high optical yield. Moreover, the separation and recovery of the reaction products and asymmetric ligand can be easily achieved.Type: GrantFiled: February 8, 1991Date of Patent: June 9, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito
-
Patent number: 5113025Abstract: A process for selective reduction is provided wherein an organic compound containing a reducible group such as acid, acid chloride, ester, aldehyde, ketone, epoxide, amide, oxime, imine, nitrile, or the like, is reacted with a tertiary amine alane such that an alcohol or an amine is produced, substantially without reduction of another group in the molecule such as a halogen-containing functionality, nitro group, or double bond.Type: GrantFiled: March 5, 1991Date of Patent: May 12, 1992Assignee: Ethyl CorporationInventors: Won S. Park, Everett M. Marlett
-
Patent number: 5107037Abstract: The invention concerns a novel process for the manufacture of 2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene, I, commonly known as .alpha.-ambrinol. ##STR1## The process comprises reducing either an 8-halo-2-hydroxy-2,5,5-trimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalene (IIa), alone or in a mixture with a 1-halo-2-hydroxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (IIb), or reduced the 1,2-epoxide which can be formed therefrom, namely, 1,2-epoxy-2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octanhydronaphthalene (III). The halohydrins II are prepared from 1,1,6-trimethyl-1,2,3,7,8,8a-hexahydronaphthalene, IV.The compounds of formulas II and III are novel and form part of the present invention. The formula III epoxide possesses valuable odorant properties and its use as an odorant also forms part of the invention.Type: GrantFiled: June 6, 1990Date of Patent: April 21, 1992Assignee: Givaudan CorporationInventor: Peter Naegeli
-
Patent number: 5099054Abstract: In a method of carrying out organic conversions via heterogeneous phase transfer catalysis by contacting immiscible liquid phases containing respective substances capable of interacting, with a solid catalyst to promote the transfer of reactive species from one liquid phase to another, the improvement comprises employing as catalyst a cation exchanged form of a 2:1 layered silicate clay with layer charge densities in the range of above 0.4 to 2.0 containing an onium ion containing one or more alkyl hydrocarbon chains and maintaining the materials in emulsified form by having a sufficient chain length of an alkyl group relative to the charge density of the clay.Type: GrantFiled: February 14, 1991Date of Patent: March 24, 1992Assignee: Michigan State UniversityInventors: Thomas J. Pinnavaia, Chi-Li Lin
-
Patent number: 5099077Abstract: A method of using a chiral phosphorus-containing ligands comprising at least one amine radical and at least one dihydrocarbylphosphioxy radical of the formula W=OP (R).sub.2 ; from the group consisting of:those of the formula ##STR1## those of the formula ##STR2## those of the formula ##STR3## those of the formula ##STR4## in a hydrogenation reaction for the synthesis of optically active organic compounds comprising reacting at least one organic compound that does not possess a center of asymmetry with (A), on the one hand, at least one transition metal complex of the formula MZq in which M is a metal in group VIII of the Periodic Classification, q is the coordination number of the metal M, and Z is an atom or molecule capable of complexing the metal M and (B), on the other hand, at least one ligand L.Type: GrantFiled: October 11, 1989Date of Patent: March 24, 1992Assignee: Societe Chimique des Charbonnages S.A.Inventors: Michele Petit, Andre Mortreux, Francis Petit, Gerard Buono, Gilbert Peiffer
-
Patent number: 5091595Abstract: Syntheses for the preparation of 2-phenyl-1,3-propanediol, a useful intermediate for the preparation of 2-phenyl-1,3-propanediol dicarbamate, by the selective reduction of diethyl phenylmalonate with the Lewis acid type metal hydrides diisobutylaluminum hydride (DIBAH) or borane dimethylsulfide (BMS) in solution with heterocyclic ethers are disclosed.Type: GrantFiled: June 7, 1989Date of Patent: February 25, 1992Inventor: Young M. Choi
-
Patent number: 5075513Abstract: The invention provides cyclopentane derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5, each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkythio, alkysulphinyl, alkylsulphonyl, carbamoyl, alkylamindo, cycloalkyl or phenyl group, R.sup.1 and R.sup.2 independently represent a hydrogen atom or an alkyl group, and R.sup.3 represents an optionally substituted alkyl or aryl group; and a process for their preparation. Compounds of formulae I, II and IV are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives. Also, certain compounds of formula IV are themselves fungicidally active.Type: GrantFiled: August 23, 1989Date of Patent: December 24, 1991Assignee: Shell Internationale Research Maatschappij B.V.Inventor: Paul H. Briner
-
Patent number: 5072056Abstract: A novel method of preparing 2-phenyl substituted-1, 3-propanediols, useful intermediates in the synthesis of pharmaceutical preparations is disclosed.Type: GrantFiled: September 26, 1989Date of Patent: December 10, 1991Assignee: Carter-Wallace, Inc.Inventor: Frank J. Stiefel
-
Patent number: 5053559Abstract: 1,2,4-Trioxanes are subjected to reductive cleavage, thereby to produce a 1,2-diol and carbonyl compound. The process has applications both in the synthesis of 1,2-diols and the protection, in the course of organic synthesis, of carbonyl compounds.Type: GrantFiled: December 29, 1989Date of Patent: October 1, 1991Assignee: Oxaco S.A.Inventor: Charles W. Jefford
-
Patent number: 5030771Abstract: 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: GrantFiled: December 20, 1989Date of Patent: July 9, 1991Assignee: Huels AktiengesellschaftInventors: Werner Fuhrmann, Gunther Bub, Manfred zur Hausen
-
Patent number: 5023390Abstract: A process for production of 2,6-dimethylnaphthalene is disclosed; comprising the steps: (1) an acylation step where 2,4-dimethylisobutyrophenone is produced from m-xylene, propylene and carbon monoxide: (2) a hydrogenation step where the carbonyl group of the above 2,4-dimethylisobutyrophenone is hydrogenated: and (3) a dehydrogenation and cyclization step where the above hydrogenated product is subjected to dehydrogenation and cyclization to produce the desired 2,6-dimethylnaphthalene. The process enables efficiently producing high quality or high purity 2,6-dimethylnaphthalene.Type: GrantFiled: September 12, 1989Date of Patent: June 11, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Shuji Ebata, Hiroshi Machida, Koichi Kida
-
Patent number: 5023383Abstract: Aromatic alcohol is produced by reducing aromatic hydroperoxide with hydrogen in a liquid phase, using a Pt catalyst solely or a catalyst containing Pt and at least one element selected from the group consisting Pb, Sn, Cu, As, Sb, In, Se and Bi in a fixed bed reactor.Type: GrantFiled: January 3, 1990Date of Patent: June 11, 1991Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Masashi Inaba, Ryozo Hamana, Hideyuki Hase, Tatsuro Ashizawa
-
Patent number: 5015787Abstract: 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: GrantFiled: April 10, 1989Date of Patent: May 14, 1991Assignee: Allied-Signal Inc.Inventor: Jan F. Van Peppen
-
Patent number: 5012007Abstract: A method is provided for the production of 2,2-diorgano-1-indanones, e.g., 2,2-dimethyl-1-indanone, by reacting an alcohol which is the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)carbinol, e.g., 2-methyl-1-phenyl-1-propanol, with carbon monoxide in the presence of a Lewis acid catalyst, e.g., hydrogen fluoride, with any substituents on the phenyl group of the alcohol being hydroxy or organo. The foregoing reaction is preferably integrated with the preparation of the feed alcohol by reducing the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)ketone, e.g., isobutyrophenone, with a reducing agent containing available hydrogen, e.g., sodium borohydride, or with hydrogen gas in the presence of a hydrogenation catalyst.Type: GrantFiled: October 5, 1989Date of Patent: April 30, 1991Inventor: Varadaraj Elango
-
Patent number: 5008479Abstract: A process for production of 2,6-dimethylnaphthalene is disclosed, comprising the steps: (1) an acylation step where p-tolyl sec-butyl ketone is produced from toluene, n-butene and carbon monoxide: (2) a hydrogenation step where the carbonyl group of the p-tolyl sec-butyl ketone is hydrogenated: and (3) a dehydrogenation and cyclization step where the hydrogenated product obtained above is subjected to dehydrogenation and cyclization to produce the desired 2,6-dimethylnaphthalene. The process enables efficiently producing a high quality or high purity 2,6-dimethylnaphthalene.Type: GrantFiled: July 5, 1989Date of Patent: April 16, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Seiji Uchiyama, Takahiro Ojima, Koichi Kida
-
Patent number: 5004844Abstract: A process for the preparation of a primary or secondary alcohol, which comprises hydrogenating respectively an aldehyde or ketone in the presence of a catalyst system comprising a platinum compound, an acid having a pKa in the range from about 2 to about 10.5 and a phosphorus compound of the formula R.sup.1 R.sup.2 POH, wherein R.sup.1 and R.sup.2 each independently represents an alkyl group or a phenyl group, at a temperature in the range from about 20.degree. to about 150.degree. C. and at a pressure in the range from about 1 to about 100 bar.Type: GrantFiled: June 28, 1989Date of Patent: April 2, 1991Assignee: Shell Oil CompanyInventors: Petrus W. N. M. Van Leeuwen, Cornelis F. Roobeek
-
Patent number: 4996374Abstract: A process for the hydrogenation of ACP to MBA over a supported palladium catalyst wherein a solvent comprised of ethylbenzene and/or MBA is employed and a small amount of water effective to suppress catalyst deactivation is incorporated in the feed. A further improvement comprises maintaining hydrogen pressure on the catalyst during and between hydrogenation runs.Type: GrantFiled: December 15, 1989Date of Patent: February 26, 1991Assignee: Arco Chemical Technology, Inc.Inventors: Shaw-Chan Lin, Robert N. Cochran