Patents Examined by Werren B. Lone
-
Patent number: 5399786Abstract: The present invention has as purpose a process for the manufacture of tert-butylphenols, mainly of tertbutyl-4-phenols from a phenol and an alkyltert-butylether. The improvement consists in separating in at least two steps, the reaction of phenol alkylation and transalkylation/isomerization of undesirable alkyltert-butylphenols, enabling the flexibilization of the type and quality of end product, and easily adapt to the demands of the market, plus the fact that the total yield improved as well as this improvement has good industrial hygiene properties.Tert-butylphenols are useful intermediate products is the manufacture of phenolic resins or antioxydizing agents for rubber and for several plastic substances.Type: GrantFiled: July 13, 1993Date of Patent: March 21, 1995Assignee: Rhodia S/AInventors: Antonio U. B. Queiroz, Lumi T. Aikawa, deceased
-
Patent number: 5399790Abstract: Compounds such as 1-(4'-nitrophenyl)-2-propen-1-ol are disclosed which are non-steroidal mechanism-based inactivators of rat liver 3.alpha.-hydroxysteroid dehydrogenase. The corresponding ketones are time dependent inactivators of cyclooxygenase (PGH.sub.2 -synthase).Type: GrantFiled: August 30, 1993Date of Patent: March 21, 1995Assignee: Trustees of The University of PennsylvaniaInventors: Trevor M. Penning, Joseph W. Ricigliano
-
Patent number: 5395991Abstract: 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: GrantFiled: December 30, 1993Date of Patent: March 7, 1995Assignee: Eastman Chemical CompanyInventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
-
Patent number: 5395986Abstract: 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: GrantFiled: December 30, 1993Date of Patent: March 7, 1995Assignee: Eastman Chemical CompanyInventors: John Scarlett, Michael A. Wood
-
Patent number: 5395979Abstract: A catalyst for use in hydroformylation of olefins which comprises a Group VIII noble metal complexed with a phosphine ligand having at least one alkyl or aryl group bonded thereto, such as tris-4-propylphenyl phosphines and tris-4-octylphenyl phosphines. These and other triphenylphosphine catalysts can be separated from a crude reaction product of a noble metal-catalyzed hydroformylation reaction by contacting the crude reaction product with a dense polymeric, nonpolar membrane, preferably nonpolar polyolefin membranes.Type: GrantFiled: February 25, 1993Date of Patent: March 7, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Harry W. Deckman, Edward Kantner, Joel R. Livingston, Jr., Michael G. Matturro, Edmund J. Mozeleski
-
Patent number: 5395980Abstract: In the non-catalytic liquid phase oxidation of isobutane, it has been found that the reaction is initiated with 0.05 wt % to 0.08 wt % ditertiary butyl peroxide.Type: GrantFiled: March 21, 1994Date of Patent: March 7, 1995Assignee: Texaco Chemical Inc.Inventors: Mark A. Mueller, John R. Sanderson
-
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: 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
-
Patent number: 5395987Abstract: 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: GrantFiled: December 30, 1993Date of Patent: March 7, 1995Assignee: Eastman Chemical CompanyInventors: Colin Rathmell, Richard C. Spratt, Michael W. M. Tuck
-
Patent number: 5395985Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds to and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.Type: GrantFiled: March 4, 1994Date of Patent: March 7, 1995Assignee: Daicel Chemical Industries, Ltd.Inventor: Fumio Toda
-
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: 5395994Abstract: This invention provides an environmentally acceptable method for recovery of phenolic and brominated phenolic compounds, alcohol solvent, and bromide values from the a reaction medium liquid mixture formed in the production of a tetrabromobisphenol-A predominant product. The process comprises (a) separating the tetrabromobisphenol-A predominant product and alkyl bromide from the reaction medium thereby forming a liquid mixture containing alcohol, phenolic and brominated phenolic compounds, HBr, and water; (b) treating the liquid mixture with a sufficient amount of alkaline or alkaline earth metal hydroxide so as to form a treated aqueous mixture having a pH in the range of from about 9.5 to about 14.0, and containing MBr.sub.Type: GrantFiled: May 19, 1994Date of Patent: March 7, 1995Assignee: Albemarle CorporationInventors: Robert E. Williams, William J. Cranston, III
-
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: 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
-
Patent number: 5387725Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.Type: GrantFiled: July 12, 1993Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
-
Patent number: 5387727Abstract: Disclosed is a production method of generating pentafluorophenyl alkali metal salt represented by a general formula C.sub.6 F.sub.5 M (M denotes an alkali metal ion) by reacting pentafluorobenzene represented by C.sub.6 HF.sub.5 with an organometallic compound represented by a general formula RM (R denotes a hydrocarbon group of 1.about.10 carbon number which may contain a functional group having no influence on the reaction.Type: GrantFiled: December 17, 1993Date of Patent: February 7, 1995Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
-
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: 5387724Abstract: Phenols, and related aromatic compounds, phenolic ethers, can be hydroxylated selectively using hydrogen peroxide in the presence of an amorphous or microcrystalline zirconium phosphate catalyst in a solvent containing an aliphatic carboxylic acid. The process is particularly suitable for phenol itself, and advantageously employs a partially dehydrated microcrystalline catalyst obtained by heating an hydrated microcrystalline zirconium phosphate for example at about 100.degree. C. A convenient reaction temperature is 50.degree. to 90.degree. C., and convenient solvent is acetic acid. In an improved method of producing the catalyst, zirconium phosphate is precipitated from an aqueous phosphoric acid solution of zirconium oxychloride in the presence of a cationic phase transfer agent such as an alkylpyridinium salt or tetraalkylquaternary ammonium salt or a nonionic surfactant such as an alcohol ethoxylate.Type: GrantFiled: October 12, 1993Date of Patent: February 7, 1995Assignee: Solvay Interox LimitedInventors: Alexander Johnstone, William R. Sanderson, Robert C. Wasson
-
Patent number: 5387720Abstract: A process for the production of acrolein by dehydration of glycerol in the liquid phase or in the gaseous phase, in each case on acidic solid catalysts, is described. Compared with previously known processes, the space-time yield and catalyst service life may be surprisingly increased with higher selectivity by treating a glycerol-water mixture with a glycerol content of 10 to 40 wt. % at 180.degree. to 340.degree. C. (liquid phase) or at 250.degree. to 340.degree. C. (gaseous phase) on a solid catalyst with an H.sub.o value (Hammett acidity function) of less than +2, preferably less than -3.Type: GrantFiled: November 12, 1993Date of Patent: February 7, 1995Assignee: Degussa AktiengesellschaftInventors: Armin Neher, Thomas Haas, Dietrich Arntz, Herbert Klenk, Walter Girke
-
Patent number: 5387719Abstract: A process for the preparation of aldehydes by hydroformylation of olefins having more than 7 carbon atoms, comprising hydroformylation by means of a rhodium catalyst dissolved homogeneously in the reaction medium, removal of the rhodium catalyst from the hydroformylation reaction product, and recycling of the rhodium separated off from the hydroformylation product into the hydroformylation step, in which the rhodium catalyst is extracted from the hydroformylation product into the aqueous phase by means of an aqueous solution of a nitrogen-containing complexing agent from the group comprising of sulfonated pyridines, sulfonated quinolines, substituted or unsubstituted, sulfonated or sulfonated substituent-carrying 2,2'-bipyridines, 1,10-phenanthrolines, 2,2'-biquinolines, 2,2',6',2"-terpyridines and porphines, and/or from the group comprising of carboxylated pyridines, carboxylated quinolines, substituted or unsubstituted, carboxylated or carboxylated substituent-carrying 2,2'-bipyridines, 1,10-phenanthrolinesType: GrantFiled: September 14, 1993Date of Patent: February 7, 1995Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Michael Roeper, Rocco Paciello