Abstract: Epoxides are produced by an integrated process involving molecular oxygen oxidation of an alkylammonium salt of a sulfonic acid-substituted anthrahydroquinone, epoxidation of an ethylenically unsaturated substrate using the hydrogen peroxide-containing product obtained by such oxidation in the presence of a titanium silicalite catalyst, and regeneration of the anthrahydroquinone by hydrogenation of the anthraquinone co-product. Oxidation and epoxidation may be performed concurrently. The alkylammonium salts have the advantage of being highly soluble in polar protic media such as water and lower alcohols.
Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.
Type:
Grant
Filed:
September 23, 1994
Date of Patent:
October 31, 1995
Assignee:
Hoechst Aktiengesellschaft
Inventors:
Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.
Type:
Grant
Filed:
February 14, 1995
Date of Patent:
October 31, 1995
Assignee:
Hoechst Aktiengesellschaft
Inventors:
Helmut Bahrmann, Wolfgana Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
Abstract: The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof.These compounds have valuable pharmaceutical properties.
Type:
Grant
Filed:
June 7, 1994
Date of Patent:
October 10, 1995
Assignee:
Ciba-Geigy Corporation
Inventors:
John G. Dingwall, Josef Ehrenfreund, Roger G. Hall, James Jack
Abstract: A novel process for preparing enantiomerically pure (S)- or (R)-but-3-en-2-ol compounds includes the following reaction steps:(a) reacting an alkyl ester of D- or L-lactic acid with a hydropyran compound to obtain a lactate ester having a hydropyranyl ether group,(b) reducing the lactate ester with an aluminum hydride at a temperature below 0.degree. C. to obtain a propionaldehyde having a hydropyranyl ether group,(c) reacting the propionaldehyde with an alkyl phosphonium salt to obtain a 3-butene having a hydropyranyl ether group, and(d) cleaving the hydropyranyl ether group to prepare the enantiomerically pure (S)- or (R)- but-3-en-2-ol.
Abstract: Methanol can be substantially removed from dimethyl carbonate (DMC)/methanol mixtures by absorption on ion exchange resins. The enriched DMC is obtained as filtrate. The absorption is carried out at from -50.degree. C. to +100.degree. C. and 0.1-10 bar.
Type:
Grant
Filed:
December 8, 1994
Date of Patent:
October 3, 1995
Assignee:
Bayer Aktiengesellschaft
Inventors:
Ingo Janisch, Heinz Landscheidt, Werner Struver, Alexander Klausener
Abstract: Compounds of the formula ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.
Type:
Grant
Filed:
December 30, 1993
Date of Patent:
September 19, 1995
Assignee:
Allergan, Inc.
Inventors:
Roshantha A. Chandraratna, Richard L. Beard
Abstract: A nonsolvent process of synthesizing bis(2,2-dinitropropyl)formal (BDNPF) is disclosed. In the process, 2,2-dinitropropanol (DNPOH) is reacted at low temperature with a formaldehyde source in the presence of a protic acid catalyst, such as H.sub.2 SO.sub.4, HCl, H.sub.3 PO.sub.4, or HBr. To inhibit byproduct formation, the reaction temperature is maintained from about -30.degree. C. to 30.degree. C. Upon completion of the reaction, the reaction solution is quenched with water and washed with an aqueous hydroxide ion solution. The hydroxide ion concentration should be sufficient to neutralize the protic acid catalyst during the quenching step and to solubilize unreacted 2,2-dinitropropanol as well as other aqueous soluble byproducts in the reaction solution. The BDNPF product is extracted with a low boiling temperature polar organic solvent, such as methyl tert-butyl ether (MTBE) or equivalent solvent. The organic solvent is evaporated to yield usable BDNPF product.
Abstract: The present invention provides special epoxy derivative (1), cyclohexanone derivative (2), cyclohexenone derivative (3) and 3-substituted cyclohexenone derivative (4) which are useful as intermediates for synthesizing physiologically active materials, and a method for stereoselectively introducing substituted groups. Further, the present invention provides a method for synthesizing optically active compounds, such as optically active carvone via these intermediates.
Abstract: Disclosed are the improvements of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl (meth)acrylate and 3,4-epoxycyclohexyl methyl (meth)acrylate which is prepared by the improvements, including only minor amounts of polymers having a low molecular weight composed of 3,4-epoxycyclohexyl methyl (meth)acrylate itself.Furthermore, disclosed is a 3,4-epoxycyclohexyl methyl (meth)acrylate composition which has an excellent resistance to coloring, including a specified organic phosphorous compound.
Type:
Grant
Filed:
January 10, 1995
Date of Patent:
August 29, 1995
Assignee:
Daicel Chemical Industries, Ltd.
Inventors:
Akihiro Kuwana, Kimihide Honda, Kunio Koga
Abstract: The present invention is directed to a method of dimerizing lower olefins which comprises dimerizing a lower olefins in the presence of a catalyst, wherein the catalyst used comprises a nickel compound, an organic aluminum compound, and a phosphite compound having the general formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are phenyl groups optionally substituted by substituents and may be different from each other, at least two of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 have a hydrocarbon group as a substituent in the ortho position; A is a divalent aliphatic, alicyclic or aromatic hydrocarbon group which optionally has a substituent; and n is 0 or 1. The present invention is also directed a method of producing alcohol by means of hydroformylating and hydrogenating the newly formed olefins obtained through the said dimerization method of the lower olefins.
Abstract: A cotelomer of --CH.sub.2 CF.sub.2 -- (VDF) units and CF.sub.2 CF(CF.sub.3)-- (HFP) units characterized in that the HEP units comprise at least 33% of all VDF and HFP units in the cotelomer combined. Also claimed is a process for preparing a cotelomer in the liquid state comprising reacting (A) a bromine geminal telogen having the general formula RC(R')Br.sub.2 wherein R and R' are selected from the group consisting of F and perfluorinated alkyl radicals having 1 to 8 carbon atoms; (B) 1,1-difluoroethene, and (C) hexafluoropropene, the molar ratio of said components (A):(B):(C) being x:1:1 to x:1:5, in which x is 1 to 5.
Type:
Grant
Filed:
October 27, 1994
Date of Patent:
August 29, 1995
Assignee:
Dow Corning Corporation
Inventors:
Gerardo Caporiccio, Richard D. Chambers, Lee D. Proctor
Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH=CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2x+1. The invention is also directed to a practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.
Type:
Grant
Filed:
May 16, 1994
Date of Patent:
August 29, 1995
Assignee:
AlliedSignal Inc.
Inventors:
Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung
Abstract: 2-[4-(4-azolylbutyl)-1-piperazinyl]-pyrimidine derivatives characterized in that they correspond to the general formula I ##STR1## in which X.sub.2 represents a nitrogen atom or a C-R.sub.2 group, X.sub.4 represents a nitrogen atom or a C-R.sub.4 group, X.sub.5 represents a nitrogen atom or a C-R.sub.5 group, the process for preparing them, their application as medicinal product, and the pharmaceutical compositions containing them.
Type:
Grant
Filed:
February 4, 1994
Date of Patent:
August 22, 1995
Assignee:
Laboratorios Del. Dr. Esteve, S.A.
Inventors:
Jordi Frigola-Constansa, Ramon Merce-Vidal
Abstract: Manumycin C, Manumycin D and Manumycin E, obtainable by cultivation of a strain of Streptomyces sp. A.T.C.C. No. 55484, oxidized derivatives thereof and salts and prodrugs of these compounds. The novel compounds have antibacterial and antitumor activity.
Abstract: A method, especially applicable on a continuous basis to commercial process streams, for treating unwanted by-products and/or impurities contained in those streams. The method comprises the reaction in situ of such by-products or impurities with a reagent, preferably selected for its reactivity under ambient conditions of the process stream, to produce one or more materials which may then be separated from the process by economical means. The treated stream may be recycled to the process for further processing. While the method is not limited as to the process to which it is applied nor to the reagent or reagents used, in one convenient embodiment, formaldehyde in aqueous solution is reacted with an alkali metal sulfite or bisulfite to produce the corresponding salt, which may then be separated essentially completely by, e.g., distillation or membrane separation, etc., or its concentration in the process may be controlled by, e.g., continuous removal of a purge stream, etc.
Type:
Grant
Filed:
June 7, 1994
Date of Patent:
August 8, 1995
Assignee:
Union Carbide Chemicals & Plastics Technology Corporation
Abstract: A plural stage process for the production of tertiary butyl alcohol from isobutane wherein isobutane is reacted with oxygen in a first reactor to prepare a primary liquid reaction mixture comprising unreacted isobutane, tertiary butyl alcohol, tertiary butyl hydroperoxide and small amounts of oxygen-containing by-products, distilling the primary reaction product to provide a first lighter isobutane recycle distillation fraction and a first heavier liquid distillation fraction comprising the debutanized mixture of tertiary butyl hydroperoxide with tertiary butyl alcohol, diluting the first heavier liquid distillation fraction with an amount of tertiary butyl alcohol sufficient to provide a feed mixture comprising about 15 to 25 wt. % of tertiary butyl hydroperoxide, about 75 to 85 wt.
Type:
Grant
Filed:
August 11, 1994
Date of Patent:
July 25, 1995
Assignee:
Texaco Chemical Inc.
Inventors:
Yu-Hwa E. Sheu, John R. Sanderson, Mark A. Mueller, William A. Smith
Abstract: Noble metal or other preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are reactivated or regenerated by treatment with a mixture of an aqueous organic acid solution and an alcohol at a temperature of about 120.degree. C. to 170.degree. C. and a pressure of about 13.78 MPa to 31.00 MPa for about 2 to 50 hours.
Abstract: 1,3-Butadiene is hydroformylated at 60.degree. to 150.degree. C. and 1 to 20 MPa in the presence of an aqueous solution which contains, as catalyst, at least one water-soluble rhodium compound and at least one water-soluble organic phosphine. A pH of 8 to 11 is maintained in the aqueous catalyst solution to increase the selectivity of the reaction with respect to the formation of n-five carbon aldehydes and their secondary products. The latter, in particular, can be hydrogenated to 2-propylheptanol, useful as the alcohol component of phthalic ester plasticizers.
Abstract: Excess alcohol, e.g. methanol contained in a C.sub.4 -C.sub.6 hydrocarbon stream is removed in process using less water and energy than a conventional water wash by subjecting the stream to a first single stage water wash with 2 to 10 wt % water based on the hydrocarbon where most of the alcohol is removed and then washing the raffinate having reduced methanol therefrom subjected to multistage water wash to remove the remainder of the alcohol.