Abstract: A process for producing an omega-functionalized aliphatic carboxylic acid starting from cyclohexanone and omega-functionalized .alpha.-olefins. The process comprises an addition step, an oxidation step, an isomerization step, one or more hydrogenation steps and hydrolysis. The process allows to use raw materials that are available at low cost and to achieve high selectivity and high yield with industrially simple steps. The process includes the production of new intermediate products.
Type:
Grant
Filed:
April 16, 1996
Date of Patent:
February 16, 1999
Assignee:
Industrie Chimiche Caffaro, S.p.A.
Inventors:
Livius Cotarca, Paolo Maggioni, Alfonso Nardelli
Abstract: The present invention relates to a process for the preparation of carboxylic acids from unsaturated fatty acids and/or their derivatives.The process of the invention is characterized in that it comprises the following stages:a stage which consists in oxidizing an unsaturated fatty acid in the form of acid and/or of ester using hydrogen peroxide, in the presence of a metal oxide or of a carboxylic acid optionally used in combination with a ruthenium-based catalyst,a stage which consists in reacting the reaction mixture originating from the preceding stage with nitric acid in the presence of a vanadium-based catalyst, optionally used in combination with a cocatalyst, and thena stage of recovery of the mono- and dicarboxylic acids.It is particularly well suited for the preparation of saturated mono- and dicarboxylic acids obtained from unsaturated fatty acids such as oleic acid or from oils and fats.
Abstract: A process for the continuous production of monocarboxylic acids from the corresponding alcohols by alkali fusion wherein the oxidation is continuously accomplished in an extrusion reactor without addition of diluents and the alkali salts of the monocarboxylic acids are discharged from the reactor as a solid product and are directly neutralised with mineral acids. High-purity monocarboxylic acids are obtained after phase separation.
Type:
Grant
Filed:
June 14, 1996
Date of Patent:
January 12, 1999
Assignee:
RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
Inventors:
Albert Thomas Herrmann, Arnold Meyer, Erich Scherf, Clemens Schroder, Ansgar Reichenauer, Ernst Tonsen
Abstract: A method of synthesizing 9-cis-retinoic acid, all-trans-retinoic acid or 9-nor-retinoic acid is disclosed. The method comprises the steps of adding a Grignard reagent of ##STR1## to 2,2,6 trimethyl cyclohexanone is disclosed. R is a methyl group or H and the CH.sub.2 --OH group is in either the cis or trans orientation relative to the HC.tbd.C- group. The resulting product is converted into retinoic acid. In the preferable form of the present invention, a tritium-labelled retinoic acid is synthesized, wherein the labelling is at the C.sub.20 position. A preparation of tritium-labelled 9-cis-retinoic acid with a specific activity of greater than 65 Ci/mmol is also enclosed. In a most preferred embodiment, the specific activity is greater than 75 Ci/mmol.
Abstract: A process for preparing polyenecarbonyl compounds having a high all-E content and their acetals or ketals by aldol condensation or Horner-Emmons reaction comprises carrying out the reaction, for the purposes of the preferred formation of a double bond of E configuration and in order to maintain the E configuration of the double bonds in the stating compounds as completely as possible, in the presence of oxygen or an oxygen-inert gas mixture or nitric oxide or a nitric oxide-inert gas mixture and/or in the presence of specific stable radicals and/or in the presence of quinones or quinone derivatives.
Type:
Grant
Filed:
July 6, 1995
Date of Patent:
June 30, 1998
Assignee:
BASF Aktiengesellschaft
Inventors:
Walter Dobler, Wolfgang Krause, Joachim Paust, Otto Worz, Udo Rheude, Wolfram Burst, Gunter Dauwel, Armin Bertram, Bernhard Schulz, Gunter Wegner, Peter Munster, Hansgeorg Ernst, Arno Kochner, Heinz Etzrodt
Abstract: A process for the preparation of carboxylic acids and esters thereof, which involves the steps of (a) mixing an unsaturated fatty acid or corresponding ester with an oxidative substance in the presence of a catalyst selected from the group consisting of oxides of tungsten and molybdenum and their acids and alkaline salts, (b) reacting the product mixture from step (a), which comprises vicinal diols, with oxygen or an oxygen-containing gas in the presence of a cobalt-containing compound which acts as a catalyst. The product mixture from step (a) is not subjected to any purification treatments prior to undergoing step (b).
Type:
Grant
Filed:
May 1, 1995
Date of Patent:
February 3, 1998
Assignee:
Novaol S.r.l.
Inventors:
Giampiero Sabarino, Andrea Gardano, Marco Foa'
Abstract: A process for forming acids from aldehydes which comprises reacting an oxo aldehyde with water in the presence of an acid-forming catalyst and in the absence of hydrogen, and at a pressure of about 0.1 to 6.99 MPa and a temperature of about 93.degree. to 205.degree. C., thereby converting aldehyde to an oxo acid.
Abstract: A process is disclosed for preparing .alpha.-branched aliphatic monocarboxylic acids with 12 to 48 carbon atoms. In a first step of the process (a), .alpha.-branched aliphatic monohydric alcohols (Guerbet alcohols) are converted in the presence of caustic alkali into the alkali salts of the corresponding .alpha.-branched aliphatic monocarboxylic acids. In a second step of the process (b), the .alpha.-branched aliphatic monocarboxylic acids are released from the alkali salts by soap splitting in the presence of an inert diluting agent.
Type:
Grant
Filed:
August 29, 1995
Date of Patent:
August 5, 1997
Assignee:
Henkel Kommanditgesellschaft auf Aktien
Inventors:
Gerhard Mueller, Bernhard Gutsche, Karl-Heinz Schmid, Frank Bongardt, Lutz Jeromin, Eberhard Peukert, Hermann Frankenbach
Abstract: Chemical synthesis of N-acyl-N-alkylcarboxylates through oxidation of substituted amides formed from carboxylic acid esters and an N-alkyl-N-alkanolamine.
Type:
Grant
Filed:
June 23, 1995
Date of Patent:
July 8, 1997
Assignee:
The Procter & Gamble Company
Inventors:
James Carey Letton, Larry Eugene Miller
Abstract: A method for preparing a carboxylic acid is provided. The method includes contacting an olefinic compound or a vicinal dihydroxy compound with oxygen in the presence of a protic organic solvent, an inorganic oxide catalyst and a peroxidant such as hydrogen peroxide or an peralkanoic acid. The inorganic oxide catalyst includes an oxide of tungsten, molybdenum, niobium, vanadium, tantalum, titanium, or yttrium.
Type:
Grant
Filed:
June 5, 1995
Date of Patent:
January 21, 1997
Assignee:
North Dakota State University
Inventors:
Mukund P. Sibi, Philip Boudjouk, Jianguo Ji
Abstract: Methods for the synthesis of 9-cis monotritium-labeled retinoids, and their use in the discovery of Retinoid X Receptor ligands are provided. In addition, 9-cis monotritium-labeled retinoids, as well as novel intermediates and tritium-labeled intermediates formed during the synthesis of 9-cis monotritium-labeled retinoids are also provided.
Abstract: Nylon-11 monomer, 11-aminoundecanoic acid, is synthesized from 12-oxododecanoic acid oxime in a three-step reaction sequence which involves a Beckmann rearrangement, Hofmann degradation and hydrolysis. The aldoxime acid is hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid. This amide is then treated with a solution of sodium methoxide and bromine at 70.degree.-80.degree. C. to give 11-(methoxycarbonylamino)undecanoic acid, which upon basic hydrolysis and subsequent neutralization, yields the 11-aminoundecanoic acid.
Type:
Grant
Filed:
July 19, 1993
Date of Patent:
March 12, 1996
Assignee:
Howard University
Inventors:
Folahan O. Ayorinde, Chukwuma P. Nwaonicha
Abstract: A method for the preparation of .alpha.-substituted .omega.-dihydroperluoroalkane derivatives of the general formula H(CF.sub.2 CF.sub.2).sub.n R wherein R=H or COOH, and n=1-10 is characterized by oxidizing .alpha., .alpha., .omega.-trihydroperfluoroalcohols with an oxygen gas or an oxygen-containing gas in the presence of a homogeneous copper catalyst and an alkaline agent in an organic solvent with subsequent isolation of the desired product.
Type:
Grant
Filed:
July 15, 1994
Date of Patent:
February 27, 1996
Assignee:
Hoechst Aktiengesellschaft
Inventors:
Irina P. Skibida, Andrei M. Sakharov, Jury L. Bakhmutov, Vladimir F. Denisenkow, Nina P. Martynova
Abstract: A method of preparing carboxylic acids or esters thereof by the oxidative cleavage of unsaturated fatty acids or esters thereof is carried out in a two-phase aqueous-organic system in which the organic phase contains the unsaturated fatty acid and/or the esters thereof and the aqueous phase contains hydrogen peroxide. The oxidative cleavage is carried out in the presence of a catalytic system including a catalyst belonging to the group constituted by tungstic and molybdic acids and alkaline salts thereof, and an onium salt which acts as a phase-transfer agent for the catalyst, and has the formula:(R.sub.2 R.sub.3 R.sub.4 R.sub.5 M).sup.+ Y.sup.-in which R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent hydrocarbon groups of which at least one must have more than 10 carbon atoms,M is N or P, andY.sup.- is an inorganic anion.
Type:
Grant
Filed:
December 10, 1992
Date of Patent:
August 9, 1994
Assignee:
Novamont S.p.A.
Inventors:
Andrea Gardano, Giampiero Sabarino, Marco Foa
Abstract: An improved liquid-phase process for preparing carboxylic acids having (n+1) carbon atoms by rhodium catalyzed carbonylation of an alcohol having n carbon atoms is provided. The process is particularily suitable for preparing acetic acid from methanol in commercial carbonylation reactors operating at steady-state with a low standing quantity of water (e.g. 0.5 to 5% by weight). The improvement lies in carrying out the carbonylation in the presence of an iodide stabilizer (e.g. lithium iodide) and a Group VI B metal costabiliser. The process can optionally be carried out in the presence of hydrogen.
Abstract: .omega.-Hydroxy fatty acids usable for the synthesis of medicaments, perfumes and polymers are produced by subjecting an alkali or alkaline earth metal salt of long-chain dicarboxylic acid monoester to a reduction with a borohydride compound or catalytic hydrogenating reduction treatment.
Abstract: A process for the continuous production of fatty acid soaps by reaction with solid metal oxides, hydroxides, hydrogen carbonates and carbonates of Mg, Ca, Ba, Pb, Al, Zn, Co, Fe, Cd and Zr, in which the fatty acids are subjected to a rotational movement by mechanical transport and the metal compounds are subjected to rotation in the opposite direction by mechanical transport, the two reactants are combined in the reaction zone of a tube reactor and are reacted in 0.5 to 50 seconds.
Type:
Grant
Filed:
August 29, 1988
Date of Patent:
February 9, 1993
Assignee:
Henkel Kommanditgesellschaft auf Aktien
Inventors:
Franz-Josef Carduck, Hubert Harth, Harald Liebs
Abstract: Quinone derivatives of the general formula: ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R.sup.1 and R.sup.2 combine with each other to represent --CH.dbd.CH--CH.dbd.CH--R.sup.3 is a hydrogen atom or a methyl group; R.sup.4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R.sup.5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C.dbd.C--, --CH.dbd.CH--, ##STR2## n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturated fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.
Abstract: A process for the preparation of an alkanoic acid which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid, and a bromide ion-containing compound in the presence of an oxidant at a temperature in the range of from about 25.degree. C. to about 60.degree. C., and thereafter separating out the alkanoic acid.