Abstract: The present invention relates to a novel process for the preparation of esters of the general formula I
from compounds of the general formula II contained in aqueous solutions
which comprises
a) extracting the compounds of the general formula II directly or after liberation from their salts in the presence of a C1-C8-alcohol and a water-immiscible solvent and
b) then esterifying with the C1-C8-alcohol in the presence of a catalyst and of an entraining agent under the conditions of an azeotropic distillation,
where the process steps (a) and (b) can be carried out separately in terms of time and space or else in a successive continuous or batchwise sequence and where the variables and substituents in the formulae I and II have the following meanings:
R1=F, Cl, —OH, —OC1-C10-alkyl,
R2=H, C1-C10-alkyl;
R3=C1-C8-alkyl,
Q=—OH, —O−K+, where K+ is an alkali metal cation or alkaline earth metal cation,
n&equ
Abstract: The present invention relates to the preparation and biological activity of 3-deoxy-Dmyo-inositol ether lipid analogs as inhibitors of phosphatidylinositol-3-kinase signaling and cancer cell growth. The compounds of the present invention are useful as anti-tumor 5 agents which effectively inhibit the growth of mammalian cells.
Type:
Grant
Filed:
June 12, 2001
Date of Patent:
December 23, 2003
Assignees:
Arizona Board of Regents on behalf of the University of
Arizona, Georgetown University School of Medicine
Inventors:
Alan P. Kozikowski, Lixin Qiao, Garth Powis
Abstract: A process for producing an ester comprises the steps of: (a) feeding to a first vessel a feed that comprises organic acid, alcohol, and water, whereby organic acid and alcohol react to form monomeric ester and water, and whereby a first liquid effluent is produced that comprises as its components at least some ester, alcohol, and water, the components of the first liquid effluent being substantially in reaction equilibrium; and (b) feeding the first liquid effluent to a second vessel, whereby a vapor product stream and a second liquid effluent stream are produced, the vapor stream comprising ester, alcohol, and water, wherein the second vessel is maintained substantially at vapor-liquid equilibrium but not substantially at reaction equilibrium.
Abstract: The present invention provides a phthalate-free plasticizer for polymer resins. The phthalate-free plasticizer according to the invention includes a mixture of different triesters of glycerin, at least one of which meets the formula:
CH2(OOR1)CH(OOR2)CH2(OOR3)
wherein at least two of R1, R2, and R3 are different alkyl or aryl groups. Phthalate-free plasticizers according to the invention can be made by esterifying glycerin with a mixture of acids in the presence of a catalyst. Preferably, the mixture of acids includes at least two selected from the group consisting of alkyl acids and aryl acids, with each acid in the mixture containing up to about 11 carbon atoms, and more preferably from about 4 to about 9 carbon atoms each. The plasticizer according to the invention can be used to modify the properties of a wide variety of polymers including vinyl polymers, rubbers, polyurethanes, and acrylics, and has superb thermostability and low volatility.
Type:
Grant
Filed:
December 20, 2001
Date of Patent:
November 25, 2003
Assignee:
Ferro Corporation
Inventors:
Lei Zhou, George Schaefer, William W. Knickmeyer, David Paul
Abstract: An accelerated process for preparing a methyl ester having formula (III)
said process comprising reacting a carboxylic acid or salt thereof having formula (I)
with dimethyl carbonate having formula (II)
in the presence of a catalyst selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; 4-dimethylaminopyridine; and combinations thereof, wherein R1 is selected from the group consisting of an alkyl, aryl, alkoxy, alkenyl, cycloalkyl, benzocycloalkyl, cycloalkylalkyl, aralkyl, heterocyclic, heteroaralkyl, alkoxyalkyl, carboxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, and haloalkyl; and M is selected from the group consisting of hydrogen, a monovalent metal, and a monovalent fractional part of a polyvalent metal, wherein said process is conducted under microwave irradiation at a frequency from 300 MHz to 30 GHz, and at a temperature of from about 120° C. to 300° C.
Abstract: A method for transferring amino acid into ketone acid (ester) may obtain ketone acid (ester) at low cost. The method uses sodium hypochlorous acid as oxidizing agent and proceeds oxidation reaction with amino acid or its derivatives so as to obtain ketone acid and its derivatives. The sodium hypochlorous acid is easily to get with low cost and the conditions of the reaction are mild so that the method meets the needs of the industry.
Abstract: A process for preparing 2-hydroxycarboxylic esters having a quaternary &bgr;-carbon atom by reaction of glycidyl esters with an organoaluminum reagent is described.
Abstract: The invention relates to a continuous process for enantioselective catalytic hydrogenation of an alpha ketocarbonyl compound such as alpha ketoesters and alpha ketolactones to produce an alpha hydroxy carbonyl compound.
Abstract: The present invention provides a process for preparing optically active &agr;-hydroxy acids and derivatives thereof by subjecting the alkylated 1,3-dioxolanones of formula (IV) wherein R1 and R2 are the same or different and are each independently H or C1-6 alkyl; R5 is H, C1-16 alkyl, or unsubstituted or substituted phenyl; and R6 is C1-8 alkyl, C2-7 alkenyl or unsubstituted or substituted benzyl, to either alcoholysis or hydrolysis, in which the alkylated 1,3-dioxolanones are obtained by using 10-camphorsulfonamide as a chiral auxiliary.
Type:
Grant
Filed:
October 8, 2002
Date of Patent:
October 28, 2003
Inventors:
Biing-Jiun Uang, Jia-Wen Chang, Der-Pin Jang
Abstract: The invention provides a process for the conversion of an extracted carboxylic acid to a non-ionized derivative thereof, comprising contacting a carboxylic acid containing aqueous solution with a water-insoluble amine solvent, to recover acid therefrom and to form an extract carrying amine-bound carboxylic acid, characterized in that said extract is contacted with a concentrated aqueous solution of said same acid of high concentration, whereby additional acid is transferred to said extract to form a loaded extract and said loaded extract is reacted to form a non-ionized derivative of said acid, by reactions known per se, whereby said acid is converted into a non-ionised derivative form and said amine solvent is liberated for recycling.
Abstract: Amidomethyl esters, carbonylmercaptomethyl esters, keto-containing esters, amidomethyl thioesters, amidomethyl amides, and methylene dithioesters are disclosed. The novel compounds have two carbonyl groups connected by a linking moiety having an oxygen, sulfur or nitrogen attached to a methylene group, to which is further attached a sulfur, nitrogen or CH2 group. Methods of treating illnesses and conditions, such as cancer, hemological disorders, inherited metabolic disorders and others, using these compounds are also disclosed.
Type:
Application
Filed:
October 29, 2002
Publication date:
September 11, 2003
Applicant:
Beacon Laboratories, Inc, a Delaware corporation
Inventors:
Hsuan-Yin Lan-Hargest, Norbert L. Wiech
Abstract: A high yield process for the production of methyl methacrylate or methacrylic acid and an apparatus for increasing the yield in a process for the production of methyl methacrylate or methacrylic acid are disclosed.
Type:
Grant
Filed:
July 29, 2002
Date of Patent:
August 26, 2003
Assignee:
Rohm and Haas Company
Inventors:
Chorng-Shyuan Tsay, Michael Stanley DeCourcy, I-Hwa Midey Chang-Mateu, Heather Granzin Thompson, Diana Elaine Chase
Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.
Type:
Grant
Filed:
November 8, 2001
Date of Patent:
August 19, 2003
Assignee:
WE-DEA Aktiengesellschaft für Mineraloel und
Chemie
Inventors:
Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
Abstract: A process for the preparation of hydroxy and amino compounds, in which, in a first step, an aldehyde, ketone or imine is reacted in a Reformatsky reaction with a reactive halogen compound and zinc, in carboxylic esters as solvents, the reactive halogen compound being brought into contact with the zinc at the same time as or after contact with the aldehyde, ketone or imine, and in a second step, the reaction product of the first step is hydrolyzed.
Abstract: Disclosed herein is a novel process for preparing 3-hydroxyesters, comprising: (a) reacting an epoxide derivative with carbon monoxide and alcohol in a solvent at a temperature of 30˜150° C. under a pressure of 50˜3000 psig by using a catalyst system consisting of a catalytic amount of a cobalt compound and optionally an effective amount of a promoter to produce a 3-hydroxyester or a derivative thereof; (b) separating the resulting product and the solvent from the cobalt compound and the promoter in a stripping column at a temperature of −30˜200° C. in an atmosphere of a stabilizing gas; and (c) recycling a part or all of the separated cobalt compound and promoter to the step (a) and repeating the steps (a) through (c).
Type:
Grant
Filed:
October 17, 2002
Date of Patent:
July 29, 2003
Assignee:
Davy Process Technology Ltd.
Inventors:
Byeong No Lee, Eun Joo Jang, Hyung Soo Cho, Byung Soon Chun
Abstract: Chiral diphosphines constituted by an aromatic pentatomic biheterocyclic system, suitable to act as chiral ligands, complexes between said diphosophines and transition metals, and their utilization as chiral catalysts in sterocontrolled reactions, such as diastereo- and enantioselective reduction reactions. Process for the preparation of said chiral diphosophines and process for the preparation of said complexes and for their utilization as chiral catalysts in sterocontrolled reactions.
Abstract: The invention relates to a novel process for preparing optically active trimethyllactic acid and/or its esters by catalytic hydrogenation of trimethylpyruvic acid and/or its esters in the presence of noble metal complex catalysts containing phosphorus ligands.
Abstract: A non-catalytic process for producing esters, the process comprising reacting an ammonium salt of a carboxylic acid with an alcohol and removing ammonia from the reaction mixture. Selectivities for the desired ester product can exceed 95 percent.
Type:
Grant
Filed:
February 22, 2002
Date of Patent:
June 24, 2003
Assignee:
The United States of America as represented by the United
States Department of Energy
Abstract: Disclosed herein is a novel process for preparing 3-hydroxyesters, comprising: (a) reacting an epoxide derivative with carbon monoxide and alcohol in a solvent at a temperature of 30˜150° C. under a pressure of 50˜3000 psig by using a catalyst system consisting of a catalytic amount of a cobalt compound and optionally an effective amount of a promoter to produce a 3-hydroxyester or a derivative thereof; (b) separating the resulting product and the solvent from the cobalt compound and the promoter in a stripping column at a temperature of −30˜200° C. in an atmosphere of a stabilizing gas; and (c) recycling a part or all of the separated cobalt compound and promoter to the step (a) and repeating the steps (a) through (c).
Type:
Application
Filed:
October 17, 2002
Publication date:
June 12, 2003
Inventors:
Byeong No Lee, Eun Joo Jang, Hyung Soo Cho, Byung Soon Chun
Abstract: Amidomethyl esters, carbonylmercaptomethyl esters, keto-containing esters, amidomethyl thioesters, amidomethyl amides, and methylene dithioesters are disclosed. The novel compounds have two carbonyl groups connected by a linking moiety having an oxygen, sulfur or nitrogen attached to a methylene group, to which is further attached a sulfur, nitrogen or CH2 group. Methods of treating illnesses and conditions, such as cancer, hemological disorders, inherited metabolic disorders and others, using these compounds are also disclosed.
Type:
Grant
Filed:
December 21, 2000
Date of Patent:
May 13, 2003
Assignee:
Beacon Laboratories, Inc.
Inventors:
Hsuan-Yin Lan-Hargest, Norbert L. Wiech
Abstract: A high yield process for the production of methyl methacrylate or methacrylic acid and an apparatus for increasing the yield in a process for the production of methyl methacrylate or methacrylic acid are disclosed.
Abstract: A process for the preparation of 5-(3,5-dimethylphenoxymethyl)-2-oxazolidinone, which includes:
a) reacting 3,5-dimethylphonel with epichlorohydrin to obtain a mixture of 1-(3,5-dimethylphenoxy)2,3-epoxy propane (1) and 1-(3,5-dimethylphenoxy)-3-chloro-2-propanol (2);
b) reacting the mixture of (1) and (2) obtained from step (a) with benzylamine to obtain a first compound;
c) reducing the first compound with hydrogen in presence of ammonia, to obtain a second compound; and
d) reacting the second compound with dimethylcarbonate in the presence of a strong base to obtain 5-(3,5-dimethlphenoxymethyl)-2-oxazolidinone.
Abstract: A process for preparing an 1,3-alkanediol through carbonylation of an epoxide derivative includes the steps of (a) reacting an epoxide derivative with alcohol and carbon monoxide in a solvent at a temperature from about 30 to about 150° C. and at a pressure from about 50 to about 3000 psig in the presence of a catalyst system including an effective amount of a cobalt catalyst and an effective amount of a promoter to afford a reaction mixture including a 3-hydroxyester or derivative thereof in an amount of from 2 to about 95% by weight, (b) separating the reaction product and solvent from the catalyst and promoter, (c) reacting said reaction product and solvent with hydrogen at a temperature from about 30 to about 350° C. and at a pressure from about 50 to about 5000 psig in the presence of a catalyst system for hydrogenation to prepare a hydrogenation product mixture including a 1,3-alkanediol, and (d) recovering the 1,3-alkanediol from the hydrogenation product mixture.
Abstract: This invention encompasses a process for making a compound of Formula A
These compounds are intermediates useful in the preparation of certain non-steroidal anti-inflammnatory agents.
Type:
Grant
Filed:
January 17, 2002
Date of Patent:
December 17, 2002
Assignee:
Merck & Co., Inc.
Inventors:
Cheng Yi Chen, Weirong Chen, Paul O'Shea, Lushi Tan, Richard Tillyer, Feng Xu, Philippe Dagneau
Abstract: A novel process in which an optically active alcohol compound having a desired absolute configuration and a high optical purity can be obtained by asymmetrically hydrogenating a &bgr;-keto acid compound through a simple operation. An optically active alcohol represented by general formula (III) as defined is obtained by asymmetrically hydrogenating a &bgr;-keto ester compound represented by general formula (I) as defined in the presence of at least one ruthenium complex having as a ligand an optically active tertiary diphosphine compound represented by general formula (II) as defined.
Abstract: Substituted alkylketo compounds of the formula
can be converted to the corresponding amino acid by a stereoselective enzymatic process. The resulting amino acid compounds can be employed as starting materials for pharmaceutically active compounds. This invention is directed to the substituted alkylketo compounds and their method of preparation.
Type:
Grant
Filed:
May 3, 2001
Date of Patent:
November 26, 2002
Assignee:
Bristol-Myers Squibb Co.
Inventors:
Ronald L. Hanson, Paul A. Jass, Wen-Sen Li, Ramesh Patel, Keith Ramig, John J. Venit
Abstract: Polyols which can be obtained by making epoxidized fatty acid esters of monofunctional C 1-8 alcohols react with aliphatic alcohols having a functionality ranging from 2-10. Fatty acid mixtures with mainly 18 carbon atoms represent the fatty acid component in the epoxidized fatty acid esters. The oleic acid content of the fatty acid mixtures is at least 80 wt %. The polyols are suitable for use in the production of isocyanate casting resins and coating compounds with enhanced colour stability.
Type:
Application
Filed:
May 11, 1999
Publication date:
October 31, 2002
Inventors:
ANDREAS HEIDBREDER, ROLAND GRUETZMACHER, ULRICH NAGORNY, ALFRED WESTFECHTEL
Abstract: A process for preparing a malonic acid monoester or &bgr;-ketoester from an epoxide includes the steps of reacting an epoxide with carbon monoxide and an alcohol in the presence of a catalytic amount of a cobalt compound and at least one promoter to produce a &bgr;-hydroxyester, separating the &bgr;-hydroxyester from the cobalt compound and the promoter, and oxidizing the &bgr;-hydroxyester to produce a malonic acid monoester or &bgr;-ketoester.
Type:
Grant
Filed:
June 20, 2001
Date of Patent:
October 15, 2002
Assignee:
Samsung Electronics Co., Ltd.
Inventors:
Byeong No Lee, In-Sun Jung, Eun Joo Jang
Abstract: The invention concerns novel chemical compounds, namely citronellyl lactate and dihydrocitronellyl lactate and their optically active forms. The invention also concerns the method for obtaining them. The invention further concerns their use in the field of perfumes.
Abstract: The invention provides a process for the production of a condensation product selected from the group consisting of an amide and an ester of a carboxylic acid from an organic compound selected from the group consisting of organic compounds carrying a hydroxyl group and organic compounds carrying an amine group and from a concentrated medium resulting from fermentation, said medium containing a salt of the acid, the salt being selected from the group consisting of a sodium salt, a calcium salt, and mixtures thereof and the medium being at a pH of at least the pKa of the acid, the process comprising reacting the medium with the organic compound and with CO2, whereby the condensation product and a salt selected from the group consisting of sodium carbonate, sodium bicarbonate, calcium carbonate, calcium bicarbonate, and mixtures thereof are formed; and, separating the condensation product from the reaction mixture formed in the previous step.
Abstract: The present invention relates to novel fatty acid analogous of the general forumla I: CH3—[CH2]m—[xi—CH2]n—COOR, as defined in the specification, which can be used for the treatment and/or prevention of obesity, fatty liver and hypertension. Further, the invention relates to a nutritional composition comprising such fatty acid analogues, and a method for reducing the total weight, or the amount of adipose tissue in an animal. The invention also relates to a method for improving the quality of product such as meat, milk and eggs.
Abstract: A process for the preparation of a 2-methyl-1,3-dicarboxylate by reaction of a 1,3-dicarboxylate with formaldehyde and hydrogen, where, based on 1 mol of dicarboxylate, from 1.0 to 2.0 mol of formaldehyde are used, and either the reaction mixture or 2-hydroxymethyl-2-methyl-1,3-dicarboxylate isolated therefrom as by-product are subjected to thermolysis at temperatures of from 50° C. to 300° C.
Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.
Type:
Grant
Filed:
January 25, 2000
Date of Patent:
April 30, 2002
Assignee:
RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
Inventors:
Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
Abstract: A carbonylation process, wherein formaldehyde or a derivative thereof is reacted with carbon monoxide in the presence of a catalyst composition including:
a) an acidic compound with pKa value below −1, and
b) a sulfone.
Type:
Grant
Filed:
December 18, 2000
Date of Patent:
April 23, 2002
Assignee:
Shell Oil Company
Inventors:
Eit Drent, Wilhelmus Petrus Mul, Bart Johan Ruisch
Abstract: Additives obtained from the catalytically induced esterification reaction of a mono- or polyhydroxy alkanol and at least one carboxylic acid employing a complexing agent selected from dicarboxylic acids or anhydrides thereof to substantially reduce the residual tin content and thermoplastic compositions and articles produced thereby.
Abstract: The invention relates to a novel process for preparing optically active trimethyllactic acid and/or its esters by catalytic hydrogenation of trimethylpyruvic acid and/or its esters in the presence of noble metal complex catalysts containing phosphorus ligands.
Abstract: A novel process in which an optically active alcohol compound having a desired absolute configuration and a high optical purity can be obtained by asymmetrically hydrogenating a &bgr;-keto acid compound through a simple operation. An optically active alcohol represented by general formula (III) as defined is obtained by asymmetrically hydrogenating a &bgr;-keto ester compound represented by general formula (I) as defined in the presence of at least one ruthenium complex having as a ligand an optically active tertiary diphosphine compound represented by general formula (II) as defined.
Abstract: Reactions of ring systems, such as aziridines, oxetanes and oxiranes with carboxylic acids, anhydrides, imides, lactones and carbonate esters are catalyzed by C3-C60, substituted or unsubstituted, straight or branched-chained, alkyl, aryl, or aralkyl carboxylate Cr+3 salts, preferably chromium +3 octoate. The catalysts also accelerate the reaction of hydroxy compounds with anhydrides, and of thiiranes with anhydrides. The catalysts selectively enhance the conversion of ring systems to form monomers, prepolymers, copolymers, functional end-group monomers, functional end-group prepolymers, and functional end-group polymers rather than forming homopolymers. By varying the catalyst concentration, molar ratios, and reaction temperatures, the reaction time required to form the desired product can be controlled.
Type:
Grant
Filed:
April 3, 2000
Date of Patent:
March 19, 2002
Assignee:
Dimension Technology Chemical Systems, Inc.
Abstract: The present invention provides a process for producing hydroxycarboxylic acid esters easily, further at a high reaction selectivity, by using an inexpensive catalyst. That is, the present invention provides a process for producing hydroxycarboxylic acid esters, which comprises hydrogenating dicarboxylic acid diesters having 3 to 20 carbon atoms in the dicarboxylic acid moiety in the presence of a copper catalyst comprising 1 to 40% by weight of copper as copper oxides.
Abstract: The present invention relates to a catalyst-free process for the conversion of commercial lactic acid to alkyl ester of carbon C1 to C8 which comprises simultaneous hydrolysis of dimers or highpolymers of lactic acid present in commercial lactic acid to free lactic acid and esterification of free lactic acid with an alcohol in the presence of water at a temperature in the range of 130-250° C. for 4-11 hrs at a pressure of 5-25 kg/cm2, to obtain desired esters.
Type:
Grant
Filed:
January 31, 2001
Date of Patent:
January 29, 2002
Assignee:
Council of Scientific & Industrial Research
Abstract: Compositions comprising ketone bodies and/or their metabolic precursors are provided that are suitable for administration to humans and animals and which have the properties of, inter alia, (i) increasing cardiac efficiency, particularly efficiency in use of glucose, (ii) for providing energy source, particularly in diabetes and insulin resistant states and (iii) treating disorders caused by damage to brain cells, particularly by retarding or preventing brain damage in memory associated brain areas such as found in Alzheimer's and similar conditions.
Abstract: Block copolymers containing a fluorinated hydrocarbon unit, a hydrocarbon unit, and a poly(oxyethylene) unit are useful in fluid formulations of pharmaceutical agents. A typical embodiment is:
C11H23—CONHC2H4NHCO—C8F16—CONHC2H4NHCOO—(C2H4O)34—H.
Type:
Grant
Filed:
August 5, 1999
Date of Patent:
November 13, 2001
Assignee:
Supratek Pharma, Inc.
Inventors:
Alexander V. Kabanov, Serguei V. Vinogradov
Abstract: There is herein disclosed a process for efficiently preparing, from an &agr;-hydroxycarboxylic amide and an alcohol in an industrially advantageous manner, an &agr;-hydroxycarboxylate which is useful as any of raw materials for solvents, food additives, perfumes, various organic medicines and the like.
According to the present invention, there is provided a process for preparing an &agr;-hydroxycarboxylate which comprises the step of reacting an &agr;-hydroxycarboxylic amide and an alcohol in the presence of a catalyst in a liquid phase, while an ammonia concentration in a reaction solution is maintained at 0.1% by weight or less by discharging generated ammonia as a gas into a gaseous phase.
Abstract: A process has been provided to produce semi synthetic statins, as for instance simvastatin with a high yield, for another statin, preferably a naturally occurring statin, as for instance lovastatin. Also a number of novel intermediate compounds, prepared during said process, has been provided.
Type:
Grant
Filed:
January 5, 2000
Date of Patent:
September 25, 2001
Assignee:
Plus Chemicals, B.V.
Inventors:
Ton Rene Vries, Hans Wijnberg, Wijnand Sjourd Faber, Venetka Ivanova Kalkman-Agayn, Mieke Ivanova Sibeyn