Purification Or Recovery Patents (Class 564/437)
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Patent number: 5196585Abstract: The present invention is directed toward a process of treating crude dinitroaniline with an aqueous sulfite solution as a method of stabilizing the herbicide against formation of nitrosamines and of reducing impurities therein.Type: GrantFiled: October 2, 1990Date of Patent: March 23, 1993Assignee: DowElancoInventor: David D. Wirth
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Patent number: 5108890Abstract: The present invention provides compounds of the general formula: ##STR1## wherein R.sup.1 is an amino acid residue or a residue of an oligopeptide in which the amino groups are optionally substituted by protective groups, R.sup.2 and R.sup.3, which are the same or different, are hydrogen atoms, a lower alkyl, lower alkoxy, carboxyl or lower alkoxycarbonyl radicals or carboxamido groups optionally substituted by lower alkyl or, if R.sup.2 and R.sup.3 are adjacent, can represent a --CH.dbd.CH--CH.dbd.CH-- radical, Z is a conjugated-through positively charged, bicyclic heterocyclic system and X is an anion of an organic or inorganic acid. The present invention also provides processes for the preparation of these compounds and diagnostic agents containing them for the determination of peptide bond-cleaving enzymes.Type: GrantFiled: March 31, 1988Date of Patent: April 28, 1992Assignee: Boehringer Mannheim GmbHInventors: Hans Wielinger, Gerd Zimmermann
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Patent number: 5107024Abstract: Selective removal of primary amines from technical grade diphenylamine by contacting a solvent solution of said diphenylamine with a cationic exchange resin having sulfonic acid group functionality in the presence of up to about 3 percent water.Type: GrantFiled: May 22, 1991Date of Patent: April 21, 1992Assignee: Atochem Agri, S.A.Inventors: Pieter Kool, Eliezer L. Sigall, Samuel Meghir
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Patent number: 5091572Abstract: Liquid amine terminated polyamide addition products having an average molecular weight of about 3,000 to about 10,000 are prepared by the non-catalytic reaction of a dicarboxylic acid having a molecular weight within the range of about 130 to about 700 with a higher molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 1,500 to about 6,000 and with a lower molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 200 to about 700, the reaction conditions including a temperature within the range of about 150.degree. to about 280.degree. C., a pressure of about 0.1 to 20 atmospheres and a reaction time of about 2 to about 5 hours.Type: GrantFiled: December 11, 1989Date of Patent: February 25, 1992Assignee: Texaco Chemical CompanyInventors: George P. Speranza, Wei-Yang Su
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Patent number: 5068440Abstract: A process for the preparation of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate, a non-hygroscopic material which can be used as a pharmaceutical in the treatment of depression.Type: GrantFiled: January 19, 1990Date of Patent: November 26, 1991Assignee: Boots Company, PLCInventors: James E. Jeffery, Derek Whybrow
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Patent number: 5068435Abstract: This invention relates to a process for producing ring alkylated aromatic amines. In the process an aromatic amine is reacted with an olefin using gamma alumina as a catalyst. Under the conditions of the process the catalyst is extremely active and with amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved.The catalyst is also effective for producing unsymmetrical disubstituted alkyl aromatic amines, e.g., ethyl or propyl toluidine where one ortho position is substituted with a methyl group and the other substituted with an ethyl or propyl group.Type: GrantFiled: March 25, 1988Date of Patent: November 26, 1991Assignee: Air Products and Chemicals, Inc.Inventors: William F. Burgoyne, Jr., Dale D. Dixon
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Patent number: 4978430Abstract: An improved method for dehydration and concentration of an aqueous solution containing an organic compound is disclosed. The solution is evaporated to produce a gaseous mixture comprising an organic compound vapor and a water vapor. The water vapor is selectively removed from the gaseous mixture by permeation through an aromatic polyimide gas separation membrane while the gaseous mixture being kept in contact with a surface on one side of the gas separation membrane at a temperature of 70.degree. C. or higher to obtain a gaseous mixture comprising the organic compound vapor and a reduced amount of a water vapor.Type: GrantFiled: July 24, 1989Date of Patent: December 18, 1990Assignee: UBE Industries, Ltd.Inventors: Kanji Nakagawa, Yoshio Asakura, Shigeru Yamamoto, Kohei Ninomiya, Masayuki Kinouchi
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Patent number: 4973759Abstract: Alkylated aromatic amines can be isolated from crude catalyst-containing mixtures of these with olefins by a procedure in which in general equivalent amounts of an inorganic base and water are added to the alkylation mixture, the catalyst is hydrolysed, the water present in the reaction mixture after the hydrolysis is removed by distillation and the solid catalyst residue is separated off. The catalyst-free alkylation mixture which remains is then fed to customary further working up.Type: GrantFiled: September 20, 1989Date of Patent: November 27, 1990Assignee: Bayer AktiengesellschaftInventors: Alfons Klein, Helmut Fiege
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Patent number: 4970343Abstract: A one-step process for the preparation of nitrosamine-free dinitroaniline herbicides which involves contacting the crude dinitroaniline herbicide in the liquid state, after removal of excess amine, with an effective quantity of a hydrobromide salt of a p-amino benzoate ester, optionally in the presence of such an ester, passing a gaseous stream of air therethrough or applying a reduced pressure so as to essentially remove water present, resulting in an essentially nitrosamine-free product.Type: GrantFiled: June 15, 1987Date of Patent: November 13, 1990Assignee: Agan Chemical Manufacturers Ltd.Inventors: Michael Pikarski, Edmund Dykman
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Patent number: 4967004Abstract: A process for producing an N,N-diethylaminophenol is disclosed, comprising subjecting an aminophenol to reductive alkylation with acetaldehyde in the presence of a solvent, a catalyst, and hydrogen is disclosed, in which the reaction mixture from which the catalyst has been removed is subjected to distillation while maintaining the temperature of the bottom at 160.degree. C. or lower to substantially remove the unreacted acetaldehyde and the solvent, the residual bottom is distilled while maintaining the temperature of the bottom at 200.degree. C. or lower to recover a crude N,N-diethylaminophenol as a distillate, and the recovered crude N,N-diethylaminophenol is contacted with a solvent to which at least one of acid sulfites and dithionites has been added, said solvent being substantially incompatible with the N,N-diethylaminophenol, in an inert gas atmosphere, followed by precipitating and recovering the N,N-diethylaminophenol by cooling.Type: GrantFiled: April 8, 1988Date of Patent: October 30, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Maki, Shigeru Sasaki
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Patent number: 4918232Abstract: A process for separating from each other aniline and aniline derivatives having different numbers of C atoms bound to the N atoms is disclosed herein, this process being characterized in that a mixture of the substances mentioned is treated in liquid phase with zeolites of the faujasite type at a temperature from 0.degree. C. to 190.degree. C.Type: GrantFiled: June 29, 1988Date of Patent: April 17, 1990Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Michael Hullmann, Lothar Puppe
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Patent number: 4876388Abstract: Crude trifluralin is subjected to a purification treatment to remove nitrosamines therefrom and to improve its content of the active principle.The treatment consists of passing through the trifluralin, kept in the liquid state at a temperature of from 50.degree. to 110.degree. C., a quantity of from 1 to 4 times its weight of saturated steam at 105.degree. to 110.degree. C.The nitrosamine content of the treated trifluraline is less than 1 ppm.Type: GrantFiled: May 20, 1988Date of Patent: October 24, 1989Assignee: I.PI.CI. S.p.A.Inventor: Guido Ravetta
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Patent number: 4874895Abstract: The level of the nitrosamines which may be present in the unrefined trifluralin is reduced to a value below 0.5 ppm, by treating the unrefined trifluralin under agitation, at a temperature from 60.degree. to 90.degree. C., for a time between 10 minutes and 4 hours, with an aqueous solution containing from 15 to 50% by weight of hydrobromic acid in a ratio of 0.2 to 0.8 liters per kilogram of unrefined trifluralin, said aqueous solution of hydrobromic acid being added with an amount of sulfamic acid from 0.1 to 3 g per liter of solution and with an amount of bisulfite or an alkali metal corresponding to a content of sulphur dioxide from 0.3 to 1.2 g per liter of said hydrobromic acid aqueous solution.The so obtained refined trifluralin has a content of nitrosamines which is lower than 0.1 ppm.Type: GrantFiled: February 17, 1989Date of Patent: October 17, 1989Assignee: Finchimica S.p.A.Inventor: Donadello Graziello
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Patent number: 4870209Abstract: A process for the purification of crude 4-aminophenol which was prepared by the catalytic hydrogenation of nitrobenzene in aqueous sulfuric acid is described involving: adjusting the pH of an aqueous solution of crude 4-aminophenol to pH 4.0-5.0 at a temperature between 75.degree. C. and 85.degree. C.; mixing the aforesaid solution with toluene as the solvent, in order to extract various impurities and the dissolved nitrobenzene starting material; adjusting the pH of the resultant solution as required to maintain it at pH 4.0-5.0; allowing the resultant mixture to settle thereby forming a top organic layer and a bottom aqueous raffinate layer which raffinate contains 4-aminophenol and the by-product material, ortho-aminophenol; separating the two layers and repeatedly extracting the raffinate layer which toluene at pH 4.0-5.0 at a temperature of 75.degree.-85.degree. C.Type: GrantFiled: April 29, 1987Date of Patent: September 26, 1989Assignee: Noramco, Inc.Inventors: James T. F. Kao, Dwight E. Raff, II
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Process for producing higher molecular weight amino compounds having reduced monomeric amine content
Patent number: 4855504Abstract: High molecular weight amines having reduced low molecular weight amine contents are obtained by reacting a mixture of (1) a high molecular weight amine and (2) a low molecular weight amine with (3) an isocyanate in quantities such that from 0.5 to 10 equivalents of isocyanate are present for each equivalent of low molecular weight amine. The product of high molecular weight amines is particularly useful in the production of isocyanate addition products such as polyurethane plastics and foams.Type: GrantFiled: September 23, 1985Date of Patent: August 8, 1989Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Ernst Grigat, Gerhard Grogler, Heinrich Hess, Richard Kopp -
Patent number: 4855053Abstract: Process for extracting organic compounds which are present in water in the form of solutions or suspensions by a liquid carboxylic acid which is immiscible with water. Branched or unbranched linear acids such as n-heptanoic, n-octanoic, or 2-ethylhexanoic acids make it possible to quantitatively extract compounds such as phenols, amines or amino acids from such aqueous solutions, thereby rendering the process useful for the purification of industrial wastewaters.Type: GrantFiled: December 18, 1986Date of Patent: August 8, 1989Assignee: AtochemInventors: Charles Benedetti, Claude Gluntz, Robert Pascal, Michel Stefanini
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Patent number: 4825002Abstract: A Lewis acid contaminant is removed from a (hydrocarbylthio)aromatic amine by mixing a solid alkali metal hydroxide with a solution of the Lewis acid in the amine, preferably at about 110.degree.-120.degree. C., and then filtering the solids from the mixture.Type: GrantFiled: November 2, 1987Date of Patent: April 25, 1989Assignee: Ethyl CorporationInventor: Robert L. Davis
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Patent number: 4780540Abstract: Tar-like residues from the preparation of 2-mercaptobenzothiazole can be used by heating them at temperatures above 200.degree. C. for at least 1 hour and separating off the aniline and benzothiazole thereby formed.Type: GrantFiled: February 3, 1987Date of Patent: October 25, 1988Assignee: Bayer AktiengesellschaftInventors: Gabriel Denecker, Guido Lahousse, Henri Vandebroek, Pol Balmelis
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Patent number: 4727191Abstract: A (hydrocarbylthio)aromatic amine, such as a methylthiosubstituted toluenediamine, is separated from corresponding aromatic amines containing fewer hydrocarbylthio groups by washing an organic solution of the amine mixture with a dilute aqueous acid having a pKa value below 7 to extract at least a portion of the corresponding aromatic amines.Type: GrantFiled: July 10, 1986Date of Patent: February 23, 1988Assignee: Ethyl CorporationInventor: Christopher J. Nalepa
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Patent number: 4727161Abstract: A process for producing an indole which comprises reacting an aniline and a diol in the presence of a catalyst to produce a reaction mixture containing the indole, unreacted aniline and by-products, condensing the reaction mixture to obtain a liquid reaction product, recovering the unreacted aniline from the liquid reaction product, reducing the contents of specified by-products in the recovered aniline below specified levels and reutilizing the resulting recovered aniline. To reduce the contents of the specified by-products in the recovered aniline below specified levels, it is preferred to subject the liquid reaction product or an aniline fraction separated therefrom to a heat-treatment and then to distillation. In the above manner, the recovered aniline can be reutilized in the reaction without causing the activity of the catalyst to deteriorate.Type: GrantFiled: November 15, 1985Date of Patent: February 23, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Atsuyoshi Yamauchi, Seiya Iguchi, Yuzo Ono, Hiroshii Kimura, Satoshi Morita
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Patent number: 4720326Abstract: An amine is separated from an aqueous solution of amine and volatile organic compounds by distillation in a column. The vapors generated during distillation are condensed. The condensed vapors are then passed into a separating device in which the volatile organic compounds are removed. The liquid remaining in the separating device is then fed to the head of the distillation column. Water is removed from the column in a sidestream and diamine is the residue. This process is particularly effective in recovering aromatic diamines from solutions which accumulate during hydrogenation of dinitro aromatic compounds.Type: GrantFiled: February 13, 1987Date of Patent: January 19, 1988Assignee: Bayer AktiengesellschaftInventors: Heiko Beckhaus, Harro Witt, Dieter Becher, Hermann Dallmeyer, Uwe J. Zarnack
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Patent number: 4677229Abstract: Process for the production of a water-insoluble nitrogeneous organic base, from an aqueous solution of alkali metal bicarbonate and the base hydrochloride, according to which the solution (11) is treated with a complement of the base hydrochloride (12), and the resultant liquid (18) is treated with a basic agent (30) capable of decomposing the hydrochloride. The invention is applied to the regeneration of the amine in the process for the manufacture of sodium bicarbonate by the amines method.Type: GrantFiled: July 15, 1985Date of Patent: June 30, 1987Assignee: Solvay & Cie. (Societe Anonyme)Inventors: Leon Ninane, Claude Breton
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Patent number: 4675445Abstract: A process for eliminating N-nitrosamines, particularly N,N-dialkyl-N-nitrosamines and N-alkyl-N-aryl-N-nitrosamines from N-nitrosamine containing compositions through the addition of organic carboxylic acid halides. The process eliminates N-nitroso compounds without rearrangement to C-nitroso compounds.Type: GrantFiled: November 12, 1985Date of Patent: June 23, 1987Assignee: BASF CorporationInventors: Pauls Davis, Donald C. Mente
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Patent number: 4638090Abstract: Processes for the preparation of nitrosamine-free N,N-disubstituted nitroaromatic amines by degradation of their nitrosamine components formed during their preparation, and by stabilization of the products against renewed formation of nitrosamines, by treating the amines in liquid or molten form with a sulfonic acid, where necessary in the presence of inert organic solvents or diluents.Type: GrantFiled: December 12, 1984Date of Patent: January 20, 1987Assignee: Hoechst AktiengesellschatInventors: Rudolf Heinrich, Konrad Albrecht
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Patent number: 4559182Abstract: A method for removing residual cresidine from impure p-cresidine sulfonic acid which impure p-cresidine sulfonic acid contains from above two parts per billion to about 1500 parts per million of cresidine. The method comprises contacting an aqueous solution of the p-cresidine sulfonic acid with a sufficient quantity of particles of a crosslinked lipophilic porous resin for a sufficient time to reduce the concentration of p-cresidine in the cresidine sulfonic acid to less than 2 parts per billion.Type: GrantFiled: November 9, 1981Date of Patent: December 17, 1985Assignee: Buffalo Color CorporationInventor: Henry M. Grotta
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Patent number: 4552958Abstract: A method for the separation of primary amines such as bis-(2-aminoethyl)ether from tertiary amines such as N-(2-methoxyethyl)morpholine which have close boiling points via extraction using a non-polar hydrocarbon solvent and water is described. The water may be added to a stream containing both bis-(2-aminoethyl)ether and N-(2-methoxyethyl)morpholine before extraction with the non-polar hydrocarbon is performed. The N-(2-methoxyethyl)morpholine is selectively removed by the hydrocarbon.Type: GrantFiled: February 17, 1984Date of Patent: November 12, 1985Assignee: Texaco Inc.Inventors: Simon P. Burns, John M. Walton, Edward E. McEntire
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Patent number: 4552957Abstract: A method for the separation of primary amines such as bis-(2-aminoethyl)ether from tertiary amines such as N-(2-methoxyethyl)morpholine which have close boiling points via extraction using a non-polar hydrocarbon solvent is described. Alternatively, a polyhydroxylic compound or a mixture of such compounds may be added to a stream containing both bis-(2-aminoethyl)ether and N-(2-methoxyethyl)morpholine before extraction with the non-polar hydrocarbon is performed. The N-(2-methoxyethyl)morpholine is selectively removed by the hydrocarbon.Type: GrantFiled: February 17, 1984Date of Patent: November 12, 1985Assignee: Texaco Inc.Inventor: Edward E. McEntire
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Patent number: 4540817Abstract: A process for the preparation of 5-amino-2,4-dimethylacetanilide by reduction of 5-nitro-2,4-dimethylacetanilide with hydrogen is disclosed characterized in that a crude mixture containing 5-nitro-2,4-dimethylacetanilide in admixture with at least one of its position isomers is hydrogenated in a water-miscible organic solvent which optionally contains water. The 5-amino-2,4-dimethylacetanilide is separated off from the reaction mixture by means of crystallization employing a mixture of water-miscible organic solvent and water.Type: GrantFiled: July 25, 1983Date of Patent: September 10, 1985Assignee: Bayer AktiengesellschaftInventors: Horst Behre, Heinz U. Blank, Alfred Seyberlich, Ferdinand Hagedorn
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Patent number: 4537992Abstract: A method for removal of nitrosoamine impurities from herbicides comprising contacting a nitrosoamine containing herbicide homogeneously with 0.001% to 1.0% of a compound having the formula: ##STR1## where X equals chlorine or bromine,R.sup.1 equals lower alkyl, anda equals zero or 1; provided that when a equals 1, then:R equals X.sub.n H.sub.(3-n) C(CH.sub.2).sub.p --, or ##STR2## or R.sup.2 COX, where R.sup.2 is selected from alkylene, alkenylene, alkynylene groups having 1 to 5 carbon atoms,n equals 1 to 3, andp equals zero, 1 or 2; and provided that when a equals zero, then:R equals aminophenyl,for a sufficient length of time to remove at least a substantial amount of the nitrosoamine.Type: GrantFiled: February 9, 1984Date of Patent: August 27, 1985Assignee: Agan Chemical Manufacturers, Ltd.Inventors: Michael Pikarski, Julian Gabe, Edmund Dykman
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Patent number: 4514574Abstract: Separate isomers via supercritical gas extraction.Type: GrantFiled: January 9, 1984Date of Patent: April 30, 1985Assignee: The Dow Chemical CompanyInventors: Kimio Inoue, Gale G. Hoyer, Stanley I. Bates
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Patent number: 4507475Abstract: A process for purifying crude polyether polyols which are prepared by anionic polymerization of alkylene oxides in the presence of basic catalysts. The polyols are mixed with water and ortho-phosphoric acid in certain quantity ratios, an adsorption agent is incorporated in the reaction mixture, the mixture is filtered and the water is removed from the polyether polyol by distillation.Type: GrantFiled: July 22, 1983Date of Patent: March 26, 1985Assignee: BASF AktiengesellschaftInventors: Wolfgang Straehle, Raymond Denni, Matthias Marx
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Patent number: 4504663Abstract: The present invention concerns novel heterocyclic aminoalcoyl derivatives having the formula: ##STR1## wherein n=1, 2 or 3; A represents a nitrogen atom or the CH group, X=CH.sub.2 or CH.sub.2 O; R represents a phenyl nucleus possibly substituted; NR.sub.1 R.sub.2 =amino, methylamino, N,N-dialkylamino or an heterocyclic radical; and R.sub.3 =H, halogen, alkyl, alkyloxy or methoxy.These derivatives are useful as drugs, especially as analgesics and antidepressants.Type: GrantFiled: November 15, 1983Date of Patent: March 12, 1985Assignee: Delalande S.A.Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
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Patent number: 4454347Abstract: Crystalline 5(6)-amino-1-(4-aminophenyl)-1,3,3-trimethylindane is made by crystallizing the diamino reaction mass from a toluene/heptane solution. The material has been previously purified through a combination of acetic acid washing and treatment with acidic clay. The diamino material, also known as DAPI, is a potential stabilizer, curing agent, and one of the monomers used to produce a polyimide resin.Type: GrantFiled: February 11, 1983Date of Patent: June 12, 1984Assignee: Ciba-Geigy CorporationInventors: Marc E. Parham, Stephen A. Spearman, Gleason O. Cookson
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Patent number: 4452994Abstract: An improved process for isolating organic compounds from crude product or reaction mixtures by dissolving said crude product or reaction mixture in a suitable solvent, contacting the resulting solution with a lithium salt to form a solid metal salt complex, separating, and thereafter recovering a pure product by decomposing the lithium salt complex.Type: GrantFiled: March 2, 1981Date of Patent: June 5, 1984Assignee: G. D. Searle & Co.Inventors: John B. Hill, Robert A. Erickson
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Patent number: 4440953Abstract: The purification of N-substituted aminobenzaldehydes, such as p-dimethylaminobenzaldehyde, is facilitated via the use of sequential suspension, acidification, solids removal, neutralization and product recovery steps.Type: GrantFiled: April 28, 1983Date of Patent: April 3, 1984Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4433168Abstract: Crude 3,4,3',4'-tetraaminodiphenyl (TAD) prepared by ammonolysis of 3,3'-dichlorobenzidine in the presence of mainly Cu catalysts is purified by a process in which(a) after its isolation from the preparation process crude TAD is treated with an aqueous NH.sub.3 solution and, if desired, TAD thus treated is then(b) dissolved and reprecipitated in water in the presence of adsorbents and also of a water-soluble reducing agent.Compared with relevant processes of the state of the art, the process produces a higher yield of pure TAD and it is also simpler to carry out.Type: GrantFiled: March 22, 1982Date of Patent: February 21, 1984Assignee: Hoechst AGInventors: Hans Schubert, Konrad Baessler
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Patent number: 4431851Abstract: The present invention concerns compounds of the formula ##STR1## wherein n=1, 2 or 3; and R' represents phenyl or orthofluorophenyl. Said compounds are used as intermediates in the preparation of heterocyclic aminoalkyl derivatives which are useful as analgesics and antidepressants.Type: GrantFiled: March 8, 1983Date of Patent: February 14, 1984Assignee: Delalande S.A.Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
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Patent number: 4400537Abstract: A process for the preparation of 1,4-phenylenediamine from 1,4-dihydroxybenzene at a temperature within the range of from about 300.degree. C. to 450.degree. C. and a pressure of from atmospheric to 3000 psig in the presence of an aminating agent, an inert hydrocarbon and an acidic alumina catalyst. p-Aminophenol can be aminated to 1,4-phenylenediamine with the same process.Type: GrantFiled: April 19, 1982Date of Patent: August 23, 1983Assignee: Standard Oil Company (Indiana)Inventor: Thomas A. Weil
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Patent number: 4399307Abstract: The distillation of 2,2'bis(4-aminocyclohexyl)propane to yield high purity product is effectively carried out using high boiling organic solvents.Type: GrantFiled: March 11, 1982Date of Patent: August 16, 1983Assignee: Phillips Petroleum CompanyInventor: Tod K. Shioyama
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Patent number: 4381408Abstract: A method and apparatus are disclosed for extracting amine compounds from air samples without loss due to formation of nitrosamine artifacts. The apparatus includes a cartridge having a separation zone between a first port and a second port. The separation zone contains an air pervious packing of a granular, solid phase amine complexing agent. The method includes a first step of driving an air sample through the separation zone of the cartridge from the first port to the second port, and a second step of driving an eluent through the separation zone from the second port to the first port, or backflushing the cartridge. To extract amine compounds, the eluent is a solvent for the amine complexing agent in the separation zone of the cartridge. The method may contain the further step of determining the amine compound concentration of at least a portion of the eluate which passes from the separation zone following the second step of the method.Type: GrantFiled: December 1, 1980Date of Patent: April 26, 1983Assignee: Thermo Electron CorporationInventors: David P. Rounbehler, John W. Reisch
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Patent number: 4376216Abstract: A new process for the purification of photographic developer compounds using an anionic surfactant wherein unwanted impurities are removed either by being precipitated or dissolved.In this process the developer substance is freed from difficult to remove impurities.Type: GrantFiled: August 3, 1981Date of Patent: March 8, 1983Assignee: Agfa-Gevaert AGInventor: Helmut Haseler
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Patent number: 4351958Abstract: An orthoalkylated aromatic amine is produced at a high selectivity from the reaction of an aromatic amine having at least one hydrogen atom at the ortho-positions and a primary or secondary alcohol under heating in the presence of a catalyst containing, as a main constituent, iron oxides.Type: GrantFiled: August 28, 1981Date of Patent: September 28, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Kazunori Takahata, Katsuo Taniguchi
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Patent number: 4347381Abstract: The pink color content often produced in products such as amine salts, amine oxides, betaines, quaternary ammonium compounds or other compounds derived from long chain alkyl amines is eliminated by treating the products with trace amounts of a bleaching agent. Heating of the treated amine at relatively low temperatures for a short period of time enhances the effectiveness of the bleaching agent. Long chain alkyl amines having a pink color may be similarly treated.Type: GrantFiled: January 24, 1978Date of Patent: August 31, 1982Assignee: Ethyl CorporationInventor: Melvin E. Tuvell
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Patent number: 4340757Abstract: A process for the preparation of 2,6-dialkylaniline which comprises the reaction of 1,3-dialkyl-5-tertiary-butylbenzene with molecular bromine to form 2-bromo-1,3-dialkyl-5-tertiary-butylbenzene, which is subsequently reacted with 1,3-dialkylbenzene in the presence of hydrogen fluoride to form a mixture of 2-bromo-1,3-dialkylbenzene and 1,3-dialkyl-5-tertiary-butylbenzene, which is then reacted with ammonia in the presence of a catalytic amount of cuprous halide.Type: GrantFiled: July 6, 1981Date of Patent: July 20, 1982Assignee: Chevron Research CompanyInventor: Shigeto Suzuki
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Patent number: 4340758Abstract: A process for the preparation of 2,6-dialkylaniline which comprises the reaction of 1,3-dialkylbenzene with isobutene in the presence of a hydrogen fluoride catalyst to form 1,3-dialkyl-5-tertiary-butylbenzene, which is subsequently nitrated in the presence of a soluble mercuric salt catalyst to form 2-nitro-1,3-dialkyl-5-tertiary-butylbenzene, which is then catalytically hydrogenated to give 2,6-dialkyl-4-tertiary-butylaniline, followed by pyrolysis in the presence of a heterogeneous acidic catalyst.Type: GrantFiled: July 6, 1981Date of Patent: July 20, 1982Assignee: Chevron Research CompanyInventors: Seymour J. Lapporte, David M. Marquis
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Patent number: 4335260Abstract: N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline ("Trifluralin") with a low content in nitrosamines (less than 1 ppm) is prepared by reacting 4-trifluoro-2,6-dinitro-chlorobenzene with di-n-propylamine under the following critical conditions:feeding to the chlorobenzoderivative the di-n-propylamine containing an alkali metal hydroxide or an alkaline carbonate so that the pH value of the reaction mass is comprised between 7 and 7.5;regulating the temperature of the reaction mass so that it does not exceed 70.degree. C.; andoperating in the presence of at least 50% by weight of water in the reaction mass.Type: GrantFiled: May 14, 1981Date of Patent: June 15, 1982Assignee: Montedison S.p.A.Inventors: Mario Bornengo, Sergio Bacciarelli
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Patent number: 4331817Abstract: A process for the preparation of a 4-arylthioaniline from the corresponding 4-unsubstituted aniline which comprises reacting the latter with an alkali metal thiocyanate in the presence of halogen to provide the 4-thiocyanoaniline, reacting it with an alkali metal sulfide to convert the thiocyano moiety to an alkali metal mercaptide group followed by heating with cuprous oxide then with an aryl halide to form the desired product.Type: GrantFiled: January 16, 1981Date of Patent: May 25, 1982Assignee: Minnesota Mining and Manufacturing Co.Inventor: James R. Throckmorton
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Patent number: 4329501Abstract: The conversion of alkyl diaminobenzenes to the alkyl amino benzenes is carried out by contacting the alkyl diamino benzene with hydrogen in the presence of a nonsupported cobalt catalyst. Optionally, the reaction is carried out in the presence of water so that the water insoluble product formed can be separated from the water soluble reactants and by-products.Type: GrantFiled: October 9, 1980Date of Patent: May 11, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Barton Milligan, Roland E. Grandin
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Patent number: 4328369Abstract: 2,6-dinitro-N-alkyl-anilines are prepared by continuously delivering a 2,6-dinitro-chlorobenzene, a dialkylamine, an inorganic base and water to a tubular reaction zone and operating in said reaction zone under turbulent conditions, at a temperature not exceeding 150.degree. C., for a short reaction time and with substantially complete conversion of the chlorobenzene.Type: GrantFiled: January 14, 1981Date of Patent: May 4, 1982Assignee: Rumianca S.p.A.Inventors: Luciano Baldi, Franco Collecchia, Vittorio Messori
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Patent number: H214Abstract: Substituted 1,1-difluoro(mono- or dihalo)ethoxybenzeneamines prepared by the reaction of a 1,1-difluoro(mono- or dihalo)ethylene and a substituted hydroxybenzeneamine in the presence of an alkali or alkaline earth metal hydroxide and a polar, aprotic solvent are isolated from the reaction mixture by a two stage distillation without prior dilution with water or other means of removal or neutralization of the alkali or alkaline earth metal hydroxides present. The products are useful intermediates in the preparation of insecticides and herbicides.Type: GrantFiled: July 19, 1985Date of Patent: February 3, 1987Inventor: John C. Little