Purification Or Recovery Patents (Class 564/437)
  • Patent number: 5196585
    Abstract: 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: Grant
    Filed: October 2, 1990
    Date of Patent: March 23, 1993
    Assignee: DowElanco
    Inventor: David D. Wirth
  • Patent number: 5108890
    Abstract: 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: Grant
    Filed: March 31, 1988
    Date of Patent: April 28, 1992
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans Wielinger, Gerd Zimmermann
  • Patent number: 5107024
    Abstract: 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: Grant
    Filed: May 22, 1991
    Date of Patent: April 21, 1992
    Assignee: Atochem Agri, S.A.
    Inventors: Pieter Kool, Eliezer L. Sigall, Samuel Meghir
  • Patent number: 5091572
    Abstract: 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: Grant
    Filed: December 11, 1989
    Date of Patent: February 25, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Wei-Yang Su
  • Patent number: 5068440
    Abstract: 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: Grant
    Filed: January 19, 1990
    Date of Patent: November 26, 1991
    Assignee: Boots Company, PLC
    Inventors: James E. Jeffery, Derek Whybrow
  • Patent number: 5068435
    Abstract: 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: Grant
    Filed: March 25, 1988
    Date of Patent: November 26, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Dale D. Dixon
  • Patent number: 4978430
    Abstract: 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: Grant
    Filed: July 24, 1989
    Date of Patent: December 18, 1990
    Assignee: UBE Industries, Ltd.
    Inventors: Kanji Nakagawa, Yoshio Asakura, Shigeru Yamamoto, Kohei Ninomiya, Masayuki Kinouchi
  • Patent number: 4973759
    Abstract: 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: Grant
    Filed: September 20, 1989
    Date of Patent: November 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alfons Klein, Helmut Fiege
  • Patent number: 4970343
    Abstract: 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: Grant
    Filed: June 15, 1987
    Date of Patent: November 13, 1990
    Assignee: Agan Chemical Manufacturers Ltd.
    Inventors: Michael Pikarski, Edmund Dykman
  • Patent number: 4967004
    Abstract: 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: Grant
    Filed: April 8, 1988
    Date of Patent: October 30, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Maki, Shigeru Sasaki
  • Patent number: 4918232
    Abstract: 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: Grant
    Filed: June 29, 1988
    Date of Patent: April 17, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Michael Hullmann, Lothar Puppe
  • Patent number: 4876388
    Abstract: 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: Grant
    Filed: May 20, 1988
    Date of Patent: October 24, 1989
    Assignee: I.PI.CI. S.p.A.
    Inventor: Guido Ravetta
  • Patent number: 4874895
    Abstract: 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: Grant
    Filed: February 17, 1989
    Date of Patent: October 17, 1989
    Assignee: Finchimica S.p.A.
    Inventor: Donadello Graziello
  • Patent number: 4870209
    Abstract: 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: Grant
    Filed: April 29, 1987
    Date of Patent: September 26, 1989
    Assignee: Noramco, Inc.
    Inventors: James T. F. Kao, Dwight E. Raff, II
  • Patent number: 4855504
    Abstract: 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: Grant
    Filed: September 23, 1985
    Date of Patent: August 8, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Ernst Grigat, Gerhard Grogler, Heinrich Hess, Richard Kopp
  • Patent number: 4855053
    Abstract: 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: Grant
    Filed: December 18, 1986
    Date of Patent: August 8, 1989
    Assignee: Atochem
    Inventors: Charles Benedetti, Claude Gluntz, Robert Pascal, Michel Stefanini
  • Patent number: 4825002
    Abstract: 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: Grant
    Filed: November 2, 1987
    Date of Patent: April 25, 1989
    Assignee: Ethyl Corporation
    Inventor: Robert L. Davis
  • Patent number: 4780540
    Abstract: 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: Grant
    Filed: February 3, 1987
    Date of Patent: October 25, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gabriel Denecker, Guido Lahousse, Henri Vandebroek, Pol Balmelis
  • Patent number: 4727191
    Abstract: 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: Grant
    Filed: July 10, 1986
    Date of Patent: February 23, 1988
    Assignee: Ethyl Corporation
    Inventor: Christopher J. Nalepa
  • Patent number: 4727161
    Abstract: 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: Grant
    Filed: November 15, 1985
    Date of Patent: February 23, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Atsuyoshi Yamauchi, Seiya Iguchi, Yuzo Ono, Hiroshii Kimura, Satoshi Morita
  • Patent number: 4720326
    Abstract: 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: Grant
    Filed: February 13, 1987
    Date of Patent: January 19, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heiko Beckhaus, Harro Witt, Dieter Becher, Hermann Dallmeyer, Uwe J. Zarnack
  • Patent number: 4677229
    Abstract: 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: Grant
    Filed: July 15, 1985
    Date of Patent: June 30, 1987
    Assignee: Solvay & Cie. (Societe Anonyme)
    Inventors: Leon Ninane, Claude Breton
  • Patent number: 4675445
    Abstract: 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: Grant
    Filed: November 12, 1985
    Date of Patent: June 23, 1987
    Assignee: BASF Corporation
    Inventors: Pauls Davis, Donald C. Mente
  • Patent number: 4638090
    Abstract: 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: Grant
    Filed: December 12, 1984
    Date of Patent: January 20, 1987
    Assignee: Hoechst Aktiengesellschat
    Inventors: Rudolf Heinrich, Konrad Albrecht
  • Patent number: 4559182
    Abstract: 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: Grant
    Filed: November 9, 1981
    Date of Patent: December 17, 1985
    Assignee: Buffalo Color Corporation
    Inventor: Henry M. Grotta
  • Patent number: 4552958
    Abstract: 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: Grant
    Filed: February 17, 1984
    Date of Patent: November 12, 1985
    Assignee: Texaco Inc.
    Inventors: Simon P. Burns, John M. Walton, Edward E. McEntire
  • Patent number: 4552957
    Abstract: 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: Grant
    Filed: February 17, 1984
    Date of Patent: November 12, 1985
    Assignee: Texaco Inc.
    Inventor: Edward E. McEntire
  • Patent number: 4540817
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: September 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Behre, Heinz U. Blank, Alfred Seyberlich, Ferdinand Hagedorn
  • Patent number: 4537992
    Abstract: 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: Grant
    Filed: February 9, 1984
    Date of Patent: August 27, 1985
    Assignee: Agan Chemical Manufacturers, Ltd.
    Inventors: Michael Pikarski, Julian Gabe, Edmund Dykman
  • Patent number: 4514574
    Abstract: Separate isomers via supercritical gas extraction.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: April 30, 1985
    Assignee: The Dow Chemical Company
    Inventors: Kimio Inoue, Gale G. Hoyer, Stanley I. Bates
  • Patent number: 4507475
    Abstract: 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: Grant
    Filed: July 22, 1983
    Date of Patent: March 26, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Straehle, Raymond Denni, Matthias Marx
  • Patent number: 4504663
    Abstract: 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: Grant
    Filed: November 15, 1983
    Date of Patent: March 12, 1985
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4454347
    Abstract: 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: Grant
    Filed: February 11, 1983
    Date of Patent: June 12, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Marc E. Parham, Stephen A. Spearman, Gleason O. Cookson
  • Patent number: 4452994
    Abstract: 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: Grant
    Filed: March 2, 1981
    Date of Patent: June 5, 1984
    Assignee: G. D. Searle & Co.
    Inventors: John B. Hill, Robert A. Erickson
  • Patent number: 4440953
    Abstract: 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: Grant
    Filed: April 28, 1983
    Date of Patent: April 3, 1984
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4433168
    Abstract: 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: Grant
    Filed: March 22, 1982
    Date of Patent: February 21, 1984
    Assignee: Hoechst AG
    Inventors: Hans Schubert, Konrad Baessler
  • Patent number: 4431851
    Abstract: 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: Grant
    Filed: March 8, 1983
    Date of Patent: February 14, 1984
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4400537
    Abstract: 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: Grant
    Filed: April 19, 1982
    Date of Patent: August 23, 1983
    Assignee: Standard Oil Company (Indiana)
    Inventor: Thomas A. Weil
  • Patent number: 4399307
    Abstract: The distillation of 2,2'bis(4-aminocyclohexyl)propane to yield high purity product is effectively carried out using high boiling organic solvents.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: August 16, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Tod K. Shioyama
  • Patent number: 4381408
    Abstract: 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: Grant
    Filed: December 1, 1980
    Date of Patent: April 26, 1983
    Assignee: Thermo Electron Corporation
    Inventors: David P. Rounbehler, John W. Reisch
  • Patent number: 4376216
    Abstract: 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: Grant
    Filed: August 3, 1981
    Date of Patent: March 8, 1983
    Assignee: Agfa-Gevaert AG
    Inventor: Helmut Haseler
  • Patent number: 4351958
    Abstract: 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: Grant
    Filed: August 28, 1981
    Date of Patent: September 28, 1982
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Kazunori Takahata, Katsuo Taniguchi
  • Patent number: 4347381
    Abstract: 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: Grant
    Filed: January 24, 1978
    Date of Patent: August 31, 1982
    Assignee: Ethyl Corporation
    Inventor: Melvin E. Tuvell
  • Patent number: 4340757
    Abstract: 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: Grant
    Filed: July 6, 1981
    Date of Patent: July 20, 1982
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki
  • Patent number: 4340758
    Abstract: 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: Grant
    Filed: July 6, 1981
    Date of Patent: July 20, 1982
    Assignee: Chevron Research Company
    Inventors: Seymour J. Lapporte, David M. Marquis
  • Patent number: 4335260
    Abstract: 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: Grant
    Filed: May 14, 1981
    Date of Patent: June 15, 1982
    Assignee: Montedison S.p.A.
    Inventors: Mario Bornengo, Sergio Bacciarelli
  • Patent number: 4331817
    Abstract: 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: Grant
    Filed: January 16, 1981
    Date of Patent: May 25, 1982
    Assignee: Minnesota Mining and Manufacturing Co.
    Inventor: James R. Throckmorton
  • Patent number: 4329501
    Abstract: 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: Grant
    Filed: October 9, 1980
    Date of Patent: May 11, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, Roland E. Grandin
  • Patent number: 4328369
    Abstract: 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: Grant
    Filed: January 14, 1981
    Date of Patent: May 4, 1982
    Assignee: Rumianca S.p.A.
    Inventors: Luciano Baldi, Franco Collecchia, Vittorio Messori
  • Patent number: H214
    Abstract: 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: Grant
    Filed: July 19, 1985
    Date of Patent: February 3, 1987
    Inventor: John C. Little