Preparing Directly By Reacting Carbonyl With Hydroxylamine Or Salt Thereof Patents (Class 564/259)
  • Patent number: 5502254
    Abstract: A method for the preparation of a 2-hydroxyarylaldoxime which comprises reacting hydroxylamine with a 2-hydroxyarylaldehyde, said reaction being performed in the presence of a compound of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table and/or under such conditions that the 2-hydroxyarylaldehyde is at least partially in the form of a salt and/or complex of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table.
    Type: Grant
    Filed: March 15, 1995
    Date of Patent: March 26, 1996
    Assignee: Zeneca Limited
    Inventor: Daniel Levin
  • Patent number: 5488161
    Abstract: An improved process for oximation of carbonyl compounds, such as ketones and aldehydes by oximation with hydroxylamine including oximation processes carried out in the presence of a catalytic amount of a phase transfer catalyst comprised of a mixture of an alkyl phenol, such as nonylphenol or dodecylphenol and an organic carboxylic acid, such as 2-ethylhexanoic acid, in the presence of an alkali metal or alkaline earth metal compound. The resulting oximes are useful as metal extractants.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: January 30, 1996
    Assignee: Henkel Corporation
    Inventor: Leroy O. Krbechek
  • Patent number: 5488162
    Abstract: This invention relates to a process for preparing aqueous solutions of O-alkylhydroxylamine salts. The process involves converting hydroxylamine salts to their O-alkyl derivatives without the isolation of intermediates. More specifically, the process involves three steps. The first step, Step (A), involves forming a ketoxime. The second step, Step (B), involves adding an alkylating agent to the ketoxime formed in Step (A). The third step, Step (C), involves hydrolysing the alkylated ketoxime formed in Step (B) to yield an O-alkylhydroxylamine salt. O-alkylhydroxylamine salts are important intermediates in the preparation of herbicides.
    Type: Grant
    Filed: January 3, 1994
    Date of Patent: January 30, 1996
    Inventor: Paul R. Buckland
  • Patent number: 5434307
    Abstract: A process for producing 12-oxododecanoic acid oxime, a novel compound which can be used as a raw material in several industrial processes, is disclosed. The disclosed process relies on a renewable raw material, vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid. The process utilizes readily available chemical technology which does not involve the use of gaseous hydrocarbon or petrochemical-base feedstock. Hydrogenation of vernolic acid produces 12,13-epoxystearic acid, which can be oxidized with periodic acid to give 12-oxododecanoic acid, which can be reacted with hydroxylamine to yield 12-oxododecanoic acid oxime. A process for reducing the 12-oxododecanoic acid oxime to yield 12-aminododecanoic acid, the monomer for nylon-12, is also disclosed.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: July 18, 1995
    Assignee: Howard University
    Inventors: Chukwuma P. Nwaonicha, Folahan O. Ayorinde
  • Patent number: 5426231
    Abstract: This invention relates to an improved process for the preparation of 3-aminopropanol and a primary amine by reacting a cyanoethyl ketoxime with hydrogen in the presence of a hydrogenation catalyst to generate the primary amine and aminopropanol. The sequence of reactions to form the aminopropanol and primary amine involves the reaction of hydroxylamine with a ketone to generate a ketoxime followed by reaction of acrylonitrile with the ketoxime to generate a cyanoethyl ketoxime followed by complete hydrogenation of the cyanoethyl ketoxime in the presence of a hydrogenation catalyst to generate the primary amine and aminopropanol. The significant advantage associated with this process is the high degree of selectivity to 3-aminopropanol and the primary amine.
    Type: Grant
    Filed: January 5, 1994
    Date of Patent: June 20, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Richard V. C. Carr, Barry J. Koehler
  • Patent number: 5399761
    Abstract: A method for the preparation of a 2-hydroxyarylaldoxime which comprises reacting hydroxylamine with a 2-hydroxyarylaldehyde, said reaction being performed in the presence of a compound of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table and/or under such conditions that the 2-hydroxyarylaldehyde is at least partially in the form of a salt and/or complex of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table.
    Type: Grant
    Filed: August 19, 1993
    Date of Patent: March 21, 1995
    Assignee: Zeneca Limited
    Inventor: Daniel Levin
  • Patent number: 5364609
    Abstract: A process for the preparation and processing of a hydroxylammonium salt solution involves maintaining an aqueous acid reaction medium circulation between a hydroxylammonium salt synthesis zone and an oxime synthesis zone; continuously supplying nitrate ions or nitrogen oxides to be converted into nitrate, by way of nitrogen source for the formation of the hydroxylammonium salt, to the liquid being maintained in circulation; catalytically reducing the nitrate ions with hydrogen to obtain hydroxylamine; removing the ammonium ions, formed as a by-product in the reduction of the nitrate ions, by contacting the circulating liquid with a gas flow consisting of nitrogen oxides generated in catalytic combustion of ammonia. Advantageously, 0.01 to 5 wt. % of the nitrogen oxides formed in the combustion effect reduction of the ammonium ions to nitrogen, and the remainder of the nitrogen oxides are used for the preparation of nitric acid.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: November 15, 1994
    Assignee: DSM N.V.
    Inventors: Hendrikus J. H. Rouhof, Godefridus M. Van Dortmont, Michael W. M. Boesten
  • Patent number: 5349088
    Abstract: An improved process for oximation of carbonyl compounds, such as ketones and aldehydes by oximation with hydroxylamine including oximation processes carried out in the presence of a catalytic amount of an alkyl phenol phase transfer catalyst, such as nonylphenol or dodecylphenol and the presence of an alkali metal or alkaline earth metal compound. The resulting oximes are useful as metal extractants.
    Type: Grant
    Filed: July 7, 1993
    Date of Patent: September 20, 1994
    Assignee: Henkel Corporation
    Inventor: Leroy O. Krbechek
  • Patent number: 5334762
    Abstract: A method for preparing oximes where an aldehyde or ketone is reacted with hydroxylamine or its salt in the presence of a catalytic amount of an organotin(IV) compound such as monoalkyltin(IV), dialkyltin(IV) and aryltin(IV). The organotin(IV) compound is represented by the formula I:(R.sup.1).sub.n SnX.sub.m-n (I)where R.sup.1 is independently selected from alkyl of 1 to 18 carbons or aryl, X is halogen, oxygen, hydroxyl, OR.sup.1, R.sup.2 CO.sub.2 --, R.sup.2 O.sub.2 C--(Z).sub.y --CO.sub.2 -- or R.sup.2 CO.sub.2 (CH.sub.2).sub.y S--, R.sup.2 is alkyl of 1 to 18 carbons or aryl, Z is selected from CH.sub.2 or CH.dbd.CH, where y is 0 to 6, n is 1 or 2 and m is 4 except that when X is oxygen, n is 2 and m is 3. Exemplary of the organotin(IV) compounds are butyltin tris(2-ethylhexanoate), dibutyltin diacetate and diphenyltin dichloride.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: August 2, 1994
    Assignee: Zeneca Inc.
    Inventors: James P. Neilan, Donald J. Gosciniak
  • Patent number: 5319142
    Abstract: An arylisonitrosoalkanone is hydrogenated in the presence of a noble metal catalyst and a weak carboxylic acid to form an arylalkanolamine which is then hydrogenated in the presence of a strong mineral acid and the transition metal catalyst to form an arylalkylamine. When the arylisonitrosoalkanone is an isonitrosoacetophenone, the isonitrosoacetophenone is prepared by one of two methods.In the first method, a substituted or an unsubstituted isonitrosoacetophenone is prepared from a corresponding substituted or unsubstituted acetophenone by oxidizing the acetophenone to form a substituted or an unsubstituted phenylglyoxalacetal in a reactor, hydrolyzing the phenylglyoxal acetal in the same reactor to form a corresponding substituted or unsubstituted phenylglyoxal, and condensing the phenylglyoxal with hydroxylamine or a salt thereof in the same reactor to form the substituted or unsubstituted isonitrosoacetophenone.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: June 7, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Joseph A. McDonough, Ahmed M. Tafesh, Olan S. Fruchey
  • Patent number: 5312987
    Abstract: Two-step process in the liquid phase for producing oximes at 60.degree.-100.degree. C. and 1.5-5 bars, which comprises:(a) in a primary step, ammoximating a carbonylic compound with H.sub.2 O.sub.2 and NH.sub.3 in the presence of a silicon, titanium and oxygen based catalyst;(b) oximating the residual carbonylic compound with a solution of hydroxylamine, obtained in its turn by oxidizing ammonia with H.sub.2 O.sub.2, having a concentration comprised within the range of from 0.01 to 3%, preferably of from 0.5 to 2% by weight, in such a way as to have a molar ratio of hydroxylamine to the carbonylic compound comprised within the range of from 0.9 to 3, preferably of from 1 to 2.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: May 17, 1994
    Assignee: Enichem Anic S.r.l.
    Inventors: Maria A. Mantegazza, Guido Petrini, Alberto Cesana
  • Patent number: 5300690
    Abstract: A polyoxime can be formed by reacting hydroxylamine with a copolymer of carbon monoxide and propylene. When the relative amount of oxime units in the polyoxime is high the polyoxime is soluble in water. Conversely, solubility in organic solvent is conferred when the oxime content is relatively low.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: April 5, 1994
    Assignee: Akzo N.V.
    Inventor: Gurudas D. Sinai-Zingde
  • Patent number: 5300689
    Abstract: An improved process for oximation of carbonyl compounds, such as ketones and aldehydes by oximation with hydroxylamine including oximation processes carried out in the presence of a catalytic amount of an acid phase transfer catalyst, such as 2-ethylhexanoic acid, and/or the presence of an alkali metal or alkaline earth metal catalyst. The resulting oximes are useful as metal extractants.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: April 5, 1994
    Assignee: Henkel Corporation
    Inventors: Leroy O. Krbechek, Mary I. Casey
  • Patent number: 5254734
    Abstract: A method for preparing an oxime, which comprises partitioning an aqueous hydroxylamine salt solution phase and a ketone or aldehyde phase by a cation exchange membrane, and permitting hydroxylamine in the aqueous hydroxylamine salt solution phase to diffuse and transfer through the membrane to the ketone or aldehyde phase and to form an oxime in the ketone or aldehyde phase.
    Type: Grant
    Filed: February 7, 1992
    Date of Patent: October 19, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Yu Kanda, Takeshi Matsuoka, Haruo Habu, Tsutomu Yonemori
  • Patent number: 5227525
    Abstract: A multistep process for the liquid phase ammoximation of carbonyl compounds with H.sub.2 O.sub.2 and NH.sub.3, at 60.degree.-100.degree. C., at 1.5-5 bar and in the presence of a catalyst based on silicon, titanium and oxygen, characterized in that:a) in one or more primary steps, the H.sub.2 O.sub.2 : carbonyl compound molar ratio ranges from 0.9 to 1.15 by mols and the carbonyl component conversion is carried out up to at least 95%;b) in a last (exhaustion) step the H.sub.2 O.sub.2 : carbonyl compound ratio is in a higher range, i.e. from 1.5 to 3.0 by mols.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: July 13, 1993
    Assignee: Enichem Anic s.r.l.
    Inventors: Sergio Tonti, Paolo Roffia, Vittorio Gervasutti
  • Patent number: 5117060
    Abstract: Disclosed is an improved process for the preparation of ketoximes, especially ketoximes derived from branched chain ketones, wherein a ketone is reacted with a hydroxylamine salt in the presence of an alkanol, a heterogeneous base and up to about 5 weight percent, based on the weight of the ketone and alkanol, water.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: May 26, 1992
    Assignee: Eastman Kodak Company
    Inventor: Jonathan S. Witzeman
  • Patent number: 5072056
    Abstract: A novel method of preparing 2-phenyl substituted-1, 3-propanediols, useful intermediates in the synthesis of pharmaceutical preparations is disclosed.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: December 10, 1991
    Assignee: Carter-Wallace, Inc.
    Inventor: Frank J. Stiefel
  • Patent number: 5041652
    Abstract: The present invention relates to a method of preparing a catalyst for the ammoximation of carboxylic compounds, consisting of a synthetic, crystaline and porous material based on silicon and titanium oxides, characterized in that a preformed matrix of amorphous silica is impregnated with an aqueous solution, containing a titanium compound and an organic compound of nitrogen, as a templating agent, and that to the thus impregnated material a zeolitic structure is given by means of a hydrothermal synthesis of usual type, shape and size of the matrix being substantially maintained unchanged.
    Type: Grant
    Filed: September 17, 1990
    Date of Patent: August 20, 1991
    Assignee: Montedipe S.p.A.
    Inventors: Mario Padovan, Giordano De Alberti, Paolo Roffia
  • Patent number: 4994613
    Abstract: A novel process is disclosed for the preparation of 4-hydroxyacetopheone oxime by reaction of 4-hydroxyacetophenone with a hydroxylamine in caustic wherein the mother liquor obtained after crystallization of the oxime together with the wash water is recycled back and reused. This invention illustrates the criticality of maintaining the reactants in certain critical mol ratios in order to obtain 4-hydroxyacetopheone oxime of acceptable color.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: February 19, 1991
    Assignee: Hoechst Celanese Corporation
    Inventor: Olan S. Fruchey
  • Patent number: 4922017
    Abstract: A process for preparing an aromatic aldoxime, such as benzaldehyde oxime, by reacting the corresponding, .alpha.,.alpha.-dihalide, such as benzal chloride, with a hydroxylamine salt in the presence of an excess of an aqueous base sufficient to maintain the product oxime in solution. Organic impurities may be phase separated from the reaction mixture. Thereafter, the aqueous solution containing product oxime is neutralized to separate an oxime phase, which may be recovered by decanting or solvent extraction.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: May 1, 1990
    Assignee: Allied-Signal Inc.
    Inventor: Chempolil T. Mathew
  • Patent number: 4868327
    Abstract: A novel method for preparing 2-phenyl-1, 3-propanediol and its dicarbamate is disclosed which readily lends itself to commercial production.
    Type: Grant
    Filed: June 3, 1987
    Date of Patent: September 19, 1989
    Assignee: Carter-Wallace, Inc.
    Inventor: Frank J. Stiefel
  • Patent number: 4788130
    Abstract: Novel 2,3-dihydro-1H-indene derivatives and salts thereof represented by the general formula (1), ##STR1## [wherein R.sup.1 and R.sup.2 are each a hydrogen atom, a lower alkyl group, a phenyl group which may have halogen atoms and/or alkyl groups as the substituents on the phenyl ring; R.sup.3 is a halogen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a phenyl-lower alkyl group, a cycloalkyl-lower alkyl group or the like; R.sup.5 is a hydroxyimino group, an alkylamino group or a group of the formula --NHR.sup.8 (wherein R.sup.8 is a hydrogen atom, a halogen-substituted lower alkanoyl group or the like); R.sup.6 is a hydrogen atom or a phenyl group; and R.sup.7 is a hydrogen atom or a lower alkyl group].
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: November 29, 1988
    Assignee: Otsuka Pharmaceutical Co., Ltd.
    Inventors: Yasuo Oshiro, Hiraki Ueda, Kazuyuki Nakagawa
  • Patent number: 4707294
    Abstract: Solid hydroxylammonium sulfate is reacted with an alcohol solution of an alkali metal hydroxide or alkoxide to produce an alcoholic hydroxylamine liquid phase and a sulfate-containing solid phase. The liquid phase may be used for further reactions such as oxidations, hydroxamic acid production or neutralization to other hydroxylammonium salts. The different bases behave differently with regard to suitable and preferable solvents and temperatures.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: November 17, 1987
    Assignee: Allied Corporation
    Inventors: Chempolil T. Mathew, Harry E. Ulmer
  • Patent number: 4654169
    Abstract: The invention concerns the novel odorants 2,2,4-trimethyl-1-phenyl-3-pentanone oxime, 2,4,4-trimethyl-5-phenyl-3-hexanone oxime and 2,4,4-trimethyl-5-phenyl-3-heptanone oxime, a process for making same, odorant compositions containing same and methods for preparing improved odorant compositions using same.
    Type: Grant
    Filed: January 27, 1986
    Date of Patent: March 31, 1987
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4584403
    Abstract: This invention relates to certain herbicidally active substituted diphenyl ether oxime derivatives, herbicidal compositions of the same and the use thereof for preemergence and postemergence control of noxious plants, i.e., weeds.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: April 22, 1986
    Assignee: PPG Industries, Inc.
    Inventor: Dennis K. Krass
  • Patent number: 4552636
    Abstract: A process for the preparation of a hydroxylammonium slat and an oxime from said hydroxylammonium salt and an aldehyde or keton is disclosed in which an aqueous acid reaction medium is kept in circulation between a zone for the synthesis of the salt and a zone for the synthesis of the oxime and in which nitrate ions and/or nitrogen monoxide are continuously supplied as a reducible nitrogen source for the liquid kept in circulation, wherein the circulation liquid is subjected to an electrodialysis to remove the ammonium ions formed as a byproduct in the hydroxylammonium salt synthesis.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: November 12, 1985
    Assignee: Stamicarbon B.V.
    Inventors: Franciscus van den Brink, Marinus Alfenaar
  • Patent number: 4539405
    Abstract: The novel explosive compound, 1,4-dinitrofurazano[3,4-b]piperazine, is prred by the reaction of 2,3-dioximinopiperazine with a base, followed by the nitration of the intermediate furazano[3,4-b]piperazine. The nitrated compound has a density, detonation pressure, detonation velocity and Isp similar to RDX while being highly insensitive.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: September 3, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Rodney L. Willer
  • Patent number: 4507248
    Abstract: Solid hydroxylammonium sulfate is reacted with an alcohol solution of an alkali metal hydroxide or alkoxide to produce an alcoholic hydroxylamine liquid phase and a sulfate-containing solid phase. The liquid phase is used for further reactions such as oximations and hydroxamic acid production. The different bases behave differently with regard to suitable and preferable solvents and temperatures.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: March 26, 1985
    Assignee: Allied Corporation
    Inventors: Chempolil T. Mathew, Harry E. Ulmer
  • Patent number: 4438282
    Abstract: Sulfides prepared by reacting a sulfoxide with a hydrazine or hydroxylamine derivative or a quaternary salt thereof are useful starting materials for the preparation of drugs, pesticides and dyes.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: March 20, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Hartmut Lardon, Guenther Seybold
  • Patent number: 4426321
    Abstract: This invention discloses a number of novel odorant alkadienyl ketones, alcohols and oximes having from 9 to 15 carbon atoms, processes for making same and odorant compositions containing same.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: January 17, 1984
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4328198
    Abstract: The process relates to hydroxylammonium salts.Cyclic process for the preparation and processing of a hydroxylammonium salt solution, in which an aqueous acid reaction medium is kept in circulation between a hydroxylammonium salt synthesis zone and an oxime synthesis zone, and in which the circulating liquid is continuously supplied with nitrogen monoxide, which serves as nitrogen source for the formation of the hydroxylammonium salt, and which is converted into hydroxylamine by catalytic reduction with hydrogen.The circulating liquid is, before it enters the hydroxylammonium salt synthesis zone, subjected to a stripping process by bringing the circulating liquid via a heat-exchanging surface in heat-exchange with nitrogen monoxide containing water vapor, upon which the water vapor condenses, and the remaining gas containing nitrogen monoxide as nitrogen source is used in the reduction of nitrogen monoxide to hydroxylamine.
    Type: Grant
    Filed: October 2, 1980
    Date of Patent: May 4, 1982
    Assignee: Stamicarbon, B.V.
    Inventor: Cornelis G. M. van de Moesdijk
  • Patent number: 4323706
    Abstract: Acetaldehyde oxime, a commercially useful intermediate in the production of pesticides, is prepared by oximating acetaldehyde with an aqueous hydroxylamine-containing solution to form an aqueous oximation reaction mixture and recovering acetaldehyde oxime from the aqueous oximation reaction mixture by distilling a mixture of acetaldehyde oxime and water directly from the aqueous oximation reaction mixture.
    Type: Grant
    Filed: December 18, 1980
    Date of Patent: April 6, 1982
    Assignee: Allied Corporation
    Inventors: John H. Bonfield, Stephen E. Belsky, Donald Pickens
  • Patent number: 4263223
    Abstract: A chemical compound of the formula: ##STR1## wherein X is a halogen selected from bromine, chlorine, iodine and fluorine, and preferably bromine; Z is selected from the group constituted by --CHO, --CH.dbd.NOH, --C.tbd.N; n is an integer from 1 to 11; m.sub.1 and m.sub.2, identical or different, are integers from 1 to 4.
    Type: Grant
    Filed: April 20, 1977
    Date of Patent: April 21, 1981
    Assignee: Laboratoires Serobiologiques S.A.
    Inventor: Marc Pauly
  • Patent number: 4240981
    Abstract: The invention relates to a process for the preparation of a 1,2-dioxime of the general formula A--C(.dbd.NOH)--C(.dbd.NOH)--R, wherein A represents an aromatic group and R a hydrocarbyl group or a hydrogen atom, which process comprises the reaction of hydroxylamine with one or more hydroxyiminoketones of formula A--C(.dbd.O)--C(.dbd.NOH)--R or of formula A--C(.dbd.NOH)--C(.dbd.NOH)--R in the presence of a nickel compound forming a complex with the 1,2-dioxime.
    Type: Grant
    Filed: March 7, 1979
    Date of Patent: December 23, 1980
    Assignee: Shell Oil Company
    Inventor: Riekert Kok