Preparing Directly By Reacting Carbonyl With Hydroxylamine Or Salt Thereof Patents (Class 564/259)
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Patent number: 5502254Abstract: 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: GrantFiled: March 15, 1995Date of Patent: March 26, 1996Assignee: Zeneca LimitedInventor: Daniel Levin
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Patent number: 5488161Abstract: 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: GrantFiled: March 30, 1994Date of Patent: January 30, 1996Assignee: Henkel CorporationInventor: Leroy O. Krbechek
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Patent number: 5488162Abstract: 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: GrantFiled: January 3, 1994Date of Patent: January 30, 1996Inventor: Paul R. Buckland
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Patent number: 5434307Abstract: 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: GrantFiled: May 21, 1993Date of Patent: July 18, 1995Assignee: Howard UniversityInventors: Chukwuma P. Nwaonicha, Folahan O. Ayorinde
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Patent number: 5426231Abstract: 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: GrantFiled: January 5, 1994Date of Patent: June 20, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Richard V. C. Carr, Barry J. Koehler
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Patent number: 5399761Abstract: 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: GrantFiled: August 19, 1993Date of Patent: March 21, 1995Assignee: Zeneca LimitedInventor: Daniel Levin
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Patent number: 5364609Abstract: 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: GrantFiled: June 15, 1993Date of Patent: November 15, 1994Assignee: DSM N.V.Inventors: Hendrikus J. H. Rouhof, Godefridus M. Van Dortmont, Michael W. M. Boesten
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Patent number: 5349088Abstract: 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: GrantFiled: July 7, 1993Date of Patent: September 20, 1994Assignee: Henkel CorporationInventor: Leroy O. Krbechek
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Patent number: 5334762Abstract: 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: GrantFiled: February 4, 1993Date of Patent: August 2, 1994Assignee: Zeneca Inc.Inventors: James P. Neilan, Donald J. Gosciniak
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Patent number: 5319142Abstract: 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: GrantFiled: October 6, 1992Date of Patent: June 7, 1994Assignee: Hoechst Celanese CorporationInventors: Joseph A. McDonough, Ahmed M. Tafesh, Olan S. Fruchey
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Patent number: 5312987Abstract: 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: GrantFiled: March 30, 1993Date of Patent: May 17, 1994Assignee: Enichem Anic S.r.l.Inventors: Maria A. Mantegazza, Guido Petrini, Alberto Cesana
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Patent number: 5300690Abstract: 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: GrantFiled: October 14, 1992Date of Patent: April 5, 1994Assignee: Akzo N.V.Inventor: Gurudas D. Sinai-Zingde
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Patent number: 5300689Abstract: 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: GrantFiled: March 20, 1992Date of Patent: April 5, 1994Assignee: Henkel CorporationInventors: Leroy O. Krbechek, Mary I. Casey
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Patent number: 5254734Abstract: 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: GrantFiled: February 7, 1992Date of Patent: October 19, 1993Assignee: Mitsubishi Kasei CorporationInventors: Yu Kanda, Takeshi Matsuoka, Haruo Habu, Tsutomu Yonemori
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Patent number: 5227525Abstract: 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: GrantFiled: January 21, 1992Date of Patent: July 13, 1993Assignee: Enichem Anic s.r.l.Inventors: Sergio Tonti, Paolo Roffia, Vittorio Gervasutti
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Patent number: 5117060Abstract: 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: GrantFiled: June 10, 1991Date of Patent: May 26, 1992Assignee: Eastman Kodak CompanyInventor: Jonathan S. Witzeman
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Patent number: 5072056Abstract: A novel method of preparing 2-phenyl substituted-1, 3-propanediols, useful intermediates in the synthesis of pharmaceutical preparations is disclosed.Type: GrantFiled: September 26, 1989Date of Patent: December 10, 1991Assignee: Carter-Wallace, Inc.Inventor: Frank J. Stiefel
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Patent number: 5041652Abstract: 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: GrantFiled: September 17, 1990Date of Patent: August 20, 1991Assignee: Montedipe S.p.A.Inventors: Mario Padovan, Giordano De Alberti, Paolo Roffia
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Patent number: 4994613Abstract: 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: GrantFiled: January 29, 1990Date of Patent: February 19, 1991Assignee: Hoechst Celanese CorporationInventor: Olan S. Fruchey
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Patent number: 4922017Abstract: 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: GrantFiled: June 20, 1988Date of Patent: May 1, 1990Assignee: Allied-Signal Inc.Inventor: Chempolil T. Mathew
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Patent number: 4868327Abstract: A novel method for preparing 2-phenyl-1, 3-propanediol and its dicarbamate is disclosed which readily lends itself to commercial production.Type: GrantFiled: June 3, 1987Date of Patent: September 19, 1989Assignee: Carter-Wallace, Inc.Inventor: Frank J. Stiefel
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Patent number: 4788130Abstract: 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: GrantFiled: August 29, 1985Date of Patent: November 29, 1988Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Yasuo Oshiro, Hiraki Ueda, Kazuyuki Nakagawa
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Patent number: 4707294Abstract: 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: GrantFiled: September 9, 1985Date of Patent: November 17, 1987Assignee: Allied CorporationInventors: Chempolil T. Mathew, Harry E. Ulmer
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Patent number: 4654169Abstract: 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: GrantFiled: January 27, 1986Date of Patent: March 31, 1987Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4584403Abstract: 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: GrantFiled: February 27, 1984Date of Patent: April 22, 1986Assignee: PPG Industries, Inc.Inventor: Dennis K. Krass
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Patent number: 4552636Abstract: 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: GrantFiled: June 4, 1984Date of Patent: November 12, 1985Assignee: Stamicarbon B.V.Inventors: Franciscus van den Brink, Marinus Alfenaar
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Patent number: 4539405Abstract: 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: GrantFiled: April 16, 1984Date of Patent: September 3, 1985Assignee: The United States of America as represented by the Secretary of the NavyInventor: Rodney L. Willer
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Patent number: 4507248Abstract: 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: GrantFiled: September 23, 1983Date of Patent: March 26, 1985Assignee: Allied CorporationInventors: Chempolil T. Mathew, Harry E. Ulmer
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Patent number: 4438282Abstract: 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: GrantFiled: June 23, 1982Date of Patent: March 20, 1984Assignee: BASF AktiengesellschaftInventors: Hartmut Lardon, Guenther Seybold
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Patent number: 4426321Abstract: 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: GrantFiled: July 24, 1981Date of Patent: January 17, 1984Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4328198Abstract: 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: GrantFiled: October 2, 1980Date of Patent: May 4, 1982Assignee: Stamicarbon, B.V.Inventor: Cornelis G. M. van de Moesdijk
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Patent number: 4323706Abstract: 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: GrantFiled: December 18, 1980Date of Patent: April 6, 1982Assignee: Allied CorporationInventors: John H. Bonfield, Stephen E. Belsky, Donald Pickens
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Patent number: 4263223Abstract: 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: GrantFiled: April 20, 1977Date of Patent: April 21, 1981Assignee: Laboratoires Serobiologiques S.A.Inventor: Marc Pauly
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Patent number: 4240981Abstract: 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: GrantFiled: March 7, 1979Date of Patent: December 23, 1980Assignee: Shell Oil CompanyInventor: Riekert Kok