Preparing Directly By Nitrosation Patents (Class 564/410)
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Patent number: 10434459Abstract: A method for decomposing a nitroso compound, comprising: adding an aqueous solution containing hydrogen halide to a liquid to be treated that contains the nitroso compound in such a manner that the hydrogen halide is present in an amount of 2 mol or more and 20 mol or less per mol of a nitroso group in the nitroso compound; and subsequently heating the resulting liquid to be treated at a temperature of not lower that 75° C. and not higher than a boiling point of water under ordinary pressure, thereby an amines are recovered.Type: GrantFiled: January 7, 2015Date of Patent: October 8, 2019Assignee: MITSUBISHI HITACHI POWER SYSTEMS, LTD.Inventors: Koichi Yokoyama, Eiji Miyamoto, Jun Shimamura
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Patent number: 5808157Abstract: Aromatic amines are produced by hydrogenation of the associated aromatic nitro compounds in the gas phase over fixed catalysts. The catalysts contain active hydrogenation metals on supports. The reaction is conducted at a pressure of 2-50 bar and at a temperature in the range 250.degree.-500.degree. C. under adiabatic conditions. A circulating gas is passed over the catalyst, which circulating gas contains 3-150 moles of hydrogen, 2-100 moles of the amino groups to be formed per mole of nitro groups, and 2 to 6 moles of water per amino group equivalent. The amine and water formed, as well as a purification stream, are separated from the circulating gas. Thereafter the circulating gas is enriched with volatilised aromatic nitro compound and fresh hydrogen and recycled.Type: GrantFiled: August 4, 1995Date of Patent: September 15, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Hans-Josef Buysch, Paul Wagner, Ursula Pentling
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Patent number: 5648543Abstract: Disclosed is a process for producing a 4-nitrosodiphenylamine of the formula (2) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen atom, methyl group, ethyl group, cyclohexyl group, methoxy group, ethoxy group or chlorine or bromine atom, or a salt thereof, comprising treating a diphenylamine represented by the formula (1) ##STR2## wherein R.sub.1 and R.sub.2 are as defined above with (i) a mixture of nitrogen oxides, (ii) a hydrogen halide and (iii) an aliphatic alcohol, wherein the atomic ratio of oxygen to nitrogen of the mixture of nitrogen oxides is more than 1.0 and less than 2.0. This process produces 4-nitrosodiphenylamine of the formula (2) or a salt thereof conveniently and effectively, and is industrially advantageous.Type: GrantFiled: June 6, 1995Date of Patent: July 15, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tetsuo Murata, Hiroyuki Takagi, Yasumi Katayama
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Patent number: 5475140Abstract: 4-Amino-3-methyl-N-ethyl-N-(.beta.-hydroxyethyl)-aniline sulfate which is used particularly as a developer for color photography can be easily produced in high yield and high quality by nitrosating N-ethyl-N-(.beta.-hydroxyethyl)-m-toluidine by use of an alkyl nitrite in a homogeneous alcohol solution containing sulfuric acid in an amount of about 0.5 to about 1 mole per mole of N-ethyl-N-(.beta.-hydroxyethyl)-m-toluidine, and then reducing the nitrosation product in an aqueous alcohol solution after or without isolation of the nitrosation product.Type: GrantFiled: April 19, 1994Date of Patent: December 12, 1995Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Takehiko Iritani, Ryohiko Kinoshita, Yoshiki Kametani
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Patent number: 4723040Abstract: A process for preparing an N-mono-substituted-p-phenylenediamine by reacting the corresponding p-nitroso-N-mono-substituted aniline compound with a primary or secondary alcohol in the presence of a base.Type: GrantFiled: December 19, 1986Date of Patent: February 2, 1988Assignee: Uniroyal Chemical Company, Inc.Inventor: Wadim Batorewicz
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Patent number: 4518803Abstract: A process is disclosed for the preparation of p-nitrosodiphenylamine hydrochloride comprising reacting diphenylamine, C.sub.5 -C.sub.10 alkyl nitrite and anhydrous HCl in the presence of a C.sub.5 -C.sub.10 aliphatic alcohol and essentially in the absence of an aromatic solvent.Type: GrantFiled: September 30, 1982Date of Patent: May 21, 1985Assignee: Uniroyal, Inc.Inventors: Wadim Batorewicz, Edward L. Wheeler
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Patent number: 4479008Abstract: A process for preparing p-nitrosodiphenylamine hydrochloride is provided from N-nitrosodiphenylamine and hydrogen chloride. The product is prepared in the absence of an aromatic solvent and using a solvent consisting essentially of aliphatic C.sub.5 -C.sub.10 alcohol.Type: GrantFiled: September 30, 1982Date of Patent: October 23, 1984Assignee: Uniroyal, Inc.Inventors: Wadim Batorewicz, Edward L. Wheeler
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Patent number: 4474987Abstract: A process for preparing an N,N-disubstituted p-phenylenediamine of the formula ##STR1## wherein R.sup.1 is alkyl of 1-6 C atoms, R.sup.2 is alkyl of 1-6 C atoms or alkyl of 1-6 C atoms which is substituted by OH, lower alkoxy, a sulfo group or an alkylsulfonamido group and R.sup.3 is hydrogen or lower alkylor an acid addition salt thereof,comprises adding an alkyl nitrite, as a nitrosation agent,to an aqueous, acid suspension of the corresponding aniline derivative of the formula ##STR2## thereby forming the corresponding N,N-disubstituted p-nitroso-aniline, and subsequently hydrogenating the latter without isolation thereof from the reaction mixture.Type: GrantFiled: April 5, 1982Date of Patent: October 2, 1984Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Bruno Wollemann, Hartmut Hartner, Hans Bardonner
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Patent number: 4362893Abstract: C-Nitrosodiarylamines may be prepared in a single stage from diarylamines by adding alcoholic solutions of a hydrogen halide below the surface of a stirred mixture of the diphenylamine in an organic liquid containing water. The amount of water contained is critical, and amounts from about 1 to about 3 g per mole of diarylamine are preferred.Type: GrantFiled: June 3, 1981Date of Patent: December 7, 1982Assignee: UOP Inc.Inventor: Paul R. Kurek
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Patent number: 4324913Abstract: A process for the preparation of 4-nitroso-diphenylamine by rearranging N-nitroso-diphenylamine according to Fischer-Hepp to o-dichlorobenzene, under the effect of alcoholic hydrochloric acid and working up the suspension of the 4-nitroso-diphenylamine-hydrochloride.Type: GrantFiled: September 2, 1980Date of Patent: April 13, 1982Assignee: Bayer AktiengesellschaftInventors: Karlfried Wedemeyer, Lutz Kienitz
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Patent number: 4313002Abstract: A method of preparing p-aminodiphenylamines from diphenylamines is described whereby neither the N-nitrosodiphenylamine or the p-nitrosodiphenylamine need be isolated. The method rests on the discovery that alkali metal salts of p-nitrosodiphenylamines are soluble in non-aqueous organic solvent systems consisting of certain aromatic hydrocarbons and saturated aliphatic alcohols, and that such salts can be readily hydrogenated in their non-aqueous solution to the corresponding p-aminodiphenylamine.Type: GrantFiled: October 29, 1980Date of Patent: January 26, 1982Assignee: UOP Inc.Inventors: Ted Symon, Paul R. Kurek, Michael D. Tufano