Of Acrylonitriles Patents (Class 564/128)
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Patent number: 9029587Abstract: There is provided a method for producing an aqueous acrylamide solution by reacting a composition including acrylonitrile with water to produce acrylamide, in which the composition including acrylonitrile includes 3 to 15 mg of propionitrile per 1 kg of the total weight of the composition including acrylonitrile. According to the present invention, a production method with which it is possible to suppress acrylamide polymerization without lowering quality and thereby obtain a stable aqueous acrylamide solution can be provided.Type: GrantFiled: May 21, 2012Date of Patent: May 12, 2015Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Makoto Kanou, Norifumi Hagiya
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Patent number: 8889907Abstract: The present invention provides a method for producing an amide compound from a nitrile compound using a biocatalyst that realizes low cost, energy saving and low environmental burdens. The production method of the amide compound of the present invention is a method for producing an amide compound from a nitrile compound using a biocatalyst in a reactor, wherein the nitrile compound is reacted with the biocatalyst to produce the amide compound under such stirring conditions that the stirring power requirement is in the range of 0.08 to 0.7 kW/m3.Type: GrantFiled: March 13, 2009Date of Patent: November 18, 2014Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Makoto Kanou, Kiyonobu Niwa, Masahito Oda
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Patent number: 8722912Abstract: A catalyst contains a metal complex compound represented by the following general formula (I). In the formula (I), M is a metal ion such as ruthenium, L1 is a cyclic or acyclic, neutral or minus 1-valent unsaturated hydrocarbon group of 1 to 30 carbon atoms which may have a substituent, L2 and L3 are each independently chlorine or the like, and L4 is a compound bonded to M through phosphorus or arsenic and represented by the following general formula (IIa) or (IIb). In the formulas (IIa) and (IIb), E is phosphorus or arsenic, Y1 is oxygen or sulfur, Y2, Y3 and Y4 are each independently a hydrogen atom, an aryl group or the like, and H is a hydrogen atom.Type: GrantFiled: July 29, 2011Date of Patent: May 13, 2014Assignee: National University Corporation Okayama UniversityInventors: Toshiyuki Oshiki, Makoto Muranaka
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Patent number: 8603939Abstract: The present provides a high-efficiency amide compound production catalyst to be used in producing an amide compound through hydration of a nitrile compound and a production method using it. The amide compound production catalyst is for producing an amide compound through reaction of a nitrile compound and water, and comprises a manganese oxide catalyst containing bismuth and further containing yttrium or vanadium. The method for producing an amide compound comprises reacting a nitrile compound and water in a liquid phase in the presence of the amide compound production catalyst.Type: GrantFiled: March 4, 2011Date of Patent: December 10, 2013Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takako Uchiyama, Shinyou Shirai, Yoshikazu Shima, Masaki Takemoto, Genki Nogami
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Publication number: 20130131366Abstract: A catalyst contains a metal complex compound represented by the following general formula (I). In the formula (I), M is a metal ion such as ruthenium, L1 is a cyclic or acyclic, neutral or minus 1-valent unsaturated hydrocarbon group of 1 to 30 carbon atoms which may have a substituent, L2 and L3 are each independently chlorine or the like, and L4 is a compound bonded to M through phosphorus or arsenic and represented by the following general formula (IIa) or (IIb). In the formulas (IIa) and (IIb), E is phosphorus or arsenic, Y1 is oxygen or sulfur, Y2, Y3 and Y4 are each independently a hydrogen atom, an aryl group or the like, and H is a hydrogen atom.Type: ApplicationFiled: July 29, 2011Publication date: May 23, 2013Applicant: NATIONAL UNIVERSITY CORPORATION OKAYAMA UNIVERSITYInventors: Toshiyuki Oshiki, Makoto Muranaka
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Publication number: 20040175810Abstract: The invention relates to a method and a device for the production of an aqueous acrylamide solution by hydration of acrylnitrile in an aqueous solution in the presence of a bio-catalyst.Type: ApplicationFiled: April 30, 2004Publication date: September 9, 2004Inventors: Olaf Petersen, Peter Kroemker
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Patent number: 6472561Abstract: Stable highly active supported copper based catalysts of copper oxide or elemental copper crystallites supported on mechanically stable aluminum oxide are disclosed. These catalysts are characterized by high surface area, small copper crystallite size, and high metal loading. The average crystallite size of the copper compound is from about 20 to about 300 Å, the copper loading is from about 10 to about 35 weight percent, the average particle diameter is from about 0.1 mm to about 10 mm, and the total surface area is from about 20 to about 400 square meters per gram. The catalysts are useful for hydration of nitrites to amides, especially hydration of acrylonitrile to acrylamide. The catalysts are distinguished by high mechanical stability, extended lifetime, and excellent resistance to hydration and copper leaching.Type: GrantFiled: September 28, 2001Date of Patent: October 29, 2002Assignee: Cytec Technology CorpInventors: Mark Donal Ryan, John Bradley Roucis, James Donald Carruthers
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Patent number: 6133478Abstract: A platinum complex useful as a catalyst for converting nitrites into amides comprises a platinum complex of dialkyl phosphine of stoichiometric formula: PtX(R.sub.2 POHOPR.sub.2)(PR.sub.2 OH) where R is an alkyl, alicyclic, chiral, alkylaryl group or substituted alkyl, alicyclic, chiral, alkaryl group or the two R groups attached to one phosphorous atom can form a heterocyclic ring with the phosphorous atom and X is H or a halide. The conversion takes place under reflux conditions to give a high yield of the amide.Type: GrantFiled: June 7, 1999Date of Patent: October 17, 2000Inventors: Adrian W Parkins, Talit Ghaffar
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Patent number: 6100427Abstract: A process for producing an amide and/or acid from a nitrile comprises introducing a nitrile, as a first reactant, and a hydration compound, as a second reactant which is capable of reacting with the nitrile to convert it to its corresponding amide thus hydrating the nitrile and/or to convert it to its corresponding acid, into a treatment zone. The nitrile is subjected to catalytic distillation in the treatment zone in the presence of the hydration compound, to hydrate at least some of the nitrile to the corresponding amide and/or to form its corresponding acid. The amide and/or acid is withdrawn from the treatment zone.Type: GrantFiled: October 30, 1998Date of Patent: August 8, 2000Assignee: Catalytic Distillation TechnologiesInventors: Barend Christiaan Buurman Bezuidenhout, Zamile Denga, Rian Steyn, Petrus Johannes Steynberg, Nicolaus Ladislaus Stark
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Patent number: 5922912Abstract: A method is disclosed for the concentration of an aqueous acrylamide solution prepared by hydration of acrylonitrile or an aqueous acrylamide solution substantially free of acrylonitrile. The method makes use of a concentration apparatus at least a part of whose solution-contacting section is made of a copper-containing material. The concentration is conducted while introducing an oxygen-containing gas into the apparatus. Use of this method can prevent formation, adhering, accumulation and the like of popcorn polymers inside the concentration apparatus upon concentration of the aqueous acrylamide solution, and can also produce high-quality acrylamide.Type: GrantFiled: April 7, 1997Date of Patent: July 13, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Yoshihiko Kambara, Mutsuo Matsumura, Michiaki Umeno, Yoshikazu Uehara, Koichi Asao
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Patent number: 5811580Abstract: Hydrocarbyl-substituted amides can be prepared in a catalyzed Ritter reaction by contacting a nitrile with a hydrocarbylating agent, in the presence of an acidified clay as the catalyst, under conditions conducive to the formation of the hydrocarbyl-substituted amide.Type: GrantFiled: December 4, 1996Date of Patent: September 22, 1998Assignee: The Lubrizol CorporationInventor: Douglas C. Rhubright
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Patent number: 5712413Abstract: Hydrocarbyl-substituted amides are prepared by a process comprising contacting a nitrile with a hydrocarbylating agent, such as an alkylating agent, in the presence of a catalyst comprising a heteropolyacid or salt thereof.Type: GrantFiled: December 4, 1996Date of Patent: January 27, 1998Assignee: The Lubrizol CorporationInventors: James D. Burrington, Douglas C. Rhubright, Chester E. Ramey
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Patent number: 5534655Abstract: A process for preparing acrylamide is disclosed herein which comprises subjecting acrylonitrile to a hydration reaction in the presence of a copper-based catalyst, said process comprising the step of allowing a compound having an active methylene group and an acidic group in one molecule or a salt of the compound, for example, malonic acid, cyanoacetic acid or its salt to be present in a reaction system. According to the hydration reaction, it is possible to inhibit the secondary formation of impurities which cannot be heretofore removed, without any deterioration of a catalyst activity, and acrylamide can be obtained which is useful as a material for the manufacture of a high-molecular weight flocculant having a sufficiently large molecular weight and a good water solubility.Type: GrantFiled: February 23, 1995Date of Patent: July 9, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoshihiko Kambara, Yoshikazu Uehara, Takeya Abe, Koichi Asao
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Patent number: 5476883Abstract: This invention provides a process for the preparation of acrylamide. Acrylonitrile is treated through at least two purification steps in which acrylonitrile is brought into contact with a strongly-acidic cation exchange resin and then with a resin having primary and/or secondary amino groups or with activated carbon. The resulting acrylonitrile is subjected to hydration in the presence of a copper-base catalyst. The process of this invention can provide high-quality acrylamide even when acrylonitrile of ordinary quality is used, and permits preparation of a polyacrylamide suitable for use in the production of a coagulant having good water solubility or the like.Type: GrantFiled: July 13, 1994Date of Patent: December 19, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Takeya Abe, Yoshihiko Kambara
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Patent number: 5463123Abstract: There is disclosed a process for producing .alpha.-hydroxyisobutyramide by hydration reaction of acetone cyanohydrin in the presence of a catalyst consisting essentially of manganese dioxide which process comprises pretreating the catalyst with a reducing agent. The above process is capable of eliminating the catalyst clogging trouble due to the deposition of the by-produced oxamide and thus proceeding with long-term reaction with the stabilized catalyst performance.Type: GrantFiled: October 12, 1993Date of Patent: October 31, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takako Uchiyama, Hirofumi Higuchi
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Patent number: 5387715Abstract: Alpha-hydroxy-isobutyramide is produced by continuously hydrating acetone cyanohydrin in a liquid phase in the presence of a manganese dioxide catalyst and in the presence of a particular oxide dissolved in water, oxoacid, heteropolyacid or a salt of the acids.Type: GrantFiled: February 1, 1992Date of Patent: February 7, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Minato Karasawa, Masamitsu Inomata, Hiroharu Kageyama, Kanemitsu Miyama
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Patent number: 4906776Abstract: When making an a amide by hydrolysis of a nitrile in an aqueous medium containing a Raney copper catalyst, the yield of amide can be increased and the yield of impurities can be decreased by including vanadium metal in the catalyst. The vanadium may be present as Raney vanadium often as an alloy in the Raney copper.Type: GrantFiled: May 19, 1987Date of Patent: March 6, 1990Assignee: Allied Colloids Ltd.Inventors: Gerald P. Benn, David Farrar, Seraj A. M. Karolia
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Patent number: 4851576Abstract: This invention relates to a process for the catalytic hydrolysis of an .alpha.-aminonitrile in the heterogeneous phase, and to polymeric resins having a catalytic activity for carrying out the present process.The process according to this invention is characterized in that said .alpha.-aminonitrile or one of the salts thereof is reacted in an aqueous medium, in the heterogeneous phase and in the presence of hydroxide ions on a polymeric resin which contains side chains carrying a carbonyl group, and which is insoluble in the aqueous basic medium.Type: GrantFiled: December 28, 1982Date of Patent: July 25, 1989Assignee: Centre National de la Recherche Scientifique (CNRS)Inventors: Auguste A. Commeyras, Jacques R. Taillades, Jean Brugidou, Regine Sola, Aldo Previero, Louis Mion, Robert J. Pascal, Monique Lasperas, Alain Rousset
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Patent number: 4820872Abstract: When making an unsaturated amide by hydrolysis of an unsaturated nitrile in the presence of a catalyst such as Raney copper and an oxidizing agent such as copper nitrate, by-product formation is reduced by including a reagent selected from reducing agents and acids that are substantially non-oxidizing relative to the said oxidizing agent. The preferred reagents are acidic buffers, especially acetic acid and copper acetate. Washing with such a buffer a Raney catalyst or other catalyst that is to be used for catalyzing the hydrolysis of an unsaturated nitrile to an unsaturated amide reduces the temperature surge that otherwise occurs upon addition of the catalyst to the reaction mixture.Type: GrantFiled: March 6, 1986Date of Patent: April 11, 1989Assignee: Allied Colloids Ltd.Inventors: David Farrar, Peter Flesher, Gerald Benn
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Patent number: 4701558Abstract: A method for purifying an aqueous acrylamide solution by using activated carbon is disclosed. The method comprises contacting activated carbon with water having oxygen dissolved therein until the dissolved oxygen concentration in water after the contact increases to at least 0.5 ppm, and then contacting the aqueous acrylamide solution with the thus treated activated carbon. The method can prevent polymerization of acrylamide around activated carbon, and the resulting purified aqueous acrylamide solution requires no further purification, such as ion-exchanging.Type: GrantFiled: November 18, 1985Date of Patent: October 20, 1987Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yasumasa Yamaguchi, Masashi Nishida
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Patent number: 4684751Abstract: A catalytic composition useful for producing amides and primary alcohols from nitriles and alkenes respectively, comprising in the first instance water, a suitable nucleophile, and MHCl[P(R).sub.3 ].sub.2 wherein M is platinum, palladium, or nickel, and R is CH.sub.3, CH.sub.3 CH.sub.2, or i-Pr and in the second instance comprising the same reagents but limited to R being CH.sub.3. The addition of a phase-transfer catalyst facilitates both reactions where the aqueous solubility of the nitriles or alkenes is limiting in the reaction.Type: GrantFiled: February 13, 1986Date of Patent: August 4, 1987Assignee: The Regents of the University of CaliforniaInventors: William C. Trogler, Craig M. Jensen
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Patent number: 4543423Abstract: A nitrile, such as acrylonitrile, is hydrated to the corresponding amide in the presence of a Raney copper catalyst that, before use in the reaction, is partially oxidized by contact with a controlled oxidizing system comprising oxygen, peroxide, iodate, chlorate, bromate or nitrate.Type: GrantFiled: October 28, 1982Date of Patent: September 24, 1985Assignee: Allied Colloids LimitedInventors: David Farrar, Peter Flesher
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Patent number: 4521620Abstract: A method of producing acrylamide from acrylonitrile in the presence of a metallic conversion catalyst which comprises contacting an oil-in-water emulsion of acrylonitrile, said water phase being the continuous phase and containing up to 7% acrylonitrile and said oil phase being the dispersed phase and containing the remaining acrylonitrile to be converted to acrylamide, whereby a substantial portion of the acrylonitrile is converted to acrylamide which remains in the aqueous phase of the oil-in-water emulsion, and then an additional low HLB emulsifier is added to invert the oil-in-water emulsion to a water-in-oil emulsion containing acrylamide.Type: GrantFiled: December 9, 1981Date of Patent: June 4, 1985Assignee: Nalco Chemical CompanyInventor: Kenneth G. Phillips
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Patent number: 4413143Abstract: A method of producing acrylamide from acrylonitrile in the presence of a metallic conversion catalyst which comprises contacting a water-in-oil emulsion of acrylonitrile which is contained in the dispersed aqueous phase of the emulsion under conditions whereby a substantial portion of the acrylonitrile is converted to acrylamide which remains in the aqueous phase of the emulsion.Type: GrantFiled: December 9, 1981Date of Patent: November 1, 1983Assignee: Nalco Chemical CompanyInventors: Kenneth G. Phillips, John G. Premo
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Patent number: 4365090Abstract: In a process for producing acrylamide by hydrating acrylonitrile in the presence of a copper-based catalyst, the reaction is carried out in the presence of 30 to 10,000 ppm of acetone in the reaction solution. According to this process, the activity of the copper-based catalyst is maintained and the economic advantage of acrylamide production is enhanced.Type: GrantFiled: May 18, 1981Date of Patent: December 21, 1982Assignee: Mitsui Toatsu Chemicals, IncorporatedInventor: Shiro Asano
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Patent number: 4365091Abstract: A method for the production of acrylamide by a catalytic hydration of acrylonitrile characterized by using a compound oxide catalyst which is prepared by a precipitation process and represented by the formula,Ti.sub.a X.sub.b Y.sub.c O.sub.dwherein Ti is titanium, X is one of zinc, cadmium and copper, Y is either nickel or lanthanum and the atomic ratios a, b and c are 15 to 98, 2 to 85 and 0 to 20, respectively and d is the number of oxygen atoms satisfying the valence of the other elements.Type: GrantFiled: November 2, 1981Date of Patent: December 21, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Takenaka Masaaki, Tsutomu Takahashi, Tatuya Momobayashi
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Patent number: 4329500Abstract: A process for hydrating a nitrile to the corresponding amide by contacting the nitrile in the presence of water with an essentially insoluble heterogeneous catalyst selected from the group consisting of unreduced and reduced cobalt oxide and unreduced and reduced cobalt-chromium oxide or mixture thereof.Type: GrantFiled: August 7, 1978Date of Patent: May 11, 1982Assignee: The Dow Chemical CompanyInventor: Clarence E. Habermann
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Patent number: 4302597Abstract: In the reaction of conversion of nitriles to amides, more particularly, but not exclusively, acrylonitrile to acrylamide, the improvement consisting in the adoption, as a catalyst, of a copper-based catalyst which is prepared by reacting an organic copper chelate with aluminum-alkyl and/or an aluminum hydride. Higher yields and higher selectivity are obtained over the usual copper-based catalysts.Type: GrantFiled: August 1, 1979Date of Patent: November 24, 1981Assignee: Snamprogetti, S.p.A.Inventors: Giovanni Manara, Vittorio Fattore, Bruno Notari
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Patent number: RE31356Abstract: .[.Aliphatic nitriles.]. .Iadd.Olefinic nitriles of three to six carbon atoms .Iaddend.are converted to the corresponding amides by contacting the nitrile in the presence of water with a cupreous catalyst containing copper prepared by reducing copper hydroxide or a copper salt.Type: GrantFiled: February 26, 1981Date of Patent: August 23, 1983Assignee: The Dow Chemical Co.Inventors: Clarence E. Habermann, Ben A. Tefertiller
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Patent number: RE31430Abstract: Copper, copper oxide, copper-chromium oxide, copper-molybdenum oxide or mixtures thereof have been found to be excellent heterogeneous catalysts for the conversion of nitriles in the presence of water to the corresponding amides. Using one such catalyst in a continuous flow reactor, acrylonitrile was almost 100% converted to acrylamide during more than six weeks of continuous operation.Type: GrantFiled: February 26, 1981Date of Patent: October 25, 1983Assignee: The Dow Chemical Co.Inventors: Clarence E. Habermann, Ben A. Tefertiller
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Patent number: RE32640Abstract: Aliphatic nitriles are converted to the corresponding amides by contacting the nitrile in the presence of water with a cupreous catalyst containing copper metal.Type: GrantFiled: December 23, 1985Date of Patent: April 12, 1988Assignee: The Dow Chemical CompanyInventors: Clarence E. Habermann, Ben A. Tefertiller, Ralph E. Friedrich