Nitro Bonded Directly To Benzene Ring Patents (Class 568/939)
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Patent number: 5099079Abstract: Described herein is a process for separating an acid impurity from a solution containing acid and a nitro substituted aromatic compound by contacting the solution with at least one molten nitrate salt.Type: GrantFiled: July 26, 1990Date of Patent: March 24, 1992Assignee: Olin CorporationInventor: Allen B. Quakenbush
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Patent number: 5099080Abstract: Described herein is a one pot continuous improved process for preparing dinitrotoluene by reacting toluene with concentrated nitric acid.Type: GrantFiled: March 8, 1991Date of Patent: March 24, 1992Assignee: Olin CorporationInventor: Allen B. Quakenbush
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Patent number: 5095157Abstract: In the preparation of 2-chloro-4-nitro-alkylbenzene by reaction of 4-nitro-alkylbenzene with elemental chlorine or chlorine-releasing compounds in the presence of a Friedel-Crafts catalyst in the liquid phase, particularly high selectivities in respect of the target compounds chlorinated exclusively in the 2-position are achieved if a dibenzo-condensed sulphur heterocycle of the formula ##STR1## having the meanings given in the description for R.sup.1 to R.sup.8, X and n, is used as co-catalyst.Type: GrantFiled: May 2, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 5072061Abstract: 1,14-bis(4-nitrophenyl)-1,3,5,7,9,11,13-tetradecaheptaene having the following formula (I): ##STR1## and a method of preparing the above-mentioned 1,14-bis(4-nitrophenyl)-1,3,5,7,9,11,13-tetradecaheptaene having formula (I) by allowing a phosphonium salt having formula (II) to react with 5-(4-nitrophenyl)-2,4-pentadiene-1-al having formula (III) in the presence of a basic catalyst:R.sub.3 P.sup..sym. H.sub.2 C--CH.dbd.CH--CH.sub.2 P.sup..sym. R.sub.3.2X.sup..crclbar.Type: GrantFiled: June 4, 1990Date of Patent: December 10, 1991Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tomoyuki Shimada, Mitsuru Hashimoto
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Patent number: 5072053Abstract: The new 1,3-di-arylmethoxy-4,6-dinitrobenzenes of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another denote hydrogen or C.sub.1 -C.sub.4 -alkyl andAr represents C.sub.6 -C.sub.12 -aryl,can be prepared by reaction of 1,3-dihalogeno-4,6-dinitro-benzenes of the formula ##STR2## in which Hal represents chlorine or bromine, with an arylmethanol of the formulaAr--C(R.sup.1, R.sup.2)OH (IV),in which R.sup.1, R.sup.2 and Ar have the said meaning, and a strong base in the temperature range from 0.degree. to 100.degree. C.These di-arylmethoxy-dinitro-benzenes can be converted into 4,6-diaminoresorcinol by catalytic reduction with hydrogen.Type: GrantFiled: May 21, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Uwe Heinz
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Patent number: 5057632Abstract: Described herein is a continuous process for preparing dinitrotoluene by reacting toluene with dilute nitric acid to produce mononitrotoluene, then reacting the mononitrotoluene with concentrated nitric acid to produce dinitrotoluene.Type: GrantFiled: October 22, 1990Date of Patent: October 15, 1991Assignee: Olin CorporationInventors: Peter C. Imm, Allan B. Quakenbush
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Patent number: 5030776Abstract: Nitrobenzenes are prepared by nitrating benzenes in vapor phase using nitric acid as a nitrating agent and under continuous or intermittent feeding of sulfuric acid as a catalyst in the presence of a catalyst comprising sulfuric acid supported on a carrier or in the presence of only a carrier. This process can provide very high and prolonged nitration activity.Type: GrantFiled: June 6, 1990Date of Patent: July 9, 1991Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Sato, Koichi Nagai, Hiroshi Yoshioka, Yoshihiko Nagaoka
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Patent number: 5012019Abstract: The present invention relates to a process for purifying an aromatic nitration product mixture comprising a nitrated aromatic compound, water, and nitric or sulfuric acid which comprises without regard to sequence: (a) removing at least a portion of said water from said product mixture by contacting and reacting said water in said mixture with magnesium nitrate trihydrate to form magnesium nitrate pentahydrate or magnesium nitrate hexahydrate and removing said magnesium nitrate pentahydrate or magnesium nitrate hexahydrate from said nitrated aromatic compound in said product mixture, and (b) removing at least a portion of said acid from said product mixture by contacting and reacting said acid with an ionic or non-ionic absorbent to form a reacted absorbent and removing said reacted absorbent from said nitrated aromatic compound in said product mixture.Type: GrantFiled: January 26, 1990Date of Patent: April 30, 1991Assignee: Olin CorporationInventors: Robert W. Mason, Peter C. Imm, Paul J. Craney, Thomas W. Offill, Robert T. Brooker
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Patent number: 5006325Abstract: This invention relates to an improved process for the recovery and regeneration of nitric acid from spent acid obtained from the mixed acid nitration of aromatic compounds. In that process a mixed acid of sulfuric acid and nitric acid is contacted with an aromatic composition at a temperature and pressure sufficient for producing a nitroaromatic composition and a spent acid containing unreacted nitric acid, sulfuric acid and solubilized nitroaromatic compounds in said spent acid. The improvement comprises initially heating the spent acid to a temperature of from about 120.degree. to 200.degree. C. for a time sufficient to convert said nitroaromatics in said spent acid to a nitroaromatic composition having a boiling point greater than 300.degree. C. at atmospheric pressure and then flash distilling the hot spent acid containing nitroaromatics compositions at a pressure from about 5 to 15 psia and temperature of 150.degree. to 200.degree. C.Type: GrantFiled: August 28, 1989Date of Patent: April 9, 1991Assignee: Air Products and Chemical, Inc.Inventors: David L. Parks, Jr., Carl J. Martin
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Patent number: 5004846Abstract: Nitrobenzenes are prepared by nitrating benzenes in a vapor phase with dilute or concentrated nitric acid wherein the following (A) or (B) is used as a catalyst:(A) acidic sheet clay minerals ion-exchanged with polyvalent metals, or(B) acidic composite oxides comprising oxides of metals belonging to Group IVA of the Mendeleefs' periodic table and tungsten oxide, molybdenum oxide, niobium oxide or zinc oxide.These catalysts have high catalyst activity and selectivity for vapor phase nitration reaction of benzenes with nitric acid and besides the activity is retained for a long time.Type: GrantFiled: May 15, 1989Date of Patent: April 2, 1991Assignee: Sumitomo Chemical Company, Ltd.Inventors: Hiroshi Sato, Kenichi Hirose, Koichi Nagai, Hiroshi Yoshioka, Yoshihiko Nagaoka
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Patent number: 5001286Abstract: Sulphuric and nitric acids present in dinitrotoluene are separated from the dinitrotoluene by adding up to 10 wt. % water (based on quantity of dinitrotoluene) to the mixture of dinitrotoluene, sulphuric acid and nitric acid, mixing and separating the aqueous phase containing nitric and sulphuric acids. The mixtures treated by this process generally contain up to 5 wt. % nitric acid and up to 6 wt. % sulphuric acid.Type: GrantFiled: February 12, 1988Date of Patent: March 19, 1991Assignee: Bayer AktiengesellschaftInventors: Harro Witt, Heiko Beckhaus
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Patent number: 4987266Abstract: A process is provided for producing nitrophenetole where nitrochlorobenzene is reacted in a cosolvent of a monohydric alcohol and N-alkylpyrrolidone with aqueous alkali metal hydroxide.Type: GrantFiled: December 29, 1989Date of Patent: January 22, 1991Assignee: Monsanto CompanyInventors: Richard J. Day, Harry B. Harlow, Dennis C. Owsley
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Patent number: 4898996Abstract: A process for producing 3-chloro-4-fluoronitrobenzene which is characterized by chlorinating 4-fluoronitrobenzene in the presence of:(1) iodine or an iodide in combination with iron or an iron compound or(2) iodine or an iodide in combination with antimony or an antimony compound.Type: GrantFiled: June 23, 1988Date of Patent: February 6, 1990Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tsukasa Ishikura, Tatuharu Fukushima
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Patent number: 4831193Abstract: This invention relates to a novel process for preparing 3-amino-2-methylbenzotrifluoride from benzotrifluoride. The process comprises nitrating benzotrifluoride to form 3-nitrobenzotrifluoride, reacting this compound with trimethyl sulphoxonium halide to form 3-nitro-2-methylbenzotrifluoride and reducing the nitro group to an amino group.Type: GrantFiled: June 19, 1987Date of Patent: May 16, 1989Assignee: Schering CorporationInventors: Joseph F. Lamendola, Dhiru Vashi, Robert G. Tyson
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Patent number: 4820881Abstract: A process to decolorize and stabilize nitro compounds by contacting the nitro compound with an alkaline earth metal hypochlorite particulate material.Type: GrantFiled: May 24, 1988Date of Patent: April 11, 1989Assignee: W. R. Grace & Co.-Conn.Inventor: Robert J. Kupper
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Patent number: 4804792Abstract: Nitration of benzene or toluene, and more specifically to such a reaction in a molten nitrate salt medium.Type: GrantFiled: January 28, 1988Date of Patent: February 14, 1989Assignee: Olin CorporationInventors: Robert W. Mason, R. K. Steely
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Patent number: 4780559Abstract: A method for the preparation of organic fluorides which comprises reacting a quaternary phosphonium fluoride or bifluoride with an organic substrate having at least one atom or group capable of being replaced by a fluorine atom.Type: GrantFiled: January 1, 1986Date of Patent: October 25, 1988Assignee: Imperial Chemical Industries PLCInventors: Stephen J. Brown, James H. Clark
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Patent number: 4772757Abstract: In the production of nitrobenzene by subjecting benzene to nitration with a mixture of nitric acid and sulfuric acid, separating off the nitrobenzene formed, concentrating the sulfuric acid by evaporation and returning the concentrated sulfuric acid to the bezene nitration stage, the improvement which comprises concentrating sulfuric acid to a concentration of from 75 to 92% by evaporation in vacuo at temperatures in the range from 130.degree. to 195.degree. C. Thereby the energy per kg of water evaporated is drastically reduced compared to processes wherein the sulfuric acid is concentrated to a higher level, without a corresponding loss in efficiency or capacity.Type: GrantFiled: October 21, 1986Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventors: Gunter Lailach, Rudolf Gerken, Karl-Heinz Schultz, Rudolf Hornung, Walter Bockmann, Wolfgang Larbig, Wolfgang Dietz
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Patent number: 4754083Abstract: Para selectivity in the conversion of a monosubstituted benzene containing a meta-directing group to disubstituted benzenes can be substantially enhanced by carrying out the reaction in the gas phase with an inorganic or organic substitution agent in the presence of a catalyst composition comprising a crystalline molecular sieve material. In particular, nitrobenzene can be converted using nitrogen dioxide in the gas phase to a product containing an augmented proportion of para-dinitrobenzene using a wide range of catalyst compositions comprising both synthetic and naturally occurring crystalline molecular sieve materials such as ferrierites, X-type zeolites, Y-type zeolites, silicalite, framework-modified silicalites, ZSM aluminosilicates, AMS-1B borosilicates, and AlPO.sub.4 types.Type: GrantFiled: April 24, 1986Date of Patent: June 28, 1988Assignee: Amoco CorporationInventors: Robert A. Reith, Glen R. Hoff
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Patent number: 4673757Abstract: Carbon-carbon double bonds are hydrogenated selectively in a compound containing a reducible, nitrogen-containing group if the hydrogenation is carried out in the presence of a ruthenium complex catalyst. Also disclosed are new ruthenium complexes for use in such selective hydrogenation.Type: GrantFiled: October 11, 1984Date of Patent: June 16, 1987Assignee: Bayer AktiengesellschaftInventors: Paul Fiedler, Rudolf Braden, Hartmuth Buding
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Patent number: 4663490Abstract: In the production of dinitrotoluene by a two-stage reaction of toluene with nitric acid in the presence of sulphuric acid, wherein toluene is nitrated to mononitrotoluene in the first stage using spent acid from the second stage, and the mononitrotoluene is nitrated to dinitrotoluene in the second stage using concentrated spent acid from the first stage, the improvement which comprises concentrating spent acid under vacuum in an indirectly-heated evaporator and feeding mononitrotoluene into the superheated vapor of the evaporator.Type: GrantFiled: March 12, 1985Date of Patent: May 5, 1987Assignee: Bayer AktiengesellschaftInventors: Rudolf Gerken, Gunter Lailach, Dieter Becher, Harro Witt
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Patent number: 4652400Abstract: Described are 5-nitro-1,1,2,3,3-pentamethyl indane derivatives defined according to the generic structure: ##STR1## wherein R represents hydrogen or methyl and uses thereof in augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, colognes and perfumed articles.Type: GrantFiled: April 11, 1986Date of Patent: March 24, 1987Assignee: International Flavors & Fragrances Inc.Inventor: Mark A. Sprecker
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Patent number: 4650912Abstract: In a method for denitrifying the nitric acid- and nitrous acid-containing spent acid phase from the nitration of an aromatic hydrocarbon by the mixed acid process which comprises forming a denitrification reaction medium by contacting the spent acid phase with an aromatic hydrocarbon under nitration reaction conditions to recover the nitric acid by the formation of a nitroaromatic hydrocarbon, the improvement which comprises(a) adding an amount of aromatic hydrocarbon which is slightly less than or equal to the stoichiometric amount necessary to deplete the spent acid phase of nitric acid,(b) photometrically monitoring the denitrification reaction medium for the appearance of a dark red to black color, and(c) upon detection of such color, adjusting the aromatic hydrocarbon:nitric acid molar ratio in the denitrification reaction medium to eliminate the color by reducing the aromatic hydrocarbon feed rate, or adding nitric acid to the denitrification reaction medium.Type: GrantFiled: March 26, 1985Date of Patent: March 17, 1987Assignee: Air Products and Chemicals, Inc.Inventors: Michael C. Pohl, Richard V. C. Carr, John E. Sawicki
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Patent number: 4628131Abstract: Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compounds with a nitrating agent in the presence of a nitration promoting catalyst composition represented by the empirical formula:(M.sup.1.sub.a M.sup.2.sub.b O.sub.c).sub.x (NO.sub.2).sub.ywherein M.sup.1 is at least one element selected from Group 4b of the Periodic Table of the Elements, M.sup.2 is at least one element selected from Group 3b of the Periodic Table of the Elements, a is 1, b is 0 to 20, c is a number taken to satisfy the average valences of M.sup.1 and M.sup.2 in the oxidation states in which they exist in the composition, x is 1, and y is 0 to c.Type: GrantFiled: November 14, 1984Date of Patent: December 9, 1986Assignee: Monsanto CompanyInventor: Ignatius Schumacher
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Patent number: 4620047Abstract: An adsorptive separation process for separating ortho-nitrotoluene from a feed mixture comprising the ortho-isomer and at least one other isomer of nitrotoluene. The process comprises contacting the feed mixture with an adsorbent comprising a type X zeolite, containing at the exchangeable cationic sites cations of metals from Group IA or IIA of the Periodic Table of Elements, selectively adsorbing substantially all of the ortho-nitrotoluene to the substantial exclusion of the remaining isomers, removing the non-adsorbed portion of the feed mixture from contact with the adsorbent, and thereafter recovering high-purity ortho-isomer by desorption with nitrobenzene.Type: GrantFiled: October 18, 1984Date of Patent: October 28, 1986Assignee: UOP Inc.Inventor: Hermann A. Zinnen
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Patent number: 4618733Abstract: Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compounds with a nitrating agent in the presence of a nitration promoting catalyst comprising the adduct of a Group 4b-Group 3b metal oxide composition represented by the empirical formula:(M.sup.1.sub.a M.sup.2.sub.b O.sub.c).sub.x (NO.sub.2).sub.ywherein M.sup.1 is at least one element selected from Group 4b of the Periodic Table of the Elements, M.sup.2 is at least one element selected from Group 3b of the Periodic Table of the Elements, a is 1, b is 0 to 20, c is a number taken to satisfy the average valences of M.sup.1 and M.sup.2 in the oxidation states in which they exist in the composition, x is 1, and y is 0 to c, and a catalytically effective amount of sulfur trioxide. Such catalysts are particularly effective to catalyze the vapor phase nitration of chlorobenzene and are characterized in such reaction by providing a para/ortho isomer distribution ratio of at least about 2/1.Type: GrantFiled: November 14, 1984Date of Patent: October 21, 1986Assignee: Monsanto CompanyInventor: Ignatius Schumacher
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Patent number: 4600702Abstract: Catalysts compositions useful to catalyze the nitration of aromatic compounds in the vapor phase to produce nitroaromatic compounds are represented by the empirical formula:(M.sup.1.sub.a M.sup.2.sub.b O.sub.c).sub.x (NO.sub.2).sub.ywherein M.sup.1 is at least one element selected from Group 4b of the Periodic Table of the Elements, M.sup.2 is at least one element selected from Group 3b of the Periodic Table of the Elements, a is 1, b is 0.050 to 20, c is a number taken to satisfy the average valences of M.sup.1 and M.sup.2 in the oxidation states in which they exist in the composition, x is 1, and y is 0 to c. The compositions are particularly effective to catalyze the vapor phase nitration of chlorobenzene and are characterized in such reaction by providing a para/ortho isomer distribution ratio of at least about 1.9/l.Type: GrantFiled: November 14, 1984Date of Patent: July 15, 1986Assignee: Monsanto CompanyInventor: Ignatius Schumacher
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Patent number: 4590263Abstract: Novel diazonium salts which possess excellent photo speed, good thermal stability, exceptional resistance to discoloration in the D.sub.min areas, rapid development, and allow a wide range of azo dye colors are provided. The diazonium salts are of the following formula: ##STR1## wherein R.sub.1 is tertiary butyl or tertiary amyl; Y is hydrogen, alkyl, hydroxyalkyl, cyanoalkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, aralkoxy, aralkylthio, arylthio, alkylthio, halogen, allyl, allyloxy, allylthio, cyanoalkoxy, hydroxyalkoxy, methoxyalkoxy, trifluoroalkyl, alkylacetylamino, morpholino, or dialkyl carbonamido;R.sub.2 and R.sub.3 are the same or different, and are alkyl, aralkyl, allyl, cyanoalkyl, hydroxyalkyl, hydrogen, acyl, cycloalkyl, beta-chloroalkyl, branched alkyl, or a structure wherein R.sub.2 and R.sub.3 may be linked together to form a heterocyclic structure; andX is an anion.Type: GrantFiled: September 30, 1982Date of Patent: May 20, 1986Assignee: James River Graphics, Inc.Inventors: Robert C. Desjarlais, Everett W. Bennett
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Patent number: 4554360Abstract: Provided is a process for converting an aromatic compound to prepare an iodoarene, Ar--I, and an aryl compound which is a compound wherein an unsaturated compound is bonded directly to an aryl group, Ar, which process comprises reacting a diaryliodonium salt represented by general formula (I)[Ar--I.sup..sym. --Ar]X.sup..crclbar. (I)wherein Ar is an aryl group which may be substituted and two Ar's are identical and X.sup..crclbar. is a counter ion inert to the reaction with the unsaturated compound in a solvent in the presence of a transition metal catalyst and a base or a reducing metal, said reaction being carried out at a temperature not higher than 80.degree. C. and/or by using at least one of the base, the reducing metal and the unsaturated compound in an amount not more than 1.Type: GrantFiled: March 29, 1984Date of Patent: November 19, 1985Assignee: Nippon Petrochemicals Company, LimitedInventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
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Patent number: 4551568Abstract: Benzene is efficiently nitrated in gaseous phase with NO.sub.2 or N.sub.2 O.sub.4 in the presence of a catalyst of acidic mixed oxide containing two or more sorts of metal oxides, for example, MoO.sub.3 --WO.sub.3, MoO.sub.3 --TiO.sub.2, WO.sub.3 --TiO.sub.2, TiO.sub.2 --ZnO or TiO.sub.2 --SiO.sub.2.Type: GrantFiled: April 15, 1983Date of Patent: November 5, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Sato, Shuzo Nakamura
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Patent number: 4496782Abstract: A method is provided for denitrifying the aqueous spent acid of mononitration. The nitric acid in the aqueous spent acid is recovered by adiabatically reacting greater than a stoichiometric amount of a mononitroaromatic hydrocarbon with the aqueous spent acid which has been fortified to a nitric acid concentration of at least about 2 wt %. The denitrification method is useful in treating the aqueous spent acid phase from the mononitration stage of a dinitrotoluene process.Type: GrantFiled: July 8, 1983Date of Patent: January 29, 1985Assignee: Air Products and Chemicals, Inc.Inventor: Richard V. C. Carr
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Patent number: 4469904Abstract: A process for selectively forming nitro compounds by contacting, at elevated temperature and pressure and in a homogeneous gas phase, an organic carboxylic acid having from two to ten carbon atoms with NO.sub.2 or HNO.sub.3 alone or in the presence of oxygen and/or water.Type: GrantFiled: July 5, 1983Date of Patent: September 4, 1984Assignee: W. R. Grace & Co.Inventors: Shu-Chieh P. Wang, Martin B. Sherwin
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Patent number: 4465876Abstract: In a process for nitrating aromatics using lower valent nitrating agents in trifluoroacetic acid, the product yield of nitroarenes can be significantly increased by maintaining an excess of nitrating agent over the stoichiometric amount during the reaction.Type: GrantFiled: February 7, 1983Date of Patent: August 14, 1984Assignee: Air Products and Chemicals, Inc.Inventor: Barton Milligan
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Patent number: 4447662Abstract: Aromatic hydrocarbons are nitrated by reacting the aromatic hydrocarbon in a nitrogen tetroxide-containing liquid reaction medium, in the presence of a beta-dicarbonyl compound having a "W" configuration with a carbonyl group at each apex of the "W", preferably at a pressure and temperature sufficient to maintain the nitrogen tetroxide in the liquid state. Addition of an inert organic co-solvent to the liquid nitrogen tetroxide for the metal acetylacetonate promoted nitration of benzene essentially eliminates the production of dinitrobenzenes.Type: GrantFiled: June 10, 1982Date of Patent: May 8, 1984Assignee: Air Products and Chemicals, Inc.Inventors: David S. Ross, Robert M. Johnson, Jr., Ripudaman Malhotra
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Patent number: 4426543Abstract: Aromatic hydrocarbons selected from the group consisting of benzene and toluene are nitrated in the vapor phase at temperatures between about 80.degree. C. and about 190.degree. C. in the presence of a molecular sieve catalyst.Type: GrantFiled: February 17, 1982Date of Patent: January 17, 1984Assignee: Monsanto CompanyInventors: Ignatius Schumacher, Kang-Bo Wang
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Patent number: 4418230Abstract: Nitration of aromatics wherein gasified aromatic compounds and nitric acid are contacted with a silicon-aluminum catalyst.Type: GrantFiled: January 11, 1982Date of Patent: November 29, 1983Assignee: Aktiebolaget BoforsInventors: Jan Bakke, Jermund Liaskar
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Patent number: 4417080Abstract: Aromatic hydrocarbons are nitrated by reacting the aromatic hydrocarbon in a nitrogen tetroxide-containing liquid reaction medium, in the presence of a beta-dicarbonyl compound having a "W" configuration with a carbonyl group at each apex of the "W", such as a metal acetylacetonate, preferably at a pressure and temperature sufficient to maintain the nitrogen tetroxide in the liquid state. Addition of an inert organic co-solvent to the liquid nitrogen tetroxide for the metal acetylacetonate promoted nitration of benzene essentially eliminates the production of dinitrobenzenes.Type: GrantFiled: June 10, 1982Date of Patent: November 22, 1983Assignee: Air Products and Chemicals, Inc.Inventors: David S. Ross, Robert M. Johnson, Jr., Ripudaman Malhotra
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Patent number: 4415744Abstract: Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compound with a nitrating agent in the presence of a nitration promotion catalyst which comprises the adduct of:(a) an alumina-silica-metal oxide combination represented by the formula:(Al.sub.2 O.sub.3).sub.a (SiO.sub.2).sub.b (M.sub.2/n O).sub.cwherein M is a metal cation selected from the group consisting of the lanthanides or rare earths, Groups 1b, 2b, 5b, 6b, 7b, and 8 of the Periodic Table of the Elements, and mixtures thereof, and a, b, and c represent weight percent of the Al.sub.2 O.sub.3, SiO.sub.2, and M.sub.2/n O components, respectively, in the alumina-silica-metal oxide combination, with a being 0 to 100, b being 0 to 100, and c being 0 to 50, and n represents an integer from 1 to 7 of the valence of the metal cation, with the proviso that the sum of (a+b) must be greater than 0, and(b) a catalytically effective amount of sulfur trioxide.Type: GrantFiled: October 21, 1981Date of Patent: November 15, 1983Assignee: Monsanto CompanyInventors: Ignatius Schumacher, Kang-Bo Wang
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Patent number: 4395372Abstract: A process is disclosed for alkylation of benzenes with lower olefins which comprises contacting the benzene and lower olefin with a rare earth exchanged X or Y zeolite catalyst in the presence of sulfur dioxide.Type: GrantFiled: August 9, 1982Date of Patent: July 26, 1983Assignee: Shell Oil CompanyInventors: Robert Q. Kluttz, Lynn H. Slaugh
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Patent number: 4392978Abstract: A method and reagent for the selective nitration of aromatic hydrocarbons which comprises contacting a complex of at least a catalytic amount of a polyether with a nitronium containing substance, e.g., NO.sub.2 BF.sub.4 with an aromatic hydrocarbon, e.g., toluene with at least one replaceable hydrogen. Nitration of toluene with these complexes at ambient temperature resulted in a reduction in meta substitution. In competitive studies, soluble crown ether complexes of NO.sub.2 BF.sub.4 in CH.sub.2 Cl.sub.2 nitrated toluene 45-59 times faster than they nitrated benzene.Type: GrantFiled: December 26, 1979Date of Patent: July 12, 1983Assignee: Allied CorporationInventors: Ronald L. Elsenbaumer, Edel Wasserman
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Patent number: 4382891Abstract: Fluoroalkoxysulfur fluorides of the formula ##STR1## wherein R is H, CH.sub.3, CF.sub.3, or C.sub.2 F.sub.5, and n is 1 or 2, used as fluorinating agents to replace OH groups in organic molecules with F and halocarbon solutions of lithium fluoroalkoxides.Type: GrantFiled: October 5, 1981Date of Patent: May 10, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: William J. Middleton
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Patent number: 4371721Abstract: A process for selective cracking of 1,4-disubstituted benzene compounds having at least one polar substituent. Mixtures containing isomers of such a compound are brought into contact with a specified type of shape selective crystalline zeolite catalyst under conditions of temperature and pressure conducive to reaction of said benzene compound, thereby selectively reacting the 1,4-disubstituted isomer in preference to the 1,2- and 1,3-disubstituted isomers of said polar benzene compound. The shape selective zeolite catalysts employed herein are crystalline zeolites characterized by a silica to alumina ratio of at least about 12 and a constraint index within the approximate range of 1 to 12.Type: GrantFiled: September 25, 1981Date of Patent: February 1, 1983Assignee: Mobil Oil CorporationInventor: Margaret M. Wu
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Patent number: 4347389Abstract: Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compound with a nitrating agent in the presence of a nitration promoting catalyst comprising a phosphorus-vanadium-oxygen complex.Type: GrantFiled: December 31, 1980Date of Patent: August 31, 1982Assignee: Monsanto CompanyInventors: Ignatius Schumacher, Kang-bo Wang
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Patent number: 4346040Abstract: The invention relates to a process for converting an aldehyde into a corresponding alkene and of the type wherein the aldehyde is placed in the presence of a phosphoric reagent and a base in solution in an organic aprotic solvent; the process comprising using a mineral base evincing in an aqueous medium a basic force less than or equal to that of the hydroxide ion or a strongly basic organic base of the nitrogen compounds family and adjusting the hydration rate of the reaction medium in such a manner that there are about 0.5 to 5 moles of water per mole of aldehyde.Type: GrantFiled: July 21, 1981Date of Patent: August 24, 1982Assignee: Agrifurane S.A.Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
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Patent number: 4339618Abstract: The invention relates to a process for the production of nitroaryl compounds which are at least monosubstituted, by nitration of aryl compounds which are at least monosubstituted, which process comprises carrying out the nitration in a two-phase system which consists of an inorganic phase consisting of sulfuric acid having a concentration of at least 80% and an organic phase consisting of an inert organic liquid in which the nitration product is almost insoluble in the presence of sulfuric acid, at a temperature in the range from -30.degree. to 100.degree. C., with nitric acid as nitrating agent.The novel process can be generally employed for aryl compounds which are at least monosubstituted. The corresponding nitroaryl compounds are obtained in high yield and isomeric purity.Type: GrantFiled: June 17, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy AGInventor: Manfred Rosner
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Patent number: 4334111Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.Type: GrantFiled: February 17, 1978Date of Patent: June 8, 1982Assignee: The Dow Chemical CompanyInventors: Ralph A. Davis, R. Garth Pews
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Patent number: 4331819Abstract: The invention relates to a process for the preparation of nitrated aromatic compounds by the mixed acid process, in which water is removed from the reaction mass by passing an inert gas through it.Type: GrantFiled: April 24, 1980Date of Patent: May 25, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert McCall
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Patent number: 4328168Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of a cyclic polyether compound and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.Type: GrantFiled: October 27, 1980Date of Patent: May 4, 1982Assignee: Emery Industries, Inc.Inventor: Richard G. Fayter, Jr.
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Patent number: 4311651Abstract: Fluoroalkoxysulfur fluorides of the formula ##STR1## wherein R is H, CH.sub.3, CF.sub.3, or C.sub.2 F.sub.5, and n is 1 or 2; their preparation by reaction of lithium fluoroalkoxides with sulfur tetrafluoride; their use as fluorinating agents to replace OH groups in organic molecules with F; and halocarbon solutions of lithium fluoroalkoxides.Type: GrantFiled: May 9, 1980Date of Patent: January 19, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: William J. Middleton
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Patent number: 4310500Abstract: In the nitration of a volatile aromatic compound wherein the compound is reacted with a liquid nitrating agent thereby to effect nitration and to produce a waste gas containing some of the aromatic compound, nitrogen oxides and nitric acid, the improvement which comprises contacting the waste gas with fresh nitrating agent thereby to remove the aromatic compound from the gas into the nitrating agent, and thereafter using such nitrating agent to effect subsequent nitration.Type: GrantFiled: May 1, 1980Date of Patent: January 12, 1982Assignee: Josef Meissner GmbH & Co.Inventors: Gerhard Langecker, Hans-Jurgen Gebauer, Heinrich Hermann