Nitro Bonded Directly To Benzene Ring Patents (Class 568/939)
  • Patent number: 5099078
    Abstract: Described herein is a one pot continuous process for preparing dinitrotoluene by reacting toluene with concentrated nitric acid.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: March 24, 1992
    Assignee: Olin Corporation
    Inventor: Allen B. Quakenbush
  • Patent number: 5099079
    Abstract: 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: Grant
    Filed: July 26, 1990
    Date of Patent: March 24, 1992
    Assignee: Olin Corporation
    Inventor: Allen B. Quakenbush
  • Patent number: 5095157
    Abstract: 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: Grant
    Filed: May 2, 1990
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 5072053
    Abstract: 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: Grant
    Filed: May 21, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Uwe Heinz
  • Patent number: 5072061
    Abstract: 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: Grant
    Filed: June 4, 1990
    Date of Patent: December 10, 1991
    Assignee: Ricoh Company, Ltd.
    Inventors: Masaomi Sasaki, Tomoyuki Shimada, Mitsuru Hashimoto
  • Patent number: 5057632
    Abstract: 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: Grant
    Filed: October 22, 1990
    Date of Patent: October 15, 1991
    Assignee: Olin Corporation
    Inventors: Peter C. Imm, Allan B. Quakenbush
  • Patent number: 5030776
    Abstract: 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: Grant
    Filed: June 6, 1990
    Date of Patent: July 9, 1991
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Hiroshi Sato, Koichi Nagai, Hiroshi Yoshioka, Yoshihiko Nagaoka
  • Patent number: 5012019
    Abstract: 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: Grant
    Filed: January 26, 1990
    Date of Patent: April 30, 1991
    Assignee: Olin Corporation
    Inventors: Robert W. Mason, Peter C. Imm, Paul J. Craney, Thomas W. Offill, Robert T. Brooker
  • Patent number: 5006325
    Abstract: 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: Grant
    Filed: August 28, 1989
    Date of Patent: April 9, 1991
    Assignee: Air Products and Chemical, Inc.
    Inventors: David L. Parks, Jr., Carl J. Martin
  • Patent number: 5004846
    Abstract: 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: Grant
    Filed: May 15, 1989
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Hiroshi Sato, Kenichi Hirose, Koichi Nagai, Hiroshi Yoshioka, Yoshihiko Nagaoka
  • Patent number: 5001286
    Abstract: 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: Grant
    Filed: February 12, 1988
    Date of Patent: March 19, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Harro Witt, Heiko Beckhaus
  • Patent number: 4987266
    Abstract: 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: Grant
    Filed: December 29, 1989
    Date of Patent: January 22, 1991
    Assignee: Monsanto Company
    Inventors: Richard J. Day, Harry B. Harlow, Dennis C. Owsley
  • Patent number: 4898996
    Abstract: 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: Grant
    Filed: June 23, 1988
    Date of Patent: February 6, 1990
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tsukasa Ishikura, Tatuharu Fukushima
  • Patent number: 4831193
    Abstract: 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: Grant
    Filed: June 19, 1987
    Date of Patent: May 16, 1989
    Assignee: Schering Corporation
    Inventors: Joseph F. Lamendola, Dhiru Vashi, Robert G. Tyson
  • Patent number: 4820881
    Abstract: A process to decolorize and stabilize nitro compounds by contacting the nitro compound with an alkaline earth metal hypochlorite particulate material.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: April 11, 1989
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Robert J. Kupper
  • Patent number: 4804792
    Abstract: Nitration of benzene or toluene, and more specifically to such a reaction in a molten nitrate salt medium.
    Type: Grant
    Filed: January 28, 1988
    Date of Patent: February 14, 1989
    Assignee: Olin Corporation
    Inventors: Robert W. Mason, R. K. Steely
  • Patent number: 4780559
    Abstract: 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: Grant
    Filed: January 1, 1986
    Date of Patent: October 25, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Stephen J. Brown, James H. Clark
  • Patent number: 4772757
    Abstract: 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: Grant
    Filed: October 21, 1986
    Date of Patent: September 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Lailach, Rudolf Gerken, Karl-Heinz Schultz, Rudolf Hornung, Walter Bockmann, Wolfgang Larbig, Wolfgang Dietz
  • Patent number: 4754083
    Abstract: 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: Grant
    Filed: April 24, 1986
    Date of Patent: June 28, 1988
    Assignee: Amoco Corporation
    Inventors: Robert A. Reith, Glen R. Hoff
  • Patent number: 4673757
    Abstract: 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: Grant
    Filed: October 11, 1984
    Date of Patent: June 16, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Paul Fiedler, Rudolf Braden, Hartmuth Buding
  • Patent number: 4663490
    Abstract: 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: Grant
    Filed: March 12, 1985
    Date of Patent: May 5, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Gerken, Gunter Lailach, Dieter Becher, Harro Witt
  • Patent number: 4652400
    Abstract: 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: Grant
    Filed: April 11, 1986
    Date of Patent: March 24, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Mark A. Sprecker
  • Patent number: 4650912
    Abstract: 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: Grant
    Filed: March 26, 1985
    Date of Patent: March 17, 1987
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael C. Pohl, Richard V. C. Carr, John E. Sawicki
  • Patent number: 4628131
    Abstract: 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: Grant
    Filed: November 14, 1984
    Date of Patent: December 9, 1986
    Assignee: Monsanto Company
    Inventor: Ignatius Schumacher
  • Patent number: 4620047
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: October 28, 1986
    Assignee: UOP Inc.
    Inventor: Hermann A. Zinnen
  • Patent number: 4618733
    Abstract: 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: Grant
    Filed: November 14, 1984
    Date of Patent: October 21, 1986
    Assignee: Monsanto Company
    Inventor: Ignatius Schumacher
  • Patent number: 4600702
    Abstract: 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: Grant
    Filed: November 14, 1984
    Date of Patent: July 15, 1986
    Assignee: Monsanto Company
    Inventor: Ignatius Schumacher
  • Patent number: 4590263
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: May 20, 1986
    Assignee: James River Graphics, Inc.
    Inventors: Robert C. Desjarlais, Everett W. Bennett
  • Patent number: 4554360
    Abstract: 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: Grant
    Filed: March 29, 1984
    Date of Patent: November 19, 1985
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
  • Patent number: 4551568
    Abstract: 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: Grant
    Filed: April 15, 1983
    Date of Patent: November 5, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Sato, Shuzo Nakamura
  • Patent number: 4496782
    Abstract: 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: Grant
    Filed: July 8, 1983
    Date of Patent: January 29, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Richard V. C. Carr
  • Patent number: 4469904
    Abstract: 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: Grant
    Filed: July 5, 1983
    Date of Patent: September 4, 1984
    Assignee: W. R. Grace & Co.
    Inventors: Shu-Chieh P. Wang, Martin B. Sherwin
  • Patent number: 4465876
    Abstract: 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: Grant
    Filed: February 7, 1983
    Date of Patent: August 14, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Barton Milligan
  • Patent number: 4447662
    Abstract: 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: Grant
    Filed: June 10, 1982
    Date of Patent: May 8, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventors: David S. Ross, Robert M. Johnson, Jr., Ripudaman Malhotra
  • Patent number: 4426543
    Abstract: 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: Grant
    Filed: February 17, 1982
    Date of Patent: January 17, 1984
    Assignee: Monsanto Company
    Inventors: Ignatius Schumacher, Kang-Bo Wang
  • Patent number: 4418230
    Abstract: Nitration of aromatics wherein gasified aromatic compounds and nitric acid are contacted with a silicon-aluminum catalyst.
    Type: Grant
    Filed: January 11, 1982
    Date of Patent: November 29, 1983
    Assignee: Aktiebolaget Bofors
    Inventors: Jan Bakke, Jermund Liaskar
  • Patent number: 4417080
    Abstract: 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: Grant
    Filed: June 10, 1982
    Date of Patent: November 22, 1983
    Assignee: Air Products and Chemicals, Inc.
    Inventors: David S. Ross, Robert M. Johnson, Jr., Ripudaman Malhotra
  • Patent number: 4415744
    Abstract: 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: Grant
    Filed: October 21, 1981
    Date of Patent: November 15, 1983
    Assignee: Monsanto Company
    Inventors: Ignatius Schumacher, Kang-Bo Wang
  • Patent number: 4395372
    Abstract: 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: Grant
    Filed: August 9, 1982
    Date of Patent: July 26, 1983
    Assignee: Shell Oil Company
    Inventors: Robert Q. Kluttz, Lynn H. Slaugh
  • Patent number: 4392978
    Abstract: 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: Grant
    Filed: December 26, 1979
    Date of Patent: July 12, 1983
    Assignee: Allied Corporation
    Inventors: Ronald L. Elsenbaumer, Edel Wasserman
  • Patent number: 4382891
    Abstract: 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: Grant
    Filed: October 5, 1981
    Date of Patent: May 10, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William J. Middleton
  • Patent number: 4371721
    Abstract: 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: Grant
    Filed: September 25, 1981
    Date of Patent: February 1, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Margaret M. Wu
  • Patent number: 4347389
    Abstract: 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: Grant
    Filed: December 31, 1980
    Date of Patent: August 31, 1982
    Assignee: Monsanto Company
    Inventors: Ignatius Schumacher, Kang-bo Wang
  • Patent number: 4346040
    Abstract: 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: Grant
    Filed: July 21, 1981
    Date of Patent: August 24, 1982
    Assignee: Agrifurane S.A.
    Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
  • Patent number: 4339618
    Abstract: 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: Grant
    Filed: June 17, 1980
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy AG
    Inventor: Manfred Rosner
  • Patent number: 4334111
    Abstract: 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: Grant
    Filed: February 17, 1978
    Date of Patent: June 8, 1982
    Assignee: The Dow Chemical Company
    Inventors: Ralph A. Davis, R. Garth Pews
  • Patent number: 4331819
    Abstract: 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: Grant
    Filed: April 24, 1980
    Date of Patent: May 25, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert McCall
  • Patent number: 4328168
    Abstract: 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: Grant
    Filed: October 27, 1980
    Date of Patent: May 4, 1982
    Assignee: Emery Industries, Inc.
    Inventor: Richard G. Fayter, Jr.
  • Patent number: 4311651
    Abstract: 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: Grant
    Filed: May 9, 1980
    Date of Patent: January 19, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William J. Middleton
  • Patent number: 4310500
    Abstract: 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: Grant
    Filed: May 1, 1980
    Date of Patent: January 12, 1982
    Assignee: Josef Meissner GmbH & Co.
    Inventors: Gerhard Langecker, Hans-Jurgen Gebauer, Heinrich Hermann