Patents Examined by D. Horwitz
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Patent number: 3962342Abstract: The .alpha.-bromo-substituted or unsubstituted-4-pivaloyl toluenes, e.g., .alpha.-bromo-4-pivaloyl toluene, are prepared by bromination of a corresponding p-pivaloyl toluene with liquid bromine at a temperature of at least 100.degree.C.Type: GrantFiled: March 24, 1975Date of Patent: June 8, 1976Assignee: Sandoz, Inc.Inventors: Jerome Linder, William J. Houlihan
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Patent number: 3962356Abstract: 1,1-Di(p-substituted phenyl)-2,2-dichlorocyclopropanes, wherein the phenyl substituted are alkyl or alkoxy, as new compounds insecticides.Type: GrantFiled: August 15, 1974Date of Patent: June 8, 1976Assignee: Monsanto Chemicals LimitedInventor: George Holan
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Patent number: 3962357Abstract: An improved continous single step vapor phase process for the preparation of substituted vinylbenzyl chloride from substituted ethyltoluene is disclosed. In this process a substituted ethyltoluene is reacted with a halogen gas in the vapor phase, at elevated temperatures via a continuous feed process. Furthermore, this process achieves halogenation followed by dehydrohalogenation in a single pass through the reactor. There is also obtained a very high total selectivity to vinylbenzyl chloride and its precursors via this continuous process.Type: GrantFiled: July 1, 1974Date of Patent: June 8, 1976Assignee: Rohm and Haas CompanyInventors: Richard F. Merritt, Clark R. Carpenter
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Patent number: 3960962Abstract: Aromatic hydroxy compounds (e.g., 2,6-dimethylphenol) are converted to the corresponding aromatic amine (e.g., 2,6-dimethylaniline) by reaction with ammonia at elevated temperatures in the presence of a cyclohexanone promoter and a catalyst comprising metallic palladium bonded to a phosphinated polystyrene resin.Type: GrantFiled: May 31, 1974Date of Patent: June 1, 1976Assignee: Ethyl CorporationInventor: Ronald L. Shubkin
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Patent number: 3960974Abstract: This invention concerns 2,3,5,6-dibenzobicyclo-[5.1.0]octanes which may be substituted at the 4-position by either halogen, ketonic oxygen or hydroxyl. These compounds are prepared from 5H-dibenzo[a,d]cyclohepten-5-one by reaction with ethyl trichloroacetate in the presence of sodium methoxide to give 8,8-dichloro-2,3,5,6-dibenzobicyclo[5.1.0]octan-4-one which is reduced to the corresponding 4-hydroxy compound. The resulting 4-hydroxy compound is dehalogenated and converted to the corresponding 4-chloro or 4-keto compound. The 4-substituted compounds are useful in preparing other compounds of our invention.4-Dialkylaminopropylidenedibenzobicyclo[5.1.0]-octane compounds and 4-dialkylaminopropyldibenzobicyclo[5.1.0]octane compounds, useful as antidepressant agents, are prepared from, respectively, dibenzobicyclo[5.1.0]-octan-4-one by reaction with a dialkylaminopropyl Grignard reagent followed by dehydration of the resulting carbinol or by reaction of a 4-halo-2,3,5,6-dibenzobicyclo[5.1.Type: GrantFiled: January 14, 1975Date of Patent: June 1, 1976Assignee: Merck & Co., Inc.Inventors: Edward L. Engelhardt, David C. Remy
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Patent number: 3959400Abstract: A process is provided for dimerization of light olefins comprising from 2 to 4 carbon atoms which comprises contacting same at a weight hourly space velocity of from about 0.1 to about 10, a temperature of from about 32.degree.F to about 350.degree.F and a pressure of from about 200 psig to about 1000 psig with a catalyst of alumina having intimately combined therewith from about 2 to about 5 weight percent nickel and from about 1 to about 3 weight percent sulfur as a result of impregnation with nickel sulfate, said alumina being gamma, eta or a mixture thereof and said catalyst having been calcined at a temperature of from 750.degree.F to about 1150.degree.F in an inert oxygen-free, non-reducing atmosphere.Type: GrantFiled: December 23, 1974Date of Patent: May 25, 1976Assignee: Mobil Oil CorporationInventor: Stanley J. Lucki
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Patent number: 3959374Abstract: A process is described for the preparation of mixed isomeric methylene-bridged polycyclohexylpolyamines wherein a mixed isomeric methylene-bridged polyphenyl polyamine mixture having a functionality of from about 2.0 to about 3.3 is pretreated by contacting the mixture and hydrogen with a nickel-containing hydrogenation catalyst at a temperature of from about 25.degree.C. to about 250.degree.C. under a pressure of about 500 to about 15,000 psig. The pretreated isomeric polyamine is then hydrogenated in the presence of ammonia under conventional hydrogenation conditions employing a ruthenium-containing hydrogenation catalyst. The pretreatment step allows the utilization of mixed isomeric methylene-bridged polyphenyl polyamine feed mixtures for the production of isomeric methylene-bridged polycyclohexylpolyamines in high yields without attendant deactivation of the ruthenium hydrogenation catalyst heretofore observed. The process is particularly applicable to continuous operation.Type: GrantFiled: May 30, 1974Date of Patent: May 25, 1976Assignee: Jefferson Chemical Company, Inc.Inventors: Michael E. Brennan, Ernest L. Yeakey
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Patent number: 3957875Abstract: A process is disclosed which comprises reacting trimethylamine with 2-[2-(N,N-dimethylamino)ethoxy]ethanol in the presence of nickel catalyst to produce bis[2-(N,N-dimethylamino)ethyl] ether.Type: GrantFiled: June 10, 1974Date of Patent: May 18, 1976Assignee: Union Carbide CorporationInventors: John Lee Ferrell, Fedor Poppelsdorf
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Patent number: 3957874Abstract: An improved process for the continuous production of N-alkylarylamines by reaction of arylamines with alkanols and/or dialkyl ethers in the gas phase at a temperature of from 180.degree. to 450.degree.C in the presence of carrier substances which contain an oxyacid of phosphorus. The improvement consists in using silicic acid having an internal surface area of from 50 to 500 square meters per gram and a content of from 0.1 to 20% by weight of phosphoric acid and in the continuous supply of phosphoric acid and/or an alkyl phosphate to the catalyst during the reaction. N-alkylarylamines are starting materials for the production of dyes, pesticides, plant protection agents and growth regulators. They are also suitable as additives to mineral oils or to coating compositions and other polymerized systems.Type: GrantFiled: July 10, 1974Date of Patent: May 18, 1976Assignee: BASF AktiengesellschaftInventors: Toni Dockner, Herbert Krug
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Patent number: 3957893Abstract: The tendency for methyl chloroform to decompose in the presence of metals, particularly aluminum, is inhibited by a stabilizer mixture comprising an epoxide, a nitroalkane and either propylene glycol mono-methyl ether, dioxepane or a mixture thereof.Type: GrantFiled: March 28, 1974Date of Patent: May 18, 1976Assignee: Diamond Shamrock CorporationInventors: Norman L. Beckers, Edward A. Rowe
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Patent number: 3957900Abstract: Method for dehydrating diols into diolefins and/or olefin alcohols by contacting said diols under dehydration conditions with a catalyst prepared by forming an intimate mixture of finely divided solid particles of at least one pyrophosphate and at least one acid orthophosphate of at least one metal belonging to the group consisting of lithium, sodium, strontium, and barium into a formed mass which is thereafter calcined to transform the acid orthophosphate into pyrophosphate.Type: GrantFiled: January 21, 1975Date of Patent: May 18, 1976Assignee: Compagnie Francaise de RaffinageInventors: Joseph Edouard Weisang, Georges Szabo, Jean Maurin
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Patent number: 3956412Abstract: Liquid perfluoroalkyl iodides are added to halogenated gaseous olefins in the presence of free radical generating catalysts. The gaseous olefin is bubbled through liquid perfluoroalkyl iodide and catalyst at temperatures of 50.degree. to 220.degree.C, and pressures no higher than atmospheric.Type: GrantFiled: August 31, 1973Date of Patent: May 11, 1976Assignee: Ciba-Geigy CorporationInventor: Martin Knell
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Patent number: 3956411Abstract: Vinylidene chloride and vinylidene bromide are alkylated by reaction with alkylating agents such as selected olefins, tert-alkyl halides, and secondary or tertiary alcohols in a reaction medium comprising trifluoromethane-sulfonic acid. In specific embodiments, the reaction medium can additionally comprise water, methanol, and BF.sub.3.Type: GrantFiled: August 8, 1974Date of Patent: May 11, 1976Assignee: Phillips Petroleum CompanyInventors: John E. Mahan, John R. Norell
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Patent number: 3954893Abstract: Certain new halogenated cyclobutanes have been synthesized and found to possess utility as inhalation anesthetics. They are: 1,4-dichloro-1,2,2-trifluorocyclobutane, 1-chloro-1,2,2,4-tetrafluorocyclobutane, 1,4-dichloro-1,2,2,4-tetrafluorocyclobutane, 1-chloro-1,2,2,3,3-pentafluorocyclobutane, 1,2,2-trifluorocyclobutane, 1-chloro-2,3,3-trifluorocyclobutane, 1-chloro-2,4 4-trifluorocyclobutane, 1-bromo-1,2,2-trifluorocyclobutane, 1-bromo-2-methyl-1,4,4-trifluorocyclobutane and 1-bromo-2-chloro-1,4,4-trifluorocyclobutane.Type: GrantFiled: January 10, 1975Date of Patent: May 4, 1976Assignee: W. R. Grace & Co.Inventors: Gerald J. O'Neill, Robert S. Holdsworth, Charles W. Simons
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Patent number: 3954875Abstract: Compounds of the formula ##SPC1##WhereinR is an alkyl or an allyl group,R' is an alkyl group,R" is an alkyl group, an alkoxy group, or a trihaloalkyl group, andn is 1 or 2And compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: December 26, 1973Date of Patent: May 4, 1976Assignee: Rohm and Haas CompanyInventors: Colin Swithenbank, Wayne O. Johnson
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Patent number: 3952071Abstract: An olefin oligomer having a low viscosity and a high viscosity index can be prepared by polymerizing an olefin having 6 or more carbon atoms in the presence of a mixture of a polyhydric alcohol derivative and an aluminum halide, said derivative being obtained by replacing the hydrogen atoms of all the hydroxyl groups of the polyhydric alcohol by either acyl groups exclusively or by acyl group and alkyl groups both of said groups having 1 - 20 carbon atoms. The thus prepared olefin oligomer scarcely contains halogen, and it has a wide range of uses such as, for instance, a lubricant, a cosmetic base, etc.Type: GrantFiled: January 6, 1975Date of Patent: April 20, 1976Assignee: Lion Fat & Oil Co., Ltd.Inventors: Hiroshi Isa, Toshiyuki Ukigai, Anri Tominaga, Ryozo Taniyasu, Masuzo Nagayama
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Patent number: 3952065Abstract: A method of producing chlorobenzenes from benzene sulphonyl chlorides by a thermal chlorinating decomposition of aromatic sulphonyl chlorides of the general formula ##SPC1##WhereinX = hydrogen, halogen, alkyl group with 1-4 carbon atoms, or alkoxy group with 1-4 carbon atoms, andn = an integer of from 1 to 5,In the presence of a catalyst including a combination of active carbon and compounds selected from the group consisting of phosphorus chlorides, phosphorus bromides, and organic azo compounds capable of yielding free radicals when degrading.Type: GrantFiled: June 20, 1974Date of Patent: April 20, 1976Assignee: Vyskumny ustav agrochemickej TechnologieInventors: Bohumir Mrva, Josef Macko, Milan Kupcik, Stefan Truchlik
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Patent number: 3950445Abstract: The process of preparing benzotrifluoride which involves reacting benzotrichloride with hydrogen fluoride in a reaction zone at a pressure between 20 and 45 atm. and at a temperature between 85.degree. and 100.degree.C. The reaction is conducted in the presence of a catalyst consisting of a mixture of aluminum chloride and activated charcoal. On a stoichiometric basis, the amount of hydrogen fluoride is 1.0 to 1.1 times the amount of the benzotrichloride. The benzotrichloride, catalyst and hydrogen fluoride are present as an admixture or intermixture having a Reynolds number between 65,000 and 100,000. The reaction can be conducted in a stirring vessel equipped with a stirring mechanism.Type: GrantFiled: December 23, 1974Date of Patent: April 13, 1976Assignee: Lonza Ltd.Inventor: Kurt Ryf
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Patent number: 3950444Abstract: A process is provided for preparing ortho substituted aryl fluorides from corresponding diazonium fluorides. More particularly, the invention relates to a method for thermally decomposing diazonium fluorides substituted in the ortho position with halogen or trihalomethyl to a corresponding aryl fluoride. The method involves heating the diazonium fluoride to a temperature above its decomposition temperature and above the temperature at which the resulting product distills by contacting the same with a heat exchange medium at a temperature in the range of 100.degree.-350.degree.C.Type: GrantFiled: August 30, 1974Date of Patent: April 13, 1976Assignee: Olin CorporationInventor: Walter A. Gay
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Patent number: 3950420Abstract: Various substituted cyclohexane-1,3-diones are useful as herbicides.An exemplary species is 2-[1-(allyloxyamino)propylidene]5,5-dimethylcyclohexane-1,3-dione.Type: GrantFiled: July 22, 1974Date of Patent: April 13, 1976Assignee: Nippon Soda Company, Ltd.Inventors: Mikio Sawaki, Isao Iwataki, Yoshihiko Hirono, Hisao Ishikawa