Patents Examined by W. B. Lone
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Patent number: 3946086Abstract: A method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol of the general formula ##SPC1##Wherein R signifies an alkyl group having from 4 to 12 carbon atoms or ##SPC2##Comprising subjecting phenol to alkylation with olefines having from 4 to 12 carbon atoms or with styrene at a temperature of 50.degree.-150.degree.C in the presence of a catalyst, namely, aluminum, taken in an amount of 0.1-5 wt.% of phenol. 2,6-Dialkyl phenol or 2,6-diaralkyl phenol resulting after from the alkylation is treated with a mixture of formaldehyde and dimethylamine or with a product of their interaction having the formula ##EQU1## at a temperature of 20.degree.-100.degree.C with subsequent catalytic hydrogenolysis of N,N-dimethyl(3,5-dialkyl-4-hydroxybenzyl)/amine or N,N-dimethyl(3,5-diaralkyl-4-hydroxybenzyl/amine at a temperature of 80.degree.-200.degree.C., molar ratio of hydrogen to the product being treated of 1-5:1 and space velocity of 0.1-2 hour.sup..sup.-1.Type: GrantFiled: October 28, 1970Date of Patent: March 23, 1976Inventors: Felix Borisovich Gershanov, Alexandr Grigorievich Liakumovich, Jury Ivanovich Michurov, Boris Izrailevich Pantukh, Grigory Iosifovich Rutman, Valerian Mikhailovich Sobolev, Alexandr Afroimovich Grinberg, Yakov Abramovich Gurvich, Nina Vasilievna Zakharova, Almira Mudarisovna Nafikova
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Patent number: 3945940Abstract: Improved organic aldehyde and ketone peroxide compositions useful for initiating the polymerization of polyesters formed from the concurrent reaction of a beta dione such as 2,4-pentanedione and a different (non-beta dione) ketone or aldehyde, for example methyl ethyl ketone, with aqueous hydrogen peroxide.Type: GrantFiled: June 4, 1970Date of Patent: March 23, 1976Assignee: Argus Chemical CorporationInventor: Newton G. Leveskis
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Patent number: 3943180Abstract: Novel 2,4-bis-(trifluoromethyl)-6-nitrophenol compounds of the formula ##SPC1##In whichX is hydrogen; M; HN.sup.+R.sup.1 R.sup.2 R.sup.3 ; --COR.sup.4 ; --COOR.sup.5 ; N,N-dimethylaminocarbonyl; --SO.sub.2 R.sup.6 or --CO--NH--R.sup.7 ;M is an equivalent of an alkali metal or alkaline earth metal,R.sup.1, r.sup.2 and R.sup.3 (individually) are hydrogen, alkyl, alkoxyalkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyalkyl, phenyl or substituted phenyl,R.sup.4 and R.sup.5 individually are alkyl, substituted alkyl, alkenyl, phenyl or substituted phenyl,R.sup.6 is alkyl, substituted alkyl, phenyl, substituted phenyl or dimethylamino, andR.sup.7 is alkyl, alkenyl, cycloalkyl, phenyl or substituted phenyl; are outstandingly effective selective herbicides.Type: GrantFiled: July 17, 1974Date of Patent: March 9, 1976Assignee: Bayer AktiengesellschaftInventors: Klaus Wagner, Ludwig Eue, Robert R. Schmidt, Ernst Roos
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Patent number: 3940451Abstract: A process of recovering BHT values from the mother liquors of the crystallization of BHT obtained by alkylating p-cresol with isobutylene in the presence of a catalyst and crystallizing the BHT, comprises thermally cracking the starting mother liquor at a temperature of from 200.degree.C to 250.degree.C in the presence of an acid catalyst to reform the cresol polymers, steam distilling the cracked mixture to increase the p-cresol content and remove the diisobutylene, realkylating the steam-distilled reaction mixture with additional isobutylene, to produce a crystallizable mixture of BHT having a BHT concentration of from 80 to 85% by weight, and recovering the BHT by crystallization.The mother liquors remaining after realkylation and crystallization can be admixed with the starting mother liquors and reused in the thermal cracking step of the process.Type: GrantFiled: September 6, 1974Date of Patent: February 24, 1976Inventor: Heliodoro Monroy
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Patent number: 3939215Abstract: Aluminum is removed from sec-alkyl phenolic compositions containing aluminum in the form of a phenate by first adding aqueous alkali metal hydroxide in stoichiometric excess over said aluminum and then acidifying the mixture with a mineral acid and removing the acidic aqueous phase to leave a substantially aluminum-free sec-alkyl phenolic composition. The method is especially adapted to remove aluminum from the distillation bottoms remaining after distilling product from a sec-alkylation mixture formed by alkylating a phenol with a sec-alkyl precursor olefin using an aluminum phenate catalyst.Type: GrantFiled: May 22, 1974Date of Patent: February 17, 1976Assignee: Ethyl CorporationInventor: Lloyd E. Goddard
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Patent number: 3939211Abstract: The present invention relates to the manufacture of beta-isopropylnaphthalene hydroperoxide, an intermediate product in the manufacture of beta-naphthol.Type: GrantFiled: July 11, 1974Date of Patent: February 17, 1976Assignee: American Cyanamid CompanyInventors: Richard Harvey Spector, Richard Keith Madison
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Patent number: 3937741Abstract: Hydroquinone is made by electrolytically reducing nitrobenzene in an aqueous acid medium and thereafter maintaining the reaction medium containing the amino product, at a temperature of 200.degree. to 300.degree.C. for a sufficient time to hydrolyze the amino product to hydroquinone, and extracting the hydroquinone from the aqueous reaction medium.Type: GrantFiled: January 20, 1975Date of Patent: February 10, 1976Assignee: Koppers Company, Inc.Inventor: Nicholas P. Greco
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Patent number: 3937740Abstract: A process for producing 2,3,6-trimethylphenol by reacting a m-cresol with methanol in the gas phase in the presence of a catalyst containing ceric oxide, zinc oxide, and an oxide of a metal selected from the group consisting of an alkali metal, barium, calcium or strontium.Type: GrantFiled: March 28, 1974Date of Patent: February 10, 1976Assignee: Hoffmann-La Roche Inc.Inventors: Wolf Brenner, Herbert Lindlar, Rudolf Hinderling
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Patent number: 3936506Abstract: Unsymmetrical halogen-substituted diacyl peroxides have been prepared either by rapidly adding an .alpha.-halogen-substituted aliphatic acyl halide and a hydrocarbon solvent to an aqueous solution of an alkali metal peroxide followed by portion-wise addition of an acyl halide or by rapidly adding an acyl halide and a hydrocarbon solvent to an aqueous solution of an alkali metal peroxide followed by portion-wise addition of an .alpha.-halogen-substituted aliphatic acyl halide. The formation of diacyl peroxides and symmetrical halogenated diacyl peroxides as by-products is minimized by either technique.Type: GrantFiled: February 26, 1973Date of Patent: February 3, 1976Assignee: Union Carbide CorporationInventor: Robert V. Berthold
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Patent number: 3935282Abstract: .alpha.-Naphthol is prepared by dehydrogenating .alpha.-Tetralone in the presence of a catalyst comprising (1) platinum or a platinum compound, (2) an alkali metal salt, and (3) a manganese compound and/or a chromium compound supported on a gamma-type alumina carrier. By using such catalyst, the conversion of .alpha.-Tetralone is markedly increased, and the catalyst life is very much prolonged.Type: GrantFiled: May 6, 1974Date of Patent: January 27, 1976Assignee: Sumitomo Chemical Company, Ltd.Inventors: Ken-ichi Kudo, Tadayuki Ohmae, Akihiko Uno
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Patent number: 3935283Abstract: Hydroquinone is made by contacting nitrobenzene in an aqueous acid medium with hydrogen at elevated temperatures and pressures in the presence of an acid resistant reducing catalyst until hydrogen absorption ceases, removing any unreduced nitrobenzene from the reaction medium, removing the catalyst from the reaction medium, thereafter maintaining the reaction medium containing the hydrogen reduction product at a temperature of 200.degree. to 300.degree.C. for a sufficient time to hydrolyze the reduction product to hydroquinone, and extracting the hydroquinone from the aqueous reaction medium.Type: GrantFiled: January 17, 1975Date of Patent: January 27, 1976Assignee: Koppers Company, Inc.Inventor: Nicholas P. Greco
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Patent number: 3935278Abstract: Diperoxides, useful as free radical type polymerization initiators, for example, are preparable from an organic hydroperoxide such as t-butyl hydroperoxide, and a ketone using catalyst comprising molybdenum or vanadium.Type: GrantFiled: March 4, 1970Date of Patent: January 27, 1976Assignee: Atlantic Richfield CompanyInventors: Rudolph Rosenthal, Harold A. Sorgenti
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Patent number: 3933925Abstract: Methyl resorcinols are produced by the hydrolysis of toluene diamines in an aqueous excess of ammonium bisulfate. The reactants are contacted at an elevated temperature for a period of time sufficient to hydrolyze the toluene diamines to methyl resorcinols. The methyl resorcinols so produced are separated from the reaction mixture. The ammonium sulfate is regenerated to ammonium bisulfate by removing the water and thermally decomposing the by-product ammonium sulfate at an elevated temperature.Type: GrantFiled: January 17, 1975Date of Patent: January 20, 1976Assignee: Koppers Company, Inc.Inventor: Nicholas P. Greco
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Patent number: 3933927Abstract: Phenols having an unsubstituted ortho position are transalkylated in the ortho position by mixing them with an ortho-alpha-branched alkylphenol (e.g., 2,6-di-sec-butylphenol) and an aluminum phenoxide catalyst and heating the mixture to 100.degree.-350.degree.C., preferably in a closed system and in the presence of olefin corresponding in structure to the ortho-alpha-branched alkyl group.Type: GrantFiled: April 13, 1973Date of Patent: January 20, 1976Assignee: Ethyl CorporationInventor: Lloyd E. Goddard
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Patent number: 3933928Abstract: 2,6-DI-TERT.-BUTYL-4-CUMYL PHENOL IS PRODUCED BY REACTING P-CUMYL PHENOL WITH ISOBUTYLENE, AT A REACTION TEMPERATURE OF FROM 40.degree. TO 120.degree.C. in the presence of from 0.01 to 20% by weight of p-toluene sulfonic acid based on the weight of the p-cumyl phenol. Isobutylene is charged into the reaction system at a high rate and is always present in the reaction system during the reaction. A substantially 100% conversion of p-cumyl phenol is attained and the weight ratio of 2,6-di-tert.-butyl-4-cumyl phenol/2-tert.-butyl-4-cumyl phenol in the reaction product is greater than 10, while splitting off of the cumyl group at the para position is suppressed.Type: GrantFiled: August 21, 1974Date of Patent: January 20, 1976Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Kunio Hanauye, Tsutomu Takase, Mitsuhiro Iwasa, Mizuo Ito
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Patent number: 3933921Abstract: In a process for the production of hydroperoxides by the oxidation of an aromatic hydrocarbon having at least one tertiary carbon atom with oxygen or an oxygen containing gas in the presence of an aqueous alkaline solution, an improvement is made in that the oxidation is effected in an emulsion phase which is caused by powerfully mixing all or a part of the materials to be brought into the oxidation reaction only by the aid of the hydroperoxides formed in the reaction, whereby enhancing the reaction rate with safety.Type: GrantFiled: June 18, 1973Date of Patent: January 20, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Hideaki Suda, Iwao Dohgane, Takashi Chinuki, Kenji Tanimoto, Hirokazu Hosaka, Yukimichi Nakao, Yuji Ueda, Seiya Imada, Hideki Yanagihara, Kunihiko Tanaka
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Patent number: 3933926Abstract: A process for the preparation of nitrophenols by adding over a period of time a suspension containing from about 4 to about 20 per cent weight/volume of nitrosated phenol to a nitric acid solution containing between 45 and 100 per cent by weight of nitric acid, said solution being maintained at a temperature in the range from about 45.degree. to 100.degree.C.Type: GrantFiled: May 30, 1973Date of Patent: January 20, 1976Inventors: David Anthony Salter, Robert John James Simkins
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Patent number: 3933929Abstract: In a purification process for p-nitrophenol obtained by nitration of phenol, separation of crude nitrophenols, steam distillation to remove o-nitrophenol, and cooling the broth obtained when it contains more than 0.5% sodium bisulphite and is at pH 5.4 to 6.4 to deposit crystals of p-nitrophenol, an improvement consists in stirring the crystals with water at 55.degree.-85.degree.C to give a mixture containing 10-40% excess of p-nitrophenol over the solubility at that temperature, separating the upper layer of p-nitrophenol in water obtained, cooling it to 40.degree.-50.degree.C and separating the layer of water in p-nitrophenol, cooling the latter to below 30.degree.C and collecting the crystals deposited.Type: GrantFiled: May 14, 1973Date of Patent: January 20, 1976Assignee: Rhone-Poulenc S.A.Inventor: Gilbert Colovray
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Patent number: 3932538Abstract: A process for producing pyrogallol or 5-substituted pyrogallol having the formula: ##SPC1##Wherein R is selected from the group consisting of alkyl, cycloalkyl, aryl, and aralkyl, or a mixture thereof which comprises heating an aqueous solution of 4-substituted-2,6-diaminophenol or 4-substituted-2,6-diamino 1-alkoxybenzene having the formula: ##SPC2##Wherein R is as defined above and A is selected from the group consisting of hydrogen and alkyl, under acid conditions.Type: GrantFiled: September 30, 1974Date of Patent: January 13, 1976Assignee: Mitsubishi Chemical Industries, LimitedInventors: Heitaro Obara, Junichi Onodera, Akira Matukuma, Kenji Yoshida
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Patent number: 3932535Abstract: Process for the preparation of especially pure 2,2-bis-(4-hydroxy-3-chlorophenyl)-propane (dichlordiane, DCD) by the chlorination of 2,2-bis-(4-hydroxyphenyl)-propane in the presence of solvents that are substantially indifferent to chlorine by prior-art methods; then, for purification, the chlorinated bis-phenol is dissolved in halogenated hydrocarbons and/or halogenated hydrocarbon in which are liquid at 20.degree.C which they are readily soluble in the absence of an aqueous phase but in which they are at most only slightly soluble after the addition of water thereto; and the 2,2-bis-(4-hydroxy-3-chlorophenyl)-propane, is thereby precipitated from this aqueous solution.Type: GrantFiled: February 15, 1974Date of Patent: January 13, 1976Assignee: Dynamit Nobel AktiengesellschaftInventors: Gunter Zoche, Hermann Richtzenhain, Roshdy Ismail