Patents Examined by Margaret Argo
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Patent number: 5189222Abstract: Process for the manufacture and recovery of alkali-metal tetraorganylborates. A mixed solvent and liquid/liquid contactor configuration is used in the system which aids in the recovery of the product.Type: GrantFiled: January 29, 1990Date of Patent: February 23, 1993Assignee: Optima Chemicals, Inc.Inventors: Eugene C. Ashby, Laurence L. Earnhart, Daniel W. Tedder, Jagvir Singh
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Patent number: 5171885Abstract: The pure isomers L-buthionine-S-sulfoximine and L-buthionine-R-sulfoximine are provided. The L-S-isomer has utility, for example, in causing the depletion of glutathione, a major protectant molecule in tumors and certain parasites. The L-R-isomer has utility as a compound decreasing further uptake and thus effect of the L-S-isomer and for causing glutathione depletion specific to the kidney. The isolation of pure isomers from L-buthionine-SR-sulfoximine enables treatment at lower dosages without cross effects.The pure L-buthionine-S-sulfoximine isomer is obtained from L-buthionine-SR-sulfoximine by recrystallization preferably by forming a solution of L-buthionine-SR-sulfoximine in water at a concentration of 0.Type: GrantFiled: June 19, 1991Date of Patent: December 15, 1992Assignee: Cornell Research Foundation, Inc.Inventor: Owen W. Griffith
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Patent number: 5166425Abstract: A compound of the formula: ##STR1## wherein R and R' each is hydrogen or a protecting group, or acid addition salts thereof, useful as a selective insecticide.Type: GrantFiled: May 28, 1991Date of Patent: November 24, 1992Assignee: Shionogi & Co., Ltd.Inventors: Tadahiko Tsushima, Shoichi Ishihara
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Patent number: 5152826Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: October 16, 1991Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventor: Christopher G. Knudsen
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Patent number: 5149878Abstract: Various 1,4-disubstituted-2,3,5,6-tetrahydroxy-1,4-diphosphorinanes, their oxides and sulfides, methods for the production thereof, flame-retarded compositions of matter containing them and froth flotation processes therewith, are disclosed.Type: GrantFiled: July 2, 1990Date of Patent: September 22, 1992Inventors: Allan J. Robertson, James B. Gallivan
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Patent number: 5144080Abstract: A process is provided for preparing isoprenoid cyclopropane 1,1-dicarboxylates and derivatives thereof including the corresponding monocarboxylate, monocarboxylic acid and alcohol derivatives thereof, all of which are useful in preparing squalene synthetase inhibitors which inhibit cholesterol biosynthesis, and also useful in preparing pyrethrin insecticides.Type: GrantFiled: August 30, 1991Date of Patent: September 1, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Scott A. Biller, Cornelia Forster
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Patent number: 5144067Abstract: Disclosed is a process for the coproduction of (1) an alkyl iodide and (2) an .alpha.-iodocarboxylic acid, a mono-.alpha.-iodocarboxylic anhydride or a mixture thereof which comprises contacting a mixture of an iodine compound and a carboxylic anhydride with a peroxide at an elevated temperature.Type: GrantFiled: September 29, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier, Brent A. Tennant
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Patent number: 5144070Abstract: Disclosed is a process for the preparation of .alpha.-iodocarbonyl compounds such as .alpha.-iodocarboxylic acid anhydrides and .alpha.-iodoketones by the reaction of a carboxylic anhydride with molecular iodine. Hydrolysis of the .alpha.-iodocarboxylic acid anhydrides gives the corresponding .alpha.-iodocarboxylic acids.Type: GrantFiled: August 30, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier
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Patent number: 5144083Abstract: A process for producing a p-hydroxyneophyl m-phenoxybenzyl ether represented by the general formula (II) ##STR1## (X.sub.1 and X.sub.2 are independently a hydrogen atom or a halogen atom) by subjecting a corresponding p-alkoxyneophyl m-phenoxybenzyl ether represented by the general formula (I) ##STR2## (R represents a lower alkyl group, and X.sub.1 and X.sub.2 have the same definitions as above) to ether cleavage, in which process the ether cleavage reaction is effected in an aprotic polar solvent, using a lower alkoxide of an alkali metal or an alkaline earth metal or using a metal hydroxide in the presence of a lower alcohol.Type: GrantFiled: October 2, 1990Date of Patent: September 1, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
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Patent number: 5144079Abstract: This invention relates to a process for the preparation of 2-nitro-4-(C.sub.1 -C.sub.4 alkylsulfonyl) toluene or 2-nitro-4-(C.sub.1 -C.sub.4 alkylsulfonyl) ethylbenzene by the alkylsulfonylation of 2-nitrotoluene or 2-nitro ethylbenzene.Type: GrantFiled: February 14, 1991Date of Patent: September 1, 1992Assignee: Imperial Chemical Industries PlcInventor: Peter K. Wehrenberg
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Patent number: 5136106Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zirconium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.Type: GrantFiled: March 14, 1991Date of Patent: August 4, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5114977Abstract: There are disclosed 1-[4-(halophenoxy)phenoxy]-4-pentines of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other chloro or fluoro and one of R.sub.1 and R.sub.2 is also hydrogen, a process for their preparation and intermediates for their preparation, the use of these compounds in pest control, and pesticidal compositions which contains a compound of formula I as active component. The preferred field of use is ovicidal control of pests.Type: GrantFiled: August 2, 1991Date of Patent: May 19, 1992Assignee: Ciba-Geigy CorporationInventors: Friedrich Karrer, Alfred Rindlisbacher
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Process for phenol alkylthiolation and its application to the synthesis of 4-acyl-2-alkylthiophenols
Patent number: 5113019Abstract: The invention relates to the preparation of alkylthiophenols by reaction of a dialkyl disulphide with a phenol.In the process according to the invention, the reaction is carried out in the presence of aluminum chloride or of ferric chloride in a solvent of the alkylbenzene type or, soley in the case of methylthiolation, in an excess of dimethyl disulphide.This process makes it possible, in particular to obtain, with a selectivity and in a yield which are excellent, 2-alkylthiophenols which may then be converted into 4-acyl-2-alkylthiophenols by means of a reaction at a temperature ranging from 40.degree. to 100.degree. C. with a complex BF.sub.3 :2RCOOH where R denotes an alkyl or propenyl radical, in a proportion of 10 to 15 moles of complex per mole of 2-alkylthiophenol.Type: GrantFiled: November 5, 1990Date of Patent: May 12, 1992Assignee: Societe Nationale Elf Aquitaine (Production)Inventors: Catherine Vottero, Yves Labat, Jean-Marie Poirier -
Patent number: 5107031Abstract: The invention is a process to recover 4-phenoxybiphenyl from a phenoxybiphenyl mixture which includes at least 30% by weight of 4-phenoxybiphenyl, the balance being 2-phenoxybiphenyl, 3-phenoxybiphenyl and a minor amount of other compounds. The process involves recrystallizing 4-phenoxybiphenyl as a solid in a single recrystallization step from a solution formed from the mixture and an alcohol solvent. The recovered solid has a 4-phenoxybiphenyl content of at least about 85% by weight of recovered solid and a yield of at least 40% based on the amount of 4-phenoxybiphenyl in the mixture.Type: GrantFiled: December 19, 1989Date of Patent: April 21, 1992Assignee: The Dow Chemical CompanyInventors: Gary R. Buske, Jeffrey M. Marra, Guo-shuh J. Lee
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Patent number: 5107038Abstract: A process for the preparation of 4-tert-butyl-cyclohexanol, comprising the hydrogenation of 4-tert-butyl-phenol or of 4-tert-butyl-cyclohexanone in the presence of a catalytic system composed of rhodium on a Al.sub.2 O.sub.3, SiO.sub.2, TiO.sub.2, SiO.sub.2.Al.sub.2 O.sub.3 or charcoal support, in combination with HBF.sub.4 or BF.sub.3.[Y].sub.n wherein Y designates a R.sub.2 O group, R being a C.sub.1 to C.sub.6 lower alkyl radical, or a CH.sub.3 CO.sub.2 H, H.sub.3 PO.sub.4 or H.sub.2 O group and index n is equal to zero, 1 or 2.Type: GrantFiled: October 22, 1990Date of Patent: April 21, 1992Assignee: Firmenich SAInventor: Robert M. Weinstein
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Patent number: 5105021Abstract: A higher yield of the difluorohalomethoxybenzene produced by the reaction of a metal phenolate with dibromodifluoromethane or bromochlorodifluoromethane can be obtained by conducting the addition of a metal alcoholate or a metal hydride as a reaction initiator to a solution or a suspension of an aprotic polar solvent containing the metal phenolate and dibromodifluoromethane or bromochlorodifluoromethane.Type: GrantFiled: April 12, 1990Date of Patent: April 14, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
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Patent number: 5105016Abstract: Bis(cyclohexylphenol) compounds of the formula ##STR1## wherein R is an alkyl having 1 to 6 carbon atoms, Y is --S--, --SO-- or --SO.sub.2 -- with the proviso that when R is methyl in the ortho position to the hydroxy, Y is --SO-- or --SO.sub.2 --and their use. The above-mentioned compounds are useful as antioxidants and biocides for industrial use.Type: GrantFiled: November 20, 1990Date of Patent: April 14, 1992Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Kazumi Saeki, Akira Shimada
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Patent number: 5103046Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared bya) reacting, an inert organic solvent, a salt of sulfamic acid, which is at least partially soluble therein, with at least approximately the equimolar amount of an acetoacetylating agent, in the presence of an amine or phosphine catalyst, and by cyclizing the acetoacetamide-N-sulfonate which is formed in this reaction, or the free sulfonic acid,b) by the action of at least approximately the equimolar amount of SO.sub.3, where appropriate in an inert inorganic or organic solvent, to give 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide, which is produced in the form of the acid in this reaction;it is possible, if desired, to obtain from the acid formc) the appropriate salts by neutralization with bases.The non-toxic salts-- in particular the potassium salt-- are valuable synthetic sweeteners.Type: GrantFiled: January 29, 1991Date of Patent: April 7, 1992Assignee: Hoechst AktiengesellschaftInventors: Karl Clauss, Adolf Linkies, Dieter Reuschling
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Patent number: 5103050Abstract: A continuous process for preparing perfluoroalkenyl sulfonyl fluorides (I)R.sub.f --CF.dbd.CF--SO.sub.2 F (I)wherein: R.sub.f is selected from the group consisting of F and a perfluoroalkyl radical of from 1 to 9 carbon atoms is disclosed, in which as the starting compound a sultone (II) ##STR1## is used. The starting compound is placed into contact with a reactant selected from the group consisting of oxides and carbonates of an element of the Groups IA, IIA and IIB, and of the oxides of an element of the Groups IIIA and IVA of the Periodic Table of the Elements, and their mixtures, at a temperature comprised within the range of from 150.degree. to 450.degree. C., and the compound (I) is recovered from the reaction effluent. and the compound (I) is recovered from the reaction effluent.Type: GrantFiled: April 26, 1990Date of Patent: April 7, 1992Assignee: Ausimont S.r.l.Inventors: Walter Navarrini, Silvana Modena
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Patent number: 5103063Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol. This invention also concerns novel intermediates R'.sub.2 B(2'-isoprenyl) wherein R' is isopinocampheyl, 2-isocaranyl and 4-isocaranyl.Type: GrantFiled: August 3, 1990Date of Patent: April 7, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown