Patents Examined by M. C. Eakin
  • Patent number: 4298761
    Abstract: A process for the preparation of 4-nitrothioanisole comprising successively in a single vessel and without intermediate isolation reacting 4-nitrochlorobenzene with Na.sub.2 S.sub.2, then with an alkaline Na.sub.2 S solution and with a methylating agent. Advantageously the reactions are effected in methanol or aqueous methanol, the reactions with Na.sub.2 S.sub.2 and Na.sub.2 S are carried out at a temperature between about 50.degree. to 70.degree. C., the Na.sub.2 S.sub.2 is formed in situ in about 20% excess from Na.sub.2 S and sulphur, the Na.sub.2 S solution is rendered alkaline with sodium methylate or sodium hydroxide, and methylation is effected with methyl chloride at about 27.degree. to 35.degree. C. The product is produced in such high yield and purity that it can be employed directly for chlorination, without extensive purification, to produce insecticide intermediates.
    Type: Grant
    Filed: January 9, 1980
    Date of Patent: November 3, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Hagemann, Erich Klauke, Gerd-Michael Petruck
  • Patent number: 4297282
    Abstract: This invention relates to a process for the optical resolution of DL-.alpha.-methyl-.beta.-acylthiopropionic acids of the formula [I], ##STR1## wherein R is a lower alkyl group having 1-4 carbon atoms, phenyl or substituted phenyl bearing methyl or chloro radical; a method for the racemization of an optically active .alpha.-methyl-.beta.-acylthiopropionic acid of the formula [Ia], ##STR2## wherein R is as defined above; and a process for the synthesis of captopril of the formula [II], ##STR3## using the D-acid [Ia] as an intermediate. The optically active .alpha.-methyl-.beta.-acylthiopropionic acids are useful as intermediates for the production of medicines, for example, captopril or its congeners.
    Type: Grant
    Filed: November 2, 1979
    Date of Patent: October 27, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naohito Ohashi, Shoji Nagata, Junki Katsube
  • Patent number: 4293503
    Abstract: Disclosed is an improved method of forming polyol (allyl carbonate) monomers. In the disclosed method, the organic by-products as diallyl carbonate and unreacted reagents as allyl alcohol are separated from the brine and wash water derived aqueous phase and returned to the allyl carbonate synthesis reaction. The aqueous phase is further separated to recover allyl alcohol therefrom, which is returned to the allyl carbonate synthesis reactor as an azeotrope.
    Type: Grant
    Filed: January 10, 1980
    Date of Patent: October 6, 1981
    Assignee: PPG Industries, Inc.
    Inventor: Elgin E. Young
  • Patent number: 4292071
    Abstract: A novel class of compounds which are useful as plant growth regulators is disclosed, having the general structural formula: ##STR1## In which R is cyano C.sub.1 to C.sub.5 alkyl, alkenyl or alkynyl to which may be attached phenyl, halophenyl, methylphenyl, pyridyl, benzoyl, trimethylacetyl, phenoxy, halophenoxy, halobenzoyl, N-phenylcarbamyl, N-alkylcarbamyl, N-trifluoromethylthiadiazolylcarbamyl, carboxy, carbalkoxy or halo substituents,R.sup.1 is H, acetyl C.sub.1 to C.sub.3 alkyl, alkenyl or alkynyl to which may be attached phenyl, halophenyl, carbethoxy, vinyloxy or phenoxy groups, or R and R.sup.1 together may be C.sub.2 to C.sub.4 alkylene,Ar is phenyl or benzoyl,R.sup.2 is C.sub.1 to C.sub.
    Type: Grant
    Filed: April 10, 1980
    Date of Patent: September 29, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Joel L. Kirkpatrick, Natu R. Patel, Jerry L. Rutter
  • Patent number: 4292070
    Abstract: N-substituted-3,4,5,6-tetrahydrophthalimides in which the N-substituted group is a phenyl group having a substituted-oxy group at 3-position and a chlorine or bromine atom at 4-position and chlorine or hydrogen atom at 2-position have excellent herbicidal effect and are used as selective herbicides in a plant culturing.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: September 29, 1981
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Osamu Wakabayashi, Kuni Matsuya, Hiroki Ohta, Tetsuo Jikihara, Seiichi Suzuki
  • Patent number: 4289756
    Abstract: Loaded cells suspended in a physiological solution are prepared in a process in which their volume is expanded by osmotic pressure. Cells so prepared suspended in a physiological solution, when injected into the bloodstream of a living body are preferentially accumulated in the spleen and liver of the body, which treats them as foreign bodies, even though the original cells may have been cells of an animal of the same species. Similarly by storing the loaded cells in a solution containing substances such as glutadialdehyde, formaldehyde that react with the protein phase of membranes or which, like difluoro dinitrobenzene, react with the lipid layer thereof, the loaded cells can also be caused to be broken down by the spleen and/or liver. Premature release of the contents of the loaded cells is prevented and timely release of such contents is assured by incorporating other materials into the loaded cells during the preparation process in accordance with the related application of the same inventors, Ser. No.
    Type: Grant
    Filed: December 14, 1977
    Date of Patent: September 15, 1981
    Assignee: Kernforschungsanlage Julich GmbH
    Inventors: Ulrich Zimmermann, Gunter Pilwat, Karin Bock, Hermann J. Buers
  • Patent number: 4289784
    Abstract: Novel substituted pyromellitic diimides are disclosed wherein the compounds are assymetrically substituted with a variety of substituent groups. Processes for the preparation of such compounds are also disclosed. The novel assymetrically substituted pyromellitic diimides are useful for administration to ruminant animals to increase feed efficiency, shift volatile fatty acid production in the ruminants from acetate with an increase in the more energetically efficient propionate and butyrate and to suppress methane formation in the rumen. Composition and methods of treatment utilizing said compounds as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: April 22, 1980
    Date of Patent: September 15, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Richard J. Bochis, Michael H. Fisher, Bruce O. Linn
  • Patent number: 4289527
    Abstract: A novel class of compounds which are useful as plant growth regulators is disclosed, having the general structural formula: ##STR1## R.sup.1 is C.sub.1 to C.sub.4 alkyl, nitro or halo and n is zero or an integer from 1 to 4R.sup.2 is hydrogen, C.sub.1 to C.sub.4 alkyl, allyl or benzyl; n' is zero, 1 or 2 and Ar is naphthyl, phenoxybenzyl, phenyl or phenyl bearing thereon from one to three of the substituents: cyano, phenoxy, nitro, bromo, chloro, fluoro and C.sub.1 to C.sub.4 alkyl, alkenyl, alkoxy, alkylthio, carbalkoxy or alkyl-substituted amino.
    Type: Grant
    Filed: August 4, 1980
    Date of Patent: September 15, 1981
    Assignee: Gulf Oil Corporation
    Inventor: Loren W. Hedrich
  • Patent number: 4288243
    Abstract: This invention relates to herbicidally active diphenyl ether compounds, herbicidal compositions thereof and the control of weeds therewith, said compounds represented by the formula ##STR1## wherein A is: ##STR2## wherein: X is hydrogen or halogen;Y is hydrogen, halogen, cyano, trifluoromethyl, or alkyl containing up to 4 carbon atoms;Z is nitro, halogen, or cyano; andR and R.sup.1 are the same or different and represent hydrogen, halogen, or alkyl containing up to 10 carbon atoms, or R and R.sup.1 may join together to form a benzene ring.
    Type: Grant
    Filed: July 7, 1980
    Date of Patent: September 8, 1981
    Assignee: PPG Industries, Inc.
    Inventor: William S. Grove
  • Patent number: 4288628
    Abstract: A process for the production of a mono-halothiophenol, e.g. para-chlorothiophenol, and thiophenol. The process comprises reacting a reactant mixture of benzene and dihalobenzene, e.g. para-dichlorobenzene, with hydrogen sulfide in the presence of an absorptive catalyst, such as activated carbon, calcined petroleum coke, etc.
    Type: Grant
    Filed: March 8, 1979
    Date of Patent: September 8, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Kyung S. Shim
  • Patent number: 4288627
    Abstract: A thiol is oxidized to a corresponding disulfide employing a supported cobalt molybdate catalyst in combination with a liquid tertiary amine. 2-propanethiol is converted to diisopropyl disulfide with conversions of the order of 94% and selectivities of the order of 98%.
    Type: Grant
    Filed: February 12, 1980
    Date of Patent: September 8, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Donald H. Kubicek
  • Patent number: 4288449
    Abstract: Compounds of the formula 1 ##STR1## where R.sup.1 is a saturated, unsubstituted or substituted aliphatic radical of 1 to 8 carbon atoms, an unsaturated alkyl radical of 2 to 8 carbon atoms, a cycloalkyl radical of 3 to 7 carbon atoms in the ring or an alkyl radical of 1 to 4 carbon atoms which is substituted by phenyl or by a 5- or 6-membered aromatic heterocyclic ring containing an N, O or S atom, the phenyl ring or the heterocyclic ring itself being unsubstituted, monosubstituted or polysubstituted, andR.sup.2 is hydrogen orR.sup.1 and R.sup.2 together with the nitrogen are a 4-membered to 6-membered cycloaliphatic saturated heterocyclic ring,R.sup.3 is hydrogen or alkyl of 1 to 5 carbon atoms,R.sup.4 and R.sup.
    Type: Grant
    Filed: May 28, 1980
    Date of Patent: September 8, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Jens-Uwe Bliesener, Karl-Heinz Geiss, Dieter Lenke, Claus D. Mueller
  • Patent number: 4287366
    Abstract: A process for preparing bisphenol sulfone derivatives represented by the general formula (I) ##STR1## where R stands for hydrogen, a halogen, an alkyl radical, a cycloalkyl radical, an aryl radical, an aralkyl radical, hydroxyl group, an alkoxy radical, allyloxy group, carboxyl group, or a carboalkoxy radical, m is an integer of from 1 to 3, and when m is 2 or more, R may be identical to or different from each other, and adjacent Rs may be combined to form a ring, by oxidizing with hydrogen peroxide a compound represented by the general formula (II) ##STR2## where R and m have the same meanings as defined for the formula (I), and n is zero or 1, in the presence of an alkali in an amount more than the equimolar amount thereof relative to said compound in water and/or an organic solvent which do not form any organic peracids under reaction conditions.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: September 1, 1981
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Akihiro Yamaguchi, Keizaburo Yamaguchi, Hisamichi Murakami, Tadashi Kobayashi
  • Patent number: 4285882
    Abstract: When the reaction of aldehydes with alkali metal trihaloacetates is carried out in the presence of a highly polar aprotic solvent (DMF, DMSO), novel organic alkali metal carbonates, which are precursors of pyrethroid insecticides, are formed in high yields and at a high rate. Novel sulfonates and dihalophosphites, derived from these carbonates have also been claimed.
    Type: Grant
    Filed: March 25, 1980
    Date of Patent: August 25, 1981
    Assignee: Shell Oil Company
    Inventors: Petrus A. Kramer, Pieter A. Verbrugge
  • Patent number: 4284426
    Abstract: 2-chloro-4,5-disubstituted-thiazoles have been found to be effective in reducing herbicidal injury to sorghum plants due to the application thereto of acetanilide and thiocarbamate herbicides.
    Type: Grant
    Filed: October 1, 1979
    Date of Patent: August 18, 1981
    Assignee: Monsanto Company
    Inventors: Robert K. Howe, Len F. Lee
  • Patent number: 4284624
    Abstract: This invention is directed to compounds of the formula ##STR1## wherein A and A.sub.1 are amino acid residues, X is and .alpha.-imino acid residue, and R.sub.1 is hydrogen, lower alkyl, or halo substituted lower alkyl. These compounds are useful as hypotensive agents.
    Type: Grant
    Filed: May 2, 1980
    Date of Patent: August 18, 1981
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Sesha I. Natarajan, Miguel A. Ondetti, Shih-jung Lan, Keith K. Wong
  • Patent number: 4284817
    Abstract: Thiophenols are produced by reacting the corresponding benzene compound with hydrogen sulfide in contact with an absorptive catalyst, such as activated carbon, calcined petroleum coke, etc. Temperatures in the range of from about 500.degree. to 900.degree. C. are employed.
    Type: Grant
    Filed: June 2, 1977
    Date of Patent: August 18, 1981
    Assignee: Stauffer Chemical Company
    Inventors: Kyung S. Shim, Adam E. Skrzec
  • Patent number: 4284561
    Abstract: Hydroxamic acid derivatives of certain mercaptoacyl amino acids inhibit the conversion of angiotensin I to angiotensin II in mammals and are useful for the treatment of hypertension.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: August 18, 1981
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Edward W. Petrillo, Jr., Miguel A. Ondetti
  • Patent number: 4283335
    Abstract: Disclosed is a method for improving the yield of dialkyl dithiophosphoric acid esters produced by the Lewis acid catalyzed reaction of an O,O-dialkyl dithiophosphoric acid and an organic chloride. More specifically, the method concerns the improvement wherein the reaction is carried out in the presence of from 0.1 to 1.5 moles, per mole of organic chloride, of an anhydride of a fatty acid containing 2 to 5 carbon atoms.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: August 11, 1981
    Assignee: Boots Hercules Agrochemicals Co.
    Inventor: James Minn
  • Patent number: RE30752
    Abstract: Novel carbonic acid esters are disclosed which are useful in a process for introducing esterified carboxy-type protective groups on amino and/or imino groups in amino and/or imino group-containing compounds for the temporary protection of said amino and/or imino groups. Additionally, processes for preparing said esters are also disclosed. .Iadd.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: September 29, 1981
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masumi Itoh, Takashi Kamiya, Daijiro Hagiwara