Patents Examined by Dolph H. Torrence
  • Patent number: 4519953
    Abstract: A process for preparing stilbenedicarbonitrile by dimerizing o- or p-cyanobenzyl chloride in a polar aprotic solvent in the presence of an excess of alkali metal hydroxide powder. Stilbenedicarbonitriles are precursors for the preparation of fluorescent brighteners of the bisbenzoxazolylstilbene class.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: May 28, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Lorenz Heiss
  • Patent number: 4517130
    Abstract: An improved process for preparing substituted amino acids and lower alkyl esters thereof, and intermediates therefor, comprising reacting a substituted aniline, HCN and an aldehyde to form a nitrile, converting the nitrile to an imidate salt with a strong acid and an alcohol, hydrolyzing in situ the imidate salt to the ester with addition of water, and optionally converting the ester to the salt or free acid. The acids are useful intermediates in the synthesis of pesticides.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: May 14, 1985
    Assignee: Zoecon Corporation
    Inventor: Ted A. Baer
  • Patent number: 4517132
    Abstract: This invention relates to the discovery that high yields of excellent quality cyanohydrins can be prepared by reacting certain carbonyl compounds in a solution of metallic cyanide and hydrochloric acid.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: May 14, 1985
    Assignee: Union Carbide Corporation
    Inventor: John K. Chan
  • Patent number: 4517131
    Abstract: Hydroxyaromatic compounds are amido-alkylated or cyano-alkylated to form the corresponding compounds by:(a) heating said compounds with an alkylating agent in the presence of water and a catalyst, e.g., benzyltrimethylammonium chloride;(b) adding an alkaline agent, e.g., NaOH, to the heated mixture of (a); and(c) continuing to heat the resulting mixture until the corresponding amido- or cyano-alkylated compound is formed.
    Type: Grant
    Filed: September 11, 1981
    Date of Patent: May 14, 1985
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4517129
    Abstract: Cyanotetrachlorobenzenes, especially ortho- and para- dicyanotetrachlorobenzenes, are prepared by reacting in a liquid medium at 20.degree.-100.degree. C. a corresponding nitrotetrachlorobenzene with, in solution, an inorganic cyanide. Preferably the liquid medium is a two-phase water/water-immiscible organic solvent system, e.g. water/chloroform, a phase transfer catalyst is present and the inorganic cyanide is an alkali metal or alkaline earth metal cyanide.The compounds are useful chemical intermediates in the synthesis of, for instance, pesticidal compounds.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: May 14, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: David J. Milner
  • Patent number: 4515731
    Abstract: Catalytic asymmetric hydrogenation of the Z geometric isomer of a compound of the formula ##STR1## wherein at least one of R and R.sup.1 represents hydrogen and the other represents hydrogen, lower alkyl or aryl; R.sup.2 represents ##STR2## wherein R.sup.4 and R.sup.5 each independently represent hydrogen, lower alkyl or aryl, R.sup.6 represents hydrogen, lower alkyl, aryl or an alkali metal; and R.sup.3 represents ##STR3## wherein R.sup.7 and R.sup.8 each independently represent lower alkyl or aryl; provided that, when R.sup.3 is ##STR4## R.sup.2 is --CN, in the presence of a homogeneous, coordination complex catalyst comprising rhodium, iridium or ruthenium in combination with an optically active bis phosphine ligand provides an outstanding level of optical purity.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: May 7, 1985
    Assignee: Monsanto Company
    Inventors: Gerald L. Bachman, Billy D. Vineyard
  • Patent number: 4515730
    Abstract: A process for determining the pH value in the interior of a cell is described. This is accomplished by measurement of the emission of a fluorescent substance which is absorbed by the cell through incubation in a solution. The solution contains a compound of the said fluorescent substance; the fluorescent substance is separated from this compound in the cell by an enzyme present in the cell. The fluorescent substance selected is one such that the frequency of the emission maximum is dependent on the pH value. The compound of this fluorescent substance which is selected is one which is membrane penetrating. Measurement of the fluorescence is based on the principle of measurement of the frequency at which the emission maximum occurs. A fluorescent substance suitable for this purpose is 2,3-dicyano-1,4-hydroquinone. A suitable membrane penetrating compound is 1,4-diacetoxy-2,3-dicyanobenzene or 1,4-dibutyryloxy-2,3-dicyanobenzene or 1,4-di(-tert-butyloxycarbonyl-1-alanyloxy)-2,3-dicyanobenzene.
    Type: Grant
    Filed: July 2, 1982
    Date of Patent: May 7, 1985
    Inventors: Gunter Valet, Gerhard Ruhenstroth-Bauer, Erich Wunsch, Luis Moroder
  • Patent number: 4515808
    Abstract: Pesticidal compounds have the formula: ##STR1## wherein D represents hydrogen or a cyano group or an ethynyl group R.sub.a represents alkylA represents an alkyl group or a halogeno or trifluoromethyl groupn is 0 or an integer of 1-4, b is 0 or 1andRCOO is the residue of an acid RCOOH whose .alpha.-cyano-3-phenoxybenzyl ester has pesticidal properties. They are prepared by esterification methods.
    Type: Grant
    Filed: July 26, 1983
    Date of Patent: May 7, 1985
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay
  • Patent number: 4514419
    Abstract: Hydrazinecarboxamides and carbothioamides of the formula ##STR1## wherein R.sub.1 is selected from alkyl, cyanoalkyl, hydroxyalkyl, and benzyl, R.sub.2 is hydrogen or alkyl, Y is oxygen or sulfur, n is 0-5, and Z is substituted for hydrogen and independently selected from halogen, alkyl, alkoxy, phenoxy, trifluoromethyl, and nitro are useful as nematicides when applied to or incorporated into nematode-infested soil.
    Type: Grant
    Filed: May 18, 1983
    Date of Patent: April 30, 1985
    Assignees: FMC Corporation, Kanagawa Chemical Laboratory, Ltd.
    Inventors: Philip A. Cruickshank, Carmine P. DiSanzo, Kiyosi Kondo, Hiromichi Kono
  • Patent number: 4514340
    Abstract: A phenylethyl substituted dimer of ethylene and maleic anhydride, named 7-phenyloctane-(1,2),(5,6)-dianhydride, is chemically synthesized by(a) alkylating alkyl 2,4-dihalobutyrate with alkyl 2-cyano-3-phenylbutyrate,(b) alkylating the resulting halide condensation product with a carboxylate selected from the group consisting of trialkyl ethane-1,1,2-tricarboxylate and dimethyl cyanoethane-1,2-dicarboxylate,(c) acid hydrolyzing the resulting tetra or pentaester accompanied by decarboxylating, and(d) dehydrating the resulting tetra-acid to yield the desired phenylethyl substituted dimer of ethylene and maleic anhydride,wherein the alkyls in the butyrate and carboxylate ester groups each contain from one to about four carbon atoms and halo is selected from the group consisting of bromo, chloro and iodo.
    Type: Grant
    Filed: September 12, 1983
    Date of Patent: April 30, 1985
    Assignee: Monsanto Company
    Inventors: Jacob S. Tou, Alfred A. Schleppnik
  • Patent number: 4512931
    Abstract: A process is described by which the pair of cyhalothrin isomers represented by (R)-.alpha.-cyano-3-phenoxybenzyl (1R,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate and its enantiomer is converted by base catalyzed epimerization in solution into the insecticidally more useful isomer pair represented by (S)-.alpha.-cyano-3-phenoxybenzyl (1R,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate and its enantiomer, which may be caused to crystallize out from the solution.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: April 23, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael J. Robson
  • Patent number: 4512929
    Abstract: The invention describes new aromatic diisocyanates having the formulas: ##STR1## in which R is an alkyl radical with 1 to 12 carbon atoms. Preferably they are 1-alkyl-2-isocyanatomethyl-4-isocyanatobenzenes and/or 1-alkyl-4-isocyanatomethyl-2-isocyanatobenzenes and, particularly, 1-methyl-2-isocyanatomethyl-4- and -6-isocyanatobenzene and/or 1-methyl-4-isocyanatomethyl-2-isocyanatobenzene. The new diisocyanates are preferably prepared by phosgenation of the corresponding diamines and subsequent thermal cleavage of the carbamic acid chlorides formed on an intermediary basis and are used for the preparation of plastics, preferably of polyurethanes, and crop protection agents.
    Type: Grant
    Filed: March 25, 1983
    Date of Patent: April 23, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Erwin Hahn, Peter Neumann
  • Patent number: 4513146
    Abstract: Ester is produced by reacting highly hindered carboxylic acid or salt thereof represented by the formula ##STR1## wherein a. R.sub.3, R.sub.4, and R.sub.5 are each independently a monovalent organo group, andb. M is hydrogen, monovalent metal, or the monovalent fractional part of a polyvalent metal,with organic carbonate represented by the formula ##STR2## wherein R.sub.1 and R.sub.2 are each independently monovalent organic groups which may be the same or different, and wherein the alpha carbon of at least one of R.sub.1 and R.sub.2 is substantially sterically unhindered.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: April 23, 1985
    Assignee: PPG Industries, Inc.
    Inventor: Ralph B. Thompson
  • Patent number: 4510097
    Abstract: This invention relates to novel hindered cycloaliphatic monoisocyanates of the general formula: ##STR1## wherein R.sub.1 -R.sub.7 are members of the group consisting of H, alkyl, cycloalkyl, aryl, alkaryl, aralkyl or mixtures thereof wherein the alkyl groups contain 1-18 carbon atoms, the cycloalkyl groups contain 4-8 carbon atoms and the aryl groups contain 6-14 carbon atoms with the proviso that where R.sub.3 is a group member other than H, R.sub.1, R.sub.2, R.sub.4 and R.sub.5 can be H and with the further proviso that where R.sub.3 is H at least two of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 are group members other than H and x is 1 to 7. Other novel dihindered intermediate compositions include aliphatic monoamines.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: April 9, 1985
    Assignee: W. R. Grace & Co.
    Inventors: Clifton L. Kehr, Walter R. Wszolek, Nelson S. Marans
  • Patent number: 4510098
    Abstract: A novel crystalline modification of an enantiomeric pair of isomers of the insecticide cyhalothrin having improved handling characteristics.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: April 9, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: John Crosby
  • Patent number: 4510160
    Abstract: A novel crystalline material consisting of a enantiomeric pair of cyhalothrin isomers in the form of the racemic mixture and having greater insecticidal activity than cyhalothrin itself is described, together with a process for obtaining the enantiomeric pair of isomers by crystallization from concentrated cyhalothrin solutions in lower alkanols or liquid alkanes.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: April 9, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael J. Robson
  • Patent number: 4500459
    Abstract: A 11,11,12,12,-tetracyano-9,10-antraquinondimethane compound of the general formula ##STR1## wherein Z.sub.2, Z.sub.3, Z.sub.6 and Z.sub.7 each is H, halogen, alkyl, phenyl, alkylphenyl, hydroxyalkyl, carboxyalkyl, hydroxy, amino or carboxy and Z.sub.1, Z.sub.4, Z.sub.5 and Z.sub.8 each is H, Cl, hydroxy or amino; said halogen being F, Cl, Br or I and said alkyl, alkylphenyl, hydroxyalkyl and carboxyalkyl each containing up to 8 carbon atoms.The compounds within the scope of the above general formula are of value as organic conductors or organic semiconductors and can be used broadly as electronic materials.
    Type: Grant
    Filed: March 12, 1982
    Date of Patent: February 19, 1985
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shu Hotta, Tomiharu Hosaka, Wataru Shimotsuma
  • Patent number: 4496491
    Abstract: Diisocyanates corresponding to the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 (an isocyanate-containing radical) are as defined herein are made by several processes. These diisocyanates may be made by phosgenating the diamine in which the diisocyanate is based. They may also be produced by treating the bis-urethane of the tertiary alcohol corresponding to the diisocyanate with phosgene. Such diisocyanates may also be made by treating a specific type of bis-urea with hydrogen chloride. The diisocyanates corresponding to the above-given formula are particularly useful in the production of polyurethanes having good flame-proof and mechanical properties.
    Type: Grant
    Filed: July 22, 1982
    Date of Patent: January 29, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Richard Kopp, Gerhard Grogler, Helmut Reiff, Dieter Dieterich
  • Patent number: 4493800
    Abstract: A process for preparing a trifluoromethylbenzonitrile derivative of the formula: ##STR1## wherein X is hydrogen, lower alkyl, halogenated lower alkyl, lower alkoxy, nitro, hydroxyl, amino, cyano, carboxyl or sulfon which comprises reacting trifluoromethylhalogenobenzene of the formula: ##STR2## wherein X is as defined above, and Y is halogen with copper (I) cyanide in a solvent selected from the group consisting of hexamethylphosphoric triamide, N-methylpyrrolidone and a mixture thereof in the presence of a catalyst selected from the group consisting of (A) bromine, (B) iodine, (C) a combination of bromine or iodine and metallic copper and (D) copper (II) bromide, by which process the compound (I) is prepared in a good yield, and by-products are produced in a lower yield than the conventional processes.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: January 15, 1985
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Yasuhisa Furutaka, Sadamu Ishii
  • Patent number: 4491670
    Abstract: Isocyanates, or derivatives thereof, are produced from nitrobenzene or 2,4-dinitrotoluene by reaction with carbon monoxide in the presence of an iron, ruthenium, rhodium, or platinum carbonyl as catalyst.
    Type: Grant
    Filed: January 27, 1983
    Date of Patent: January 1, 1985
    Assignee: Indian Explosives Ltd.
    Inventors: Sumit Bhaduri, Krishna R. Sharma, Gopalkrishnan S. Kalpathi