Carbamic Acid Patents (Class 560/132)
  • Patent number: 4260781
    Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group, and a metal reactant comprising at least one member selected from the group consisting of compounds and complexes of Group VIII of the Periodic Table.
    Type: Grant
    Filed: May 25, 1979
    Date of Patent: April 7, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: Robert J. Harvey
  • Patent number: 4258201
    Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of an effective amount of a catalyst selected from the group consisting of non-halide compounds and complexes of metals of Groups IVB, VB, VIB, VIIB, VIII, IB and IIIA of the Periodic Table. Further improved results are obtained by employing in the reaction zone at least one promoter selected from the group consisting of metals of Group IA and IIA of the Periodic Table.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: March 24, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: David Moy
  • Patent number: 4258200
    Abstract: Carboxylic acid amides are produced by the catalytic reaction of an ester and an amine is shown. Organo cobalt salts are used as the catalyst. The process is particularly useful for producing dimethylacetamide by the reaction of methyl acetate and dimethylamine.
    Type: Grant
    Filed: March 11, 1980
    Date of Patent: March 24, 1981
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Randall J. Daughenbaugh
  • Patent number: 4242520
    Abstract: A process for the production of carbamates is provided which comprises contacting an organic primary or secondary amine with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of a catalyst for the reaction and in the presence of at least one member selected from the group consisting of disulfides of the formulaR.sup.1 --S--S--R.sup.2wherein R.sup.1 and R.sup.2 comprise members selected from the group consisting of alkyl, aryl, cycloalkyl, alkaryl, aralkyl, heterocyclic, alkenyl, alkynyl, alkanoyl, aranoyl, halogenated derivatives of the foregoing groups, and derivatives of the foregoing groups in which one or more carbon atoms is replaced by an oxygen atom.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: December 30, 1980
    Assignee: Halcon Research & Development Corporation
    Inventor: David Moy
  • Patent number: 4239904
    Abstract: A process for the preparation of urethanes by reacting a tertiary amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: December 16, 1980
    Assignee: Atlantic Richfield Company
    Inventor: Haven S. Kesling, Jr.
  • Patent number: 4234580
    Abstract: Carbamate thiosulfenylcarbamoyl fluoride compounds are insecticidal and miticidal compounds and are also useful intermediates in the preparation of pesticidally active bis-carbamate disulfide compounds.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: November 18, 1980
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4179572
    Abstract: Trans-N-acyl-N-alkyl-1-amino-1,3-butadienes are prepared by contacting a conjugated azomethine with a strong base in an inert organic solvent at sub-zero temperature and thereafter acylating the resulting product. The trans-N-acyl-N-alkyl-1-amino-1,3-butadienes are useful as intermediates in the formation of substituted decahydro-quinolines, Pumiliotoxin C, and can also be used as the diene in Diels-Alder reactions or can be copolymerized with vinyl compounds.
    Type: Grant
    Filed: September 21, 1977
    Date of Patent: December 18, 1979
    Assignee: CHON Corporation
    Inventor: Wolfgang Oppolzer
  • Patent number: 4169894
    Abstract: Unsymmetrical N-substituted bis-carbamoyloxy disulfide compounds exhibit outstanding nematocidal, miticidal and insecticidal activity, coupled with substantially reduced mammalian toxicity and phytotoxicity as compared to known pesticidal compounds having a comparable spectrum of activity against insect, arachnid and nematode pests.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: October 2, 1979
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4163861
    Abstract: An aromatic urethane (e.g., methyl naphthyl urethane) is prepared by reacting an aromatic hydroxy compound, such as alpha-naphthol, with an aliphatic urethane, such as dimethyl urethane, in the presence of a catalyst consisting of a Lewis acid.
    Type: Grant
    Filed: November 15, 1977
    Date of Patent: August 7, 1979
    Assignee: Snamprogetti S.p.A.
    Inventors: Gabriello Illuminati, Ugo Romano
  • Patent number: 4163112
    Abstract: This invention discloses new chemical compounds of the formula ##STR1## wherein R.sup.1 is selected from the group consisting of hydrogen, alkyl and alkenyl; R.sup.2 is selected from the group consisting of alkyl, alkenyl, cycloalkyl and ##STR2## WHEREIN Z is selected from the group consisting of alkyl, alkenyl, alkoxy, halogen, nitro and alkylthio; p is an integer from 0 to 5; and m is the integer 0 or 1; X.sup.1 and X.sup.2 are each selected from the group consisting of hydrogen, alkyl and halogen; Y is selected from the group consisting of oxygen and sulfur; n is the integer 1 or 2; and R.sup.3 and R.sup.4 are each alkyl.
    Type: Grant
    Filed: April 4, 1977
    Date of Patent: July 31, 1979
    Assignee: Velsicol Chemical Corporation
    Inventor: Leonard J. Stach
  • Patent number: 4156784
    Abstract: Carbamates are manufactured by reaction of alcohols with urea in the presence of ion exchangers containing nickel.The products are starting materials for the manufacture of textile finishing agents, dyes and plant protection agents.
    Type: Grant
    Filed: September 9, 1977
    Date of Patent: May 29, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Harro Petersen
  • Patent number: 4154761
    Abstract: Compounds of the general formula (I): ##STR1## in which R.sup.1 represents hydrogen or a straight or branched chain alkyl group, or an acyl group of the formula --COR.sup.5 (in which R.sup.5 represents a hydrogen atom or a straight or branched chain alkyl group);R.sup.2 represents an aryl group of the formula: ##STR2## (in which R.sup.6 represents a hydrogen atom or independently one or more of the following groups, that is, hydroxy, alkoxy, alkyl, halogen, dialkylamino and trifluoromethyl, or may represent a 3,4-methylenedioxy group ##STR3## R.sup.3 and R.sup.4 may independently represent hydrogen or a straight or branched chain alkyl group; andN represents 1, 2 or 3; and pharmaceutically acceptable salts thereof; and hydrates of said compounds or salts thereof. The invention also includes processes for the production of these compounds, compositions containing them and methods of treatment using them.
    Type: Grant
    Filed: January 28, 1977
    Date of Patent: May 15, 1979
    Assignee: Allen & Hanburys Limited
    Inventors: Ian Collins, Philip D. Wicks
  • Patent number: 4150034
    Abstract: A process for the preparation of a substituted-phenyl-N-alkyl-carbamate of the formula ##STR1## wherein R.sup.1 and R.sup.2 form part of a carbamoyloxy group and are identical or different and each is hydrogen or lower alkyl,R is halogen, formyl group or a group of the formula ##STR2## in ortho or meta-position to the carbamoyloxy group, wherein X.sup.1 and X.sup.2 are identical or different and each is oxygen or sulphur andR.sup.3 and R.sup.4 are identical or different and each is alkyl, alkenyl or alkynyl or together form a 5-membered saturated or unsaturated heterocycle in which X.sup.1 and X.sup.2 are heteroatoms, said process comprising reacting a compound of the formula ##STR3## in the presence of a base with a compound of the formula ##STR4## wherein A is phenyl substituted with two or more electron withdragroups.
    Type: Grant
    Filed: August 10, 1977
    Date of Patent: April 17, 1979
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Tamas U. Kallay, Gabor Szabo, Geza Toth, Kalman Harsanyi
  • Patent number: 4143064
    Abstract: A process for the manufacture of .beta.-haloacetals or .beta.-haloketals by reaction of substituted or unsubstituted phenols with vinyl ethers in the presence of chlorine-liberating compounds and an inert diluent or solvent at a temperature of from -70 to +40.degree. C.
    Type: Grant
    Filed: March 30, 1977
    Date of Patent: March 6, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Peter Loeffler, Karl Kiehs
  • Patent number: 4140725
    Abstract: Compounds of the formula: ##STR1## are disclosed which compound are used to prepare carbamates which are stated to have utility as plant protecting agents and insecticides.
    Type: Grant
    Filed: August 29, 1977
    Date of Patent: February 20, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Kiehs, Rolf Huber
  • Patent number: 4123450
    Abstract: Alkylisocyanates are prepared by reacting a phenol or substituted phenol and phosgene in a halogenated hydrocarbon solvent with aqueous alkali metal hydroxide to produce a corresponding chloroformate, reacting the resulting chloroformate solution with aqueous alkylamine to give a corresponding N-alkylcarbamate which, after solvent is stripped, is then pyrolyzed to yield the alkyl isocyanate. Solvent and the starting phenol may be recovered and recycled to the process.
    Type: Grant
    Filed: September 22, 1977
    Date of Patent: October 31, 1978
    Assignee: FMC Corporation
    Inventor: Harry W. Weber, Jr.
  • Patent number: 4107229
    Abstract: Vinyl terminated, fully reacted urethane compositions comprise the reaction product of polyisocyanate, an hydroxyalkylated novolac and an ethylenically unsaturated alcohol. The vinyl terminated compositions are copolymerizable with ethylenically unsaturated monomers to produce thermoset polymers characterized by excellent physical properties and a high degree of resistance to acids and alkalies. The polymers are especially useful in the manufacture of molded articles and laminates and in the formulation of marine coatings.
    Type: Grant
    Filed: June 7, 1976
    Date of Patent: August 15, 1978
    Assignee: Hooker Chemicals & Plastics Corporation
    Inventors: Richard B. Tideswell, Jeffrey E. Selley
  • Patent number: 4097676
    Abstract: Aromatic urethans are prepared by reacting aromatic carbonates with aliphatic amines, within an organic solvent or not. It is preferred that a stoichiometric quantity of the amine be employed to prevent the formation of urea by-products which are likely to be formed if an excess of the amine is used. The temperature should not exceed 100.degree. C, the interval between 20.degree. and 40.degree. C being preferred. Nearly quantitative yields are obtained.
    Type: Grant
    Filed: November 22, 1976
    Date of Patent: June 27, 1978
    Assignee: Anic S.p.A.
    Inventor: Ugo Romano
  • Patent number: 4095034
    Abstract: Process for the manufacture of N-alkyl and N-alkenyl carbamates by reacting a hydroxyl compound with a carbamyl chloride essentially free from phosgene and hydrogen chloride at a temperature of from 60.degree. to 130.degree. C in alkyl or halogen benzenes as solvent.
    Type: Grant
    Filed: April 9, 1976
    Date of Patent: June 13, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Dietrich Mangold, Karl-Heinz Koenig, Christian Reitel
  • Patent number: 4086246
    Abstract: A process for the preparation of a compound of the formula: ##STR1## wherein R.sup.1 is alkyl, alkyl substituted by halogen, alkyl substituted by alkoxy, aryl, aryl substituted by halogen, aryl substituted by alkyl, aryl substituted by alkoxy, aralkyl, aralkyl substituted by alkoxy, cycloalkyl, cycloalkyl substituted by halogen, cycloalkyl substituted by alkyl or cycloalkyl substituted by alkoxy, andR.sup.2 is an aromatic group, an aromatic group substituted by alkyl, an aromatic group substituted by halogen, an aromatic group substituted by alkoxy, a heteroaromatic group, a heteroaromatic group substituted by alkyl, a heteroaromatic group substituted by halogen, or a heteroaromatic group substituted by alkoxy, by the reaction of phosgene with a phenol of the formula:R.sup.2 -OHand further by the reaction of a primary amine of the formula:R'--NH.sub.
    Type: Grant
    Filed: April 30, 1976
    Date of Patent: April 25, 1978
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara
    Inventors: Geza Toth, Istvan Toth, Tibor Montay
  • Patent number: 4082779
    Abstract: This invention relates to a novel carbamoylation method for the preparation of steroid phenolic N-disubstituted carbamate esters, and novel compounds in said method. Phenolic carbamate esters are useful for various purposes, for instance as pharmaceuticals, e.g. antitumor agents, as biocides, e.g. pesticides, and intermediates for preparing such useful compounds.
    Type: Grant
    Filed: June 24, 1976
    Date of Patent: April 4, 1978
    Assignee: Aktiebolaget Leo
    Inventors: Hans Jacob Fex, Sten Krister Kristensson, Anders Robert Stamvik
  • Patent number: 4081461
    Abstract: This invention relates to a novel carbamoylation method for the preparation of phenolic N-disubstituted carbamate esters, and novel compounds in said method. Phenolic carbamate esters are useful for various purposes, for instance as pharmaceuticals, e.g. antitumor agents, as biocides, e.g. pesticides, and intermediates for preparing such useful compounds.
    Type: Grant
    Filed: June 24, 1976
    Date of Patent: March 28, 1978
    Assignee: Aktiebolaget Leo
    Inventors: Hans Jacob Fex, Sten Krister Kristensson, Anders Robert Stamvik
  • Patent number: 4065496
    Abstract: Trans-N-acyl-N-alkyl-1-amino-1,3-butadienes are prepared by contacting a conjugated azomethine with a strong base in an inert organic solvent at sub-zero temperature and thereafter acylating the resulting product. The trans-N-acyl-N-alkyl-1-amino-1,3-butadienes are useful as intermediates in the formation of substituted decahydro-quinolines, Pumiliotoxin C, and can also be used as the diene in Diels-Alder reactions or can be copolymerized with vinyl compounds.
    Type: Grant
    Filed: January 7, 1976
    Date of Patent: December 27, 1977
    Assignee: CHON Corporation
    Inventor: Wolfgang Oppolzer
  • Patent number: 4061652
    Abstract: Urethanes of hydroxybenzotriazoles and hydroxybenzophenones which can be chemically modified upon heating have been found useful in imparting weather resistance to plastic substrates when applied as part of a UV curable resin which can be subsequently heated after cure. UV curable resins containing such urethanes and the use of such resins to treat thermoplastic substrates are also described.
    Type: Grant
    Filed: October 28, 1975
    Date of Patent: December 6, 1977
    Assignee: General Electric Company
    Inventors: Siegfried H. Schroeter, Daniel R. Olson
  • Patent number: 4060544
    Abstract: A phenyl amino compound having a tertiary amino group contain one or two N-bonded --C.sub.2 H.sub.4 CONHC(CH.sub.3).sub.2 CH.sub.2 COCH.sub.3 moieties; said tertiary amino group being bonded through the nitrogen atom to the phenyl group. These compounds are suitable for use as coupling agents in the preparation of keto-amido containing aminophenyl-azo dyestuffs.
    Type: Grant
    Filed: August 18, 1975
    Date of Patent: November 29, 1977
    Assignee: GAF Corporation
    Inventors: Lester N. Stanley, Russell E. Farris
  • Patent number: 4059615
    Abstract: This invention relates to novel .alpha.-lower alkoxy-o-cresyl carbamates having utility as insecticides and polymer intermediates.
    Type: Grant
    Filed: February 17, 1976
    Date of Patent: November 22, 1977
    Assignee: Hooker Chemicals & Plastics Corporation
    Inventor: Edward D. Weil