Abstract: This invention relates to an improved process for the production of urethanes (i.e. carbamic acid esters) by reacting organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of a unique catalyst system. The catalyst system consists of palladium or a palladium compound and iron oxychloride or a mixture of iron compounds containing iron oxychloride.
Type:
Grant
Filed:
April 23, 1979
Date of Patent:
August 26, 1980
Assignee:
Bayer Aktiengesellschaft
Inventors:
Robert Becker, Johann Grolig, Christian Rasp, Gerhard Scharfe
Abstract: An aromatic urethane is obtained at high yield without involving corrosion of a stainless steel reactor by interacting an aromatic nitro compound, an organic compound having at least one hydroxyl group therein and carbon monoxide in the presence of a catalyst composed of (1) palladium, ruthenium, rhodium or compounds thereof, (2) a Lewis acid, and (3) a tertiary amine. For instance, 2,4-dinitrotoluene, ethanol and carbon monoxide placed in a SUS-32 reactor are interacted in the presence of a catalyst composed of (1) 5% palladium on carbon, (2) ferric chloride, and (3) pyridine to obtain 2,4-diethyldicarbamatetoluene without corrosion of the reactor. After completion of the reaction, the catalyst and reaction product are separated from the reaction system; e.g., the insoluble catalyst is first separated and then the reaction solution is cooled down, e.g., to room temperature, to separate the reaction product as crystals, followed by separation of the crystals by filtration.
Abstract: A novel process for producing fluorinated organic compounds containing a difluoromethylene group, essentially characterized by reacting organic compounds containing a carbonyl function with molybdenum hexafluoride at room temperature and under atmospheric pressure.
Type:
Grant
Filed:
April 6, 1978
Date of Patent:
November 6, 1979
Assignee:
Institute National de Recherche Chimique Appliquee
Abstract: Aromatic urethanes are produced by interacting an aromatic nitro compound, an organic compound containing hydroxyl groups and carbon monoxide in the presence of a catalyst composed of elemental selenium or a selenium compound and of a promoter composed of a bicyclic amidine together with a phenolic compound or a carboxylic acid. The interaction proceeds smoothly with the aid of a small amount of the promoter, attended with secondary production of amino compounds only in small amounts. For instance, 2,4-diethyldicarbamatetoluene is obtained at a yield of 87% by interacting 2,4-dinitrotoluene, ethanol and carbon monoxide in the presence of a catalytic system composed of metallic selenium, 1,8-diazabicyclo(5,4,0)-undecene-7 and acetic acid.
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.
Abstract: A process for the cross-linking or chain extension of hycrocarbon polymers which contain ethylenically unsaturated groups which comprises forming an intimate mixture of the polymer with a carbamate of the formula: ##STR1## WHEREIN R.sub.1 is an optionally substituted hydrocarbyl radical, m is an integer, and A is H or an optionally substituted hydrocarbyl radical of valency m, and subjecting the mixture to heat.Novel compounds of preferred use include those in which m=1 and at least one of R and A is alkyl or 7 or more carbon atoms, or in which m=2 and A is phenylene or alkylene or alkenylene of 2 to 4 carbon atoms.
Type:
Grant
Filed:
January 6, 1978
Date of Patent:
July 3, 1979
Assignee:
Imperial Chemical Industries Limited
Inventors:
John L. Brooks, Richard Budziarek, David J. Harper
Abstract: Novel substituted thiomethyl aryl ureas having the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 through 12 carbon atoms; alkenyl containing 2 through 4 carbon atoms; ##STR2## wherein R.sub.2 is alkyl containing 1 through 4 carbon atoms; ##STR3## WHEREIN R.sub.3 is alkyl containing 1 through 6 carbon atoms and m is 1 or 2; ##STR4## wherein Z is --Cl, --Br, --I, or CF.sub.3, and n is a whole number from 1 to 3 inclusive; ##STR5## wherein Y is --H, --Cl, --Br, or --I, and n is 1 or 2, and ##STR6## --X is --H or --Cl. The compounds are useful as herbicides.
Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.
Type:
Grant
Filed:
May 25, 1976
Date of Patent:
August 8, 1978
Assignee:
Schering Aktiengesellschaft
Inventors:
Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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
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
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
Abstract: Aromatic urethanes can be produced in exceedingly improved yield when an aromatic nitro compound, an organic compound containing hydroxyl groups, and carbon monoxide are reacted in the presence of a catalyst composed of metallic (elemental) selenium or a selenium compound and a base serving as promoter, to which reaction system an aromatic amino compound and/or an aromatic urea compound which will be secondarily produced by the reaction has been previously added in order to suppress side reactions. For instance, when nitrobenzene, methanol and carbon monoxide are interacted in the presence of metallic selenium and triethylenediamine, the conversion of nitrobenzene is 68% and the percentage of formed methyl N-phenylcarbamate to the interacted nitrobenzene is 80%, whereas when the reaction is effected under the same reaction conditions indicated above with addition to the reaction system of aniline in an amount of about 15 wt.
Abstract: Poly-carbonyloxyurethanes of the formula:A O--CO--NH--O--CO--R!.sub.n (1)wherein A is a linking group to which the oxygen atoms are attached at alkyl, cycloalkyl or aryl carbon atoms, n is an integer of value at least 2, and each R which may be the same or different, is the residue of a monobasic carboxylic acid of formula R--COOH, and their salts, especially salts with cations based on teritary amines, are useful cross-linking or chain-extending agents for natural or synthetic polymers, or may be used as adhesives for binding these materials to each other or to metal substrates.
Abstract: The disclosure herein relates to 2-halo-N-(N.sup.1 -hydrocarbyloxyoxalyl-N.sup.1 -acylaminomethyl)-2',6'-dialkylacetanilides, to a process for preparing these compounds, herbicidal compositions containing same and method of use to selectively control undesired vegetation in agricultural crops, e.g., monocotyledons such as wheat, sorghum and rice and dicotyledons such as sugarbeets and soybeans.