Ether Oxygen Bonded Directly To Benzene Ring Patents (Class 568/630)
  • Patent number: 4593142
    Abstract: Catalysts comprising mixtures of HF and metal alkoxides and mixed metal alkoxides produce a sharply peaked alkoxylation distribution during the alkoxylation of organic materials.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: June 3, 1986
    Assignee: Vista Chemical Company
    Inventor: Kang Yang
  • Patent number: 4590294
    Abstract: The invention relates to the use of hydrogen ion-exchanged layered clays in organic reactions which are catalyzed by protons. Such organic reactions include the production of ethers by the reaction of an alcohol with an olefin or an olefin oxide, the production of an ether by the reaction of a primary or secondary aliphatic alcohol or an olefin oxide, the production of an alkyl aromatic compound by the reaction of an aromatic hydrocarbon with an olefin or a C.sub.2 or higher alcohol and the production of an alcohol by the hydration of an olefin.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: May 20, 1986
    Assignee: The British Petroleum Company Limited
    Inventors: James A. Ballantine, Reginald Gregory, John H. Purnell, John M. Thomas, David J. Westlake
  • Patent number: 4579980
    Abstract: An ether compound is advantageously produced by an ether exchange reaction of a different ether compound and a hydroxy group containing compound in the presence of a heteropoly acid or an acidic salt thereof as the catalyst. The catalyst is novel and is extremely effective to the present process and brings about less by-products compared to other processes or other catalysts.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: April 1, 1986
    Assignee: Nippon Soda Co. Ltd.
    Inventors: Kiyoshi Kogoma, Norio Sone, Takashi Tobita, Masahiro Shiozaki
  • Patent number: 4578525
    Abstract: A process is presented for extracting polar organic compounds, in particular lower aliphatic alcohols, out of their aqueous solutions, which is based on the use of fluids which contain a significant amount of polyoxaalkanols, polyoxaalkanediols and/or polyoxaalkanepolyols. These compounds, by virtue of their high molar masses, their low solubility in water and their good affinity for polar organic compounds, are particularly suitable for use as extractants.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: March 25, 1986
    Assignees: Krupp Industrietechnik Werk Buckau-Wolf, Starcosa GmbH, Versuchs- und Lehranstalt fur Spiritusfabrikation und Fermentationstechno logie in Berlin
    Inventor: Harald Bruckner
  • Patent number: 4577046
    Abstract: Deamination of aromatic primary amines by diazotization and hydrogen replacement of the diazo group is accelerated in the presence of hydrogen peroxide. Yields of at least about 85% are typical, with reaction times of usually about one hour or less.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: March 18, 1986
    Assignee: University of New Mexico
    Inventors: Mark D. Hylarides, Fred A. Mettler, Jr.
  • Patent number: 4575571
    Abstract: A process for the stimulaneous halogenation and fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with the halogen in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: March 11, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4542237
    Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Syntex Pharmaceuticals International Limited
    Inventor: George C. Schloemer
  • Patent number: 4495353
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 22, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4487976
    Abstract: Phenols are etherified to products such as anisole by contacting said phenols with a low molecular weight alcohol or ether in the presence of an acid catalyst comprising a sulfated composite of one or more transition metal oxides on alumina. The process of this invention may be used to etherify, in situ, phenols present in synthetic fuel feedstocks, such as phenols present in naphthas derived from coal liquefaction. Preferred catalysts comprise oxides of tungsten, hafnium, and mixtures thereof on a high surface area gamma alumina support containing at least 2 wt. % sulfate ions.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: December 11, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventor: Dan Farcasiu
  • Patent number: 4486349
    Abstract: Process for preparing a para-quinone or ortho-quinone derivative, possibly alkoxylated or aryloxylated, which consists in oxidizing respectively the corresponding hydroquinone or pyrocatechic derivative, by means of the complex prepared, in situ or separately, by combining a cuprous salt, a hydrocarbon substituted by a cyano group and molecular oxygen, the oxidation being possibly carried out in the presence of an alkoxylating or aryloxylating agent of the hydroxylated derivative type.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: December 4, 1984
    Assignee: Delalande, S.A.
    Inventors: Michel Maumy, Patrice J. G. Capdevielle, Philippe L. Dostert, Michel Langlois
  • Patent number: 4465876
    Abstract: In a process for nitrating aromatics using lower valent nitrating agents in trifluoroacetic acid, the product yield of nitroarenes can be significantly increased by maintaining an excess of nitrating agent over the stoichiometric amount during the reaction.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: August 14, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Barton Milligan
  • Patent number: 4453018
    Abstract: An alkylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with an alkyl sulfite of the formula (RO).sub.2 SO in which R is a one to four carbon alkyl group, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4453017
    Abstract: A methylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with trimethyl phosphate, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4450306
    Abstract: La.sub.2 (HPO.sub.4).sub.3, Sr(HSO.sub.4).sub.2 and Ba(HSO.sub.4).sub.2 are used, in either the gas or liquid phase, to catalyze the alkylation of phenols by alcohol to selectively form alkyl aryl ethers.
    Type: Grant
    Filed: November 8, 1982
    Date of Patent: May 22, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Victoria Eskinazi
  • Patent number: 4447652
    Abstract: Alkyl aryl ethers may be prepared in good yields by reacting a phenol with an olefin in the presence of an unmodified cationic exchange resin bearing sulfonic acid groups at low temperature. In another variation the ethers may be prepared by using as a catalyst the aforementioned resin where from about 10 to about 90 percent of the sulfonic acid groups are in the form of their alkali metal salts and the reaction temperature is greater than about 75.degree. C.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 8, 1984
    Assignee: UOP Inc.
    Inventor: Paul R. Kurek
  • Patent number: 4418206
    Abstract: Novel compounds of the formula: ##STR1## wherein A is CHOH, CHO or COOR; R is hydrogen or a lower alkyl group of 1 to 4 carbon atoms; and the pharmaceutically acceptable, non-toxic salts of compounds in which R is hydrogen; and X is hydrogen, o-, m- or p-halo(fluoro, chloro or bromo), o-, m- or p-methyl or o-, m- or p-methoxy. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretions and as agents for the control of asthmatic attack, because of their bronchodilating activity.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: November 29, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Douglas L. Wren
  • Patent number: 4414406
    Abstract: Molybdenum compounds, particularly molybdenum sulfide, molybdenum silicide, molybdenum selenide and molybdenum telluride are useful Friedel-Crafts catalysts for the aralkylation of aromatics to produce polybenzyls, the manufacture of aromatic ketones, aromatic sulfones and aromatic esters.The foregoing processes are carried out at a temperature of about 60.degree. to 250.degree. C. and at a catalyst concentration of about 0.1 to 15% by weight of reactants. The reaction products are useful as laminates, herbicides and bactericides.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: November 8, 1983
    Assignee: Standard Oil Company (Indiana)
    Inventor: Ellis K. Fields
  • Patent number: 4412082
    Abstract: A novel process for preparing 4-hydroxyphenylacetic acid which is useful as an intermediate for pharmaceutical is provided. A method for preparing 4-hydroxyphenylacetic acid comprising the steps of first reacting benzyl phenyl ether with formaldehyde and hydrogen chloride to form 4-benzyloxybenzyl chloride, second reacting the resultant 4-benzyloxybenzyl chloride with an alkali metal cyanide in at least one solvent selected from the group consisting of water and an organic solvent to form 4-benzyloxyphenylacetonitrile, and hydrolyzing the resultant 4-benzyloxyphenylacetonitrile in the presence of an acid catalyst.
    Type: Grant
    Filed: March 2, 1982
    Date of Patent: October 25, 1983
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Motoo Mutsukado, Shin Yamada
  • Patent number: 4407757
    Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: October 4, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
  • Patent number: 4406780
    Abstract: Properties of phenol-containing hydrocarbonaceous streams are improved by first treating the stream with a C.sub.1 to C.sub.10 alcohol and an acid. If enough alcohol and acid are employed, two liquid phases are formed, an alcohol/acid phase and a hydrocarbonaceous phase. The alcohol/acid phase, which now contains phenols, can be separated and contacted with a C.sub.1 to C.sub.16 olefin or the olefin can be added in situ. In any case, oxygen-alkylation of the phenolic groups occurs.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: September 27, 1983
    Assignee: Exxon Research and Engineering Co.
    Inventors: Kenneth A. Gould, Robert B. Long
  • Patent number: 4386219
    Abstract: Hydrogenation catalysts, which have a specific surface area of from 50 to 150 square meters per gram, solely or partially contain crystals having a spinel structure and copper in the form of copper oxide, and have been obtained by precipitating copper and aluminum in a ratio of from 0.25 to 3 atoms of copper per atom of aluminum from their compounds in the presence of a carbonate at a pH of from 4.5 to 9 and calcining the resulting precipitate at from 300.degree. to 800.degree. C., for the catalytic preparation of propanediols by hydrogenating hydroxypropionaldehydes at not more than 300 bar pressure and from 50.degree. to 200.degree. C., and processes for the preparation of propanediols by the use of such catalysts.The propanediols obtainable by the process of the invention, in particular 2,2-dimethylpropane-1,3-diol, are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example corresponding polyesters.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: May 31, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
  • Patent number: 4349487
    Abstract: Phenolic compounds are etherified by contacting at elevated temperature with a mixture of methyl trichloroacetate and either a primary alkyl halide or an aromatic halide containing strongly electron-withdrawing groups in the presence of an initiator.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: September 14, 1982
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4347256
    Abstract: This invention relates to substituted isopentenyl phenyl compounds and their use as anti-juvenile hormones. The compounds have been found effective in the control of insects by inhibiting the actions of juvenile hormones. Such compounds act to induce precocious maturation of immature insects resulting in a reduction in the ecological impact of the insect. Additional effects which have been obtained include sterilization of mature insects. Based on previous research it is also believed these compounds will cause interruption of embryogenesis in insect eggs, the induction of diapause in insects and the prevention of sex pheromone secretion in insects.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: August 31, 1982
    Assignee: Cornell Research Foundation, Inc.
    Inventor: William S. Bowers
  • Patent number: 4347148
    Abstract: Nitro phenols of the general formula ##STR1## wherein R is an aliphatic substituent of at least about 40 carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants and intermediates to such additives. These nitro phenols can be conveniently prepared by nitrating appropriate phenols. Typically nitro phenols are formed by nitration of alkyl phenols having an alkyl group of at least about 50 carbon atoms.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: August 31, 1982
    Assignee: The Lubrizol Corporation
    Inventor: Kirk E. Davis
  • Patent number: 4338255
    Abstract: Novel modified lithium aluminum hydride type reducing agents obtained by reacting one equivalent of lithium aluminum hydride with one equivalent of an optically active N-substituted ephedrine of the formula, ##STR1## (wherein R.sub.1 is a C.sub.1 -C.sub.4 alkyl group or benzyl group, and Ph is phenyl group)and two equivalents of an N-substituted aniline of the formula, ##STR2## (wherein R.sub.2 is C.sub.1 -C.sub.4 alkyl group or phenyl group, and Ph is phenyl group).This reducing agent is usable for reducing the organic compounds having a carbonyl group (ketone group or aldehyde group) in their structure into the corresponding alcohols. It is particularly useful as a reducing agent for asymmetrically reducing the unsymmetrical ketones to selectively produce either an alcohol in which the asymmetric carbon atom bonded to the hydroxy group is in R-configuration or an alcohol in which said asymmetric carbon atom is in S-configuration.
    Type: Grant
    Filed: February 25, 1981
    Date of Patent: July 6, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shiro Terashima, Norihiko Tanno, Kenji Koga
  • Patent number: 4338316
    Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: July 6, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Peter R. Marsham
  • Patent number: 4326949
    Abstract: A method for separating phenols from phenol-containing streams and converting them to ethers by: (a) contacting the phenol-containing stream with a multivalent metal composition capable of forming hydroxy metal phenates with the phenols from the stream; (b) separating the hydroxy metal phenate from the stream; and (c) reacting the hydroxy metal phenate with one or more quaternary Group VA compounds represented by the formula R.sub.3 R'MOR" or R.sub.3 R'MX.
    Type: Grant
    Filed: October 24, 1980
    Date of Patent: April 27, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventor: Richard H. Schlosberg
  • Patent number: 4319981
    Abstract: A process for preparing a liquid fuel composition which comprises liquefying coal, separating a mixture of phenols from said liquefied coal, converting said phenols to the corresponding mixture of anisoles, subjecting at least a portion of the remainder of said liquefied coal to hydrotreatment, subjecting at least a portion of said hydrotreated liquefied coal to reforming to obtain reformate and then combining at least a portion of said anisoles and at least a portion of said reformate to obtain said liquid fuel composition.
    Type: Grant
    Filed: November 12, 1980
    Date of Patent: March 16, 1982
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventor: Gary M. Singerman
  • Patent number: 4314070
    Abstract: An improved process for producing meta-phenoxy benzoic acids and their lower alkyl esters in improved yields and with higher selectivity by reacting an alkali metal phenate with a lower alkyl ester of meta-halobenzoic acid in the presence of a copper sulfate catalyst.
    Type: Grant
    Filed: May 14, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Inc.
    Inventors: Fred G. Schreiber, Peter S. Gradeff
  • Patent number: 4307253
    Abstract: Procecss for the preparation of alkyl aryl ethers by reacting phenols with aliphatic ethers in the presence of strongly acid cation exchangers.
    Type: Grant
    Filed: January 7, 1980
    Date of Patent: December 22, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Neumann, Hans-Helmut Schwarz, Dieter Nachtsheim
  • Patent number: 4306095
    Abstract: The disclosure relates to novel 4-cis-prostenoic acid derivatives, for example 16-(3-chlorophenoxy)-9.alpha.,11.alpha.,15-trihydroxy-17,18,19,20-tetranor -4-cis, 13-trans-prostadienoic acid, to chemical processes for their manufacture, to pharmaceutical and veterinary compositions containing them, and to the use of the compounds in a method of luteolysis, a method of inhibiting blood platelet aggregation, and a method of inhibiting gastric acid production.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: December 15, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventor: Jean Bowler
  • Patent number: 4294992
    Abstract: Alkyl aryl ethers are produced by incrementally reacting an acid and an alkanol with a phenol and continuously removing water formed as a by-product of the reaction. Preferably, the acid is sulfuric acid; the alkanol is methanol; and the phenol is .beta.-naphthol. The process is carried out at an elevated temperature, preferably at a temperature ranging from 125.degree. to 175.degree. C.
    Type: Grant
    Filed: January 23, 1980
    Date of Patent: October 13, 1981
    Assignee: The Southland Corporation
    Inventor: Graham K. Hughes
  • Patent number: 4290961
    Abstract: Catalytic reduction of carbonyl compounds by transfer of hydrogen from alcohols to aliphatic, alicyclic, aromatic, homo- and heterocyclic ketones or aldehydes, catalyzed by rhodium or iridium complexes, characterized in that a primary or secondary alcohol of formula (I) or a glycol: ##STR1## is reacted with a ketonic compound of formula (II): ##STR2## in which R and R' and, respectively, R" and R'", optionally linked with each other according to homo- or heterocycles, indifferently represent a hydrogen atom or a hydrocarbyl group having up to 30 atoms of carbon, also substituted, provided that at least one of symbols R" and/or R'" is different respectively from R and/or R', in the presence of a complex catalyst of rhodium or of iridium selected from those having formulas (III) and (IV): ##STR3## wherein: M is selected from Rh and Ir;Chel is a chelating bidentate nitrogenous compound;L-L is a molecule of a preferably non-conjugated diolefin or two molecules of a monoolefin;X.sup.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: September 22, 1981
    Assignee: Montedison S.p.A.
    Inventors: Giovanni Mestroni, Grazia Zassinovich, Annamaria Camus
  • Patent number: 4278816
    Abstract: Phenols and thiophenols are produced by reacting the corresponding diphenyl ether compound with hydrogen sulfide in contact with an absorptive catalyst, such as charcoal, activated carbon, calcined petroleum coke, etc. Temperatures in the range of from about 300.degree. to about 900.degree. C. are employed.
    Type: Grant
    Filed: August 26, 1977
    Date of Patent: July 14, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Kyung-sup Shim
  • Patent number: 4277327
    Abstract: Phenol-containing streams are treated by an oxygen-alkylation process to convert substantially all of the phenol groups to ether groups. The oxygen-alkylation process comprises contacting the phenol-containing stream, preferably a coal liquid, with (a) a basic solution comprising one or more oxides or hydroxides of a metal selected from the group consisting of alkali and alkaline-earth metals; and (b) an alkylating agent represented by the formula RX where R is a C.sub.1 to C.sub.18 alkyl, allyl, cycloalkyl, haloalkyl, benzyl or arylalkyl group provided X is located on the alkyl portion of the compound and X is sulfate or a halide selected from the group consisting of chlorine, bromine and iodine.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: July 7, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard H. Schlosberg, Martin L. Gorbaty
  • Patent number: 4277326
    Abstract: Process for improving properties of phenol-containing hydrocarbonaceous streams such as a coal liquid by contacting stream with (a) a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of multivalent metals capable of forming hydroxy metal phenates with the phenols of the stream; and (b) one or more alkylating agents represented by the formula RX where R is a C.sub.1 to C.sub.18 group selected from the group consisting of alkyl, allyl, cycloalkyl, haloalkyl, benzyl, and arylalkyl, provided X is located on the alkyl portions of the alkylating agent and X is sulfate or a halide.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: July 7, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard H. Schlosberg, Charles G. Scouten
  • Patent number: 4263212
    Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: April 21, 1981
    Assignee: Rikagaku Kenkyusho
    Inventors: Pangbu Hong, Hiroshi Yamazaki
  • Patent number: 4262157
    Abstract: Decarboxylation of carboxylic acids using diazabicycloalkenes and, if desired, also a simple copper salt, as the means for decarboxylation.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: April 14, 1981
    Assignee: Abbott Laboratories
    Inventors: Yuji Hori, Yoshiaki Nagano, Hiroshi Taniguchi
  • Patent number: 4256844
    Abstract: Phosphoric acid is reacted with mono- or polyfunctional epoxides containing methyol or alkoxymethyl groups, to provide resins which are curable simply by heating and contain as much as about 30 weight percent of phosphoric acid. Improved flame retardancy and water resistance are imparted to structural foams by impregnating them with these resins and curing in-situ.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: March 17, 1981
    Assignee: The Dow Chemical Company
    Inventors: Patrick H. Martin, Paul G. Schrader, Robert R. Stringham
  • Patent number: 4254276
    Abstract: Phenolic ethers are prepared starting from phenol or a phenolic derivative and an alkyl carbonate which are reacted at a comparatively low temperature (below 160.degree. C.) and with good yield and selectivity by using a catalytic system composed by a base, preferably a tertiary amine, and by an iodide, either organic or inorganic.
    Type: Grant
    Filed: July 19, 1979
    Date of Patent: March 3, 1981
    Assignee: Anic, S.p.A.
    Inventors: Giuseppe Iori, Ugo Romano
  • Patent number: 4252984
    Abstract: The invention provides phenol ethers of the formula: ##STR1## wherein R is branched C.sub.3-4 alkyl, C.sub.3-4 cycloalkyl, branched cyano(C.sub.3-4 alkyl), phenyl(C.sub.2-3 alkyl), halophenyl(C.sub.2-3 alkyl), (C.sub.1-4 alkoxy)phenyl(C.sub.2-4 alkyl), or (C.sub.1-4 acyl)amino(C.sub.1-4 alkyl),alk is C.sub.1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group,X is --O--, --S-- or --SO.sub.2 --; andR.sub.1 is --C.sub.1-4 alkyl- or --C.sub.1-4 alkoxy-,in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as .beta.-adrenergic blocking agents. Intermediates are also provided.
    Type: Grant
    Filed: October 20, 1976
    Date of Patent: February 24, 1981
    Assignee: Synthelabo
    Inventors: Philippe M. J. Manoury, Icilio A. G. Cavero, Henry Najer, Don Pierre R. L. Giudicelli
  • Patent number: 4222940
    Abstract: There are disclosed substrates of the formula: ##STR1## wherein: (a) R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;(b) R.sub.2 is H or C.sub.1 -C.sub.4 alkyl with the proviso that R.sub.1 is H when R.sub.2 is alkyl, and with the proviso that R.sub.2 is H when R.sub.1 is alkyl;(c) R.sub.3 is a leaving group including hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkoxalkoxy, C.sub.1 -C.sub.7 acyloxy, and trialkylsilyloxy of less than fifteen carbons; and(d) R.sub.5(1) and R.sub.5(2) are each H, C.sub.1 -C.sub.8 alkyl, or an optionally esterified or etherified hydroxy group including hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkoxyalkoxy, C.sub.1 -C.sub.15 trialkylsilyloxy, C.sub.4 -C.sub.8 cycloalkoxy, C.sub.1 -C.sub.7 carboxyacyloxy, or unsubstituted heterocyclic ether of five to seven members, with the proviso that at least one of R.sub.5(1) and R.sub.5(2) is hydrogen.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: September 16, 1980
    Assignee: Akzona Incorporated
    Inventors: Filippus J. Zeelen, Arnoldus I. A. Broess
  • Patent number: 4192949
    Abstract: Phenol ethers are prepared by reacting phenols with dialkyl carbonates in the presence of tertiary amines and/or phosphines. The aralkyl aryl ethers and alkyl aryl ethers obtained are starting materials for the manufacture of dyes, crop protection agents and scents.
    Type: Grant
    Filed: June 15, 1978
    Date of Patent: March 11, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
  • Patent number: 4163865
    Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.
    Type: Grant
    Filed: April 3, 1978
    Date of Patent: August 7, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
  • Patent number: 4153810
    Abstract: Process for the preparation of alkyl aryl ethers by reacting aromatic hydroxy compounds with aliphatic alcohols in the presence of strongly acidic cation exchangers based on synthetic resins using the aromatic hydroxy compound in excess of the aliphatic alcohol.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: May 8, 1979
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rainer Neumann, Hans-Helmut Schwarz, Karl-Heinz Arnold
  • Patent number: 4125563
    Abstract: I have discovered a process for making nitroarylacetylenes and aminoarylacetylenes in which the aryl radical is a phenylene radical or a diphenylene radical. With the exception of p-aminophenylacetylene, the compounds produced by this process are novel. The compounds are all useful as intermediates in the preparation of addition polymers utilizing a polymeric backbone of polyimides. The addition polymers are useful as adhesives and as laminating resins.
    Type: Grant
    Filed: August 26, 1977
    Date of Patent: November 14, 1978
    Assignee: Hughes Aircraft Company
    Inventor: Robert H. Boschan
  • Patent number: T101305
    Abstract: This invention concerns novel 3-[(3-alkylamino-2-hydroxypropoxy)phenyl]-1,2-propanediols of the formula: ##STR1## wherein R is selected from the group consisting of straight or branched-chain lower alkyls (C.sub.1 -C.sub.6) and cycloalkyls (C.sub.1 -C.sub.6); R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and 2,3-dihydroxypropyl, with the proviso that R.sub.1 and R.sub.2 may not be the same; and R.sub.3 is selected from the group consisting of lower alkyls (C.sub.1 -C.sub.4) and lower alkoxys (C.sub.1 -C.sub.4); and the acid addition salts thereof. These novel compounds are useful as antiarrhythmic agents and .beta.-andrenergic blockers in mammals.This invention also concerns novel compounds of the formula ##STR2## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and 2,3-dihydroxypropyl, with the proviso that R.sub.1 and R.sub.2 may not be the same; R.sub.3 is selected from the group consisting of lower alkyls (C.sub.1 -C.sub.4) and lower alkoxys (C.sub.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: December 1, 1981
    Inventors: Joseph W. Epstein, Leon Goldman, James D. Warren