Hydroxy Bonded Directly To The Benzene Ring (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/650)
  • Patent number: 4426332
    Abstract: A process for the preparation of resorcinol derivatives of the general formula I ##STR1## where R.sup.1 is carbalkoxy, nitrile, alkyl or H and R.sup.2 to R.sup.5 are H or lower alkyl, by reacting the corresponding cyclohexane-1,3-dione (II) with oxygen or an oxygen-containing gas in the presence of a catalytic amount of a copper compound and of from 1 to 10 moles of a hydrogen halide, or from 0.5 to 5 moles of thionyl chloride per mole of II, in an alkanol having from 1 to 6 carbon atoms, tetrahydrofuran or methyl tert.-butyl ether as the solvent, at from 0.degree. to 150 C., without the addition of a significant amount of water to the reaction mixture. Some of the resorcinol derivatives prepared are useful scents with fragrance notes of the character of the odoriferous substance of natural oak moss.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: January 17, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Thoemel, Werner Hoffmann
  • Patent number: 4409403
    Abstract: This invention relates to oxyalkylations which take place in the presence of solid acid catalysts. More particularly this invention relates to increasing the selectivity of such processes employing a solid acid catalyst, preferably a polyfluorosulfonic acid catalyst, in which an hydroxylic compound reactant reacts with an alkylene oxide reactant to produce a desired mono-oxyalkylated product which tends to react with the alkylene oxide to produce an undesired second product.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: October 11, 1983
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4393251
    Abstract: Hydrogenation catalysts which are prepared from mixed crystals of copper-zinc compounds, obtained by precipitation, of the formulaCu.sub.1.5-3 Zn.sub.1-2.5 (CO.sub.3).sub.1-2 (OH).sub.4-6.(H.sub.2 O).sub.0-1by decomposition at 200.degree.-500.degree. C., and are used for the catalytic preparation of propanediols of the formula ##STR1## where the R's may be identical or different and each is an aliphatic, araliphatic or aromatic radical, or the two R's together with the adjacent carbon atom are members of an alicyclic ring, by hydrogenating hydroxypropionaldehydes of the formula ##STR2## where R has the above meanings, and to processes for the preparation of propanediols, using such catalysts. The propane-1,3-diols obtainable by the novel process are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example of polyesters derived from the propanediols.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: July 12, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz J. Broecker, Leopold Hupfer, Franz Merger, Ernest Miesen, Juergen Paetsch, Guenter Zirker
  • Patent number: 4383126
    Abstract: A process for the preparation of a monoalkyl ether of a hydroxyphenol of the formula ##STR1## in which Z each independently is hydrogen or a substituent which is stable under the reaction conditions,R is lower alkyl, andn is 1, 2, 3 or 4,comprising reacting a hydroxyphenol of the formula ##STR2## with an alkyl halide, alkyl sulphonate or aryl sulphonate alkylating agent of the formulaR--Xin which X is a halogen atom, or an alkylsulphonyloxy or arylsulphonyloxy radical,at a temperature from about 130.degree. C. to 200.degree. C. and in the presence of an alkali metal base or alkaline earth metal base and of a diluent comprising a polyhydroxyalkyl ether having at least one OH group. Advantageously the base is sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate, the hydroxyphenol is pyrocatechol, the alkylating agent is isopropyl chloride, isopropyl C.sub.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: May 10, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Buttner, Artur Judat, Udo Allenbach, Manfred Lenthe
  • Patent number: 4328361
    Abstract: A process is disclosed for converting p-isopropenylphenol and derivatives thereof and, more particularly, oligomers of p-isopropenylphenol and derivatives thereof, to hydroquinone via monomeric intermediates [e.g. p-(2-haloisopropyl)phenol in the case of p-isopropenylphenol and oligomers thereof]. The process involves reacting the starting materials with a hydrogen halide (e.g. gaseous hydrogen chloride) in the presence of an organic solvent and subjecting the product so obtained to oxidation with hydrogen peroxide or an organic hydroperoxide.
    Type: Grant
    Filed: January 16, 1981
    Date of Patent: May 4, 1982
    Assignee: The Upjohn Company
    Inventor: Shenghong A. Dai
  • Patent number: 4324925
    Abstract: An improved process for the preparation of a polyhydric phenol by hydroxylation of a phenol with a peroxidic hydroxylating agent, is disclosed. The improvement resides in that before the hydroxylation, all or some of the mixture to be hydroxylated is treated with a cation exchanger.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: April 13, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christoph Jupe, Helmut Waldmann, Hermann Seifert
  • Patent number: 4314085
    Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediates utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.
    Type: Grant
    Filed: August 22, 1980
    Date of Patent: February 2, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4314086
    Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Daniel Michelet
  • 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: 4301307
    Abstract: Aromatic hydrocarbons and particularly phenols and phenol ethers can be hydroxylated by reacting the aromatic compound with hydrogen peroxide in a reaction medium comprising trifluoromethanesulfonic acid. High yields of hydroxylated aromatic compounds are obtained by this process which avoids the use of extremely corrosive and difficult to handle agents. Phenol is hydroxylated predominantly to hydroquinone by this process.
    Type: Grant
    Filed: December 20, 1979
    Date of Patent: November 17, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Michel Jouffret
  • Patent number: 4301088
    Abstract: A method for preparing benzyl alcohols or substituted benzyl alcohols is disclosed by decarbonylation of formic acid esters of benzyl alcohols or ring substituted benzyl alcohols, the decarbonylation being carried out in the presence of a catalyst.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: November 17, 1981
    Assignee: Dynamit Nobel AG
    Inventor: Gunther Bernhardt
  • Patent number: 4294991
    Abstract: A process for the preparation of a monoalkyl ether having the formula ##STR1## wherein R is an alkyl radical having 1 to 18 carbon atoms or C.sub.2 H.sub.5 --O--CH.sub.2 CH.sub.2 -- and R.sup.1 is hydrogen or an alkyl radical having 1 to 4 carbon atoms, which comprises reacting a compound having the formula R--OH with a mixture of a compound having the formula ##STR2## and a compound having the formula ##STR3## in the presence of an acid dehydration catalyst, wherein the weight ratio of II:III is from 5:1 to 20:1.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: October 13, 1981
    Assignee: Eastman Kodak Company
    Inventors: Michael Bellas, Robert Cahill
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • 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: 4254288
    Abstract: A method of producing an aromatic compound comprises dehydrogenating a compound having a six-membered carbocyclic ring in the molecule, the ring having a degree of saturation greater than that of a benzene ring, the dehydrogenation being carried out in the presence of a catalyst system comprising elemental palladium together with sodium carbonate and sulphur. The compound to be dehydrogenated may be a substituted cyclohexane. When the substituted cyclohexane is an alkoxycyclohexanol, the aromatic compound produced is an alkoxy phenol. In particularly useful aspect of the invention the substituted cyclohexane is a 2-alkoxycyclohexanol, the aromatic compound produced being an ortho-alkoxy phenol.
    Type: Grant
    Filed: July 6, 1979
    Date of Patent: March 3, 1981
    Assignee: Coalite Group Limited
    Inventor: Keith Gladwin
  • Patent number: 4220605
    Abstract: A process for the production of alcohols and/or aldehydes which comprises subjecting a toluene derivative having an ether linkage or linkages of the general formula: ##STR1## wherein RO is an ether grouping where R stands for a hydrocarbyl group with 1.about.20 carbon atoms which may carry an inert substituent or substituents and n stands for an integer of 1.about.2, to auto-oxidation with molecular oxygen in liquid phase to form the corresponding alcohol and/or aldehyde, characterized in that the reaction is carried out by using a lower saturated fatty acid and/or an anhydride thereof as solvent in the presence of a soluble cobalt salt and a bromine ion-supplying substance at a reaction temperature ranging from 30.degree. C. to 200.degree. C. in such manner that the conversion rate of the toluene derivative does not exceed 90%.
    Type: Grant
    Filed: December 23, 1977
    Date of Patent: September 2, 1980
    Assignees: Director General of Agency of Industrial Science and Technology, Sanko Chemical Co. Ltd., Nippon Soda Co. Ltd.
    Inventor: Juichi Imamura
  • Patent number: 4202978
    Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediates utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.
    Type: Grant
    Filed: February 8, 1978
    Date of Patent: May 13, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • 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: 4182911
    Abstract: Novel optically-active (S)- 1-aryloxy-2,3-epoxy-propane derivatives, a process for their manufacture, various intermediates used in the preparation thereof, and a process for using them for the manufacture of optically-active (S)-1-aryloxy-3-amino-2-propanol derivatives useful as .beta.-adrenergic blocking agents.
    Type: Grant
    Filed: December 20, 1977
    Date of Patent: January 8, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventor: Howard Tucker
  • Patent number: 4172960
    Abstract: Pyrogallol is prepared by (A) reacting a halo compound of formula ##STR1## where X represents Br or I, R.sup.1 represents hydrogen, secondary or tertiary alkyl of up to 10 carbon atoms, carboxy or alkoxycarbonyl of 2-5 carbon atoms and R.sup.2 represents hydrogen or alkyl of 1-4 carbon atoms, with an alkali metal alkoxide of formula ROM where M represents an alkali metal and R represents alkyl of 1-4 carbon atoms, to replace each X by OR, and then (B) dealkylating each OR and each OR.sup.2 where R.sup.2 represents alkyl of 1-4 carbon atoms and removing the R.sup.1 group where this is not hydrogen.
    Type: Grant
    Filed: December 20, 1977
    Date of Patent: October 30, 1979
    Assignee: Fisons Limited
    Inventors: Derek Baldwin, Peter S. Gates
  • Patent number: 4162326
    Abstract: Compounds having the formula ##STR1## in which one of R.sub.1 and R.sub.2 is C.sub.3 -C.sub.4 alkynoxy or C.sub.3 alkenoxy and the other is hydrogen or methoxy. The compounds have utility as insect control agents, either as insecticides or anti-juvenile hormones.
    Type: Grant
    Filed: September 27, 1978
    Date of Patent: July 24, 1979
    Assignee: Stauffer Chemical Company
    Inventor: Alexander Mihailovski
  • 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: 4147726
    Abstract: An organic hydroperoxide is hydrolyzed by acid-catalysis in a reaction medium comprising essentially a mixture of a polar solvent, e.g. a low boiling, low molecular weight alcohol and/or sulfolane and phenol. Specifically cyclohexanone and phenol are obtained from cyclohexylbenzene hydroperoxide.
    Type: Grant
    Filed: November 8, 1976
    Date of Patent: April 3, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Yulin Wu
  • Patent number: 4139545
    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: April 30, 1975
    Date of Patent: February 13, 1979
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
  • Patent number: 4138411
    Abstract: Aromatic alkenyl compounds, for example, eugenol and safrole, are isomerized, for example to isoeugenol and isosafrole, by contact with a ruthenium or osmium catalyst.
    Type: Grant
    Filed: April 14, 1976
    Date of Patent: February 6, 1979
    Assignee: Rhone-Poulenc S. A.
    Inventor: Pierre Gandilhon