Acyclic Hydrocarbyl Group Bonded Directly To The Benzene Ring Patents (Class 568/658)
  • Patent number: 5344997
    Abstract: A fluorided silica-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene by linear olefins to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. These catalysts also are effective in the liquid phase alkylation of alkylatable aromatics generally with a variety of alkylating agents, including olefins, alcohols, and alkyl halides.
    Type: Grant
    Filed: December 14, 1992
    Date of Patent: September 6, 1994
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 5321167
    Abstract: An alkoxidation production low in alkylene oxide and 1,4-dioxane content is prepared by reacting an alkylphenol or fatty alcohol with an alkylene oxide in the presence of an alkali fatty alkoxide obtained by direct reaction of an alkali hydroxide with a fatty alcohol at elevated temperature.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: June 14, 1994
    Assignee: Huls Aktiengesellschaft
    Inventors: Egbert Schroer, Klaus Schulze, Ekkehard Wienhofer
  • Patent number: 5302732
    Abstract: Silica-aluminas having a sodium content less than about 0.1 weight percent show increased stability when used as a catalyst for the alkylation of aromatic compounds. Where such silica-aluminas are used as the catalyst in detergent alkylation their increased stability permits continuous alkylation to be performed at lower temperatures, as a result of which the detergent alkylate product shows an incrementally higher linearity. Fluorided silica-aluminas having a sodium content of under 0.05 weight percent are particularly advantageous.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: April 12, 1994
    Assignee: UOP
    Inventors: Karl Z. Steigleder, Christine M. Conway, David M. Baldwin, Diane C. Dierking
  • Patent number: 5130435
    Abstract: Vinyl ethers of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical to or different from one another, each being hydrogen, straight-chain or branched alkyl or alkenyl of up to 12 carbon atoms, cycloalkyl or cycloalkylene of from 5 to 8 carbon atoms, aryl, alkylaryl, alkenylaryl, aralkyl and aralkenyl of from 6 to 16 carbon atoms, halogen-substituted aryl or heterocyclyl, and in addition the radicals R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, can form a cycloalkane, cycloalkene or a heterocycle, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by eliminating an alcohol from an acetal/ketal of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 5006534
    Abstract: Substituted benzyl ethers, benzyl thioethers, and benzylamines of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and represent hydrogen, alkyl, alkenyl, cycloalkyl, alkoxy, alkylthio, halogenoalkyl, sulphonylalkyl, halogenoalkoxy, halogenoalkylthio, aralkoxy, aralkylthio, halogen, nitro, cyano or hydroxyl, or represent a group of the formula ##STR2## wherein R.sup.4 and R.sup.5 are identical or different and represent hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl or acyl,R.sup.3 represents a group of the formula ##STR3## in which R.sup.6 represents hydrogen, alkyl or acyl,R.sup.7 represents hydrogen or alkyl andn represents a number from 3 to 10,B represents --CH.sub.2 --X-- or --X--CH.sub.2 --,wherein X represents O, S or NR.sup.7,and wherein R.sup.7 has the abovementioned meaning and the group ##STR4## represents a benzo-fused heterocyclic system, A in the heterocyclic radical being 3-, 4- or 5-membered and containing nitrogen, oxygen and/or sulphur as hetero-atoms.
    Type: Grant
    Filed: January 30, 1989
    Date of Patent: April 9, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus-Helmut Mohrs, Romanis Fruchtmann, Christian Kohlsdorfer
  • Patent number: 4960884
    Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: October 2, 1990
    Assignee: FMC Corporation
    Inventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
  • Patent number: 4918242
    Abstract: A process for producing the optically pure (+)- or (-)-isomer of a phenyl- or substituted-phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4902850
    Abstract: A method of purification for anethole which involves forming an aqueous emulsion of crude anethole and crystallizing anethole from the emulsion. The process provides a purified anethole having improved odor and taste.
    Type: Grant
    Filed: August 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Arizona Chemical Company
    Inventor: Curry B. Davis
  • Patent number: 4898993
    Abstract: A process is described which permits to prepare substantially pure 2-tert-butyl-4-methoxyphenol, by reacting 4-bromo-2-tert-butylphenol with a methoxide in an organic solvent.The process permits to obtain a substantially pure 2-isomer, and avoids the need for the separation of the 2- and 3-isomers.
    Type: Grant
    Filed: January 13, 1988
    Date of Patent: February 6, 1990
    Assignee: Bromine Compounds Limited
    Inventors: Abram Becker, Nurit Kornberg, Berta Croitoru
  • Patent number: 4846998
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
  • Patent number: 4814519
    Abstract: A process for the production of ethers from an olefin containing feedstock. The process includes two-stages for the production of ethers which comprises, in a first stage, isomerizing an olefin containing feedstock over a thermally stable layered metal oxide type catalyst having interspathic polymeric silica between the layers so as to produce iso-olefins and then, in a second stage, reacting the resultant iso-olefins with alcohols in the presence of an etherification catalyst so as to produce ethers from the iso-olegins.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: March 21, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4757051
    Abstract: Novel 2-tert-butyl-4-methylcyclohexanol derivatives of the general formula I ##STR1## where R.sup.1 is alkyl of 1 to 3 carbon atoms or an acyl group ##STR2## where R.sup.2 is alkyl of 1 to 5 carbon atoms, and a process for their preparation, their use as scents, and scent compositions containing compounds of the formula I.Particularly interesting compounds are 2-tert-butyl-4-methylcyclohexyl acetate and propionate.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: July 12, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Werner Hoffman, Ludwig Schuster
  • Patent number: 4710316
    Abstract: Compounds of the general formula (I) ##STR1## and compounds of the general formula (II) ##STR2## in which R.sup.1 represents --OH, --CH.sub.2 OH, --CH.sub.2 --OCH.sub.3, --CHOH--CH.sub.3, --CHO or --CH(OCH.sub.3).sub.2,R.sup.2 represents methyl or ethyl,R.sup.3 represents hydrogen or methyl, andX represents hydrogen or methyl, are disclosed.Processes for the manufacture of certain compounds of formula (I) and for those of formula (II) are also provided. The compounds are useful as perfume materials.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: December 1, 1987
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Walter Hafner, Peter Ritter, Helmut Gebauer, Marlies Regiert
  • Patent number: 4704481
    Abstract: Benzylic and aromatic mercaptans are desulphurized by contacting the mercaptan with carbon monoxide at elevated temperatures in the presence of an aqueous hydrocarbon and a cobalt carbonyl catalyst.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: November 3, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, David J. H. Smith
  • Patent number: 4700005
    Abstract: Phenolic ethers are produced by reacting a phenol with a compound selected from an alkyl halide, an aryl halide, a dialkyl sulphate and a diaryl sulphate in the presence as catalyst of an amidine.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: October 13, 1987
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4675454
    Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a Group IB metal selected from the group consisting of Cu, Ag, Au and mixtures thereof on a support.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: June 23, 1987
    Assignee: Amoco Corporation
    Inventor: Allen B. Mossman
  • Patent number: 4675455
    Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a Group VIB metal selected from the group consisting of Cr, Mo, and mixtures thereof on a support.
    Type: Grant
    Filed: April 17, 1986
    Date of Patent: June 23, 1987
    Assignee: Amoco Corporation
    Inventor: Allen B. Mossman
  • Patent number: 4675456
    Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a lanthanide series metal selected from the group consisting of the lanthanide series metals and mixtures thereof on a support.
    Type: Grant
    Filed: April 17, 1986
    Date of Patent: June 23, 1987
    Assignee: Amoco Corporation
    Inventor: Allen B. Mossman
  • Patent number: 4650604
    Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances which have the characteristic odor of vanilla and correspond to the formula ##STR1## wherein R.sub.1 or R.sub.2 represents a hydrogen atom and the other symbol an ethyl or propyl group and R.sub.3 represents a methyl or ethyl group.
    Type: Grant
    Filed: October 16, 1985
    Date of Patent: March 17, 1987
    Assignee: Naarden International N. V.
    Inventors: Nicolaas L. J. M. Broekhof, Antonius J. A. van der Weerdt
  • Patent number: 4650910
    Abstract: Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.
    Type: Grant
    Filed: March 4, 1986
    Date of Patent: March 17, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
  • Patent number: 4611084
    Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a Group VIIB metal selected from the group consisting of Mn, Re, and mixtures thereof on a support.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: September 9, 1986
    Assignee: Amoco Corporation
    Inventor: Allen B. Mossman
  • Patent number: 4562299
    Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: December 31, 1985
    Assignee: Montedison S.p.A.
    Inventors: Carlo Venturello, Mario Gambaro
  • Patent number: 4538002
    Abstract: There is disclosed a process for the production of alkylated hydroxyanisoles which consists of dehydrogenating para-isopropylphenol to para-isopropenylphenol which is then reacted with a methylating agent to yield para-isopropenylanisole which is then treated with acidic hydrogen peroxide to yield para-hydroxyanisole which is then treated with an alkylating agent to yield the alkylated hydroxyanisole. The process of this invention is especially useful for the synthesis of the food preservative butylated hydroxyanisole (BHA).
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: August 27, 1985
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Howard A. Colvin, Joel Muse, Jr., William S. Hollingshead
  • Patent number: 4533758
    Abstract: Acid Phosphates are used, in either the gas or liquid phase, to catalyze the alkylation of phenols by an alcohol to selectively form alkyl aryl ethers.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: August 6, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: James E. Wells, Victoria Eskinazi
  • Patent number: 4521635
    Abstract: Production of bis-(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of a mineral acid treated calcined alumina catalyst, quenching the catalyst with a basic compound and recovery of the desired ether by distillation following separation of the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distill and product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.
    Type: Grant
    Filed: December 16, 1983
    Date of Patent: June 4, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Frank Stevens
  • Patent number: 4501910
    Abstract: The invention concerns a process transforming an aldehyde into a corresponding alkene, of the type wherein the aldehyde is placed in the presence of a phosphoric reagent and a base in an organic solvent.The process consists in using an alcohol as the solvent and as a base a mineral base which in an aqueous medium evinces a basic strength equal to or less than that of the hydroxide ion, or a strongly basic organic base of the amine family, and in limiting the hydration rate of the reaction medium to a value at most of 10 moles of water per mole of aldehyde.
    Type: Grant
    Filed: October 12, 1982
    Date of Patent: February 26, 1985
    Assignee: Agrifurane, S.A.
    Inventors: Michel Delmas, Antoine Gaset, Yves le Bigot
  • 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: 4400566
    Abstract: Organic halides are reduced to a dechlorinated products with a catalyst mixture consisting essentially of a nickel compound, a triarylphosphine and a halide ion, in the presence of reducing means for maintaining nickel in the zero valent state.
    Type: Grant
    Filed: March 24, 1982
    Date of Patent: August 23, 1983
    Assignee: Union Carbide Corporation
    Inventor: Ismael Colon
  • 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: 4346040
    Abstract: The invention relates to a process for converting an aldehyde into a corresponding alkene and of the type wherein the aldehyde is placed in the presence of a phosphoric reagent and a base in solution in an organic aprotic solvent; the process comprising using a mineral base evincing in an aqueous medium a basic force less than or equal to that of the hydroxide ion or a strongly basic organic base of the nitrogen compounds family and adjusting the hydration rate of the reaction medium in such a manner that there are about 0.5 to 5 moles of water per mole of aldehyde.
    Type: Grant
    Filed: July 21, 1981
    Date of Patent: August 24, 1982
    Assignee: Agrifurane S.A.
    Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
  • 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: 4299996
    Abstract: Phenol compounds are O-alkylated with olefins in the presence of acid resin catalysts to give aryl alkyl ethers. In a preferred embodiment, the catalyst comprises perfluorosulfonic acid ion exchange resins.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: November 10, 1981
    Assignee: Phillips Petroleum Co.
    Inventor: Robert M. Parlman
  • 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: 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: 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