Acyclic Polycarbon Hydrocarbyl Group Bonded Directly To The Benzene Ring Patents (Class 568/780)
  • Patent number: 5877381
    Abstract: The present invention provides a fluidized bed catalyst for the synthetic reaction of organic compounds which has a reduced catalyst loss. A fluidized bed catalyst for organic compound synthetic reaction, characterized in that 90% or more of the catalyst particles is in the range of 5-500 .mu.m on the weight-based particle size distribution and 90% or more of the 20-75 .mu.m particles has a crushing strength which satisfies the following equation:CS>A.multidot.d.sub..alpha.wherein CS represents a crushing strength ?g-weight/particle!,A represents a constant 0.001,d represents a particle diameter ?.mu.m!, and.alpha. represents a constant 2.
    Type: Grant
    Filed: July 1, 1996
    Date of Patent: March 2, 1999
    Assignee: Nitto Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yutaka Sasaki, Hiroshi Yamamoto, Kiyoshi Moriya, Yoshimi Nakamura
  • Patent number: 5811599
    Abstract: A process for the oxidation of hydrocarbons and their derivatives having the general formula RX, wherein R is from n-alkyl, iso-alkyl, benzyl, cyclohexyl, mono, di or tricyclic aryl, or alkenic groups and X is selected from H, OH or Cl to compounds having formula R.sup.1 XY wherein R.sup.1 =(R--H), X has the meaning defined as above and Y=OH; which comprises of reacting the appropriate hydrocarbon or it's derivative of the formula RX where R and X have the meaning given above, with a solution of aqueous hydrogen peroxide at a temperature in the range of 10.degree.-100.degree. C. in the presence of an amorphous titanium-silicate catalyst having molar chemical composition in terms of the anhydrous oxides of TiO.sub.2 : (5-400) SiO.sub.2, having an average micropore radius between 10 and 40 .ANG., an absorption band around 220 nm in the ultraviolet region, a band around 960 cm.sup.-1 in the infrared region, interatomic vectors around 1.6-1.7, 2.7-2.8, 4.1-4.2 and 5.0-5.2 .ANG.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: September 22, 1998
    Inventors: Keshavaraja Alive, Ramaswamy Arumugamangalam Venkataraman, Ratnasamy Paul
  • Patent number: 5705167
    Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: January 6, 1998
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5633411
    Abstract: Allylic styrene ether compounds of the formula: ##STR1## where R.sup.1 is an optionally substituted allylic or propargyl hydrocarbon group, and R.sup.2, R.sup.3, and R.sup.4 are independently H, C.sub.1-6 hydrocarbon or C.sub.1-6 hydrocarbonoxy groups, are prepared in a single pot reaction from relatively low cost materials. The method includes the steps of reacting a 4-acyloxystyrene of the formula ##STR2## where R is an acyl group, with at least one mole of a base which can readily saponify or hydrolyze the phenolic ester bond per mole of acyloxystyrene, and then adding to the reaction mixture an alloylating agent of the formula R.sup.1 X, where R.sup.1 is as previously defined and X is chloride, bromide, iodide, a sulfonic ester or a hydrocarbon sulfate group, to form said allylic styrene ether compound. The method may be employed to prepare mono-styryl functional compounds or di-styryl functional compounds such as 1,4-bis(4'-vinylphenoxy)but-2-ene.
    Type: Grant
    Filed: May 28, 1996
    Date of Patent: May 27, 1997
    Assignee: Loctite Corporation
    Inventors: John G. Woods, Maria Masterson
  • Patent number: 5493062
    Abstract: The present invention provides a unique and novel way of producing vinyl phenols such as p-vinyl phenol (4-hydroxystyrene--HSM). In this new process, p-.alpha.-aminoethylphenol (AEP) is heated under suitable deamination conditions of temperature and pressure and for a sufficient period of time to form the 4-hydroxystyrene (HSM).
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: February 20, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ
  • Patent number: 5475156
    Abstract: A method is provided for converting a 2,4,6-trialkylphenol, such as mesitol, to a dialkylphenol, for example 2,6-dimethylphenol, by effecting the selective oxidation of the 2,4,6-trialkylphenol, followed by the deformylation of the resulting 3, 5-dialkyl-4-hydroxybenzaldehyde.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: December 12, 1995
    Assignee: General Electric Company
    Inventors: Andrew J. Caruso, Julia L. Lee
  • Patent number: 5463141
    Abstract: The present invention provides a unique and novel way of producing vinyl phenols such as poly(4-hydroxystyrene) (PHS). In this new process, p-.alpha.-aminoethylphenol (AEP) is heated under suitable conditions of temperature and pressure and for a sufficient period of time to form the poly(4-hydroxystyrene) (PHS).
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Clanese Corporation
    Inventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ
  • Patent number: 5420363
    Abstract: An optically active tri-substituted methane compound having, as substituents, an aromatic ring group and a phenyl group having hydroxyl group at ortho or para position can be obtained by allowing a phenol compound unsubstituted at the ortho- or/and para-position to react with an optically active secondary carbinol compound having an aromatic ring group at the alpha-position in the presence of tri-substituted phosphine and diazodicarboxylate or diazodicarboxamide. These and other optically active tri-substituted methane compounds are useful as active ingredients for medicines or as intermediate compounds for preparing medicines.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: May 30, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsuru Shiraishi, Shoji Fukumoto
  • Patent number: 5414156
    Abstract: This invention relates to the process for producing ortho-isopropylated phenol derivatives having following general formula (VIII). ##STR1## (in the above formula, R.sub.1 is a hydrogen or a low alkyl group of C.sub.1 -C.sub.4)A process for producing ortho-isopropylated phenol derivatives (VIII) of the present invention is characterized by obtaining position isomer desired by means of Claisen rearrangement of phenyl allyl ether without catalyst in atmosphere, and then obtaining only one isomer by oxidation and reduction of the above-obtained position isomer. According to the present invention, ortho-alkylated phenol derivatives (VIII) having high purity at low temperature and low pressure can be prepared without producing a by-product and requirement of the complicated separation procedure.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: May 9, 1995
    Assignees: Dong Kook Pharmaceutical Co., Ltd., Ki-Beom Kwon
    Inventors: Jung H. Cho, Kie H. Nam, Wan S. Kim
  • Patent number: 5399786
    Abstract: The present invention has as purpose a process for the manufacture of tert-butylphenols, mainly of tertbutyl-4-phenols from a phenol and an alkyltert-butylether. The improvement consists in separating in at least two steps, the reaction of phenol alkylation and transalkylation/isomerization of undesirable alkyltert-butylphenols, enabling the flexibilization of the type and quality of end product, and easily adapt to the demands of the market, plus the fact that the total yield improved as well as this improvement has good industrial hygiene properties.Tert-butylphenols are useful intermediate products is the manufacture of phenolic resins or antioxydizing agents for rubber and for several plastic substances.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: March 21, 1995
    Assignee: Rhodia S/A
    Inventors: Antonio U. B. Queiroz, Lumi T. Aikawa, deceased
  • Patent number: 5356976
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 n-alkyl, isopropyl, s-butyl, cyclopentyl, cyclohexyl or .alpha.-methylbenzyl, R.sub.2 is C.sub.4 -C.sub.18 tert-alkyl or .alpha.,.alpha.-dimethylbenzyl, R.sub.3 is C.sub.1 -C.sub.28 alkyl, and R.sub.4 s methyl or ethyl, with the proviso that the --CHR.sub.3 R.sub.4 group contains at least 4 carbon atoms, are suitable for stabilizing organic material which is susceptible to degradation induced by heat, oxidation or actinic light.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: October 18, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Paul Dubs, Rita Pitteloud
  • 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: 5345002
    Abstract: The present invention is directed to oil-soluble lubricating oil additives comprising Mannich Base condensates of an alkyl substituted hydroxy aromatic compound with formaldehyde and an amine, wherein the alkyl-moiety of the aromatic compounds is derived from at least one ethylene alpha-olefin copolymer of 300 to 20,000 number average molecular weight, wherein at least about 30% of the polymer's chains contain terminal ethenylidene unsaturation. The Mannich Base condensates of this invention are useful as dispersants.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: September 6, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Won R. Song, Robert D. Lundberg, Antonio Gutierrez, Robert A. Kleist
  • Patent number: 5334775
    Abstract: A process for alkylating hydroxyaromatic compounds with a terminally unsaturated polymer in the presence of a partially or completely dehydrated heteropoly catalyst. The alkylated hydroxyaromatic compounds so formed are useful as precursors for the production of fuel and lubricant additives.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: August 2, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Antonio Gutierrez, Stuart L. Soled, Jose A. Paes
  • Patent number: 5304690
    Abstract: 4-Acetoxystyrene is reacted with a base in a solvent to form a salt of 4-hydroxystyrene via saponification. Alternatively, 4-hydroxystyrene is reacted with a base to form a salt of 4-hydroxystyrene. In the latter case, the 4-hydroxystyrene is prepared by the transesterification of 4-acetoxystyrene. Subsequently or simultaneously, the salt of 4-hydroxystyrene is reacted, preferably in situ, with di-tertiary-butyl-dicarbonate to form 4-tertiarybutoxycarbonyloxystyrene.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: April 19, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: George Kvakovszky, James H. Rea, Michael I. Sheehan, Brad L. Smith
  • 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: 5245086
    Abstract: The phenols/phenol ethers are hydroxylated by reaction with hydrogen peroxide, in the presence of a catalytically effective amount of (a) at least one alkali metal or alkaline earth metal salt of a protonic acid having a pKa in water of less than -0.1 and (b) a free protonic acid.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: September 14, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • Patent number: 5243116
    Abstract: Alkylated benzenes such as ethylbenzene and cumene are produced by alkylation and/or transalkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 30:1 and a crystalline structure which is determined by X-ray diffraction to be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: September 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5241098
    Abstract: The present invention pertains to a method of forming a salt of 4-hydroxystyrene by reacting 4-acetoxystyrene with a suitable base in a suitable solvent system. Subsequently, or simultaneously, the salt of 4-hydroxystyrene can be reacted, preferably in situ, with di-tertiary-butyl-dicarbonate to form 4-tertiary-butoxycarbonyloxystyrene.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: August 31, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: George Kvakovszky, James H. Rea, Michael T. Sheehan, Brad L. Smith
  • Patent number: 5209873
    Abstract: An electrically conductive paste composition comprises an electrically conductive powder, a solvent and an organic binder comprising one or more monohydric phenol adduct compound selected from the group consisting of:(a) a monohydric phenol adduct of an unsaturated fatty acid, its metal salt or an unsaturated fatty acid ester,(b) a saturated or unsaturated fatty acid ester of said phenol adduct (a),(c) a sulfonation product of said phenol adduct (a) and(d) an amination product of said phenol adduct. It is applied to a resin article to provide an electric circuit having an improved adhesion.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: May 11, 1993
    Assignee: Kao Corporation
    Inventors: Yuzo Yamamoto, Hiromoto Mizushima, Yumi Rakue
  • Patent number: 5118875
    Abstract: Additives of improving the low temperature flow properties and oxidative stability of hydrocarbon oils are disclosed, which comprise the alkylation of a phenol in the presence of a polar aprotic cosolvent to produce an essentially linear alkylated phenol which is condensed with an aldehyde to produce the low temperature flow improver wherein:(a) the polymer composition has a number average molecular weight of at least about 3,000 and a molecular weight distribution of at least about 1.5;(b) in the alkylated phenol reactant the alkyl groups (i) are essentially linear; (ii) have between 6 and 50 carbon atoms; and (iii) have an average number of carbon atoms between about 12 and 26; and(c) not more than about 10 mole percent of the alkyl groups on the alkylated phenol have less than 12 carbon atoms and not more than about 10 mole percent of the alkyl groups on the alkylated phenol have more than 26 carbon atoms.
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: June 2, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: David J. Martella, John J. Jaruzelski, Frank J. Chen
  • Patent number: 5098945
    Abstract: A composition containing a) a polystyrene, substituted polystyrene, copolymer or terpolymer of styrene or of a substituted styrene, polycarbonate, polyester-carbonate, polyurethane, polyamide copolyamide, polyacetyl or polyphenylene oxide and b) at least one compound of the formula I ##STR1## in which R.sub.1 is methyl or ethyl and R.sub.2 is C.sub.2 -C.sub.30 alkyl.Compounds of the formula I in which R.sub.2 is C.sub.8 -C.sub.30 alkyl are novel and are suitable for stabilizing organic materials against thermal, oxidative and actinic degradation.
    Type: Grant
    Filed: February 11, 1991
    Date of Patent: March 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rita Pitteloud, Paul Dubs
  • Patent number: 5093514
    Abstract: A process for dehydrating compounds of the formula ##STR1## where --R is --CH.dbd.CH.sub.2, --C.tbd.CH --C.tbd.N or ##STR2## in an aqueous solution thereof is disclosed. In the case where R is --CH.dbd.CH.sub.2 or --C.dbd.CH, the temperature is preferably at least 50.degree. C. and preferably 75.degree. to 100.degree. C. The base is at least 0.1N and preferably 1.0 to 8N. Preferred bases are NaOH, KOH and C.sub.5 OH. In the case where --R is C.tbd.N, the temperature preferably is 20.degree. to 50.degree. C.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: March 3, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Alan D. Grund, Ronald J. Huss, Michael H. Reimer
  • Patent number: 5087772
    Abstract: A method for preparing 4-hydroxystyrene is disclosed. The method comprises reacting 4-acetoxystyrene with a suitable alcohol in the presence of a catalytic amount of a suitable base.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: February 11, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, Lan Shen
  • Patent number: 5068368
    Abstract: A process for the preparation of ethynyl carbinols of the formula: ##STR1## wherein R" is hydrogen, a substituted or unsubstituted aliphatic or aromatic hydrocarbon, R'" is a substituted or unsubstituted aliphatic or aromatic hydrocarbon or R" and R'" together to the carbon atom to which they are joined represent a steroid, which comprises the steps ofA. reacting in a solvent system comprising an aromatic hydrocarbon, at least one lithium alkylamide selected from the group consisting of: ##STR2## wherein R is a hydrogen or lower alkyl, R' is hydrogen, lower alkyl, a substituted or unsubstituted aliphatic, alicyclic or aromatic hydrocarbon, x is an integer of 2 to 8, y and z are each 0 to 1, with acetylene to form a monolithium acetylideB. reacting in a solvent system comprising an aromatic hydrocarbon, the monolithium acetylene from Part A with a ketone of the formula R"R'"C.dbd.O, wherein R" and R'" are as hereinbefore defined, and thenC.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: November 26, 1991
    Assignee: Cyprus Foote Mineral Company
    Inventors: W. Novis Smith, Christopher Louer
  • Patent number: 5053558
    Abstract: An improved process is disclosed for the isomerization of a non-equilibrium mixture of cresols to achieve a high yield of one or more cresol isomers using a catalyst comprising a Group VIII metal, a modifier, a pentasil zeolite, and an inorganic oxide binder.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: October 1, 1991
    Assignee: UOP
    Inventors: J. W. Adriaan Sachtler, R. Joe Lawson
  • Patent number: 5041692
    Abstract: A process for alkylation of phenols comprising letting a phenol react with a vinyl-aromatic hydrocarbon substituted in the vinyl group, in the presence of an organic solvent and of an acid catalyst in an aqueous solution, and of a polymerization inhibitor.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: August 20, 1991
    Assignee: Himont Italia S.r.l.
    Inventors: Raffaele Ungarelli, Maurizio A. Beretta
  • Patent number: 5024773
    Abstract: The present invention is directed toward a method for preparing Group II metal overbased sulfurized alkylphenols. In particular, the present invention employs a sulfurization catalyst in the preparation of Group II metal overbased sulfurized alkylphenols. Use of a sulfurization catalyst in this preparation results in a product generally characterized as having lower crude sediment, a higher Total Base Number and lower viscosity than a similar product prepared without using a sulfurization catalyst.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: June 18, 1991
    Assignee: Chevron Research Company
    Inventor: Thomas V. Liston
  • Patent number: 5025095
    Abstract: Substituted diallylphenol derivatives are useful as reactive diluents for bismaleimides. Formulations comprising bismaleimides and substituted diallylphenol derivatives are particularly useful in resin transfer molding and filament winding techniques.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: June 18, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Yefim Blyakhman, Byung H. Lee
  • Patent number: 5012003
    Abstract: An improved process for preparing dithiobisphenols comprising reacting an appropriate phenol with an alkali metal hydride, an alkaline earth metal hydride or mixtures thereof and subsequently reacting the product thereof with sulfur monochloride.
    Type: Grant
    Filed: October 28, 1988
    Date of Patent: April 30, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: David H. Steinberg, John J. Luzzi
  • Patent number: 4981989
    Abstract: Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein X is selected from one or more of: (a) C.sub.1 -C.sub.24 branched or straight chain alkyl; (b) C.sub.1 -C.sub.24 branched or straight chain alkoxy; (c) ##STR2## wherein n and m are integers from 0 to 25 and the sum of n and m is less than or equal to 25; phenyl; substituted phenyl wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, trifluoromethyl, phenyl, and substituted phenyl, phenoxy; and substituted phenoxy, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, halogen, trifluoromethyl, phenyl and substituted phenyl; Q is selected from the group consisting of: ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: January 1, 1991
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
  • Patent number: 4978789
    Abstract: A process for producing an alkenyl substituted aromatic compound having the general formula (I): ##STR1## wherein Ar represents an aromatic ring, R.sup.1 represents an alkenyl group having 2 to 8 carbon atoms, p is 1, 2, or 3 provided that R.sup.1 may be the same or different when p is 2 or 3, R.sup.2 represents an alkyl group having 1 to 8 carbon atoms, q is 0, 1, or 2 provided that R.sup.2 may be the same or different when q is 2, X represents --OH or --NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 independently represent hydrogen or an alkyl group having 1 to 2 carbon atoms, n is 1 or 2, provided that the sum of p and q is 1, 2, or 3 comprising the step of catalytically dehydrogenating an alkyl substituted aromatic compound having the general formula (III): ##STR2## wherein R.sup.5 represents an alkyl group having 2 to 8 carbon atoms and Ar, R.sup.2, X, p, q, and n are the same as defined above, n is 1 or 2, provided that R.sup.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: December 18, 1990
    Inventors: Katsuo Taniguchi, Shigeki Fujikawa, Yoshito Kurano
  • Patent number: 4870216
    Abstract: Phenols are selectively orthoalkylated in higher yields by the reverse addition of a phenol-aluminum phenoxide mixture to an olefin at alkylation temperature and under pressure sufficient to maintain a liquid olefin phase.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: September 26, 1989
    Assignee: Ethyl Corporation
    Inventors: Jeffrey F. King, Charles W. Matthews, Eric S. Batman
  • Patent number: 4870215
    Abstract: Phenol is di-orthoalkylated in high yield by reacting, in a first stage, phenol containing only 1 mole of an aluminum phenoxide for each 100-800 moles of phenol with an olefin at 85.degree.-175.degree. C. until the reaction mixture contains 3 wt percent or less phenol and then, in a second stage, continuing the reaction at 25.degree.-80.degree. C. until the mixture contains a substantial amount of 2,6-di-alkylphenol.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: September 26, 1989
    Assignee: Ethyl Corporation
    Inventors: Steven L. Wiker, Charles W Matthews, Jeffrey F. King
  • Patent number: 4812596
    Abstract: A process is provided for converting waste distillation bottoms containing t-alkylphenols with substantial unknown constituents to useable para-t-alkylphenols. The process comprises heating the waste distillation bottoms with phenol and an acid catalyst to effect transalkylation. The waste distillation bottoms typically result from the production of para-t-alkylphenol and/or 2,4-di-t-alkylphenol.
    Type: Grant
    Filed: March 31, 1987
    Date of Patent: March 14, 1989
    Assignee: Pennwalt Corporation
    Inventors: Altaf Husain, Stanley R. Sandler
  • Patent number: 4744921
    Abstract: The present invention is directed toward a method for preparing Group II metal overbased sulfurized alkylphenols. In particular, the present invention employs a sulfurization catalyst in the preparation of Group II metal overbased sulfurized alkylphenols. Use of a sulfurization catalyst in this preparation results in a product generally characterized as having lower crude sediment, a higher Total Base Number and lower viscosity than a similar product prepared without using a sulfurization catalyst.
    Type: Grant
    Filed: October 21, 1986
    Date of Patent: May 17, 1988
    Assignee: Chevron Research Company
    Inventor: Thomas V. Liston
  • Patent number: 4731492
    Abstract: A process of ortho-alkylating arylhydroxides, e.g., phenol, by passing a mixture of arylhydroxide, olefin and an inert hydrocarbon diluent in the liquid phase through a bed of activated alumina at an elevated temperature and pressure. Conversion and selectivity is improved over that obtained without the diluent.
    Type: Grant
    Filed: March 4, 1987
    Date of Patent: March 15, 1988
    Assignee: Ethyl Corporation
    Inventors: Steven L. Wiker, S. Wendell Holmes, Jr., Dixie E. Goins
  • Patent number: 4709102
    Abstract: The production of a 2-lower alkyl phenol, e.g., 2-cresol or 2-ethylphenol, is carried out by transalkylation of a lower alkyl phenyl ether, e.g. anisole or phenetole, at an elevated temperature in the presence of a medium pore, pentasil-type molecular sieve, e.g. an H-ZSM-5 zeolite, a silicalite or an AMS-1B borosilicate, as catalyst.
    Type: Grant
    Filed: October 7, 1986
    Date of Patent: November 24, 1987
    Assignee: Celanese Corporation
    Inventor: Balaram B. G. Gupta
  • Patent number: 4691057
    Abstract: The reaction of alkali metal with aromatic hydroxy compounds is promoted by inclusion of an alcohol in the reaction mixture. The alkali metal aryloxide formed can be reacted with phosphonitrilic chloride polymers to make polyaryloxyphosphazenes.
    Type: Grant
    Filed: September 19, 1984
    Date of Patent: September 1, 1987
    Assignee: Ethyl Corporation
    Inventor: Allan A. Eisenbraun
  • Patent number: 4689175
    Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances which have a very natural leather odor and correspond to the formula ##STR1## wherein one of the two symbols R.sub.1 and R.sub.2 represents a methyl group and the other a hydrogen atom or both symbols represent a hydrogen atom and R.sub.3 represents a n-propyl, allyl, 1-propenyl-, sec.butyl, 1-buten-3-yl, isobutyl or 2-methylpropen-3-yl group.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: August 25, 1987
    Assignee: Naarden International N.V.
    Inventor: Nicolaas L. J. M. Broekhof
  • Patent number: 4661645
    Abstract: Styrene and hydroquinone are reacted to produce (1-phenylethyl) hydroquinone, i.e.
    Type: Grant
    Filed: March 6, 1986
    Date of Patent: April 28, 1987
    Assignee: Owens-Corning Fiberglas Corporation
    Inventors: David M. Lee, David A. Hutchings, Gloria M. Sieloff, G. Fred Willard
  • Patent number: 4633022
    Abstract: 2,6-dialkyl substituted phenols such as 2,6-ditertiary butylphenol are reacted with formaldehyde in methyl alcohol in the presence of an inert gas and a tertiary amine catalyst to produce a bis(3,5-di-t-butyl-4-hydroxybenzyl)ether; and the bis ether subjected to hydrogenolysis in the presence of a catalyst, a solvent and an amine to prepare a trisubstituted phenol such as 2,6-di-t-butyl-4-methyl-phenol.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: December 30, 1986
    Assignee: Koppers Company, Inc.
    Inventor: Nicholas P. Greco
  • Patent number: 4631349
    Abstract: A process using heterogeneous resin-bonded aluminum phenoxide catalyst to alkylate phenols, the catalyst per se, and a process for making the catalyst. The inventive alkylation process uses ortho-tert-butylphenoxide bonded to a phenolformaldehyde condensation resin heterogeneous catalyst to prepare 2,6-di-tert-butylphenol from isobutylene and ortho-tert-butylphenol.
    Type: Grant
    Filed: June 25, 1985
    Date of Patent: December 23, 1986
    Assignee: Ethyl Corporation
    Inventors: Dixie E. Goins, Silas W. Holmes, Edward A. Burt
  • Patent number: 4628127
    Abstract: A process for producing 2,4-di-substituted phenols wherein an olefin is reacted with phenol in the presence of a heterogeneous catalyst comprising an aluminum phenoxide bonded to an acidic solid polymeric resin to preferably form 2,4-di-substituted phenol. A process for preparing a heterogeneous catalyst and a heterogeneous catalyst having the structure(Resin --A--).sub.m Al(--OC.sub.6 R.sub.5).sub.n (11)wherein Resin is a solid polymeric resin having acidic functional groups A, m is 1 or 2, n is 2 or 3 and the R are independently selected from H, alkyl, cycloalkyl, and aralkyl. Preferably, a styrene-divinylbenzene polymeric resin of a macroreticular structure is used for the alkylation process and A is --SO.sub.3 --.
    Type: Grant
    Filed: June 25, 1985
    Date of Patent: December 9, 1986
    Assignee: Ethyl Corporation
    Inventors: Silas W. Holmes, Edward A. Burt, Dixie E. Goins
  • Patent number: 4594460
    Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: June 10, 1986
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4593129
    Abstract: A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) containing a phenol (e.g. o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution contains phenoxides and can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide and phenoxide substituents.
    Type: Grant
    Filed: April 18, 1984
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
  • Patent number: 4590304
    Abstract: An acetylenic end-capping agent of the general formula ##STR1## wherein R.sup.1 and R.sup.2 can be the same or different and are selected from the group consisting of hydrogen, C11 to C4 alkyl, phenyl and substituted phenyl, and wherein R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a saturated 5- or 6-membered ring. This end-capping agent is substantially free of Pd and Cu.Also provided is a method for producing this end-capping agent and a method for producing acetylene terminated compounds.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: May 20, 1986
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: J. Shield Wallace, Fred E. Arnold
  • Patent number: 4584417
    Abstract: p-Alkylphenols such as p-cresol are prepared by the reaction of p-hydroxyalkylphenols with water and oxygen in the presence of at least one oxide of a Group II metal having an atomic weight less than 70, preferably zinc oxide. At least part of the p-hydroxyalkylphenol contains a p-hydroxymethyl group, and it is preferably entirely p-hydroxybenzyl alcohol. The reaction temperature is about 350.degree.-550.degree. C.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: April 22, 1986
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4554388
    Abstract: This invention relates to a process for isomerization and transalkylation of alkylphenols and for phenol-derivatives in the presence of a catalyst comprising ironoxide (s) and at least one additional oxide and in the case of 2,4,6-trimethylphenol and 2,4-dimethylphenol as alkylphenol feed, of ironoxide (s) or of a catalyst comprising ironoxide (s) and at least one additional oxide.
    Type: Grant
    Filed: February 7, 1984
    Date of Patent: November 19, 1985
    Assignee: Rheinische Braunkohlenwerke Aktiengesellschaft
    Inventors: Karl-Heinz Keim, Joachim Korff
  • Patent number: 4533763
    Abstract: This invention pertains to a process for preparing hydroxy mononuclear aromatic compounds by reacting an alkali metal hydroxide with a mononuclear aromatic compound, e.g., benzene, xylene or toluene. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably copper, nickel, rhodium or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The hydroxy mononuclear aromatic compound is then formed by adding a protonating agent to the resulting reaction product, with the protonating agent liberating the hydroxy compound from the salt.
    Type: Grant
    Filed: December 14, 1983
    Date of Patent: August 6, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, George B. DeLaMater