Tertiary Butyl Group Patents (Class 568/784)
  • Publication number: 20150148430
    Abstract: The present disclosure provides phenolic compounds useful in the treatment of neurological conditions such as convulsions and tremors, having the structure of Formula (I): wherein R2, R4, & R5, are as defined in the detailed description; pharmaceutical compositions comprising at least one of the compounds; and methods for treating neurological conditions.
    Type: Application
    Filed: November 24, 2014
    Publication date: May 28, 2015
    Inventors: Max Baker, Rajesh Kumar Mishra, John J. Talley, Eduardo J. Martinez
  • Patent number: 8937201
    Abstract: This invention relates to processes for producing various t-butyl phenols, such as 2,6-di-tert-butyl phenol and ortho-tert-butyl phenol, by selectively reacting phenol or a substituted phenol with an isobutylene-containing C4 raffinate stream. The 2,6-di-tert-butyl phenol and ortho-tert-butyl phenol can be transalkylated to form other tert-butyl phenols, such as para-tert-butyl phenol, 2,4-di-tert-butyl phenol.
    Type: Grant
    Filed: December 3, 2010
    Date of Patent: January 20, 2015
    Assignee: SI Group, Inc.
    Inventors: Roger D'Souza, Scott Smith, Kirthivasan Nagarajan
  • Publication number: 20140020645
    Abstract: A lubricant additive, an crankcase lubricant composition and a method for reducing intake valve deposits in a spark ignition direct injection (SIDI) engine. The lubricant additive includes an aromatic compound having a boiling point under standard atmospheric conditions of from about 190° to about 270° C. The aromatic compound is effective to reduce intake valve deposits in a SIDI engine when used in an amount ranging from about 0.1 to about 5.0 percent by weight based on a total weight of a lubricant composition containing the additive.
    Type: Application
    Filed: July 18, 2012
    Publication date: January 23, 2014
    Applicant: AFTON CHEMICAL CORPORATION
    Inventors: Gregory H. GUINTHER, John T. LOPER
  • Publication number: 20130150629
    Abstract: This invention relates to processes for producing various t-butyl phenols, such as 2,6-di-ten-butyl phenol and ortho-tert-butyl phenol, by selectively reacting phenol or a substituted phenol with an isobutylene-containing C4 raffinate stream. The 2,6-di-ten-butyl phenol and ortho-tert-butyl phenol can be transalkylated to form other ten-butyl phenols, such as para-tert-butyl phenol, 2,4-di-ten-butyl phenol.
    Type: Application
    Filed: December 3, 2010
    Publication date: June 13, 2013
    Applicant: SI GROUP, INC.
    Inventors: Roger D'Souza, Scott Smith, Kirthivasan Nagarajan
  • Publication number: 20120294866
    Abstract: The present invention provides a liquid pharmaceutical formulation comprising a therapeutic protein, a surfactant and at least an antioxidant selected from the group of radical scavengers, chelating agents or chain terminators.
    Type: Application
    Filed: January 14, 2010
    Publication date: November 22, 2012
    Applicant: F. HOFFMANN-LA ROCHE AG
    Inventors: Hanns-Christian Mahler, Satya Krishna Kishore Ravuri
  • Publication number: 20090036584
    Abstract: Disclosed is an environmental stress cracking resistance improver that is composed of a compound that has in the molecule thereof a structure represented by the following general formula (I) and a molecular weight of from 200 to 2,000. Also disclosed are a method for improving environmental stress cracking resistance properties that uses the environmental stress cracking resistance improver, and a resin composition with improved environmental stress cracking resistance properties that contains the environmental stress cracking resistance improver. In the above general formula, R1 and R2 are each a hydrocarbon group having 1 to 6 carbon atoms, and may be the same or different from each other.
    Type: Application
    Filed: February 15, 2007
    Publication date: February 5, 2009
    Inventors: Keiko Fukushi, Kenji Iwamasa, Masahiko Okamoto
  • Patent number: 6960683
    Abstract: Organic amine salts of compounds of the formula: and their pharmaceutically acceptable salts, and uses in medical therapy are provided.
    Type: Grant
    Filed: July 14, 2003
    Date of Patent: November 1, 2005
    Assignee: Atherogenics, Inc.
    Inventor: Charles Q. Meng
  • Publication number: 20030092946
    Abstract: The invention concerns a method for functionalizing a phenolic compound bearing an electron-donor group, in said group para position, inter alia a method for the amidoalkylation of a phenolic compound bearing an electron-donor group, and more particularly, a phenolic compound bearing an electron-donor group preferably, in the hydroxyl group ortho position. The method for functionalizing in para position with respect to an electron-donor group carried by a phenolic compound is characterised in that the phenolic compound bearing an electron-donor group is subjected to the following steps: a first step which consists of protecting the hydroxyl group in the form of a sulphonic ester function; a second step which consists in reacting the protected phenolic compound with an electrophilic reagent; optionally, a third step deprotecting the hydroxyl group.
    Type: Application
    Filed: October 2, 2002
    Publication date: May 15, 2003
    Inventors: Charles Mioskowski, Alain Wagner, Nicolas Bensel, Virginie Pevere, Jean-Roger Desmurs
  • Patent number: 6504065
    Abstract: Reaction of a phenol with a metal salt of an alcohol produces a metal phenolate salt of a phenol. When a hindered phenol is used a hindered metal phenolate is produced. Such hindered metal phenolate salts are useful in driving the synthesis reaction of hindered phenol esters and phosphite esters to completion.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: January 7, 2003
    Assignee: General Electric Company
    Inventors: William Palmer Enlow, Gary Vincent Marlin
  • Patent number: 6444278
    Abstract: The present invention relates to 2,6-di-tert-butylphenols of the formula I in which R, A1 A2, Z1, Z2 m and n are as defined herein, and their use as stabilizers or antioxidants.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: September 3, 2002
    Assignee: Merck Patent Gesellschaft Mit Beschraenkter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause
  • Patent number: 6242609
    Abstract: A method for manufacturing a color coupler used in a silver halide photographic light-sensitive material using an ammonium trihalide. Said method for manufacturing the color coupler comprising the following step: a step for halogenating a coupling position of a four equivalent coupler using a halogenating agent, wherein said halogenating agent is said ammonium trihalide.
    Type: Grant
    Filed: April 7, 1999
    Date of Patent: June 5, 2001
    Assignee: Konica Corporation
    Inventor: Fumio Ishii
  • Patent number: 6114572
    Abstract: The present invention provides compounds of the formula ##STR1## wherein X is selected from the group consisting of ##STR2## Y is thio, oxy or a methylene group; Z is hydrogen or --C(O)--(CH.sub.2).sub.m --Q wherein Q is hydrogen or --COOH and m is an integer 1, 2, 3 or 4;R.sub.1 is C.sub.1 -C.sub.6 alkyl; andR.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl;or a stereoisomer thereof; useful for the treatment of atherosclerosis and chronic inflammatory disorders; for inhibiting cytokine-induced expression of VCAM-1 and/or ICAM-1; for inhibiting the peroxidation of LDL lipid; for lowering plasma cholesterol; and as anti-oxidant chemical additives useful for preventing oxidative deterioration in organic materials.
    Type: Grant
    Filed: November 19, 1997
    Date of Patent: September 5, 2000
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Roger A. Parker, Paul S. Wright, Steven J. Busch, Kim S. Chen, Mark T. Yates
  • 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: 5288927
    Abstract: There is provided a process for reacting phenol with butene or butanol over fairly large-pore zeolites to give butylphenol with high para-selectivity. Particular zeolites for use in this reaction include ZSM-12 and zeolite beta. A particular butene or butanol reactant is isobutanol. The product of this reaction may have a high content of the mono-alkylated, tert-butyl product.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: February 22, 1994
    Assignee: Mobil Oil Corp.
    Inventors: Clarence D. Chang, Stuart D. Hellring
  • Patent number: 5276215
    Abstract: Disclosed is a one-step method for synthesis of alkylphenols which comprises reacting phenol with the corresponding olefin under adiabatic conditions in the presence of a zeolite catalyst, preferably a dealuminated Y-zeolite, a modified Y-zeolite, or a .beta.-zeolite.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: January 4, 1994
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Yu-Hwa E. Sheu, Pei-Shing Dai
  • 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: 5099076
    Abstract: The present invention is directed to a method for the preparation of p,p'-biphenol by simplified processes achieved by batch or continuous operations which comprises using phenol and isobutylene as starting materials, allowing phenol to react with isobutylene in the presence of aluminum phenoxide, oxidizing the resulting reaction liquid in the presence of an alkaline catalyst, and debutylating the reaction liquid in the presence of a debutylation catalyst.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: March 24, 1992
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Katsunori Takahashi, Mikio Kawahara, Shunji Yago, Yoshiharu Ayabe
  • Patent number: 5091594
    Abstract: For producing 2,6-di-tert-butylphenol and products therefrom, utilizing small quantities of aluminum tris-(2-tert-butylphenolate as a catalyst by reaction of 2-tert-butylphenol with isobutene in the liquid phase, the reaction is performed in the presence of diluents such as liquid saturated aliphatic or cycloaliphatic hydrocarbons, C.sub.5 -C.sub.16 alkenes of formula R.sub.1 --CH.dbd.CH.sub.2 or R.sub.2 --CH.dbd.CH--R.sub.3, C.sub.5 to C.sub.12 cycloalkenes, which contain no branching on the C.dbd.C-bond, excess isobutene or mixtures thereof, at temperatures of 0.degree. C. to 80.degree. C., pressures of 0.1 to 11 bars and catalyst amounts of 0.005 to 5 mol %, based on 2-tert-butylphenol. High conversions are obtained with few undesirable trialkylated products.
    Type: Grant
    Filed: December 11, 1990
    Date of Patent: February 25, 1992
    Assignee: Huels Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Kupper, Wolfgang H. E. Muller, Alfred Oberholz
  • Patent number: 5024775
    Abstract: Liquid mixtures of alkyl phenols composed of from 1 to 8 wt % 2-tert-butylphenol; from 4 to 12 wt % of 2,6-di-tert-butylphenol; from 4 to 12 wt % of 2-tri-tert-butylphenol; and from 65 to 80 wt % of 2,6-di-tert-butyl-4-n-butylphenol have a balance of properties rendering them ideally suited for use as stabilizers for middle distillate fuels. Such mixtures can be readily produced by an aldehyde-catalyzed alkylation procedure using n-butanol, an appropriate mixture of tertiary butylated phenols, and a strong base (e.g., NaOH, KOH, etc.).
    Type: Grant
    Filed: November 6, 1989
    Date of Patent: June 18, 1991
    Assignee: Ethyl Corporation
    Inventors: J. Vincent Hanlon, Scott A. Culley
  • 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: 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: 4708966
    Abstract: The present invention relates to novel specifically-substituted phenyl compounds, especially substituted di-tert-butyl phenol derivatives, which are effective as anti-inflammatory, analgesic and/or antipyretic agents. These phenyl compounds are substituted with a low molecular weight alkyl chain which terminates in a specific unsaturated functional group. These unsaturated functionalities are --C.tbd.CH, C.dbd.CH.sub.2, C.dbd.C.dbd.CH.sub.2, and aldehydes in the form of their acetals.The present invention further relates to pharmaceutical compositions which contain an anti-inflammatory agent of the present invention and a pharmaceutically-acceptable carrier.Finally, the present invention relates to methods for treating diseases characterized by inflammation, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: November 24, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
  • Patent number: 4665238
    Abstract: Alkylaromatic compounds may be synthesized by reacting an aromatic compound with an alkylating agent comprising a mixture of gases, including carbon monoxide and hydrogen at alkylation conditions in the presence of a dual-function-catalyst. The catalyst system which is employed for this reaction will comprise (1) a composite of oxides of copper and chromium and (2) an aluminosilicate which may be either in crystalline or amorphous form.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: May 12, 1987
    Assignee: UOP Inc.
    Inventors: Tamotsu Imai, Paul T. Barger
  • 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: 4599465
    Abstract: A process for producing an orthoalkylphenol which comprises reacting phenol with an olefin in a liquid phase in the presence of an alumina catalyst, characterized in that the water content in the liquid phase of the reaction system is maintained at a level of not higher than 250 ppm.
    Type: Grant
    Filed: June 5, 1985
    Date of Patent: July 8, 1986
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Akio Tamaru, Yoshiaki Izumisawa, Hidekichi Hashimoto, Kiyoji Kuma, Takashi Komaya, Masanobu Minagawa
  • Patent number: 4568778
    Abstract: A process for producing tert-amylphenols is described, comprising reacting isoamylene with phenols in the presence of an inorganic solid acid catalyst or an acidic ion exchange resin catalyst. This process permits efficient production of tert-amylphenols, i.e., 2,4-di-tert-amylphenol and p-tert-amylphenol. These tert-amylphenols are useful as starting materials for preparation of color formers for color photography, additives for resins, oil-soluble dyes, additives for lubricating oils, etc.
    Type: Grant
    Filed: February 7, 1985
    Date of Patent: February 4, 1986
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Makoto Imanari, Hiroshi Iwane, Takahiro Sugawara, Tadashi Ayusawa, Tadamichi Aoki
  • Patent number: 4560809
    Abstract: A process for the production of a 2,6-dialkylphenol in high yield wherein the alkyl groups are secondary or tertiary with a reduced overall production of 4-alkylphenol by-products by the aluminum phenoxide catalyzed pressure reaction of isobutylene with phenol and a mixture of 2,4-dialkylphenol and 2,4,6-trialkylphenol which may be obtained, in a cyclic process, as a bottom stream from the distillation of the reaction mixture to obtain the 2,6-dialkylphenol product.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: December 24, 1985
    Assignee: Ethyl Corporation
    Inventors: Dixie E. Goins, Harold V. Huggins, Edward A. Burt, Silas W. Holmes
  • Patent number: 4538008
    Abstract: Secondary or tertiary alkyl phenyl ethers may be induced to undergo thermal rearrangement on alumina, aluminum phosphate, or a silica-modified alumina as catalyst to afford the isomeric ortho-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst with high regioselectivity and good control over the extent of alkylation.
    Type: Grant
    Filed: April 20, 1984
    Date of Patent: August 27, 1985
    Assignee: UOP Inc.
    Inventors: Bruce E. Firth, Terry J. Rosen
  • Patent number: 4496774
    Abstract: A process is disclosed for separating nitrated phenolic compounds from other nitrated and unnitrated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their ortho-nitrated derivatives, or a mixture of two isomeric nitrated phenols or cresols or a mixture of mono- and dinitrated phenols or cresols.
    Type: Grant
    Filed: July 23, 1984
    Date of Patent: January 29, 1985
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4480140
    Abstract: Phenols alkylated in the ortho and/or para positions are produced in good yields and in the absence of isomers from phenolic compounds having at least two alkylateable ortho-ortho or ortho-para positions open. The phenolic compound is first partially chlorinated or brominated and the desired halogenated phenol having at least one open position ortho or para is reacted with an aldehyde having one to four carbon atoms and a secondary non-aromatic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the amine. The reaction is performed at a temperature of from about 0.degree. C. to about 100.degree. C. to produce an aminoalkylated halogenated phenolic compound. This aminoalkylated halogenated phenolic compound is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: October 30, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4479019
    Abstract: A process is disclosed for separating nitrated phenolic compounds from other nitrated and unnitrated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their ortho-nitrated derivatives, or a mixture of two isomeric nitrated phenols or cresols or a mixture of mono-and dinitrated phenols or cresols.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: October 23, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4475001
    Abstract: Ortho- or para-monoalkylated phenols or 2,4- or 2,6-dialkylphenols can be produced from phenolic compounds in good yields and in the absence of isomers. The starting phenol which has at least two available ortho or para positions unsubstituted is converted to a t-alkylated phenol having at least one ortho or para position unsubstituted. The desired t-alkylated phenolic compound is reacted with an aldehyde having one to four carbon atoms and a secondary aliphatic or alicyclic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the secondary amine. The reaction is conducted at a temperature in the range of about 0.degree. C., to about 100.degree. C. and the reaction produces an aminoalkylated t-alkylated phenol. The aminoalkylated phenol is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: October 2, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4423253
    Abstract: A process is disclosed for separating t-butylated phenolic compounds from other t-butylated and unbutylated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their ortho-t-butylated derivatives, or a mixture of two isomeric t-butylated phenols or cresols or a mixture of mono- and di-t-butylated phenols or cresols.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: December 27, 1983
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4398048
    Abstract: Substantially improved yields of 2,4,6-trialkylphenols result from alkylating a mixture of phenol and 2,6-dialkylphenol, the latter being a by-product of the alkylation reaction. This results flows from an unexpected synergistic effect accompanying transalkylation. The continuous method of making 2,4,6-trialkylphenol based on this property affords the highly desirable trialkylated phenols in high yield.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: August 9, 1983
    Assignee: UOP Inc.
    Inventor: Bruce E. Firth
  • Patent number: 4391998
    Abstract: Phenol is catalytically alkylated with an isopropanol or propylene alkylating agent to form high yields of an isopropylphenol product enriched in the para-isomer of isopropylphenol. Such an alkylation process is carried out under catalytic alkylation conditions including a temperature of from about 200.degree. C. to 300.degree. C. and contact with a crystalline zeolite catalyst having a silica to alumina molar ratio of at least about 12 and a constraint index of about 1 to 12.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: July 5, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Margaret M. Wu
  • Patent number: 4370506
    Abstract: Hydroxyaromatic compounds, especially phenols, are reacted with an alkyl tert.butyl ether in the presence of an acidic catalyst and the as formed light alcoholic fractions are removed by flashing.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: January 25, 1983
    Assignee: Anic S.p.A.
    Inventors: Francesco Ancillotti, Giuseppe Terzoni, Lidio Micucci, Paolo Maggioni, Pietro Panseri
  • Patent number: 4366331
    Abstract: There is disclosed a process for the production of 2,6-di-tert-alkyl-4-alkenyl phenols wherein the improvement comprises the reaction of a 2,6-di-tert-alkyl phenol with an allyl halide to yield the 2,6-di-tert-alkyl-4-alkenyl phenol through the use of a triphase or polymer bound catalyst.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: December 28, 1982
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane K. Parker
  • Patent number: 4337370
    Abstract: 2-Substituted-4,6-di-t-butylresorcinol represented by the general formula: ##STR1## wherein R represents a straight or branched alkyl group having 1 to 20 carbon atoms, a straight or branched alkenyl group having 2 to 20 carbon atoms and at least one double bond, or an aralkyl group, but the tertiary carbon atom of R is free from direct bonding to the benzene nucleus, is prepared by allowing 4,6-di-t-butylresorcinol to react with a halogen compound represented by the general formula:RXwherein R has the same meaning as defined above, and X represents a halogen atom, excluding the X bonded to the tertiary carbon of R, in an aqueous alkali solution. By further debutylization of the 2-substituted-4,6-t-butylresorcinol, 2-substituted resorcinol represented by the general formula: ##STR2## wherein R has the same meaning as defined above, but the tertiary carbon of R is free from direct bonding to the benzene nucleus, is prepared.
    Type: Grant
    Filed: October 29, 1980
    Date of Patent: June 29, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Shinichi Hasegawa
  • Patent number: 4316996
    Abstract: Detrimental color change of phenolic antioxidants during production, storage and use in rubbers is inhibited by adding during the synthesis of the phenolic antioxidant a disubstituted hydroxylamine to the catalyst neutralization solution and a substituted oxime together with a disubstituted hydroxylamine to the reaction mixture prior to filtration.
    Type: Grant
    Filed: November 17, 1980
    Date of Patent: February 23, 1982
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Jacques H. Collonge, Hans Widmer
  • Patent number: 4308407
    Abstract: Phenols with a methyl group substituted on the phenolic benzene ring, such as 2,6-di-tert-butyl-p-cresol, can be produced by reacting a halomethyl group substituted on a phenol such as 2,6-di-tert-butyl-4-chloromethylphenol, with hydrogen in the presence of a hydrogenation catalyst, such as palladium.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: December 29, 1981
    Assignee: Ethyl Corporation
    Inventors: Bernard R. Meltsner, Joseph D. Odenweller
  • Patent number: 4260832
    Abstract: There is a process disclosed for alkylating the nucleus of a phenol, said process comprising reacting an .alpha., .omega.alkanediol containing from 3 to 8 carbon atoms with a phenol having an unsubstituted nuclear position para to the phenolic hydroxyl group; said phenol being selected from the group of alkylated phenols having tertiary alkyl groups of 4 to 8 carbon atoms in both positions ortho to the phenolic hydroxyl group, in the presence of an alkali metal hydroxide or alkoxide or alkali metal at a temperature from 200.degree. to 300.degree. C. while continuously removing the water by-product as it forms and obtaining as a product said phenol having a primary hydroxy terminated alkyl group of 3 to 8 carbon atoms in said para position.
    Type: Grant
    Filed: October 29, 1979
    Date of Patent: April 7, 1981
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Dane K. Parker, Richard H. Kline
  • Patent number: 4122287
    Abstract: A method of preparing 2,6-di-tert.butyl-4-methylphenol comprising reacting 2,6-di-tert.butylphenol with formaldehyde and dimethylamine in a medium of methanol or ethanol at a temperature within the range of from 80.degree. to 90.degree. C to give a reaction mass containing N,N-dimethyl-3,5-di-tert.butyl-4-hydroxybenzylamine and readily-volatile products such as methanol or ethanol, water and bis-amine. The readily-volatile products are removed from the reaction mass by heating thereof to a temperature within the range of from 110.degree. to 140.degree. C simultaneously with purging the reaction mass with an inert gas containing a secondary amine in an amount of from 5 to 50% by volume. Thereafter, N,N-dimethyl-3,5-di-tert.butyl-4-hydroxybenzylamine is contacted with hydrogen at a molar ratio therebetween of 1:4-10 respectively on a hydrogenation catalyst at a temperature ranging from 120.degree. to 160.degree. C, to give the desired product which is then isolated.
    Type: Grant
    Filed: February 16, 1977
    Date of Patent: October 24, 1978
    Inventors: Nina Vasilievna Zakharova, Alexandr Grigorievich Liakumovich, Jury Ivanovich Michurov, Zoya Stepanovna Shalimova
  • Patent number: 4101591
    Abstract: Haloloweralkyl ethynylbenzene compounds and their derivatives which are useful for the treatment for the relief of inflammation, pain and fever.
    Type: Grant
    Filed: November 23, 1976
    Date of Patent: July 18, 1978
    Assignee: William H. Rorer, Inc.
    Inventor: Julius Diamond