Tertiary Butyl Group Patents (Class 568/784)
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Publication number: 20150148430Abstract: 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: ApplicationFiled: November 24, 2014Publication date: May 28, 2015Inventors: Max Baker, Rajesh Kumar Mishra, John J. Talley, Eduardo J. Martinez
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Patent number: 8937201Abstract: 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: GrantFiled: December 3, 2010Date of Patent: January 20, 2015Assignee: SI Group, Inc.Inventors: Roger D'Souza, Scott Smith, Kirthivasan Nagarajan
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Publication number: 20140020645Abstract: 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: ApplicationFiled: July 18, 2012Publication date: January 23, 2014Applicant: AFTON CHEMICAL CORPORATIONInventors: Gregory H. GUINTHER, John T. LOPER
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Publication number: 20130150629Abstract: 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: ApplicationFiled: December 3, 2010Publication date: June 13, 2013Applicant: SI GROUP, INC.Inventors: Roger D'Souza, Scott Smith, Kirthivasan Nagarajan
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Publication number: 20120294866Abstract: 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: ApplicationFiled: January 14, 2010Publication date: November 22, 2012Applicant: F. HOFFMANN-LA ROCHE AGInventors: Hanns-Christian Mahler, Satya Krishna Kishore Ravuri
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Publication number: 20090036584Abstract: 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: ApplicationFiled: February 15, 2007Publication date: February 5, 2009Inventors: Keiko Fukushi, Kenji Iwamasa, Masahiko Okamoto
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Patent number: 6960683Abstract: Organic amine salts of compounds of the formula: and their pharmaceutically acceptable salts, and uses in medical therapy are provided.Type: GrantFiled: July 14, 2003Date of Patent: November 1, 2005Assignee: Atherogenics, Inc.Inventor: Charles Q. Meng
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Publication number: 20030092946Abstract: 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: ApplicationFiled: October 2, 2002Publication date: May 15, 2003Inventors: Charles Mioskowski, Alain Wagner, Nicolas Bensel, Virginie Pevere, Jean-Roger Desmurs
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Patent number: 6504065Abstract: 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: GrantFiled: September 29, 2000Date of Patent: January 7, 2003Assignee: General Electric CompanyInventors: William Palmer Enlow, Gary Vincent Marlin
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Patent number: 6444278Abstract: 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: GrantFiled: October 10, 1997Date of Patent: September 3, 2002Assignee: Merck Patent Gesellschaft Mit Beschraenkter HaftungInventors: Volker Reiffenrath, Joachim Krause
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Patent number: 6242609Abstract: 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: GrantFiled: April 7, 1999Date of Patent: June 5, 2001Assignee: Konica CorporationInventor: Fumio Ishii
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Patent number: 6114572Abstract: 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: GrantFiled: November 19, 1997Date of Patent: September 5, 2000Assignee: Hoechst Marion Roussel, Inc.Inventors: Roger A. Parker, Paul S. Wright, Steven J. Busch, Kim S. Chen, Mark T. Yates
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Patent number: 5399786Abstract: 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: GrantFiled: July 13, 1993Date of Patent: March 21, 1995Assignee: Rhodia S/AInventors: Antonio U. B. Queiroz, Lumi T. Aikawa, deceased
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Patent number: 5356976Abstract: 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: GrantFiled: July 12, 1993Date of Patent: October 18, 1994Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Rita Pitteloud
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Patent number: 5288927Abstract: 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: GrantFiled: February 1, 1993Date of Patent: February 22, 1994Assignee: Mobil Oil Corp.Inventors: Clarence D. Chang, Stuart D. Hellring
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Patent number: 5276215Abstract: 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: GrantFiled: April 9, 1993Date of Patent: January 4, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Yu-Hwa E. Sheu, Pei-Shing Dai
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Patent number: 5245086Abstract: 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: GrantFiled: December 5, 1990Date of Patent: September 14, 1993Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5099076Abstract: 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: GrantFiled: October 5, 1990Date of Patent: March 24, 1992Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Katsunori Takahashi, Mikio Kawahara, Shunji Yago, Yoshiharu Ayabe
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Patent number: 5091594Abstract: 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: GrantFiled: December 11, 1990Date of Patent: February 25, 1992Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Wolfgang H. E. Muller, Alfred Oberholz
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Patent number: 5024775Abstract: 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: GrantFiled: November 6, 1989Date of Patent: June 18, 1991Assignee: Ethyl CorporationInventors: J. Vincent Hanlon, Scott A. Culley
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Patent number: 5012003Abstract: 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: GrantFiled: October 28, 1988Date of Patent: April 30, 1991Assignee: Ciba-Geigy CorporationInventors: David H. Steinberg, John J. Luzzi
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Patent number: 4812596Abstract: 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: GrantFiled: March 31, 1987Date of Patent: March 14, 1989Assignee: Pennwalt CorporationInventors: Altaf Husain, Stanley R. Sandler
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Patent number: 4708966Abstract: 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: GrantFiled: June 27, 1986Date of Patent: November 24, 1987Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4665238Abstract: 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: GrantFiled: September 9, 1985Date of Patent: May 12, 1987Assignee: UOP Inc.Inventors: Tamotsu Imai, Paul T. Barger
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Patent number: 4633022Abstract: 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: GrantFiled: September 16, 1985Date of Patent: December 30, 1986Assignee: Koppers Company, Inc.Inventor: Nicholas P. Greco
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Patent number: 4631349Abstract: 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: GrantFiled: June 25, 1985Date of Patent: December 23, 1986Assignee: Ethyl CorporationInventors: Dixie E. Goins, Silas W. Holmes, Edward A. Burt
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Patent number: 4628127Abstract: 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: GrantFiled: June 25, 1985Date of Patent: December 9, 1986Assignee: Ethyl CorporationInventors: Silas W. Holmes, Edward A. Burt, Dixie E. Goins
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Patent number: 4599465Abstract: 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: GrantFiled: June 5, 1985Date of Patent: July 8, 1986Assignee: Mitsubishi Chemical Industries, Ltd.Inventors: Akio Tamaru, Yoshiaki Izumisawa, Hidekichi Hashimoto, Kiyoji Kuma, Takashi Komaya, Masanobu Minagawa
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Patent number: 4568778Abstract: 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: GrantFiled: February 7, 1985Date of Patent: February 4, 1986Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Makoto Imanari, Hiroshi Iwane, Takahiro Sugawara, Tadashi Ayusawa, Tadamichi Aoki
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Patent number: 4560809Abstract: 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: GrantFiled: October 9, 1984Date of Patent: December 24, 1985Assignee: Ethyl CorporationInventors: Dixie E. Goins, Harold V. Huggins, Edward A. Burt, Silas W. Holmes
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Patent number: 4538008Abstract: 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: GrantFiled: April 20, 1984Date of Patent: August 27, 1985Assignee: UOP Inc.Inventors: Bruce E. Firth, Terry J. Rosen
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Patent number: 4496774Abstract: 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: GrantFiled: July 23, 1984Date of Patent: January 29, 1985Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4480140Abstract: 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: GrantFiled: March 16, 1983Date of Patent: October 30, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4479019Abstract: 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: GrantFiled: February 21, 1984Date of Patent: October 23, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4475001Abstract: 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: GrantFiled: March 17, 1983Date of Patent: October 2, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4423253Abstract: 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: GrantFiled: April 26, 1982Date of Patent: December 27, 1983Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4398048Abstract: 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: GrantFiled: October 21, 1981Date of Patent: August 9, 1983Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4391998Abstract: 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: GrantFiled: October 21, 1981Date of Patent: July 5, 1983Assignee: Mobil Oil CorporationInventor: Margaret M. Wu
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Patent number: 4370506Abstract: 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: GrantFiled: July 24, 1981Date of Patent: January 25, 1983Assignee: Anic S.p.A.Inventors: Francesco Ancillotti, Giuseppe Terzoni, Lidio Micucci, Paolo Maggioni, Pietro Panseri
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Patent number: 4366331Abstract: 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: GrantFiled: December 14, 1981Date of Patent: December 28, 1982Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane K. Parker
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Patent number: 4337370Abstract: 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: GrantFiled: October 29, 1980Date of Patent: June 29, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Yukihisa Takisawa, Shinichi Hasegawa
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Patent number: 4316996Abstract: 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: GrantFiled: November 17, 1980Date of Patent: February 23, 1982Assignee: The Goodyear Tire & Rubber CompanyInventors: Jacques H. Collonge, Hans Widmer
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Patent number: 4308407Abstract: 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: GrantFiled: August 18, 1980Date of Patent: December 29, 1981Assignee: Ethyl CorporationInventors: Bernard R. Meltsner, Joseph D. Odenweller
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Patent number: 4260832Abstract: 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: GrantFiled: October 29, 1979Date of Patent: April 7, 1981Assignee: The Goodyear Tire & Rubber CompanyInventors: Dane K. Parker, Richard H. Kline
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Patent number: 4122287Abstract: 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: GrantFiled: February 16, 1977Date of Patent: October 24, 1978Inventors: Nina Vasilievna Zakharova, Alexandr Grigorievich Liakumovich, Jury Ivanovich Michurov, Zoya Stepanovna Shalimova
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Patent number: 4101591Abstract: Haloloweralkyl ethynylbenzene compounds and their derivatives which are useful for the treatment for the relief of inflammation, pain and fever.Type: GrantFiled: November 23, 1976Date of Patent: July 18, 1978Assignee: William H. Rorer, Inc.Inventor: Julius Diamond