Acyclic Polycarbon Hydrocarbyl Group Bonded Directly To The Benzene Group Patents (Class 568/766)
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Patent number: 5344997Abstract: 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: GrantFiled: December 14, 1992Date of Patent: September 6, 1994Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 5319148Abstract: The preparation of pyrocatechol monoethers or pyrocatechols of the formula Ia or Ib respectively ##STR1## ( R.sup.1 and R.sup.2 =H or C.sub.1 --C.sub.8 -hydrocarbon radicals; R.sup.3 =C.sub.1 --C.sub.8 -hydrocarbon radical ) by rearranging a 2-hydroxycyclohexanone dialkyl ketal II ##STR2## a) in the gas phase in the presence of a platinmetal or in the presence of a compound of one of these metals as catalyst in order to obtain a compound Ia, orb) carrying out step a) in the presence of water in order to obtain a compound Ib. The products are used as intermediates in the synthesis of pharmaceuticals, fragrances and flavors.Type: GrantFiled: March 2, 1993Date of Patent: June 7, 1994Assignee: BASF AktiengesellschaftInventors: Michael Karcher, Horst Zimmermann, Jochem Henkelmann
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Patent number: 5302732Abstract: 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: GrantFiled: September 14, 1992Date of Patent: April 12, 1994Assignee: UOPInventors: Karl Z. Steigleder, Christine M. Conway, David M. Baldwin, Diane C. Dierking
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Patent number: 5274176Abstract: A process for the production of substituted vinylbenzenes of the general formula: ##STR1## wherein R is a lower alkyl group having 1 to 4 C atoms, R.sub.1 is hydrogen or an acetyl group and R.sub.2 is hydrogen, a lower alkyl group having 1 to 4 C atoms or a benzyl group. A trialkylhydroquinone is cyclized with an aldehyde to an acetal and the latter is pyrolized to the endproduct. The substituted vinylbenzenes are valuable intermediate products in the synthesis of antioxidants.Type: GrantFiled: October 21, 1992Date of Patent: December 28, 1993Assignee: Lonza Ltd.Inventors: Aleksander Warm, David Laffan
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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: 5235116Abstract: Provided is an improved process for preparing 2-(1-phenylethyl)hydroquinone and its diacetate salt. In this process, the differential solubility of product and starting materials hydroquinone and styrene in non-polar organic solvents is utilized to provide mono-alkylated materials which can be easily removed from the reaction mixture. A solid acid catalyst is also used which allows the isolation of product and recycle of unreacted starting materials to be accomplished on an industrial-scale continuous process.Type: GrantFiled: August 24, 1992Date of Patent: August 10, 1993Assignee: Eastman Kodak CompanyInventor: Dewey W. Fuller, Jr.
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Patent number: 5208390Abstract: A process for alkylating an aromatic polyol, such as catechol, with an alpha olefin oligomer of alpha olefins having from about 8 to 14 carbon atoms or mixtures thereof using an organic sulfonic acid catalyst which is soluble under the alkylation reaction conditions. The liquid alkyl aromatic polyol product is useful as a lubricating oil additive or lubricating oil base stock.Type: GrantFiled: October 25, 1991Date of Patent: May 4, 1993Assignee: Chevron Research and Technology CompanyInventors: Anatoli Onopchenko, Brian R. Kennedy
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Patent number: 5149888Abstract: The phenols and phenol ethers, e.g., phenol itself, are effectively hydroxylated by reacting hydrogen peroxide therewith, in the presence of a catalytically effective amount of titanium dioxide.Type: GrantFiled: February 28, 1990Date of Patent: September 22, 1992Assignee: Rone-Poulenc ChimieInventors: Michel Costantini, Eric Garcin, Michel Gubelmann, Jean-Michel Popa
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Patent number: 5132468Abstract: The alkyl hydroquinones, e.g., methyl hydroquinone (a useful intermediate in the preparation of the monomer methyl hydroquinone diacetate, itself used for the synthesis of thermotropic polymers), are prepared by reacting (C-alkylating) hydroquinone or a monoether thereof with a lower alkanal, in the vapor phase, with a catalytically effective amount of at least one solid metal oxide.Type: GrantFiled: January 18, 1991Date of Patent: July 21, 1992Assignee: Rhone-Poulenc ChimieInventors: Claude Doussain, Michel Gubelmann, Philippe-Jean Tirel
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Patent number: 5087771Abstract: A process for producing food-grade tertiary-butyl hydroquinone from impure montertiary butyl hydroquinone is provided. Impure monotertiary butyl hydroquinone crystals are agitated at an elevated temperature while in contact with a non-polar solvent under conditions to extract the majority of the impurities followed by separating purified monotertiary butyl hydroquinone crystals from the solvent at a temperature above the crystallization point of the impurities.Type: GrantFiled: December 5, 1990Date of Patent: February 11, 1992Assignee: Eastman Kodak CompanyInventor: James R. Hilderbrand
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Patent number: 5068465Abstract: This invention relates to novel 3-aryl-2-fluoro-1-olefins and their pharmacological use as dopamine beta-hydroxylase DBH inhibitors in the treatment of DBH mediated conditions such as hypertension.Type: GrantFiled: June 15, 1990Date of Patent: November 26, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: James R. McCarthy, Charlotte L. Barney, Donald P. Matthews
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Patent number: 5043494Abstract: Methylhydroquinone (MeHQ) or methyl ether derivative thereof is prepared by contacting paramethoxyphenol or para-dimethoxybenzene with an acid catalyst, preferably a solid acid catalyst, at a temperature ranging from 100.degree. to 300.degree. C.Type: GrantFiled: October 16, 1989Date of Patent: August 27, 1991Assignee: Rhone-Poulenc ChimieInventors: Michel Gubelmann, Christian Allandrieu
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Patent number: 4978789Abstract: 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: GrantFiled: July 10, 1989Date of Patent: December 18, 1990Inventors: Katsuo Taniguchi, Shigeki Fujikawa, Yoshito Kurano
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Patent number: 4959391Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.Type: GrantFiled: July 14, 1988Date of Patent: September 25, 1990Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
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Patent number: 4914245Abstract: Cultivation of a strain of the microorganism, Preussia sp., that has been deposited in the American Type Culture Collection as A.T.C.C. No. 20,923, yields a novel antibiotic substance, culpin, that has activity against a selected spectrum of microorganisms.Type: GrantFiled: April 5, 1989Date of Patent: April 3, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Gordon W. Robinson, Joseph O'Sullivan, Edward Meyers, Jerry S. Wells, Janice H. Del Mar
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Patent number: 4900476Abstract: An asymmetric synthesis for Vitamin E in an optically active pure form for 4-(2,5-diloweralkanoyloxy)-3,4,6-trimethylphenyl-butan-2-one and intermediates therein.Type: GrantFiled: January 30, 1989Date of Patent: February 13, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Ka-kong Chan, Gabriel G. Saucy
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Patent number: 4859731Abstract: Polymer dihydroxy compounds corresponding to the following formula ##STR1## in whichR.sup.1, R.sup.2, R.sup.3 =H or C.sub.1 -C.sub.4 alkyl,R.sup.4 =H or C.sub.1 -C.sub.4 alkyl,R.sup.5 =--C.sub.6 H.sub.5, --C.sub.6 H.sub.4 CH.sub.3, --CH.dbd.CH.sub.2, or --CO.sub.2 R.sup.7,R.sup.6 =C.sub.1 -C.sub.4 alkyl, aryl, or H,R.sup.7 =C.sub.1 -C.sub.4 alkyl,m=0 or 1,n=5 to 100,q=0 or 1,a process for their production and their use in thermoplastic molding compositions.Type: GrantFiled: July 25, 1988Date of Patent: August 22, 1989Assignee: Bayer AktiengesellschaftInventors: Herbert Eichenauer, Hartwig Hocker, Thomas Heitz
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Patent number: 4851587Abstract: 2-Methallyloxyphenol precursor to 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran is prepared selectively and in good yield in the etherification of an alkali metal catecholate by methallyl chloride in an improved process using the same solvent medium for both the precursor and the hydroxybenzofuran, the process characterized by a solvent medium comprising an aromatic hydrocarbon solvent, the medium also containing an amine selected from alkylamines and N-heterocyclic amines. The amine forms a quaternary salt with the methallyl chloride in situ to catalyze the etherification and the aromatic solvent permits rearrangement of the product and Claisen closure to a benzofuran intermediate without solvent exchange.Type: GrantFiled: May 31, 1988Date of Patent: July 25, 1989Assignee: FMC CorporationInventors: Borivoj Franko-Filipasic, James Snyder
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Patent number: 4849548Abstract: A 4-halomethyl-3,5-dihalo-2,6-dialkylphenol is hydrolyzed by contact with water to form a 4-hydroxy-methyl-3,5-dihalo-2,6-dialkylphenol under conditions to minimize formation of the corresponding bis-(4-hydroxy-3,5-dialkyl-2,6-dihalobenzyl) ether.Type: GrantFiled: March 21, 1988Date of Patent: July 18, 1989Assignee: The Dow Chemical CompanyInventor: Ming-Biann Liu
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Patent number: 4835323Abstract: New hydroquinones have the formula: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR2## wherein Q is (i) -OX or (ii) -PO(OR.sub.11)((O).sub.x R.sub.11); and salts thereof with organic or inorganic acid bases.The groups X and R.sub.11 and x are defined hereinafter.The compounds of formula I are useful as stabilisers in photographic materials.Type: GrantFiled: September 11, 1986Date of Patent: May 30, 1989Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4827049Abstract: This invention comprises a process for separating isomers of dihydroxybenzene (DHB) from a feed mixture comprising at least two of said isomers, which process comprises contacting the mixture at adsorption conditions with an adsorbent comprising a Y type zeolite cation exchanged with a cation in the group Ca, Ba or Li, thereby selectively adsorbing o-DHB (catechol), or K, thereby selectively adsorbing p-DHB (hydroquinone). In the case where all three isomers are present in the feed, a cation from the first group is used, the remainder of the feed mixture is removed from the adsorbent and o-DHB is recovered by desorption at desorption conditions with methanol. P-DHB is recovered from the remainder by adsorption with the same or other adsorbent listed above and desorption at desorption conditions with ethanol.Type: GrantFiled: March 28, 1988Date of Patent: May 2, 1989Assignee: UOPInventor: Hermann A. Zinnen
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Patent number: 4801735Abstract: Compounds are described of the following formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, C.sub.1-12 alkyl or C.sub.2-12 alkenyl, at least one of R.sup.1 and R.sup.2 being C.sub.1-12 alkyl or C.sub.2-12 alkenyl; X.sup.1 and X.sup.2 are each hydrogen or a protecting group; and Y is(a) --(CH.dbd.CH).sub.n Z in which n is 1, 2 or 3 and Z is --CHO, --CH.sub.2 OH, --COR.sup.3, --(CH.sub.2).sub.m --COR.sup.3 or --(CH.sub.2).sub.p CH.dbd.CH(CH.sub.2).sub.q --COR.sup.3 in which m is an integer of 1 to 12, p is an integer of 1 to 4, q is an integer of 1 to 10 and R.sup.3 is (i) --OH or (ii) --NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are each hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl, or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholino, pyrrolidinyl or piperidino ring,(b) --CH.dbd.NR.sup.6 in which R.sup.6 is (i) --OH, (ii) C.sub.1-12 alkyl optionally substituted by --OH, --COOH or --NR.sup.7 R.sup.8 where R.sup.7 and R.sup.Type: GrantFiled: November 25, 1985Date of Patent: January 31, 1989Assignee: Lilly Industries LimitedInventors: Mark A. W. Finch, John R. Harris
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Patent number: 4769500Abstract: A process for preparation of 2,3,5-trimethylhydroquinone (TMHQ) from 2,3,5-trimethylbenzoquinone (TMBQ) is disclosed, comprising reducing TMBQ with hydrogen in the presence of a platinum group metal catalyst with a silica alumina support containing an alkali metal component. This process permits preparation of TMHQ of purity as high as more than 99%.Type: GrantFiled: September 24, 1987Date of Patent: September 6, 1988Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomoyuki Yui, Akira Ito
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Patent number: 4760197Abstract: A process which comprises contacting the surface of a metal with an alkyl or acyl substituted catechol.The contacting may be effected using the substituted catechol alone or in a suitable medium for example as a solution or emulsion. The contacting is effective in providing corrosion inhibition even with lightly rusted iron surfaces.Type: GrantFiled: September 15, 1987Date of Patent: July 26, 1988Assignee: Imperial Chemical Industries PLCInventors: Bernard Tury, Glyn R. John, Edward G. Scovell
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Patent number: 4760087Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.Type: GrantFiled: May 13, 1986Date of Patent: July 26, 1988Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
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Patent number: 4689427Abstract: The present invention is directed to novel hydroquinone derivatives which are useful as intermediates for the manufacture of (R,R,R)-.alpha.-tocopherol (natural vitamin E) as well as of racemic .alpha.-tocopherol. The invention is also directed to a process for the preparation of the hydroquinone derivatives of the invention.Type: GrantFiled: November 15, 1985Date of Patent: August 25, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Marquard Imfeld
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Patent number: 4670604Abstract: 4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.Type: GrantFiled: November 22, 1985Date of Patent: June 2, 1987Assignee: Ciba-Geigy CorporationInventors: Andreas Beck, Alfred Sallmann, Robert W. Lang, Paul Wenk
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Patent number: 4661601Abstract: New compounds having the formula 1 ##STR1## wherein W is hydrogen, halogen, n-alkyl, --NHCOR.sup.1, --COR.sup.1, or phenoxyacetylamino optionally substituted by one or two C.sub.1-12 straight- or branched chain alkyl, X is a substituent in the coupling position and is selected from hydrogen, chlorine, bromine, --SR.sup.11 or a nitrogen-containing heterocyclic residue attached at a ring nitrogen atom, and Y is a group having the formula 2 ##STR2## wherein Q is selected from the residues: --COOR.sup.4 or --CONR.sup.4 R.sup.5, --OM, --NR.sup.7 R.sup.8, --PO(OR.sup.9)[O].sub.x R.sup.10 with X=0 or 1, --SO.sub.2 OH, --SO.sub.2 NR.sup.4 R.sup.5 or CN. The groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, M, k and n are defined hereinafter.These compounds are used as black color couplers in photographic materials.Type: GrantFiled: April 3, 1985Date of Patent: April 28, 1987Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4632771Abstract: This invention relates to normally liquid lubricating oil additives which provide both anti-oxidant and friction-modifying properties when added to lubricating oil. In particular, this invention relates to C.sub.14 to C.sub.18 alkyl catechol lubricating oil additives which are normally liquid at typical storage temperatures.Type: GrantFiled: March 14, 1985Date of Patent: December 30, 1986Assignee: Chevron Research CompanyInventors: Thomas V. Liston, Warren Lowe, Vernon R. Small
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Patent number: 4618627Abstract: A catechol derivative represented by the formula ##STR1## The compounds of this invention are useful for the prophylaxis and treatment for various allergic diseases, ischemic heart diseases and inflammations caused by slow reacting substance of anaphylaxis (SRS-A), since the compounds inhibit very potently the formation and release of SRS-A.Type: GrantFiled: May 11, 1984Date of Patent: October 21, 1986Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka
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Patent number: 4599464Abstract: Novel compositions useful as antioxidants are formed by the reaction of resorcinol with an alkenylbenzene.Type: GrantFiled: October 17, 1985Date of Patent: July 8, 1986Assignee: Koppers Company, Inc.Inventor: Hans Dressler
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Patent number: 4598160Abstract: A catalytic synthesis of chromans in racemic or optically active forms, including intermediates thereto; the synthesis employs an asymmetric palladium (II) catalyzed oxidative cyclization of a 2-homoallylphenol and provides intermediates useful in making chromans, especially vitamin E in racemic or optically active forms.Type: GrantFiled: March 11, 1985Date of Patent: July 1, 1986Assignee: Hoffmann-La Roche Inc.Inventor: Larry K. Truesdale
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Patent number: 4594460Abstract: 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: GrantFiled: March 19, 1985Date of Patent: June 10, 1986Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4590304Abstract: 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: GrantFiled: May 15, 1985Date of Patent: May 20, 1986Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: J. Shield Wallace, Fred E. Arnold
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Patent number: 4564476Abstract: Aryl fatty acid compounds of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, and Y are as defined herein are novel and useful in the treatment of allergic and inflammatory disorders.Type: GrantFiled: October 29, 1984Date of Patent: January 14, 1986Assignee: McNeilab, Inc.Inventor: Chih Y. Ho
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Patent number: 4551562Abstract: The nuclear hydroxylation of phenol with organic solutions of hydrogen peroxide in the presence of a catalyst is carried out in improved manner by employing both (1) a special, practically water free solution of hydrogen peroxide in an organic solvent which does not form an azeotrope with water or whose highest azeotrope with water, boil near or above the boiling point of hydrogen peroxide, and (2) employing as a catalyst XO.sub.2 where X is sulfur, selenium, or tellurium. Besides increasing the yield and the ability to carry out the reaction in a simpler manner when selenium dioxide is employed as a catalyst, there can also be controlled the ortho-para ratio, respectively, the ortho-ortho ratio of the product.Type: GrantFiled: March 13, 1984Date of Patent: November 5, 1985Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: 4540833Abstract: 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: GrantFiled: March 21, 1984Date of Patent: September 10, 1985Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: J. Shield Wallace, Fred E. Arnold
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Patent number: 4529556Abstract: The invention bis((aryl)vinyl)benzenes wherein the aryl and benzene moieties may be substituted, and the vinyl carbon alpha to the central benzene ring may be further substituted with an aliphatic group.Type: GrantFiled: August 19, 1983Date of Patent: July 16, 1985Assignee: The Dow Chemical CompanyInventor: Kenneth J. Bruza
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Patent number: 4510338Abstract: The invention relates to new resorcin derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 3 carbon atoms or alkoxy having from one to 3 carbon atoms.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.Type: GrantFiled: December 27, 1983Date of Patent: April 9, 1985Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
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4-Hydroxy-benzhydrols, process for their preparation and pharmaceutical compositions containing them
Patent number: 4508926Abstract: The invention relates to new 4-hydroxy-benzhydrols of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms, with the proviso that if R.sub.1 is hydrogen, R.sub.2 is other than hydrogen or a 3-trifluoromethyl group, or if R.sub.1 is a 2-methyl group, R.sub.2 is other than a 5-methyl group.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredients are also within the scope of the invention.Type: GrantFiled: December 27, 1983Date of Patent: April 2, 1985Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu -
Patent number: 4473713Abstract: At least one of the other functions comprising an aryl-aliphatic ether, e.g., veratrol, is catalytically hydrolyzed with water, e.g., to guaiacol, in the presence of a catalytically effective amount of a salt of a carboxylic acid.Type: GrantFiled: September 27, 1982Date of Patent: September 25, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4435601Abstract: Optionally aldehyde substituted polyphenols are prepared by oxidizing, with hydrogen peroxide, a hydroxybenzaldehyde bearing at least one aldehyde substituent ortho- and/or para- to the nuclear hydroxyl group, in an aqueous reaction medium and in the presence of an alkali or alkaline earth metal base, the process being characterized in that the pH of the reaction medium is continuously maintained at a value no greater than 7 throughout the course of the oxidation reaction.The subject process is well suited for the preparation of, e.g., hydroxy-p-vanillin from guaiacol, and the novel compound 2,4,6-triformylphenol.Type: GrantFiled: July 7, 1981Date of Patent: March 6, 1984Assignee: Rhone-Poulenc IndustriesInventors: Karel Formanek, Daniel Michelet, Dominique Petre
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Patent number: 4424382Abstract: Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic superacids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as Nafion-H) catalyzed cleavage-rearrangement reaction of meta-isopropylphenol hydroperoxide in the form of its protected ether or ester derivatives, including readily cleavable and reusable trimethylsilyl and trifluoromethanesulfonyl derivates. Part of the process is the preparation of needed meta-isopropylphenol in high purity free of other isomers by treating any mixture of isopropylphenol isomers in an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic superacid of one to eighteen carbon atoms and a Lewis acid fluoride or by alkylating (transalkylating) phenol with a propyl alkylating agent in the presence of the aforementioned superacid systems.Type: GrantFiled: June 1, 1982Date of Patent: January 3, 1984Assignee: PCUK Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4424381Abstract: A process is disclosed for separating closely-boiling dihydric phenol compounds by treating a mixture of dihydric phenols with a metal halide salt. The metal halide salt preferentially forms a complex with one of the dihydric phenols over other related dihydric phenols in the mixture. The preferentially-formed complex of one of the dihydric phenols may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one dihydric phenol. The process is particularly suitable for resolving a mixture comprising hydroquinone and catechol, or a mixture of hydroquinone and resorcinol, or a mixture of homocatechol and hydroquinone, or a mixture of catechol and resorcinol.Type: GrantFiled: April 26, 1982Date of Patent: January 3, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4398047Abstract: 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, wherein no tertiary carbon atom of R is directly bonded 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 a 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: February 23, 1982Date of Patent: August 9, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Yukihisa Takisawa, Shinichi Hasegawa
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Patent number: 4352944Abstract: The components of cashew nut shell liquid have such similar physical characteristics that their separation into relatively pure components has been difficult and has prevented use of the oil in many technological areas. The reaction of certain components with bases prior to distillation enables increased separation efficiency.Type: GrantFiled: January 8, 1981Date of Patent: October 5, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventors: John H. P. Tyman, Mahesh S. Patel, Anthony P. Manzara
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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: 4323714Abstract: Hydroxy-substituted aromatic compounds may be alkylated by treatment with an alkylating agent such as an olefin or an alcohol at a temperature in the range of from about 50.degree. to about 200.degree. C. and a pressure in the range of from about atmospheric to about 100 atmospheres in the presence of a fluoro-substituted resin. The resulting product will comprise both mono- and di-alkylated hydroxy-substituted aromatic compounds.Type: GrantFiled: November 20, 1980Date of Patent: April 6, 1982Assignee: UOP Inc.Inventors: Thomas P. Malloy, Dusan J. Engel
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Patent number: 4323715Abstract: Mono-tertiary butylhydroquinone may be prepared in a continuous method of operation by reacting hydroquinone with isobutylene in the presence of an acidic alumina catalyst. The alkylation is effected in a reaction medium which comprises an ether, and particularly a polyether such as the dimethyl ether of triethylene glycol.Type: GrantFiled: November 20, 1980Date of Patent: April 6, 1982Assignee: UOP Inc.Inventors: Dusan J. Engel, Thomas P. Malloy
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Patent number: 4323713Abstract: Hydroquinone is subjected to an alkylation reaction utilizing isobutylene or t-butyl alcohol as the alkylating agent to obtain t-butyl hydroquinone. The alkylation reaction is effected in the presence of an acidic catalyst such as phosphoric acid at temperatures ranging from about 75.degree. to about 200.degree. C. and a pressure in the range of from about atmospheric to about 100 atmospheres. By employing a mixture of a nonpolar hydrocarbon solvent such as xylene and an aliphatic ketone such as 2-heptanone, it is possible to obtain a greater ratio of mono-alkylated product to di-alkylated product.Type: GrantFiled: November 20, 1980Date of Patent: April 6, 1982Assignee: UOP Inc.Inventor: Dusan J. Engel