Preparing By Catalytic Alkylation Patents (Class 568/785)
-
Patent number: 9434668Abstract: The present invention relates to an improved process for the selective alkylation of phenols by reacting it with methyl tertiary butyl ether (MTBE) using polymer supported carbon composite acidic catalyst under mild to moderate conditions at atmospheric pressure. The process is economically viable since the catalyst regenerated after the initial reaction on further use gives the para tertiary butyl phenol (PTBP) in high yield.Type: GrantFiled: December 1, 2015Date of Patent: September 6, 2016Assignee: Council of Scientific and Industrial ResearchInventors: Praveen Kumar Khatri, Suman Lata Jain, Indrajit Kumar Ghosh
-
Patent number: 9012697Abstract: A process is proposed for preparing hydroxyaromatics by heterogeneous catalytic reaction of hydroxyaromatics with C1-C4-alkanols in a microreactor (10), comprising the steps of: a) introducing the hydroxyaromatic and at least one compound selected from the group consisting of C1-C4-alkanols as reactants into at least one inlet orifice (22) of the microreactor (10) comprising at least one microreactor unit (18), b) passing the reactants through at least one microreactor unit (18) of the microreactor (10), said unit comprising a multitude of microchannels (28), said microchannels (28) having a lateral extent of less than 1 mm, and a heterogeneous catalyst being incorporated in the microchannels (28) for conversion of the reactants, c) passing the hydroxyaromatics prepared out through at least one outlet orifice (24) of the microreactor (10).Type: GrantFiled: March 7, 2012Date of Patent: April 21, 2015Assignee: Elantas GmbHInventors: Oliver Bleifuβ, Simon Rost, Klaus-Wilhelm Lienert, Hans-Ulrich Moritz
-
Patent number: 8207380Abstract: An alkylated hydroxyaromatic compound prepared by reacting at least one hydroxyaromatic compound with a branched olefinic oligomer having from about 20 to about 80 carbon atoms in the presence of a acid catalyst. The alkylated hydroxyaromatic compound has been determined to be substantially free of endocrine disruptive chemicals when the effects were quantified on pubertal development and thyroid function in the intact juvenile female rat.Type: GrantFiled: April 27, 2007Date of Patent: June 26, 2012Assignee: Chevron Oronite LLCInventors: Curt B. Campbell, James J. Harrison
-
Patent number: 7705191Abstract: Substituted hydrofluoroalkylphenol compounds and methods of using the compounds, e.g., for anesthetizing a subject, are disclosed.Type: GrantFiled: July 13, 2007Date of Patent: April 27, 2010Assignee: University of Iowa Research FoundationInventor: Max T. Baker
-
Patent number: 7692047Abstract: The present invention relates to an improved process for the selective alkylation of phenols using heteropolyacid catalyst supported onto zirconia under mild conditions. The process is economically viable since the catalyst regenerated after the initial reaction on further use gives the product in high yield.Type: GrantFiled: September 26, 2007Date of Patent: April 6, 2010Assignee: Secretary, Department of Science & TechnologyInventors: Anjali Uday Patel, Nikunj Bhagwatiprasad Bhatt
-
Patent number: 7288683Abstract: An alkylation method comprises reacting a hydroxy aromatic compound with an alkyl alcohol in the presence of an alkylation catalyst comprising a metal oxide wherein the alkylation catalyst, has a surface area to volume ratio of about 950 to about 4,000 m2/m3, an aspect ratio of about 0.7 to about 1.0 or a combination of the foregoing.Type: GrantFiled: June 16, 2006Date of Patent: October 30, 2007Assignee: General Electric CompanyInventors: Hugo G. E. Ingelbrecht, David Parrillo, Mukund Parthasarathy, Gert-Jan Schoenmakers, Geuch Zijlma
-
Patent number: 6670513Abstract: An alkylated hydroxyl-containing aromatic compound is produced by isomerizing a normal alpha-olefin having from about 16 to about 30 carbon atoms in the presence of a first solid, acidic catalyst capable of inducing both olefin isomerization and skeletal isomerization to produce a mixture of isomerized olefin, then alkylating an hydroxyl-containing aromatic compound with the mixture of isomerized olefins in the presence of a second solid, acidic catalyst. The first solid, acidic catalyst can be SM-3, MAPO-11, SAPO-11, SSZ-32, ZSM-23, MAPO-39, SAPO-39, ZSM-22, SSZ-20, ZSM-35, SUZ-4, NU-23, NU-87, natural ferrierite or synthetic ferrierite. The second solid, acidic catalyst can be a sulfonic acid anionic ion exchange resin catalyst or an acidic clay.Type: GrantFiled: December 3, 1999Date of Patent: December 30, 2003Assignees: Chevron Oronite Company, LLC, Chevron Oronite S.A.Inventors: Curtis Bay Campbell, Jean Louis Le Coënt
-
Patent number: 6617476Abstract: A process for producing an aromatic ring alkylated phenols, wherein said process comprises reacting phenols represented by the general formula (1): wherein, each of R1, R2, R3, R4 and R5 independently represents a hydrogen atom, or a linear or branched alkyl group having 1 to 10 carbon atoms; with monohydric or dihydric alcohol in the presence of a hydroxide of a metal, an alkoxide of a metal, or a hydroxide of a metal and an alkoxide of a metal under a supercritical state of the alcohol.Type: GrantFiled: December 13, 2000Date of Patent: September 9, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Suzuki, Fumisato Goto, Kozo Tanaka
-
Patent number: 6232485Abstract: A process for the production of liquid meta-rich triaryl phosphate esters having low triphenyl phosphate content and low viscosity comprises (a) an alkylation stage wherein a phenol is reacted with an olefin having 2 to 12 carbon atoms in the presence of a strong acid catalyst to give a reaction product comprising a mixture of meta and para alkylated phenols; and (b) a transalkylation stage wherein the mixture of alkylated phenols from the alkylation stage is heated in the presence of a strong acid catalyst to increase the meta isomer content of the mixture to at least 25% whilst maintaining a phenol level below 22%; and (c) a phosphorylation stage wherein the mixture of alkylated phenols from the transalkylation stage is reacted with a phosphorylating agent; and wherein the strong acid catalyst used in stages (a) and (b) is a Bronsted acid having an acid strength of less than zero. Preferred catalysts are activated clays such as bentonite, montmorillonite or Fullers Earth clay.Type: GrantFiled: November 26, 1999Date of Patent: May 15, 2001Assignee: Great Lakes Chemical CorporationInventors: Tracy Anne Derbyshire, Hazel May Farrow, Jonathan Simon Hill
-
Patent number: 6049015Abstract: A method for C-alkylating a hydroxylated aromatic compound having at least one hydrogen atom in the ortho or para position relative to the hydroxyl grouping, wherein the aromatic compound is exposed to a proton acid and a compound causing the formation of a carbo-cation in the presence of the acid, and the reaction is performed in the presence of a solvent consisting of a water-alcohol pair.Type: GrantFiled: August 31, 1998Date of Patent: April 11, 2000Assignee: Rhodia ChimieInventors: Cecile Serrano, Michel Dury, Jean-Roger Desmurs, Paul Cruciani
-
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
-
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
-
Patent number: 5345002Abstract: The present invention is directed to oil-soluble lubricating oil additives comprising Mannich Base condensates of an alkyl substituted hydroxy aromatic compound with formaldehyde and an amine, wherein the alkyl-moiety of the aromatic compounds is derived from at least one ethylene alpha-olefin copolymer of 300 to 20,000 number average molecular weight, wherein at least about 30% of the polymer's chains contain terminal ethenylidene unsaturation. The Mannich Base condensates of this invention are useful as dispersants.Type: GrantFiled: October 9, 1992Date of Patent: September 6, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Won R. Song, Robert D. Lundberg, Antonio Gutierrez, Robert A. Kleist
-
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
-
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
-
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
-
Patent number: 5274174Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).Type: GrantFiled: June 10, 1993Date of Patent: December 28, 1993Assignee: Hoechst Celanese CorporationInventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
-
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
-
Patent number: 5087772Abstract: A method for preparing 4-hydroxystyrene is disclosed. The method comprises reacting 4-acetoxystyrene with a suitable alcohol in the presence of a catalytic amount of a suitable base.Type: GrantFiled: November 16, 1990Date of Patent: February 11, 1992Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, Lan Shen
-
Patent number: 4950810Abstract: A selective process for preparing a 2,4- or 3,6-di-substituted phenol compound which comprises reacting an olefin compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, halogen, alkyl, halogen substituted alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R.sup.2, R.sup.3 and R.sup.4 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl; with a phenol compound of the formula: ##STR2## wherein R.sup.5 is hydrogen, hydroxy, halogen, alkyl, halogen substituted-alkyl, alkoxy or --C(R.sup.6)(R.sup.7)CH(R.sup.8)(R.sup.9) (wherein R.sup.6 is hydrogen, halogen, alkyl, halogen substituted-alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R.sup.7, R.sup.8 and R.sup.9 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl), in the presence of a phosphorus compound and a carboxylic acid compound as catalysts.Type: GrantFiled: March 29, 1989Date of Patent: August 21, 1990Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Ryoichi Kinishi, Shuichi Wakamatsu, Tetsuji Ike
-
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
-
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
-
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
-
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
-
Patent number: 4540831Abstract: A process is disclosed for performing an exothermic reaction such as the etherification of isobutylene with methanol. The feed is charged to a vertical reaction zone containing a solid catalyst. Heat released by the exothermic reaction partially vaporizes the reactants, with the vapors traveling upward to a condensing zone. All of the condensable vapors entering the condensing zone are condensed and returned downward to the catalyst bed. A single effluent stream made up of the product, excess reactants and any unreactive compounds present in the feed streams is removed from the bottom of the reaction zone. This total reflux reaction zone allows temperature control within a catalyst bed without the use of indirect heat exchangers located within the reaction zone.Type: GrantFiled: May 17, 1984Date of Patent: September 10, 1985Assignee: UOP Inc.Inventor: Bruce A. Briggs
-
Patent number: 4461916Abstract: p-tert-octyl phenol is produced by reaction of phenol with diisobutene in the presence of an acidic ion exchanger and water, in a first stage, in a solid-bed reactor at temperatures of 110.degree.-140.degree. C. and under an excess pressure of up to 5 bar. The resultant dioctyl phenol formed as a by-product is alkylated in a second stage in a further solid-bed reactor with phenol in the presence of an acidic ion exchanger, and water at temperatures of 110.degree.-140.degree. C. and under an excess pressure of up to 5 bar to obtain additional p-tert-octyl phenol.Type: GrantFiled: December 29, 1982Date of Patent: July 24, 1984Assignee: Chemische Werke Huels A.G.Inventors: Helmut Alfs, Werner Boexkes, Erwin Vangermain
-
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
-
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
-
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
-
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
-
Patent number: 4092367Abstract: A process of preparing an alkylated phenol which is substantially monoalkylated and para oriented which comprises reacting phenol with a C.sub.4 -C.sub.9 olefin and wherein said olefin is utilized in about 5-10% stoichiometric excess. The broad reaction temperature utilized is about 60.degree.-105.degree. C and the time of reaction is at least 30 minutes. The catalyst utilized is anhydrous H.sub.3 PO.sub.4 which is used in a value of at least 8% based upon the weight of reactant phenol. The preferred products are p-t-amylphenol and p-t-butylphenol, and in the process of preparing these preferred phenols, the olefin may be reacted in 5-8% stoichiometric excess and the reaction temperature utilized may be 95.degree.-115.degree. C. An additional preferred product is p-nonylphenol derived from a branched propylene trimer.Type: GrantFiled: September 3, 1976Date of Patent: May 30, 1978Assignee: Nalco Chemical Co.Inventors: Billy W. Bridwell, Carl E. Johnson