Preparing By Pyrolysis (e.g., By Cracking, Etc.) Patents (Class 568/806)
  • Patent number: 11319448
    Abstract: The present invention relates to a composition and a method of preparing the composition where the composition comprising functionalized lignin having a weight average molecular weight (Mw) of at least 1,000 g/mol and a green carrier liquid comprising depolymerized functional lignin, wherein the functionalized lignin is dissolved in the green carrier liquid and wherein the amount of depolymerized functionalized lignin compounds in the composition is higher than the amount of functionalized lignin.
    Type: Grant
    Filed: March 20, 2018
    Date of Patent: May 3, 2022
    Assignee: REN FUEL K2B AB
    Inventors: Christian Dahlstrand, Joseph Samec
  • Patent number: 9458247
    Abstract: Digestion of cellulosic biomass solids can be enhanced in the presence of a phenolic solvent. Methods for digesting cellulosic biomass solids can comprise providing cellulosic biomass solids containing up to about 50% water by mass in a digestion medium comprising about 50% or more of an organic solvent by volume; heating the cellulosic biomass solids and the digestion medium in a digestion unit in the presence of molecular hydrogen and a slurry catalyst capable of activating molecular hydrogen, thereby forming an alcoholic component derived from the cellulosic biomass solids and liberating lignin therefrom; wherein the digestion medium and the water form a biphasic mixture in which the alcoholic component, slurry catalyst, and lignin are contained; removing at least a portion of the biphasic mixture from the digestion unit; converting at least a portion of the lignin into a phenolic solvent; and returning the phenolic solvent to the digestion unit.
    Type: Grant
    Filed: March 13, 2014
    Date of Patent: October 4, 2016
    Assignee: Shell Oil Company
    Inventors: Joseph Broun Powell, Edward James Denton, Glenn Charles Komplin
  • Patent number: 9035107
    Abstract: In a process for the dehydrogenation of dehydrogenatable hydrocarbons, a feed comprising dehydrogenatable hydrocarbons is contacted with a catalyst comprising a support and a dehydrogenation component under dehydrogenation conditions effective to convert at least a portion of the dehydrogenatable hydrocarbons in the feed. The catalyst is produced by a method comprising treating the support with a liquid composition comprising the dehydrogenation component or a precursor thereof and at least one organic dispersant selected from an amino alcohol and an amino acid.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: May 19, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Stuart L. Soled, Edward A. Lemon, Joseph E. Baumgartner, Sabato Miseo, George H. Gamble
  • Patent number: 9029611
    Abstract: In a process for the dehydrogenation of cyclohexanone to produce phenol, a feed comprising cyclohexanone is contacted with a dehydrogenation catalyst under dehydrogenation conditions comprising a temperature of less than 400° C. and a pressure of less than 690 kPa, gauge, such 0.1 to 50 wt % of the cyclohexanone in said feed is converted to phenol and the dehydrogenation product contains less than 100 ppm by weight of alkylbenzenes.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: May 12, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Jihad M. Dakka, Christopher L. Becker, Keith H. Kuechler, Francisco M. Benitez, Charles M. Smith, Hari Nair
  • Publication number: 20140107306
    Abstract: In this invention, a portion of the products from a pyrolysis reactor are reacted in a process to form one or more chemical intermediates.
    Type: Application
    Filed: October 17, 2013
    Publication date: April 17, 2014
    Inventors: Terry Mazanec, Eugene Schmelzer, Fred Pesa, Dennis McCullough, Ruozhi Song, Yu-Ting Cheng
  • Publication number: 20120029243
    Abstract: The present invention relates to a composition (“composite”) comprising lignin and at least one catalyst dispersed in the composition. The invention further provides a process for producing such a catalyst- and lignin-comprising composition and its use for preparing an aromatics composition.
    Type: Application
    Filed: July 28, 2011
    Publication date: February 2, 2012
    Applicant: BASF SE
    Inventors: Emmanouil PANTOUFLAS, Roman Prochazka, Stephan Schunk
  • Publication number: 20080132735
    Abstract: A process is described for the preparation of phenol by the hydrodeoxygenation of polyhydroxylated benzene derivatives or by the selective hydroxylation of benzene under depletive conditions, characterized in that the above-mentioned reactions are carried out in the presence of a catalyst based on multi component metal oxides comprising at least one metal selected from the groups VB, VIB, VIII, IB, IIB, IVA, VA.
    Type: Application
    Filed: January 10, 2006
    Publication date: June 5, 2008
    Applicant: POLIMERI EUROPA S.p.A.
    Inventors: Leonardo Dalloro, Alberto Cesana, Roberto Buzzoni, Fausto Genoni, Guido Spano, Franco Rivetti
  • Patent number: 7161048
    Abstract: Methanol is produced from bacterially oxidized waste methane by reaction with Pd+2, Cu+2, air, and molten phthalic anhydride in an entrained oxidizer generating half ester of methyl phthalate which is reaction distilled to produce methanol and recycle phthalic anhydride containing the Pd+2, Cu+2 phthalate catalyst.
    Type: Grant
    Filed: May 11, 2006
    Date of Patent: January 9, 2007
    Assignee: Rinnovi, L.L.C.
    Inventors: Carol Knox, legal representative, Walter R. Knox, deceased
  • Patent number: 6765117
    Abstract: An improved method is described for making 9-deoxy-PGF1-type compounds. In contrast to the prior art, the method is stereoselective and requires fewer steps than the known methods for making these compounds. The invention also relates to novel intermediates prepared during the synthesis of the 9-deoxy-PGF1-type compounds.
    Type: Grant
    Filed: July 1, 2002
    Date of Patent: July 20, 2004
    Assignee: United Therapeutic Corporation
    Inventors: Robert M. Moriarty, Raju Penmasta, Liang Guo, Munagala S. Rao, James P. Staszewski
  • Patent number: 6646097
    Abstract: A method for purifying 1,1-bis(4′-hydroxy-3′-methylphenyl)cyclohexane comprises dissolving said 1,1-bis(4′-hydroxy-3′-methylphenyl)cyclohexane in a first solvent consisting essentially of an alcohol to form a first solution; filtering said first solution; adding a second solvent consisting essentially of water to the filtered first solution to form a second solution, wherein said second solution comprises about 40 parts to about 95 parts of the first solvent per 100 parts of the combined weight of the first and second solvents; crystallizing said 1,1-bis(4′-hydroxy-3′-methylphenyl) cyclohexane from said second solution to form a first crystalline product; dissolving said first crystalline product in a third solvent to form a third solution, wherein the third solvent comprises an aromatic compound; and crystallizing said 1,1-bis(4′-hydroxy-3′-methylphenyl)cyclohexane from said third solution to produce a second crystalline product.
    Type: Grant
    Filed: October 31, 2002
    Date of Patent: November 11, 2003
    Assignee: General Electric Company
    Inventors: Ashok Shyadligeri, Gary C. Davis, Debjani Kapila, Ramesh Krishnamurti, A. S. Radhakrishna, Veeraraghavan Srinivasan
  • Patent number: 6459004
    Abstract: A cleavage method of bisphenols capable of yielding a product containing high-purity isopropenylphenol and phenol is disclosed, including (1) a cleavage step of supplying the mixture containing bisphenols together with chroman derivatives and flavan derivatives formed as by-products in the production process of bisphenols to a cleaving vessel and carrying out a cleavage reaction in the presence of a basic or acidic catalyst at a temperature of from 150 to 260° C. under a reduced pressure condition of not higher than 300 mmHg, (2) a distillation step of supplying the cleavage step product formed in the cleavage step in a vapor state to a distillation column and distilling at a temperature of from 130 to 200° C. under a reduced pressure condition of not higher than 300 mmHg, and (3) a reflux step of condensing the distillate from the distillation step, refluxing a part thereof to the distillation step at a reflux ratio of from 0.01 to 3, and discharging out the residue from the system.
    Type: Grant
    Filed: February 23, 2001
    Date of Patent: October 1, 2002
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Yuzo Ono, Kouichirou Terada, Kiyoshi Mizuma, Mikio Shibasaki
  • Patent number: 6399838
    Abstract: A process for preparing 2,6-dimethylphenol from 2,4,6-trimethylphenol is provided. The process includes two steps: (1) selective oxidation of 2,4,6-trimethylphenol to 3,5-dimethyl-4-hydroxybenzaldehyde and (2) deformylation of the resulting benzaldehyde to 2,6-dimethylphenol. In step (1), the 2,4,6-trimethylphenol is reacted with oxygen-containing gases at temperatures of 20 to 200° C. in the presence of an iron-containing catalyst, which has higher 3,5-dimethyl-4-hydroxybenzaldehyde selectivity than the known copper-based catalysts. In step (2), a copper-containing catalyst is used to replace the customarily used precious metal catalysts for the effective deformylation of the 3,5-dimethyl-4-hydroxybenzaldehyde to 2,6-dimethylphenol.
    Type: Grant
    Filed: February 2, 2001
    Date of Patent: June 4, 2002
    Assignee: National Science Council
    Inventors: Kuo-Tseng Li, Pang Yih Liu
  • Patent number: 6303835
    Abstract: Phenol and isopropenylphenol are recovered from BPA tars by sparging the fluidized BPA tar while heating in the presence of a basic catalyst. Sparging dramatically increases the efficiency of phenol and isopropenylphenol recovery. Recovered isopropenylphenol may be converted to bisphenol A in the distillate by reaction with phenol and an acidic catalyst.
    Type: Grant
    Filed: September 11, 2000
    Date of Patent: October 16, 2001
    Assignee: General Electric Company
    Inventors: Sheldon Jay Shafer, Eric James Pressman, Julia Lam Lee
  • Patent number: 6291723
    Abstract: A catalyst composition comprising trifluoromethanesulfonic acid (also referred to as triflic acid) and a sufficient quantity of a substance (also referred to as a retarder) to decrease but not eliminate the catalytic activity of the acid is disclosed. Also disclosed, is a method and composition for condensing a hydroxyaryl with a diene by use of the catalyst composition. The method is capable of producing condensates having: a mole ratio of 1 mole of the diene to one mole of the hydroxyaryl; one mole of diene to two moles of the hydroxyaryl as well as higher molecular weight products such as resins by changes in temperature, time of reaction, type and quantity of retarder and other variables.
    Type: Grant
    Filed: September 2, 1999
    Date of Patent: September 18, 2001
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • Patent number: 6187964
    Abstract: A method of producing a phenol compound comprising a step of oxidizing an aromatic aldehyde to an aryl formate and an aromatic carboxylic acid with an oxygen-containing gas, and a step of decomposing the aryl formate to the phenol compound. To facilitate the separation of the aryl formate and the unreacted aromatic aldehyde, a mixture of the aryl formate and the unreacted aromatic aldehyde is recycled to the oxidation process to concentrate the aryl formate in the oxidation mixture. Alternatively, the oxidation process is carried out in an organic solvent having substantially no ability of dissolving water to increase the conversion of the aromatic aldehyde and the selectivity of the aryl formate, thereby producing the aryl formate in a high yield.
    Type: Grant
    Filed: July 14, 1999
    Date of Patent: February 13, 2001
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuo Tanaka, Yukio Sakai, Yasuhiro Shoji, Takafumi Yoshimura, Masatoshi Yoshimura
  • Patent number: 5300704
    Abstract: A process of using fast pyrolysis in a carrier gas to convert a plastic waste feedstream having a mixed polymeric composition in a manner such that pyrolysis of a given polymer to its high value monomeric constituent occurs prior to pyrolysis of other plastic components therein comprising: selecting a first temperature program range to cause pyrolysis of said given polymer to its high value monomeric constituent prior to a temperature range that causes pyrolysis of other plastic components; selecting a catalyst and support for treating said feed streams with said catalyst to effect acid or base catalyzed reaction pathways to maximize yield or enhance separation of said high value monomeric constituent in said temperature program range; differentially heating said feed stream at a heat rate within the first temperature program range to provide differential pyrolysis for selective recovery of optimum quantities of the high value monomeric constituent prior to pyrolysis of other plastic components; separating th
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: April 5, 1994
    Assignee: Midwest Research Institute
    Inventors: Robert J. Evans, Helena L. Chum
  • Patent number: 5260461
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, an aqueous solution, a base, a ferricyanide salt and an osmium-containing compound are combined. The chiral ligand is an alkaloid or alkaloid derivative linked to an organic substituent of at least 300 daltons molecular weight through a planar aromatic spacer group. The organic substituent can be another alkaloid or alkaloid derivative. With the described chiral ligands, asymmetric dihydroxylation of olefins with high yields and enantiomeric excesses are achieved.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: November 9, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Jens Hartung, K. Barry Sharpless
  • Patent number: 5198591
    Abstract: The invention relates to a process for obtaining a high purity bisphenol from a post-reaction mixture resulting from the step of synthesis of phenol and acetone in the presence of a strong acid cation exhanger catalyst, by the way of crystallation and separation by distillation followed by recovery of bisphenol-A from the step of thermal catalytic decomposition of by product of the principal process technology in a multistage process.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: March 30, 1993
    Assignees: Instytut Ciezkiej Syntezy Organicznej "Blachownia", Zaklady Chemiczne "Blachownia", ABB Lummus Crest Inc.
    Inventors: Maciej Kiedik, Jozef Kolt, Jerzy Marszycki, Eugeniusz Zajac, Teodor Bek, Zbigniew Swiderski, Anna Rzodeczko, Jerzy Mroz, Janina Olkowska
  • Patent number: 5136111
    Abstract: A process of using fast pyrolysis in a carrier gas to convert a waste phenolic resin containing feedstreams in a manner such that pyrolysis of said resins and a given high value monomeric constituent occurs prior to pyrolyses of the resins in other monomeric components therein comprising: selecting a first temperature program range to cause pyrolysis of said resin and a given high value monomeric constituent prior to a temperature range that causes pyrolysis of other monomeric components; selecting, if desired, a catalyst and a support and treating said feedstreams with said catalyst to effect acid or basic catalyzed reaction pathways to maximize yield or enhance separation of said high value monomeric constituent in said first temperature program range to utilize reactive gases such as oxygen and steam in the pyrolysis process to drive the production of specific products; differentially heating said feedstreams at a heat rate within the first temperature program range to provide differential pyrolysis for se
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: August 4, 1992
    Assignee: MRI Ventures, Inc.
    Inventors: Helena L. Chum, Robert J. Evans
  • Patent number: 4960958
    Abstract: The catalysts for use in pyrolytic decomposition of the phenol distillation residue in accordance with the present invention are used in pyrolytically decomposing a distillation residue resulting from the separation by distillation of cumene, phenol and acetone from a reaction mixture obtained by oxidizing cumene with molecular oxygen followed by acid cleavage, and the present catalysts are characterized by comprising oxygen containing metallic compounds having a particle diameter of 0.002-100 .mu.m.Furthermore, the processes for recovering useful substances from a phenol distillation residue containing the same in accordance with the present invention are characterized by allowing said phenol distillation residue to undergo pyrolytic reaction at a temperature of 200.degree.-350.degree. C., preferably 250.degree.-300.degree. C., in the presence of the above-mentioned oxygen containing metallic compound catalysts having a particle diameter of 0.002-100 .mu.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: October 2, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tetsuo Imamura, Tatsuo Shirahata, Kichiro Shoji
  • Patent number: 4900873
    Abstract: Phenols such as cresol, phenol and xylenol etc. are obtained by thermal decomposition of a lignin-containing material in a state of a mixture of the lignin-containing material and a double ring aromatic hydrocarbon solvent.Spent liquid of a solvolysis pulping process can be used as the lignin-containing raw material in the present invention for manufacturing phenols, and the phenols obtained can be utilized as the solvent in the solvolysis process resulting in cost reduction in the pulp production process by self-supplying the necessary solvent in the solvolysis process.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: February 13, 1990
    Assignees: JGC Corporation, Japan Pulp & Paper Research Institute, Inc.
    Inventors: Gohki Kakemoto, Hiroshi Sagara, Noriyuki Suzuki, Shogo Kachi
  • Patent number: 4873376
    Abstract: The invention relates to a process for the production of monomeric alkenylphenols from dihydroxydiphenylalkanes by thermal cleavage in certain solvents.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: October 10, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Dujardin, Wolfgang Ebert
  • Patent number: 4754081
    Abstract: Alkylenebisphenols and alkyltrisphenols are dearylated under mild conditions of temperature and pressure in the absence of HF to obtain alkyl and/or alkenyl substitute or phenols and other related polymer products.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: June 28, 1988
    Assignee: Hoechst Celanese Corporation
    Inventor: Graham N. Mott
  • Patent number: 4717777
    Abstract: A process for the preparation of alpha-alkenyl aromatic compounds, such as p-isopropenyl phenol, via the cleavage of cleavable organic compounds, e.g. dihydroxydiaryl alkanes such as bisphenol A, wherein an improved alkaline catalyst is employed. The catalyst comprises a metal oxide support component modified by an alkali metal hydroxide.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: January 5, 1988
    Assignee: The Dow Chemical Company
    Inventors: Juan M. Garces, John W. Robinson
  • Patent number: 4695659
    Abstract: A method is disclosed for the dealkylation of alkylaryl ethers by reaction with aluminum triodide under reflux. The reaction is carried out in the presence of a catalytic amount of a quaternary ammonium iodide in a substantially non-aqueous organic solvent. The reaction product is then hydrolyzed with water. The quaternary ammonium iodide can be of the formula R.sub.4 N.sup.+ I.sup.-, wherein R is alkyl, and the solvent is preferably benzene or cyclohexane.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: September 22, 1987
    Assignee: Chemical Dynamics Development AB
    Inventor: Sven-Goran B. Andersson
  • Patent number: 4657890
    Abstract: An improved alkaline catalyst which is especially useful in the preparation of alpha-alkenyl aromatic compounds, such as p-isopropenylphenol, via the cleavage of cleavable organic compounds, e.g., dihydroxydiaryl alkanes such as bisphenol A.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: April 14, 1987
    Assignee: The Dow Chemical Company
    Inventors: Juan M. Garces, John W. Robinson
  • Patent number: 4605789
    Abstract: A new process for preparing spirobiindanols, comprising refluxing the corresponding alkylaryl bisphenyl derivative in the presence of a dry heterogeneous acid catalyst in toluene, is disclosed.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: August 12, 1986
    Assignee: The Dow Chemical Company
    Inventors: H. Craig Silvis, Ted A. Morgan
  • Patent number: 4533769
    Abstract: A method is provided for making 3,5-dimethylphenol from isophorone by catalytic demethanation using as a catalyst, the calcination residue of a mixture of magnesium carbonate and/or magnesium hydroxide and a manganese compound.
    Type: Grant
    Filed: May 24, 1984
    Date of Patent: August 6, 1985
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4476330
    Abstract: Conversion, e.g. dehydration of aliphatic organic oxygenates having up to about 6 carbon atoms by contact with a crystalline aluminosilicate zeolite, preferably ZSM-5, having a silica to alumina ratio substantially greater than 10, at a temperature of about 70.degree. to 1400.degree. F., depending upon the exact nature of the reactant and product.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: October 9, 1984
    Assignee: Mobil Oil Corporation
    Inventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
  • Patent number: 4453025
    Abstract: Isophorone is converted to 3,5-xylenol in the vapor phase in the presence of a heterogeneous catalyst comprising a particular combination of multiple rare earth metals on an alumina support or one or more rare earth metals in combination with one or more transition metals and/or one or more alkali or alkaline earth metals. Particularly good results are obtained with a catalyst comprising a naturally-occurring mixture of rare earth metals known as didymium in combination with potassium and cobalt promoters.
    Type: Grant
    Filed: November 23, 1982
    Date of Patent: June 5, 1984
    Assignee: Shell Oil Company
    Inventors: Antonius J. C. Van Seters, Freddy Wattimena
  • Patent number: 4420644
    Abstract: A lignin-containing feed material in particulate form is mixed with a process-derived slurrying oil and fed into an ebullated catalyst bed hydrocracking reactor. Reaction conditions are maintained at 650.degree.-850.degree. F. temperature, 500-2500 psig hydrogen partial pressure and space velocity of 1.0-10 wt. lignin/hr./wt. catalyst. The reaction products are phase separated to recover hydrogen and slurrying oil, and the resulting liquid stream is passed to a thermal hydrodealkylation step. The reacted stream is fractionated to produce phenol and benzene products, along with a heavy alkylated material which is recycled to the hydrodealkylation step to increase the yield of phenol and benzene.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: December 13, 1983
    Assignee: Hydrocarbon Research, Inc.
    Inventors: Derk T. A. Huibers, Hugh J. Parkhurst, Jr.
  • Patent number: 4381413
    Abstract: A process for converting anisoles to ortho-methylated phenolic products in high selectivity is disclosed. The process comprises passing methoxybenzene, o-methylmethoxybenzene, 2,6-dimethylmethoxybenzene, or mixtures thereof, over gamma-alumina in the presence of an effective amount of water at a temperature in the range of about 225.degree. to about 295.degree. C.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: April 26, 1983
    Assignee: Conoco Inc.
    Inventor: John R. Dodd
  • Patent number: 4375566
    Abstract: A process for producing selectively o-alkylated phenols wherein an anisole having at least one ortho positioned hydrogen atom is contacted with a mixed oxide catalyst in the vapor phase.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: March 1, 1983
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Motoo Kawamata, Kazushi Ohshima, Mitsuo Onofusa, Akihide Kudoh, Makoto Kotani, Takeshi Tsuda
  • Patent number: 4351966
    Abstract: Bisphenol-A waste stream derived from the reaction of phenol and acetone in the presence of an acidic condensing agent can be treated with a molecular sieve to obtain good yields of phenol present in the effluent stream either in isolated form or as part of the compounds present in the waste stream.
    Type: Grant
    Filed: June 8, 1971
    Date of Patent: September 28, 1982
    Assignee: General Electric Company
    Inventor: John W. Flock
  • Patent number: 4283567
    Abstract: In a method for recovering resorcinol by thermally cracking high-boiling by-products formed by the acid-cleavage of m-diisopropylbenzene dihydroperoxide in the presence of at least one ammonium compound selected from the group consisting of ammonium sulfate and ammonium bisulfate at a temperature of about 170.degree. C. to about 350.degree. C. under reduced pressure, the improvement wherein said thermal cracking is carried out at a pressure of less than 50 mmHg gauge in the absence of any inert gas supplied.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: August 11, 1981
    Assignee: Mitsui Petrochemical Industries Ltd.
    Inventors: Hirohiko Nambu, Hiroaki Nakagawa, Masayasu Isibasi
  • Patent number: 4258221
    Abstract: Alkylenebisphenols are converted or cleaved to phenols and alkyl- and/or alkenyl-substituted phenols in good yields by contacting with hydrogen in the presence of a nickel oxide/manganese oxide/metal oxide supported catalyst. In a specific embodiment, bisphenol A is converted to isopropylphenol at high selectivity and high conversion by contacting with hydrogen in the presence of a nickel oxide/manganese oxide/magnesium oxide catalyst.
    Type: Grant
    Filed: April 11, 1979
    Date of Patent: March 24, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Ronald D. Knudsen, Geir Bjornson
  • Patent number: 4245128
    Abstract: A novel process for producing alkenyl phenols, which comprises continuously feeding a dihydroxydiphenyl alkane such as 2,2-(4,4'-dihydroxydiphenyl)propane, 2,2-(4,4'-dihydroxy-3,3'-dimethyldiphenyl)propane, 2,2-(4,4'-dihydroxydiphenyl)butane, 2,2-(4,4'-dihydroxydiphenyl)-4-methylpentane, 1,1,1-(4,4'-dihydroxytriphenyl)ethane and 1,1-(4,4'-dihydroxydiphenyl)cyclohexane into a high-boiling inert organic reaction medium such as an alkylnaphthalene containing a basic catalyst and heated at 150.degree. to 250.degree. C. under 10 to 100 mmHg while maintaining the concentration of the dihydroxydiphenyl alkane in the reaction medium at not more than 30% by weight, thereby cleaving it in the reaction medium; and continuously distilling off the cleavage product out of the reaction system and recovering it. This process can afford the corresponding highly pure alkenyl phenol as a monomer and/or its polymer almost quantitatively.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: January 13, 1981
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Nobukatu Kato, Tsutomu Takase, Yoshio Morimoto, Teruo Yuasa, Minoru Hattori
  • Patent number: 4242528
    Abstract: A novel process for producing isopropenyl phenol such as p-isopropenyl phenol which comprises continuously feeding oligomers of isopropenyl phenol having a degree of polymerization of 2 to 5 into a high-boiling inert organic reaction medium such as an alkylnaphthalene heated at 150.degree. to 250.degree. C. under a pressure of 10 to 100 mmHg while maintaining the concentration of the oligomers in the reaction medium at not more than 30% by weight, thereby thermally decomposing the oligomers in the reaction medium; and continuously distilling off the resulting isopropenyl phenol out of the reaction system and recovering it. The process almost quantitatively gives isopropenyl phenol having reduced contents of impurities.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: December 30, 1980
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobukatu Kato, Tsutomu Takase, Yoshio Morimoto, Teruo Yuasa, Minoru Hattori
  • Patent number: 4230895
    Abstract: The present invention provides a process, for the thermal dealkylation of alkylated phenols, which process comprises reacting a feed solution containing alkylated phenols and gaseous hydrogen in the presence of water vapor, the reaction being carried out at total pressure of 400 to 800 psig, temperature ranging from about 1000 .degree. to about 1500.degree. F., and the weight percent water vapor in the reaction being from about 10 to about 40 Wt % of the alkylated phenol feedstock.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: October 28, 1980
    Assignee: Hydrocarbon Research, Inc.
    Inventor: Francis P. Daly
  • Patent number: 4227012
    Abstract: Oxidation of methyl benzenes with air or oxygen to form a phenolic acetate and formaldehyde or methylene diacetate may be carried out in the presence of acetic acid, phosphorus pentoxide, benzaldehyde and an acid catalyst. The resulting acetates may then be pyrolyzed to yield phenolic compounds and formaldehyde, respectively.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: October 7, 1980
    Assignee: Suntech, Inc.
    Inventors: George Suld, James E. Lyons, Robert W. Shinn
  • Patent number: 4225728
    Abstract: Equimolar amounts of vinyl acetate and phenol may be prepared by oxidation of ethyl benzene. The catalytic oxidation, of ethyl benzene, when carried out in the presence of acetic anhydride, forms phenyl acetate and ethylidene diacetate. Pyrolysis of these two intermediates yields vinyl acetate and phenol.In a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for this oxidation reaction.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: September 30, 1980
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: 4131749
    Abstract: The essence of the invention consists in heating the dian waste in the presence of sodium hypophosphite as a catalyst in amount of 0.01 - 0.5% by weight at a temperature of 150 to 250.degree. C and under reduced pressure in the range of 5 to 50 mm Hg. As a result a destillate is obtained containing as main components phenol, o- and p-isopropenyl-phenol and their dimers at yield of about 40-74% by weight calculated in relation to the initial amount of dian waste. The distillate obtained was made up with fresh phenol or with phenol and acetone and brought into contact with strongly acid cation exchanger, such as Wofatit KPS, Zerolit 225, Wofatit OK-80, in consequence the o- and p-isopropenylphenol and their dimers reacted with phenol to obtain the dian, the latter being then separated by known methods.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: December 26, 1978
    Assignee: Instytut Ciezkiej Syntezy Organicznej "Blachownia"
    Inventors: Maciej Kiedik, Edward Grzywa, Jozef Kolt, Kazimierz Terelak, Jerzy Czyz, Anna Niezgoda