Preparing By Dealkylation Patents (Class 568/805)
  • Patent number: 10351498
    Abstract: A method for producing hemp oil, comprising decarboxylation of CBDA in hemp oil; short-path evaporation of CBD from the decarboxylated hemp oil to produce CBD oil; selective THC to CBN conversion performed on the decarboxylated hemp oil.
    Type: Grant
    Filed: April 28, 2016
    Date of Patent: July 16, 2019
    Assignee: CV SCIENCES, INC.
    Inventors: Michael J. Mona, Joshua A. Hartsel, Greg Waterbury
  • Publication number: 20110313178
    Abstract: The present invention discloses a process for producing small molecular weight organic compounds from carbonaceous material comprising a step of contacting the carbonaceous material with carbon monoxide (CO) and steam in presence of a shift catalyst at a predetermined temperature and pressure.
    Type: Application
    Filed: July 31, 2008
    Publication date: December 22, 2011
    Applicant: NAGARJUNA ENERGY PRIVATE LIMITED
    Inventors: Manoj Kumar Sarkar, Dhurjati Prasad Chakrabarti, Dhruba Sarkar, Banibrata Pandey
  • Patent number: 7253324
    Abstract: Alkoxy aromatic compounds are conveniently dealkylated to the corresponding phenolic compounds by treatment with aluminum chloride/N,N-dimethyl aniline complex. Aromatic poly O-demethylation is a unique feature of this invention. This process is applicable to the manufacture of polyphenols such as Resveratrol, Oxyresveratrol, Gnetol.
    Type: Grant
    Filed: January 23, 2007
    Date of Patent: August 7, 2007
    Assignee: Sami Labs Limited
    Inventors: Muhammed Majeed, Samuel Manoharan Thomas, Kalyanam Nagabhushanam, Sivaprakash Kurumanghat Balakrishnan, Subbalakshmi Prakash
  • Patent number: 6794548
    Abstract: A method for producing 4,4′-biphenol, comprising the steps of: preparing serially arranged reaction bathes for two or more steps; and carrying out a debutylation reaction of 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol sequentially in the presence of an acid catalyst in a reaction solvent by supplying at least one kind of phenols selected from the group consisting of phenol, monoalkylphenols, dialkylphenols, and trialkylphenols, in a proportion of at least 0.5 mole part relative to one mole part of 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol, to each reaction bath as a solvent for addition, wherein the number of carbon atoms of alkyl groups in alkylphenols consisting of the monoalkylphenols, dialkylphenols, and trialkylphenols, is each independently in the range of 1 to 4, and wherein a solvent for addition to a reaction bath for the latter step has a smaller average number of alkyl groups than a solvent for addition to a reaction bath for the former step.
    Type: Grant
    Filed: October 14, 2003
    Date of Patent: September 21, 2004
    Assignee: Honschu Chemical Industry Co., Ltd.
    Inventors: Mikio Kawahara, Toyokazu Kitaura
  • Publication number: 20040010166
    Abstract: A new process for preparing a compound of the general formula ArOH (I) in which Ar represents an aryl or heteroaryl group substituted by at least one electron-donating group.
    Type: Application
    Filed: December 20, 2002
    Publication date: January 15, 2004
    Inventors: Kari Aasbo, Tom Granli, Harald Breivik
  • Patent number: 6639094
    Abstract: A process for producing &agr;-amino-dihalogenated methyl ketone derivatives by reacting an N-protected &agr;-amino acid ester with a dihalomethyl lithium is provided. This process is suitable for the production on an industrial scale and by this process, &agr;-amino-dihalogenated methyl ketone derivatives and &bgr;-amino-&agr;-hydroxycarboxylic acid derivatives can be obtained efficiently and economically advantageously.
    Type: Grant
    Filed: September 12, 1999
    Date of Patent: October 28, 2003
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tomoyuki Onishi, Takashi Nakano, Naoko Hirose, Takayoshi Torii, Masakazu Nakazawa, Kunisuke Izawa
  • Patent number: 6512149
    Abstract: By bringing a p-butylphenol compound or m-butylphenol compound in the gas phase into contact with a solid acid catalyst, i.e., a silica-alumina catalyst or alumina catalyst while heating, butyl groups are removed from the butylphenol compound and at the same time, highly purified isobutylene is recovered.
    Type: Grant
    Filed: April 13, 2001
    Date of Patent: January 28, 2003
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Mitsuhiro Higashi, Kenji Ekawa
  • 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: 5969196
    Abstract: For the preparation of 3,5-dimethylphenol by catalytic demethylation of isophorone in the gas phase in the presence of a metal or a metal alloy as catalyst, an isophorone-containing process stream is guided through reaction zones that contain said catalyst, whereby the reactivity of the catalyst varies in the reaction zones and the process stream between these reaction zones is thermostated in zones that do nor contain any catalyst, whereby the residual isophorone is greatly reduced, and the yield of 3,5-dimethylphenol is increased.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: October 19, 1999
    Assignee: Rutgers VFT AG
    Inventors: Wolfgang Bergins, Jorg Talbiersky
  • Patent number: 5463129
    Abstract: The present invention relates to a method of cleaving arylethers such as arylethers represented by the formula: ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, cycloalkyl, phenyl, substituted phenyl or CH.dbd.CH.sub.2 ; each A is independently NO.sub.2, hydroxy, halo, or methoxy; n is an integer from 0 to 5; and x is 1 or 2, comprising contacting the arylether with an amide hydrohalide salt under conditions sufficient to cleave the ether group(s) of the arylether and form a phenol or substituted phenol. The present invention also relates to a method of preparing 4,6-diaminoresorcinol, which is a monomer used for making polybenzoxazoles (PBO).
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: October 31, 1995
    Assignee: The Dow Chemical Company
    Inventors: Zenon Lysenko, Richard G. Pews
  • Patent number: 5324868
    Abstract: 4,4'-Biphenol is prepared through debutylation of 3,3', 5,5'-tetra-tert-butyl-4,4'-biphenol in an organic solvent in the presence of an acid catalyst wherein the debutylation is carried out continuously using at least two reactors aligned in series, with a high yield and high purity on an industrial level.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: June 28, 1994
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Masashi Inaba, Norioki Mine, Mamoru Mizutani
  • Patent number: 5171895
    Abstract: Purification of cresylic acid by guaiacol removal from lignite-based feed as well as other naturally occurring sources of cresylic acid is accomplished by catalytic demethylation in the presence of an alumina catalyst. In the process of this invention, de-pitched, dephenolated creyslic acid is vaporized and passed over a high surface area, alumina catalyst at temperature ranges of between 350.degree. C. to 400.degree. C. and at vapor flow rates measured as liquid hourly space velocity (LHSV), of about 1 hr..sup.-1 to demethylate the guaiacol.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: December 15, 1992
    Assignee: Merichem Company
    Inventor: James A. Brient
  • Patent number: 5099076
    Abstract: The present invention is directed to a method for the preparation of p,p'-biphenol by simplified processes achieved by batch or continuous operations which comprises using phenol and isobutylene as starting materials, allowing phenol to react with isobutylene in the presence of aluminum phenoxide, oxidizing the resulting reaction liquid in the presence of an alkaline catalyst, and debutylating the reaction liquid in the presence of a debutylation catalyst.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: March 24, 1992
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Katsunori Takahashi, Mikio Kawahara, Shunji Yago, Yoshiharu Ayabe
  • Patent number: 5097080
    Abstract: A process for preparing 4,4'-dihydroxybiphenyl is disclosed, which comprises debutylation of 3,3', 5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl in an organic solvent in the presence of an acid catalyst, wherein said debutylation is carried out in the presence of water and/or a lower alcohol. The desired product can be obtained at a high purity in a high yield.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: March 17, 1992
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Masashi Inaba, Norioki Mine, Mamoru Mizutani
  • Patent number: 5072055
    Abstract: The substituent X in the phenols of the formula: ##STR1## wherein R.sub.1 to R.sub.4 are hydrogen or unsubstituted or substituted alkyl, alkenyl or alkynyl, and X is secondary or tertiary alkyl of 3 to 9 carbon atoms, can be removed by heating said phenols in the presence of an alkali metal hydrogensulfate.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: December 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Hugo Illy, Ronald Salathe, Rudolf Schwabe
  • Patent number: 4950808
    Abstract: Reducing 3,3', 5,5'-tetra-t-butyldiphenoquinone with 2,6-di-t-butylphenol, in the melt, in the presence of a 4-dialkylaminopyridine, and then dealkylating the intermediate formed, in the melt, by adding a phosphorus-containing acid or its derivative provides 4,4'-dihydroxybiphenyl of high purity in high yield.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: August 21, 1990
    Assignee: Huels Aktiengesellschaft
    Inventors: Udo Kowalczik, Martin Bartmann, Juergen Finke
  • Patent number: 4891453
    Abstract: A process is disclosed which is capable of producing p,p'-biphenol of high purity by the dealkylation reaction of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl and which yet allows isobutene to be recovered in high yield. The process performs the dealkylation reaction of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl in the presence of an acid catalyst using as a solvent a saturated hydrocarbon having a boiling point of 190.degree. C. or above, an alicyclic hydrocarbon having a boiling point of 190.degree. C. or above, a hydrocarbon with an iodine value of no more than 1, sulfolane, or a mixture of these solvents. Also disclosed is a process for producing p,p'-biphenol from a mixture of 2,6-di-t-butyl-phenol and 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone or from a mixture of 2,6-di-t-butylphenol, 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone and 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: January 2, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Michio Tanaka, Yoshito Kurano, Katsuo Taniguchi, Masayasu Ishibashi
  • Patent number: 4847435
    Abstract: A meritorious, commercially successful process for the recovery of a high-purity m-ethylphenol from ethylphenol mixtures containing m- and p-ethylphenols as the major components is disclosed. As it is well known in the art, the ethylphenol mixtures containing m- and p-ethylphenols as the major components can easily be prepared by ethylation of phenol with ethylene or ethanol by a simple operation. Accordingly, a process for the recovery of high-purity m-ethylphenol from ethylphenol mixtures containing m- and p-ethylphenols as the major components can give great influences in the commercial production of high-purity m-ethylphenol. m-Ethylphenol is a useful intermediate for the production of pharmaceuticals and agricultural chemicals. The process comprises simply contacting an ethylphenol mixture containing m- and p-ethylphenols as the major components with a specific crystalline aluminosilicate catalyst under heating.
    Type: Grant
    Filed: June 13, 1988
    Date of Patent: July 11, 1989
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Keizo Kase, Tsutomu Idai, Kazumasa Ishii, Eiji Takahashi
  • 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: 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: 4667037
    Abstract: An improved process for the dealkylation of alkyl aryl ethers to aryl phenols is provided. In this process, an alkyl aryl ether, such as a methyl ether of an opioid, is contacted with an aqueous acid selected from HBr, HCl, or HI which contains at least one equivalent weight, based on the ether, of boric acid or an inorganic salt of a metal selected from Li, Na, K, Al, Mg, Ca, Mn and Ni. MgBr.sub.2 in aqueous HBr is preferred in dealkylating an N-substituted 14-hydroxydihydronorcodeine.
    Type: Grant
    Filed: June 6, 1985
    Date of Patent: May 19, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Walter M. Bryant, III
  • Patent number: 4605790
    Abstract: Phenol is prepared from mixed phenols derived from coal or biomass by separation of the mixed phenols, isomerization of m- and/or p-cresols to o-cresol, demethylation of o-cresol, dealkylation of xylenols and other alkyl phenols, recycling of products other than phenol, and, optionally, reducing phenol to cyclohexanone/cyclohexanol, followed by oxidation thereof to adipic acid.
    Type: Grant
    Filed: May 21, 1985
    Date of Patent: August 12, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Paul W. Wojtkowski
  • Patent number: 4560810
    Abstract: Alkylated hydroxyaromatic compounds, particularly alkylated phenols such as mesitol and 2,4-xylenol, are selectively ortho-dealkylated by contact at a temperature within the range of about 350.degree.-500.degree. C. with a catalyst comprising a combination of at least one chromium oxide and at least one of the oxides of zinc, iron, magnesium and manganese, with zinc and iron being preferred.
    Type: Grant
    Filed: November 14, 1984
    Date of Patent: December 24, 1985
    Assignee: General Electric Company
    Inventors: John J. Talley, Irene A. Evans, Michael D. Lewis
  • Patent number: 4533767
    Abstract: Selective catalytic steam dealkylation of ortho- and para-positions of alkylated phenols is accomplished by reacting ortho- and/or para-alkylated phenols with steam in the presence of a catalyst comprised of magnesium oxide, optionally manganese oxide and optionally an organic binder; said reaction may preferably takes place in the presence of an oxidizing atmosphere to extend catalyst life. High degrees of conversion are obtained without loss of the hydroxyl radical of the alkylated phenols.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: August 6, 1985
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4533768
    Abstract: Selective catalytic steam dealkylation of ortho- and para-positions of alkylated phenols is accomplished by reacting ortho- and/or para-alkylated phenols with steam in the presence of a catalyst comprised of zinc oxide, optionally manganese oxide and optionally an organic binder and preferably an oxidizing atmosphere. High degrees of conversion are obtained without loss of the hydroxyl group of the alkylated phenols.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: August 6, 1985
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4473713
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: September 25, 1984
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Serge Ratton
  • Patent number: 4431850
    Abstract: A process for thermal dealkylation of alkylated phenols feedstocks, which comprises reacting a feed mixture containing mono and poly-alkylated phenols and gaseous hydrogen at temperature ranging from about 900.degree. to about 1100.degree. F. at hydrogen partial pressure of 300 to 1600 psig, and space velocity of 0.2 to 3.0 volume feed/hr/volume of reactor to produce a phenol-containing product at increased selectivity and yield of phenol. For feedstream mixtures containing more than about 10 W % phenols, a prior distillation step is preferably used to remove the excessive phenol as product and thus avoid undesired dehydroxylation reactions in the hydrodealkylation step to which the feed phenol concentration is usually about 2-8 W %.
    Type: Grant
    Filed: November 9, 1981
    Date of Patent: February 14, 1984
    Assignee: HRI, Inc.
    Inventors: Derk T. A. Huibers, Cheng-Yih Jenq
  • Patent number: 4351968
    Abstract: Pyrogallol, and analogues thereof having an alkyl, carboxy or alkoxycarbonyl substituent in the benzene ring, and their salts, are prepared by oxidizing, preferably by hydrogen peroxide, the corresponding compounds in which 1 or 2 of the OH groups are replaced by --COR.sup.5 groups where R.sup.5 represents hydrogen, alkyl or phenylalkyl. The production of intermediates is also described and some of these are novel.
    Type: Grant
    Filed: September 12, 1980
    Date of Patent: September 28, 1982
    Assignee: FBC Limited
    Inventor: John F. Harris
  • Patent number: 4230896
    Abstract: This invention provides a method for the selective dealkylation of alkylated phenols, which method comprises reacting a feed solution comprising a mixture of alkylated phenols with steam in the presence of a catalyst comprising a hydrous carrier, at least one catalyst deactivation suppressor, and at least one promoter. A salt of an alkali metal may be added to the feed to enhance the selectivity of phenol in the product.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: October 28, 1980
    Assignee: Hydrocarbon Research, Inc.
    Inventor: Francis P. Daly
  • 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: 4228311
    Abstract: A method is described for the selective dealkylation of 4-tertiary-alkyl-2,5-xylenol while it is admixed with 6-tertiary-alkyl-2,4-xylenol by contacting the mixture of alkylated xylenols with a polymer-bound sulfonic acid catalyst at temperatures of 60.degree. C. or less and pressures of from about 0.5 to 5 atmospheres. The method is useful in separating 2,4-/2,5-xylenol mixtures.
    Type: Grant
    Filed: June 8, 1979
    Date of Patent: October 14, 1980
    Assignee: Conoco, Inc.
    Inventor: John R. Dodd
  • Patent number: 4205187
    Abstract: A process for preparing p,p'-biphenol is provided which comprises heating a 4,4'-bis(substituted phenol) at elevated temperatures below the decomposition temperature of p,p'-biphenol in the absence of a catalyst under an inert, non-reactive atmosphere for the length of time sufficient to obtain a reaction product containing a substantial amount of p,p'-biphenol while, preferably, removing the olefin by-product formed and then recovering the p,p'-biphenol product.
    Type: Grant
    Filed: January 2, 1979
    Date of Patent: May 27, 1980
    Assignee: Union Carbide Corporation
    Inventors: Jorge N. Cardenas, Walter T. Reichle
  • Patent number: 4191844
    Abstract: Hydrodealkylation of alkyl-substituted aromatic compounds by contacting with hydrogen in the presence of a catalyst of manganese oxide and a Group IIA metal oxide such as magnesium oxide, optionally promoted with a Group VIII hydrogenation metal such a nickel oxide and an alumina-containing isomerization component.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: March 4, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Geir Bjornson
  • Patent number: 4189613
    Abstract: Substituted aromatic compounds are hydrodealkylated in the presence of hydrogen and a low sodium content chromia-alumina catalyst under conditions of temperature and pressure such that a small amount of nonrecyclable dehydroxylated products such as benzene, toluene and xylenes are obtained.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: February 19, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Geir Bjornson
  • Patent number: 4152529
    Abstract: Halogenated alkyl substituted phenols may be dealkylated by treating a compound such as 5-t-butyl-2-fluorophenol with a diealkylation catalyst such as an acid acting compound at dealkylation conditions whereby the t-butyl substituent is removed and the resulting compound comprising 2-fluorophenol is recovered.
    Type: Grant
    Filed: November 16, 1977
    Date of Patent: May 1, 1979
    Assignee: UOP Inc.
    Inventors: Nils J. Christensen, Joseph Levy
  • Patent number: 4150243
    Abstract: A process for the tertiary dealkylation of a tertiary alkyl containing m- and/or p-cresol wherein a tertiary alkyl containing m- and/or p-cresol is continously introduced into a reaction vessel with a small amount of sulfuric acid or an quivalent amount of a sulfonic acid and the reaction vessel contains a high concentration of m- and/or p-cresol or a high boiling phenol which under the prevailing reaction conditions is not substantially vaporized from the reaction mixture. The reaction mixture is maintained at a temperature of no greater than 230.degree. C. The reaction products are withdrawn continuously from the reactor (and separated into its components) and at the same time a small amount of the reaction mixture being withdrawn intermittently or continously from the reactor.
    Type: Grant
    Filed: November 22, 1976
    Date of Patent: April 17, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter W. Bruck, Helmut Fiege, Johann Renner, Feliks Bitners, Josef Haydn, Karlfried Wedemeyer
  • Patent number: 4125560
    Abstract: The invention pertains to an aromatic amines synthesis process, fundamentally characterized by the fact that it consists of carrying out the ammonolysis of phenols under pressure in liquid phase by ammonia in aqueous solution.
    Type: Grant
    Filed: July 15, 1976
    Date of Patent: November 14, 1978
    Assignee: Universite Libre de Bruxelles Faculte des Sciences Appliquees
    Inventors: Claude L. Delaunois, Willy O. De Graeve
  • Patent number: 4112003
    Abstract: Polyphenols of the general formula: ##STR1## wherein R represents a readily cleavable ether group and R' represents a hydrogen atom or a lower alkoxycarbonyl, such as the methoxycarbonyl or ethoxycarbonyl group, and of phloroglucinol, are made by heating a compound of the general formula: ##STR2## wherein R and R' have the same significance given above, with an alkali metal alcoholate and, if desired, converting the resulting compound of formula I into pholoroglucinol by ether-cleavage and removal of any ester group denoted by R' which may be present in accordance with methods known per se.
    Type: Grant
    Filed: February 3, 1977
    Date of Patent: September 5, 1978
    Assignee: Givaudan Corporation
    Inventor: Ulrich Huber
  • Patent number: 4110253
    Abstract: This invention provides an improved process for the disproportionation of highly alkylated phenols with phenol using an improved magnesium oxide catalyst promoted with tungsten oxide, silica sol, and sodium silicate. The method provides a catalyst having a high reactivity, high surface area, and high crush strength compared to known magnesium oxide, tungsten oxide catalysts. The catalyst is useful in phenol methylation and disproportionation. The effect of silica sol and sodium silicate is synergistic since these materials alone will not catalyze these reactions. Surprisingly, the catalyst will not disproportionate olefins.
    Type: Grant
    Filed: January 24, 1977
    Date of Patent: August 29, 1978
    Assignee: Continental Oil Company
    Inventor: Bruce E. Leach
  • Patent number: 4110544
    Abstract: A process for preparing cresols from di-hydrocarbyl-substituted cresols, wherein the hydrocarbyl groups contain from 3 to 7 carbon atoms, is disclosed. In the process the di-hydrocarbyl-substituted cresol is contacted with a catalyst (e.g. alumina) in the liquid phase at elevated temperatures and pressure. 4,6-di-t-butyl-m-cresol is a typical feedstock.
    Type: Grant
    Filed: January 13, 1977
    Date of Patent: August 29, 1978
    Assignee: Continental Oil Company
    Inventors: Thomas E. Goodwin, Charles M. Starks
  • Patent number: 4110543
    Abstract: A method of preparing hydrocarbyl-substituted cresols is disclosed. The method comprises heating a mixture of mono- or di-hydrocarbyl-substituted cresols and an alcohol, which is benzyl alcohol or a C.sub.1 -C.sub.10 aliphatic alcohol, at an elevated temperature in the presence of a catalytic amount of alumina. The product contains at least one hydrocarbyl substituent corresponding to the hydrocarbon moiety of the alcohol used in the process. A typical process employs 4,6-di-t-butyl-m-cresol and isopropanol to prepare a product mixture containing a substantial amount of thymol.
    Type: Grant
    Filed: February 24, 1977
    Date of Patent: August 29, 1978
    Assignee: Continental Oil Company
    Inventors: Thomas E. Goodwin, Charles M. Starks
  • Patent number: 4100207
    Abstract: A method of preparing methyl-substituted phenols is disclosed. The method comprises heating a mixture of mono- or di-hydrocarbyl-substituted cresols and methanol at an elevated temperature in the presence of a catalytic amount of magnesium oxide.
    Type: Grant
    Filed: February 24, 1977
    Date of Patent: July 11, 1978
    Assignee: Continental Oil Company
    Inventors: Thomas E. Goodwin, Charles M. Starks