Isopropyl Or Isopropenyl Group Patents (Class 568/781)
  • Patent number: 9340419
    Abstract: Disclosed is a method and related system of regenerating a raw material for a hydrogen supply system of a fuel cell. The method includes reacting aluminum and a metal hydroxide to produce hydrogen in the hydrogen supply system of a fuel cell; and recovering an aluminum compound produced simultaneously with the hydrogen in the reaction. An aluminum hydroxide is obtained from the aluminum compound. The aluminum hydroxide is heat-treated to obtain an aluminum oxide. The aluminum oxide is reduced to obtain aluminum. The obtained aluminum is re-supplied as a raw material for producing the hydrogen.
    Type: Grant
    Filed: November 24, 2014
    Date of Patent: May 17, 2016
    Assignees: HYUNDAI MOTOR COMPANY, The Industry & Academic Cooperation in Chungnam National University (IAC)
    Inventors: Chang Ho Kim, Inchul Hwang, Hyung Ki Kim, Seong Seock Cho, Jong Hyeon Lee, Moon Hee Han, Hong Youl Ryu, Dae-Young Kim
  • Publication number: 20150148430
    Abstract: The present disclosure provides phenolic compounds useful in the treatment of neurological conditions such as convulsions and tremors, having the structure of Formula (I): wherein R2, R4, & R5, are as defined in the detailed description; pharmaceutical compositions comprising at least one of the compounds; and methods for treating neurological conditions.
    Type: Application
    Filed: November 24, 2014
    Publication date: May 28, 2015
    Inventors: Max Baker, Rajesh Kumar Mishra, John J. Talley, Eduardo J. Martinez
  • Publication number: 20140338009
    Abstract: A new and distinct clonal line of oregano named KI-Ov1850 and characterized by elevated levels of thymol and vigorous growth.
    Type: Application
    Filed: May 7, 2014
    Publication date: November 13, 2014
    Applicant: Kemin Industries, Inc.
    Inventors: Brindha Narasimhamoorthy, John A. Greaves, Liuqing Zhao, Zhiqiang Qui, Norman Cloud
  • Publication number: 20140336421
    Abstract: A new and distinct clonal line of oregano named KI-Ov1750 and characterized by elevated levels of carvacrol and vigorous growth.
    Type: Application
    Filed: May 7, 2014
    Publication date: November 13, 2014
    Applicant: Kemin Industries, Inc.
    Inventors: Brindha Narasimhamoorthy, John A. Greaves, Liuqing Zhao, Zhiqiang Qui, Norman Cloud
  • Publication number: 20140112878
    Abstract: Provided is a tyrosinase activity inhibitor, a melanin production inhibitor, a skin-whitening agent, and a cosmetic product, which have an excellent tyrosinase activity inhibitory effect with a high level of safety. A tyrosinase inhibitor comprising isopropylmethylphenol as an active ingredient.
    Type: Application
    Filed: April 24, 2013
    Publication date: April 24, 2014
    Inventor: Kao Corporation
  • Publication number: 20130345469
    Abstract: A feed additive includes at least one of p-thymol, a salt derivative and an ester derivative thereof for animals.
    Type: Application
    Filed: September 2, 2013
    Publication date: December 26, 2013
    Applicant: GUANGZHOU INSIGHTER BIOTECHNOLOGY CO., LTD.
    Inventors: Xianfeng PENG, Zonghua TAN
  • Publication number: 20130203830
    Abstract: The invention is related to compounds for prevention of cell injury or protection of cells. The compounds are involved in the maintenance or the increase of hydrogen sulphide in cells, which results in a protection of the cells or the prevention of cell injury. The compounds of the invention can be used in cell culture and tissue culture techniques. They can also be used in several medical conditions such as ischemia, reperfusion and hypothermia, or for preserving organs which are used for transplantation.
    Type: Application
    Filed: April 18, 2011
    Publication date: August 8, 2013
    Applicant: SULFATEQ B.V.
    Inventors: Fatemeh Talaei, Robert Henk Henning, Adrianus C. Van der Graaf
  • Publication number: 20120142786
    Abstract: Oregano extract can act as a stimulant, yet it does not interfere with sleep patterns or induce nervousness the way many stimulants such as caffeine can. It also has the benefits of promoting improved vigilance, improving attention and ability to focus on a task, and improving general alertness.
    Type: Application
    Filed: February 19, 2010
    Publication date: June 7, 2012
    Inventors: Regina Goralczyk, Jonas Wittwer, Hasan Mohajeri
  • Publication number: 20120034312
    Abstract: This invention relates to the use of 4-isopropyl-3-methylphenol (IPMP) for combating inflammation and compositions comprising IPMP for such use.
    Type: Application
    Filed: April 1, 2010
    Publication date: February 9, 2012
    Inventor: Jingjun Yang
  • Publication number: 20110281956
    Abstract: Disclosed is an use of Spanish oregano (Thymus capitatus) extract, summer savory (Satureja hortensis) extract or carvacrol for treating metabolic diseases. More specifically, the present disclosure relates to a composition containing Spanish oregano extract or summer savory extract, carvacrol, which is an aromatic oil component frequently found in mint, oregano, thyme, bergamot camphor tree or thyme thymol, as an active ingredient, for preventing and treating a metabolic disease selected from the group consisting of obesity, fatty liver, hyperlipidemia and diabetes, an use thereof, and a method of using the same. The disclosed composition, use and method are useful for weight loss, suppression of abdominal fat accumulation, treatment of fatty liver, reduction of cholesterol and free fatty acid in plasma and liver tissue, and improvement of blood glucose level and insulin resistance.
    Type: Application
    Filed: July 25, 2011
    Publication date: November 17, 2011
    Applicant: INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YONSEI UNIVERSITY
    Inventor: Tae Sun Park
  • Publication number: 20110281949
    Abstract: Use of alkyl phenol and monocyclic monoterpene-derived compounds in the treatment of neuronal damage and in inhibiting activity of TRPC and non-thermo-TRPM channels, and use of bicyclic monoterpene-derived compounds in activating TRPC and non-thermo-TRPM channels.
    Type: Application
    Filed: February 3, 2011
    Publication date: November 17, 2011
    Inventors: Baruch Minke, Moshe Parnas
  • Publication number: 20100331566
    Abstract: The invention provides synthetic methods that utilize bromo or chloro substituents as blocking groups during the functionalization of aromatic rings, as well as compounds that are prepared from such methods.
    Type: Application
    Filed: June 25, 2010
    Publication date: December 30, 2010
    Inventors: Leslie S. Jimenez, Ahalya Ramanathan
  • Publication number: 20100249246
    Abstract: A (?)-stereoisomer of formula (I): (formula I), wherein X is H or F; or a pharmaceutically acceptable salt or prodrug thereof, is useful as an anesthetic.
    Type: Application
    Filed: May 8, 2008
    Publication date: September 30, 2010
    Applicant: PharmacoFore, Inc.
    Inventor: Thomas E. Jenkins
  • Patent number: 7596836
    Abstract: A nose and throat anti-influenza solution is described that decreases the likelihood influenza infection and its spread. The solution's components are readily available and have been used to treat humans for other ailments previously, leading to an easily implemented, scalable, safe, and cost-effective solution. The core components of the solution include: specially denatured alcohol (SDA); Triton x-100; sodium saccharin; 1,8 cineole (eucalyptol); thymol; methyl salicylate; menthol; sorbitol and/or glycerin; sodium benzoate; poloxamer 407; polysorbate 80; and distilled water. Optionally, the solution also includes one or more of the following: citric acid; sambucus nigra agglutinin; a lectin that binds 2,3 sialic acid; nonoxynol-9; sialyllactose; a protease; a protease inhibitor; and/or chloroquine. The solution is applied to the nasal cavity via a pre-moistened cotton swab or a pre-moistened facial tissue and the solution is applied to the back of the throat via a spray, gum, or gargle solution.
    Type: Grant
    Filed: May 2, 2007
    Date of Patent: October 6, 2009
    Inventor: Steve W. Schwartz
  • Publication number: 20080306285
    Abstract: Disclosed herein are heat-labile prodrugs, their preparation and uses.
    Type: Application
    Filed: April 28, 2008
    Publication date: December 11, 2008
    Applicant: ALEXZA PHARMACEUTICALS, INC.
    Inventors: Ron L. Hale, Dennis W. Solas, Kathleen Simis, Amy T. Lu, Peter M. Lloyd
  • Patent number: 7288683
    Abstract: 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: Grant
    Filed: June 16, 2006
    Date of Patent: October 30, 2007
    Assignee: General Electric Company
    Inventors: Hugo G. E. Ingelbrecht, David Parrillo, Mukund Parthasarathy, Gert-Jan Schoenmakers, Geuch Zijlma
  • Patent number: 7282617
    Abstract: A process for making medium and long chain alkylaromatics and alkylphenols having a high level of anti-Markovnikov addition of the alkyl group. The alkylaromatics and alkylphenols made by the process of the present invention have enhanced stability and are particularly well suited to make highly stable oil additives and enhanced oil recovery surfactants.
    Type: Grant
    Filed: March 31, 2006
    Date of Patent: October 16, 2007
    Assignee: Chevron U.S.A. Inc.
    Inventors: William L. Schinski, Curt B. Campbell
  • Patent number: 6846962
    Abstract: In a method for the production of o-alkyl phenols by conversion of phenol with an alkanol at elevated temperature in the gas phase in the presence of a metal catalyst, the conversion takes place in at least two stages wherein the alkanol/phenol molar ratio in each reaction stage is set to a value of approximately ?0.4; a clear increase in the selectivity for the o-alkyl phenol is obtained.
    Type: Grant
    Filed: November 15, 2002
    Date of Patent: January 25, 2005
    Assignee: Rutgers Chemicals AG
    Inventors: Jörg Talbiersky, Edgar Fuhrmann, Wolfgang Brüggemann
  • Patent number: 6784325
    Abstract: The isomerization of an alkylated phenol composition that contains an ortho-alkyl substituted phenol component to isomerize and reduce the level of ortho-alkyl substituted phenol component therein can be accomplished by heating that composition in the presence of a catalytically effective amount of a solid acid catalyst to carry out such isomerization and reduction in the level of ortho-alkyl substituted phenol. Examples of suitable solid acid catalysts can be selected from the H-form zeolites, the supported sulfonic acids, and the heteropoly acids. The resulting isomerized product can be subsequently phosphorylated.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: August 31, 2004
    Assignee: Akzo Nobel N.V.
    Inventors: Anantha N. Desikan, George E. Whitwell
  • Patent number: 6504065
    Abstract: Reaction of a phenol with a metal salt of an alcohol produces a metal phenolate salt of a phenol. When a hindered phenol is used a hindered metal phenolate is produced. Such hindered metal phenolate salts are useful in driving the synthesis reaction of hindered phenol esters and phosphite esters to completion.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: January 7, 2003
    Assignee: General Electric Company
    Inventors: William Palmer Enlow, Gary Vincent Marlin
  • Patent number: 6322825
    Abstract: The invention relates to pharmaceutical compounds which are based on the anti-flammatory properties of etheric oils selected from the group consisting of Origanum vulgaris, Thymus vulgaris, Mentha piperita, Thymus serpilum, Saturea hortensis, Saturea montana, Saturea subricata, Carum corticum, Thymus zugis, Ocimum gratisimum, Moranda pungtata, Mosla japanoica and Salvia officinalis. Preferably the etheric oils, obtained at the distillation of Origanum vulgaris, Thymus vulgaris and/or Mentha piperita are used. Such pharmaceutical compounds, compared to synthetic sulfonamids, antibiotics and cortisones do not create biorecidives in the human body as well as in animal meat and milk and milk and do not contribute to the resistance of microorganism against pharmaceutical compositions in general.
    Type: Grant
    Filed: July 19, 1999
    Date of Patent: November 27, 2001
    Assignee: Ropapharm B.V.
    Inventor: Dusan Ninkov
  • Patent number: 5591311
    Abstract: A process for purifying impure 2,6-diisopropylphenol (DIP) mixtures having lower and higher boiling phenolic impurities is described. The process involves washing the mixture with aqueous alkali metal hydroxide solution in an inert atmosphere and separating the aqueous and organic phases, washing the resulting organic phase with water, and then subjecting the water-washed organic phase to distillation in an inert environment to recover purified DIP. Since only one distillation is required rather than two, the development of impurities in the DIP caused by in situ oxidation reactions at elevated temperatures due to the inevitable presence of traces of air in commercial distillation facilities is reduced to acceptable levels.
    Type: Grant
    Filed: October 26, 1995
    Date of Patent: January 7, 1997
    Assignee: Albemarle Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 5414156
    Abstract: This invention relates to the process for producing ortho-isopropylated phenol derivatives having following general formula (VIII). ##STR1## (in the above formula, R.sub.1 is a hydrogen or a low alkyl group of C.sub.1 -C.sub.4)A process for producing ortho-isopropylated phenol derivatives (VIII) of the present invention is characterized by obtaining position isomer desired by means of Claisen rearrangement of phenyl allyl ether without catalyst in atmosphere, and then obtaining only one isomer by oxidation and reduction of the above-obtained position isomer. According to the present invention, ortho-alkylated phenol derivatives (VIII) having high purity at low temperature and low pressure can be prepared without producing a by-product and requirement of the complicated separation procedure.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: May 9, 1995
    Assignees: Dong Kook Pharmaceutical Co., Ltd., Ki-Beom Kwon
    Inventors: Jung H. Cho, Kie H. Nam, Wan S. Kim
  • Patent number: 5356976
    Abstract: 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: Grant
    Filed: July 12, 1993
    Date of Patent: October 18, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Paul Dubs, Rita Pitteloud
  • Patent number: 5344997
    Abstract: 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: Grant
    Filed: December 14, 1992
    Date of Patent: September 6, 1994
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 5302732
    Abstract: 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: Grant
    Filed: September 14, 1992
    Date of Patent: April 12, 1994
    Assignee: UOP
    Inventors: Karl Z. Steigleder, Christine M. Conway, David M. Baldwin, Diane C. Dierking
  • Patent number: 5274174
    Abstract: 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: Grant
    Filed: June 10, 1993
    Date of Patent: December 28, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5245057
    Abstract: A continuous horizontal reactor system and process for employing such a system. In one embodiment, a reactor system having a cylindrical multi-compartment vessel, the compartments intercommunicating via a common overhead space or separated spaces from which vapor with reaction product or by-products may be removed, and from which liquid effluent with reaction products or by-products may be removed and reactants and catalyst flowable into each compartment and agitators in each compartment. Such a reactor system for producing liquid epoxy resins. Processes using such a reactor to produce reaction products, e.g. liquid epoxy resins.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: September 14, 1993
    Assignee: The Dow Chemical Company
    Inventor: Robert P. Shirtum
  • Patent number: 5243116
    Abstract: Alkylated benzenes such as ethylbenzene and cumene are produced by alkylation and/or transalkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 30:1 and a crystalline structure which is determined by X-ray diffraction to be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: September 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • 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: 5175376
    Abstract: The object of the invention is a new method for the purification of 2,6-diisopropyl phenol (propofol). The invention is characterized in that the raw product obtained from the alkylation of propene with phenol is crystallized at a temperature where propofol crystallizes but the isomers and other phenol derivatives formed in the reaction are still in liquid form, i.e. at a temperature of -25.degree. to +18.degree. C. especially at -20.degree. to -10.degree. C., without a solvent or using a suitable solvent, such as hexane or petrol ether.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: December 29, 1992
    Assignee: Leiras Oy
    Inventors: Kauko Nieminen, Peter Essen
  • Patent number: 5175375
    Abstract: The invention relates to producing ortho isopropyl phenol catalytically by contacting phenol with isopropanol or propylene, at a temperature of from about 200.degree. C. to about 300.degree. C., with ZSM-12 and zeolite Beta; and recovering ortho isopropyl phenol.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: December 29, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Stuart D. Hellring
  • Patent number: 5175377
    Abstract: The present invention provides an improved process for the production of ortho-alkyl phenols by vapor phase reaction of a phenol having at least one ortho-hydrogen with an alcohol, the improvement comprises soaking manganic oxide in an aqueous solution of alkali metal salt, separating the soaked manganic oxide from the solution, drying and calcining the soaked manganic oxide at a temperature of 300.degree.-600.degree. C. for a period of 1-3 hours to form an alkali metal oxide thereon, wherein the weight ratio of the alkali metal oxide to the manganic oxide is 0.5-0.0001 wt %, preferably 0.1-0.001 wt %.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: December 29, 1992
    Assignee: China Technical Consultants, Inc.
    Inventors: Ling-Wen Ho, Trong-Goang Lin, Yung-Chu Peng
  • Patent number: 5087772
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: February 11, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, Lan Shen
  • Patent number: 5082979
    Abstract: The invention relates to a process for the conversion of 8-hydroxymenthenes into 8-hydroxycymenes by treating the 8-hydroxymenthenes in the vapor phase with a dehydrogenation catalyst, e.g. palladium. The process is preferably carried out at 80.degree.-150.degree. C. The hydroxymenthene vapor is preferably passed through the catalyst system at a pressure below 8 kPa and/or with the aid of an inert gas or vapor. Oxygen may be present as a hydrogen acceptor. The process is particularly suitable for converting 8-hydroxy-p-menth-l-ene into 8-hydroxy-p-cymene. The reaction products are of value as intermediates in the preparation of fragrance chemicals.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: January 21, 1992
    Assignee: Unilever Patent Holdings B.V.
    Inventor: Christopher P. Newman
  • Patent number: 5068466
    Abstract: The invention relates to a process for the conversion of 8-hydroxymenthenes into 8-hydroxycymenes by reacting the 8-hydroxymenthenes in the liquid phase in the presence of a dehydrogenation catalyst, e.g. palladium and a hydrogen acceptor e.g. mesityl oxide. The process is preferably carried out at 80.degree.-150.degree. C. and in the presence of base. The process is particularly suitable for converting 8-hydroxy-p-menth-1-ene into 8-hydroxy-p-cymene. The reaction products are of value as intermediates in the preparation of fragrance chemicals.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: November 26, 1991
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Keith R. Motion, Christopher P. Newman
  • Patent number: 5030770
    Abstract: Thymol can be prepared by reaction of m-cresol with propene at elevated temperature and at atmospheric to superatmospheric pressure by using wide- and medium-pored zeolites which have a pore diameter of at least 5 .ANG. as heterogeneous catalysts.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: July 9, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Wimmer, Hans-Josef Buysch, Lothar Puppe
  • Patent number: 5012003
    Abstract: An improved process for preparing dithiobisphenols comprising reacting an appropriate phenol with an alkali metal hydride, an alkaline earth metal hydride or mixtures thereof and subsequently reacting the product thereof with sulfur monochloride.
    Type: Grant
    Filed: October 28, 1988
    Date of Patent: April 30, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: David H. Steinberg, John J. Luzzi
  • Patent number: 4978789
    Abstract: 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: Grant
    Filed: July 10, 1989
    Date of Patent: December 18, 1990
    Inventors: Katsuo Taniguchi, Shigeki Fujikawa, Yoshito Kurano
  • Patent number: 4880775
    Abstract: The present invention relates to novel poly-alkylated benzodioxin compounds possessing a musk-like aroma which are useful as fragrance materials. The compounds of the invention have the formula: ##STR1## where R.sup.1 to R.sup.4 are hydrogen or lower alkyl (C.sub.1 to C.sub.5), provided that the compound has no more than 18 carbon atoms. The invention provides for synthesis of a novel phenolic intermediate and synthesis of the compounds of the invention. The invention also provides fragrance compositions which utilize the compounds of the invention to modify, enhance, or impart a musk-like aroma to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: February 1, 1987
    Date of Patent: November 14, 1989
    Assignee: BASF K&F Corporation
    Inventors: Philip A. Christenson, Brian Drake, Paul J. Riker
  • 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: 4695658
    Abstract: A process for replacing an aromatic carbon-thallium bond with a carbon-oxygen bond. The process is particularly suitable for producing specific aromatic isomers by thallating an aromatic compound and replacing the thallium with a carboxylate group which can be further hydrolyzed if desired to form an aromatic hydroxyl compound.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: September 22, 1987
    Assignee: FMC Corporation
    Inventors: Edward C. Taylor, Alan H. Katz, Randy A. Bull, Lance R. Byers, Richard A. Brown
  • Patent number: 4689175
    Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances which have a very natural leather odor and correspond to the formula ##STR1## wherein one of the two symbols R.sub.1 and R.sub.2 represents a methyl group and the other a hydrogen atom or both symbols represent a hydrogen atom and R.sub.3 represents a n-propyl, allyl, 1-propenyl-, sec.butyl, 1-buten-3-yl, isobutyl or 2-methylpropen-3-yl group.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: August 25, 1987
    Assignee: Naarden International N.V.
    Inventor: Nicolaas L. J. M. Broekhof
  • Patent number: 4628127
    Abstract: 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: Grant
    Filed: June 25, 1985
    Date of Patent: December 9, 1986
    Assignee: Ethyl Corporation
    Inventors: Silas W. Holmes, Edward A. Burt, Dixie E. Goins
  • Patent number: 4599465
    Abstract: A process for producing an orthoalkylphenol which comprises reacting phenol with an olefin in a liquid phase in the presence of an alumina catalyst, characterized in that the water content in the liquid phase of the reaction system is maintained at a level of not higher than 250 ppm.
    Type: Grant
    Filed: June 5, 1985
    Date of Patent: July 8, 1986
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Akio Tamaru, Yoshiaki Izumisawa, Hidekichi Hashimoto, Kiyoji Kuma, Takashi Komaya, Masanobu Minagawa
  • Patent number: 4594459
    Abstract: Prepare p-isopropenyl phenol and other alkenyl aromatic compounds by contacting a dihydroxydiphenyl alkane or a related substituted diaromatic alkane with an alkaline catalyst and at least one gas under supercritical conditions such that p-isopropenyl phenol or the corresponding related alkenyl aromatic compound is produced.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: June 10, 1986
    Assignee: The Dow Chemical Company
    Inventor: Kimio Inoue
  • Patent number: 4484011
    Abstract: The process for preparing 4-isopropylphenol (4-IPP) from 2-isopropylphenol (2-IPP) comprising contacting phenol with 2-IPP in the presence of a catalyst system selected from: (1) the combination of sulfuric acid on comminuted acid clay and a molecular sieve; and (2) trifluoromethane sulfonic acid (TFMSA); at a temperature of from about 90.degree. C. to about 250.degree. C., preferably from about 110.degree. C. to about 200.degree. C., wherein the initial mole ratio of phenol/2-IPP is from about 6 to about 2, preferably from about 4 to about 2.5, for a sufficient period to give a mole ratio of 4-IPP/2-IPP in the reaction system of from about 0.6 to about 1.5, and preferably from about 0.8 to about 1.2, without significant meta-isopropylphenol formation, i.e., less than about 10 mole %. In the isolation procedure, distillation separates the reaction mixture into phenol, 2-IPP, and 4-IPP.
    Type: Grant
    Filed: December 2, 1983
    Date of Patent: November 20, 1984
    Assignee: Eastman Kodak Company
    Inventor: Dale E. Van Sickle
  • 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: 4469901
    Abstract: A process is disclosed for separating 5-isopropyl-m-cresol from other isopropylated m-cresols by treating a mixture of the isopropylated m-cresols with a metal halide salt. The metal halide salt preferentially forms a complex with 5-isopropyl-m-cresol over other related closely-boiling isopropylated m-cresols in the mixture. The preferentially-formed complex of 5-isopropyl-m-cresol may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, 5-isopropyl-m-cresol. The process is particularly suitable for isolating 5-isopropyl-m-cresol from closely-boiling isomers, and di-isopropylated m-cresols.
    Type: Grant
    Filed: January 3, 1984
    Date of Patent: September 4, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4451676
    Abstract: p-Alkenyl phenols are prepared by reacting an alkylated phenol having a replaceable hydrogen atom at the 4- position with an aliphatic aldehyde having two carbon atoms up to at least 20 carbon atoms in the molecule and a secondary amine.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: May 29, 1984
    Assignee: Ethyl Corporation
    Inventor: Charles R. Everly