Aromatic Feed Patents (Class 585/410)
  • Patent number: 11807664
    Abstract: An objective of the present invention is to provide methods of producing a cyclic organic compound using a continuous stirred tank reactor(s) (CSTR), the methods being capable of achieving excellent impurity-suppressing effects (quality improvement), reduction in reaction-tank size, continuous production, and such. The present inventors conducted studies on cyclization reactions using a CSTR(s), which had not been conventionally used for cyclization reactions for cyclic compounds. As a result, the inventors have found that the present methods can achieve excellent impurity-suppressing effects (quality improvement), reduction in reaction-tank size, continuous production, and such, as compared with conventional cyclization methods.
    Type: Grant
    Filed: May 11, 2018
    Date of Patent: November 7, 2023
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Akie Homma, Zengye Hou, Hisashi Ito, Kiyoshi Sasakura
  • Patent number: 8796496
    Abstract: The present invention relates to a process for nonoxidatively dehydroaromatizing a reactant stream comprising C1-C4-aliphatics, comprising the steps of I. feeding reactant stream E into a reaction zone 1, converting reactant stream E under nonoxidative conditions in the presence of a particulate catalyst to a product stream P comprising aromatic hydrocarbons and discharging product stream P from reaction zone 1, II. transferring the catalyst with reduced activity as a result of deposited coke into a reaction zone 2, III. at least partly regenerating the catalyst with supply of a hydrogen-comprising gas stream H in a reaction zone 2, at least some of the coke deposited being converted to methane to form a methane-comprising gas stream M which is fed at least partly to reaction zone 1, IV. discharging the catalyst from reaction zone 2 and V.
    Type: Grant
    Filed: August 23, 2010
    Date of Patent: August 5, 2014
    Assignee: BASF SE
    Inventors: Christian Schneider, Martin Karches, Joana Coelho Tsou, Sebastian Ahrens, Dieter Stuetzer
  • Patent number: 8461404
    Abstract: A prolongated silica bound zeolite support comprising from about 85 wt % to about 95 wt % zeolite. A catalyst composition comprising a prolongated silica bound zeolite supporting at least one Group VIII metal and at least one halide. A process of making a prolongated silica bound zeolite support comprising mixing a zeolite, a prolongated silica, and water to form a mixture, and shaping the mixture into the prolongated silica bound zeolite support. A process of making a prolongated silica bound zeolite catalyst comprising mixing a zeolite, a prolongated silica, and water to form a mixture, shaping the mixture into a prolongated silica bound zeolite support, and adding one or more catalytic compounds to the prolongated silica bound zeolite support to form the prolongated silica bound zeolite catalyst.
    Type: Grant
    Filed: February 16, 2011
    Date of Patent: June 11, 2013
    Assignee: Chevron Phillips Chemical Company LP
    Inventor: Gyanesh P. Khare
  • Patent number: 8288602
    Abstract: The present invention describes a cost-efficient method for preparing di-substituted fluorenes in high yield.
    Type: Grant
    Filed: March 28, 2007
    Date of Patent: October 16, 2012
    Assignee: Total Petrochemicals Research Feluy
    Inventors: Alexander Z. Voskoboynikov, Artyom Y. Le Bedev, Andrey F. Asachenko, Abbas Razavi
  • Patent number: 8278237
    Abstract: A catalyst for producing aromatic compounds from lower hydrocarbons while improving activity life stability of methane conversion rate; benzene formation rate; naphthalene formation rate; and total formation rate of benzene, toluene and xylene is formed by loading molybdenum and copper on metallo-silicate serving as a substrate and then calcining the metallo-silicate. When the catalyst is reacted with a reaction gas containing lower hydrocarbons and carbonic acid gas, aromatic compounds are produced. In order to obtain the catalyst, it is preferable that molybdenum and copper are loaded on zeolite formed of metallo-silicate after the zeolite is treated with a silane compound larger than a pore of the zeolite in diameter and having an amino group and a straight-chain hydrocarbon group, the amino group being able to selectively react with the zeolite at a Bronsted acid point of the zeolite. It is preferable that a loaded amount of molybdenum is within a range of from 2 to 12 wt.
    Type: Grant
    Filed: February 13, 2008
    Date of Patent: October 2, 2012
    Assignee: Meidensha Corporation
    Inventors: Shinichi Yamada, Tomohiro Yamada, Yuji Ogawa, Hirokazu Akiyama, Takuya Hatagishi
  • Patent number: 7525001
    Abstract: The present invention provides a novel process for highly selective preparation of 2,6-dialkyltetralin, a key precursor for 2,6-dimethylnaphthalene (2,6-DMN), which does not require an extra step for purifying various isomers obtained from the conventional processes for 2,6-DMN. The present invention is advantageous to improve the synthetic yield, to simplify the operation and thus to reduce the production cost, since different starting materials and different pathways are exploited and thus the additional steps are not necessary.
    Type: Grant
    Filed: February 25, 2005
    Date of Patent: April 28, 2009
    Assignee: Seoul National University Industry Foundation
    Inventors: Young Gyu Kim, Woon Ki Kim, Byung Hyun Kim, Jong Gil Lee
  • Patent number: 7407928
    Abstract: Described is a solid phase benzopyran composition comprising predominately 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[G]-2-benzopyran and at least one other benzopyran compound. The novel compositions are used in augmenting, enhancing and/or imparting aromas in to consumable materials such as perfume compositions, perfumed articles including soaps, detergents, fabric softener compositions, fabric softener articles, fragranced candles, cosmetics, hair preparations, perfumed polymers and colognes. Also described is a process for producing the solid phase benzopyran compositions.
    Type: Grant
    Filed: February 10, 2003
    Date of Patent: August 5, 2008
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Bruce Mechanic
  • Publication number: 20080154035
    Abstract: The present invention relates to a coupling method between intramolecular carbon using the intramolecular cyclization reaction in situ of an allyl-indium compound derived from an allyl derivative containing an unsaturated hydrocarbon compound and indium, in presence of a transition metal compound catalyst. More particularly, the present invention relates to a coupling method between intramolecular carbon for preparing a cyclic compound having a vinyl group as a substituent by bonding a carbon in an allyl derivative containing an unsaturated hydrocarbon compound and a carbon in the unsaturated hydrocarbon compound via intramolecular cyclization reaction in situ of an allyl-indium compound as a coupling agent derived from the allyl derivative containing the unsaturated hydrocarbon and indium (In), in presence of a palladium catalyst.
    Type: Application
    Filed: July 17, 2007
    Publication date: June 26, 2008
    Applicant: PHIL HO LEE
    Inventors: Phil Ho LEE, Kooyeon LEE, Dong SEOMOON, Hyunseok KIM
  • Patent number: 7199274
    Abstract: The present invention relates to a simple process for preparing specifically substituted indenes of the formula (I) or (Ia) to compounds of the formula (II) serving as starting materials and to the use of the compounds of the formula (II) as starting materials for the synthesis of substituted indenes.
    Type: Grant
    Filed: October 18, 2003
    Date of Patent: April 3, 2007
    Assignee: Basell Polyolefine GmbH
    Inventors: Jörg Schulte, Jörg Schottek, Lothar Fisch
  • Patent number: 6720039
    Abstract: A liquid crystalline compound having a novel structure and a process for producing the same are provided. The liquid crystalline compound is represented by the following general formula (I): wherein R1 and R2 each independently represent a straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon group having 1 to 22 carbon atoms and may be attached directly to the aromatic ring without through X1 or X2; R3 represents a hydrogen atom, a cyano group, a nitro group, a fluorine atom, or a methyl group; and X1 and X2 each independently represent an oxygen atom, a sulfur atom, or a —CO—, —OCO—, —COO—, —N═CH—, —CONH—, —NH—, —NHCO—, or —CH2— group.
    Type: Grant
    Filed: October 6, 2000
    Date of Patent: April 13, 2004
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Junichi Hanna, Masahiro Funahashi, Komei Kafuku, Kyoko Kogo
  • Publication number: 20030032850
    Abstract: A process for the removal of hydrocarbon contaminants, such as dienes and olefins, from an aromatics reformate by contacting an aromatics reformate stream with a hydrotreating catalyst and/or a molecular sieve. The hydrotreating catalyst substantially converts all dienes to oligomers and partially converts olefins to alkylaromatics. The molecular sieve converts the olefins to alkylaromatics. The process provides an olefin depleted product which can be passed through a clay treater to substantially convert the remaining olefins to alkylaromatics. The hydrotreating catalyst has a metal component of nickel, cobalt, chromium, vanadium, molybdenum, tungsten, nickel-molybdenum, cobalt-nickel-molybdenum, nickel-tungsten, cobalt-molybdenum or nickel-tungsten-titanium, with a nickel molybdenum/alumina catalyst being preferred. The molecular sieve is an intermediate pore size zeolite, preferably MCM-22. The clay treatment can be carried out with any clay suitable for treating hydrocarbons.
    Type: Application
    Filed: October 8, 2002
    Publication date: February 13, 2003
    Inventors: Stephen H. Brown, Tarun K. Chaudhuri, Jose G. Santiesteban
  • Patent number: 6504069
    Abstract: 5-Tolyl-pent-2-ene is cyclized in liquid phase in the present of an aliphatic hydrocarbon to produce the corresponding dimethyltetralin. The use of the aliphatic hydrocarbon effectively prevents a side reaction such as dimerization of 5-tolyl-pent-2-ene to provide dimethyltetralin in a high yield. Also, 5-tolyl-pent-2-ene is cyclized in liquid phase or vapor phase in the presence of a catalyst comprising a carrier supporting sulfate ions to produce the corresponding dimethyltetralin. The catalyst supporting sulfate ions shows a high catalytic activity event at low temperatures. Therefore, the cyclization of 5-tolyl-pent-2-ene is conducted in a wide temperature range from low temperatures to high temperatures.
    Type: Grant
    Filed: February 14, 2000
    Date of Patent: January 7, 2003
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Youichi Kyuuko, Norio Fushimi, Makoto Takagawa
  • Patent number: 6472576
    Abstract: A process for producing 2,6-dimethylnapthalene from 1-(p-tolyl)-2-methylbutane, 1-(p-tolyl)-2-methylbutene or a mixture thereof by dehydrocyclization in the presence of a catalyst, comprising using non-acidic activated carbon as a catalyst.
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: October 29, 2002
    Assignee: Optatech Corporation
    Inventors: Christer Bergström, Marita Niemelä
  • Patent number: 6172273
    Abstract: A composition is prepared by a method which comprises mixing a first solid material comprising a platinum group metal, a rhenium component, a porous carrier material and, optionally, a halogen component and a second solid material comprising silica and bismuth. The thus-obtained composition is employed as a catalyst in the conversion of hydrocarbons to aromatics. In an alternate embodiment, hydrocarbons are converted to aromatics by sequentially contacting the hydrocarbons with the first solid material and then the second solid material.
    Type: Grant
    Filed: February 23, 2000
    Date of Patent: January 9, 2001
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 6127589
    Abstract: The invention concerns a preparation process for 2,6-dimethylnaphthalene in which 1-(p-tolyl)-2-methylbutane and/or 1-(p-tolyl)-2-methylbutene are dehydrocyclisized using a reduced vanadium catalyst. 2,6-dimethylnaphthalene can be used as starting material when manufacturing polyethylenenaphthalate. The conversion of this method is good and the selectivity of 2,6-dimethylnaphthalene can be improved by reducing the catalyst.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: October 3, 2000
    Assignee: Optatech Oy
    Inventors: Juha Jakkula, Vesa Niemi, Kari Vahteristo, Kari-Matti Sahala
  • Patent number: 6028027
    Abstract: Catalysts comprising iron and potassium and, if desired, further elements, which catalysts are suitable for dehydrogenating hydrocarbons to give the corresponding olefinically unsaturated hydrocarbons, are prepared by calcining a finely divided dry or aqueous mixture of an iron compound with a potassium compound and, if desired, compounds of further elements in a first step that agglomerates having a diameter of from 5 to 50 .mu.m and formed from smaller individual particles are obtained and, in a second step, preferably after shaping, calcining it at from 300 to 1000.degree. C., with the maximum calcination temperature in the second step preferably being at least 30.degree. below the calcination temperature in the first step. The catalysts thus prepared are useful, in particular, for dehydrogenating ethylbenzene to give styrene.
    Type: Grant
    Filed: March 17, 1998
    Date of Patent: February 22, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Baier, Christopher William Rieker, Otto Hofstadt, Wolfgang Buchele, Wolfgang Jurgen Popel, Hermann Petersen, Norbert Neth
  • Patent number: 5977422
    Abstract: This invention relates to an improved catalytic process for the alkylation of benzene or substituted benzene with alkyl halides for the continuous production of diarylalkanes or substituted derivatives thereof using ethylaluminum dichloride or methylaluminum dichloride as an organoaluminum dichloride catalyst. A process and apparatus are provided for reacting either benzene (or a substituted benzene compound) together with either an alkyl halide or an aromatic halide.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: November 2, 1999
    Assignee: The Dow Chemical Company
    Inventors: Steven A. Costello, Douglas L. Potts, Randall F. Pogue
  • Patent number: 5873994
    Abstract: An aromatization process for converting a portion of a cracked gasoline feedstock to aromatics utilizing a catalyst comprising an acid leached zeolite and tin under process conditions suitable for converting a portion of the cracked gasoline feedstock to aromatics.
    Type: Grant
    Filed: July 15, 1997
    Date of Patent: February 23, 1999
    Assignee: Phillips Petroleum Company
    Inventors: Charles A. Drake, An-hsiang Wu
  • Patent number: 5625102
    Abstract: A method of alkylating the side chain of alkyl-substituted aromatic hydrocarbons. The method comprises the steps of thermally treating an alumina by calcining in air and then degassing under vacuum to prepare an alumina carrier, loading an alkali metal on the alumina carrier by an impregnation method using the alkali metal dissolved in liquid ammonia, thermally treating the alkali metal loaded alumina carrier under vacuum to prepare a catalyst, then reacting an alkyl-substituted aromatic hydrocarbon with an aliphatic monoolefin, using the catalyst, under an atmosphere substantially free of oxygen, water and carbon dioxide gas to alkylate the side chain of the alkyl-substituted aromatic hydrocarbon.
    Type: Grant
    Filed: December 27, 1994
    Date of Patent: April 29, 1997
    Assignee: Mitsubishi Oil Co., Ltd.
    Inventors: Takaya Matsumoto, Yoshiichi Kumagai, Fumio Kumata
  • Patent number: 5463156
    Abstract: There is disclosed a method and apparatus for removing inhibiting substances produced in a dehydrogenation aromatization of poly cyclic compounds, the removal and consequent refinement of the reaction products occurring within the reaction system itself. To a dehydrogenation reaction apparatus comprising an evaporation section, a distillation, section, a reaction chamber including a catalyst bed section and a reflux condenser section, raw material is fed and then evaporated. After the vapor is passed through the catalyst zone section, it is liquefied at the reflux condenser section, and a portion or whole returned to the reaction chamber. The method is effective with poly cyclic compounds that cannot easily be handled by conventional methods. The reaction is highly efficient and proceeds with minimal catalyst deterioration.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: October 31, 1995
    Assignee: Sumikin Chemical Co., Ltd.
    Inventors: Takashiro Muroi, Toshio Sato, Ikuo Ito, Kyoichi Takeda
  • Patent number: 5401892
    Abstract: A method for preparing one or more specific dimethyltetralins from either 5-(o-, m-, or p-tolyl)-pent-1- or -2-ene or 5-phenyl-hex-1- or -2-ene, and optionally for preparing one or more specific dimethylnaphthalenes from the aforesaid dimethyltetralins is disclosed wherein the orthotolylpentene or phenylhexane is cyclized to the dimethyltetralin using an ultra-stable crystalline aluminosilicate molecular sieve Y-zeolite.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: March 28, 1995
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Joyce D. Lamb, Gregory S. Williams
  • Patent number: 5396008
    Abstract: There is disclosed a process for producing dimethyltetralin consisting of 1,5-, 1,6- and 2,6-dimethyltetralin which comprises cyclizing 5-tolyl-penta-2-ene in gaseous state in the presence of diluent by the use of a catalyst comprising a crystalline aluminosilicate and a carrier and optionally a molding assistant. The abovementioned process is capable of producing industrially useful dimethyltetralin as the starting raw material for dimethylnaphthalene with high yield and high selectivity with minimized side reactions over a long stabilized period.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: March 7, 1995
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Shinji Ozawa, Makoto Takagawa, Kenji Dnamasa
  • Patent number: 5382733
    Abstract: Disclosed herein is a process for preparing naphthalene or a derivative thereof, which comprises subjecting a benzene derivative having at least one substituted or non-substituted aliphatic hydrocarbon group and being capable of forming a naphthalene ring to cyclodehydrogenation in the presence of a zirconia catalyst containing chromium in an oxidized state.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: January 17, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Masayuki Otake, Akio Nakanishi
  • Patent number: 5284987
    Abstract: A method for the acid catalyzed cyclization of an alkenylbenzene feedstock to a dimethyltetralin in a liquid phase reaction wherein the desired dimethyltetralin is removed from the reaction mixture by distillation simultaneously with the addition of the feedstock to the reaction mixture.
    Type: Grant
    Filed: February 5, 1992
    Date of Patent: February 8, 1994
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5276230
    Abstract: There is disclosed a process for efficiently producing 2,6-dimethylnaphthalene used for the production of polyethylene naphthalate which comprises subjecting 2-methyl-1-(p-tolyl)butene and/or 2-methyl-1-(p-tolyl)butane as a starting raw material to cyclization dehydrogenation reaction by the use of a catalyst comprising a platinum component and at least one component selected from the group consisting of alkali metals and alkaline earth metals each being supported on aluminum oxide. The above process enables the production of the objective compound in a high yield at a low cost by using the catalyst having high safety and stability from the widely available starting material, thereby enhancing the industrial significance of the process.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: January 4, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kenji Inamasa, Norio Fushimi, Makoto Takagawa
  • Patent number: 5093541
    Abstract: Cyclobutarenes are prepared by pyrolyzing a suitable benzene, naphthalene, or pyridine derivative in the presence of an amount of steam effective to substantially reduce the partial pressure of the pyrolyzing compound.
    Type: Grant
    Filed: May 25, 1989
    Date of Patent: March 3, 1992
    Assignee: The Dow Chemical Company
    Inventors: George J. Quarderer, Mark J. Beitz, Fred C. Stone, Patrick M. O'Donnell
  • Patent number: 5082983
    Abstract: A process for reducing the benzene content of a reformate stream in a conventional catalytic cracking reactor wherein a heavy hydrocarbon feed is cracked to lighter products by contact with a supply of hot regenerated cracking catalyst is disclosed. The reformate can be mixed with the heavy feed to the cracking reactor, but preferably reformate contacts hot regenerated cracking catalyst before the heavy feed is added. Benzene content is reduced by alkylation with reactive fragments created in the cracking reactor, or by transalkylation with alkyl aromatics. Benzene removal can be enhanced by adding a light reactive gas such as ethylene to the cracking reactor, by adding heavier aromatics, such as a light cycle oil, or both. The reaction is preferably conducted in an FCC riser reactor, but may be conducted in a moving bed cracking reactor.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: January 21, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Lloyd L. Breckenridge, Diane V. Jorgensen, Ajit V. Sapre
  • Patent number: 5073670
    Abstract: A method for preparing one or more specific dimethyltetralins from either 5-(o-, m-, or p-tolyl)-pent-1-or -2-ene or 5-phenyl-hex-1- or -2-ene, and optionally for preparing one or more specific dimethylnaphthalenes from the aforesaid dimethyltetralins is disclosed.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: December 17, 1991
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Joyce D. Lamb, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5068479
    Abstract: A process for preparing 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene of the formula I ##STR1## comprises reacting p-cymene of the formula II ##STR2## with a hexene of the formula IIIa, IIIb and/or IIIc ##STR3## in the presence of a catalytic amount of aluminum halide and a catalytic amount of a triphenylmethyl compound of the formula IV ##STR4## wherein R.sup.1, R.sup.2 and R.sup.3 are each, independently of one another, hydrogen, C.sub.1 -C.sub.4 -alkyl, nitro or halogen and X is hydrogen or halogen.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: November 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Herbert Mayr, Rainer Becker
  • Patent number: 5034561
    Abstract: A method is provided for cyclizing an alkenylbenzene to a dialkyltetrahydronaphthalene (dialkyltetralin) in the presence of a solid cyclization catalyst constituted by a relatively low acidity, ultrastable, hydrogen form of crystalline aluminosilicate zeolite Y having a sodium oxide-to-alumina bulk molar ratio in the range of about 0.001 to about less than 1, a unit cell size no greater than about 24.3 Angstroms, and a sodium content of no more than about 0.4 percent by weight, calculated as elemental sodium and based on the weight of the zeolite. This catalyst provides more activity, more stability, higher product purity, and higher product yields than known prior art zeolite cyclization catalysts notwithstanding its relatively lower acidity. A preferred alkenylbenzene is 5-(o-tolyl)-pent-2-ene which is converted in relatively high yields and relatively high selectivities to 1,5 dimethyltetrahydronaphthalene.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: July 23, 1991
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Gregory S. Williams, Ian C. Zaenger
  • Patent number: 5030781
    Abstract: A method for preparing one or more specific dimethyltetralins by cyclization of either 5-(o-, m, or p-tolyl)-pent-1- or -2-ene or 5-phenyl-hex-1- or -2-ene, with additional cyclization treatment, and optionally cracking, of a heavy fraction of the cyclization product, is disclosed.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: July 9, 1991
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5023390
    Abstract: A process for production of 2,6-dimethylnaphthalene is disclosed; comprising the steps: (1) an acylation step where 2,4-dimethylisobutyrophenone is produced from m-xylene, propylene and carbon monoxide: (2) a hydrogenation step where the carbonyl group of the above 2,4-dimethylisobutyrophenone is hydrogenated: and (3) a dehydrogenation and cyclization step where the above hydrogenated product is subjected to dehydrogenation and cyclization to produce the desired 2,6-dimethylnaphthalene. The process enables efficiently producing high quality or high purity 2,6-dimethylnaphthalene.
    Type: Grant
    Filed: September 12, 1989
    Date of Patent: June 11, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Abe, Shuji Ebata, Hiroshi Machida, Koichi Kida
  • Patent number: 5008479
    Abstract: A process for production of 2,6-dimethylnaphthalene is disclosed, comprising the steps: (1) an acylation step where p-tolyl sec-butyl ketone is produced from toluene, n-butene and carbon monoxide: (2) a hydrogenation step where the carbonyl group of the p-tolyl sec-butyl ketone is hydrogenated: and (3) a dehydrogenation and cyclization step where the hydrogenated product obtained above is subjected to dehydrogenation and cyclization to produce the desired 2,6-dimethylnaphthalene. The process enables efficiently producing a high quality or high purity 2,6-dimethylnaphthalene.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: April 16, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Abe, Seiji Uchiyama, Takahiro Ojima, Koichi Kida
  • Patent number: 5003123
    Abstract: A process is disclosed for the pyrolytic production of a cyclobutenoarene from an o-alkylarylmethyl halide, the process involving the condensation of the pyrolysis product stream in the presence of water vapor. Water can be added to the process with the starting material so that it is present during pyrolysis and/or it can be added to the mixed product stream from the pyrolysis zone. The presence of water vapor in the product stream enables the condensation of aqueous hydrogen halide and provides a relatively simple way to reduce corrosion of downstream equipment.
    Type: Grant
    Filed: May 17, 1990
    Date of Patent: March 26, 1991
    Assignee: Shell Oil Company
    Inventor: Larry S. Corley
  • Patent number: 4950825
    Abstract: A method for preparing one or more specific dimethyltetralins from either 5-(o-, m-, or p-tolyl)-pent-1- or -2-ene or 5-phenyl-hex-1- or -2-ene, and optionally for preparing one or more specific dimethylnaphthalenes from the aforesaid dimethyltetralins is disclosed.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: August 21, 1990
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Joyce D. Lamb, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 4935571
    Abstract: A process for the recovery of a cyclobutenoarene such as benzocyclobutene from a mixed reaction product is disclosed. The mixed reaction product is contacted with an aqueous acid solution so as to convert impurities to species such as oligomers and water addition products which have sufficiently reduced volatility that they can be separated from cyclobutenoarene by distillation. The cyclobutenoarene is then recovered from the organic phase.
    Type: Grant
    Filed: August 31, 1988
    Date of Patent: June 19, 1990
    Assignee: Shell Oil Company
    Inventor: Larry S. Corley
  • Patent number: 4926000
    Abstract: Benzene reacts with itself to produce liquid aromatic compounds having more than 6 carbon atoms, in the presence of zeolite characterized as a medium pore size and having an activity defined by an alpha value of at least 50.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: May 15, 1990
    Assignee: Mobil Oil Corporation
    Inventor: Roger A. Morrison
  • Patent number: 4877916
    Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes wherein a cyclialkylation reaction between an olefinic compound of the general formula ##STR1## where R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently defined and each is a substituent which does not interfere substantially with a Friedel-Crafts reaction, and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, an alkyl halide or hydrogen halide, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process, which may be practiced in an unhalogenated hydrocarbon solvent, produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient or less expensive process methodology than many processes known heretofore.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877910
    Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes is disclosed wherein a cyclialkylation reaction between an olefinic compound of the general Formula ##STR1## wherein R.sup.4, R.sup.5, and R.sup.6 are independently defined and each represents a substituent which does not substantially interfere with a Friedel-Crafts type reaction and where R.sup.5 and R.sup.6 are other than H, and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, an alkyl halide or hydrogen halide, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient, or less expensive process methodology than many processes known heretofore.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877915
    Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes wherein a cyclialkylation reaction between an olefinic compound of the general formula ##STR1## wherein R.sup.4, R.sup.5, and R.sup.6 are substituents which do not interfere with a Friedel-Crafts-type reaction and R.sup.5 and R.sup.6 are other than H, and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient or less expensive process methodology than many processes known heretofore.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877911
    Abstract: A process for the production of polyalkyl tetrahydronaphthalenes is disclosed wherein a cyclialkylation reaction between an olefinic compound of the general Formula ##STR1## wherein R.sup.5, R.sup.6 and R.sup.7 are independently defined and each is a substituent which does not interfere with a Friedel-Crafts type alkylation reaction, and a substituted benzene compound is carried out in the presence of an alkyl halide, a Lewis acid and a phase transfer agent. The subject process, which may be practiced in an unhalogenated hydrocarbon solvent, produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using safer solvents and better, more convenient, or less expensive process methodology than many processes known heretofore.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877914
    Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes is disclosed wherein a cyclialkylation reaction between an olefinic compound of the general Formula ##STR1## wherein R.sup.4, R.sup.5 and R.sup.6 are independently defined and each represents a substituent which does not interfere substantially in Friedel-Crafts type reactions and R.sup.5 and R.sup.6 are other than H, and a substituted benzene compound is carried out in the presence of an alkyl halide, a Lewis acid and a phase transfer agent. The subject process produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient, or less expensive process methodology than many processes known heretofore.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877912
    Abstract: A process is disclosed for the production of 1,1,3,4,4,6-Hexamethyl-1,2,3,4-Tetrahydronaphthalene comprising reacting para-cymene with an olefinic compound selected from the group consisting of 2,3-dimethyl-1-butene and neohexene, in the presence of a reagent of the formula ##STR1## and further in the presence of an aluminum halide and I.sub.2, wherein in the above formula, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, independently, are H or a C.sub.1 -C.sub.3 straight chain, or branched alkyl, provided that no more than one of R.sup.1, R.sup.2 and R.sup.3 are H, and no more than one of R.sup.4, R.sup.5 and R.sup.6 are H.The subject process produces the desired compound in a surprisingly high yield, with a surprisingly high selectivity, and at a relatively high rate of reaction, using better, more convenient and/or less expensive process methodology than many processes known heretofore.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877913
    Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes wherein a cyclialkylation reaction between an olefinic compound of the general formula ##STR1## and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process, which may be practiced in an unhalogenated hydrocarbon solvent, produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient or less expensive process methodology than many processes known heretofore.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4851603
    Abstract: Cyclobutarenes are prepared by pyrolyzing a suitable benzene, naphthalene, or pyridine derivative in the presence of an amount steam effective to substantially reduce the partial pressure of the pyrolyzing compound.
    Type: Grant
    Filed: October 23, 1987
    Date of Patent: July 25, 1989
    Assignee: The Dow Chemical Company
    Inventors: George J. Quarderer, Fred C. Stone, Mark J. Beitz, Patrick M. O'Donnell
  • Patent number: 4764635
    Abstract: A hydroaromatic compound is aromatized by heating it at about 100.degree.-300.degree. C. in the presence of a hydrogen acceptor. In a preferred embodiment of the invention, the hydroaromatic compound is a dihydronaphthalene bearing an electron-withdrawing substitutent, e.g., a cyanodihydronaphthalene.
    Type: Grant
    Filed: August 14, 1986
    Date of Patent: August 16, 1988
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, David M. Mohr
  • Patent number: 4762943
    Abstract: A dihydroaromatic compound is aromatized by intimately contacting it with a base selected from alkali metal, alkaline earth metal, and tetraalkylammonium hydroxides, alkoxides, carbonates, and bicarbonates in the presence of a hydrogen acceptor. In a preferred embodiment of the invention, the dihydroaromatic compound is a dihydronaphthalene bearing an electron-withdrawing substituent, e.g., a cyanodihydronaphthalene.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: August 9, 1988
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, John R. Maloney
  • Patent number: 4738771
    Abstract: A novel catalytic absorbent composition is prepared with a synthetic copper or silver carbonate-containing material. The absorbent is useful for removing hydrogen sulfide and mercaptan sulfur from hydrocarbon oils, especially from feedstreams to a reformer.
    Type: Grant
    Filed: January 9, 1986
    Date of Patent: April 19, 1988
    Assignee: Union Oil Company of California
    Inventors: J. Wayne Miller, John W. Ward
  • Patent number: 4645585
    Abstract: A first aspect of the invention is concerned with fuels and particularly jet and diesel fuels which comprise blends of substituted mono cyclohexane material and two ring non-fused cyloalkane material. The first material may be n-propylcyclohexane or n-butylcyclohexane. The second material may be nuclear substituted bicyclohexyl and may include cyclohexylbenzene. A second aspect of the invention concerns producing constituents for the fuel from heavy aromatic materials by breaking down the heavy aromatics to naphthas, separating light napthas and other constituents of the fuel before reforming a heavy naptha fraction to provide a BTX fraction which may be treated by hydroalkylation or pyrolysis to provide two ring non-fused cycloalkanes. The product may be enriched by hydrogenation.
    Type: Grant
    Filed: February 27, 1985
    Date of Patent: February 24, 1987
    Assignee: The Broken Hill Proprietary Company Limited
    Inventor: Noam White
  • Patent number: 4458047
    Abstract: A novel process for making novel naphthalene hydrodimer mixtures which contain PTB in varying amounts and have improved plasticizing properties over PTB alone. The improved plasticizing composition is prepared by contacting a mixture of a hydronaphthalene (e.g., tetralin or an alkyltetralin) and naphthalene or an alkylnaphthalene with a strong acid catalyst. Another embodiment of the invention is the plasticized composition.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: July 3, 1984
    Assignee: Sun Tech, Inc.
    Inventor: William D. Vanderwerff